[go: up one dir, main page]

WO2025227154A1 - Compositions tensioactives comprenant des carboxylates et leurs procédés de fabrication - Google Patents

Compositions tensioactives comprenant des carboxylates et leurs procédés de fabrication

Info

Publication number
WO2025227154A1
WO2025227154A1 PCT/US2025/026673 US2025026673W WO2025227154A1 WO 2025227154 A1 WO2025227154 A1 WO 2025227154A1 US 2025026673 W US2025026673 W US 2025026673W WO 2025227154 A1 WO2025227154 A1 WO 2025227154A1
Authority
WO
WIPO (PCT)
Prior art keywords
surfactant
acid
oil
compound
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/026673
Other languages
English (en)
Inventor
Upali Peter Weerasooriya
Karasinghe Arachchige Nadeeka UPAMALI
Nina Loahardjo
Christopher James BRITTON
Robert Matthew DEAN
Stephanie Sue ADKINS
Amol WALKE
Prasanta MAYAPUR
Gopal Sakharam TOTKEKAR
José C. J. M.D.S. MENEZES
Shrinivas KOTHEKAR
Gauri Santosh SUTAR
Ashwini Ashok MANDREKAR
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ultimate Eor Services LLC
Harcros Chemicals Inc
Original Assignee
Ultimate Eor Services LLC
Harcros Chemicals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ultimate Eor Services LLC, Harcros Chemicals Inc filed Critical Ultimate Eor Services LLC
Publication of WO2025227154A1 publication Critical patent/WO2025227154A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6409—Fatty acids
    • C12P7/6418—Fatty acids by hydrolysis of fatty acid esters

Definitions

  • EOR Enhanced Oil Recovery
  • 40-60% of the reservoir's original oil can typically be extracted compared with only 20-40% using primary and secondary recovery (e.g., by water injection or natural gas injection).
  • Enhanced oil recovery may also be referred to as improved oil recovery or tertiary oil recovery (as opposed to primary and secondary oil recovery).
  • Enhanced oil recovery may be achieved by a variety of methods including miscible gas injection (which includes carbon dioxide flooding), chemical injection (which includes polymer flooding, alkaline flooding, and surfactant flooding), microbial injection, or thermal recovery (which includes cyclic steam, steam flooding, and fire flooding).
  • miscible gas injection which includes carbon dioxide flooding
  • chemical injection which includes polymer flooding, alkaline flooding, and surfactant flooding
  • microbial injection or thermal recovery (which includes cyclic steam, steam flooding, and fire flooding).
  • thermal recovery which includes cyclic steam, steam flooding, and fire flooding.
  • Injection of a dilute solution of a water soluble polymer to increase the viscosity of the injected water can increase the amount of oil recovered from geological formations.
  • Aqueous solutions of surfactants such as petroleum sulfonates may be injected to lower the interfacial tension or capillary pressure that impedes oil droplets from moving through a reservoir.
  • Special formulations of oil, water and surfactant microemulsions have also proven useful. Such formulations often include co-solvent compounds to increase the solubility of the solutes in the presence of oil and decrease the viscosity of an emulsion.
  • compositions described herein can also be used as an emulsion breakers.
  • the compounds can include derivatives of components of cashew nutshell liquid (CNSL), including derivatives of anacardiac acid, derivatives of cardanol, derivatives of cardol, and derivatives of 2-methylcardol.
  • CNSL cashew nutshell liquid
  • the compositions can include anacardiac acid, derivatives of cardanol, derivatives of cardol, and derivatives of 2-methylcardol.
  • BO represents, individually for each occurrence, -CH2-CH(ethyl)-O- or - CH3CH(O-)CH3;
  • PO represents, individually for each occurrence, -CH2-CH(methyl)-O-;
  • EO represents, individually for each occurrence, -CH2-CH2-O-;
  • R 1 represents a C15 alkyl group or a C 15 alkenyl group;
  • R 2 represents hydrogen or methyl;
  • Q is hydrogen, -SOiM + , - SO3H, CH 2 CH(OH)CH2-SO 3 M + , CH 2 CH(OH)CH 2 -SO3H, -CH 2 C(O)O’M + , or - CH 2 C(O)OH;
  • M + when present, is a cation;
  • x is an integer from 0 to 15;
  • y is an integer from
  • z is an integer from 1 to 100.
  • BO represents -CH2-CH(ethyl)-O- or -CH3CH(O-)CH3;
  • PO represents -CH 2 - CH(methyl)-O-;
  • EO represents -CH2-CH2-O-;
  • R 1 represents a C15 alkyl group or a C15 alkenyl group;
  • Q is hydrogen, -SO 3 M + , -SO3H, CH 2 CH(OH)CH 2 -SO3M + , CH 2 CH(OH)CH 2 - SO3H, -CH 2 C(O)O"M + , or -CH 2 C(O)OH;
  • M + when present, is a cation;
  • x is an integer from
  • y is an integer from 0 to 50; and z is an integer from 1 to 100.
  • Formula III for example, provided herein are compounds defined by Formula III Formula III or a salt thereof, wherein BO represents -CH2-CH(ethyl)-O- or -CH3CH(O-)CH3; PO represents -CH2-CH(methyl)-O-; EO represents -CH2-CH2-O-; R 1 represents a C15 alkyl group or a C15 alkenyl group; R 3 represents hydrogen, an alkyl group, an alkoxy group, an aryl group, or an alkyleneoxy group; Q is hydrogen, -SCENE.
  • M + when present, is a cation; x is an integer from 0 to 15; y is an integer from 0 to 50; and z is an integer from 1 to 100.
  • aqueous compositions including a compound described herein and water.
  • Additional components including polymers (e.g., viscosity-enhancing water-soluble polymers), alkali agents, additional surfactants, co-solvents, and combinations thereof, can be present in the aqueous compositions.
  • surfactant compositions can comprise alkoxylating cashew nut shell liquid (CNSL) or a component thereof.
  • CNSL cashew nut shell liquid
  • polymers derived from condensation of an alcohol and an aldehyde wherein the alcohol comprises a compound defined by Formula IV
  • BO represents -CH2-CH(ethyl)-O- or -CH3CH(O-)CH3;
  • PO represents -CH2- CH(methyl)-O-;
  • EO represents -CH2-CH2-O-;
  • R 1 represents a C15 alkyl group or a C 15 alkenyl group;
  • Q is hydrogen;
  • x is an integer from 0 to 15;
  • y is an integer from 0 to 50; and
  • z is an integer from 0 to 100.
  • surfactant blends including a carboxylic acid surfactant and one or more additional components, wherein the one or more additional components can include a co- surfactant, a co-solvent, or a combination thereof
  • solubilizer including any of the disclosed surfactant blends.
  • a surfactant blend comprising a carboxylic acid surfactant
  • the method comprising: combining a lipid precursor and one or more additional components to form a precursor blend, wherein the one or more additional components comprise a co-surfactant, a co-solvent, or a combination thereof; and hydrolyzing the lipid precursor to form the carboxylate surfactant.
  • Also described herein are methods of displacing an unrefined petroleum material in contact with a solid material comprising: contacting the unrefined petroleum material with the compound described herein, a composition described herein, or a surfactant blend described herein, wherein the unrefined petroleum material is in contact with the solid material; and allowing the unrefined petroleum material to separate from the solid material, thereby displacing the unrefined petroleum material in contact with the solid material.
  • FIG. 1 shows a surface activity map for Lauric Acid, Na salt (0.25% Lauric acid Na salt/NaCl scan at 68 °C).
  • FIG. 2 shows phase behavior images for 2-ethyl hexanoate-Na shows no oil solubilization.
  • FIG. 5A and 5B show (5 A) phase behavior images and (5B) graph showing oil and water solubilization ratios for SP Formulation 17 (0.3 wt% cardphenol -5PO-5EO and 0.3 wt% C20:24IOS) at a temperature of 70C with an oil viscosity of 3.2 cp with NaCl.
  • FIG. 6 shows the composition for CNSL.
  • the terms “comprise” (as well as forms, derivatives, or variations thereof, such as “comprising” and “comprises”) and “include” (as well as forms, derivatives, or variations thereof, such as “including” and “includes”) are inclusive (i.e., open-ended) and do not exclude additional elements or steps.
  • the terms “comprise” and/or “comprising,” when used in this specification specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof.
  • a range of 10% to 20% can includes 10% and also includes 20%, and includes percentages in between 10% and 20%, unless explicitly stated otherwise herein. It is understood that when combinations, subsets, groups, etc. of elements are disclosed (e.g., combinations of components in a composition, or combinations of steps in a method), that while specific reference of each of the various individual and collective combinations and permutations of these elements may not be explicitly disclosed, each is specifically contemplated and described herein.
  • Ranges can be expressed herein as from “about” one particular value, and/or to “about” another particular value. By “about” is meant within 5% of the value, e.g., within 4, 3, 2, or 1 % of the value. When such a range is expressed, another aspect includes from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the particular value forms another aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are a number of values disclosed herein, and that each value is also herein disclosed as “about” that particular value in addition to the value itself. For example, if the value “10” is disclosed, then “about 10” is also disclosed.
  • the terms “may,” “optionally,” and “may optionally” are used interchangeably and are meant to include cases in which the condition occurs as well as cases in which the condition does not occur.
  • the statement that a formulation "may include an excipient” is meant to include cases in which the formulation includes an excipient as well as cases in which the formulation does not include an excipient.
  • contacting refers to materials or compounds being sufficiently close in proximity to react or interact.
  • the term “contacting” can include placing a compound (e.g., a surfactant) or an aqueous composition (e.g., chemical, surfactant or polymer) within a hydrocarbon material-bearing formation using any suitable manner known in the art (e.g., pumping, injecting, pouring, releasing, displacing, spotting or circulating the chemical into a well, well bore or hydrocarbon bearing formation).
  • Crude oils or “unrefined petroleums” generally refer to a mixture of naturally occurring hydrocarbons that may be refined into diesel, gasoline, heating oil, jet fuel, kerosene, and other products called fuels or petrochemicals. Crude oils or unrefined petroleums are named according to their contents and origins, and are classified according to their per unit weight (specific gravity). Heavier crudes generally yield more heat upon burning, but have lower gravity as defined by the American Petroleum Institute (API) (i.e., API gravity) and market price in comparison to light (or sweet) crude oils. Crude oil may also be characterized by its Equivalent Alkane Carbon Number (EACN).
  • API American Petroleum Institute
  • EACN Equivalent Alkane Carbon Number
  • nonactive oil refers to an oil that is not substantially reactive or crude oil not containing significant amounts of natural organic acidic components or their precursors such as esters or lactones such that significant amounts of soaps are generated when reacted with alkali.
  • a nonactive oil as referred to herein includes oils having an acid number of less than 0.5 mg KOH/g of oil.
  • water solubilization ratio is defined as the volume of water solubilized divided by the volume of surfactant in microemulsion. All the surfactant is presumed to be in the microemulsion phase. The water solubilization ratio is applied for Winsor type III and type II behavior. The volume of water solubilized is found by reading the change between initial aqueous level and excess water (bottom) interface level. The water solubilization parameter is calculated as follows: where o w is the water solubilization ratio, V w is the volume of oil solubilized, and V s is the volume of surfactant.
  • Viscosity refers to a fluid's internal resistance to flow or being deformed by shear or tensile stress. In other words, viscosity may be defined as thickness or internal friction of a liquid. Thus, water is “thin”, having a lower viscosity, while oil is “thick”, having a higher viscosity. More generally, the less viscous a fluid is, the greater its ease of fluidity.
  • interfacial tension refers to the surface tension between test oil and water of different salinities containing a surfactant formulation at different concentrations. Typically, interfacia] tensions are measured using a spinning drop tensiometer or calculated from phase behavior experiments.
  • contacting refers to materials or compounds being sufficiently close in proximity to react or interact.
  • the term “contacting” can include placing a compound (e.g., a surfactant) or an aqueous composition (e.g., chemical, surfactant or polymer) within a hydrocarbon-bearing formation using any suitable manner known in the art (e.g., pumping, injecting, pouring, releasing, displacing, spotting or circulating the chemical into a well, wellbore or hydrocarbon-bearing formation).
  • live oil refers generally to an oil containing dissolved gas (e.g., methane) in solution.
  • the term “substituted” is contemplated to include all permissible substituents of organic compounds.
  • the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and nonaromatic substituents of organic compounds.
  • Illustrative substituents include, for example, those described below.
  • the permissible substituents can be one or more and the same or different for appropriate organic compounds.
  • heteroatoms present in a compound or moiety, such as nitrogen can have hydrogen substituents and/or any permissible substituents of organic compounds described herein which satisfy the valency of the heteroatom.
  • substitution or “substituted with” include the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound (e.g., a compound that does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, etc.
  • Z 1 ,” “Z 2 ,” “Z 3 ,” and “Z 4 ” are used herein as generic symbols to represent various specific substituents. These symbols can be any substituent, not limited to those disclosed herein, and when they are defined to be certain substituents in one instance, they can, in another instance, be defined as some other substituents.
  • alkyl refers to saturated, straight-chained or branched saturated hydrocarbon moieties. Unless otherwise specified, C1-C24 (e.g., C1-C22, C1-C20, Ci- Cis, C1-C16, C1-C14, C1-C12, C1-C10, Ci-Cs, Ci-Ce, or C1-C4) alkyl groups are intended.
  • alkyl groups include methyl, ethyl, propyl, 1-methyl-ethyl, butyl, 1 -methylpropyl, 2-methyl -propyl, 1,1-dimethyl-ethyl, pentyl, 1-methyl-butyl, 2-methyl -butyl, 3- methyl-butyl, 2,2-dimethyl-propyl, 1-ethyl-propyl, hexyl, 1,1-dimethyl-propyl, 1 ,2-dimethyl- propyl, 1 -methyl -pentyl, 2-methyl-pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl- butyl, 1 ,2-dimethyl-butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl, 2,3-dimethyl-butyl, 3,3- dimethyl-butyl, 1-ethyl-butyl, 2-ethyl-butyl
  • Alkyl substituents may be unsubstituted or substituted with one or more chemical moieties.
  • the alkyl group can be substituted with one or more groups including, but not limited to, hydroxy, halogen, acyl, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiosulfonate (e.g., -SSCbRa), or thiol, as described below, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied.
  • the alkyl group can also include one or more heteroatoms (e.g., from one to three heteroatoms) incorporated within the hydrocarbon moiety.
  • heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus.
  • alkyl is generally used to refer to both unsubstituted alkyl groups and substituted alkyl groups; however, substituted alkyl groups are also specifically referred to herein by identifying the specific substituent(s) on the alkyl group.
  • halogenated alkyl specifically refers to an alkyl group that is substituted with one or more halides (halogens; e.g., fluorine, chlorine, bromine, or iodine).
  • alkoxyalkyl specifically refers to an alkyl group that is substituted with one or more alkoxy groups, as described below.
  • alkylamino specifically refers to an alkyl group that is substituted with one or more amino groups, as described below, and the like.
  • alkylthiol specifically refers to an alkyl group that is substituted with one or more thiol groups, as described below, and the like.
  • cycloalkyl refers to both unsubstituted and substituted cycloalkyl moieties
  • the substituted moieties can, in addition, be specifically identified herein; for example, a particular substituted cycloalkyl can be referred to as, e.g., an “alkylcycloalkyl.”
  • a substituted alkoxy can be specifically referred to as, e.g., a “halogenated alkoxy”
  • a particular substituted alkenyl can be, e.g., an “alkenylalcohol,” and the like.
  • the practice of using a general term, such as “cycloalkyl,” and a specific term, such as “alkylcycloalkyl,” is not meant to imply that the general term does not also include the specific term.
  • alkenyl refers to unsaturated, straight-chained, or branched hydrocarbon moieties containing a double bond.
  • C2-C24 e.g., C2- C22, C2-C20, C2-C18, C2-C16, C2-C14, C2-C12, C2-C10, C2-C8, C2-C6, C2-C4 alkenyl groups are intended.
  • Alkenyl groups may contain more than one unsaturated bond.
  • Examples include ethenyl, 1 -propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl - 1-propenyl, 2-methyl-l -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2- pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2-methyl- 1-butenyl, 3-methyl-l- butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2- methyl-3-butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethy 1-1 -propenyl, l,2-dimethyl-2-propenyl, 1 -
  • Alkenyl substituents may be unsubstituted or substituted with one or more chemical moieties.
  • suitable substituents include, for example, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiosulfonate (e.g., -SSC Ra), or thiol, as described below, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied.
  • alkynyl represents straight-chained or branched hydrocarbon moieties containing a triple bond.
  • C2-C24 e.g., C2- C22, C2-C20, C2-C1S, C2-C16, C2-C14, C2-C12, C2-C10, C 2 -Cs, C2-C6, C2-C4 alkynyl groups are intended.
  • Alkynyl groups may contain more than one unsaturated bond. Examples include C2-Ce-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl,
  • Alkynyl substituents may be unsubstituted or substituted with one or more chemical moieties.
  • suitable substituents include, for example, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, thiosulfonate (e.g., -SSChRa), or thiol, as described below.
  • aryl refers to groups that include a monovalent aromatic carbocyclic group of from 3 to 20 carbon atoms.
  • Aryl groups can include a single ring or multiple condensed rings.
  • aryl groups include Ce-Cio aryl groups. Examples of aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, tetrahydronaphthyl, phenylcyclopropyl, and indanyl.
  • the aryl group can be a phenyl, indanyl or naphthyl group.
  • heteroaryl is defined as a group that contains an aromatic group that has at least one heteroatom incorporated within the ring of the aromatic group.
  • heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus.
  • non- heteroaryl which is included in the term “aryl,” defines a group that contains an aromatic group that does not contain a heteroatom.
  • the aryl or heteroaryl substituents may be unsubstituted or substituted with one or more chemical moieties.
  • substituents include, for example, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, cycloalkyl, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, or thiol as described herein.
  • biasryl is a specific type of aryl group and is included in the definition of aryl. Biaryl refers to two aryl groups that are bound together via a fused ring structure, as in naphthalene, or are attached via one or more carbon-carbon bonds, as in biphenyl.
  • cycloalkyl as used herein is a non-aromatic carbon-based ring composed of at least three carbon atoms.
  • examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • heterocycloalkyl is a cycloalkyl group as defined above where at least one of the carbon atoms of the ring is substituted with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.
  • the cycloalkyl group and heterocycloalkyl group can be substituted or unsubstituted.
  • the cycloalkyl group and heterocycloalkyl group can be substituted with one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, or thiol as described herein.
  • cycloalkenyl as used herein is a non-aromatic carbon-based ring composed of at least three carbon atoms and containing at least one double bound, i.e., C-C.
  • cycloalkenyl groups include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, and the like.
  • heterocycloalkenyl is a type of cycloalkenyl group as defined above, and is included within the meaning of the term “cycloalkenyl,” where at least one of the carbon atoms of the ring is substituted with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.
  • the cycloalkenyl group and heterocycloalkenyl group can be substituted or unsubstituted.
  • the cycloalkenyl group and heterocycloalkenyl group can be substituted with one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, acyl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, or thiol as described herein.
  • cyclic group is used herein to refer to either aryl groups, non-aryl groups (z'.e., cycloalkyl, heterocycloalkyl, cycloalkenyl, and heterocycloalkenyl groups), or both. Cyclic groups have one or more ring systems that can be substituted or unsubstituted. A cyclic group can contain one or more aryl groups, one or more non-aryl groups, or one or more aryl groups and one or more non-aryl groups.
  • heteroaryl refers to a monocyclic or polycyclic aromatic heterocycle having at least one heteroatom ring member selected from sulfur, oxygen, and nitrogen.
  • the heteroaryl ring has 1, 2, 3, or 4 heteroatom ring members independently selected from nitrogen, sulfur and oxygen.
  • any ringforming N in a heteroaryl moiety can be an N-oxide.
  • the heteroaryl has 5-10 ring atoms and 1, 2, 3 or 4 heteroatom ring members independently selected from nitrogen, sulfur and oxygen.
  • the heteroaryl has 5-6 ring atoms and 1 or 2 heteroatom ring members independently selected from nitrogen, sulfur and oxygen.
  • Exemplary five-membered ring heteroaryls are thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, pyrazolyl, isothiazolyl, isoxazolyl, 1 ,2,3-triazoIyI, tetrazolyl, 1,2,3-thiadiazolyl, 1,2,3- oxadiazolyl, 1 ,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-triazolyl, 1,3,4- thiadiazolyl, and 1,3,4-oxadiazolyl.
  • a six-membered heteroaryl ring is a heteroaryl with a ring having six ring atoms wherein one or more (e.g., 1, 2, or 3) ring atoms are independently selected from N, O, and S.
  • Exemplary six-membered ring heteroaryls are pyridyl, pyrazinyl, pyrimidinyl, triazinyl and pyridazinyl.
  • Example heterocycloalkyl groups include pyrrolidin-2-one, l,3-isoxazolidin-2-one, pyranyl, tetrahydropuran, oxetanyl, azetidinyl, morpholino, thiomorpholino, piperazinyl, tetrahydrofuranyl, tetrahydro thienyl, piperidinyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, azepanyl, benzazapene, and the like.
  • Ring-forming carbon atoms and heteroatoms of a heterocycloalkyl group can be optionally substituted by oxo or sulfido (e.g., C(O), S(O), C(S), or S(O)2, etc.).
  • the heterocycloalkyl group can be attached through a ring-forming carbon atom or a ring-forming heteroatom.
  • the heterocycloalkyl group contains 0 to 3 double bonds. In some embodiments, the heterocycloalkyl group contains 0 to 2 double bonds.
  • heterocycloalkyl moieties that have one or more aromatic rings fused (z. ⁇ ?., having a bond in common with) to the cycloalkyl ring, for example, benzo or thienyl derivatives of piperidine, morpholine, azepine, etc.
  • a heterocycloalkyl group containing a fused aromatic ring can be attached through any ring-forming atom including a ring-forming atom of the fused aromatic ring.
  • the heterocycloalkyl has 4-10, 4-7 or 4-6 ring atoms with 1 or 2 heteroatoms independently selected from nitrogen, oxygen, or sulfur and having one or more oxidized ring members.
  • the definitions or embodiments refer to specific rings (e.g., an azetidine ring, a pyridine ring, etc.). Unless otherwise indicated, these rings can be attached to any ring member provided that the valency of the atom is not exceeded. For example, an azetidine ring may be attached at any position of the ring, whereas a pyridin-3-yl ring is attached at the 3-position.
  • acyl as used herein is represented by the formula -C(O)Z where Z 1 can be a hydrogen, hydroxyl, alkoxy, alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.
  • Z 1 can be a hydrogen, hydroxyl, alkoxy, alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.
  • acyl can be used interchangeably with “carbonyl.”
  • Examples include methoxy, ethoxy, propoxy, 1 -methyl-ethoxy, butoxy, 1 -methyl-propoxy, 2-methyl-propoxy, 1,1 -dimethyl-ethoxy, pentoxy, 1-methyl-butyloxy, 2-methyl-butoxy, 3-methyl-butoxy, 2,2-di-methyl-propoxy, 1- ethyl-propoxy, hexoxy, 1,1-dimethyl-propoxy, 1 ,2-dimethyl-propoxy, 1-methyl-pentoxy, 2- methyl-pentoxy, 3-methyl-pentoxy, 4-methyl-penoxy, 1,1-dimethyl-butoxy, 1 ,2-dimethyl- butoxy, 1,3-dimethyl-butoxy, 2,2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl- butoxy, 1-ethyl-butoxy, 2-ethylbutoxy, 1,1,2-trimethyl-propoxy, 1,2,2-trimethyl-propoxy, 1- ethyl-l-
  • aldehyde as used herein is represented by the formula — C(O)H.
  • amine or “amino” as used herein are represented by the formula — NZ'Z 2 , where Z 1 and Z 2 can each be substitution group as described herein, such as hydrogen, an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.
  • “Amido” is — C(O)NZ ] Z 2 .
  • carboxylic acid as used herein is represented by the formula — C(O)OH.
  • a “carboxylate” or “carboxyl” group as used herein is represented by the formula — C(O)O".
  • esters as used herein is represented by the formula — OC(O)Z ] or — C(O)OZ*, where Z 1 can be an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.
  • ether as used herein is represented by the formula Z'OZ 2 , where Z 1 and Z 2 can be, independently, an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.
  • ketone as used herein is represented by the formula Z’C(O)Z 2 , where Z 1 and Z 2 can be, independently, an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.
  • halide or “halogen” or “halo” as used herein refers to fluorine, chlorine, bromine, and iodine.
  • hydroxyl as used herein is represented by the formula — OH.
  • nitro as used herein is represented by the formula — NO2.
  • sil as used herein is represented by the formula — SiZ*Z 2 Z 3 , where Z 1 , Z 2 , and Z 3 can be, independently, hydrogen, alkyl, halogenated alkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.
  • sulfonyl is used herein to refer to the sulfo-oxo group represented by the formula — S(O)2Z ] , where Z 1 can be hydrogen, an alkyl, halogenated alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heterocycloalkenyl group described above.
  • sulfonylamino or “sulfonamide” as used herein is represented by the formula — S(O)2NH — .
  • Me refers to a methyl group
  • OMe refers to a methoxy group
  • z-Pr refers to an isopropyl group.
  • R 1 ,” “ 2,” “ 3,” “ R n ” etc , where n is some integer, as used herein can, independently, possess one or more of the groups listed above.
  • R 1 is a straight chain alkyl group
  • one of the hydrogen atoms of the alkyl group can optionally be substituted with a hydroxyl group, an alkoxy group, an amine group, an alkyl group, a halide, and the like.
  • a first group can be incorporated within second group or, alternatively, the first group can be pendant (i.e., attached) to the second group.
  • an alkyl group comprising an amino group the amino group can be incorporated within the backbone of the alkyl group.
  • the amino group can be attached to the backbone of the alkyl group.
  • the nature of the group(s) that is (are) selected will determine if the first group is embedded or attached to the second group.
  • Ra and Rb in this context can be the same or different and independently hydrogen, halogen hydroxyl, alkyl, alkoxy, alkyl, amino, alkylamino, dialkylamino, carbocyclyl, carbocycloalkyl, heterocarbocyclyl, heterocarbocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl.
  • a formula with chemical bonds shown only as solid lines and not as wedges or dashed lines contemplates each possible stereoisomer or mixture of stereoisomer (e.g., each enantiomer, each diastereomer, each meso compound, a racemic mixture, or scalemic mixture).
  • surfactant compounds can include derivatives of components of cashew nutshell liquid (CNSL), including derivatives of anacardiac acid, derivatives of cardanol, derivatives of cardol, and derivatives of 2- methylcardol.
  • CNSL cashew nutshell liquid
  • BO represents, individually for each occurrence, -CH2-CH(ethyl)-O- or - CHSCH(0-)CH3;
  • PO represents, individually for each occurrence, -CH2-CH(methyl)-O-;
  • EO represents, individually for each occurrence, -CH2-CH2-O-;
  • R 1 represents a C15 alkyl group or a C 15 alkenyl group;
  • R 2 represents hydrogen or methyl;
  • Q is hydrogen, -SO M + , - SO 3 H, CH 2 CH(OH)CH 2 -SO 3 M + , CH 2 CH(OH)CH2-SO 3 H, -CH 2 C(O)O M + , or - CH2C(0)0H;
  • M + when present, is a cation;
  • x is an integer from 0 to 15;
  • y is an integer from 0 to 50; and
  • z is an integer from 1 to 100.
  • x is an integer from 1 to 5, such as an integer from 1 to 3, from 1 to 4, from 2 to 4, from 2 to 5, from 3 to 4, or from 3 to 5. In other embodiments, x is 0.
  • y is an integer from 1 to 50, such as an integer from 1 to 40, from 1 to 30, from 1 to 20, from 1 to 10, from 5 to 40, from 5 to 30, from 5 to 20, from 5 to 10, from 10 to 40, from 10 to 30, or from 10 to 20. In some embodiments, y is 0.
  • x is an integer from 1 to 50, such as an integer from 1 to 40, from 1 to 30, from 1 to 20, from 1 to 10, from 5 to 40, from 5 to 30, from 5 to 20, from 5 to 10, from 10 to 40, from 10 to 30, or from 10 to 20.
  • R 2 is hydrogen. In other embodiments, R 2 is methyl.
  • Q is hydrogen. In other embodiments, Q is -SCENC, -SO3H, CH2CH(OH)CH 2 -SO 3 M + , CH 2 CH(OH)CH 2 -SO 3 H, -CH 2 C(O)O’M + , or -CH 2 C(O)OH. In other embodiments, Q is -SCENE. In other embodiments, Q is-SOiH. In other embodiments, Q is CH 2 CH(OH)CH2-SO 3 M + . In other embodiments, Q is CH 2 CH(OH)CH2-SO 3 H. In other embodiments, Q is -CH2C(O)O‘M + . In other embodiments, Q is -CH2C(O)OH.
  • R 1 represents a linear C15 alkyl group or a linear C15 alkenyl group. In some embodiments, R 1 represents a linear C15 alkyl group. In some embodiments, R 1 represents a linear C15 alkenyl group.
  • R 1 is represented by the structure below
  • R 1 is a linear C15 monoene, a linear C15 diene, or a linear C15 triene. In some embodiments, R 1 is a linear C15 monoene. In some embodiments, R 1 is a linear C15 diene. In some embodiments, R 1 is a linear C15 triene. In some embodiments, R 1 is represented by the structure below j n some embodiments, R 1 is represented by the structure below [ n some embodiments, R 1 is represented by the structure below
  • BO represents -CH2-CH(ethyl)-O- or -CH 3 CH(O-)CH 3 ;
  • PO represents -CH2- CH(methyl)-O-;
  • EO represents -CH2-CH2-O-;
  • R 1 represents a C15 alkyl group or a C 15 alkenyl group;
  • Q is hydrogen, -SO 3 M + , -SO3H, CH 2 CH(OH)CH 2 -SO 3 M + , CH 2 CH(OH)CH 2 - SO 3 H, -CH2C(O)O’M + , or -CH2C(O)OH;
  • M + when present, is a cation;
  • x is an integer from 0 to 15;
  • y is an integer from 0 to 50; and
  • z is an integer from 1 to 100.
  • x is an integer from 1 to 5, such as an integer from 1 to 3, from 1 to 4, from 2 to 4, from 2 to 5, from 3 to 4, or from 3 to 5. In other embodiments, x is 0.
  • y is an integer from 1 to 50, such as an integer from 1 to 40, from 1 to 30, from 1 to 20, from 1 to 10, from 5 to 40, from 5 to 30, from 5 to 20, from 5 to 10, from 10 to 40, from 10 to 30, or from 10 to 20. In some embodiments, y is 0.
  • x is an integer from 1 to 50, such as an integer from 1 to 40, from 1 to 30, from 1 to 20, from 1 to 10, from 5 to 40, from 5 to 30, from 5 to 20, from 5 to 10, from 10 to 40, from 10 to 30, or from 10 to 20.
  • Q is hydrogen. In other embodiments, Q is -SO 3 M + , -SO 3 H, CH 2 CH(OH)CH 2 -SO 3 M + , CH 2 CH(OH)CH 2 -SO 3 H, -CH 2 C(O)O’M + , or -CH 2 C(O)OH. In other embodiments, Q is -SO 3 M + . In other embodiments, Q is-SO 3 H. In other embodiments, Q is CH 2 CH(OH)CH 2 -SO 3 M + . In other embodiments, Q is CH 2 CH(OH)CH 2 -SO 3 H. In other embodiments, Q is -CH 2 C(O)O M . In other embodiments, Q is -CH 2 C(O)OH.
  • R 1 represents a linear C15 alkyl group or a linear C15 alkenyl group. In some embodiments, R 1 represents a linear C15 alkyl group. In some embodiments, R 1 represents a linear C15 alkenyl group.
  • R 1 is a linear C15 monoene, a linear C15 diene, or a linear C15 triene. In some embodiments, R 1 is a linear C15 monoene. In some embodiments, R 1 is a linear C15 diene. In some embodiments, R 1 is a linear C15 triene. In some embodiments, R 1 is represented by the structure below j n some embodiments, R 1 is represented by the structure below . In some embodiments, R 1 is represented by the structure below
  • Formula III or a salt thereof wherein BO represents -CH 2 -CH(ethyl)-O- or -CH 3 CH(O-)CH 3 ; PO represents -CH 2 -CH(methyl)-O-; EO represents -CH 2 -CH 2 -O-; R 1 represents a C15 alkyl group or a C 15 alkenyl group; R 3 represents hydrogen, an alkyl group, an alkoxy group, an aryl group, or an alkyleneoxy group; Q is hydrogen, -SO 3 M + , -SO 3 H, CH 2 CH(OH)CH 2 - SO 3 M + , CH 2 CH(OH)CH 2 -SO 3 H, -CH 2 C(O)O M + , or -CH 2 C(O)OH; M + , when present, is a cation; x is an integer from 0 to 15; y is an integer from 0 to 50; and z is an integer from 1 to 100.
  • R 1 represents a linear C15 alkyl group or a linear C15 alkenyl group. In some embodiments, R 1 represents a linear C15 alkyl group. In some embodiments, R 1 represents a linear C15 alkenyl group.
  • R 1 is represented by the structure below
  • the carboxylic acid surfactant can include caprylate, pelargonate, caprate, undecylate, laurate, tridecylate, myristate, myristoleate, pentadecylate, palmitate, palmitoleate, sapienate, margarate, stearate, oleate, elaidate, vaccenate, linoleate, linoelaidate, a-linolenate, y-linolenate, stearidonate, nonadecylate, arachidate, eicosenoate, dihomo-y- linolenate, meadate, arachidonate, eicosapentaenoate, heneicosylate, behenate, erucate, docosahexaenoate, tricosylate, lignocerate, nervonate, pentacosylate, cerotate, heptacosylate,
  • the carboxylic acid surfactant can include a compound of Formula IV:
  • the carboxylic acid surfactant can be derived from cashew nut shell liquid.
  • R 1 can represent a linear C15 alkyl group or a linear C15 alkenyl group. In some aspects, R 1 can represent a linear C15 alkyl group. In some aspects, R 1 can represent a linear C15 alkenyl group. In some such aspects, R 1 can be represented by the structure
  • R 1 can be a linear C15 monoene, a linear C15 diene, or a linear C15 triene. In some embodiments, R 1 can be a linear C15 monoene. In some embodiments, R 1 can be a linear C15 diene. In some aspects, R 1 can be a linear C15 triene. In some embodiments, R 1 can be represented by the structure ome embodiments, R 1 can be represented by t In some embodiments, R 1 can be represented by the structure
  • the carboxylic acid surfactant can include a compound of Formula V :
  • the carboxylic acid surfactant can be produced by the Guerbet reaction.
  • the carboxylic acid surfactant can include 2-butyl-octanoic acid, 2-hexyl-decanoic acid, 2-decyl-tetradecanoic acid, 2-tetradecyl-octadecanoic acid, or any combination thereof.
  • the carboxylic acid surfactant can include another oxidized Guerbet alcohol.
  • aqueous compositions that include a compound described herein (e.g., a compound of Formula I, Formula II, and/or Formula III).
  • aqueous compositions that comprise a compound described herein (e.g., a compound of Formula I, Formula II, and/or Formula III) and water.
  • aqueous compositions that include anacardiac acid or a salt thereof.
  • aqueous compositions that include anacardiac acid or a salt thereof and water.
  • carboxylic acid surfactants described herein are also provided are carboxylic acid surfactants described herein and water.
  • Additional components including polymers (e.g., viscosity-enhancing water-soluble polymers), alkali agents, additional surfactants, cosolvents, or any combination thereof, can be present in the aqueous compositions.
  • the aqueous composition can further include an additional surfactant.
  • a surfactant as used herein, is a compound within the aqueous composition that functions as a surface- ctive agent when the aqueous composition is in contact with a crude oil (e.g., an unrefined petroleum). The surfactant can act to lower the interfacial tension and/or surface tension of the unrefined petroleum.
  • the surfactant and the compound of Formula I are present in synergistic surface-active amounts.
  • a “synergistic surface active amount,” as used herein, means that a compound of Formula I and the surfactant are present in amounts in which the oil surface activity (interfacial tension lowering effect and/or surface tension lowering effect on crude oil when the aqueous composition is added to the crude oil) of the compound and surfactant combined is greater than the additive oil surface activity of the surfactant individually and the compound individually.
  • the oil surface activity of the compound and surfactant combination is 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% or 100% more than the additive oil surface activity of the surfactant individually and the compound individually.
  • the oil surface activity of the compound and surfactant combination is 2, 3, 4, 5, 6, 7, 8, 9 or 10 times more than the additive oil surface activity of the surfactant individually and the compound individually.
  • the compound and surfactant are present in a surfactant stabilizing amount.
  • a “surfactant stabilizing amount” means that the compound and the surfactant are present in an amount in which the surfactant degrades at a slower rate in the presence of the compound than in the absence of the compound, and/or the compound degrades at a slower rate in the presence of the surfactant than in the absence of the surfactant.
  • the rate of degradation may be 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% or 100% slower. In some embodiments, the rate of degradation is 2, 3, 4, 5, 6, 7, 8, 9 or 10 times slower.
  • the compound and surfactant are present in a synergistic solubilizing amount.
  • a “synergistic solubilizing amount” means that the compound and the surfactant are present in an amount in which the compound is more soluble in the presence of the surfactant than in the absence of the surfactant, and/or the surfactant is more soluble in the presence of the compound than in the absence of the compound.
  • the solubilization may be 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% or 100% higher. In some embodiment, the solubilization is 2, 3, 4, 5, 6, 7, 8, 9 or 10 times higher.
  • the compound is present in an amount sufficient to increase the solubility of the surfactant in the aqueous composition relative to the absence of the compound. In other words, in the presence of a sufficient amount of the compound, the solubility of the surfactant in the aqueous composition is higher than in the absence of the compound. In other embodiments, the surfactant is present in an amount sufficient to increase the solubility of the compound in the aqueous composition relative to the absence of the surfactant. Thus, in the presence of a sufficient amount of the surfactant the solubility of the compound in the aqueous solution is higher than in the absence of the surfactant.
  • a single type of surfactant is in the aqueous composition.
  • a surfactant can comprise a blend of surfactants (e.g., a combination of two or more surfactants).
  • the surfactant blend can comprise a mixture of a plurality of surfactant types.
  • the surfactant blend can include at least two surfactant types, at least three surfactant types, at least four surfactant types, at least five surfactant types, at least six surfactant types, or more.
  • the surfactant blend can include from two to six surfactant types (e.g., from two to five surfactant types, from two to four surfactant types, from two to three surfactant types, from three to six surfactant types, or from three to five surfactant types).
  • the surfactant types can be independently different (e.g., anionic or cationic surfactants; two anionic surfactants having a different hydrocarbon chain length but are otherwise the same; a sulfate and a sulfonate surfactant that that the same hydrocarbon chain length and are otherwise the same, etc.). Therefore, a person having ordinary skill in the art will immediately recognize that the terms "surfactant” and "surfactant type(s)" have the same meaning and can be used interchangeably.
  • the surfactant can comprise an anionic surfactant, a non-ionic surfactant, a zwitterionic surfactant, a cationic surfactant, or a combination thereof.
  • the surfactant can comprise an anionic surfactant, a non-ionic surfactant, or a combination thereof.
  • the surfactant can comprise a plurality of anionic surfactants.
  • the surfactant can comprise a zwitterionic surfactant.
  • "Zwitterionic" or “zwitterion” as used herein refers to a neutral molecule with a positive (or cationic) and a negative (or anionic) electrical charge at different locations within the same molecule. Examples of zwitterionic surfactants include without limitation betains and sultains.
  • the surfactant can be any appropriate surfactant useful in the field of enhanced oil recovery.
  • the surfactant can comprise an internal olefin sulfonate (IOS), an alpha olefin sulfonate (AOS), an alkyl aryl sulfonate (ARS), an alkyl benzene sulfonate (ABS)an alkane sulfonate, a petroleum sulfonate, an alkyl diphenyl oxide (di)sulfonate, an alcohol sulfate, an alkoxy sulfate, an alkoxy sulfonate, an alcohol phosphate, an alkoxy phosphate, a sulfosuccinate ester, an alcohol ethoxylate, an alkyl phenol ethoxylate, a quaternary ammonium salt, a betaine or sultaine.
  • the surfactant as provided herein, can also be a soap
  • the surfactant can comprise an anionic surfactant.
  • the surfactant can comprise an anionic surfactant selected from the group consisting of alkoxy carboxylate surfactants, alkoxy sulfate surfactants, alkoxy sulfonate surfactants, alkyl sulfonate surfactants, aryl sulfonate surfactants, olefin sulfonate surfactants, and combinations thereof.
  • the anionic surfactant can comprise an anionic surfactant blend. Where the anionic surfactant is an anionic surfactant blend, the aqueous composition includes a plurality (i.e., more than one) type of anionic surfactant.
  • Suitable surfactants are disclosed, for example, in U.S. Patent Nos. 3,811,504, 3,811,505, 3,811,507, 3,890,239, 4,463,806, 6,022,843, 6,225,267, and 7,629,299; International Patent Application Publication Nos. WO/2008/079855, WO/2012/027757, WO/2017/145164, and WO /2011/094442; as well as U.S. Patent Application Publication Nos. 2005/0199395, 2006/0185845, 2006/018486, 2009/0270281, 2011/0046024, 2011/0100402, 2011/0190175, 2007/0191633, 2010/004843.
  • Additional suitable surfactants are surfactants known to be used in enhanced oil recovery methods, including those discussed in D. B. Levitt, A. C. Jackson, L. Britton and G. A. Pope, "Identification and Evaluation of High-Performance EOR Surfactants," SPE 1X89, conference contribution for the SPE Symposium on Improved Oil Recovery Annual Meeting, Tulsa, Okla., Apr. 24-26, 2006.
  • surfactants are commercially available as blends of related molecules (e.g., IOS and ABS surfactants).
  • a surfactant is present within a composition provided herein, a person of ordinary skill would understand that the surfactant might be a blend of a plurality of related surfactant molecules (as described herein and as generally known in the art).
  • the total surfactant concentration in the aqueous composition is of 10% w/w or less (e.g., 7.5% w/w or less, 5% w/w or less, 2.5% w/w or less, 1% w/w or less, or 0.5% w/w or less). In some embodiments, the total surfactant concentration in the aqueous composition is of at least 0.1% w/w (e.g., at least 7.5% w/w, at least 5% w/w, at least 2.5% w/w, at least 1% w/w, or at least 0.5% w/w,
  • the total surfactant concentration in the aqueous composition can be present in an amount ranging from any of the minimum values described above to any of the maximum values described above.
  • the total surfactant concentration in the aqueous composition is from 0.05% w/w to 10% w/w (e.g., from 0.05% w/w to 7.5% w/w, from 0.05% w/w to 5% w/w, from 0.05% w/w to 2.5% w/w from 0.05% w/w to 1% w/w, from 0.05% w/w to 0.5% w/w, from 0.05% w/w to 0.1% w/w, from 0.1% w/w to 10% w/w, from 0.1% w/w to 7.5% w/w, from 0.1% w/w to 5% w/w, from 0.1% w/w to 2.5% w/w from 0.1% w/w to 1% w/w, from 0.1% w/w/w, from 0.
  • the total surfactant concentration in the aqueous composition is 0.5% w/w, 1.0% w/w, 1.25% w/w, 1.5% w/w, 1.75% w/w, 2.0% w/w, 2.5% w/w, 3.0% w/w, 3.5% w/w, 4.0% w/w, 4.5% w/w, 5.0% w/w, 5.5% w/w, 6.0% w/w, 6.5% w/w, 7.0% w/w, 7.5% w/w, 8.0% w/w, 9.0% w/w, or 10% w/w.
  • the carboxylic acid surfactant can be present in the aqueous composition in an amount of at least 0.5% (e.g., at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 1.25%, at least 1.5%, at least 1.75%, at least 2%, at least 2.25%, at least 2.5%, at least 2.75%, at least 3%, at least 3.25%, at least 3.5%, at least 3.75%, at least 4%, at least 4.25%, at least 4.5%, at least 4.75%, at least 5%) by weight.
  • at least 0.5% e.g., at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 1.25%, at least 1.5%, at least 1.75%, at least 2%, at least 2.25%, at least 2.5%, at least 2.75%, at least 3%, at least 3.25%, at least 3.5%, at least 3.75%, at least 4%, at least
  • the carboxylate surfactant can be present in the aqueous composition in an amount of up to 5% (e.g., up to 4.75%, up to 4.5%, up to 4.25%, up to 4%, up to 3.75%, up to 3.5%, up to 3.25%, up to 3%, up to 2.75%, up to 2.5%, up to 2.25%, up to 2%, up to 1 .75%, up to 1.5%, up to 1.25%, up to 1%, up to 0.9%, up to 0.8%, up to 0.7%, up to 0.6%, up to 0.5%) by weight.
  • up to 5% e.g., up to 4.75%, up to 4.5%, up to 4.25%, up to 4%, up to 3.75%, up to 3.5%, up to 3.25%, up to 3%, up to 2.75%, up to 2.5%, up to 2.25%, up to 2%, up to 1 .75%, up to 1.5%, up to 1.25%, up to 1%, up to 0.
  • the carboxylic acid surfactant can be present in the aqueous composition in an amount ranging from any of the minimum values described above to any of the maximum values described above.
  • the carboxylic acid surfactant can be present in the aqueous composition in an amount of from 0.5% to 5% (e.g., from 0.6% to 4.75%, from 0.7% to 4.5%, from 0.8% to 4.25%, from 0.9% to 4%, from 1% to 3.75%, from 1.25% to 3.5%, from 1.5% to 3.25%, from 1.75% to 3%, from 2% to 2.75%, from 2.25% to 2.5%, from 0.5% to 2.5%, from 0.6% to 2.25%, from 0.7% to 2%, from 0.8% to 1.75%, from 0.9% to 1.5%, from 1% to 1.25%, from 2.25% to 5%, from 2.5% to 4.75%, from 2.75% to 4.5%, from 3% to 4.25%, from 3.25% to 4%, from 3.5% to 3.75%) by weight.
  • the aqueous compositions can further include a viscosity enhancing water-soluble polymer.
  • the water-soluble polymer may be a biopolymer such as xanthan gum or scleroglucan, a synthetic polymer such as polyacryamide, hydrolyzed polyarcrylamide or co-polymers of acrylamide and acrylic acid, 2-acrylamido 2- methyl propane sulfonate or N-vinyl pyrrolidone, a synthetic polymer such as polyethylene oxide, or any other high molecular weight polymer soluble in water or brine.
  • the polymer is polyacrylamide (PAM), partially hydrolyzed polyacrylamides (HP AM), and copolymers of 2-acrylamido-2-methylpropane sulfonic acid or sodium salt or mixtures thereof, and polyacrylamide (PAM) commonly referred to as AMPS copolymer and mixtures of the copolymers thereof.
  • PAM polyacrylamide
  • the viscosity enhancing water- soluble polymer is polyacrylamide or a co-polymer of polyacrylamide.
  • the viscosity enhancing water-soluble polymer is a partially (e.g. 20%, 25%, 30%, 35%, 40%, 45%) hydrolyzed anionic polyacrylamide.
  • the viscosity enhancing water-soluble polymer has a molecular weight of approximately about 8xl0 6 Daltons. In some other further embodiment, the viscosity enhancing water-soluble polymer has a molecular weight of approximately about 18xl0 6 Daltons.
  • Non- limiting examples of commercially available polymers useful for the invention including embodiments provided herein are Florpaam 3330S and Florpaam 3360S. Molecular weights of the polymers may range from about 10,000 Daltons to about 20,000,000 Daltons.
  • the viscosity enhancing water-soluble polymer is used in the range of about 500 to about 5000 ppm concentration, such as from about 1000 to 2000 ppm (e.g., in order to match or exceed the reservoir oil viscosity under the reservoir conditions of temperature and pressure).
  • the aqueous compositions can further include an alkali agent.
  • An alkali agent as provided herein can be a basic, ionic salt of an alkali metal (e.g., lithium, sodium, potassium) or alkaline earth metal element (e.g., magnesium, calcium, barium, radium).
  • suitable alkali agents include, for example, NaOH, KOH, LiOH, Na2CO , NaHCOs, Na-metaborate, Na silicate, Na orthosilicate, Na acetate or NH4OH.
  • the aqueous composition includes hard brine water or soft brine water.
  • the water is soft brine water.
  • the water is hard brine water.
  • the aqueous composition can further include an alkaline agent.
  • the alkaline agent can provide for enhanced soap generation from the active oils, lower surfactant adsorption to the solid material (e.g., rock) in the reservoir and increased solubility of viscosity enhancing water soluble polymers.
  • the aqueous composition may include seawater, or fresh water from an aquifer, river or lake.
  • the alkali agent can be present in the aqueous composition at a concentration from 0.1% w/w to 10% w/w.
  • the combined amount of alkali agent and compound provided herein (e.g., compound of Formula I) present in the aqueous composition provided herein can be approximately equal to or less than 10% w/w.
  • the total concentration of alkali agent i.e., the total amount of alkali agent within the aqueous compositions and emulsion compositions provided herein
  • the total alkali agent concentration in the aqueous composition is from 0.25% w/w to 5% w/w.
  • the total alkali agent concentration in the aqueous composition is 0.5% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 0.75% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 1% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 1.25% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 1.50% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 1.75% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 2% w/w.
  • the total alkali agent concentration in the aqueous composition is 2.25% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 2.5% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 2.75% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 3% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 3.25% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 3.5% w/w.
  • the total alkali agent concentration in the aqueous composition is 3.75% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 4% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 4.25% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 4.5% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 4.75% w/w. In other embodiments, the total alkali agent concentration in the aqueous composition is 5.0% w/w. In some embodiments, the alkali agent can be present in the aqueous compositions in an effective amount to afford an aqueous composition having a pH of from 10 to 12 (e.g., 10.5 to 11.5).
  • the aqueous compositions can further include a co-solvent.
  • the co-solvent is an alcohol, alcohol ethoxylate, glycol ether, glycols, or glycerol.
  • the aqueous compositions provided herein may include more than one co-solvent.
  • the aqueous composition includes a plurality of different co-solvents. Where the aqueous composition includes a plurality of different co-solvents, the different cosolvents can be distinguished by their chemical (structural) properties.
  • the aqueous composition may include a first co-solvent, a second co-solvent and a third cosolvent, wherein the first co-solvent is chemically different from the second and the third cosolvent, and the second co-solvent is chemically different from the third co-solvent.
  • the plurality of different co-solvents includes at least two different alcohols (e.g., a Ci-Ce alcohol and a C1-C4 alcohol).
  • the aqueous composition includes a Ci-Ce alcohol and a C1-C4 alcohol.
  • the plurality of different cosolvents includes at least two different alkoxy alcohols (e.g., a Ci-Ce alkoxy alcohol and a Ci- C4 alkoxy alcohol).
  • the aqueous composition includes a Ci-Ce alkoxy alcohol and a C1-C4 alkoxy alcohol.
  • the plurality of different cosolvents includes at least two co-solvents selected from the group consisting of alcohols, alkyl alkoxy alcohols and phenyl alkoxy alcohols.
  • the plurality of different co- solvents may include an alcohol and an alkyl alkoxy alcohol, an alcohol and a phenyl alkoxy alcohol, or an alcohol, an alkyl alkoxy alcohol and a phenyl alkoxy alcohol.
  • the alkyl alkoxy alcohols or phenyl alkoxy alcohols provided herein have a hydrophobic portion (alkyl or aryl chain), a hydrophilic portion (e.g., an alcohol) and optionally an alkoxy (ethoxylate or propoxylate) portion.
  • the co-solvent is an alcohol, alkoxy alcohol, glycol ether, glycol or glycerol.
  • Suitable co-sol vents are known in the art, and include, for example, co-solvents described in U.S. Patent Application Publication No. 2013/0281327 which is hereby incorporated herein in its entirety
  • a co-solvent can be present in an amount sufficient to increase the solubility of the surfactants in the aqueous phase relative to the absence of the co-solvent. In other words, in the presence of a sufficient amount of the co-solvent, the solubility of the co-solvent in the aqueous phase is higher than in the absence of the co-solvent. In embodiments, the co-solvent can be present in an amount sufficient to increase the solubility of the surfactant in the aqueous phase relative to the absence of the co-solvent. Thus, in the presence of a sufficient amount of the co-solvent the solubility of the surfactant in the aqueous phase can be higher than in the absence of the co-solvent. In embodiments, the cosolvent can be present in an amount sufficient to decrease the viscosity of an emulsion formed from the composition relative to the absence of the co-solvent.
  • the aqueous composition can be substantially free of cosolvents (e.g., the composition can include less than 0.05% by weight additional co-solvents, based on the total weight of the composition).
  • the aqueous composition can have a pH of at least 7 (e.g., a pH of at least 7.5, a pH of at least 8, a pH of at least 8.5, a pH of at least 9, a pH of at least 9.5, a pH of at least 10, a pH of at least 10.5, a pH of at least 11 , a pH of at least 11.5, or a pH of at least 12.5).
  • a pH of at least 7 e.g., a pH of at least 7.5, a pH of at least 8, a pH of at least 8.5, a pH of at least 9, a pH of at least 9.5, a pH of at least 10, a pH of at least 10.5, a pH of at least 11 , a pH of at least 11.5, or a pH of at least 12.5.
  • the aqueous composition can have a pH of 13 or less (e.g., a pH of 12.5 or less, a pH of 12 or less, a pH of 11.5 or less, a pH of 11 or less, a pH of 10.5 or less, a pH of 10 or less, a pH of 9.5 or less, a pH of 9 or less, a pH of 8.5 or less, a pH of 8 or less, or a pH of 7.5 or less).
  • a pH of 13 or less e.g., a pH of 12.5 or less, a pH of 12 or less, a pH of 11.5 or less, a pH of 11 or less, a pH of 10.5 or less, a pH of 10 or less, a pH of 9.5 or less, a pH of 9 or less, a pH of 8.5 or less, a pH of 8 or less, or a pH of 7.5 or less.
  • the aqueous composition can have a pH ranging from any of the minimum values described above to any of the maximum values described above.
  • the aqueous composition can have a pH of from 7 to 13 (e.g., from 10 to 12, or from 10.5 to 11.5).
  • the aqueous composition can have a salinity of at least 100 ppm, (e.g., at least 500 ppm, at least 1,000 ppm, at least 5,000 ppm, at least 10,000 ppm, at least 50,000 ppm, at least 100,000 ppm, or at least 250,000 ppm). In some embodiments, the aqueous composition can have a salinity of 260,000 ppm or less, (e.g., 500 ppm or less, 1,000 ppm or less, 5,000 ppm or less, 10,000 ppm or less, 50,000 ppm or less, 100,000 ppm or less, or 250,000 ppm or less).
  • the aqueous composition can have a salinity of ranging from any of the minimum values described above to any of the maximum values described above.
  • the aqueous composition can have a salinity of from 100 ppm to 260,000 ppm (e.g., from 100 ppm to 250,000 ppm, from 100 ppm to 225,000 ppm, from 100 ppm to 200,000 ppm, from 100 ppm to 150,000 ppm, from 100 ppm to 100,000 ppm, from 100 ppm to 50,000 ppm, from 100 ppm to 10,000 ppm, from 100 ppm to 5,000 ppm, from 100 ppm to 1,000 ppm, from 100 ppm to 500 ppm, from 1000 ppm to 250,000 ppm, from 1000 ppm to 225,000 ppm, from 1000 ppm to 200,000 ppm, from 1000 ppm to 150,000 ppm, from 1000 ppm to 100,000 ppm, from 1000 ppm to 50,000 ppm, from
  • the aqueous composition can have a viscosity of between 20 mPas and 100 mPas at 20°C.
  • the viscosity of the aqueous solution may be increased from 0.3 mPas to 1, 2, 10, 20, 100 or even 1000 mPas by including a water-soluble polymer.
  • emulsions comprising a compound described herein or an aqueous composition described herein and unrefined petroleum.
  • the emulsion composition can be a microemulsion.
  • a "microemulsion” as referred to herein is a thermodynamically stable mixture of oil, water and surfactants that may also include additional components such as co-solvents, electrolytes, alkali and polymers.
  • a "macroemulsion” as referred to herein is a thermodynamically unstable mixture of oil and water that may also include additional components.
  • the emulsion composition provided herein may be an oil-in-water emulsion, wherein a surfactant forms aggregates (e.g., micelles) where the hydrophilic part of the surfactant molecule(s) contacts the aqueous phase of the emulsion and the lipophilic part contacts the oil phase of the emulsion.
  • a surfactant forms aggregates (e.g., micelles) where the hydrophilic part of the surfactant molecule(s) contacts the aqueous phase of the emulsion and the lipophilic part contacts the oil phase of the emulsion.
  • the surfactant(s) form part of the aqueous part of the emulsion.
  • the surfactant(s) form part of the oil phase of the emulsion.
  • the surfactant(s) form part of an interface between the aqueous phase and the oil phase of the emulsion.
  • the change in the solubilization ratios are less than 5%, 10%, 20%, 30%, 40%, or 50% over a divalent metal cation concentration range of 10 ppm, 100 ppm, 1000 ppm or 10,000 ppm. In another embodiment, the change in the solubilization ratios are less than 5%, 10%, 20%, 30%, 40%, or 50% over a salinity concentration range of 10 ppm, 100 ppm, 1000 ppm or 10,000 ppm.
  • polymers derived from condensation of an alcohol and an aldehyde wherein the alcohol comprises a compound defined by Formula IV
  • BO represents -CH2-CH(ethyl)-O- or -CH3CH(O-)CH3;
  • PO represents -CH2- CH(methyl)-O-;
  • EO represents -CH2-CH2-O-;
  • R 1 represents a C15 alkyl group or a C 15 alkenyl group;
  • Q is hydrogen;
  • x is an integer from 0 to 15;
  • y is an integer from 0 to 50; and
  • z is an integer from 0 to 100.
  • the aldehyde comprises formaldehyde.
  • x is an integer from 1 to 5. In other embodiments, x is 0. In some embodiments, y is 0. In other embodiments, y is an integer from 1 to 50, such as an integer from 1 to 40, from 1 to 30, from 1 to 20, from 1 to 10, from 5 to 40, from 5 to 30, from 5 to 20, from 5 to 10, from 10 to 40, from 10 to 30, or from 10 to 20.
  • R 1 represents a linear C15 alkyl group or a linear C15 alkenyl group. In some embodiments, R 1 is represented by the structure below
  • R 1 is a linear C15 monoene, a linear C15 diene, or a linear C15 triene. In some embodiments, R 1 is represented by the structure below m e embodiments, R 1 is represented by the . in some embodiments, R 1 is represented by the structure below
  • the alcohol comprises cardanol.
  • these polymers can be used in an oil and gas operation, such as an enhanced oil recovery operation.
  • these polymers can be used an emulsion breaker.
  • surfactant blends including a carboxylic acid surfactant and one or more additional components.
  • the carboxylic acid surfactant can include at least one unsaturated fatty acid salt. In other aspects, the carboxylic acid surfactant can include at least one saturated fatty acid salt. In yet other aspects, the carboxylic acid surfactant can include at least one unsaturated fatty acid salt and at least one saturated fatty acid salt. In some aspects, the carboxylic acid surfactant can include at least one branched fatty acid salt.
  • the carboxylic acid surfactant can include caprylate, pelargonate, caprate, undecylate, laurate, tridecylate, myristate, myristoleate, pentadecylate, palmitate, palmitoleate, sapienate, margarate, stearate, oleate, elaidate, vaccenate, linoleate, linoelaidate, a-linolenate, y-linolenate, stearidonate, nonadecylate, arachidate, eicosenoate, dihomo-y- linolenate, meadate, arachidonate, eicosapentaenoate, heneicosylate, behenate, erucate, docosahexaenoate, tricosylate, lignocerate, nervonate, pentacosylate, cerotate, heptacosylate,
  • the carboxylic acid surfactant can include a compound of Formula
  • R 1 can represent a Cis alkyl group or a Cis alkenyl group.
  • the carboxylic acid surfactant can be derived from cashew nut shell liquid.
  • R 1 can represent a linear Cis alkyl group or a linear Cis alkenyl group. In some aspects, R 1 can represent a linear Cis alkyl group. In some aspects, R 1 can represent a linear Cis alkenyl group. In some such aspects, R 1 can be represented by the structure
  • R 1 can be a linear Cis monoene, a linear Cis diene, or a linear Cis triene. In some aspects, R 1 can be a linear Cis monoene. In some aspects, R 1 can be a linear Cis diene. In some aspects, R 1 can be a linear Cis triene. represented by the structure
  • R 1 can be represented by the s . In yet other such aspects, R 1 can be represented by the structure
  • the carboxylic acid surfactant can include a compound of Formula V:
  • each of R 2 and R 3 can independently represent a C4-C20 alkyl group or a C4-C20 alkenyl group.
  • the carboxylic acid surfactant can be produced by the Guerbet reaction.
  • the carboxylic acid surfactant can include 2-butyl-octanoic acid, 2- hexyl-decanoic acid, 2-decyl-tetradecanoic acid, 2-tetradecyl-octadecanoic acid, or any combination thereof.
  • the carboxylic acid surfactant can include another oxidized Guerbet alcohol.
  • the carboxylic acid surfactant can be present in an amount of at least 0.5% (e.g., at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 1.25%, at least 1.5%, at least 1.75%, at least 2%, at least 2.25%, at least 2.5%, at least 2.75%, at least 3%, at least 3.25%, at least 3.5%, at least 3.75%, at least 4%, at least 4.25%, at least 4.5%, at least 4.75%, at least 5%) by weight.
  • at least 0.5% e.g., at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 1.25%, at least 1.5%, at least 1.75%, at least 2%, at least 2.25%, at least 2.5%, at least 2.75%, at least 3%, at least 3.25%, at least 3.5%, at least 3.75%, at least 4%, at least 4.25%, at least 4.
  • the carboxylate surfactant can be present in an amount of up to 5% (e.g., up to 4.75%, up to 4.5%, up to 4.25%, up to 4%, up to 3.75%, up to 3.5%, up to 3.25%, up to 3%, up to 2.75%, up to 2.5%, up to 2.25%, up to 2%, up to 1.75%, up to 1.5%, up to 1.25%, up to 1 %, up to 0.9%, up to 0.8%, up to 0.7%, up to 0.6%, up to 0.5%) by weight.
  • up to 5% e.g., up to 4.75%, up to 4.5%, up to 4.25%, up to 4%, up to 3.75%, up to 3.5%, up to 3.25%, up to 3%, up to 2.75%, up to 2.5%, up to 2.25%, up to 2%, up to 1.75%, up to 1.5%, up to 1.25%, up to 1 %, up to 0.9%, up to 0.8%, up
  • the carboxylic acid surfactant can be present in an amount ranging from any of the minimum values described above to any of the maximum values described above.
  • the carboxylic acid surfactant can be present in an amount of from 0.5% to 5% (e.g., from 0.6% to 4.75%, from 0.7% to 4.5%, from 0.8% to 4.25%, from 0.9% to 4%, from 1% to 3.75%, from 1.25% to 3.5%, from 1.5% to 3.25%, from 1.75% to 3%, from 2% to 2.75%, from 2.25% to 2.5%, from 0.5% to 2.5%, from 0.6% to 2.25%, from 0.7% to 2%, from 0.8% to 1.75%, from 0.9% to 1.5%, from 1% to 1.25%, from 2.25% to 5%, from 2.5% to 4.75%, from 2.75% to 4.5%, from 3% to 4.25%, from 3.25% to 4%, from 3.5% to 3.75%) by weight.
  • the one or more additional components can include a cosurfactant, a co-solvent, or a combination thereof. In some aspects, the one or more additional components can include a co- surfactant. In some aspects, the one or more additional components can include a co-solvent.
  • the one or more additional components can include a co- surfactant.
  • the co-surfactant can include an anionic surfactant, a nonionic surfactant, a cationic surfactant, a zwitterionic surfactant, or any combination thereof.
  • the co-surfactant can include an anionic surfactant.
  • the cosurfactant can include a nonionic surfactant.
  • the co-surfactant can include a cationic surfactant.
  • the co-surfactant can include a zwitterionic surfactant.
  • the co-surfactant may not include a sulfonate.
  • the co-surfactant can include tri styrylphenol (TSP)-based surfactant.
  • TSP tri styrylphenol
  • the co-surfactant can be present in an amount of at least about 0.5% (e.g., at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 1.25%, at least 1.5%, at least 1.75%, at least 2%, at least 2.25%, at least 2.5%, at least 2.75%, at least 3%, at least 3.25%, at least 3.5%, at least 3.75%, at least 4%, at least 4.25%, at least 4.5%, at least 4.75%, at least 5%) by weight.
  • 0.5% e.g., at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 1.25%, at least 1.5%, at least 1.75%, at least 2%, at least 2.25%, at least 2.5%, at least 2.75%, at least 3%, at least 3.25%, at least 3.5%, at least 3.75%, at least 4%, at least 4.25%, at least 4.5%, at least
  • the co-surfactant can be present in an amount of up to 5% (e.g., up to 4.75%, up to 4.5%, up to 4.25%, up to 4%, up to 3.75%, up to 3.5%, up to 3.25%, up to 3%, up to 2.75%, up to 2.5%, up to 2.25%, up to 2%, up to 1.75%, up to 1.5%, up to 1.25%, up to 1%, up to 0.9%, up to 0.8%, up to 0.7%, up to 0.6%, up to 0.5%) by weight.
  • up to 5% e.g., up to 4.75%, up to 4.5%, up to 4.25%, up to 4%, up to 3.75%, up to 3.5%, up to 3.25%, up to 3%, up to 2.75%, up to 2.5%, up to 2.25%, up to 2%, up to 1.75%, up to 1.5%, up to 1.25%, up to 1%, up to 0.9%, up to 0.8%, up to 0.7%,
  • the co-surfactant can be present in an amount ranging from any of the minimum values described above to any of the maximum values described above.
  • the co-surfactant can be present in an amount of from about 0.5% to about 5% (e.g., from 0.6% to 4.75%, from 0.7% to 4.5%, from 0.8% to 4.25%, from 0.9% to 4%, from 1% to 3.75%, from 1.25% to 3.5%, from 1.5% to 3.25%, from 1.75% to 3%, from 2% to 2.75%, from 2.25% to 2.5%, from 0.5% to 2.5%, from 0.6% to 2.25%, from 0.7% to 2%, from about 0.8% to 1.75%, from 0.9% to 1.5%, from 1% to 1.25%, from 2.25% to 5%, from 2.5% to about 4.75%, from 2.75% to 4.5%, from 3% to 4.25%, from 3.25% to about 4%, from 3.5% to about 3.75%) by weight.
  • the one or more additional components can include a co-solvent.
  • the co-solvent can include an alcohol, an alcohol ethoxylate, a glycol ether, glycol, glycerol, or any combination thereof.
  • the surfactant blends provided herein may include more than one co-solvent.
  • the one or more additional components can include a plurality of different co-solvents. Where the one or more additional components include a plurality of different co-solvents, the different co-solvents can be distinguished by their chemical (structural) properties.
  • the one or more additional components may include a first co-solvent, a second co-solvent and a third cosolvent, wherein the first co-solvent may be chemically different from the second and the third co-solvent, and the second co-solvent may be chemically different from the third cosolvent.
  • the plurality of different co-solvents can include at least two different alcohols (e.g., a Ci-Ce alcohol and a C1-C4 alcohol).
  • the one or more additional components can include a Ci-G, alcohol and a C1-C4 alcohol.
  • the plurality of different co-solvents can include at least two different alkoxy alcohols (e.g., a Ci-Ce alkoxy alcohol and a C1-C4 alkoxy alcohol).
  • the one or more additional components can include a Ci-Ce alkoxy alcohol and a C1-C4 alkoxy alcohol.
  • the plurality of different co-solvents can include at least two cosolvents selected from the group consisting of alcohols, alkyl alkoxy alcohols and phenyl alkoxy alcohols.
  • the plurality of different co-solvents may include an alcohol and an alkyl alkoxy alcohol, an alcohol and a phenyl alkoxy alcohol, or an alcohol, an alkyl alkoxy alcohol and a phenyl alkoxy alcohol.
  • the alkyl alkoxy alcohols or phenyl alkoxy alcohols provided herein may have a hydrophobic portion (alkyl or aryl chain), a hydrophilic portion (e.g., an alcohol) and optionally an alkoxy (ethoxylate or propoxylate) portion.
  • the co-solvent can be an alcohol, alkoxy alcohol, glycol ether, glycol or glycerol.
  • Suitable co-solvents are known in the art, and can include, for example, surfactants described in U.S. Patent Application Publication No. 2013/0281327 which is hereby incorporated herein in its entirety.
  • the surfactant blend can further include a chelating agent.
  • the chelating agent can include ethylenediaminetetraacetic acid (EDTA), methylglycinediacetic acid (MGDA), glutamic acid N,N-diacetic acid (GLDA), ethylene glycol-bis(P-aminoethyl ether)-N,N,N',N'-tetraacetic acid (EGTA), diethylenetriamine pentaacetate (DTPA), di ethylenetriamine penta(methylene phosphonic acid) (DTPMP), 1- Hydroxy Ethylidene-l,l-Diphosphonic Acid (HEDP), a sulfosuccinate (e.g., disodium N- octadecyl sulfosuccinate, disodium lauryl sulfosuccinate, diammonium lauryl sulfosuccinate, sodium lauryl sulfosuccinate, sodium lauryl
  • the surfactant blend can be produced by any of the disclosed methods.
  • solubilizer including any of the disclosed surfactant blends.
  • the solubilizer can be produced by any of the disclosed methods.
  • Described herein are methods of displacing a hydrocarbon material in contact with a solid material.
  • the method includes contacting a hydrocarbon material with a compound as described herein, wherein the hydrocarbon material is in contact with a solid material.
  • the hydrocarbon material is allowed to separate from the solid material thereby displacing the hydrocarbon material in contact with the solid material.
  • the hydrocarbon material is unrefined petroleum (e.g., in a petroleum reservoir).
  • the unrefined petroleum is an unrefined petroleum with an API gravity greater than 30.
  • the API gravity of the unrefined petroleum is greater than 30.
  • the API gravity of the unrefined petroleum is greater than 40.
  • the API gravity of the unrefined petroleum is greater than 50.
  • the API gravity of the unrefined petroleum is greater than 60.
  • the API gravity of the unrefined petroleum is greater than 70.
  • the API gravity of the unrefined petroleum is greater than 80.
  • the API gravity of the unrefined petroleum is greater than 90.
  • the API gravity of the unrefined petroleum is greater than 100. In some other embodiments, the API gravity of the unrefined petroleum is between 30 and 100.
  • the solid material may be a natural solid material (i.e., a solid found in nature such as rock).
  • the natural solid material may be found in a petroleum reservoir.
  • the method is an enhanced oil recovery method.
  • Enhanced oil recovery methods are well known in the art. A general treatise on enhanced oil recovery methods is Basic Concepts in Enhanced Oil Recovery Processes edited by M. Baviere (published for SCI by Elsevier Applied Science, London and New York, 1991).
  • the displacing of the unrefined petroleum in contact with the solid material is accomplished by contacting the unrefined with a compound provided herein, wherein the unrefined petroleum is in contact with the solid material.
  • the unrefined petroleum may be in an oil reservoir.
  • the compound or composition provided herein can be pumped into the reservoir in accordance with known enhanced oil recovery parameters.
  • the compound can be pumped into the reservoir as part of the aqueous compositions provided herein and, upon contacting the unrefined petroleum, form an emulsion composition provided herein.
  • the natural solid material can be rock or regolith.
  • the natural solid material can be a geological formation such as clastics or carbonates.
  • the natural solid material can be either consolidated or unconsolidated material or mixtures thereof.
  • the hydrocarbon material may be trapped or confined by "bedrock" above or below the natural solid material.
  • the hydrocarbon material may be found in fractured bedrock or porous natural solid material.
  • the regolith is soil.
  • an emulsion forms after the contacting step.
  • the emulsion thus formed can be the emulsion described above.
  • the emulsion thus formed can be a microemulsion.
  • the method includes allowing an unrefined petroleum acid within the unrefined petroleum material to enter into the emulsion, thereby converting the unrefined petroleum acid into a surfactant.
  • the unrefined petroleum acid converts into a surfactant it is mobilized and therefore separates from the solid material.
  • a method of converting (e.g., mobilizing) an unrefined petroleum acid into a surfactant is provided.
  • the method includes contacting a petroleum material with an aqueous composition or a surfactant blend described herein thereby forming an emulsion in contact with the petroleum material, wherein the aqueous composition includes the compound described herein.
  • the aqueous composition is the aqueous composition described above.
  • An unrefined petroleum acid within the unrefined petroleum material is allowed to enter into the emulsion, thereby converting the unrefined petroleum acid into a surfactant.
  • the reactive petroleum material is in a petroleum reservoir.
  • the unrefined petroleum acid is a naphthenic acid.
  • the unrefined petroleum acid is a mixture of naphthenic acid.
  • the aqueous composition further includes an alkali agent.
  • the composition can include a compound described herein, an alkali agent, an additional surfactant, a co-solvent, and a polymer.
  • Methods can comprise injecting a composition of this type into a hydrocarbon reservoir comprising unrefined petroleum material in contact with the solid material.
  • the unrefined petroleum material can comprise an active oil.
  • the composition can have a pH effective to convert unrefined petroleum acid present in the unrefined petroleum material into a surfactant.
  • the composition can include a compound described herein, an alkali agent, co-solvent, and a polymer.
  • Methods can include injecting a composition of this type into a hydrocarbon reservoir including unrefined petroleum material in contact with the solid material.
  • the unrefined petroleum material can include an active oil.
  • the composition can have a pH effective to convert unrefined petroleum acid present in the unrefined petroleum material into a surfactant.
  • the composition can include a compound described herein, a co-solvent, and a polymer.
  • Methods can include injecting a composition of this type into a hydrocarbon reservoir including unrefined petroleum material in contact with the solid material.
  • the composition can include a compound described herein.
  • Methods can include injecting a composition of this type into a hydrocarbon reservoir comprising unrefined petroleum material in contact with the solid material.
  • the unrefined petroleum material can include an active oil.
  • the composition can have a pH effective to convert unrefined petroleum acid present in the unrefined petroleum material into a surfactant.
  • the cashew nut shell liquid (CNSL) or a component thereof includes anacardiac acid, cardanol, cardol, 2-methylcardol, or a combination thereof.
  • the cashew nut shell liquid (CNSL) can include a mixture comprising from 70-80% by weight anacardiac acid (e.g., from 74-78% by weight anacardiac acid), from 0.5%-10% by weight cardanol (e.g., from 1 %-10% by weight cardanol), from 12-23% by weight cardol (e.g., from 15-21% by weight cardol), and from 1 to 5% by weight 2- methylcardol (e.g., from 1-3% by weight 2-methylcardol).
  • Alkoxylating the cashew nut shell liquid (CNSL) or the component thereof can include propoxylation, ethoxylation, or a combination thereof.
  • the method can further include functionalizing the alkoxylated cashew nut shell liquid (CNSL) or the component thereof to include an anionic moiety, a cationic moiety, or a zwitterionic moiety.
  • the anionic moiety can include, for example a carboxylate moiety, a sulfate moiety, a sulfonate moiety, or a combination thereof.
  • the method can further include combining the alkoxylated cashew nut shell liquid (CNSL) or a component thereof with one or more additional components.
  • CNSL alkoxylated cashew nut shell liquid
  • the one or more additional components can include an additional surfactant, a co-solvent, polymer, alkali agent, or any combination thereof described herein.
  • the lipid precursor can include a glycerolipid (e.g., a monoglyceride, diglyceride, and/or triglyceride), a glycerophospholipid, a saccharolipid, a sphingolipid, or any combination thereof.
  • the lipid precursor can include a glycerolipid.
  • the lipid precursor can include a glycerophospholipid.
  • the lipid precursor can include a saccharolipid.
  • the lipid precursor can include a sphingolipid.
  • the lipid precursor can include a monoglyceride, a diglyceride, a triglyceride, or any combination thereof. In some such aspects, the lipid precursor can include a monoglyceride. In other such aspects, the lipid precursor can include a diglyceride. In yet other such aspects, the lipid precursor can include a triglyceride.
  • the lipid precursor can include at least one unsaturated fatty acid substituent. In other aspects, the lipid precursor can include at least one saturated fatty acid substituent. In yet other aspects, the lipid precursor can include at least one unsaturated fatty acid salt and at least one saturated fatty acid salt. In some aspects, the lipid precursor can include at least one branched fatty acid substituent.
  • the lipid precursor can include one or more fatty acid substituents selected from capryllic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, myristoleic acid, pentadecyclic acid, palmitic acid, palmitoleic acid, sapienic acid, margaric acid, stearic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, a-linolenic acid, y-linolenic acid, stearidonic acid, nonadecylic acid, arachidic acid, eicosenoic acid, dihomo-y-linolenic acid, mead acid, arachidonic acid, eicosapentaenoic acid, heneicosylic acid, behenic acid, erucic acid, docosahexaenoic acid,
  • the lipid precursor can include one or more components from almond oil, argan oil, avocado oil, beech nut oil, broccoli seed oil, canola oil, cashew oil, cashew nut shell liquid, citrus oils, cocoa butter, coconut fat or oil, corn oil, cotton seed oil, flaxseed oil, grape seed oil, grapefruit seed oil, hazelnut oil, jojoba oil, lard, lemon oil, linseed oil, macadamia oil, mango kernel oil, melons and gourd seeds oils, mustard oil, olive oil, orange oil, palm kernel oil, palm oil, palmolein oil, peanut oil, pecan oil, pistachio oil, pine nut oil, pumpkin oil, rapeseed oil, rosehip seed oil, safflower oil, sesame oil, shea butter, soybean oil, sunflower oil, tallow, thistle oil, walnut oil, watermelon seed oil, wheat germ oil, or any combination thereof.
  • the carboxylic acid surfactant can include caprylate, pelargonate, caprate, undecylate, laurate, tridecylate, myristate, myristoleate, pentadecylate, palmitate, palmitoleate, sapienate, margarate, stearate, oleate, elaidate, vaccenate, linoleate, linoelaidate, a-linolenate, y-linolenate, stearidonate, nonadecylate, arachidate, eicosenoate, dihomo-y- linolenate, meadate, arachidonate, eicosapentaenoate, heneicosylate, behenate, erucate, docosahexaenoate, tricosylate, lignocerate, nervonate, pentacosylate, cerotate, heptacosylate,
  • the carboxylate surfactant can include a compound of Formula IV
  • the carboxylic acid surfactant can be derived from cashew nut shell liquid.
  • R 1 can represent a linear C15 alkyl group or a linear C15 alkenyl group.
  • R 1 can represent a linear C15 alkyl group or a linear C15 alkenyl group. In some such aspects, R 1 can be represented by the structure
  • R 1 can be a linear C15 monoene, a linear C15 diene, or a linear C15 triene. In some such aspects, R 1 can be represented by the structure i n other such aspects, R 1 can be represented by the . in yet other such aspects, R 1 can be represented by the structure
  • the carboxylic acid surfactant can include a compound of Formula V:
  • each of R 2 and R 3 can independently represent a C4-C20 alkyl group or a C4-C20 alkenyl group.
  • the carboxylic acid surfactant can be produced by the Guerbet reaction.
  • the carboxylic acid surfactant can include 2-butyl-octanoic acid, 2- hexyl-decanoic acid, 2-decyl-tetradecanoic acid, 2-tetradecyl-octadecanoic acid, or any combination thereof.
  • the carboxylic acid surfactant can include another oxidized Guerbet alcohol.
  • the one or more additional components can include a cosurfactant, a co-solvent, or a combination thereof. In some aspects, the one or more additional components can include a co- surfactant. In some aspects, the one or more additional components can include a co-solvent.
  • hydrolyzing the lipid precursor can include: i) adding the lipid precursor to water; ii) adding a pH adjusting agent to induce hydrolysis of ester bonds in the lipid precursor.
  • the one or more additional components can be added before step i). In other such aspects, the one or more additional components can be added in step i). In yet other such aspects, the one or more additional components can be added between step i) and step ii). In yet still other such aspects, the one or more additional components can be added in step ii). In yet still other such aspects, the one or more additional components can be added after step ii).
  • the pH adjusting agent can be a base.
  • hydrolyzing the lipid precursor can include: i) adding the lipid precursor to water including a pH adjusting agent to induce hydrolysis of ester bonds in the lipid precursor.
  • the one or more additional components can be added before step i).
  • the one or more additional components can be added in step i).
  • the one or more additional components can be added after step i).
  • the pH adjusting agent can be a base.
  • hydrolyzing the lipid precursor can include: i) combining the lipid precursor and the one or more additional components, the one or more additional components including water and a pH adjusting agent, to induce hydrolysis of ester bonds in the lipid precursor.
  • the pH adjusting agent can be a base.
  • the method can further include adjusting the concentration of the carboxylate surfactant and/or the one or more additional components in the surfactant blend. In some such aspects, the method can further include adding additional water to the surfactant blend. In other such aspects, the method can further include adding additional co-surfactant to the surfactant blend. In yet other such aspects, the method can further include adding additional co-solvent to the surfactant blend.
  • the carboxylic acid surfactant can be derived from cashew nut shell liquid.
  • R 1 can represent a linear C15 alkyl group or a linear C15 alkenyl group. In some aspects, R 1 can represent a linear C15 alkyl group. In some aspects, R 1 can represent a linear C15 alkenyl group. In some such aspects, R 1 can be represented by the structure
  • the one or more additional components can include a co- surfactant.
  • the co-surfactant can include an anionic surfactant, a nonionic surfactant, a cationic surfactant, a zwitterionic surfactant, or any combination thereof.
  • the co-surfactant can include an anionic surfactant.
  • the cosurfactant can include a nonionic surfactant.
  • the co-surfactant can include a cationic surfactant.
  • the co-surfactant can include a zwitterionic surfactant.
  • the co-surfactant may not include a sulfonate.
  • the co-surfactant can include tri styrylphenol (TSP)-based surfactant.
  • TSP tri styrylphenol
  • the co-surfactant can be present in an amount of at least about 0.5% (e.g., at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 1.25%, at least 1.5%, at least 1.75%, at least 2%, at least 2.25%, at least 2.5%, at least 2.75%, at least 3%, at least 3.25%, at least 3.5%, at least 3.75%, at least 4%, at least 4.25%, at least 4.5%, at least 4.75%, at least 5%) by weight.
  • 0.5% e.g., at least 0.6%, at least 0.7%, at least 0.8%, at least 0.9%, at least 1%, at least 1.25%, at least 1.5%, at least 1.75%, at least 2%, at least 2.25%, at least 2.5%, at least 2.75%, at least 3%, at least 3.25%, at least 3.5%, at least 3.75%, at least 4%, at least 4.25%, at least 4.5%, at least
  • the co-surfactant can be present in an amount of up to 5% (e.g., up to 4.75%, up to 4.5%, up to 4.25%, up to 4%, up to 3.75%, up to 3.5%, up to 3.25%, up to 3%, up to 2.75%, up to 2.5%, up to 2.25%, up to 2%, up to 1.75%, up to 1.5%, up to 1.25%, up to 1%, up to 0.9%, up to 0.8%, up to 0.7%, up to 0.6%, up to 0.5%) by weight.
  • up to 5% e.g., up to 4.75%, up to 4.5%, up to 4.25%, up to 4%, up to 3.75%, up to 3.5%, up to 3.25%, up to 3%, up to 2.75%, up to 2.5%, up to 2.25%, up to 2%, up to 1.75%, up to 1.5%, up to 1.25%, up to 1%, up to 0.9%, up to 0.8%, up to 0.7%,
  • the co-surfactant can be present in an amount ranging from any of the minimum values described above to any of the maximum values described above.
  • the co-surfactant can be present in an amount of from about 0.5% to about 5% (e.g., from 0.6% to 4.75%, from 0.7% to 4.5%, from 0.8% to 4.25%, from 0.9% to 4%, from 1% to 3.75%, from 1.25% to 3.5%, from 1.5% to 3.25%, from 1.75% to 3%, from 2% to 2.75%, from 2.25% to 2.5%, from 0.5% to 2.5%, from 0.6% to 2.25%, from 0.7% to 2%, from about 0.8% to 1.75%, from 0.9% to 1.5%, from 1% to 1.25%, from 2.25% to 5%, from 2.5% to about 4.75%, from 2.75% to 4.5%, from 3% to 4.25%, from 3.25% to about 4%, from 3.5% to about 3.75%) by weight.
  • the one or more additional components can include a co-solvent.
  • the co-solvent can include an alcohol, an alcohol ethoxylate, a glycol ether, glycol, glycerol, or any combination thereof.
  • the surfactant blends provided herein may include more than one co-solvent.
  • the one or more additional components can include a plurality of different co-solvents. Where the one or more additional components include a plurality of different co-solvents, the different co-solvents can be distinguished by their chemical (structural) properties.
  • the one or more additional components may include a first co-solvent, a second co-solvent and a third cosolvent, wherein the first co-solvent may be chemically different from the second and the third co-solvent, and the second co-solvent may be chemically different from the third cosolvent.
  • the plurality of different co-solvents can include at least two different alcohols (e.g., a Ci-Ce alcohol and a C1-C4 alcohol).
  • the one or more additional components can include a Ci-G> alcohol and a C1-C4 alcohol.
  • the plurality of different co-solvents can include at least two different alkoxy alcohols (e.g., a Ci-Ce alkoxy alcohol and a C1-C4 alkoxy alcohol).
  • the one or more additional components can include a Ci-Ce alkoxy alcohol and a C1-C4 alkoxy alcohol.
  • the plurality of different co-solvents can include at least two cosolvents selected from the group consisting of alcohols, alkyl alkoxy alcohols and phenyl alkoxy alcohols.
  • the plurality of different co-solvents may include an alcohol and an alkyl alkoxy alcohol, an alcohol and a phenyl alkoxy alcohol, or an alcohol, an alkyl alkoxy alcohol and a phenyl alkoxy alcohol.
  • the alkyl alkoxy alcohols or phenyl alkoxy alcohols provided herein may have a hydrophobic portion (alkyl or aryl chain), a hydrophilic portion (e.g., an alcohol) and optionally an alkoxy (ethoxylate or propoxylate) portion.
  • the co-solvent can be an alcohol, alkoxy alcohol, glycol ether, glycol or glycerol.
  • Suitable co-solvents are known in the art, and can include, for example, surfactants described in U.S. Patent Application Publication No. 2013/0281327 which is hereby incorporated herein in its entirety.
  • the surfactant blend can further include a chelating agent.
  • the chelating agent can include ethylenediaminetetraacetic acid (EDTA), methylglycinediacetic acid (MGDA), glutamic acid N,N-diacetic acid (GLDA), ethylene glycol-bis(P-aminoethyl ether)-N,N,N',N'-tetraacetic acid (EGTA), diethylenetriamine pentaacetate (DTP A), diethylenetriamine penta(methylene phosphonic acid) (DTPMP), 1- Hydroxy Ethylidene-l,l-Diphosphonic Acid (HEDP), a sulfosuccinate (e.g., disodium N- octadecyl sulfosuccinate, disodium lauryl sulfosuccinate, diammonium lauryl sulfosuccinate, sodium lauryl sulfosuccinate, sodium lauryl
  • the precursor blend can be basic. In some aspects, the precursor blend can have a pH of about 8 or greater (e.g., about 8.5 or greater, about 9 or greater, about 9.5 or greater, about 10 or greater, about 10.5 or greater, about 11 or greater, about 11.5 or greater, about 12 or greater). In some aspects, the precursor blend can have a pH of about 10 or greater.
  • Oils may contain Naphthenic acids that may be difficult to neutralize with Alkali. Thus, such oils may appear as "inactive" oils. Inclusion of a carboxylate(Soap) in the alkaline formulation results in evidence for Naphthenic soap generation from an “inactive” oil.
  • Active oil was used in these studies to study the efficacy of the proposed classes of surface active agents.
  • Active oil properties viscous oil at 25°C with high naphthenic acid level (acid number >2mg KOH/g of oil) (Ref. ⁇ 0.5mg KOH/g of Oil considered inactive, 0.5- Img considered partially active, and >lmg/g of oil considered active oil).
  • Surface Active Carboxylate CI I-CO2 Na (Sodium Laurate) is the same as C12 carboxylate-Na salt.
  • Source coconut oil. Coconut oil was hydrolyzed to lauric acid and higher acids. Lauric acid neutralization gives sodium laurate with very low water solubility at 25°C.
  • Cashew nut shells are considered “agricultural waste”.
  • the liquid squeezed out via mechanical, thermal, or solvent means produce up to 20% of the Cashew Nut Shells Liquid (“CNSL”).
  • the non-carboxylate components are grouped together as card phenol.
  • Figure 6 shows the composition of CNSL.
  • CNSL can be thermally decarboxylated into card phenol.
  • Card phenol can be alkoxylated with PO and EO followed by optional functionalization.
  • Aqueous Stability is limited, specially with NaCl or Na2CO3 scan.
  • Co-solvent such as lBA(lso- Butanol) helps improve Aqueous Stability. See Figure 3.
  • Figure 4A and 4B show phase behavior images and oil and water solubilization ratios for ASP Formulation 17 (0.3 wt% cardphenol-5PO-5EO and 0.3 wt% C20:24IOS at a temperature of 70°C and with an oil viscosity of 3.2 cp with Na2CO3.
  • Figure 5A and 5B show phase behavior images and oil and water solubilization ratios for SP Formulation 17 (0.3 wt% cardphenol -5PO-5EO and 0.3 wt% C20:24IOS at a temperature of 70°C and with an oil viscosity of 3.2 cp with NaCl.
  • compositions and methods disclosed and claimed herein can be made and executed without undue experimentation in light of the present disclosure. While the compositions and methods of this disclosure have been described in terms of preferred embodiments, it will be apparent to those of skill in the art that variations may be applied to the compositions and methods and in the steps or in the sequence of steps of the methods described herein without departing from the concept, spirit and scope of the disclosure. More specifically, it will be apparent that certain agents which are both chemically related may be substituted for the agents described herein while the same or similar results would be achieved. All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosure as defined by the appended claims.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des mélanges de tensioactifs et des solubilisants comprenant des tensioactifs d'acide carboxylique et leurs procédés de préparation. L'invention concerne également des tensioactifs dérivés de baume de cajou, ainsi que des compositions les comprenant et des procédés d'utilisation de ceux-ci dans des opérations pétrolières et gazières.
PCT/US2025/026673 2024-04-26 2025-04-28 Compositions tensioactives comprenant des carboxylates et leurs procédés de fabrication Pending WO2025227154A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US202463639369P 2024-04-26 2024-04-26
IN202411033319 2024-04-26
US63/639,369 2024-04-26
IN202411033319 2024-04-26

Publications (1)

Publication Number Publication Date
WO2025227154A1 true WO2025227154A1 (fr) 2025-10-30

Family

ID=97491099

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2025/026673 Pending WO2025227154A1 (fr) 2024-04-26 2025-04-28 Compositions tensioactives comprenant des carboxylates et leurs procédés de fabrication

Country Status (1)

Country Link
WO (1) WO2025227154A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090305942A1 (en) * 2008-04-09 2009-12-10 Solazyme, Inc. Soaps Produced from Oil-Bearing Microbial Biomass and Oils
US20110294174A1 (en) * 2010-05-28 2011-12-01 Solazyme, Inc. Tailored Oils Produced From Recombinant Heterotrophic Microorganisms
US20150031766A1 (en) * 2005-07-06 2015-01-29 Ecolab Usa Inc. Surfactant peroxycarboxylic acid compositions
US20240000697A1 (en) * 2020-11-12 2024-01-04 C16 Biosciences, Inc. Personal care compositions comprising microbially produced oil

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150031766A1 (en) * 2005-07-06 2015-01-29 Ecolab Usa Inc. Surfactant peroxycarboxylic acid compositions
US20090305942A1 (en) * 2008-04-09 2009-12-10 Solazyme, Inc. Soaps Produced from Oil-Bearing Microbial Biomass and Oils
US20110294174A1 (en) * 2010-05-28 2011-12-01 Solazyme, Inc. Tailored Oils Produced From Recombinant Heterotrophic Microorganisms
US20240000697A1 (en) * 2020-11-12 2024-01-04 C16 Biosciences, Inc. Personal care compositions comprising microbially produced oil

Similar Documents

Publication Publication Date Title
Fu et al. Study on organic alkali-surfactant-polymer flooding for enhanced ordinary heavy oil recovery
US9783729B2 (en) Alkoxy carboxylate surfactants
US9862877B2 (en) Alkyl hydrophobe surfactants
US20210163814A1 (en) In-situ emulsification and viscosity increase system with high phase change point and application thereof in water-flooding oil reservoir
CN1080362C (zh) 提高油田和气田生产用化学药品的效率的方法
US20220025247A1 (en) Methods for hydrocarbon recovery using alkoxylate emulsions
US20160264847A1 (en) Short Hydrophobe Anionic Surfactants
Motraghi et al. Interfacial tension reduction of hybrid crude-oil/mutual-solvent systems under the influence of water salinity, temperature and green SiO2/KCl/Xanthan nanocomposites
US9206347B2 (en) Quaternary ammonium surfactants
WO2015161124A1 (fr) Compositions de tensioactifs époxydes géminés
Hama et al. Experimental investigation of new derived anionic natural surfactant from peanut oil: Application for enhanced oil recovery
Tunnish et al. Alkaline‐ionic liquid slug injection for improved heavy oil recovery
Nowrouzi et al. Chemical Enhanced Oil Recovery from Carbonate Reservoirs by Coherent Surfactant and Surfactant–Alkali (SA) Slug Injection Using a Green Cationic Surfactant Synthesized from Avocado Oil
WO2023028377A1 (fr) Alcoxylates hydrophobes ultra-courts utilisés en tant que solvants ou co-solvants
WO2017089724A1 (fr) Composition pour limiter la formation et/ou l'agglomeration d'hydrates de gaz
WO2025227154A1 (fr) Compositions tensioactives comprenant des carboxylates et leurs procédés de fabrication
US20160311744A1 (en) Alkoxylated co-solvents
CN116554848B (zh) 一种驱油用表面活性剂组合物
WO2010105879A1 (fr) Composition viscoelastique a viscosite amelioree
WO2023028376A1 (fr) Alcoxylates hydrophobes ultra-courts utilisés en tant que tensioactifs
WO2023028378A1 (fr) Hydrophobes ultra-courts pour réservoirs non conventionnels comprenant des huiles légères contenant un gaz en solution
CA2859015A1 (fr) Compositions de co-solvant leger
FR2458671A1 (fr) Procede pour recuperer l'huile d'une formation petrolifere
EP3143097A1 (fr) Stabilisateurs de mousse de type aminosulfonate
WO2025117675A1 (fr) Alcoxylates hydrophobes ultra-courts utilisés en tant que tensioactifs

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 25795367

Country of ref document: EP

Kind code of ref document: A1