Compositions and methods of lightly branched alcohol derived surfactants for hard surface cleaning

Abstract

Provided herein is a detergent composition including 0.1 to 99 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.

Description

COMPOSITIONS AND METHODS OF LIGHTLY BRANCHED ALCOHOL DERIVED SURFACTANTS FOR HARD SURFACE CLEANINGCROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to and the benefit of U.S. Provisional Application No. 63 / 567,231, filed on March 19, 2024, U.S. Provisional Application No. 63 / 772,986, filed on March 17, 2025, and U.S. Provisional Application No. 63 / 773,024 filed on March 17, 2025, the disclosures of which are incorporated herein by reference in their entireties.FIELD

[0002] 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. In particular, the processes to produce surfactants may include using a feed stream having lightly branched C13 oxo alcohols (LBAs) with surfactant precursors. In general, 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.BACKGROUND

[0003] 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.

[0004] Conventional surfactants (e.g., linear 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 iscurrently a need for surfactants that exhibit good cleaning performance and stain and grease removal properties (e.g., on hard surfaces).SUMMARY

[0005] A summary of certain embodiments disclosed herein is set forth below. It should be understood that these aspects are presented merely to provide the reader with a brief summary of these certain embodiments and that these aspects are not intended to limit the scope of this disclosure. Indeed, this disclosure may encompass a variety of aspects that may not be set forth below. As discussed above, it is desirable to generate surfactants having good cleaning performance and stain removal properties. Moreover, it is desirable to develop surfactants that provide good cleaning performance (e.g., grease stain removal).

[0006] 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. It is presently recognized that 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. The LBA compositions described herein may have limited branching and a first branch distribution. For example, 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. For example, 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. Further, 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. In discussing the surfactant, 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.

[0007] In some embodiments, 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„ oxo alcohols where n is 13, 15, and so on. In any case, a reaction can be performed between the disclosed C13 oxo alcohol, or other Cnoxo 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. The surfactants made from the disclosed LB As 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.

[0008] These and other features and attributes of the present disclosure and their advantageous applications and / or uses will be apparent from the detailed description which follows.BRIEF DESCRIPTION OF THE DRAWINGS

[0009] To assist those of ordinary skill in the relevant art in making and using the subject matter hereof, reference is made to the appended drawings, wherein:

[0010] FIG. 1 is a flow diagram of a method for producing branched C13 oxo alcohols, in accordance with the present disclosure;

[0011] FIG. 2 illustrates an example molecular structure of a branched C13 oxo alcohol, in accordance with the present disclosure;

[0012] FIG. 3 is a flow diagram of a method for producing surfactants for hard surface cleaning compositions, in accordance with the present disclosure;

[0013] FIG. 4 is a graph showing cleaning performance of various detergent compositions on hard surfaces; in accordance with the present disclosure;

[0014] FIG. 5 is a graph showing cleaning performance of various detergent compositions on hard surfaces, in accordance with the present disclosure; and

[0015] FIG. 6 is a graph showing cleaning performance of various detergent compositions on hard surfaces, in accordance with the present disclosure.DETAILED DESCRIPTION

[0016] One or more specific embodiments of the present disclosure will be described below. In an effort to provide a concise description of these embodiments, all features of an actual implementation may not be described in the specification. It should be appreciated that in the development of any such actual implementation, as in any engineering or design project, numerous implementation-specific decisions must be made to achieve the developers’ specific goals, such as compliance with system-related and business-related constraints, which may vary from one implementation to another. Moreover, it should be appreciated that such a development effort might be complex and time consuming, but would nevertheless be a routine undertaking of design, fabrication, and manufacture for those of ordinary skill having the benefit of this disclosure.

[0017] When introducing elements of various embodiments of the present disclosure, the articles “a,” “an,” “the,” and “said” are intended to mean that there are one or more of the elements. The terms “comprising,” “including,” and “having” are intended to be inclusive and mean that there may be additional elements other than the listed elements. All numerical values within the detailed description herein are modified by “about” the indicated value, and take into account experimental error and variations that would be expected by a person having ordinary skill in the art. For example, “about” or “approximately” may refer to ±0.5%, ±1%, ±2, ±5%, ±10%, or ±15%. Numerical ranges used herein include the numbers recited in the range. For example, the numerical range “from 1 wt % to 10 wt %” includes 1 wt % and 10 wt % within the recited range.

[0018] 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.

[0019] The term “and / or” as used in a phrase such as “A and / or B” herein is intended to include “A and B,” “A or B,” “A,” and “B .”

[0020] The term “weight percent (wt %)” means percentage by weight.

[0021] As used herein, a "carbon number" refers to the number of carbon atoms in a hydrocarbon. Likewise, a "Cx" hydrocarbon is one having x carbon atoms (i.e., carbon number of x), and a "Cx - Cy" or "Cx - y" hydrocarbon is one having from x to y carbon atoms.

[0022] The term "alkane" refers to non-aromatic saturated hydrocarbons with the general formula CnH(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.

[0023] The term "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. Examples of 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.

[0024] The term “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.

[0025] The terms “branched”, “lightly branched”, and “branched hydrocarbon” refer 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. The term “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.

[0026] The term “lightly branched olefin (LBO)” refers to an alkenic hydrocarbon bearing a carbon-carbon double bond within the main carbon chain. While side chain branches are present in an LBO, the branching is minimal (e.g., greater than or equal to one side branch, such as one to three branches, or one side branch, two side branches, or three side branches with an average branch of 1.5 branch per molecule) in a given LBO sample.

[0027] The term “first branch” refers to the first hydrocarbyl side chain closest to the hydroxyl group extending from the linear main carbon chain. The term “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.

[0028] The term “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+).

[0029] In general, 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 (13C 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 within13C 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.

[0030] The term “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. As such, 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 mayinclude moieties such as betaines, sultaines, and related phospholipid compounds. It should be noted that “surfactants” or “amphiphiles” may be used interchangeably herein.

[0031] The term or phrase “detergent composition” or 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. For example, 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).

[0032] The term “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.

[0033] As referred to herein, “substantially free of’ or “substantially free from” refers to either the complete absence of a component or includes a minimal amount of the component, such as an impurity or unintended byproduct of another ingredient. For example, a 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.

[0034] It should be noted that the disclosed techniques describe 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.

[0035] Reference is now made to the embodiments illustrated in FIGS. 1-3, wherein like numerals are used to designate like parts throughout.Lightly Branched Alcohols

[0036] 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. As shown, themethod 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.

[0037] Referring to the method 10, at block 18, 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. In some embodiments 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. For example, 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. In some embodiments, the reactor may be a single fixed bed reactor or preferably a multi -tubular reactor.

[0038] 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.

[0039] Suitable zeolite catalysts, such as ZSM-23, 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. Examples of suitable binders may include silica, alumina, zirconia, titania, silica-alumina, metal oxides, the like, and mixtures thereof. Particular zeolite catalysts may be crystalline andhave 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. 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.

[0040] 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. Alternatively, 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. In still other examples, 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. % transition metal and about 0.1 wt. % to about 3.3 wt. % framework Al-O. In general, preparation of the zeolite catalysts described herein may be prepared as described in WO2022233879A1, which is incorporated herein by reference.

[0041] 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.

[0042] Oligomerization may be carried out at a WHSV ranging from about 2 hr1to 70 hr1, or about 5 hr1to about 30 hr1, or about 5 hr1to about 10 hr1, or about 10 hr'1to about 15 hr’1, or about 15 hr1to about 20 hr’1, or about 20 hr'1to 30 hr'1. Surprisingly, 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.

[0043] More specifically, 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.

[0044] Referring to the method 10, at block 22, 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, multi -branched isododecenes, and trace amounts of dienes and / or cyclic alkanes). In general, 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. Accordingly, 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.

[0045] Referring to the method 10, at block 30, 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). As described here, the LBAs may include advantageous properties, or combinations of properties, such as branching index for use as a feedstock for producing surfactants.

[0046] 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. In a similar manner as described with respect to block 12, 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. For example, 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. In another embodiment, referring to block 30, LBO 26 may be contacted in a reactor with a homogeneous catalyst 28. For example, the catalyst 28 may be dissolved in a reaction medium in the reactor.

[0047] During the process of hydroformylation, LBO 26 is initially converted into an aldehyde. Subsequently, the aldehyde is reduced via hydrogenation, producing lightly branched C13 oxo alcohol (LBA) composition 32. In general, the aldehyde can undergo hydrogenation during the hydroformylation process. In another embodiment, 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 includeadvantageous properties, or combinations of properties, such as branching index for use as a feedstock for producing surfactants, or overall weight percent of isomer composition.

[0048] 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. Of the 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. By way of nonlimiting example, suitable catalysts may include HRh(CO)(PR3)3, HRh(CO)2(PR3), HRh(CO)[P(OR)3]3, Rh(CH3COCH2COCH3)(CO)2, Rh6(CO)16, [Rh(norbomadiene)(PPh3)2 + [PF6]-,[Rh(C)3(PPh3)2]+ [BPh4]-, RhCl(CO)(PEt3)2, [RhCl(cyclooctadiene)]2, [Rh(CO)3(PR3)2]+ BPh4-, [Rh(CO)3(PR3)2]+ PF6-, HCo(CO)4, Ru3(CO)12, [RuH(CO)(acetonitrile)2(PPh3)3 + [BF4]-, PtC12 (cyclooctadiene), [Ir(CO)3 (PPh3)] + [PF6]-, or [HPt(PEt3)3]+ [PF6]-. Other suitable catalysts may include, for example, HCo(CO)4, Co2(CO)8, HCo(CO)3(POR)3 (R = alkyl or aryl), HCo(CO)3(PR3) (R = alkyl or aryl), and Co(II)X2 (X = anionic ligand, such as carboxylate, sulfate, halide, alkoxide, amide, and the like). 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. In exemplary embodiments, a nickel catalyst in the presence of dimethylamine may be used.

[0049] 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.

[0050] 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, either conducted alone or in combination with catalytichydrogenation, may complete the reduction of the aldehyde moieties into a primary alcohol moiety. In an example process configuration, reduction may comprise exposing the hydroformylation reaction product to catalytic hydrogenation to produce a reduced hydroformylation reaction product.

[0051] Solvents or diluents are not necessary when conducting the hydroformylation reaction according to the disclosure herein, but may optionally be present in any amount. When used, suitable solvents or diluents may include, but are not limited to, alkane solvents, polar protic solvents, polar aprotic solvents, chlorinated solvents and aromatic solvents. In a particular example, 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.

[0052] Several non-limiting examples of the composition of the LB As 32 are described below. In general, the compositions described below describe the properties of the LB As 32.

[0053] By way of example, FIG. 2 illustrates a molecular structure 40 of the LBA 32, in accordance with the embodiments of the present disclosure, compositional information regarding the LBA 32 (e.g., produced in accordance with block 30 of the method 10 in FIG. 1) may be obtained using C13NMR. The resulting LBA 32 exhibits two branches: a first branch 44 and a second branch 46. It should be noted that the branch (e.g., hydrocarbyl groups) may be methyl groups, ethyl groups, propyl groups, etc. As described herein, 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. In general, 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. As referred to herein, position five and beyond (e.g., 5&5+) 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. It should be noted that the position of the first branch 44 may be distinguishable in C13NMR up to position four 54. As such, 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 within13C NMR. It should be noted that the position of the second branch 46 as illustratedin 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.

[0054] It is presently recognized that the techniques described herein may provide an advantage such as facilitating the determination the position of the first branch within the LBAs 32. In general, the LBAs 32 exhibit an average number of carbons between about 12.5 and about 13.5. For example, 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. Further, the LBAs 32 exhibit a branching index between about 1.0 and about 1.9. For example, 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. For example, % 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%, and a first branch at position 5&5+ 56 may range between about 35% to about 55%. In some embodiments, the majority of the first branch is on a position higher than position 2. For example, 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, or greater than or equal to 40% of the first branch may be at position 5 or higher.Lightly Branched Alcohols

[0055] With the foregoing in mind, 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. It should be noted that “Exp. Mat. 1 oxo alcohol” and “Exp. Mat. 1” may be used interchangeably herein. Further, 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). It should be noted that “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).

[0056] 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. It should be noted that Comparative 2 is a natural linear C12-C18 alcohol with an average carbon number of 12.6, and Comparative 3 is a natural linear C12-C14 alcohol with an average carbon number of 12.5. As referred to herein, “linear” with respect to alcohols refers to alcohols having a branching index that is 0. In general, Exp. Mat. 1 has a lower BI than Comparative 1. Additionally, the percentage of molecules that have their first branch at position 2 for Exp. Mat. 1 is less than Comparative 1. Further, the percentage of their molecules exhibit their first branch at position 5&5+ for Exp. Mat. 1 is greater than Comparative 1.

[0057] In particular, % 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%, about9% 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%. Further, 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.

[0058] Additionally, the BI of the LB As 32 may range between about 1.0 to about 1.9. For example, 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.

[0059] 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%.Detergent Compositions

[0060] With the foregoing in mind, 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. As shown, the method 60 includes, at block 66, contacting the surfactant precursor 62 and the LBAs 32 in the presence of an optional catalyst 64. For example, 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 structure of 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) -Xwhere 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. In some embodiments, 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). While 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. That is, the relative order of (EO), (PO), and (BO) in ((EO)i-(PO)m-(BO)n) is not intended to suggest a particular order of (EO), (PO), (BO), or a combination thereof. Furthermore, it should be noted that R-O-(AO)-X or R-O-((EO)i-(PO)m-(BO)n)-Xmay be used interchangeably. It should be noted that the discussion herein related to the branching index and the first branch distribution may be applied to R. 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.

[0061] In some embodiments, the LBAs 32 may be converted into anionic surfactants. A description of an example techniques for converting alcohols into anionic surfactants, such as alcohol derived sulfates, is described in “Anionic Surfactants-Organic Chemistry”, Volume 56 of the Surfactant Science Series, Marcel Dekker, New York. 1996. It should be noted that such techniques may be applied to the disclosed LBAs 32. In some embodiments, the LBAs 32 may be converted into nonionic surfactants in accordance with disclosure US6963014.

[0062] In a further example, 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). It should be noted that alcohol derived ethoxylates may have similar structural features to the alcohol-derived sulfates except for their non-ionic hydrophilic group. As described herein, the surfactants 68 (e.g., alcohol -derived ethoxylates, alcohol ether sulfates, alcohol derived sulfates) may include advantageous properties,or combinations of properties, such as low BI values (e.g., minimal branching) and hard surface cleaning performance.

[0063] In some embodiments, 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. For example, 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. Advantageously, 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. Several non-limiting examples of the composition of the surfactant 68 are described below.

[0064] In an embodiment, the surfactants 68 may include repeating ethoxy (EO) units. For example, the surfactant (e.g., nonionic surfactant) produced using 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.

[0065] In some embodiments, 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. By way of example, referring to the method 60, at block 70, to form a detergent composition 74, one or more additives 72 may be provided to surfactants 68. As described herein, 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. Accordingly, the detergent compositions 74 include about 0.5% to about 90% by weight of surfactant 68. In general, the disclosed surfactants68 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.

[0066] In certain embodiments, the X of R-X (e.g., surfactant precursor 62) 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. For example, X may be a sulfate, ether sulfate, or ethoxylate.

[0067] In certain embodiments, when X (e.g., surfactant precursor 62) is an anionic head group, the resulting anionic surfactant may exist in an acid form. Further, 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. Non-limiting examples of 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. It should be noted that neutralization using an amine may be carried out to any sufficient degree of completion. For example, the degree of completion may be 100%, 80%, 70%, 60%, 50%, and so on. As one non-limiting example, 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.

[0068] In some instances, a portion of the carbon content of the surfactant 68 may be derived from renewable sources. For example, about 0.1% to about 100% of the carbon content of the first surfactant may be derived from renewable sources such as used cooking oil, vegetable oil, palm kernel oil, com / sugar cane ethanol etc. As used herein, 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 radiocarbonanalysis by accelerator mass spectrometry, liquid scintillation counting, and isotope mass spectrometry.

[0069] In some embodiments, 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.

[0070] In an embodiment, the surfactant 68 is an anionic surfactant (e.g., alcohol derived sulfates, such as alcohol ether sulfates). For example, 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).

[0071] In an embodiment, the surfactant 68 is a nonionic surfactant (e.g., alcohol derived ethoxylates). For example, 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).

[0072] In an embodiment, 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%. For example, 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%. For example, 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). In another example, the detergent composition 74 may include at least one surfactant 68 that is a nonionic surfactant (e.g., alcohol derived ethoxylates).

[0073] In an embodiment, 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%. For example, the total percentage of additives 72 (e.g., neutralizing agents, pH adjusters, stabilizers / chelating agents, solvents) 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%.

[0074] In an embodiment, the detergent compositions 74 may include solvents, such as water and / or organic solvents (e.g., alcohols, ethers, glycol ethers, combinations thereof). For example, the amount of solvent (e.g., water) may range from about 50% by to about 100% by weight. For example, 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%.

[0075] In an embodiment, 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.Example Preparation of Alcohol Sulfates

[0076] An example protocol for preparing alcohol sulfates using the LBAs 32 is described herein. The LBAs 32 are pre-cooled to less than 10°C in a round bottom flask with an ice-salt water bath. Chlorosulfonic acid is added dropwise to the alcohol with dry N2 purge while maintaining the temperature between 5°C to 15°C. The addition of chlorosulfonic acid was completed in about three hours. The salt water-ice bath was replaced with an ice water bath at 22- 24°C, and the N2 purge continued for another 30 mins. 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.Example Preparation of Alcohol Ethoxylates

[0077] An example protocol for preparing alcohol ethoxylates using the LB As 32 is described herein. Dried LBAs 32 and catalyst mix are introduced to a reactor, and the reactor is heated to the desired reaction temperature. The reactor was pressurized with N2 for inertness. Further, the process includes starting a mass-controlled ethylene oxide (EO) feed to the reactor. After feeding the desired mass of EO, the process includes maintaining the reaction temperature for a specified time (e.g., about 0.5 to about 2.5 hours (hrs), such as about 0.5 hr, about 1 hour, about 1.5 hr, or about 2 hr ) corresponding until most of the EO present in the reactor has reacted. Further still, the process includes depressurizing the reactor and start N2 purging to remove trace amounts of unreacted EO. Subsequently, the process includes neutralizing the catalyst and cooling to room temperature, and discharging the reactor.

[0078] Further embodiments of the present disclosure are directed to using the 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.Examples of Detergent Compositions

[0079] With the foregoing in mind, Tables 2-4 shows exemplary detergent compositions 74 that include surfactants 68 generated from the disclosed LBAs 32. For example, 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. In general, alcohols from Table 1 (e.g., Exp. Mat. 1, Comparative 1, Comparative 2, and Comparative 3) were utilized to generate surfactants (e.g., anionic surfactants, nonionic surfactant). For example, the disclosed LBA 32 (e.g., Exp. Mat. 1) was utilized to generate ananionic surfactant 68 (e.g., alcohol ether sulfate (AES) of Exp. Mat. 1) and nonionic surfactants 68 (e.g., alcohol ethoxylate EO7 of Exp. Mat. 1, alcohol ethoxylate EO9 of Exp. Mat. 1). In a generally similar manner, 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). It should be noted that the term “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. The properties of the detergent compositions 74 of Table 2 were evaluated in FIG. 4, which is discussed below.Table 2 shows exemplary detergent compositions 74 that include surfactants 68 generated from the disclosed LB As 32.

[0080] 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. For example, 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.

[0081] The test formula is based on the Industrieverband Kbperpflege und Waschmittel (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. For the test, 5 milliliters (mL) of a sample (e.g., Model A, Test 1, Test, 2, Test 3) from Table 2 is evenly distributed on a sponge with a defined weight, after which 10 strokes are applied within 30 seconds the tile. 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). In general, the y-axes of each of FIGS. 4-6 show the panel scores that were determined by the five panelists from the four replicates (4 readings per leg). The detailed description and procedure could be found in the publication SOFW Journal 141, German, 04- 2015, pages 47-56.

[0082] With the foregoing in mind, FIG. 4 is a graph showing cleaning performance values of various detergent compositions on hard surfaces of Table 2. To facilitate discussion, FIG. 4 and Table 2 will be discussed below concurrently. In general, each of the detergent compositions include a combination of an anionic surfactant and a nonionic surfactant. FIG. 4 demonstrates thatdetergent 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.

[0083] In the illustrated graph, 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. In contrast, Test 1 includes an anionic surfactant 68 (e.g., AES) generated from the LBA 32 and the same nonionic surfactant as Model A. Although Comparative 3 and AES of Exp. Mat. 1 are similar in length, 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).

[0084] 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).

[0085] In a generally similar manner, 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 ofEO 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.

[0086] By way of example, 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. In a generally similar manner as Table 2, 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) was utilized as the anionic surfactant across all four different samples. 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. For example, 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.

[0087] FIG. 5 is a graph showing cleaning performance values of various detergent compositions on hard surfaces of Table 3. To facilitate discussion, FIG. 5 and Table 3 will be discussed below concurrently. In general, 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. For example, 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.

[0088] The difference in performance can be attributed to the structural differences for a type of alcohol used to generate a particular surfactant. For example, 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. 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 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.

[0089] 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. Surprisingly, Test 4 outperforms Test 6, where Test 4 exhibits a ranking scoreof about 5.5, and Test 6 exhibits a ranking score of about 3.75. Without being bound by theory, it is believed that branched surfactants would be more effective at cleaning fat. For example, having relatively fewer branches at position two 50 and more branches at 4 and beyond (e.g., and position 5&5+ 56) may advantageously provide an improved cleaning performance. Put differently, 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). For example, having relatively fewer branches at position 2 and more branches at 4 and beyond (e.g., 5 and 5+) may provide the improved cleaning performance.

[0090] It should be noted that the difference in performance between 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. For example, Test 4’s nonionic surfactant 68 includes seven EO units, while Test 5’s nonionic surfactant includes nine EO units. Nevertheless, FIG. 5 demonstrates that lightly branched alcohols exhibit better cleaning performance than linear and highly branched alcohols.

[0091] By way of example, 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. In a generally similar manner as Table 2, alcohols from Table 1 (e.g., Exp. Mat. 1, Comparative 1, Comparative 2) were utilized to generate surfactants (e.g., anionic surfactants, nonionic surfactant). Furthermore, 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. 1) exhibit a pH ranging from about 7.8 to about 8.2. For example, the pH of the detergent compositions 74 was adjusted with 30% hydrochloric acid (HC1) or monoethanolamine to about 8. The five samples were subsequently evaluated for their cleaning performance on hard surfaces for removal of fat on tile, which is demonstrated in FIG. 5.Table 4 shows exemplary detergent compositions 74 that include surfactants 68 generated from the disclosed LB As 32.

[0092] FIG. 6 is a graph showing cleaning performance of various detergent compositions on hard surfaces of Table 4. To facilitate discussion, FIG. 6 and Table 4 will be discussed below concurrently. In general, 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. For example, detergent compositions 74 generated using the disclosed LBA 32 may exhibit a cleaning performance value that is greater than 6. For example, 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.

[0093] 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. For example, the nonionic surfactant in Model C2 (C12-C18 alcohol ethoxylate EO7) was generated using the Comparative 2 alcohol (natural linear). In the illustrated graph, 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. Without wishing to be bound by theory, these results indicate that lightbranching and branch distribution in alcohols may improve cleaning performance of surfactants 68 relative to alcohols that are lightly branched or linear. Relatedly, 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). As indicated above, without being bound by theory, it is believed that highly branched surfactants would be more effective at cleaning fat. In a generally similar manner as Table 3, LBA 32 has fewer branches at position two 50 relative to Comparative 1, while LBA 32 has more branches at position 5&5+ 56 relative to Comparative 1 (as demonstrated in Table 1). These results demonstrate that the disclosed lightly branched alcohols (branching index 1.53) that exhibit a first branch distribution as demonstrated in Table 1 may exhibit better cleaning performance than highly branched alcohols (branching index 2.08).

[0094] It should be noted that the difference in performance between Test 7 and Test 8 may be associated with the difference in the number of EO units in the nonionic surfactants for each respective test. For example, Test 7’s nonionic surfactant 68 includes seven EO units, while Test 8’s nonionic surfactant includes nine EO units. In a generally similar as FIG. 4, without being by theory, it is believed that 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. Accordingly, 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.

[0095] Accordingly, 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. In this way, 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. In general, the disclosed alcohol ethoxylate surfactant and alcohol ether sulfate surfactant may exhibit a good balance of cleaning properties for stain and grease removal. For example, 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). Accordingly, 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.

[0096] This written description uses embodiments / examples to disclose the invention, including the best mode, and also to enable any person skilled in the art to practice the invention, including making and using any devices or systems and performing any incorporated methods. The patentable scope of the invention is defined by the claims, and may include other embodiments / examples that occur to those skilled in the art. Such other embodiments / examples are intended to be within the scope of the claims if they have structural elements that do not differ from the literal language of the claims, or if they include equivalent structural elements with insubstantial differences from the literal language of the claims. Many alterations, modifications, and variations will be apparent to those skilled in the art in light of the foregoing description without departing from the spirit or scope of the present disclosure and that when numerical lower limits and numerical upper limits are listed herein, ranges from any lower limit to any upper limit are contemplated.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] Embodiment 5. The detergent composition of any preceding claim, wherein the one or more alcohol derived surfactants comprises alcohol ethoxylates.

[0102] Embodiment 6. The detergent composition of any preceding claim, wherein the one or more alkoxy groups are seven to nine ethoxy groups.

[0103] Embodiment 7. The detergent composition of any preceding claim, wherein the one or more alcohol derived surfactants comprises alcohol ether sulfates.

[0104] 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.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] Embodiment 12. The method of the preceding claim, wherein the surfactant is a nonionic surfactant or anionic surfactant.

[0109] Embodiment 13. The method of any preceding claim, further comprising providing one or more additives to the surfactant to generate a detergent composition.

[0110] 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.

[0111] Embodiment 15. The method of any preceding claim, wherein the surfactant has 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; and wherein R is an alkyl group; and

[0112] 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.

[0113] 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.

[0114] 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, whereingreater 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.

[0115] 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.

[0116] 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.

Claims

CLAIMS:

1. A detergent composition, comprising: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.

2. The detergent composition of claim 1, 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.

3. The detergent composition of claim 1, 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.

4. The detergent composition of claim 1, 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.

5. The detergent composition of claim 1, wherein the one or more alcohol derived surfactants comprises alcohol ethoxylates.

6. The detergent composition of claim 5, wherein the one or more alkoxy groups are seven to nine ethoxy groups.

7. The detergent composition of claim 1, wherein the one or more alcohol derived surfactants comprises alcohol ether sulfates.

8. The detergent composition of claim 1, wherein 100 wt. % of the detergent composition comprises about 0.01 wt. % to about 90 wt. % of the one or more additives.

9. The detergent composition of claim 1, 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.

10. The detergent composition of claim 1, 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.

11. A method, comprising: providing a butene feedstock; generating higher olefins by contacting the butene feedstock in the presence of a catalyst; fractionating the higher olefins to obtain lightly branched olefins; 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; providing a surfactant precursor; and generating a surfactant by contacting the alcohol composition with the surfactant precursor optionally in the presence of a catalyst.

12. The method of claim 11, wherein the surfactant is a nonionic surfactant or anionic surfactant.

13. The method of claim 11, further comprising providing one or more additives to the surfactant to generate a detergent composition.

14. The method of claim 11, wherein the surfactant has a branching index of ranging from about 1.3 to about 1.7.

15. The method of claim 11, wherein the surfactant has 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; and wherein R is an alkyl group.

16. The method of claim 11, 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.

17. The method of claim 13, wherein the one or more additives comprise one or more surfactants, solvents, pH adjusters, stabilizers, neutralizing agents, or a combination thereof.

18. A detergent composition, comprising: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.

19. The detergent composition of claim 18, 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.

20. The detergent composition of claim 19, 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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