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WO2025199102A1 - Compositions et procédés de tensioactifs dérivés d'alcool légèrement ramifiés pour nettoyage de surface dure - Google Patents

Compositions et procédés de tensioactifs dérivés d'alcool légèrement ramifiés pour nettoyage de surface dure

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Publication number
WO2025199102A1
WO2025199102A1 PCT/US2025/020371 US2025020371W WO2025199102A1 WO 2025199102 A1 WO2025199102 A1 WO 2025199102A1 US 2025020371 W US2025020371 W US 2025020371W WO 2025199102 A1 WO2025199102 A1 WO 2025199102A1
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WIPO (PCT)
Prior art keywords
surfactant
branch
alcohol
surfactants
detergent composition
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Pending
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PCT/US2025/020371
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English (en)
Inventor
Chunzhao Li
Travis A. Reine
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ExxonMobil Technology and Engineering Co
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ExxonMobil Technology and Engineering Co
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Publication of WO2025199102A1 publication Critical patent/WO2025199102A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/02—Preparation of ethers from oxiranes
    • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups

Definitions

  • This disclosure relates to a composition of matter and processes for producing the composition of matter including surfactants and detergent compositions exhibiting effective stain removal properties.
  • the processes to produce surfactants may include using a feed stream having lightly branched C13 oxo alcohols (LBAs) with surfactant precursors.
  • LBAs lightly branched C13 oxo alcohols
  • the lightly branched C13 oxo alcohols (LBAs) described herein exhibit differentiated branching and first branch distribution. Accordingly, the composition of matter and processes of this disclosure are especially useful for surfactant-based applications.
  • Surfactants are amphiphilic compounds that decrease the surface tension of two compositions at an interface.
  • the molecular structure of most commonly found surfactants typically consists of a combination of properties — a hydrophilic component and a hydrophobic component.
  • the differences in polarity between hydrophilic component and the hydrophobic component aid the solubilizing of insoluble or slightly chemicals (e.g., that would otherwise not solubilize or only partially solubilize in the absence of heat and/or surfactant).
  • Additional surfactants may be used to decrease the viscosity of a fluid phase or enhancing foaming properties of a fluid. Accordingly, surfactants may be implemented into a variety of consumer and industrial products, including, but not limited to, detergents, emulsifiers, cosmetics, pharmaceuticals, and dispersants.
  • Conventional surfactants may exhibit poor performance and solubility when employed for stain and grease removal. Ostensibly, branched surfactants have been found to be effective detergents for stain and grease removal, yet many of the conventional branched surfactants exhibit poor stain removal properties such as smearing. Therefore, there is currently a need for surfactants that exhibit good cleaning performance and stain and grease removal properties (e.g., on hard surfaces).
  • This disclosure relates to techniques for generating lightly branched oxo alcohols (LB As) (e.g., lightly branched C13 oxo alcohols) that have limited (e.g., light) branching (e.g., low branching index values) and a first branch distribution.
  • LB As lightly branched oxo alcohols
  • surfactants formed using the disclosed LB As may provide improved surfactant-based applications (e.g., use in detergents) in grease stain removal. Accordingly, it is presently recognized that it may be advantageous to develop techniques that produce surfactants having an alkoxy group derived from the LBA that exhibits limited branching and first branch distribution.
  • the techniques discussed herein include providing a mixture comprising butene and, optionally a small amount of propylene in the presence of a catalyst to generate lightly branched C12 olefins (LBOs). Further, the LBOs are hydroformylated in the presence of a hydroformylation catalyst to produce a lightly branched C13 oxo alcohol (LBA) composition.
  • LBA compositions described herein may have limited branching and a first branch distribution.
  • the LBA compositions may exhibit branching index (BI) values between about 1.0 and 1.9 (e.g., about 1.1, 1.2 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, or 1.9) and an average carbon number between about 12.0 and 14.0, such as about 12.5 and 13.5.
  • BI branching index
  • the average carbon number of the LBA compositions may be about 12.5, 12.75, 13, 13.25, or 13.5). While these are described as “C13 oxo alcohols” it should be noted that the 13 is an integer representing the average carbon number.
  • the conditions described herein may provide an LBA composition including a defined distribution of the first branch position (e.g., the first branch distribution), wherein the first branch position is determined relative to the hydroxyl group based on the overall LBA composition (e.g., about 10 to about 20% first branch at position two, about 20 to about 40% first branch at position three, about 5 to about 15% first branch at position four, and about 35 to about 55% first branch at position five and beyond (5&5+), as characterized by C13 NMR.
  • the overall LBA composition e.g., about 10 to about 20% first branch at position two, about 20 to about 40% first branch at position three, about 5 to about 15% first branch at position four, and about 35 to about 55% first branch at position five and beyond (5&5+
  • the branch distribution is discussed with respect to (e.g., counting from) to the oxygen atom (O) adjacent to the alkyl group (e.g., LB A derived alkyl group) of the surfactant, which is the oxygen atom linking the alkyl group to one or more alkoxy groups.
  • the disclosed techniques may include generating surfactants using the disclosed C13 oxo alcohol. It should be noted that the disclosed techniques may also be applied to other oxo alcohols, such as C Cincinnati oxo alcohols where n is 13, 15, and so on.
  • a reaction can be performed between the disclosed C13 oxo alcohol, or other C n oxo alcohol, and surfactant precursors (e.g., ethylene oxide, sulfur trioxide, or chlorosulfonic acid) in the presence of an optional catalyst to produce surfactants (e.g., alcohol derived sulfates, alcohol derived ether sulfates, or alcohol derived ethoxylates), respectively.
  • surfactants made from the disclosed LB exhibit a surprising performance when formulated as a hard surface cleaning composition relative to surfactants generated using conventional branched C13 alcohols or linear alcohols with an average of 12 to 14 carbons.
  • FIG. 1 is a flow diagram of a method for producing branched C13 oxo alcohols, in accordance with the present disclosure
  • FIG. 2 illustrates an example molecular structure of a branched C13 oxo alcohol, in accordance with the present disclosure
  • FIG. 3 is a flow diagram of a method for producing surfactants for hard surface cleaning compositions, in accordance with the present disclosure
  • FIG. 4 is a graph showing cleaning performance of various detergent compositions on hard surfaces; in accordance with the present disclosure.
  • FIG. 5 is a graph showing cleaning performance of various detergent compositions on hard surfaces, in accordance with the present disclosure.
  • FIG. 6 is a graph showing cleaning performance of various detergent compositions on hard surfaces, in accordance with the present disclosure.
  • weight percent (wt %) means percentage by weight.
  • a "carbon number” refers to the number of carbon atoms in a hydrocarbon.
  • a "Cx” hydrocarbon is one having x carbon atoms (i.e., carbon number of x)
  • a "Cx - Cy" or "Cx - y” hydrocarbon is one having from x to y carbon atoms.
  • alkane refers to non-aromatic saturated hydrocarbons with the general formula C n H(2n+2), where n is 1 or greater.
  • An alkane may be straight chained or branched. Examples of alkanes include methane, ethane, propane, butane, pentane, hexane, heptane and octane.
  • Alkane is intended to embrace all structural isomeric forms of an alkane. For example, butane encompasses n-butane and isobutane; pentane encompasses n-pentane, isopentane and neopentane.
  • olefin and “alkene,” are used interchangeably to refer to a branched or unbranched unsaturated hydrocarbon having one or more carbon-carbon double bonds.
  • a simple olefin comprises the general formula CnH(2n), where n is 2 or greater.
  • olefins include ethylene, propylene, butylene, pentene, hexene and heptene.
  • Olefin is intended to embrace all structural isomeric forms of an olefin. For example, butylene encompasses but-1- ene, (Z)-but-2- ene, etc.
  • reactor refers to any vessel(s) in which a chemical reaction occurs. Reactor includes both distinct reactors, as well as reaction zones within a single reactor apparatus and, as applicable, reactions zones across multiple reactors. For example, a single reactor may have multiple reaction zones.
  • branched refers to a hydrocarbon or hydrocarbyl group having a linear main carbon chain in which a hydrocarbyl side chain extends from the linear main carbon chain.
  • unbranched refers to a straight-chain hydrocarbon or hydrocarbyl group without side chain groups extending therefrom. More particularly, “lightly branched” refers to hydrocarbons having branches (e.g., monobranched, dibranched, tribranched). It should be noted that the NMR techniques discussed herein may determine composition based off the position of the chain.
  • LBO lightly branched olefin
  • first branch refers to the first hydrocarbyl side chain closest to the hydroxyl group extending from the linear main carbon chain.
  • second branch refers to the second hydrocarbyl side chain farthest from the hydroxyl group extending from the linear main carbon chain that is not the first branch.
  • Branch position refers to the position of the first branch along the main carbon chain, wherein the first CH2 group on the main chain bonded to the hydroxyl group is referred to as “position one.” Accordingly, the “branch position” of the first branch may be position one, position two, position three, position four, position 5, or position 5 and beyond (5&5+).
  • a “branching index” be determined using proton NMR based on the peak integral from the ppm range corresponding to methylene protons adjacent to the hydroxyl group, remaining aliphatic and hydroxyl protons and methyl protons (CH3).
  • a “branch position” may be determined using Carbon- 13 NMR ( 13 C NMR) based on the peak integral from the ppm range corresponding to the position of the first branch. It should be noted that the position of the first branch is distinguishable up to position 4. Branched C13 oxo alcohols having a first branch at position 5&5+ are not distinguishable. Similarly, the position of the second branch is indistinguishable due to complexities arising within 13 C NMR. It is to be understood that other techniques such as FT-IR, HPLC, GC, GC-MS might be applicable for the determination of one or more of the properties of the disclosed invention.
  • surfactant refers to amphiphilic compounds comprising a hydrophilic portion and a hydrophobic portion that tend to lower the surface tension at an interface between two components.
  • Surfactants are amphiphilic compounds comprising a hydrophilic portion and a hydrophobic portion that tend to lower the surface tension at an interface between two components.
  • surfactants may be used in a wide range of applications, which may include, for example, promoting solubility of an otherwise sparingly soluble material, lowering viscosity of a fluid phase, and promoting foaming of a fluid.
  • Surfactants may be found in a wide range of consumer and industrial products including, for example, soaps, detergents, cosmetics, pharmaceuticals, and dispersants.
  • Ionic functional groups that may be present in the hydrophilic portion of surfactants include, for example, sulfonates, sulfates, carboxylates, phosphates, quaternary ammonium groups, and the like.
  • Non-ionic hydrophilic portions may include functional groups or moieties bearing one or more heteroatoms that are capable of receiving hydrogen bonds, such as polyethers (e.g., ethoxylates).
  • Zwitterionic hydrophilic portions may include moieties such as betaines, sultaines, and related phospholipid compounds. It should be noted that “surfactants” or “amphiphiles” may be used interchangeably herein.
  • detergent composition refers to compositions and formulations designed for cleaning and removing stains from soiled materials.
  • examples of such compositions include, but are not limited to, all-purpose cleaning, laundry cleaning, fabric softeners, laundry additives, dry cleaning materials, laundry rinse additives, dish washing, hard surfaces, detergents in other materials.
  • the detergent compositions described herein may be formulated into various forms such as liquids, powders, gels, paste, bars, tablets, pouches, doses, etc.
  • a detergent composition 74 may include the surfactant 68 in combination with one or more additives, such as stabilizers, alkali ingredients, and additional surfactants (e.g., second surfactant, third surfactant).
  • hard surface cleaning composition refers to a detergent composition 74 that may be used to clean hard surfaces. It should be noted that “detergent composition”, “hard surface cleaning composition”, and “all-purpose cleaning composition” may be used interchangeably.
  • composition that is “substantially free” of/from a component may refer to a composition that includes less than about 0.5%, 0.25%, 0.1%, 0.05%, or 0.01%, or even 0%, by weight of the composition, of the component.
  • C13 oxo alcohol to produce surfactants.
  • the C13 oxo alcohol may also be utilized to produce surfactants including additional nonionic surfactants, anionic surfactants, cationic surfactants, etc.
  • the disclosed C13 oxo alcohol could also be used to produce esters, and acrylates, accordingly.
  • FIGS. 1-3 wherein like numerals are used to designate like parts throughout.
  • FIG. 1 illustrates a flow diagram of method 10 for producing lightly branched C13 oxo alcohols (LB As) in accordance with certain embodiments of the present disclosure.
  • the method 10 includes providing butene 12 (e.g., a butene feedstock, wherein the butene feedstock may include isomers of butene (e.g., 1 -butene, 2-butene, isobutylene) and, optionally, propylene 14 (e.g., a propylene feedstock) in the presence of a catalyst 16 to produce an LBO composition 20.
  • butene 12 e.g., a butene feedstock
  • the butene feedstock may include isomers of butene (e.g., 1 -butene, 2-butene, isobutylene) and, optionally, propylene 14 (e.g., a propylene feedstock) in the presence of a catalyst 16 to produce an LBO composition 20.
  • propylene 14 e
  • butene 12 and the optional propylene 14 are contacted in the presence of a catalyst 16 such as certain conditions described in US 11,905,227 B2, US 11,312,669 B2, WO2022233875A1, WO2022233876A1, which are incorporated herein by reference.
  • contacting butene 12 and, optionally, propylene 14 in the presence of the catalyst 16 may include providing a flow of a feedstock (e.g., butene feed flow rate and the optional propylene feed flow rate) including the butene 12 and the optional propylene 14 over a solid support formed of the catalyst 16 into a reactor.
  • a feedstock e.g., butene feed flow rate and the optional propylene feed flow rate
  • the catalyst 16 may be stored or otherwise contained in a reaction vessel, and the feedstock including butene 12 and propylene 14 may be provided, flowed, or otherwise directed into the reaction vessel including the catalyst 16.
  • the reactor may be a single fixed bed reactor or preferably a multi -tubular reactor.
  • Solid acid catalysts suitable for producing olefin oligomers having an average branching index of about 2.2 or less, particularly for C12 olefin oligomers having an average branching index of about 2.2 or less, such as an average branching index of about 1.0 to about 1.9 may include, for example, zeolite catalysts having an MTT or TON framework, including unmodified zeolite catalysts having these frameworks. Suitable examples may include, for instance, ZSM-22, ZSM- 23, ZSM-57, and SAPO-11. Such solid acid catalysts and other zeolite catalysts may be modified by steaming, modified with an organic acid, modified with a transition metal, modified with coke, impregnated with NiO, or any combination thereof.
  • Suitable modification conditions are described further below. Although already suitable for producing an average branching index of about 2.2 or less, such modifications to these zeolite catalysts may further improve selectivity and/or decrease the average branching index, as explained further below. Such solid acid catalysts may afford selectivity for forming C10-C13 olefin oligomers when exposed to suitable oligomerization reaction conditions.
  • Suitable zeolite catalysts can be prepared from extrudates (about 1 wt. % to about 90 wt. % binder and about 10 wt. % to about 99 wt. % zeolite) or from zeolite crystal seeds.
  • suitable binders may include silica, alumina, zirconia, titania, silica-alumina, metal oxides, the like, and mixtures thereof.
  • Particular zeolite catalysts may be crystalline and have an aspect ratio of about 1 to about 5, alternatively about 2 to about 4, with a width of less than about 0.1 microns and a length of less than about 0.3 microns.
  • the zeolite catalysts Prior to use, the zeolite catalysts may be calcined in air at about 425 °C to about 650°C for about 1 hour to overnight.
  • Particular zeolite catalyst examples may include, for example, a Si/Al ZSM-23 catalyst having no amine treatment and a Si: A12 molar ratio of about 20 to about 60, or about 25 to about 55, or about 30 to about 50, or about 30 to 45.
  • Si/Al ZSM-23 catalysts may be prepared as described in US Patents 4,076,842 and 5,332,566, each of which is incorporated herein by reference.
  • the zeolite catalyst may be a Si/Al/Ti ZSM-23 catalyst having no amine treatment and a Si:A12 molar ratio of about 20 to about 60, or about 25 to about 55, or about 30 to about 50 and a Ti:Al molar ratio of about 0.1 to about 3, or about 0.2 to about 2, or about 0.3 to about 1.
  • Si/Al/Ti ZSM-23 catalysts may be prepared as described in the foregoing US Patents. A combination of the two ZSM-23 catalyst types may be used.
  • the zeolite catalyst may have a Si: A12 molar ratio of about 30: 1 to about 200: 1 and comprise about 0.1 wt. % to about 5 wt.
  • zeolite catalysts described herein may be prepared as described in WO2022233879A1, which is incorporated herein by reference.
  • Oligomerization may be carried out in a fixed bed reactor, a packed bed reactor, a tubular reactor, a fluidized bed reactor, a slurry reactor, a continuous catalyst regeneration reactor, or any combination thereof.
  • Suitable oligomerization reaction conditions may include a reaction temperature of about 80°C to about 350°C, or about 90°C to about 350°C, or about 150°C to about 350°C, or about 170°C to about 310°C.
  • Oligomerization may take place at a pressure ranging from about 50 bar to about 300 bar, or about 60 bar to about 150 bar, or about 70 bar to about 120 bar.
  • Oligomerization may be carried out at a WHSV ranging from about 2 hr 1 to 70 hr 1 , or about 5 hr 1 to about 30 hr 1 , or about 5 hr 1 to about 10 hr 1 , or about 10 hr' 1 to about 15 hr’ 1 , or about 15 hr 1 to about 20 hr’ 1 , or about 20 hr' 1 to 30 hr' 1 .
  • certain zeolite catalysts particularly those having an MTT framework, such as ZSM-23 or modified ZSM-23, may promote formation of C10-C13 olefin oligomers with relatively good selectivity, while affording a branching index for at least C12 olefins of about 1.7 or less particularly about 1.1 to about 1.7.
  • the reaction vessel may include a solid acid component that promotes formation of lightly branched olefins having a range of methyl group and double bond positions.
  • the resulting LBO composition 20 is separated (e.g., fractionated) to produce higher olefins 24 (e.g., olefins heavier than C12, such as Ci6, C20, C24, etc.), lighter olefins 34 (e.g., olefins lighter than C12, such as C4 feed, C8), and lightly branched olefins (LBO) 26 (e.g., lightly branched C12 olefins including one or more of linear dodecenes, mono-alkyl (e.g., mono-methyl, mono-ethyl, mono-w-propyl, mono-z-propyl) branched isododecenes, dibranched isododecenes,
  • fractionating may include providing, flowing, or otherwise directing for fractionation for separation using suitable techniques, such as distillation and other techniques understood by a person of ordinary skill in the art.
  • suitable techniques such as distillation and other techniques understood by a person of ordinary skill in the art.
  • the LBOs 26 exhibit a branching index in the range of 1.0 to 1.9, more preferably between 1.1 to 1.8, 1.2 to 1.7, 1.3 to 1.7.
  • LBOs 26 are contacted in the presence of a catalyst 28 that causes the LBOs 26 to undergo hydroformylation (i.e., a reaction in the presence of carbon monoxide in hydrogen with a catalyst), thereby producing the LBA 32 (i.e., a primary alcohol).
  • the LBAs may include advantageous properties, or combinations of properties, such as branching index for use as a feedstock for producing surfactants.
  • the catalyst 28 may include a suitable transition metal complex (e.g., cobalt-based catalysts, ruthenium-based catalysts, iridium-based catalyst, etc.) or suitable compound that facilitates hydroformylation.
  • contacting the LBO 26 in the presence of the catalyst 28 and/or catalyst platform 28 may include providing a flow of a feedstock (e.g., LBO feed flow rate) over the catalyst 28 and/or catalyst platform 28.
  • a feedstock e.g., LBO feed flow rate
  • the catalyst 28 and/or catalyst platform 28 may be stored or otherwise contained in a reaction vessel, and the feedstock including LBO 26 may be provided, flowed, or otherwise directed into the reaction vessel including the catalyst 28 and/or catalyst platform 28.
  • LBO 26 may be contacted in a reactor with a homogeneous catalyst 28.
  • the catalyst 28 may be dissolved in a reaction medium in the reactor.
  • LBO 26 is initially converted into an aldehyde. Subsequently, the aldehyde is reduced via hydrogenation, producing lightly branched C13 oxo alcohol (LBA) composition 32.
  • LBA lightly branched C13 oxo alcohol
  • the aldehyde can undergo hydrogenation during the hydroformylation process.
  • the aldehyde may be provided, flowed or otherwise directed to an additional catalyst (i.e., different than the catalyst 28) for hydrogenation after hydroformylation.
  • the catalyst may be a heterogenous catalyst.
  • the LBAs 32 may include advantageous properties, or combinations of properties, such as branching index for use as a feedstock for producing surfactants, or overall weight percent of isomer composition.
  • Suitable catalysts for promoting hydroformylation of one or more lightly branched olefins may include a metal carbonyl complex, such as a carbon monoxide complex of a transition metal of Groups 8-10 of the Periodic Table.
  • a metal carbonyl complex such as a carbon monoxide complex of a transition metal of Groups 8-10 of the Periodic Table.
  • Group 9 metals cobalt and rhodium are best known for their hydroformylation activity, but other suitable metals in Groups 8-10 may include palladium, iridium, ruthenium and platinum.
  • suitable catalysts may include HRh(CO)(PR3)3, HRh(CO)2(PR3), HRh(CO)[P(OR)3]3, Rh(CH 3 COCH2COCH 3 )(CO)2, Rh6(CO)16, [Rh(norbomadiene)(PPh3)2 + [PF6]-,
  • Particularly suitable cobalt hydroformylation catalysts may include unmodified HCo(CO)4 or Co2(CO)8.
  • Inorganic salts and catalyst precursors such as Rh2O3, Pd(NO3)2 and Rh(NO3)3, may be used, as may halides such as, for example, RhC13»3H2O.
  • a nickel catalyst in the presence of dimethylamine may be used.
  • Olefin oligomers not undergoing hydroformylation may undergo subsequent reduction into paraffins once the hydroformylation reaction product is converted into a primary alcohol. Paraffins may be separated from the primary alcohols following reduction or maintained therewith.
  • Reducing may comprise hydrogenating the hydroformylation reaction product in particular embodiments of the present disclosure.
  • Hydrogenation may comprise exposing the hydroformylation reaction product to hydrogen and a hydrogenation catalyst (i.e., catalytic hydrogenation conditions using a catalyst comprising Fe, Co, Ni, Ru, Rh, Cr, Mo, Pd, Os, Ir, or Pt, preferably supported on an inorganic substrate, and a hydrogen partial pressure of, for example, about 5 MPa to about 20 MPa, and a reaction temperature up to about 180°C).
  • Catalytic hydrogenation may remove any residual carbon-carbon unsaturation present in the hydroformylation reaction product, as well as reduce at least a portion of the aldehyde groups into primary alcohols.
  • Hydride reduction may complete the reduction of the aldehyde moieties into a primary alcohol moiety.
  • reduction may comprise exposing the hydroformylation reaction product to catalytic hydrogenation to produce a reduced hydroformylation reaction product.
  • Solvents or diluents are not necessary when conducting the hydroformylation reaction according to the disclosure herein, but may optionally be present in any amount.
  • suitable solvents or diluents may include, but are not limited to, alkane solvents, polar protic solvents, polar aprotic solvents, chlorinated solvents and aromatic solvents.
  • up to about 10 wt. % water may be added to control byproduct formation under the hydroformylation reaction conditions. Without being bound by theory or mechanism, water may hinder the formation of aldol condensates and other heavy reaction products.
  • composition of the LB As 32 are described below. In general, the compositions described below describe the properties of the LB As 32.
  • FIG. 2 illustrates a molecular structure 40 of the LBA 32
  • compositional information regarding the LBA 32 may be obtained using C 13 NMR.
  • the resulting LBA 32 exhibits two branches: a first branch 44 and a second branch 46.
  • the branch e.g., hydrocarbyl groups
  • the branch may be methyl groups, ethyl groups, propyl groups, etc.
  • the “first branch” refers to the branch closest to the hydroxyl group 42 on the main carbon chain of the LBA 32.
  • the “second branch” refers to the branch positioned further from the hydroxyl group 42 as compared to the first branch.
  • the numerical position of the branch of the LBA 32 is counted from the hydroxyl group 42.
  • the position of the first branch 44 may be at position two 50, position three 52, or position four 54.
  • the first branch may also be at positions beyond position five 56a, such as position six 56b, position seven 56c, position eight 56d, position nine 56e, position ten 56f, or position eleven 56g.
  • position five and beyond may include position five 56a, position six 56b, position seven 56c, position eight 56d, position nine 56e, position ten 56f, or position eleven 56g, and may be collectively referred to as position 56.
  • position 56 may be distinguishable in C 13 NMR up to position four 54.
  • LB As 32 having a first branch 44 at position five 56 and beyond are not distinguishable.
  • the position of the second branch is indistinguishable due to complexities arising within 13 C NMR.
  • the position of the second branch 46 as illustrated in FIG. 2 is an example and can exhibit positions including position 5 and beyond of the LBA 32. However, the average carbon number is measurable.
  • the techniques described herein may provide an advantage such as facilitating the determination the position of the first branch within the LBAs 32.
  • the LBAs 32 exhibit an average number of carbons between about 12.5 and about 13.5.
  • the average number of carbons may range between 12.7 and 13.3, 12.9 and 13.1, about 12.6, about 12.8, about 13.0, about 13.2, or about 13.4.
  • the LBAs 32 exhibit a branching index between about 1.0 and about 1.9.
  • the branching index may range between about 1.3 and about 1.7, or 1.4 and 1.6.
  • the disclosed LBAs 32 are also defined by a specific range of first branch position distribution (position 2 ,3, 4, 5&5+) based on the C13 NMR analysis of the first branch carbons.
  • % distribution of LBAs 32 exhibiting a first branch at position two may range between about 10 to about 20%
  • a first branch at position three may range between about 20 to about 40%
  • a first branch at position four may range between about 5 to about 15%
  • a first branch at position 5&5+ 56 may range between about 35% to about 55%.
  • the majority of the first branch is on a position higher than position 2.
  • greater than or equal to 80% of the first branch may be at position 3 or higher
  • greater than or equal to 50% of the first branch may be at position 4 or higher
  • greater than or equal to 40% of the first branch may be at position 5 or higher.
  • Table 1 shows properties of an example of the disclosed LBAs 32 and a baseline composition alcohol.
  • Table 1 shows the disclosed branched C13 alcohol (e.g., Experimental Material 1 (Exp. Mat. 1 oxo alcohol or Exp. Mat. 1)) corresponding to the disclosed LBAs 32.
  • “Exp. Mat. 1 oxo alcohol” and “Exp. Mat. 1” may be used interchangeably herein.
  • Table 1 shows comparative branched C13 alcohols, (e.g., Comparative 1 oxo alcohol, Comparative 2 linear Cl 2- 18 alcohol, Comparative 3 linear Cl 2- 14 alcohol, or Comparative 1, Comparative 2, Comparative 3).
  • Comparative 1 or “Comparative 1 oxo alcohol” may be used interchangeably.
  • Table 1 shows properties of the disclosed LB As 32 (Exp. Mat. 1) and comparative alcohols (e.g., Comparative 1, Comparative 2 and Comparative 3).
  • Table 1 shows the properties of the disclosed LBAs 32 and comparative alcohols (e.g., Comparative 1, Comparative 2 and Comparative 3), wherein the properties include branching index and distribution of the first branch position.
  • Comparative 2 is a natural linear C12-C18 alcohol with an average carbon number of 12.6
  • Comparative 3 is a natural linear C12-C14 alcohol with an average carbon number of 12.5.
  • linear with respect to alcohols refers to alcohols having a branching index that is 0.
  • Exp. Mat. 1 has a lower BI than Comparative 1.
  • the percentage of molecules that have their first branch at position 2 for Exp. Mat. 1 is less than Comparative 1.
  • the percentage of their molecules exhibit their first branch at position 5&5+ for Exp. Mat. 1 is greater than Comparative 1.
  • % distribution of LBAs 32 exhibiting a first branch at position two 50 may range between about 10% and about 20%, about 12% and about 18%, about 14% and about 16%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, about 19%, or about 20%.
  • the % distribution of the LBAs 32 at exhibiting a first branch at position three 52 may range between about 20% and about 40%, about 22% and about 38%, about 24% and about 36%, about 26% and about 34%, about 28% and about 32%, about 20%, about 22%, about 24%, about 26%, about 28%, about 30%, about 32%, about 34%, about 36%, about 38%, or about 40%.
  • the % distribution of the LBAs 32 at exhibiting a first branch at position four 54 may range between about 5% and about 15%, about 7% and about 13%, about 9% and about 11%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, or about 15%.
  • the % distribution of the LB As 32 at exhibiting a first branch at position 5&5+ 56 may range between about 35% and about 55%, about 37% and about 53%, about 39% and about 51%, about 41% and about 49%, about 43% and about 47%, about 35%, about 37%, about 39%, about 41%, about 43%, about 45%, about 47%, about 49%, about 51%, about 53%, or about 55%. Accordingly, the % distribution of the first branch being at position 5&5+ may be greater than the % distribution of the first branch being at position 4, position 3, or position 2.
  • the BI of the LB As 32 may range between about 1.0 to about 1.9.
  • the BI of LB As 32 may range between about 1.3 and about 1.7, about 1.4 and about 1.6, about 1.0, about 1.1, about 1.2, about 1.3, about 1.4, about 1.5, about 1.6, about 1.7, about 1.8, or about 1.9.
  • LBAs 32 exhibit an include advantageous properties, or combinations of properties, such as branching index, distribution of first branch position, or for use as a feedstock for producing surfactants. That is, the disclosed techniques demonstrate that lightly branched alcohols 32 may provide better cleaning performance than comparative alcohols. In some embodiments, the % distribution of the LBAs 32 at exhibiting a 3, 4-di substituted branch may range less than 6%, less than 5%, less than 4%, less than 3%, less than 2%, or less than 1%.
  • FIG. 3 illustrates a flow diagram of a method 60 for producing surfactants 68 based on LBAs 32 and a surfactant precursor 62, in accordance with certain embodiments of the present disclosure.
  • the method 60 includes, at block 66, contacting the surfactant precursor 62 and the LBAs 32 in the presence of an optional catalyst 64.
  • block 66 may include performing an ethoxylation reaction using the disclosed LBAs 32 and the surfactant precursor 62 (e.g., ethylene oxide and its derivatives, such as propylene oxide, butylene oxide), producing surfactant 68 (e.g., alcohol alkoxylates including alcohol derived ethoxylates)).
  • the surfactant precursor 62 e.g., ethylene oxide and its derivatives, such as propylene oxide, butylene oxide
  • surfactant 68 e.g., alcohol alkoxylates including alcohol derived ethoxylates
  • surfactant 68 is represented by R-X, where R is the hydrocarbon moiety of the LBAs 32 (i.e. excluding -OH) and X is a hydrophilic moiety (e.g., surfactant precursor 62). More specifically, the surfactant 68 has the following formula:
  • R-0-(A0) -X where R is a lightly branched hydrocarbon (e.g., alkyl group) derived from the LBA 32, AO is an alkoxylate (e.g., ethylene oxide (EO) C2H4-O, propylene oxide (PO) C3H6-O, butylene oxide (BO) C4H8-O, or a combination thereof) and X is a hydrogen, a sulfate, or other functional groups described herein or understood by one of ordinary skill in the art for surfactants.
  • EO ethylene oxide
  • PO propylene oxide
  • BO butylene oxide
  • AO may be a combination of alkoxylates and, thus, may be represented as (EO)i(PO) m (BO) n , where 1, m, or n is 0 or greater (e.g., 0.5, 1, 1.5, 2, and so on, such as ranging from 0 to 2, from 0 to 4, from 0 to 6, from 0 to 8, from 0 to 10, from 0 to 12, or from 0 to 15).
  • 1, m, or n are an integer value for an individual molecule
  • 1, m, or n may be represented as a fraction with respect to a combination of multiple molecules (e.g., 1, m, and n may be expressed as the average 1, m, and n values with respect to the surfactant 68 or other product).
  • the surfactant 68 includes an alkyl group, a repeating unit (e.g., one or more alkoxy groups), and a terminal group, X. It should be noted that (EO), (PO), or (BO) could be any ordered combination.
  • the alkyl group may have a BI between 1.3 and 1.7 and other properties described herein.
  • the branch distribution of the first branch may be described with respect to the oxygen atom (O) that is adjacent to the alkyl group, which is the oxygen atom linking the alkyl group to one or more alkoxy groups.
  • the LBAs 32 may be converted into anionic surfactants.
  • anionic surfactants such as alcohol derived sulfates. It should be noted that such techniques may be applied to the disclosed LBAs 32.
  • the LBAs 32 may be converted into nonionic surfactants in accordance with disclosure US6963014.
  • block 66 may include performing a sulfation reaction using the disclosed LBAs 32 and the surfactant precursor 62 (e.g., sulfur trioxide and its derivatives, such as chlorosulfonic acid, sulfuric acid, sulfamic acid), thereby producing the surfactant 68 that includes a sulfate (e.g., alcohol-derived sulfates).
  • a sulfate e.g., alcohol-derived sulfates
  • alcohol derived ethoxylates may have similar structural features to the alcohol-derived sulfates except for their non-ionic hydrophilic group.
  • the surfactants 68 may include advantageous properties, or combinations of properties, such as low BI values (e.g., minimal branching) and hard surface cleaning performance.
  • contacting LBA 32 and surfactant precursor 62 in the presence of the optional catalyst 64 may include providing a flow of a feedstock (e.g., LBA feed flow rate and surfactant precursor feed flow rate) including the LBA 32 and surfactant precursor 62 associated with a particular reaction (e.g., precursors associated with alcohol derived ethoxylates and/or precursors associated with alcohol derived alcohol derived sulfates/ether sulfates, respectively) in the presence of the optional catalyst 64.
  • a feedstock e.g., LBA feed flow rate and surfactant precursor feed flow rate
  • the optional catalyst 64 may be stored or otherwise contained in a reaction vessel, and the feedstock including LBA 32 and surfactant precursor 62 may be provided, flowed, or otherwise directed into the reaction vessel including the catalyst 64.
  • the surfactant 68 (e.g., alcohol derived ethoxylate, alcohol ether sulfates, or alcohol derived sulfate) is formed through a reaction between a surfactant precursor 62 and the LBA 32.
  • the resulting surfactant 68 can be utilized as detergent compositions due to its low BI values (e.g., minimal branching) and hard surface cleaning performance.
  • BI values e.g., minimal branching
  • the surfactants 68 may include repeating ethoxy (EO) units.
  • the surfactant e.g., nonionic surfactant
  • the disclosed LBA 32 may include EO units ranging from about one to about 10, such as about two to about eight, to about three to about seven, about four to about six, such as about seven to about nine, about one, about two, about three, about four, about five, about six, about seven, about eight, about nine, or about 10.
  • the surfactants 68 may be utilized in hard surface cleaning applications alone and/or in combination with additional components (e.g., additives) to generate alternative compositions.
  • additional components e.g., additives
  • one or more additives 72 may be provided to surfactants 68.
  • the additives 72 may include stabilizers/chelating agents (e.g., EDTA, tetrasodium glutamate diacetate (GLDA)), builders (e.g., sodium citrate), pH adjusters and buffering methods (e.g., NaOH, HC1, KOH, carboxylic acids, carbonates such as sodium carbonates, bicarbonates, combinations thereof), additional surfactants, neutralization agents (e.g., monoethanolamine), or a combination thereof.
  • the detergent compositions 74 include about 0.5% to about 90% by weight of surfactant 68.
  • the disclosed surfactants 68 exhibit properties such as an average carbon number ranging from about 12.5 and 13.5, branching index ranging from about 1.0 to about 1.9 (e.g., 1.3 to about 1.7), and a defined distribution of the first branch position as dictated by the physical structure of LB As 32, which may improve hard surface cleaning performance when combined with additives 72 to produce detergent composition 74. That is, the surfactants 68 generated using the disclosed LBAs 32 generally exhibit properties (e.g., branching index, distribution of the first branch position, average carbon number) associated with the disclosed LBAs 32.
  • the X of R-X may be selected from the group consisting of sulfates, sulfonates, amine oxides, polyoxyalkylene, polyhydroxy moieties, phosphate esters, polyphosphate esters, sulfosuccinates, polyalkoxylated carboxylates, amine oxide, glycerol ethers, glycerol ether sulfates, glycerol esters, glycerol ester sulfates, polyglycerol ethers, polyglycerol ether sulfates, glycerol ethers, glycerol ether sulfates, sulfonated fatty acids, and mixtures thereof.
  • X may be a sulfate, ether sulfate, or ethoxylate.
  • the resulting anionic surfactant may exist in an acid form.
  • the acid form may be neutralized using a neutralization agent to form a surfactant salt.
  • Example neutralization agents for neutralization of the acid form include metal counterion bases, such as hydroxides, e.g., NaOH, KOH, or. Additionally or alternatively, suitable neutralization agents may also include ammonia, amines, or alkanolamines.
  • alkanolamines include monoethanolamine (MEA), diethanolamine, triethanolamine, and other linear or branched alkanolamines known in the art; suitable alkanolamines include 2-amino-l -propanol, 1 -aminopropanol, monoisopropanolamine, or l-amino-3 -propanol.
  • neutralization using an amine may be carried out to any sufficient degree of completion.
  • the degree of completion may be 100%, 80%, 70%, 60%, 50%, and so on.
  • part of the anionic surfactant mix may be neutralized with sodium or potassium and part of the anionic surfactant mix may be neutralized with amines or alkanolamines.
  • a portion of the carbon content of the surfactant 68 may be derived from renewable sources.
  • renewable sources such as used cooking oil, vegetable oil, palm kernel oil, com/sugar cane ethanol etc.
  • a “renewable sources” refers to a feedstock that contains renewable carbon content, which may be assessed through ASTM D6866, which allows the determination of the renewable carbon content of materials using radiocarbon analysis by accelerator mass spectrometry, liquid scintillation counting, and isotope mass spectrometry.
  • the detergent compositions 74 may include one or more additives 72 (e.g., a second surfactant, a third surfactant) as selected from the group consisting of anionic surfactants, nonionic surfactants, cationic surfactants, zwitterionic surfactants, amphoteric surfactants, ampholytic surfactants, and mixtures thereof.
  • the additional surfactant may be a detersive surfactant, which those of ordinary skill in the art will understand to encompass any surfactant or mixture of surfactants that provide cleaning (e.g., hard surface cleaning), stain removing, or laundering benefit to soiled material. It should be noted that surfactants may be used interchangeably with additives.
  • the surfactant 68 is an anionic surfactant (e.g., alcohol derived sulfates, such as alcohol ether sulfates).
  • the surfactant 68 may include at least one alcohol derived sulfate, wherein the alcohol derived sulfate has a branching index ranging from about 1.0 and 1.9 (e.g., about 1.1, 1.2 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, or 1.9).
  • the surfactant 68 is a nonionic surfactant (e.g., alcohol derived ethoxylates).
  • the surfactant 68 may include at least one alcohol derived ethoxylate, wherein the alcohol derived ethoxylate has a branching index ranging from about 1.0 and 1.9 (e.g., about 1.1, 1.2 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, or 1.9).
  • the detergent composition 74 may include surfactant 68 (e.g., at least one surfactant 68, such as one or more surfactants 68, two or more surfactants 68, three or more surfactants 68, four or more surfactants 68), wherein a total weight percentage of surfactants of the disclosed surfactants 68 based on the total weight of the detergent composition 74 may range between about 0.1% to about 99% by weight, about 0.1 to about 50%, about 0.01% to about 40%, about 0.01% to about 30%, about 0.01% to about 20%, or about 0.01% to about 10%.
  • surfactant 68 e.g., at least one surfactant 68, such as one or more surfactants 68, two or more surfactants 68, three or more surfactants 68, four or more surfactants 68
  • a total weight percentage of surfactants of the disclosed surfactants 68 based on the total weight of the detergent composition 74 may range between about 0.1% to about 99% by weight, about
  • the total weight percentage of surfactants 68 within a detergent composition 74 may be about may be about 0.5%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, or about 10%.
  • the detergent composition 74 may include at least one surfactant 68 that is an anionic surfactant (e.g., alcohol derived sulfates, such as alcohol ether sulfates).
  • the detergent composition 74 may include at least one surfactant 68 that is a nonionic surfactant (e.g., alcohol derived ethoxylates).
  • the detergent composition 74 may include a total weight percentage of additives 72 (e.g., neutralizing agents, pH adjusters, stabilizers/chelating agents, solvents) may range from about 0% to about 100% by weight, about 0.01% to about 95%, about 0.01% to about 90%, about 0.01% to about 80%, 0.01% to about 70% 0.01% to about 60%, 0.01% to about 50%, about 0.01% to about 40%, about 0.01% to about 30%, about 0.01% to about 20%, or about 0.01% to about 10%.
  • additives 72 e.g., neutralizing agents, pH adjusters, stabilizers/chelating agents, solvents
  • the total percentage of additives 72 within a detergent composition 74 may be about 0.1%, about 0.2%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, about O.9%, about 1%, about 1.5%, about 2%, about 2.5%, about 3%, about 3.5%, about 4%, about 4.5%, about 5%, about 5.5%, about 6%, about 6.5%, about 7%, about 7.5%, about 8%, about 8.5%, about 9%, about 9.5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or about 100%.
  • additives 72 e.g., neutralizing agents, pH adjusters, stabilizers/chelating agents, solvents
  • the detergent compositions 74 may include solvents, such as water and/or organic solvents (e.g., alcohols, ethers, glycol ethers, combinations thereof).
  • solvents such as water and/or organic solvents (e.g., alcohols, ethers, glycol ethers, combinations thereof).
  • the amount of solvent e.g., water
  • the total amount of solvent may be about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or about 100%.
  • the detergent composition may include a pH ranging from about 6.0 to about 14.0, about 7.0 to about 9.0, such as about 7.2 to about 8.8, about 7.4 to about 8.6, about 7.6 to about 8.4, about 7.8 to about 8.2, about 7.8 to about 8.2, about 7.0, about 7.2, about 7.4, about 7.6, about 7.8, about 8.0, about 8.2, about 8.4, about 8.6, about 8.8, or about 9.0.
  • the reaction product was then added slowly to a chilled 25% sodium methoxide solution in anhydrous methanol to convert the reaction product from an acid sulfate form to a sodium sulfate salt form. Additional anhydrous methanol is added when it is desirable to maintain neutralization product fluidity. The resulting mixture is cloudy, pale yellow in color, fluid, and mixing well. The product was mixed thoroughly for another two hours until a roughly 5% aqueous solution pH is stable between 9. 0 and 10.0. The reaction mixture is then poured into a plastic tray to evaporate the methanol in fume hood. The product was then put in a vacuum oven to further remove the solvents. The final dried product is off-white, soft solid. Alcohol ether sulfates may be prepared using alcohol ethoxylate and sulfamic acid in accordance with disclosure US2452943.
  • LBAs 32 for hard surface cleaning applications. It is presently recognized that the disclosed surfactants 68 (e.g., alcohol sulfates, alcohol ether sulfates, and alcohol ethoxylates) made from LBAs 32 demonstrate improved cleaning performance, as described in more detail below.
  • surfactants 68 e.g., alcohol sulfates, alcohol ether sulfates, and alcohol ethoxylates
  • Tables 2-4 shows exemplary detergent compositions 74 that include surfactants 68 generated from the disclosed LBAs 32.
  • Table 2 shows four different samples (e.g., Model A, Test 1, Test 2, Test 3), which correspond to different detergent compositions 74 that include a combination of an anionic surfactant, a nonionic surfactant, and additives.
  • alcohols from Table 1 e.g., Exp. Mat. 1, Comparative 1, Comparative 2, and Comparative 3
  • surfactants e.g., anionic surfactants, nonionic surfactant
  • the disclosed LBA 32 e.g., Exp. Mat.
  • an anionic surfactant 68 e.g., alcohol ether sulfate (AES) of Exp. Mat. 1
  • nonionic surfactants 68 e.g., alcohol ethoxylate EO7 of Exp. Mat. 1, alcohol ethoxylate EO9 of Exp. Mat. 1.
  • comparative alcohols of Table 1 e.g., Comparative 1, Comparative 2 and Comparative 3 were utilized to generate surfactants (e.g., Comparative 1 b-C13 EO7, Comparative 2 C12-C18 alcohol ethoxylate EO7, Comparative 3 C12-C14 AES).
  • EO# represents the number of ethoxy (EO) units within an individual surfactant. That is, EO9/9EO represents a surfactant including 9 EO units, while EO7/7EO represents a surfactant including 7 EO units.
  • EO9/9EO represents a surfactant including 9 EO units
  • EO7/7EO represents a surfactant including 7 EO units.
  • Table 2 shows exemplary detergent compositions 74 that include surfactants 68 generated from the disclosed LB As 32.
  • Table 2 shows that the pH for all of the detergent compositions 74 exhibit a pH ranging from about 7.8 to about 8.2.
  • the pH of the detergent compositions 74 was adjusted with 30% hydrochloric acid (HC1) or monoethanolamine to about 8. The four samples were subsequently evaluated for their cleaning performance on hard surfaces for removal of fat on tile.
  • HC1 hydrochloric acid
  • monoethanolamine monoethanolamine
  • test formula is based on the Industrie notion Kbperpractic und Waschstoff (IKW) standard for all-purpose cleaner formulations (i.e., hard surface cleaning composition, hard surface cleaner) with a water hardness of 249 parts per million (ppm) CaCO3.
  • a scrub-tester “TQC Sheen-machine” is used for the test.
  • the test substrate is a 30cm x 30cm floor tile baked with peanut oil, kaolin and special black 4 (Degussa) diluted with propanol and aged.
  • a sample e.g., Model A, Test 1, Test, 2, Test 3
  • the evaluation of cleaning performance was performed via visual assessment and obtaining rating scores (e.g., cleaning performance values) by five panelists, where each sample had four replicates to generate a total of 20 readings for each of the samples.
  • the rating scores are presented in FIGS. 4-6 and are based on the average of the 20 readings with a score ranging between 0 and 10, where 10 represents 100% fat cleaning (i.e., clean) and 0 represent 0% fat cleaning (i.e., dirty).
  • FIG. 4 is a graph showing cleaning performance values of various detergent compositions on hard surfaces of Table 2.
  • each of the detergent compositions include a combination of an anionic surfactant and a nonionic surfactant.
  • FIG. 4 demonstrates that detergent compositions 74 formed using the disclosed LB A 32 as anionic surfactant 68 or nonionic surfactant 68 (e.g., Test 1, Test 2, Test 3) perform better than Model A.
  • Detergent compositions 74 generated using the disclosed LB A 32 exhibit a cleaning performance score ranging from about 2.5 to about 10, such as about 3 to about 9, about 4 to about 8, about 5 to about 7, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, or about 10.
  • Model A includes a combination of an anionic surfactant and a nonionic surfactant, wherein the anionic surfactant is a C12-C14 AES surfactant generated from the Comparative 3 alcohol of Table 1 and the nonionic surfactant is a C12-C18 alcohol ethoxylate generated from Comparative 2 alcohol of Table 1.
  • Test 1 includes an anionic surfactant 68 (e.g., AES) generated from the LBA 32 and the same nonionic surfactant as Model A.
  • Test 1 exhibits a better cleaning performance (e.g., higher cleaning performance values) than Model A, indicating that a detergent composition 74 including the AES surfactant 68 generated using the disclosed LBA 32 is more effective at cleaning.
  • This data demonstrates that lightly branched alcohols derived alcohol ether sulfate (Exp. Mat. 1 with branching index of 1.53) are more effective at cleaning than surfactants generated using linear alcohols derived alcohol ether sulfate (Comparative 3).
  • Test 2 includes the same anionic surfactant as Model A (e.g., C12-C14 AES surfactant generated from the Comparative 3 alcohol), but the nonionic surfactant is an alcohol ethoxylate EO7 surfactant 68 generated using the disclosed LBA 32 (i.e., Exp. Mat. 1). Although the Comparative 2 alcohols exhibits an average carbon number (12.6) and number of EO units (EO7) that is comparable to Exp. Mat. 1 (average carbon number from 12.5 to 13.5 and EO7), Test 2 exhibits a better cleaning performance than Model A. This data demonstrates that lightly branched alcohols (Exp. Mat. 1 with branching index of 1.53) derived alcohol ethoxylates are more effective at cleaning than surfactants generated using linear alcohols derived alcohol ethoxylate (Comparative 2).
  • Model A e.g., C12-C14 AES surfactant generated from the Comparative 3 alcohol
  • the nonionic surfactant is an alcohol ethoxylate EO7 surfact
  • Test 3 includes the anionic surfactant as Model A (e.g., C12-C14 AES surfactant generated from the Comparative 3 alcohol), but the nonionic surfactant is an alcohol ethoxylate EO9 surfactant 68 generated using the disclosed LBA 32 (i.e., Exp. Mat. 1). Test 3 also performs better than Model A, indicating that the light branching of Exp. Mat. 1 is more effective than natural linear alcohols (Comparative 2). It should be noted that the difference in performance between Test 2 and Test 3 may be associated with the difference in the number of EO units in the nonionic surfactants for each respective test. For example, Test 2’s nonionic surfactant 68 includes seven EO units, while Test 3’s nonionic surfactant includes nine EO units.
  • Model A e.g., C12-C14 AES surfactant generated from the Comparative 3 alcohol
  • Test 3 also performs better than Model A, indicating that the light branching of Exp. Mat. 1 is more effective than
  • Table 3 shows four different samples (e.g., Model B, Test 4, Test 5, Test 6), which correspond to different detergent compositions 74 that include a combination of an anionic surfactant, a nonionic surfactant, and additives.
  • alcohols from Table 1 e.g., Exp. Mat. 1, Comparative 1, Comparative 2 were utilized to generate surfactants (e.g., anionic surfactants, nonionic surfactant).
  • LAS linear alkylbenzene sulfonate
  • Table 3 shows that the pH for all of the detergent compositions 74 that include surfactants 68 generated using the disclosed LBA 32 (i.e., Exp. Mat. 1) exhibit a pH ranging from about 7.8 to about 8.2.
  • the pH of the detergent compositions 74 was adjusted with 30% hydrochloric acid (HC1) or monoethanolamine to about 8. The four samples were subsequently evaluated for their cleaning performance on hard surfaces for removal of fat on tile, which is demonstrated in FIG. 5.
  • Table 3 shows exemplary detergent compositions 74 that include surfactants 68 generated from the disclosed LB As 32.
  • FIG. 5 is a graph showing cleaning performance values of various detergent compositions on hard surfaces of Table 3.
  • each of the detergent compositions include a combination of an anionic surfactant and a nonionic surfactant, where the anionic surfactant is the same across all four samples (LAS).
  • FIG. 4 demonstrates that detergent compositions 74 that include using the nonionic surfactants generated from Exp. Mat. 1. (e.g., Test 4, Test 5, perform better than Model B and Test 6.
  • detergent compositions 74 generated using the disclosed LBA 32 may exhibit a cleaning performance value ranging from about 4 to about 10, such as about 5 to about 9, about 6 to about 8, about 4, about 5, about 6, about 7, about 8, about 9, or about 10.
  • the difference in performance can be attributed to the structural differences for a type of alcohol used to generate a particular surfactant.
  • the nonionic surfactant (C12-C18 alcohol ethoxylate EO7) in Model B was made using the Comparative 2 alcohol (i.e., linear alcohol), while the nonionic surfactants in Test 4 and Test 5 were made using the Exp. Mat. 1.
  • the Comparative 2 alcohols exhibits an average carbon number (12.6) and number of EO units (EO7) that is comparable to Exp. Mat. 1 (average carbon number from 12.5 to 13.5 and EO7)
  • Test 4 performs better than Model B.
  • Test 5 performs better than Model B as well. Accordingly, the difference in the branching index and first branch position distribution between the alcohols used to generate the surfactants in Model B and Test 4/Test 5 indicate that lightly branched alcohols provide improved cleaning benefits compared to linear alcohols.
  • Test 4 The effect of branching index on cleaning performance is profound when comparing Test 4 and Test 5 with Test 6.
  • the nonionic surfactants 68 of Test 4 and Test 5 were generated using Exp. Mat. 1 with a branching index of 1.53, while the nonionic surfactant of Test 6 was generated using Comparative 1 with a branching index of 2.08.
  • the nonionic surfactant in Test 6 is comparable in chain length (e.g., 13 carbons) and number of EO units relative to the nonionic surfactant in Test 4.
  • Test 4 outperforms Test 6, where Test 4 exhibits a ranking score of about 5.5, and Test 6 exhibits a ranking score of about 3.75.
  • branched surfactants would be more effective at cleaning fat.
  • having relatively fewer branches at position two 50 and more branches at 4 and beyond may advantageously provide an improved cleaning performance.
  • these results demonstrate that the disclosed lightly branched alcohols (branching index 1.53) that exhibit a first branch distribution as demonstrated in Table 1 exhibit better cleaning performance (e.g., higher cleaning performance value) than highly branched alcohols (branching index 2.08).
  • having relatively fewer branches at position 2 and more branches at 4 and beyond may provide the improved cleaning performance.
  • Test 4 and Test 5 may be associated with the difference in the number of EO units in the nonionic surfactants for each respective test.
  • Test 4’s nonionic surfactant 68 includes seven EO units
  • Test 5’s nonionic surfactant includes nine EO units.
  • FIG. 5 demonstrates that lightly branched alcohols exhibit better cleaning performance than linear and highly branched alcohols.
  • Table 4 shows five different samples (e.g., Model C2, Test 7, Test 8, Test 9), which correspond to different detergent compositions 74 that include a combination of a nonionic surfactant and additives.
  • alcohols from Table 1 e.g., Exp. Mat. 1, Comparative 1, Comparative 2 were utilized to generate surfactants (e.g., anionic surfactants, nonionic surfactant).
  • additional comparatives were explored as nonionic surfactants (e.g., Comparative 1, Comparative 2).
  • Table 4 shows that the pH for the detergent compositions 74 that include surfactants 68 generated using the disclosed LBA 32 (i.e., Exp. Mat.
  • Table 4 shows exemplary detergent compositions 74 that include surfactants 68 generated from the disclosed LB As 32.
  • FIG. 6 is a graph showing cleaning performance of various detergent compositions on hard surfaces of Table 4.
  • each of the detergent compositions 74 of Table 4 include a combination of nonionic surfactant and additives.
  • FIG. 6 demonstrates that detergent compositions 74 that include the nonionic surfactants generated from Exp. Mat. 1. (e.g., Test 7, Test 8) perform better than the comparative samples.
  • detergent compositions 74 generated using the disclosed LBA 32 may exhibit a cleaning performance value that is greater than 6.
  • the cleaning performance value may range from about 6 to about 10, such as about 7 to about 9, about 6, about 7, about 8, about 9, or about 10.
  • the difference in cleaning performance can be attributed to the branching index and first branch distribution for a respective alcohol used to generate a particular surfactant.
  • the nonionic surfactant in Model C2 (C12-C18 alcohol ethoxylate EO7) was generated using the Comparative 2 alcohol (natural linear).
  • Test 7 which includes the nonionic surfactant 68 (e.g., alcohol ethoxylate EO7 of Exp. Mat. 1), exhibits better cleaning performance than and Model C2.
  • these results indicate that light branching and branch distribution in alcohols may improve cleaning performance of surfactants 68 relative to alcohols that are lightly branched or linear.
  • Test 8 which includes the nonionic surfactant 68 (e.g., alcohol ethoxylate EO9 of Exp. Mat. 1) is comparable to C2.
  • Test 7 and Test 8 also exhibit higher ranking scores than Test 9, which includes the nonionic surfactant generated using the highly branched alcohol (e.g., Comparative 1 with branching index of 2.08).
  • highly branched surfactants would be more effective at cleaning fat.
  • LBA 32 has fewer branches at position two 50 relative to Comparative 1
  • LBA 32 has more branches at position 5&5+ 56 relative to Comparative 1 (as demonstrated in Table 1).
  • Test 7 may be associated with the difference in the number of EO units in the nonionic surfactants for each respective test.
  • Test 7’s nonionic surfactant 68 includes seven EO units
  • Test 8’s nonionic surfactant includes nine EO units.
  • an increasing number EO units may be associated with an increase in the hydrophilic content within an individual surfactant, thereby leading to a reduction in the cleaning performance.
  • Tables 2-4 and FIGS. 4-6 demonstrate that the disclosed LBAs 32, when formed as surfactants 68 and formulated as detergent compositions 74, are more effective at cleaning than alcohols that are linear, very lightly branched, or highly branched.
  • the present disclosure is directed to techniques for producing lightly branched alcohols (LBAs) using butene and an optional propylene and subsequently utilizing the lightly branched alcohols and reacting it with surfactant precursors to produce surfactants.
  • LBAs lightly branched alcohols
  • a surfactant precursor feedstock in the presence of the LBA may produce a surfactant stream having certain physical properties, such as limited branching and first branch distribution that are useful for surfactant-based applications such as hard surface cleaning applications.
  • the disclosed alcohol ethoxylate surfactant and alcohol ether sulfate surfactant may exhibit a good balance of cleaning properties for stain and grease removal.
  • the surfactants may be formulated to generate detergent compositions that exhibit good cleaning performance on hard surfaces, which is attributed to the physical properties of the LBAs (e.g., branching index, average carbon number, number of ethoxy units).
  • the disclosed surfactants and detergent compositions described herein may be used in a variety of consumer and industrial products, including, but not limited to, detergents, emulsifiers, cosmetics, pharmaceuticals, dispersants, home and personal care areas like hand and auto dishwashing, hard surface cleaning, body washing, shampoo and industrial applications such as textile, agriculture, emulsion polymerization, metal working fluids.
  • Embodiment 1 A detergent composition, including: 0.1 to 99 weight percent (wt. %) one or more alcohol derived surfactants having the chemical formula:
  • R-O-((EO)i-(PO) m -(BO) n )-X wherein X is H or an anionic head group; wherein 1, m, and n range from 0 to 12; wherein EO is ethylene oxide, PO is propylene oxide, and BO is butylene oxide; wherein R is an alkyl group; and wherein the alkyl group has a branching index between about 1.3 and about 1.7 and an average carbon number between about 12.5 and about 13.5, and wherein the alkyl group is linked to one or more alkoxy groups via an oxygen atom; and one or more additives.
  • Embodiment 2 The detergent composition of the preceding claim, wherein about 10% to about 20% of a respective alkyl group of the one or more alcohol derived surfactants have a first branch at position 2 counting from the oxygen atom.
  • Embodiment 3 The detergent composition of any preceding claim, wherein greater than about 40% of a respective alkyl groups of the one or more alcohol derived surfactants have a first branch at position 5 or higher counting from the oxygen atom.
  • Embodiment 4 The detergent composition of any preceding claim, wherein greater than about 80% of a respective alkyl groups of the one or more alcohol derived surfactants have a first branch at position 3 or higher counting from the oxygen atom.
  • Embodiment 5 The detergent composition of any preceding claim, wherein the one or more alcohol derived surfactants comprises alcohol ethoxylates.
  • Embodiment 6 The detergent composition of any preceding claim, wherein the one or more alkoxy groups are seven to nine ethoxy groups.
  • Embodiment 7 The detergent composition of any preceding claim, wherein the one or more alcohol derived surfactants comprises alcohol ether sulfates.
  • Embodiment 8 The detergent composition of any preceding claim, wherein 100 wt. % of the detergent composition comprises about 0.01 wt. % to about 90 wt. % of the one or more additives.
  • Embodiment 9 The detergent composition of any preceding claim, wherein about 10% to about 20% of a respective alkyl group of the one or more alcohol derived surfactants have a first branch at position 2 counting from the oxygen atom; and wherein greater than about 40% of a respective alkyl groups of the one or more alcohol derived surfactants have a first branch at position 5 or higher counting from the oxygen atom.
  • Embodiment 10 The detergent composition of any preceding claim, wherein greater than about 50% of a respective alkyl groups of the one or more alcohol derived surfactants have a first branch at position 4 or higher counting from the oxygen atom.
  • Embodiment 11 A method, comprising providing a butene feedstock.
  • the method includes generating higher olefins by contacting the butene feedstock in the presence of a catalyst.
  • the method further includes fractionating the higher olefins to obtain lightly branched olefins.
  • the method also includes hydroformylating, hydrogenating, and fractionating the lightly branched olefins to produce an alcohol composition, wherein the alcohol composition has a branching index between about 1.3 and about 1.7 and an average carbon number between about 12.5 and about 13.5.
  • the method includes providing a surfactant precursor.
  • the method also includes generating a surfactant by contacting the alcohol composition with the surfactant precursor optionally in the presence of a catalyst.
  • Embodiment 12 The method of the preceding claim, wherein the surfactant is a nonionic surfactant or anionic surfactant.
  • Embodiment 13 The method of any preceding claim, further comprising providing one or more additives to the surfactant to generate a detergent composition.
  • Embodiment 14 The method of any preceding claim, wherein the surfactant has a branching index of ranging from about 1.3 to about 1.7.
  • Embodiment 15 The method of any preceding claim, wherein the surfactant has the chemical formula:
  • Embodiment 16 The method of any preceding claim, wherein greater than about 50% of a respective alkyl groups of the surfactant has a first branch at position 4 or higher counting from the oxygen atom.
  • Embodiment 17 The method of any preceding claim, wherein the one or more additives comprise one or more surfactants, solvents, pH adjusters, stabilizers, neutralizing agents, or a combination thereof.
  • Embodiment 18 A detergent composition, including: 0.1 to 99 wt. % a mixture of lightly branched alcohol derived surfactants having the formula:
  • R-O-((EO)i-(PO) m -(BO) n )-X wherein X is H or an anionic head group; wherein 1, m, and n range from 0 to 12; wherein EO is ethylene oxide, PO is propylene oxide, and BO is butylene oxide; and wherein R is an alkyl group having a branching index between about 1.3 and about 1.7, wherein an average carbon number of the alkyl group is between about 12.5 and about 13.5, wherein about 10% to 20% of the mixture has a first branch at position 2 counting from an oxygen atom linking the alkyl group to one or more alkoxy groups, wherein greater than 35% of the mixture has the first branch at position 5&5+ counting from the oxygen atom linking the alkyl group to one or more alkoxy groups; and one or more additives.
  • Embodiment 19 The detergent composition of the preceding claim, wherein about 20% to about 30% of the mixture has the first branch at position 3 counting from the oxygen atom linking the alkyl group to one or more alkoxy groups.
  • Embodiment 20 The detergent composition of any preceding claim, wherein greater than 10% of the mixture has the first branch at position 4 counting from the oxygen atom linking the alkyl group to one or more alkoxy groups.

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Abstract

L'invention concerne une composition détergente comprenant de 0,1 à 99% en poids d'un ou de plusieurs tensioactifs dérivés d'alcool ayant la formule chimique : R-O-((EO)i-(PO)m-(BO)n)-X, dans laquelle X est H ou un groupe de tête anionique, 1, m et n allant de 0 à 12, EO étant l'oxyde d'éthylène, PO étant l'oxyde de propylène, et BO étant l'oxyde de butylène, R étant un groupe alkyle, et le groupe alkyle ayant un indice de ramification entre environ 1,3 et environ 1,7 et un nombre moyen de carbone entre environ 12,5 et environ 13,5, et le groupe alkyle étant lié à un ou plusieurs groupes alcoxy par l'intermédiaire d'un atome d'oxygène et un ou plusieurs additifs.
PCT/US2025/020371 2024-03-19 2025-03-18 Compositions et procédés de tensioactifs dérivés d'alcool légèrement ramifiés pour nettoyage de surface dure Pending WO2025199102A1 (fr)

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