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WO2024239261A1 - Produits de réaction de carbonate d'alkyl glycosides et leurs procédés d'utilisation - Google Patents

Produits de réaction de carbonate d'alkyl glycosides et leurs procédés d'utilisation Download PDF

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Publication number
WO2024239261A1
WO2024239261A1 PCT/CN2023/095941 CN2023095941W WO2024239261A1 WO 2024239261 A1 WO2024239261 A1 WO 2024239261A1 CN 2023095941 W CN2023095941 W CN 2023095941W WO 2024239261 A1 WO2024239261 A1 WO 2024239261A1
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Prior art keywords
composition
salt
alkyl
organic carbonate
alkyl glycoside
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PCT/CN2023/095941
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English (en)
Inventor
Shaohua Chen
Ming Han
Tianping Huang
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Aramco Far East Beijing Business Services Co Ltd
Saudi Arabian Oil Co
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Aramco Far East Beijing Business Services Co Ltd
Saudi Arabian Oil Co
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Application filed by Aramco Far East Beijing Business Services Co Ltd, Saudi Arabian Oil Co filed Critical Aramco Far East Beijing Business Services Co Ltd
Priority to PCT/CN2023/095941 priority Critical patent/WO2024239261A1/fr
Priority to CN202380014152.4A priority patent/CN119365475A/zh
Publication of WO2024239261A1 publication Critical patent/WO2024239261A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
    • C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00

Definitions

  • the present disclosure generally relates to surfactants and, more specifically, surfactants exhibiting compatibility toward salt-containing environments and that are produced from a biologically sourced material.
  • surfactants Compounds having both hydrophobic and hydrophilic regions within their molecular structure are amphiphilic and may exhibit surfactancy. As such, such compounds are commonly referred to as “surfactants” or “surfactant compounds. ” By virtue of their molecular structure, surfactants tend to lower the interfacial tension at the interface between two substances. Because of their ability to lower interfacial tension, as well as facilitating other properties associated therewith (e g , foaming, emulsification, de-emulsification, surface wetting, and the like) , surfactants may be utilized in a wide range of consumer and industrial products and processes. Among such consumer and industrial products are, for example, soaps, detergents, cosmetics, pharmaceuticals, paints, and dispersants.
  • Surfactants are also commonly used in the oil and gas industry, such as during enhanced hydrocarbon recovery (e g , enhanced oil recovery, EOR) processes.
  • EOR enhanced oil recovery
  • surfactants may change wettability of a surface to promote hydrocarbon release therefrom, promote emulsificiation or de-emulsification of oleaginous substances, and/or reduce the viscosity of a fluid, as non-limiting examples.
  • a number of common surfactants exhibit poor biodegradability and/or varying degrees of aquatic toxicity. As such, these types of surfactants may be subject to various environmental and/or other government regulations.
  • a number of surfactants are rather expensive and some may exhibit limited tolerance to environments having high salinity (e g , about 5 wt. %salt or greater, including aqueous salt solutions, seawater, and brines) .
  • surfactants may tend to lower interfacial tension at an interface between two substances, some aqueous surfactant solutions themselves may exhibit surface tension values that are higher than desired, especially at the critical micelle concentration.
  • the limited salt tolerance may restrict the range of applications in which many conventional surfactants can be effectively used, and the high interfacial tension values may complicate fluid handling when using such surfactants.
  • compositions comprising: an organic carbonate salt comprising an anionic portion that is a carbonate reaction product of an alkyl glycoside.
  • the present disclosure provides methods for treating a subterranean formation, comprising: providing a composition comprising an organic carbonate salt comprising an anionic portion that is a carbonate reaction product of an alkyl glycoside; and introducing the composition into a subterranean formation.
  • the present disclosure provides methods for producing organic carbonate salts, comprising: contacting an alkyl glycoside with an elevated pressure of carbon dioxide in the presence of a non-nucleophilic base; and obtaining an organic carbonate salt comprising a cationic portion comprising the non-nucleophilic base in protonated form and an anionic portion that is a carbonate reaction product of the alkyl glycoside.
  • FIG. 1 is a plot of comparative FTIR spectra of an alkyl polyglycoside and an alkyl polyglycoside carbonate salt reaction product.
  • FIG. 2 is a plot of comparative UV-VIS spectra of an alkyl polyglycoside and an alkyl polyglycoside carbonate salt reaction product.
  • FIG. 3 is a plot of interfacial tension as a function of time for an alkyl glycoside and an alkyl glycoside carbonate salt reaction product.
  • the present disclosure generally relates to surfactants and, more specifically, surfactants exhibiting compatibility toward salt-containing environments and that are produced from a biologically sourced material.
  • surfactants may present various issues such as high cost, poor biocompatibility or biodegradability, limited compatibility with environments having high salinity, and high interfacial tension values. One or more of these factors may limit applicability of such surfactants in various applications.
  • Surfactants that are incompatible with high-salinity environments may precipitate when contacted therewith, whereas the surfactant may remain soluble (compatible) when contacted with water or an aqueous fluid having sufficiently low salinity.
  • Alkyl glycosides are saccharide oligomers or polymers known to exhibit surfactancy and biodegradability.
  • Alkyl glycosides comprise a saccharide polymer backbone having adjacent monosaccharide units linked by glycosidic bonds, wherein a terminal monosaccharide unit is functionalized with a long-chain alkyl group upon an oxygen atom that would otherwise form a glycosidic bond to another monosaccharide unit.
  • alkyl glycosides may be useful non-ionic surfactants in various applications, alkyl glycosides may exhibit limited tolerance toward aqueous salt solutions.
  • as-produced alkyl glycosides may demonstrate unacceptably high interfacial tension.
  • alkyl glycosides may be surprisingly enhanced by chemically transforming a parent alkyl glycoside from a neutral surfactant into an anionic surfactant.
  • a parent alkyl glycoside from a neutral surfactant into an anionic surfactant.
  • an organic carbonate group specifically as a salt of the organic carbonate group
  • increased tolerance toward aqueous salt solutions and similar high-salinity environments may be realized.
  • decreased interfacial tension may be realized in comparison to the parent alkyl glycoside at a similar concentration in an aqueous fluid.
  • an organic carbonate group may be readily introduced to an alkyl glycoside and converted into a salt form using carbon dioxide in the presence of a suitably strong base, wherein the strong base may deprotonate the organic carbonate group to produce the salt form.
  • the organic carbonate group is believed to form at the primary alcohol position of at least a portion of the monosaccharide units defining the saccharide polymer backbone (in the case of an alkyl glycoside comprising predominantly 1, 4-glycosidic bonds) . Any formation of organic carbonate groups at the secondary alcohol positions of the monosaccharide units within an alkyl glycoside comprising predominantly 1, 4-glycosidic bonds is believed to be much more difficult due to increased steric hindrance.
  • organic carbonate groups introduced through a reaction with carbon dioxide in the presence of a suitably strong base may differ from cyclic carbonates formed by a reaction of adjacent hydroxyl groups with reagents such as phosgene.
  • compositions of the present disclosure may comprise an organic carbonate salt having an anionic portion that is a carbonate reaction product of an alkyl glycoside.
  • Alkyl glycosides having all ⁇ (1, 4) glycosidic bonds between adjacent glucose monomers may have a structure represented by Formula 1 below, wherein
  • variable a is 0 or a positive integer
  • R is an alkyl group upon the terminal glucose monomer unit, which defines the “alkyl” portion of the alkyl glycoside.
  • Alkyl glycosides may have a molecular weight varying over a range of values, such as about 220 or above, or about 380 or above, or about 545 or above, or 700 or above.
  • the alkyl group may comprise a C 4 -C 24 alkyl group, or a C 6 -C 20 alkyl group, or a C 8 -C 18 alkyl group, or a C 6 -C 14 alkyl group, or a C 10 -C 16 alkyl group, or a C 12 -C 14 alkyl group in non-limiting examples.
  • a given preparation of alkyl glycosides may contain a varying number of monosaccharide units, as well as a range of alkyl group sizes.
  • the molecular weight of suitable alkyl glycosides for use in the disclosure herein may range from about 220 to about 5000, or about 320 to about 2000, or about 320 to about 1000, or about 400 to about 800, or about 600 to about 1200, or about 350 to about 750.
  • As few as one monosaccharide unit may be present, or as many as 2, 3, 4, 5, 10, 15, or even 20 monosaccharide units may be present in a parent alkyl glycoside prior to introduction of one or more organic carbonate groups thereto in salt form.
  • alkyl glycoside herein may refer to either alkyl monoglycosides (one monosaccharide unit) or alkyl polyglycosides (two or more monosaccharide units) . It is to be further appreciated that alkyl glycosides having monosaccharide units other than glucose and/or glycosidic bonds other than ⁇ (1, 4) -glycosidic bonds may also be suitable for use in the disclosure herein. For clarity, Formula 2 shows the IUPAC numbering of a single glucose monomer unit (in the form of an alkyl glycoside) .
  • Organic carbonate salts of the present disclosure may contain at least one monosaccharide unit having a structure represented by Formula 3 below, wherein the C-1 and C-4 alcohol groups may be in the form of glycosidic bonds (in the case of alkyl polyglycosides) , or the C-4 alcohol group of a terminal monosaccharide unit of an alkyl polyglycoside may be alkyl-functionalized.
  • Formula 3 the C-1 and C-4 alcohol groups may be in the form of glycosidic bonds (in the case of alkyl polyglycosides) , or the C-4 alcohol group of a terminal monosaccharide unit of an alkyl polyglycoside may be alkyl-functionalized.
  • B is the protonated form of a strong base.
  • alkyl glycosides undergoing further functionalization to produce an organic carbonate salt according to the disclosure herein may be obtained commercially or synthesized in any suitable manner.
  • suitable alkyl glycosides may be synthesized by reacting a monosaccharide (e g , glucose) or an oligosaccharide (e g , multiple glucose monomer units linked by ⁇ (1, 4) -glycosidic bonds) with a fatty alcohol or a mixture of fatty alcohols in the presence of a suitable acid catalyst.
  • the acid catalyst may promote oligomerization (or further oligomerization) of the monosaccharide units, with the glycosidic bond position (i e , the C-4 alcohol group in the case of glucose) of the terminal monosaccharide unit being etherified with the alkyl group of the fatty alcohol to form a plurality of alkyl glycosides.
  • the plurality of alkyl glycosides may have a range of monosaccharide units linked by glycosidic bonds, each having the terminal monosaccharide unit functionalized with an alkyl group. A range of alkyl group sizes may be present when using a mixture of fatty alcohols.
  • Alkyl glycosides formed through alternative syntheses may also be suitable for use in the disclosure herein.
  • fatty alcohol refers to a long-chain primary alcohol compound bearing optional unsaturation and containing 4 or more carbon atoms, such as about 4 to about 26 carbon atoms, or about 6 to about 24 carbon atoms, or about 8 to about 20 carbon atoms, or about 10 to about 18 carbon atoms, or about 6 to about 14 carbon atoms, or about 10 to about 22 carbon atoms, or about 8 to about 16 carbon atoms.
  • the fatty alcohol (or mixture of fatty alcohols) used to produce an alkyl glycoside may be formed via reduction of a fatty acid or fatty ester, preferably a straight-chain fatty acid or fatty ester.
  • the alkyl glycosides disclosed herein may be free or substantially free of branched alkyl groups, according to various embodiments.
  • Fatty acids may be directly reduced to the corresponding fatty alcohols using known techniques.
  • Fatty esters (including fats or oils) may be directly reduced to the corresponding fatty alcohols using known techniques, or the fatty esters may first be hydrolyzed to fatty acids before undergoing reduction.
  • the alkyl glycosides used herein may contain alkyl group (s) having a size commensurate with the fatty acid (s) or fatty ester (s) from which the fatty alcohols were produced.
  • Illustrative fatty acids (or fatty acids within fatty esters) from which the corresponding fatty alcohols may be obtained through various techniques include, for example, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelabonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, trioscylic acid, lignoceric acid, pentacosylic acid, cerotic acid, crotonic acid, cervonic acid, linoleic acid, linolelaidic acid, linolenic acid, arachidonic acid, docosatetraenoic acid, myristoleic acid, palmitoleic acid, sappenic acid, vaccenic acid,
  • glycerol esters may comprise a fatty ester source for obtaining fatty alcohols for forming an alkyl glycoside suitable for use herein.
  • Suitable glycerol esters from which one or a mixture of fatty alcohols may be obtained through a suitable reduction technique include any plant oil, animal oil, plant fat, animal fat, or any combination thereof that contains one or more desired fatty acids.
  • Suitable glycerol esters may be found in plant or animal sources including, for example, soybean oil, grapeseed oil, olive oil, palm oil, rice bran oil, safflower oil, corn oil, coconut oil, sunflower seed oil, canola oil, rapeseed oil, peanut oil, cottonseed oil, hazelnut oil, tea seed oil, linseed oil, sesame oil, acai oil, almond oil, beech nut oil, brazil nut oil, cashew oil, macadamia nut oil, pecan oil, pine nut oil, pistachio oil, walnut oil, pumpkin seed oil, apricot oil, avocado oil, grapefruit oil, lemon oil, orange oil, mango oil, flax seed oil, fish oil, cocoa butter, hemp oil, castor oil, tall oil, fish oil, cattle fat, buffalo fat, sheep fat, goat fat, duck fat, pig fat, poultry fat, and any combination thereof.
  • soybean oil, grapeseed oil olive oil, palm oil, rice bran oil, s
  • Suitable bases may include non-nucleophile bases, preferably a non-nucleophilic strong base having a pK a of about 10 or greater. More preferably, the non-nucleophilic base may comprise an amidine, preferably a cyclic or bicyclic amidine.
  • suitable amidines that may promote formation of an organic carbonate salt include, but are not limited to, 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) , 1, 5-diazabicyclo [4.3.0] non-5-ene (DBN) , and any combination thereof.
  • a cation portion of the organic carbonate salts of the present disclosure may comprise DBU or DBN, specifically a protonated form of DBU or DBN.
  • compositions of the present disclosure may be further formulated with an aqueous fluid in which the organic carbonate salt is at least partially dissolved and preferably fully dissolved.
  • Aqueous fluids that may be present in the compositions disclosed herein include, but are not limited to, water, salt water, mixtures of water and a water-miscible organic solvent, brine, seawater, produced water, or any combination thereof.
  • the term “brine” refers to any aqueous salt solution having a greater amount of total dissolved salt than does seawater, including saturated aqueous salt solutions. Field or industrial process waters, including produced water from a wellbore, containing a high salt content may be suitably used.
  • compositions of the present disclosure may be formulated with an aqueous fluid that already has a high salt content (e g , greater than 5 wt. %salt based on total mass of the aqueous fluid) , while still remaining tolerant (stably formulated) in the presence of the high salt content.
  • the compositions of the present disclosure may be formulated with an aqueous fluid lacking a dissolved salt or an amount of dissolved salt that is not considered to constitute a high salt content.
  • the compositions may remain tolerant (stably formulated) when contacted with another aqueous fluid having a high salt content. Tolerance of the compositions toward high-salinity aqueous fluids may be evidenced by lack of precipitation or a decrease in clarity.
  • the organic carbonate salt may be present in the aqueous fluid at a concentration of about 20 wt. %or less, or about 10 wt. %or less, or about 5 wt. %or less, such as about 1 wt. %to about 10 wt. %, or about 3 wt. %to about 8 wt. %, each based on total mass of the composition.
  • compositions of the present disclosure may promote emulsification thereof, preferably as an oil-in-water emulsion.
  • the emulsions may break spontaneously within about 24 hours, or within about 12 hours, or within about 8 hours, or within about 4 hours, or within about 2 hours, or within about 1 hour, or within about 30 minutes, or within about 20 minutes, or within about 10 minutes, or within about 5 minutes.
  • de-emulsification may be promoted by introducing a separate de-emulsifier.
  • Oleaginous substances that may be emulsified upon contacting the compositions of the present disclosure, including under high-salinity conditions, are not believed to be particularly limited.
  • Illustrative oleaginous substances may include, for example, petroleum, refined petroleum, diesel, natural gas, plant oils, vegetable oils, an oilfield fluid or a component thereof, or any combination thereof.
  • the compositions of the present disclosure may exhibit low interfacial tension values. At the very least, the compositions of the present disclosure may exhibit a lower interfacial tension than does the corresponding alkyl glycoside prior to being converted into an organic carbonate salt. That is, when formulated in an aqueous fluid at a substantially identical concentration, the organic carbonate salts of an alkyl glycoside may exhibit a lower interfacial tension than does the corresponding unfunctionalized (parent) alkyl glycoside. In non-limiting examples, the interfacial tension of the organic carbonate salt may decrease by at least a factor of 5 relative to the unfunctionalized alkyl glycoside.
  • the interfacial tension may decrease by at least a factor of 10, or by at least a factor of 15, or by at least a factor of 20, or by at least a factor of 30, or by at least a factor of 40, or by at least a factor of 50 relative to the unfunctionalized alkyl glycoside. Alternately, at a concentration of 0.5 wt. %or less or 0.2 wt.
  • interfacial tension values for the organic carbonate salts described herein may be about 0.3 mN/m or less, or about 0.25 mN/m or less, or about 0.2 mN/m or less, or about 0.15 mN/m or less, or about 0.1 mN/m or less, or about 0.05 mN/m or less, or about 0.01 mN/m or less.
  • compositions of the present disclosure may be obtained by contacting an alkyl glycoside with an elevated pressure of carbon dioxide in the presence of a non-nucleophilic strong base (preferably an amidine, such as DBU or DBN) , and obtaining an organic carbonate salt comprising a cationic portion comprising the non-nucleophilic base in protonated form and an anionic portion that is a carbonate reaction product of the alkyl glycoside.
  • a non-nucleophilic strong base preferably an amidine, such as DBU or DBN
  • contacting the alkyl glycoside with the carbon dioxide may take place in an aprotic organic solvent (reaction solvent) under heating.
  • suitable aprotic organic solvents may include, for instance, dimethylformamide, dimethylsulfoxide, dimethylpropylene urea, the like, or any combination thereof.
  • heating may take place at a temperature above room temperature (25°C) up to about 100°C, or up to about 90°C, or up to about 80°C, up to about 70°C, or up to about 60°C.
  • Suitable elevated pressures of carbon dioxide may range from about 2 atm to about 10 atm, or about 2.5 atm to about 7.5 atm, or about 3 atm to about 5 atm, or about 4 atm to about 6 atm.
  • methods of the present disclosure may further comprise isolating the organic carbonate salt from the reaction solvent.
  • the organic carbonate salt may be isolated using techniques such as, but not limited to, filtering, settling, decanting, centrifuging, or any combination thereof.
  • the isolated organic carbonate salt may be further washed with a washing solvent to remove the reaction solvent.
  • suitable washing solvents may include those having a low boiling point and in which the organic carbon salt is insoluble but the reaction solvent is at least partially soluble.
  • suitable washing solvents may include, but are not limited to, hydrocarbon solvents such as hexane.
  • the organic carbonate salt may be further freeze dried or dried under vacuum and/or with heating to further remove the washing solvent, residual carbon dioxide, residual reaction solvent, or any combination thereof.
  • the organic carbonate salt may be further dissolved in an aqueous fluid.
  • Suitable aqueous fluids may include those specified above.
  • a concentration of the organic carbonate salt in the aqueous fluid may include those specified above.
  • the aqueous fluid may comprise at least one salt (e g , brine, an aqueous salt solution, seawater, and the like) .
  • compositions of the present disclosure may be utilized in any application in which surfactancy is desired.
  • the compositions may be utilized in recovering hydrocarbons from a subterranean formation, such as in conjunction with an enhanced oil recovery process.
  • the compositions may be introduced to a subterranean formation to promote emulsification of an oleaginous substance downhole or to promote de-emulsification of an existing emulsion downhole.
  • the compositions may be emulsified with an oleaginous substance prior to being introduced into a subterranean formation.
  • compositions may be utilized to change surface wetting characteristics (wettability) of a given surface downhole (e g , a formation matrix or a fracture surface within a subterranean formation) .
  • wettability surface wetting characteristics
  • Particular uses for the compositions and performance thereof may depend on the conditions present or anticipated to be present downhole.
  • compositions of the present disclosure may be used in conjunction with enhanced oil recovery (EOR) operations.
  • EOR enhanced oil recovery
  • the organic carbonate salts of the present disclosure may change surface wetting within a subterranean formation to promote recovery of hydrocarbons therefrom. For example, by changing the surface wetting characteristics of a subterranean formation, release of hydrocarbons from the formation matrix may take place more readily and/or the hydrocarbons may be mobilized toward a production well more readily.
  • the foregoing may be facilitated through a variety of mechanisms including oil swelling, viscosity reduction, and wettability alteration, for example.
  • the foregoing is typically referred to as the tertiary phase of hydrocarbon production, wherein one or more chemical or physical interactions are modified within the subterranean formation using an injected fluid to promote production.
  • the tertiary phase of hydrocarbon production is usually employed after initial production resulting from native reservoir pressurization (primary production) or induced reservoir pressurization (secondary production) has been exhausted.
  • primary production native reservoir pressurization
  • secondary production induced reservoir pressurization
  • Embodiments disclosed herein include:
  • compositions formed from alkyl glycosides comprise: an organic carbonate salt comprising an anionic portion that is a carbonate reaction product of an alkyl glycoside.
  • Methods for treating a subterranean formation comprise: providing the composition of A; and introducing the composition into a subterranean formation.
  • Methods for forming an organic carbonate salt of an alkyl glycoside comprise: contacting an alkyl glycoside with an elevated pressure of carbon dioxide in the presence of a non-nucleophilic base; and obtaining an organic carbonate salt comprising a cationic portion comprising the non-nucleophilic base in protonated form and an anionic portion that is a carbonate reaction product of the alkyl glycoside.
  • Embodiments A, B, and C may comprise one or more of the following additional embodiments in any combination.
  • Element 1 wherein the alkyl glycoside is an alkyl polyglycoside.
  • Element 2 wherein the alkyl polyglycoside comprises at least two monosaccharide units, one or more of the at least two monosaccharide units are functionalized with an organic carbonate group in salt form, and a terminal monosaccharide unit of the at least two monosaccharide units is alkylated.
  • Element 3 wherein the at least two monosaccharide units are linked by ⁇ -1, 4-glycosidic bonds.
  • Element 4 wherein the organic carbonate salt comprises a cation portion comprising a non-nucleophilic base in protonated form.
  • Element 5 wherein the non-nucleophilic base has a pK a of about 10 or greater.
  • Element 6 wherein the non-nucleophilic base comprises an amidine.
  • Element 7 wherein the cation portion comprises 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) in protonated form.
  • DBU 1, 8-diazabicyclo [5.4.0] undec-7-ene
  • Element 8 wherein the alkyl glycoside comprises a terminal alkyl group comprising about 4 to about 24 carbon atoms.
  • Element 9 wherein the carbonate reaction product comprises an organic carbonate group in salt form at a primary alcohol position of at least one monosaccharide unit of the alkyl glycoside.
  • composition further comprises an aqueous fluid in which the organic carbonate salt is dissolved.
  • Element 12 wherein the composition is introduced into the subterranean formation in conjunction with an enhanced hydrocarbon recovery process.
  • Element 13 wherein the composition contacts a salt-containing fluid in the subterranean formation, the aqueous fluid comprises at least one salt, or any combination thereof.
  • Element 14 wherein the method further comprises contacting the composition with an oleaginous substance in the subterranean formation; and emulsifying the oleaginous substance in the aqueous fluid in the presence of the organic carbonate salt.
  • Element 15 wherein the composition is emulsified with an oleaginous substance when introduced into the subterranean formation.
  • Element 16 wherein contacting takes place in an aprotic organic solvent under heating.
  • Element 17 wherein heating takes place at a temperature up to about 100°C.
  • Element 18 wherein the elevated pressure is about 3 atm to about 5 atm.
  • exemplary combinations applicable to A, B and C include, but are not limited to: 1 and 2, and 3; 1 and 2, and 4, 5, 6, or 7; 1 and 2, and 8; 1 and 2, and 9; 1 and 2, and 10; 1 and 2, and 10 and 11; 3, and 4, 5, 6, or 7; 3 and 8; 3 and 9; 3 and 10; 3, 10, and 11; 4, 5, 6, or 7, and 8; 4, 5, 6, or 7, and 9; 4, 5, 6, or 7, and 10; 4, 5, 6, or 7, and 10 and 11; 8 and 9; 8 and 10; 8, 10, and 11; 9 and 10; and 9-11.
  • any of the foregoing may be in further combination with one or more of 12-18.
  • Further exemplary combinations applicable to B include, but are not limited to, 12 and 13; 12 and 14; 12 and 15; and 13 and 14.
  • Further exemplary combinations applicable to C include, but are not limited to, 16 and 17; 16 and 18; 17 and 18; and 16-18.
  • a composition comprising:
  • an organic carbonate salt comprising an anionic portion that is a carbonate reaction product of an alkyl glycoside.
  • Clause 3 The composition of clause 2, wherein the alkyl polyglycoside comprises at least two monosaccharide units, one or more of the at least two monosaccharide units are functionalized with an organic carbonate group in salt form, and a terminal monosaccharide unit of the at least two monosaccharide units is alkylated.
  • Clause 4 The composition of clause 3, wherein the at least two monosaccharide units are linked by ⁇ -1, 4-glycosidic bonds.
  • Clause 5 The composition of any one of clauses 1-4, wherein the organic carbonate salt comprises a cation portion comprising a non-nucleophilic base in protonated form.
  • Clause 6 The composition of clause 5, wherein the non-nucleophilic base has a pK a of about 10 or greater.
  • Clause 7 The composition of clause 5 or clause 6, wherein the non-nucleophilic base comprises an amidine.
  • Clause 8 The composition of any one of clauses 5-7, wherein the cation portion comprises 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) in protonated form.
  • DBU 1, 8-diazabicyclo [5.4.0] undec-7-ene
  • Clause 10 The composition of any one of clauses 1-9, wherein the carbonate reaction product comprises an organic carbonate group in salt form at a primary alcohol position of at least one monosaccharide unit of the alkyl glycoside.
  • Clause 13 The method of clause 12, wherein the composition is introduced into the subterranean formation in conjunction with an enhanced hydrocarbon recovery process.
  • Clause 14 The method of clause 12 or clause 13, wherein the composition contacts a salt-containing fluid in the subterranean formation, the aqueous fluid comprises at least one salt, or any combination thereof.
  • Clause 15 The method of any one of clauses 12-14, further comprising:
  • Clause 16 The method of any one of clauses 12-14, wherein the composition is emulsified with an oleaginous substance when introduced into the subterranean formation.
  • a method comprising:
  • an organic carbonate salt comprising a cationic portion comprising the non-nucleophilic base in protonated form and an anionic portion that is a carbonate reaction product of the alkyl glycoside.
  • Clause 18 The method of clause 17, wherein contacting takes place in an aprotic organic solvent under heating.
  • Clause 19 The method of clause 18, wherein heating takes place at a temperature up to about 100°C.
  • Clause 20 The method of any one of clauses 17-19, wherein the elevated pressure is about 3 atm to about 5 atm.
  • the alkyl polyglycoside comprises at least two monosaccharide units, one or more of the at least two monosaccharide units are functionalized with an organic carbonate group in salt form, and a terminal monosaccharide unit of the at least two monosaccharide units is alkylated.
  • Clause 23 The method of clause 22, wherein the at least two monosaccharide units are linked by ⁇ -1, 4-glycosidic bonds.
  • Clause 24 The method of any one of clauses 17-23, wherein the non-nucleophilic base has a pK a of about 10 or greater.
  • Clause 25 The method of any one of clauses 17-24, wherein the non-nucleophilic base cation comprises an amidine.
  • Clause 26 The method of any one of clauses 17-25, wherein the cation portion comprises 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) in protonated form.
  • DBU 1,8-diazabicyclo [5.4.0] undec-7-ene
  • Clause 28 The method of any one of clauses 17-27, wherein the carbonate reaction product comprises an organic carbonate group in salt form at a primary alcohol position of at least one monosaccharide unit of the alkyl glycoside.
  • Clause 30 The method of clause 29, wherein the aqueous fluid comprises at least one salt.
  • FIG. 1 is a plot of comparative FTIR spectra of the alkyl polyglycoside and the alkyl polyglycoside carbonate salt reaction product. Compared to the alkyl polyglycoside starting material, the reaction product contained a peak near 1600 cm -1 that was broadened and contained new fine structure. The new peaks are characteristic of carbonate group introduction. Peaks related to adsorbed CO 2 were also evident near 2600 cm -1 .
  • FIG. 2 is a plot of comparative UV-VIS spectra of the alkyl polyglycoside and the alkyl polyglycoside carbonate salt reaction product. As shown, the UV-VIS absorbance increased following formation of the carbonate salt reaction product. The increased UV-VIS absorbance is believed to result from the DBU cation.
  • the carbonate salt reaction product was dissolved in high-salinity water having a total dissolved solids content of 57, 670 ppm (18, 300 ppm Na + , 650 ppm Ca 2+ , 2, 110 ppm Mg 2+ , 4, 290 ppm SO 4 2- , 32, 200 ppm Cl - , 120 ppm HCO 3 - ) at a concentration of 0.2 wt. %.
  • the solution remained transparent both at 25°C and 90°C, indicating that precipitation did not occur in the presence of the high salt concentration.
  • Emulsification Performance The foregoing aqueous solution of the carbonate salt reaction product in high-salinity water was combined with crude oil in a 1: 1 volume ratio and emulsified therewith by shaking the mixture by hand. Oil-in-water emulsions readily formed upon agitation, and the emulsions separated into discrete oil and water phases after standing for 30 minutes or less. Emulsions formed only from the high-salinity water and crude oil, in contrast, did not undergo de-emulsification within the same timeframe.
  • FIG. 3 is a plot of interfacial tension as a function of time for the alkyl glycoside and the alkyl glycoside carbonate salt reaction product. As shown, the alkyl polyglycoside carbonate salt reaction product had approximately a 10-fold lower interfacial tension than did the parent alkyl polyglycoside. In addition, the interfacial tension of the carbonate salt reaction product remained relatively constant with time, unlike the parent alkyl polyglycoside, which displayed increasing interfacial tension with time.
  • references in the appended claims to an apparatus or system or a component of an apparatus or system being adapted to, arranged to, capable of, configured to, enabled to, operable to, or operative to perform a particular function encompasses that apparatus, system, or component, whether or not it or that particular function is activated, turned on, or unlocked, as long as that apparatus, system, or component is so adapted, arranged, capable, configured, enabled, operable, or operative.
  • compositions described herein may be free of any component, or composition not expressly recited or disclosed herein. Any method may lack any step not recited or disclosed herein.
  • the term “comprising” is considered synonymous with the term “including.
  • composition, element or group of elements Whenever a method, composition, element or group of elements is preceded with the transitional phrase “comprising, ” it is understood that we also contemplate the same composition or group of elements with transitional phrases “consisting essentially of, ” “consisting of, ” “selected from the group of consisting of, ” or “is” preceding the recitation of the composition, element, or elements and vice versa.

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Abstract

Selon l'invention, des compositions comprenant un sel de carbonate organique ayant une partie anionique qui est un produit de réaction de carbonate d'un alkyl glycoside peuvent présenter des propriétés de tensioactif. Lorsqu'ils sont dissous dans un fluide aqueux, de tels sels de carbonate organique peuvent présenter des valeurs de tension interfaciale relativement faibles et rester tolérants à la présence de sels dans le fluide aqueux. À titre d'exemple non limitatif, des fluides aqueux contenant les sels de carbonate organique peuvent être introduits dans une formation souterraine, par exemple conjointement avec un processus de récupération assistée du pétrole.
PCT/CN2023/095941 2023-05-24 2023-05-24 Produits de réaction de carbonate d'alkyl glycosides et leurs procédés d'utilisation Pending WO2024239261A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5545731A (en) * 1992-04-02 1996-08-13 Henkel Kommanditgesellschaft Auf Aktien Alkyl and/or alkenyl oligoglycoside carbonates
WO2022192653A1 (fr) * 2021-03-12 2022-09-15 Aramco Services Company Procédé pour atténuer la réactivité vis-à-vis des acides pendant une stimulation par des acides de réservoirs riches en carbonates

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5545731A (en) * 1992-04-02 1996-08-13 Henkel Kommanditgesellschaft Auf Aktien Alkyl and/or alkenyl oligoglycoside carbonates
WO2022192653A1 (fr) * 2021-03-12 2022-09-15 Aramco Services Company Procédé pour atténuer la réactivité vis-à-vis des acides pendant une stimulation par des acides de réservoirs riches en carbonates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DOS SANTOS,VAGNER B. ET AL.: "Formation of isomers of anionic hemiesters of sugars and carbonic acid in aqueous medium", CARBOHYDRATE RESEARCH, vol. 428, 12 April 2016 (2016-04-12), XP029542296, DOI: 10.1016/j.carres.2016.04.007 *

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