WO2025199113A1

WO2025199113A1 - Methods and compositions for producing esters using lightly branched alcohols

Info

Publication number: WO2025199113A1
Application number: PCT/US2025/020386
Authority: WO
Inventors: Chunzhao Li; Travis A. Reine; Kyle G. LEWIS; Babak LOTFI; Guido ZICHITTELLA; Andrew D. SATTERFIELD
Original assignee: ExxonMobil Technology and Engineering Co
Current assignee: ExxonMobil Technology and Engineering Co
Priority date: 2024-03-19
Filing date: 2025-03-18
Publication date: 2025-09-25
Anticipated expiration: 2026-09-19
Also published as: WO2025199111A1

Abstract

Provided herein is a diester composition. The composition includes a plurality of esters each having one or more branched alkyl chains. The one or more branched alkyl chains are selected from the group consisting of: lightly branched C9 alkyl chains having a branching index between 1.1 and 1.9; lightly branched C 13 alkyl chains having a branching index between 1.1 and 2.3; or lightly branched C17 alkyl chains having a branching index between 1.9 and 2.6.

Description

METHODS AND COMPOSITIONS FOR PRODUCING ESTERS USING LIGHTLY BRANCHED ALCOHOLS

CROSS-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, U.S. Provisional Application No. 63/773,352 filed on March 17, 2025, and U.S. Provisional Application No. 63/773,360 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 that are esters with relatively high viscosity index, low pour point, and low volatility. In particular, the processes may include using a feed stream having branched oxo alcohols with precursors to generate the esters. The composition of matter and processes of this disclosure are especially useful for lubricant applications, such as automotive or industrial lubricant applications.

BACKGROUND

[0003] Lubricants in commercial use today are prepared from a variety of natural and synthetic base stocks admixed with various additive packages and solvents depending upon their intended application. The base stocks typically include mineral oils, polyalphaolefins (PAO), gas-to-liquid base oils (GTL)/Group III, silicone oils, phosphate esters, diesters, polyol esters, and the like. A major trend for passenger car engine oils (PCEOs) is an overall improvement in quality as higher quality base stocks become more readily available. Typically, the highest quality PCEO products are formulated with base stocks such as PAOs or GTL/Group III stocks.

[0004] PAOs and GTL/Group III stocks are an important class of lube base stocks with many excellent lubricating properties, including high viscosity index (VI), but may have lower thermal and oxidative stability. Thermal and oxidative stability is important because of a trend requiring smaller sump sizes that may result in more thermal and oxidative stress on the lubricants. Further, performance requirements for lubricants have become more stringent and the demand for longer drain intervals continues to grow.

[0005] Currently, PAOs are synthesized by a two-step reaction sequence from linear a-olefins (LAO), which are derived from ethylene. The first step is the synthesis of a mixture of oligomers, which are polymers of relatively low molecular weight. This first step is catalyzed using a boron trifluoride catalyst in conjunction with a protic catalyst such as water, alcohol, or a weak carboxylic acid. The second step in the manufacturing process entails hydrogenation of the unsaturated oligomer

[0006] The gas to liquids (GTL) process comprises three main process steps, firstly the reforming of natural gas to synthesis gas, a mixture of gases containing hydrogen, carbon monoxide, carbon dioxide and unreacted methane, secondly the Fischer Tropsch (FT) conversion of carbon monoxide and hydrogen to long chain hydrocarbons and thirdly the upgrading and refining of these hydrocarbons into liquid fuels and hydrocarbon based base oils. Group III base oils are produced by hydrocracking, hydroisomerization, and hydrotreating of a hydrocarbon feed to make the grade purer and high viscosity index. Due to the increasing demand for product performance, there is still a need for a relatively good performance lube base stock through alternative routes.

[0007] Group V base stocks, in particular, esters, are one way to achieve superior product performance. Esters are commonly used to increase solvency, add oxidative stability, lower traction and increase the efficiency of base oil mixtures and finished products. However, the molecular structure of esters may need further optimization to meet desired performance targets. SUMMARY

[0008] 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.

[0009] The present disclosure relates to techniques for producing or generating esters and using lightly branched oxo-alcohols (e.g., C9 oxo-alcohols, Cl l oxo-alcohols, C13 oxo-alcohols, C17 oxo-alcohols, and so on). It is presently recognized that esters formed from lightly branched oxoalcohols may provide lubricants that have suitable and/or improved viscosities, pour points, and other properties, as compared to certain conventional lubricants. In particular, the disclosed esters, and other chemical moi eties (e.g., phosphates) have one or more lightly branched alkyl chains derived from the lightly branched oxo-alcohols. The lightly branched alkyl chains may have a branching index between about 1.0 to 2.5. In some instances, the esters may be monoesters, neopentanoic esters, diesters, or triesters. In any case, the one or more lightly branched alkyl chains are linked (e.g., bonded) to an oxygen of the ester, while the carbonyl of the ester may be linked to a linear alkyl chain, an aromatic group, a phosphate, and other chemical moieties described herein. In any case, the disclosed compositions may provide lubricants having viscosities, pour points, and other properties that are useful for a variety of applications. [0010] 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

[0011] 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:

[0012] FIG. 1 is a flow diagram of a method for producing lightly branched oxo alcohols, in accordance with the present disclosure;

[0013] FIG. 2 is a flow diagram of a method for producing esters using the lightly branched oxo alcohols, in accordance with the present disclosure;

[0014] FIG. 3 is a flow diagram of a method for producing diesters using the lightly branched oxo alcohols, in accordance with the present disclosure;

[0015] FIG. 4 is a flow diagram of a method for producing neopentanoic esters using the lightly branched oxo alcohols, in accordance with the present disclosure;

[0016] FIG. 5 is a flow diagram of a method for producing monoesters using the lightly branched oxo alcohols, in accordance with the present disclosure;

[0017] FIG. 6 is a graph illustrating friction coefficient versus slide-roll ratio of the diester compositions made in accordance with the method of FIG. 3, in accordance with the present disclosure; and

[0018] FIG. 7 is a graph illustrating friction coefficient versus slide-roll ratio of the diester compositions made in accordance with the method of FIG. 3, in accordance with the present disclosure.

DETAILED DESCRIPTION

[0019] 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. [0020] 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%, ±25%, ±50%, or ±100%.

[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 C_nH(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 CnEEn, 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 terms "polymer" and “oligomer” are used interchangeably to refer to any two or more of the same or different repeating units/mer units or units. The term “homopolymer” refers to a polymer having units that are the same. The term “copolymer” refers to a polymer having two or more units that are different from each other, and includes terpolymers and the like. The term “hybrid oligomer” refers to a polymer having a linear alpha olefin and a linear branched olefin. Likewise, the definition of polymer, as used herein, includes homopolymers, copolymers, and the like.

[0025] The terms “branch,” “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.

[0026] 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

[0027] 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., ranging from about 1 to about 2.5, such as about 1 to about 1.9) in a given LBO sample.

[0028] The term “lightly branched alcohol (LBA)” refers to an alkyl chain with an alcohol (OH) group. While side chain branches are present in an LBA, the branching is minimal (e.g., one side branch, two side branches, or three side branches with an average branch of 1.5 branch per molecule) in a given LBA sample.

[0029] 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.

[0030] 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+).

[0031] 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 within ¹³C 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. [0032] The “freezing point measurement” of the disclosed esters was acquired using the SVM 3001 Cold Properties model. The SVM 3001 Cold Properties model is an upgraded version of the SVM 3001, equipped with an additional optical cell (CPFP module) for measuring cold flow properties. It can measure viscosity and density in the range of -60°C to +100°C. The CPFP cell, integrated into the sample drain, uses the same sample volume as the SVM 3001. This model is ideal for various fluids, such as diesel fuel, jet fuel, and hydraulic liquids, and can also determine the cloud point of substances such as liquid wax, coconut oil, olive oil, or shea butter. During cloud point and freezing point measurements, the viscosity cell motor is stopped, so viscosity and density are not measured. For filling, use a clean plastic syringe with a recommended volume of 5 mL, fill it bubble-free, plug it into the filling support, and push the plunger slowly to fill at least 1.5 mL of sample. It should be noted that a chiller with methanol solvent was used for samples with a freezing point below -20°C.

[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] 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

[0035] FIG. 1 illustrates a flow diagram of method 10 for producing lightly branched oxo alcohol composition (LB As) in accordance with certain embodiments of the present disclosure. It should be noted that the method 10 is not limiting, and the method 10 may include additional or fewer steps than those illustrated. Further, the method 10 may include steps that are performed in an alternative order to that illustrated. That is, certain steps may be performed before, after, or concurrently to/with another respective step.

[0036] As shown, 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 a lightly branched olefin (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, Cs olefin oligomers having an average branching index of about 1.8 or less, such as an average branching idex of about 1.0 to about 1.8, and Ci6-ci7 olefin oligomers having an average branching index of about 2.5 or less, such as an average branching idex of about 1.3 to about 2.5, 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, SAPO-11, preferably ZSM-23. 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 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. 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 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. Surprisingly, certain zeolite catalysts, particularly those having an MTT framework, such as ZSM-23 or modified ZSM-23, may promote formation of a distribution of Cs, C12, and Ci6 olefin oligomers while affording oligomers with a defined structure and a branching index for at least Cs olefins of about 1.8 or less, at least C12 olefins of about 2.2 or less particularly about 1.1 to about 1.7, and Ci6 olefins of about 2.5 or less.

[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 (i. e., tetramers of C4), C20, C24, etc.), lighter olefins 34 (e.g., olefins lighter than C12, such as C4 feed, C8 olefins (i.e., dimers of C4)) and lightly branched olefins (LBO) 26 (e.g., lightly branched C8 olefins, 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, lightly branched C16 olefins, and trace amounts of dienes and/or cyclic alkanes). In certain embodiments, the higher olefins 24 and/or lighter olefins 34 may be further fractionated. For example, the higher olefins 24 may be fractioned to obtain C16 olefins, while the lighter olefins 34 may be fractionated to obtain the C8 olefins. 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 (e.g., C8 olefins, C12 olefins, C16 olefins), may exhibit a branching index (e..g, C8 olefin branching index) ranging from about 1.0 to about 1.6, C12 branching index in the range of 1.0 to 1.9 (e.g., between 1.1 to 1.8, 1.2 to 1.7, 1.3 to 1.6), C16 branching index from about 1.5 to about 2.0, or a combination thereof.

[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). In some embodiments, the lighter olefins 34 (e.g., C8) or the higher olefins 24 (e.g., C16) may be contacted in the present of the catalyst 28 (e.g., instead of the LBO 26), thereby causing the lighter olefins 34 or the higher olefins 24 to undergo hydroformylation. As such, the LB As 32 may include alcohols that vary in carbon length (e.g., LBA C9 oxo alcohol, LBA C13 oxo alcohol, LBA C17 oxo alcohol) and may include one or more branches, two or more branches, three or more branches, along the main carbon chain. As described herein, the LBAs 32 may include advantageous properties, or combinations of properties, such as branching index, viscosity, and for use as a feedstock for producing esters.

[0046] The catalyst 28 may include a suitable transition metal complex (e.g., cobalt-based catalysts, ruthenium-based catalysts, iridium-based catalyst, preferably cobalt-based catalyst) 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 include advantageous properties, or combinations of properties, such as branching index, viscosity, for use as a feedstock for producing esters, 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)i₆, [Rh(norbornadiene)(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)I₂, [RuH(CO)(acetonitrile)₂(PPh₃)₃ ⁺ [BF4]', PtCl₂ (cyclooctadiene), [Ir(CO)₃ (PPh₃)]⁺ [PFe]', or [HPt(PEt₃)₃]⁺ [PFe]'. Other suitable catalysts may include, for example, HCo(CO)4, Co₂(CO)s, 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, RhCl₃»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 catalytic hydrogenation, 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 and methods for using the LB As 32 to generate esters (e.g., diesters, neopentanoic esters, monoesters).

Esters

[0053] With the foregoing in mind, FIG. 2 is a flow diagram of a method for producing esters using the lightly LB As 32. It should be noted that the method 40 is not limiting, and the method 40 may include additional steps than those illustrated or certain steps, illustrated as being performed concurrently, may be performed at different time periods.

[0054] Referring to the method 40, at block 44, precursors 42 are contacted with LBA 32 to produce an ester composition 46 (e.g., diester compositions, neopentanoic ester compositions, monoester compositions). As referred to herein, an “ester composition” refers to a reaction product that includes (e.g., comprises or consists essentially of) multiple esters. In particular, the ester composition 46 may be produced by LBAs 32 having different respective viscosity properties. The method 40, at block 44, may include providing a flow of a precursor feedstock (e.g., precursor feed flow rate) and a flow of a LBA feedstock (e.g., LBA feed flow rate). For example, the LBA feedstock may include a feed of an alcohol with a type of carbon length (e.g., C9 oxo alcohol feedstock, C13 oxo alcohol feedstock, C17 alcohol feedstock). In certain embodiments, the precursor feedstock and LB A feedstock may contact optionally in the presence of a catalyst and/or activator 38. For example, the feedstocks may be flowed over an optional solid support formed of the catalyst and/or activator 38 into a reactor. For example, the catalyst and/or activator 38 may be stored or otherwise contained in a reaction vessel, and the feedstock including precursor 42 and LBA 32 may be provided, flowed, or otherwise directed into the reaction vessel including the catalyst and/or activator 38. In some embodiments, the catalyst and/or activator 38 may be a catalyst platform that includes a catalyst and an activator. In some embodiments, the reactor may be a single fixed bed reactor or preferably a multi-tubular reactor.

[0055] In an embodiment, the precursors 42 may include one or more components to facilitate the formation of the ester composition 46. It should be noted that the preparation of the ester composition 46 (i.e., esterification reactions) can be accomplished using conventional methods and techniques familiar to one of ordinary skill in the art. For example, the precursors 42 may include carboxylic acids (e.g., alkyl acids, allylic acids, aromatic acids, dicarboxylic acids, tricarboxylic acids, phenolic acids), alcohols (e.g., alkyl alcohols, allylic alcohols, aromatic alcohols, polyols (e.g., diols, triols, tetrol)), etc. It should be known that these examples are not meant to be non-limiting. In some embodiments, the precursors 42 may include one or more fatty acids, having a carboxylic acid and an alkyl chain with four or more carbons.

[0056] Examples of suitable carboxylic acids may include alkyl acids (i.e., aliphatic acids, linear acids, branched acids), allylic acids, aromatic acids, carboxylic acids that have one or more carboxylic acid groups (COOH) (e.g., aliphatic, allylic, aromatic carboxylic acids), phenolic acids, or combinations thereof. The carboxylic acids may include from 2 to 30 carbon atoms and be straight (i.e., linear) aliphatic acids, branched chain aliphatic acids, and/or aromatic acids.

[0057] The linear carboxylic acids are any linear saturated alkyl carboxylic acid having a carbon number in the range between about C2 to C30 with one or more COOH groups. Some examples of linear acids include sebacic, azelaic, suberic, succinic, adipic, oxalic, malonic, glutaric, pivalic, lauric, palmitic, pimelic, alkyl acids wherein the alkyl group ranges from C2 (acetic acid)-C20 (icosanoic acid) (e.g., acetic, propionic, butyric acid, pentanoic acid, n-hexanoic, n-heptanoic, n-octanoic, n-nonanoic, n-decanoic acids, n-dodecanoic acids, n-tetradecanoic acids, n-hexadecanoic acids, n-octadecanoic acids, etc., and combinations thereof.

[0058] The branched acid may be a monocarboxylic acid which has a carbon number in the range between about C2 to about C30 with methyl, ethyl, or propyl branches. The monocarboxylic acid is preferably at least one acid selected from the group consisting of: 2,2- dimethylpropionic acid (neopentanoic acid), neoheptanoic acid, neooctanoic acid, neononanoic acid, isohexanoic acid, neodecanoic acid, 2-ethylhexanoic acid (2EH), 3,5,5-trimethylhexanoic acid (TMH), 2-ethyl-2-methylheptanoic acid, isoheptanoic acid, isooctanoic acid, isononanoic acid and isodecanoic acid. One especially preferred branched acid is 2,2-dimethylpropionic acid (neopentanoic acid). The term “neo” as used herein refers to a trialkyl acetic acid, i.e. an acid which is triply substituted at the alpha carbon with alkyl groups. These alkyl groups are equal to or greater than CH3, as demonstrated below:

[0059] wherein Ri, R2 and R3 are greater than or equal to CH3 and not equal to hydrogen.

[0060] The aromatic carboxylic acids are any aromatic carboxylic acid having a carbon number in the range between about C6 to C40 with one or more COOH groups, two or more COOH groups, or three or more COOH groups. In certain embodiments, the aromatic acids may include substituent groups such as alkyl groups, branched groups, or allylic groups that range from Cl to C20 carbons. In certain embodiments, the substituent groups may be modified to include nitrogen atoms, chlorine atoms, sulfur atoms, and/or COOH groups. Some examples of aromatic acids include, but are not limited to, phthalic acid, terephthalic acid, benzoic acid, salicylic acid, 3- phenylpropionic acid, 1,2,4-benzenetricarboxylic acid (1,2,4-benzenetricarboxylic acid, trimellitic acid), (3-methylbut-3-en-l-yl)benzene, and mixtures thereof. Additional precursors 42 may be reacted with the LBA 32, such as 4-nitrophenyl carb onochlori date, di(lH-imidazol-2- yl)m ethanone, inorganic compounds (e.g., phosphorous chlorides, such as phosphorus trichloride, phosphorus oxychloride, phosphorus pentachloride), etc.

[0061] Furthermore, additional components/examples of solvents, activators, catalysts, and the like to be utilized for the preparation of the ester composition 46 are described in US2018/0100710A1, US8987499B2, which are incorporated herein by reference. For example, any carboxyl activating agent/coupling agent may be used in any of the disclosed esterification reactions. Some exemplary activators/activating agent/coupling agent include l-ethyl-3-(3- dimethylaminopropyl)carbodiimide (EDC -HQ, EDC HC1), di cyclohexylcarbodiimide (DCC) pyridine, etc. Additionally, any catalyst suitable to perform esterification may be employed to generate the disclosed ester composition 46. Exemplary catalysts include 4- dimethylaminopyridine (DMAP), acid catalysts (e.g., sulfuric acid (H2SO4), hydrochloric acid (HC1), tosic acid (TsOH)), a catalyst including a compound or transition metal complex (e.g., zirconium-based catalysts, iridium-based catalysts, tin-based catalysts), etc. Accordingly, reaction between the LBA 32 and one or more of the precursors 42 and/or generates the ester composition 46 (e.g., diesters, neopentanoic esters, monoesters, organophosphates). In some embodiments, an acid chloride intermediate may be generated as part of obtaining the disclosed ester composition 46. It should be noted that any one or more of the foregoing precursors 46 may be used in any combinations to generate the ester composition 46 using the disclosed LBA 32. The ester composition 46 generated using the disclosed LBA 32 may include several advantages such as low Noack volatility, viscosity, pour point, etc., making them suitable as base stocks for lubricant formulations. Further details regarding the types of ester composition 46 that may be formed using the disclosed LBA 32 is discussed below with reference to FIGS. 3-5.

Diesters

[0062] By way of example, FIG. 3 illustrates a flow diagram of a method 50 for producing a diester composition 56, 46 (e.g., an ester composition 46) using the LBA 32 and diester precursor 52, 42, in accordance with certain embodiments of the present disclosure.

[0063] Referring to the method 50, at block 54, diester precursor 52,42 and the LBA 32 are contacted in the presence of a catalyst 58. As described herein, diester precursor 52, 42 (e.g., precursor 42) refers to any linear carboxylic acid that includes two COOH groups, (e.g., sebacic acid, azelaic acid, suberic acid, succinic acid, adipic acid, oxalic acid, malonic acid, glutaric acid, as described in FIG. 3). Contacting the diester precursor 52, 42 and LBAs 32 may include performing an esterification reaction to produce the diester composition 56,46. In some embodiments, contacting LBA 32 and the diester precursor 52, 42 optionally in the presence of a catalyst and/or activator 58 may include providing a flow of a feedstock (e.g., LBA feed flow rate and adipic acid derivatives feed flow rate) including the LBA 32 and diester precursor 52, 42 over a solid support formed of the catalyst and/or activator 58, which may be provided as discussed herein with respect to the catalyst 38. In some embodiments, the catalyst and/or activator 58 may be a catalyst platform that includes a catalyst including a compound or transition metal complex (e.g., zirconium-based catalysts, iridium-based catalysts, tin-based catalysts). In some embodiments, the catalyst and/or activator 58 may include any of the catalysts and/or activators as described in FIG. 2.

[0064] The disclosed diester composition 56,46 may include advantageous properties, or combinations of properties, such as viscosities (e.g., kinematic viscosity (KV), viscosity index, dynamic viscosity (DV)), Noack TGA weight loss, traction properties, pour points, specific gravity among other physical properties, that provide suitable applications as lubricants. Additionally, the resulting diester composition 56,46 can be advantageously utilized as a base stock for lubricant-based applications. Several non-limiting examples of the composition of the diester composition 56,46 are described below. However, it should be noted that the specific examples below are meant to be non-limiting. In general, the compositions described below describe the properties of the diester composition 56,46.

Neopentanoic Esters

[0065] By way of example, FIG. 4 illustrates a flow diagram of a method 60 for producing an ester composition 46 that is a neopentanoic ester composition 66, 46 using the LB A 32 and pivalic acid 52, 42 (e.g., precursor 42), in accordance with certain embodiments of the present disclosure.

[0066] Referring to the method 60, at block 64, pivalic acid 62,42 and the LBA 32 are contacted in the presence of an optional catalyst 58. As described herein, pivalic acid 62,42 refers to a carboxylic acid (e.g., as described in FIG. 3). For example, contacting pivalic acid 62, 42 and LBAs 32 may include performing an esterification reaction to produce the neopentanoic ester compositions 66, 46. In some embodiments, contacting LBA 32 and the pivalic acid 62,42 optionally in the presence of a catalyst and/or activator 68 may include providing a flow of a feedstock (e.g., LBA feed flow rate and pivalic acid feed flow rate) including the LBA 32 and the pivalic acid 62, 42 over a solid support formed of the catalyst 68, which may be provided as discussed herein with respect to the catalyst 38. For example, the catalyst and/or activator 68 may be stored or otherwise contained in a reaction vessel, and the feedstock including LBA 32 and pivalic acid 62,42 may be provided, flowed, or otherwise directed into the reaction vessel including the catalyst and/or activator 68 (e.g., acid-catalyzed reaction, such as sulfuric acid (H2SO4)). In some embodiments, the catalyst and/or activator 68 may be a catalyst platform that includes a catalyst and/or an activator. It should be noted that the catalyst and/or activator 68 may include any of the catalysts and/or activators as described in FIG. 3. In certain embodiments, an optional precursor 70, 42 may be provided, wherein the optional precursor 70,42 may include one or more carboxylic acids as described in FIG. 3. It should be noted that the preparation of the neopentanoic ester compositions 66,46 can be accomplished using conventional methods and techniques familiar to one of ordinary skill in the art.

[0067] The disclosed neopentanoic ester compositions 66, 46 may include advantageous properties, or combinations of properties, such as viscosities (e.g., KV, viscosity index), Noack TGA weight loss, traction properties, pour points, specific gravity among other physical properties, that provide suitable applications as lubricants. Additionally, the resulting neopentanoic ester compositions 66,46 can be advantageously utilized as a base stock for lubricant-based applications. Several non-limiting examples of the composition of the neopentanoic ester compositions 66,46 are described below. However, it should be noted that the specific examples below are meant to be non-limiting. In general, the compositions described below describe the properties of the neopentanoic ester compositions 66,46.

Monoesters

[0068] By way of example, FIG. 5 illustrates a flow diagram of a method 80 for producing an ester composition 46 that is a monoester composition 86, 46 using the LBA 32 and carboxylic acid 82,42 (e.g., precursor 42), in accordance with certain embodiments of the present disclosure.

[0069] Referring to the method 80, at block 84, carboxylic acid 82,42 and the LBA 32 are contacted in the presence of an optional catalyst and/or activator 88. As described herein, carboxylic acid refers to any carboxylic acid as described in FIG. 3. For example, contacting the carboxylic acid 82,42 and LB As 32 may include performing an esterification reaction to produce monoester compositions 86,46. In some embodiments, contacting LBA 32 and the carboxylic acid 82,42 optionally in the presence of a catalyst and/or activator 88 may include providing a flow of a feedstock (e.g., LBA feed flow rate and pivalic acid feed flow rate) including the LBA 32 and the carboxylic acid 82,42 over a solid support formed of the catalyst and/or activator 88, which may be provided as discussed herein with respect to the catalyst 38. In certain embodiments, an optional precursor 70, 42 may be provided. For example, the optional precursor 70, 42 may include any one of the precursors 42 as described in FIG. 3 (e.g., carboxylic acids, alcohols). The preparation of the monoester 86,46 can be accomplished using conventional methods and techniques familiar to one of ordinary skill in the art.

[0070] The disclosed monoester compositions 86,46 may include advantageous properties, or combinations of properties, such as viscosities (e.g., KV, viscosity index), Noack TGA weight loss, traction properties, pour points, specific gravity among other physical properties, that provide suitable applications as lubricants. Additionally, the resulting monoester composition 86,46 can be advantageously utilized as a base stock for lubricant-based applications. Several non-limiting examples of the composition of the monoester compositions 86,46 are described below. However, it should be noted that the specific examples below are meant to be non-limiting. In general, the compositions described below describe the properties of the monoester compositions 86,46.

Examples LBA 32 Examples

[0071] With the preceding in mind, Table 1 shows physical properties of the LBA 32 produced in accordance with the method 10 as disclosed in FIG. 1. In general, structural information regarding the LBAs 32 is obtained using C¹³ NMR. For example, Table 1 shows properties of LBA 32 corresponding to LBA C9 oxo alcohol and a comparative example (e.g., Comparative 1). Table 1 demonstrates that while the disclosed LBA 32 corresponding to the LBA C9 oxo alcohol exhibits a similar average carbon number than Comparative 1, the LBA C9 oxo alcohol exhibits less branching and is less viscous than Comparative 1. Accordingly, the disclosed properties of the LBA 32 (e.g., LBA C9 oxo alcohol) may be suitable for applications such as base stocks for lubricant formulations.

Table 1 shows properties of the disclosed branched C9 oxo alcohols (e.g., LBA 32) compared to comparative alcohols.

[0072] In an embodiment, the branching index of the disclosed LBA 32 (e.g., LBA C9 oxo alcohol) may range from about 1.0 to about 2.0, from about 1.1 to about 1.9, about 1.2 to about 1.8, about 1.3 to about 1.7, about 1.4 to about 1.6, such as about 1.1, about 1.2, about 1.3, about 1.4, about 1.5, about 1.6, about 1.7, about 1.8, about 1.9, or about 2.0. In an embodiment, the average carbon number of the disclosed LBA 32 (e.g., LBA C9 oxo alcohol) may range from about 8.5 to about 9.5, from about 8.7 to about 9.4, such as about 9.0, about 9.1, about 9.2, about 9.3, about 9.4, or about 9.5. In an embodiment, the KV at 20°C in mm²/s of the disclosed LBA 32 (e.g., LBA C9 oxo alcohol) may range from about 8 to about 18 mm²/s, such as about 8, about 9, 10, about 11, about 12, about 13, about 14, about 15, about 16, about 17, or about 18 mm²/s.

[0073] Table 2 shows properties of the disclosed LBA 32 (e.g., C13 oxo alcohol, C17 oxo alcohol) compared to comparative alcohols, in accordance with the embodiments of the present disclosure.

Table 2 shows properties of the disclosed branched C13 and C17 oxo alcohols (e.g., LBA 32) compared to comparative alcohols.

[0074] The LBAs 32 (e.g., C13 oxo alcohols) may exhibit an average number of carbons between about 12.0 and about 14.0, such as about 12.5 to about 13.5. For example, the average number of carbons may range between 12.7 and 13.3, 12.9 and 13.1, about 12.0, about 12.4, about 12.6, about 12.8, about 13.0, about 13.2, about 13.4, about 13.6, about 13.8, or about 14.0. Further, the LBAs 32 (e.g., C13 oxo alcohols) may exhibit a branching index between about 1.0 and about 2.5. For example, the branching index may range between about 1.1 to about 2.3, about 1.3 to about 2.3, such as 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, about 1.9, about 2.0, about 2.1, about 2.2, about 2.3, about 2.4, or about 2.5. The disclosed LBAs 32 (e.g., C13 oxo alcohols) may exhibit KV at 20°C between 30 to 40 mm²/s, or from about 32 to 38 mm²/s, or from about 34 to 36 mm²/s, such as about 30, about 32, about 34, about 36, about 38, or about 40 mm²/s.

[0075] Table 2 demonstrates that the disclosed LBA 32 (e.g., C13 oxo alcohols) exhibit a lower viscosity and lower pour point than Comparative 2. LBA 32 (e.g., C13 oxo alcohols) also exhibits a comparable BI and pour point as Comparative 5, but lower viscosity. These results demonstrate that the unique properties (e.g., viscosity, pour point) of the disclosed LBAs 32 may provide surprising advantages when utilized as an ester for base stock for lubricants.

[0076] With the preceding in mind, Table 3 shows physical properties of the LBA 32 produced in accordance with the method 10 as disclosed in FIG. 1. Table 3 shows properties of LBA 32 corresponding to LBA C17 oxo alcohol and comparative alcohols (e.g., Comparative 3 C17 alcohol). Table 3 demonstrates that the disclosed LBA 32 corresponding to the LBA C17 oxo alcohol exhibits a branching index and viscosity greater than the comparative. Additionally, the average carbon number of the LBA C17 oxo alcohol is greater than the comparative as well. Accordingly, the disclosed properties of the LBA 32 (e.g., LBA C17 oxo alcohol) may be suitable for applications such as base stocks for lubricant formulations.

Table 3 shows properties of the disclosed branched C17 oxo alcohols (e.g., LBA 32) compared to comparative alcohols.

[0077] In an embodiment, the branching index of the disclosed LBA 32 (e.g., LBA C17 oxo alcohol) may range from about 2.0 to about 3.0, from about 2.1 to about 2.9, about 2.2 to about 2.8, such as about 2.1, about 2.2, about 2.3, about 2.4, about 2.5, about 2.6, about 2.7, about 2.8, about 2.9, or about 3.0. In an embodiment, the average carbon number of the disclosed LBA 32 (e.g., LBA C17 oxo alcohol) may range from about 16.5 to about 17.5, from about 16.6 to about 17.4, such as about 16.5, about 16.6, about 16.7, about 16.8, about 16.9, about 17.0, about 17.1, about 17.2, about 17.3, about 17.4, or about 17.5. In an embodiment, the KV at 20°C in mm²/s of the disclosed LBA 32 (e.g., LBA C17 oxo alcohol) may range from about 60 to about 70 mm²/s, such as about 60, about 61, about 62, about 63, about 64, about 65, about 66, about 67, about 68, about 69, or about 70 mm²/s.

Examples

[0078] Provided below are examples of ester compositions 46 prepared in accordance with the present disclosures. In general, the examples show an ester prepared using an LBA 32. However, it should be appreciated that the ester compositions 46 may include other LB As 32, and thus, the ester compositions 46 may include alkyl chains derived from the LBAs 32 having branching properties, such as branching position and branching index, similar to those described with respect to the LBAs 32. For example, each ester composition 46 may include multiple esters, each including a lightly branched alkyl chains linked to an O of the ester. In some embodiments, the carbonyl of the ester may be linked to a carbonyl of an additional ester (e.g., via an aromatic group, a linear alkyl chain, and so on), which may include an additional light branched alkyl chain. In some embodiments, the carbonyl of the ester may be linked to an alkyl chain or aromatic group that is a terminating end group (e.g., not linked to an additional ester). In any case, it should be noted that the examples described below (e.g., with respect to the lightly branched alkyl chain) are meant to be non-limiting.

[0079] The example ester compositions 46 discussed below may be formed using the disclosed LB As 32 having one or more viscosity properties, as described herein. It should be noted that in some instances when a kinematic viscosity (KV) or dynamic viscosity (DV) is measured close to the freezing point of a respective ester composition 46, the KV may increase rapidly. In some instances, the KV may be relatively high (e.g., greater than 50 mm²/s, greater than 100 mm²/s, or greater than 150 mm²/s) and undesirable for use in certain applications. Nonetheless, certain esters may have desirable KVs above the freezing point. For example, it may be advantageous to utilize the disclosed esters that have a KV that is less than or equal to 50 mm²/s in automobiles. For simplicity, KV values in the Tables shown below may be expressed as “above threshold” when the KV exceeds a KV threshold (e.g., greater than or equal to 150 mm²/s).

Examples of Esters Generated using LB A 32 (e.g., C9 oxo alcohol)

[0080] The following are example ester compositions 46 generated using the LBA 32 (e.g., C9 oxo alcohol) as described by the methods of FIGS. 2 and 3. For simplicity, each reaction shows one example structure (i.e., representative structure) for a C9 oxo alcohol that may be used to generate the ester composition 46. However, it should be noted that the structure of the disclosed C9 oxo alcohol below is meant to be exemplary.

[0081] Target Al is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., phthalic acid (1), Chemical Formula: C9H20O; Molecular Weight: 144.26 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below: Target Al

[0082] Target Al, bis (4-methyloctyl)phthalate, is synthesized via a Steglich esterification reaction. Target 1 was synthesized by adding 4-methyloctan-l-ol (LBA C9) (15.28 g, 106 mmol), DMAP (5.88 g, 48.2 mmol) and followed by EDC-HC1 (27.7 g, 144 mol) to a stirred solution of phthalic acid (8 g, 48.2 mmol) in dichloromethane (DCM) (200 mL). The resulting mixture was stirred at room temperature (RT) for 16 hours (h/hr). The completion of reaction was monitored by thin-layer chromatography (TLC). After confirmation via TLC, the reaction mixture was diluted with ice cold water (1000 mL) and extracted into DCM (2 x 500 mL). The aqueous layer was re-extracted with DCM (2 x 500 mL). The combined organic layer was washed with brine (1000 mL), dried over sodium sulfate (Na2SO4), filtered, and concentrated under vacuum to afford 24 g of crude as yellow liquid. The crude product was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in petroleum ether (pet ether). Pure product fractions were collected and concentrated to get bis(4-methyloctyl) phthalate (16.4 g, 38.8 mmol, 81 % yield) as colorless liquid. Viscosity properties of Target Al are shown in Table 4. Characterization of Target AL Chemical Formula: C26H42O4. Molecular Weight: 418.62 g/mol. LCMS: m\z:419.4 (M+H), RT (min): 3.320, Area (%): 99.05. GCMS: m\z: 418.4 (M) +, RT (min): 8.839 to 10.16, Area (%): 94.30. HPLC: RT (min): 4.084, Area (%): 98.96. 1H-NMR (400 MHz, CDC13): 5 7.73 (d, J = 1.60 Hz, 2H), 7.54 (d, J = 3.60 Hz, 2H), 4.35-4.30 (m, 4H), 1.75-1.72 (m, 4H), 1.43-1.38 (m, 16H), 0.87-0.80 (m, 16H).

Table 4 shows viscosity properties of Target AL

[0083] Target A2 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., terephthalic acid (1), chemical formula: CsHeOe, Molecular Weight: 166.13 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below

Target A2

[0084] Target A2 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether. Pure product fractions were collected and concentrated to get bis(4-methyloctyl) terephthalate (17.4 g, 39.8 mmol, 83 % yield) as colorless liquid. Viscosity properties of Target A2 are shown in Table 5. Characterization of Target A2: Chemical Formula: C26H42O4, Molecular weight: 418.62 g/mol. LCMS: m\z:419.4 (M+H), RT (min): 3.614, Area (%): 97.90. GCMS: m\z: 418.4 (M) +, RT (min): 9.830 to 10.90, Area (%): 94.68. HPLC: RT (min): 4.408, Area (%): 95.78. 1H-NMR (400 MHz, CDC13): 5 8.11 (s, 4H), 4.38-4.34 (m, 4H), 1.79-1.74 (m, 3H), 1.44-1.37 (m, 16H), 0.89-0.85 (m, 15H).

Table 5 shows viscosity properties of Target A2.

[0085] Target A3 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., adipic acid (1), Chemical Formula: C6H20O4; Molecular Weight: 146.14 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

Target A3 [0086] Target A3 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), eluted with 2% ethyl acetate in petroleum ether to collect the pure fractions of compound, and concentrated to get bis(4-methyloctyl) adipate (22 g, 54.6 mmol, 80 % yield) as colorless liquid. Viscosity properties of Target A3 are shown in Table 6. Characterization of Target A3: Chemical Formula: C24H46O4; Molecular Weight: 398.63 g/mol. LCMS: m\z:399.3 (M+H), RT (min): 4.063, Area (%): 98.67. GCMS: m\z: 398.6 (M) +, RT (min): 8.218 to 9.040, Area (%): 98.01. HPLC: RT (min): 4.215, Area (%): 98.94. 1H-NMR (400 MHz, CDC13): 5 4.07-4.03 (m, 4H), 2.31 (s, 4H), 1.65-1.60 (m, 4H), 1.31-1.26 (m, 16H), 0.91-0.87 (m, 16H).

Table 6 shows viscosity properties of Target A3.

[0087] Target A4 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., glutaric acid (1), Chemical Formula: C5H8O4; Molecular Weight: 132.12 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below: DCM, RT,16 h

Target A4

[0088] Target A4 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), eluted with 2% ethyl acetate in pet ether to collect pure fractions of compound, and concentrated to get bis(4-methyloctyl) glutarate (17.2 g, 44.5 mmol, 73.5 % yield) as colorless liquid. Viscosity properties of Target A4 are shown in Table 7. Characterization of Target A4: Chemical Formula: C23H44O4. Molecular Weight: 384.60 g/mol. LCMS: m\z:385.3 (M+H), RT (min): 3.177, Area (%): 96.876. GCMS: m\z: 384.6 (M) +, RT (min): 8.178 to 8.849, Area (%): 99.77. HPLC: RT (min): 4.129, Area (%): 99.55. 1H-NMR (400 MHz, CDC13): 54.12-4.06 (m, 4H), 2.38 (t, J = 5.20 Hz, 4H), 1.96 (t, J = 7.20 Hz, 2H), 1.72-1.61 (m, 4H), 1.33-1.29 (m, 12H), 1.17-1.13 (m, 4H), 0.89-0.84 (m, 15H).

Table 7 shows viscosity properties of Target A4.

[0089] Target A5 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., succinic acid (1), Chemical Formula: C4H6O4; Molecular Weight: 118.09 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

DCM, Rt,16 h

Target A5

[0090] Target A5 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), eluted with 3% ethyl acetate in pet ether to collect pure fractions of compound, and concentrated to get bis(4-methyloctyl) succinate (23 g, 60.3 mmol, 89 % yield) as colorless liquid. Viscosity properties of Target A5 are shown in Table 8. Characterization of Target A5: Chemical Formula: C22H42O4. Molecular Weight: 370.57 g/mol. LCMS: m\z:371.3 (M+H), RT (min): 3.576, Area (%): 98.83. GCMS: m\z: 370.5 (M) +, RT (min): 7.881 to 8.373, Area (%): 94.33. HPLC: RT (min): 4.001, Area (%): 98.86. 1H-NMR (400 MHz, CDC13): 5 4.10-4.05 (m, 4H), 2.61 (s, 4H), 1.61-1.59 (m, 4H), 1.30-1.26 (m, 15H), 0.87-0.86 (m, 15H).

Table 8 shows viscosity properties of Target A5.

[0091] Target A6 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., benzoic acid (1), Chemical formula: C7H6O2; Molecular weight: 122.12 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

DCM, RT,16 h

Target A6

[0092] Target A6 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using

Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to obtain 4-methyloctyl benzoate (15.4 g, 61.2 mmol, 93 % yield) as pale yellow liquid. Viscosity properties of Target A6 are shown in Table 9. Characterization of Target A6: Chemical Formula: C16H24O2; Molecular weight: 248.37 g/mol. LCMS: Not detected. GCMS: m\z: 248.3 (M) +, RT (min): 6.878 to 7.116, Area (%): 97.61. HPLC: RT (min): 2.887, Area (%): 98.68. 1H-NMR (400 MHz, CDC13): 5 8.07 (d, J = 2.00 Hz, 2H), 7.57 (t, J = 1.20 Hz, 1H), 7.46 (t, J = 7.60 Hz, 2H), 4.39-4.33 (m, 2H), 1.81-1.72 (m, 2H), 1.47-1.39 (m, 9H), 0.93-0.89 (m, 8H). | KV-0,001 | 19,011 | 18,4443 | 0,97019

Table 9 shows viscosity properties of Target A6.

[0093] Target A7 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 2-hydroxybenzoic acid (1) (salicylic acid), Chemical Formula: C7H2O3; Molecular weight: 138.12 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below: Toulene, 145 C, 16h

Target A7

[0094] Target A7 was synthesized via an acid-catalyzed Fisher esterification reaction 6 following generally similar synthesis conditions as Target A12 below with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude product was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 4-m ethyloctyl 2-hydroxybenzoate (24 g, 90 mmol, 61.9 % yield) as yellow liquid. The product (24 g) was repurified by distillation and Product was distilled at 145°C (oil bath temperature) under 0.001 mbar vacuum to give 21 g of product as a colorless liquid. Viscosity properties of Target A7 are shown in Table 10. Characterization of Target A7: Chemical formula: C16H24O3. Molecular weight: 264.37 g/mol. LCMS: Not Detected. GCMS: m\z: 342 (M) ⁺, RT (min): 6.957 to 7.295, Area (%): 98.91. HPLC: RT (min):6.882, Area (%): 99.60 'H-NMR (400 MHz, CDC13): 5 0.89 (s, 1H), 7.87 (t, J= 4.40 Hz, 1H), 7.46 (t, J= 1.60 Hz, 1H), 7.00 (d, J = 8.40 Hz, 1H), 6.90 (t, J = 7.60 Hz, 1H), 4.41-4.35 (m, 2H), 1.82-1.78 (m, 2H), 1.43-1.37 (m, 10H), 1.00-0.91 (m, 9H).

Table 10 shows viscosity properties of Target A7. [0095] Target A8 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 3 -phenylpropanoic acid (1); Chemical Formula: C9H10O2; Molecular Weight: 150.18 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below: , ,

Target A8

[0096] Target A8 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 4-methyloctyl 3-phenylpropanoate (17.4 g, 62.9 mmol, 94 % yield) as colorless liquid. Viscosity properties of Target A8 are shown in Table 11. Characterization of Target A8: Chemical Formula: C18H28O2; Molecular Weight: 276.42 g/mol. LCMS: m\z:277.2 (M+H), RT (min): 2.231, Area (%): 99.97. GCMS: m\z: 276.4 (M)⁺, RT (min): 6.878 to 7.116, Area (%): 97.61. HPLC: RT (min): 6.797, Area (%): 99.93 'H-NMR (400 MHz, CDC13): 57.31 (t, J= 3.20 Hz, 2H), 7.23 (d, J= 6.80 Hz, 3H), 4.14-4.10 (m, 2H), 2.99 (t, J= 8.00 Hz, 2H), 2.66 (t, J= 2.40 Hz, 2H), 1.69-1.63 (m, 2H), 1.35-1.31 (m, 8H), 0.95-0.90 (m, 8H).

Table 11 shows viscosity properties of Target A8.

[0097] Target A9 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 4-nitrophenyl carb onochlori date (1), chemical formula: C7H4CINO4, molecular weight: 201.56 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

Target A9

[0098] Target A9 was synthesized by the following: To a stirred solution of 4-methyloctan-l-ol (39.0 g, 270 mmol) in DCM (250 mL), DMAP (15 g, 123 mmol) and 4-nitrophenyl carb onochlori date (24.75 g, 123 mmol) were added, and then the resulting mixture was stirred at room temperature for 16 h. The completion of the reaction was monitored by TLC. After completion of reaction, reaction was diluted with ice cold water (1000 mL), Compound was extracted into DCM (2 x 500 mL) The aqueous layer was re-extracted with DCM (2 x 500 mL). The combined organic layer was washed with brine (1000 mL), dried over Na2SO4, filtered and concentrated under vacuum to afford 36 g of crude as yellow liquid. The crude product was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) ini 2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get bis(4- methyloctyl) carbonate (20 g, 63.2 mmol, 55.2 % yield) as colorless liquid. Viscosity properties of Target A9 are shown in Table 12. Characterization of Target A9: Chemical Formula: C19H38O3; Molecular weight: 314.51 g/mol. LCMS: m\z:315.2 (M+H), RT (min): 3.624, Area (%): 99.33. GCMS: m\z:315.2 (M)⁺, RT (min): 6.980 to 7.492, Area (%): 97.91.HPLC: RT (min): 4.077, Area (%): 99.33. 'H-NMR (400 MHz, CDC13): 5 4.17-4.11 (m, 4H), 1.68-1.64 (m, 4H), 1.36-1.31 (m, 15H), 1.16-1.13 (m, 4H), 0.88-0.83 (m, 18H).

Table 12 shows viscosity properties of Target A9.

[0099] Target A10 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., oxalic acid(l), chemical formular: C2H2O4, molecular weight: 90.03 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

Target A10

[00100] Target A10 was synthesized via an acid-catalyzed Fisher esterification reaction 6 following generally similar synthesis conditions as Target A12 below with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude product was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 4 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get bis(4-methyloctyl) oxalate (33 g, 96 mmol, 87 % yield) as red liquid. The product (33 g) was repurified by distillation and product was distilled at 145 °C (oil bath temperature) under 0.001 mbar vacuum to give 20 g as a colorless liquid. Viscosity properties of Target A10 are shown in Table 13. Characterization of Target A10: Chemical Formula: C20H38O4; Molecular Weight: 342.52 g/mol. LCMS: 342 (M+H), RT (min):3.438, Area (%): 99.19.GCMS: m\z: 342 (M)⁺, RT (min): 7.342 to 7.860, Area (%): 99.07. HPLC: RT (min):3.874, Area (%): 99.36. 'H-NMR (400 MHz, CDC13): 54.32-4.26 (m, 4H), 1.73-1.70 (m, 4H), 1.38-1.34 (m, 19H), 0.86-0.81 (m, 18H).

Table 13 shows viscosity properties of Target A10.

[00101] Target All is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., phosphoryl trichloride (1), chemical formula: CI3OP, molecular weight: 153.32 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

Target Al l

[00102] Target Al 1 was synthesized by the following: To a stirred solution of 4-methyloctan- l-ol (32.9 g, 228 mmol) in DCM (200 mL), triethylamine (40.9 mL, 293 mmol) and phosphoryl trichloride (10 g, 65.2 mmol) were added, and then the resulting mixture was stirred at room temperature for 48 h. Completion of reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with ice cold water (1000 mL), Compound was extracted into DCM (2 x 500 mL). The aqueous layer was re-extracted with DCM (2 x 500 mL). The combined organic layer was washed with brine (1000 mL), dried over Na2SO4, filtered, and concentrated under vacuum to afford 33 g of crude as colorless liquid. The crude product (33 g) was purified by distillation and the alcohol was distilled at 70°C (oil bath temperature) under 0.001 mbar vacuum to give 28 g as a colorless liquid (residue). The residue was purified by column chromatography using Biotage isolera snap-340 g (230-400 silica gel) in 8 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get tris(4-methyloctyl) phosphate (20 g, 41.6 mmol, 70.9 % yield) as colorless liquid. Viscosity properties of Target Al 1 are shown in Table 14. Characterization of Target Al l : Chemical Formula: C27H57O4P; Molecular Weight: 467.72 g/mol. LCMS: m\z:477.4 (M+H), RT (min): 4.161, Area (%): 99.79. GCMS: m\z: 477.4 (M) ⁺, RT (min): 9.414 to 10.048, Area (%): 95.64. HPLC: RT (min): 4.800, Area (%): 99.26. 'H- NMR (400 MHz, CDC13): 54.00-3.99 (m, 6H), 1.65-1.61 (m, 6H), 1.34-1.27 (m, 22H), 0.88-0.84 (m, 22H).

Table 14 shows viscosity properties of Target Al l.

[00103] Target A12 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 2-ethyl-2-methylheptanoic acid (1), chemical formula: C10H20O2, molecular weight: 172.27 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below: Toulene, 140 °C, 16 h

Target Al 2

[00104] Target A12 is synthesized via an acid-catalyzed Fisher esterification reaction. In particular, Target A12 was synthesized via the following: To a stirred solution of 4-methyloctan- l-ol (20.10 g, 139 mmol) in toluene (300 mL), H2SO4 (Catalytic amount) (1.238 mL, 23.22 mmol) and 2-ethyl-2-methylheptanoic acid (20 g, 116 mmol) were added, and the resulting mixture was stirred at 140 °C for 16 h. Completion of reaction was monitored by TLC. After completion of reaction, the mixture was diluted with 10% aqueous (aq) NaHCCL ice cold solution (1000 mL). The compound was extracted into ethyl acetate (2 x 500 mL). The aqueous layer was re-extracted with ethyl acetate (2 x 500 mL). The combined organic layer was washed with brine (1000 mL), dried over Na2SO4, filtered, and concentrated under vacuum to afford 33 g of crude as yellow liquid. The residue was purified by manual column chromatography using (230-400 silica gel) in 2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 4- methyloctyl 2-ethyl-2-methylheptanoate (15.7 g, 51.7 mmol, 44.5 % yield) as a colorless liquid. Viscosity properties of Target A12 are shown in Table 15. Characterization of Target A12: Chemical formula: C19H38O2; Molecular Weight: 298.51 g/mol. LCMS: Not Detected. GCMS: m\z: 298.5 (M) ⁺, RT (min): 6.513 to 6.972, Area (%): 94.14. HPLC: RT (min): 4.238, Area (%): 98.33. 'H-NMR (400 MHz, CDC13): 54.05-4.03 (m, 2H), 1.65-1.58 (m, 4H), 1.50-1.40 (m, 16H), 1.09 (s, 1H), 0.89-0.84 (m, 16H).

Table 15 shows viscosity properties of Target A12. [00105] Target A13 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., pivalic acid (1), chemical formula: C5H10O2; molecular weight: 102.13 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

EDC.HC1 (1.5 eq), DMAP (0.5 eq)

1 DCM, RT, 16h

Target Al 3

[00106] Target A13 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) ian 2% ethyl acetate in pet ether to collect the pure fractions of compound and concentrated to get 4-methyloctyl pivalate (19 g, 81 mmol, 92 % yield) as a colorless liquid. Viscosity properties of Target A13 are shown in Table 16. Characterization of Target A13 includes: Chemical Formula: C14H28O2; Molecular Weight: 228.38 g/mol. LCMS: Not Detected. GCMS: m\z: 228.3 (M) ⁺, RT (min): 4.869 to 5.459, Area (%): 95.07. HPLC: RT (min): 3.145, Area (%): 97.01. 'H-NMR (400 MHz, CDC13): 5 4.08-4.04 (m, 2H), 1.64-1.62 (m, 2H), 1.60-1.57 (m, 6H), 1.20-1.19 (m, 11H), 0.88-0.87 (m, 8H).

Table 16 shows viscosity properties of Target A13.

[00107] Target A14 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., benzene- 1, 2, 4-tricarboxylic acid (1); chemical formula: CgHeOe; molecular weight: 210.14 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

Target Al 4

[00108] Target A14 was synthesized via an acid-catalyzed Fisher esterification reaction 6 following generally similar synthesis conditions as Target A12 above with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Multiple column purification was performed for Target A14. The residue was purified by manual column chromatography using (230-400 silica gel) in 2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get tris(4-methyloctyl) benzene- 1,2, 4- tri carb oxy late (20 g, 33.6 mmol, 79 % yield) as a yellow liquid. Viscosity properties for Target A14 are shown in Table 17. Characterization of Target A14: Chemical Formula: CseHsoOe;

Molecular Weight: 588.87 g/mol. LCMS: 589.4 (M+H), RT (min):4.400, Area (%): 97.15. GCMS: m\z: 589.4 (M) ⁺, RT (min): 6.957 to 7.295, Area (%): HPLC: RT (min):4.997, Area (%): 99.03. 'H-NMR (400 MHz, CDC1₃): 8 8.40 (s, 1H), 8.20 (d, J = 7.60 Hz, 1H), 7.76 (d, J= 8.00 Hz, 1H), 4.38-4.32 (m, 6H), 1.76-1.70 (m, 6H), 1.37-1.32 (m, 25H), 0.89-0.85 (m, 22H). Table 17 shows viscosity properties of Target A14.

[00109] Target A15 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., octanoic acid (1), chemical formula: CsHieCh, molecular weight: 144.21 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

EDC.HC1 (1.5 eq), DMAP (0.5 eq) DCM, RT, 16h

Target Al 5

[00110] Target A15 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 4-methyloctyl octanoate (18 g, 65.8 mmol, 95 % yield) as a colorless liquid. Viscosity properties of Target Al 5 are shown in Table 18. Characterization of Target Al 5 includes: Chemical Formula: C17H34O2; Molecular Weight: 270.46 g/mol. LCMS: m\z:271.3 (M+H), RT (min): 3.438, Area (%): 99.31. GCMS: m\z: 270.4

(M) ⁺, RT (min): 6.548 to 6.890, Area (%): 96.87. HPLC: RT (min): 3.849, Area (%): 98.58. ¹H- NMR (400 MHz, CDC13): 5 4.07-4.05 (m, 2H), 2.29-2.27 (m, 2H), 1.64-1.61 (m, 4H), 1.32-1.27 (m, 15H), 0.89-0.84 (m, 10H).

Table 18 shows viscosity properties of Target A15. [00111] Target A16 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., decanoic acid (1), chemical formula: C10H20O2; molecular weight 172.27 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below: Target Al 6

[00112] Target A16 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 4-methyloctyl decanoate (19.8 g, 65.5 mmol, 94 % yield) as a colorless liquid. Viscosity properties of Target A16 are shown in Table 19. Characterization of Target A16 includes: Chemical Formula: C19H38O2; Molecular Weight: 298.51 g/mol. LCMS: m\z:299.4 (M+H), RT (min): 3.787, Area (%): 99.83. GCMS: m\z: 298.5 (M) ⁺, RT (min): 7.012 to 7.385, Area (%): 97.06. HPLC: RT (min): 4.259, Area (%): 98.77. ¹H- NMR (400 MHz, CDC13): : 54.13-4.08 (m, 2H), 2.32-2.27 (m, 2H), 1.72-1.61 (m, 4H), 1.34-1.17 (m, 18H), 1.27-1.15 (m, 2H), 0.90-0.85 (m, 10H).

Table 19 shows viscosity properties of Target A16.

[00113] Target A17 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., dodecanoic acid (1), chemical formula: C12H24O2, molecular weight: 200.32 g/mol) was reacted with the disclosed C9 oxo alcohol (2). The example reaction scheme is shown below:

Target Al 7

[00114] Target A17 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 4-methyloctyl dodecanoate (22 g, 67.3 mmol, 90 % yield) as a colorless liquid. Viscosity properties for Target A17 are shown in Table 20. Characterization of Target A17 includes: Chemical Formula: C21H42O2; Molecular Weight: 326.57 g/mol. LCMS: Not Detected. GCMS: m\z: 326.5 (M) ⁺, RT (min): 7.500 to 7.850, Area (%): 97.33. HPLC: RT (min): 4.558, Area (%): 99.93. 'H-NMR (400 MHz, CDCI3): 8 4.11-4.05 (m, 2H), 2.31-2.27 (m, 2H), 1.75-1.59 (m, 4H), 1.17-0.91 (m, 24H), 0.87-0.85 (m, 10H).

Table 20 shows viscosity properties of Target A17.

[00115] Target A18 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., stearic acid (1), chemical formula C18H36O2, molecular weight 284.48 g/mol) was reacted with the disclosed C9 oxo alcohol (2).The example reaction scheme is shown below:

Target Al 8

[00116] Target A18 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 4-methyloctyl stearate (20 g, 48.5 mmol, 92 % yield) as colorless liquid colorless liquid. Viscosity properties for Target Al 8 are shown in Table 21. Characterization of Target A18 includes: Chemical Formula; C27H54O2; Molecular Weight: 410.73 g/mol. LCMS: m\z:411.4 (M+H), RT (min): 4.735, Area (%): 99.11. GCMS: m\z: 326.5 (M)⁺, RT (min): 9.216 to 9.914, Area (%): 92.96. HPLC: RT (min): 5.256, Area (%): 99.62. 'H-NMR (400 MHz, CDCI3): 6 4.07-4.04 (m, 2H), 2.32-2.27 (m, 2H), 1.65-1.37 (m, 4H), 1.35- 1.27 (m, 35H), 0.91-0.87 (m, 10H).

Table 21 shows viscosity properties of Target A18.

[00117] In an embodiment, the ester composition 46 generated using the disclosed LBA 32 (e.g., C9 oxo alcohol) may exhibit a KV at about 40°C ranging from about 1 mm²/s to about 80 mm²/s, about 10 to about 70 mm²/s, about 20 to about 50 mm²/s, about 30 to about 40 mm²/s, about 1 to about 5 mm²/s, about 1 to about 10 mm²/s, about 1 to about 20 mm²/s, about 1 to about 30 mm²/s, such as about 1, about 5, about 10, about 20, about 30, about 40, about 50, about 60, about 70 or about 80 mm²/s. The ester composition 46 may exhibit a DV at about 40°C ranging from about 1 millipascal second (mPa-s) to about 80 mPa-s, about 10 to 70 mPa-s, about 20 to 50 mPa-s, about 30 to 40 mPa-s, about 1 to 5 mPa-s, about 1 to 10 mPa-s, about 1 to 20 mPa-s, about 1 to 30 mPa-s, such as about 1, about 5, about 10, about 20, about 30, about 40, about 50, about 60, about 70 or about 80 mPa-s. The ester composition 46 may exhibit a density at about 40°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00118] In an embodiment, the ester composition 46 generated using the disclosed LBA 32 (e.g., C9 oxo alcohol) may exhibit a KV at about 100°C ranging from about 0.1 mm²/s to about 15 mm²/s, about 1 to about 12 mm²/s, about 2 to 11 about mm²/s, about 3 to about 10 mm²/s, about 4 to about 9 mm²/s, about 5 to 8 mm²/s, about 1 to 5 mm²/s, about 1 to 3 mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mm²/s. The ester composition 46 may exhibit a DV at about 100°C ranging from about 0.1 mPa-s to about 15 mPa-s, about 1 to 12 mPa-s, about 2 to 11 mPa-s, about 3 to 10 mPa-s, about 4 to 9 mPa-s, about 5 to 8 mPa-s, about 1 to 3 mPa-s, about 5 to 8 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mPa-s. The ester composition 46 may exhibit a density at about 100°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00119] In an embodiment, the ester composition 46 generated using the disclosed LBA 32 (e.g., C9 oxo alcohol) may exhibit a KV at about -35°C ranging from about 0 mm²/s to about 600 mm²/s, about 0 to about 500 mm²/s, about 0 to about 100 mm²/s, about 0 to about 50 mm²/s, such as about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70 about 80, about 90, about 100, about 200, about 300, about 400, about 500, about 600 mm²/s. The ester composition 46 may exhibit a DV at about -35°C ranging from about 0 mPa-s to about 600 mPa-s, about 0 to about 500 mPa-s, about 0 to about 100 mPa-s, about 0 to about 50 mPa-s, such as about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70 about 80, about 90, about 100, about 200, about 300, about 400, about 500, about 600 mPa-s. The ester composition 46 may exhibit a density at about -35°C ranging from about 0 g/cm³ to about 1.20 g/cm³, about 0.70 to about 1.1, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about such as about 0, about 0.02, about 0.12, about 0.22, about 0.32, about 0.42, about 0.52, about 0.62, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, about 1, about 1.02, about 1.04, about 1.06, about 1.08, about 1.10, about 1.12, about 1.14, about 1.16, about 1.18, or about 1.20 g/cm³.

[00120] In an embodiment, the ester composition 46 generated using the disclosed LBA 32 (e.g., C9 oxo alcohol) may exhibit a KV at about -20°C ranging from about 0 mm²/s to about 250 mm²/s, about 0 to about 100 mm²/s, about 0 to about 50 mm²/s, such as about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70 about 80, about 90, about 100, about 125, about 150, about 175, about 200, about 225, or about 250 mm²/s. The ester composition 46 may exhibit a DV at about -20°C ranging from about 0 mPa-s to about 250 mPa-s, about 0 to about 100 mPa-s, about 0 to about 50 mPa-s, such as about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70 about 80, about 90, about 100, about 125, about 150, about 175, about 200, about 225, or about 250 mPa-s. The ester composition 46 may exhibit a density at about -20°C ranging from about 0.0 g/cm³ to about 11.00 g/cm³, such as about 0.70 to about 1.5, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about such as about 0, about 0.02, about 0.12, about 0.22, about 0.32, about 0.42, about 0.52, about 0.62, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, about 1, about 1.02, about 1.04, about 1.06, about 1.08, about 1.10, about 1.12, about 1.14, about 1.16, about 1.18, about 1.20, about 1.40, about 1.60, about 1.80, about 2.00, about 3.00, about 4.00, about 5.00, about 6.00, about 7.00, about 8.00, about 9.00, about 10.00, or about 11.00 g/cm³.

[00121] In an embodiment, the ester composition 46 generated using the disclosed LBA 32 (e.g., C9 oxo alcohol) may exhibit a KV at about -10°C ranging from about 0 mm²/s to about 125 mm²/s, about 0 to about 100 mm²/s, about 0 to about 50 mm²/s, about 40 to about 90 mm²/s, such as about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, or about 125 mm²/s. The ester composition 46 may exhibit a DV at about -10°C ranging from about 0 mPa-s to about 125 mPa-s, about 0 to about 100 mPa-s, about 0 to about 50 mPa-s, about 40 to about 90 mPa-s, such as about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, or about 125 mPa-s. The ester composition 46 may exhibit a density at about -10°C ranging from about 0 g/cm³ to about 1.20 g/cm³, about 0.70 to about 1.1, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about such as about 0, about 0.02, about 0.12, about 0.22, about 0.32, about 0.42, about 0.52, about 0.62, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, about 1, about 1.02, about 1.04, about 1.06, about 1.08, about 1.10, about 1.12, about 1.14, about 1.16, about 1.18, or about 1.20 g/cm³.

[00122] In an embodiment, the ester composition 46 generated using the disclosed LBA 32 (e.g., C9 oxo alcohol) may exhibit a KV at about 0°C ranging from about 0 mm²/s to about 360 mm²/s, about 0 to about 100 mm²/s, about 0 to about 50 mm²/s, about 0 to about 35 mm²/s, about 0 to about 25 mm²/s, such as about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 200, about 300, or about 360 mm²/s. The ester composition 46 may exhibit a DV at about 0°C ranging from about 0 mPa-s to about 360 mPa-s, about 0 to about 100 mPa-s, about 0 to about 50 mPa-s, about 0 to about 35 mPa-s, about 0 to about 25 mPa-s, such as about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 200, about 300, or about 360 mPa-s. The ester composition 46 may exhibit a density at about 0°C ranging from about 0 g/cm³ to about 1.20 g/cm³, about 0.70 to about 1.1, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about such as about 0, about 0.02, about 0.12, about 0.22, about 0.32, about 0.42, about 0.52, about 0.62, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, about 1, about 1.02, about 1.04, about 1.06, about 1.08, about 1.10, about 1.12, about 1.14, about 1.16, about 1.18, or about 1.20 g/cm³. [00123] In an embodiment, the ester composition 46 generated using the disclosed LBA 32 (e.g., C9 oxo alcohol) may exhibit a freezing point ranging from about -60°C to about -20°C, from about -55 to about -25, about -50 to about -30, about -45 to about -35, about -60, about -55, about -50, about -45, about -40, about -35, about -30, about -25, or about -20°C.

Examples of Esters Generated using LBA 32 (e.g., C13 oxo alcohol)

[00124] The following are example ester composition 46 generated using the LBA 32 (e.g., C13 oxo alcohol) as described by the methods of FIGS. 2 and 3. For simplicity, each reaction shows one example structure (i.e., representative structure) for a C13 oxo alcohol that may be used to generate the ester composition 46. However, it should be noted that the structure of the disclosed C13 oxo alcohol below is meant to be exemplary. It should be noted that in some instances when a KV is measured close to the freezing point of a respective ester composition 46, the KV may increase rapidly and be a value that is undesirable for use in certain applications. Nonetheless, certain esters may have desirable KVs above the freezing point.

[00125] Target Bl is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., phthalic acid (1), chemical formula: CsHeCU; molecular weight: 166.13 g/mol) was reacted with the disclosed C13 oxo alcohol (2) (chemical formula: C13H28O; molecular weight: 200.37 g/mol). The example reaction scheme is shown below:

Target Bl

[00126] Target Bl was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents to another. Characterization of Bl includes: Chemical Formula: C34H58O4; Molecular Weight: 530.83 g/mol. LCMS: Mass not observed, RT (min): 0.496, Area (%): 96.89. GCMS: Mass not observed, RT (min): 9.755, Area (%): 99.91. HPLC: RT (min): 5.121, Area (%): 95.53. 'H-NMR (400 MHz, CDC13): 5 7.73-7.72 (m, 2H), 7.55-7.53 (m, 2H), 4.36-4.30 (m, 2H), 4.24-4.23 m, 2H), 1.77-1.73 (m, 2H), 1.11-1.72 (m, 28H), 0.82-1.10 (m, 20H).

[00127] Target B2 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., terephthalic acid (1), chemical formula: CsHeOe, Molecular Weight: 166.13 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

DCM (15 vol), 16 h, RT

Target B2

[00128] Target B2 was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target B2: Chemical Formula: C34H58O4, Molecular weight: 530.83 g/mol. GCMS: Mass not observed, RT (min): 8.750, Area (%): 99.92. 1H-NMR (400 MHz, CDC13): 5 8.12 (d, J = 1.20 Hz, 4H), 4.39- 4.36 (m, 2H), 4.29-4.27 (m, 2H), 1.77-1.58 (m, 2H), 1.04-1.45 (m, 28H), 0.84-1.00 (m, 20H).

[00129] Target B3 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., adipic acid (1), Chemical Formula: C6H20O4; Molecular Weight: 146.14 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

Target B3

[00130] Target B3 was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Viscosity properties for Target B3 are shown in Table 22. Characterization of Target B3: Chemical Formula: C32H62O4; Molecular Weight: 510.84 g/mol. LCMS: m\z: 511.5(M+H), RT (min): 7.520, Area (%): 92.50. HPLC: RT (min): 5.146, Area (%): 95.84. 1H-NMR (400 MHz, CDC13): 5 4.12-4.06 (m, 2H), 4.00-3.96 (m, 2H), 2.35-2.34 (m, 4H), 1.68-1.60 (m, 6H), 1.11-1.39 (m, 28H), 0.94-0.90 (m, 20H). The Noack volatility of Target B3 is about 5.27%, pour point is less than -80°C, and viscosity index is about 145.

Table 22 shows viscosity properties of Target B3.

[00131] Target B4 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., glutaric acid (1), Chemical Formula: C5H8O4; Molecular Weight: 132.12 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

Target B4

[00132] Target B4 was synthesized following generally similar synthesis and conditions purification as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target B4: Chemical Formula: C31H60O4. Molecular Weight: 496.82 g/mol. LCMS: m\z: 497.5 (M+H), RT (min): 7.466, Area (%): 97.69. GCMS: Mass not observed. HPLC: RT (min): 5.992, Area (%): 95.56. 1H-NMR (400 MHz, CDC13): 5 4.13-4.07 (m, 2H), 4.01-3.99 (m, 2H), 2.42-2.37 (m, 4H), 1.99-1.95 (m, 2H), 1.64-1.57 (m, 2H), 1.08-1.39 (m, 28H), 0.83-0.93 (m, 20H).

[00133] Target B5 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., succinic acid (1), Chemical Formula: C4H6O4; Molecular Weight: 118.09 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below: (2.4 eq)

Target B5

[00134] Target B5 was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target B5: Chemical Formula: C30H58O4. Molecular Weight: 482.79 g/mol. LCMS: m\z: 483.5 (M+H), RT (min): 5.117, Area (%): 95.08. 1H-NMR (400 MHz, CDC13): 5 4.14-4.02 (m, 2H), 4.01-3.98 (m, 2H), 2.65-2.63 (m, 4H), 1.63-1.59 (m, 4H), 1.08-1.39 (m, 27H), 0.82-0.94 (m, 19H).

[00135] Target B6 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., benzoic acid (1), Chemical formula: C7H6O2; Molecular weight: 122.12 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

2 (1-2 eq) vo , ,

Target B6

[00136] Target B6 was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target B6: Chemical Formula: C20H32O2; Molecular weight: 304.47 g/mol. GCMS: Mass not observed. HPLC: RT (min): 3.866, Area (%): 99.69. 1H-NMR (400 MHz, CDC13): 5 8.08-8.06 (m, 2H), 7.55-7.60 (m, 1H), 7.48-7.44 (m, 2H), 4.39-4.25 (m, 2H), 1.76-1.62 (m, 1H), 1.16-1.45 (m, 15H), 1.05-0.95 (m, 1H), 0.84-0.92 (m, 8H).

[00137] Target B7 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 2-hydroxybenzoic acid (1) (salicylic acid), Chemical Formula: C7H2O3; Molecular weight: 138.12 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

2 (1.2 eq)

1 DCM (lO vol), 16 h, RT

Target B7

[00138] Target B7 was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target B7: Chemical formula: C20H32O3. Molecular weight: 320.47 g/mol. LCMS: m\z: 321.3 (M+H), RT (min): 4.944, Area (%): 99.91. GCMS: Mass not observed. HPLC: RT (min): 3.939, Area (%): 99.83. 1H-NMR (400 MHz, CDC13): 5 10.88 (s, 1H), 7.86 (t, J = 8.00 Hz, 1H), 7.50-7.45 (m, 1H), 7.02-6.93 (m, 1H), 6.93-6.89 (m, 1H), 4.41-4.29 (m, 1H), 4.29-4.27 (m, 1H), 1.77-1.76 (m, 1H), 1.14-1.59 (m, 14H), 1.04-1.06 (m, 1H), 0.84-1.00 (m, 9H).

[00139] Target B8 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 3 -phenylpropanoic acid (1); Chemical Formula: C9H10O2; Molecular Weight: 150.18 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

Target B8

[00140] Target B8 was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target B8: Chemical Formula: C22H36O2; Molecular Weight: 332.53 g/mol. LCMS: m\z: 333.3 (M+H), RT (min): 3.703, Area (%): 98.89. HPLC: RT (min): 3.914, Area (%): 99.68. 1H-NMR (400 MHz, DMS0-d6): 5 7.29-7.16 (m, 5H), 4.02-3.89 (m, 2H), 2.87-2.83 (m, 2H), 2.64-2.59 (m, 2H), 1.51- 1.46 (m, 2H), 1.34-1.10 (m, 11H), 1.08-1.05 (m, 2H), 0.86-0.79 (m, 10H).

[00141] Target B9 is an example of a reaction where at step 1, precursor 42 (e.g., di(U7- imidazol-2-yl)methanone(l); chemical formula: C7H6N4O; molecular weight: 162.15 g/mol) was reacted with the disclosed C13 oxo alcohol (2) to form an intermediate product (3) (chemical formula: C17H30N2O2, molecular weight: 294.44 g/mol). At step 2, the intermediate product (3) was subsequently reacted with additional amounts of the disclosed C 13 oxo alcohol (2) to generate Target B9. The example reaction scheme is shown below:

1

Target B9

[00142] Target B9 was synthesized following generally similar synthesis and purification conditions as Target C9 below with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target B9: Chemical Formula: C27H54O3; Molecular Weight: 426.73 g/mol. LCMS: Mass not ionized, RT (min): 7.457, Area (%): 97.94. HPLC: RT (min): 5.974, Area (%): 98.54. 1H-NMR (400 MHz, CDC13): 5 4.17 (m, 2H), 4.06-4.05 (m, 2H), 1.60-1.66 (m, 8H), 1.52-1.45 (m, 4H), 1.29-1.39 (m, 6H), 1.11-1.19 (m, 6H), 0.95-1.10 (m, 2H), 0.83-0.92 (m, 24H).

[00143] Target B10 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., oxalic acid(l), chemical formular: C2H2O4, molecular weight: 90.03 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below: (2.4 eq)

Target B10

[00144] Target BIO was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target BIO: Chemical Formula: C28H54O4; Molecular Weight: 454.74 g/mol. GCMS: m\z: 454.5 (M)+, RT (min): 8.953, Area (%): 99.84. HPLC: RT (min): 4.934, Area (%): 97.89. 1H-NMR (400 MHz, CDC13): 5 4.34-4.30 (m, 2H), 4.22-4.20 (m, 2H), 1.72-1.70 (m, 3H), 1.11-1.42 (m, 31H), 0.91- 1.00 (m, 16H).

[00145] Target Bl 1 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., phosphoryl trichloride (1), chemical formula: CI3OP, molecular weight: 153.32 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

Target Bl 1

[00146] Target Bl l was synthesized following generally similar synthesis and purification conditions as Target Al 1 or Target Cl 1 below with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization ofTarget Bl l : Chemical Formula: C39H81O4P; Molecular Weight: 645.05 g/mol. HPLC: RT (min): 7.034, Area (%): 96.71. 1H-NMR (400 MHz, CDC13): 5 4.03-3.86 (m, 6H), 1.65-1.61 (m, 5H), 1.05-1.41 (m, 42H), 0.96-0.87 (m, 28H). [00147] Target B12 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 2-ethyl-2-methylheptanoic acid (1), chemical formula: C10H20O2, molecular weight: 172.27 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

(1.2 eq)

Target B 12

[00148] Target B12 was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Characterization of Target B12: Chemical formula: C23H46O2; Molecular Weight: 354.62 g/mol. GCMS: m\z: 354.4 (M)⁺. HPLC: RT (min): 4.782, Area (%): 99.71. 'H-NMR (400 MHz, CDC13): 5 4.11-3.97 (m, 2H), 1.59-1.56 (m, 2H), 1.52-1.50 (m, 3H), 1.48-1.28 (m, 15H), 1.18-1.06 (m, 12H), 0.95-0.88 (m, 12H).

[00149] Target B13 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., pivalic acid (1), chemical formula: C5H10O2; molecular weight: 102.13 g/mol) was reacted with the disclosed C13 oxo alcohol (2). The example reaction scheme is shown below:

Target B 13

[00150] Target B13 was synthesized following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. Viscosity properties for Target B13 are shown in Table 23. Characterization of Target A13 includes: Chemical Formula: C18H36O2; Molecular Weight: 284.48 g/mol. LCMS(ELSD): Mass not observed, RT (min): 3.183, Area (%): 99.86. GCMS: Mass not observed. 1H-NMR (400 MHz, CDC13): 5 4.11-3.97 (m, 2H), 1.24-1.38 (m, 14H), 1.16-1.22 (m, 14H), 0.82-0.95 (m, 6H). The Noack volatility of Target B13 is about 99.95% and pour point is less than -80°C.

Table 23 shows viscosity properties of Target B13.

[00151] Target B14 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., benzene- 1, 2, 4-tricarboxylic acid (1); chemical formula: CgHeOe; molecular weight: 210.14 g/mol) was reacted with the disclosed C13 oxo alcohol (2) using procedures known in the art to form an intermediate acid chloride which was then reacted with C13 oxo alcohol (2) in the presence of a pyridine base with a DMAP catalyst. The example reaction scheme is shown below:

Target B 14

Characterization of Target B 14: Chemical Formula: C48H84O6; Molecular Weight: 757.19 g/mol. LCMS(ELSD): m\z: 757.6 (M+H), RT (min): 4.117, Area (%): 98.05. HPLC: RT (min): 4.697, Area (%): 97.07. 1H-NMR (400 MHz, CDC13): 5 8.41 (s, 1H), 8.20 (d, J= 7.60 Hz, 1H), 7.77 (d, J= 6.00 Hz, 1H), 4.25-4.41 (m, 6H), 1.78-1.73 (m, 4H), 1.12-1.52 (m, 50H), 0.88-1.01 (m, 21H).

[00152] In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may have a KV at 100°C that is ranging from about 5 mm²/s to 1 mm²/s. In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may have a KV at 40°C that is ranging from about 40, 35, 30, or 25 mm²/s to about 1 mm²/s. In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may have a viscosity index that is greater than 140, 141, 142, or 143. In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may have a Noack TGA weight loss that is less than 7%, 6%, or 5%. In an embodiment, the ester composition 46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may have a KV at -20°C that is ranging from about 60 mm²/s to 1 mm²/s.

Examples of Esters Generated using LBA 32 (e.g., C17 oxo)

[00153] The following are example ester composition 46 generated using the LBA 32 (e.g., C17 oxo alcohol) as described by the methods of FIGS. 2 and 3. For simplicity, each reaction shows one example structure (i.e., representative structure) for a C17 oxo alcohol that may be used to generate the ester composition 46. However, it should be noted that the structure of the disclosed C17 oxo alcohol below is meant to be exemplary. It should be noted that in some instances when a KV is measured close to the freezing point of a respective ester composition 46, the KV may increase rapidly and be a value that is undesirable for use in certain applications. Nonetheless, certain esters may have desirable KVs above the freezing point.

[00154] Target Cl is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., phthalic acid (1), chemical formula: CsHeCU; molecular weight: 166.13 g/mol) was reacted with the disclosed 17 oxo alcohol (2) (chemical formula: C17H36O2; 3 -methyltetradecan- l-ol; molecular weight: 256.47 g/mol). Furthermore, it should be noted that the term C17 oxo alcohol (e.g., 3 -methylhexadecan- l-ol) may be used interchangeably with its isomeric name, to as hexadecan- l-ol. The example reaction scheme is shown below:

Chemical Formula: C₄₂H₇₄O₄ Molecular Weight: 643.05

Target Cl

[00155] Target Cl, bis (3-methytetradecyl)phthalate, was synthesized by adding EDC-HC1 (17.31 g, 90 mmol) and DMAP (2.65 g, 21.67 mmol)at room tempeature (RT) to a stirred solution including phthalic acid (6 g, 36.1 mmol)and LBA 32 C17 oxo alcohol (e.g., hexadecan- l-ol) (24.75 g, 108 mmol) in DCM (250 mL). The resulting reaction mixture was stirred at RT for 16 h. Completion of reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water (100 mL) and extracted with DCM (2x200 mL). The combined organic layer was dried over anhydrous ISfeSCU and concentrated under reduced pressure to afford the crude product as colorless liquid (23g). The crude was purified by column chromatography using Biotage isolera snap-340 g (230-400 silica gel), wherein desired product was eluted in 2% ethyl acetate in petroleum ether. Pure fractions were collected and concentrated under reduced pressure to afford bi s(3 -methyltetradecyl) phthalate (10.5 g, 17.53 mmol, 48.5 % yield)as colorless liquid. Characterization of Target Cl : Chemical Formula: C42H66O4. Molecular Weight: 653.05 g/mol. LCMS: m\z: 643.05 (M+H), RT (min): 8.70, Area (%): 96.03 (Desired mass is not ionized). HPLC: RT (min): 7.52, Area (%): 98.57. 'H-NMR (400 MHz, CDC13): 5 7.64 (d, J = 67.20 Hz, 2H), 7.54 (d, J= 3.60 Hz, 2H), 4.36-4.24 (m, 4H), 1.75-0.70 (m, 3H), 1.28-1.01 (m, 42H), 0.99-0.88 (m, H).

[00156] Target C2 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., terephthalic acid (1), chemical formula: CsHeCL, Molecular Weight: 166.13 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

² (3 eq)

Target C2

[00157] Target C2 was synthesized via a Steglich esterification reaction. For example, Target C2 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), wherein desired product was eluted in 3% ethyl acetate in petroleum ether. Pure fractions were collected and concentrated under reduced pressure to get bi s(3 -methyltetradecyl) terephthalate (16.3 g, 27.8 mmol, 77 % yield)as colorless liquid. Characterization of Target C2: Chemical Formula: C42H74O4, Molecular weight: 643.05 g/mol. LCMS: m\z: 643.05 (M+H), RT (min): 5.88, Area (%): 91.52 (Desired mass is not ionized). HPLC: RT (min): 6.23, Area (%): 99.38. 'H-NMR (400 MHz, CDC13): 5 8.11 (s, 4H), 4.40-4.27 (m, 4H), 1.81-1.77 (m, 4H), 1.38-1.15 (m, 45H), 1.13-0.97 (m, 18H). [00158] Target C3 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., adipic acid (1), Chemical Formula: C6H20O4; Molecular Weight: 146.14 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

[00159] Target C3 was synthesized via a Steglich esterification reaction following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), wherein desired product was eluted in 6% ethyl acetate in petroleum ether. Pure fractions was collected and concentrated under reduced pressure to get 22g of desired product. The 22 g of compound was further purified by bulb-to-bulb distillation at 0.015 mbar and 60°C to afford bis(3- methyltetradecyl) adipate (18.3 g, 32.2 mmol, 94 % yield) as a pale yellow liquid. Viscosity properties for Target C3 are shown in Table 24. Characterization of Target C3 : Chemical Formula: C40H78O4; Molecular Weight: 623.06 g/mol. LCMS: m\z: 623.06 (M+H), RT (min): 8.74, Area (%): 99.49 (Desired mass is not ionized). HPLC: RT (min): 7.59, Area (%): 99.86. 'H-NMR (400 MHz, CDC13): 5 4.12-4.05 (m, 4H), 2.35-2.34 (m, 4H), 1.68-1.61 (m, 8H), 1.61-1.18 (m, 36H), 1.18-1.16 (m, 6H), 1.16-0.92 (m, 19H). The Noack volatility of Target C3 is about 2.76%, pour point is less than -69°C, and viscosity index is about 159.

Table 24 shows viscosity properties of Target C3.

[00160] Target C4 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., glutaric acid (1), Chemical Formula: C5H8O4; Molecular Weight: 132.12 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

Target C4

[00161] Target C4 was synthesized via a Steglich esterification reaction following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), wherein desired product was eluted in 4% ethyl acetate in petroleum ether. Pure fractions was collected concentrated under reduced pressure to get 21 g of desired product as pale yellow liquid. The 21 g compound was further purified by bulb-to-bulb distillation at 0.015 mbar and 60°C to afford bi s(3 -methyltetradecyl) glutarate (19.7 g, 35.6 mmol, 94 % yield). Characterization of Target C4: Chemical Formula: C39H76O4. Molecular Weight: 609.03 g/mol. LCMS: m\z: 609.03 (M+H), RT (min): 8.64, Area (%): 96.45. HPLC: RT (min): 7.43, Area (%): 99.90. 'H-NMR (400 MHz, CDC13): 5 4.12-4.00 (m, 4H), 2.41-2.36 (m, 4H), 1.98-1.95 (m, 2H), 1.67-1.61 (m, 4H), 1.63-1.43 (m, 36H), 1.58-1.19 (m, 6H), 1.18-1.11 (m, 19H).

[00162] Target C5 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., succinic acid (1), Chemical Formula: C4H6O4; Molecular Weight: 118.09 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

Target C5

[00163] Target C5 was synthesized via a Steglich esterification reaction following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), Desired product was eluted in 2% ethyl acetate in petroleum ether. Pure fractions was collected and concentrated under reduced pressure to get bi s(3 -methyltetradecyl) succinate (11.5 g, 21.13 mmol, 41.6 % yield) as colorless oil. Characterization ofTarget C5: Chemical Formula: C38H74O4. Molecular Weight: 595.01 g/mol. LCMS: m\z: 595.01 (M+H), RT (min): 5.89, Area (%): 98.98 (Desired mass is not ionized). HPLC: RT (min): 6.30, Area (%): 99.75. 'H-NMR (400 MHz, CDC13): 5 4.14-4.10 (m, 2H), 4.04-3.98 (m, 2H), 2.65 (s, 4H), 1.64-1.57 (m, 2H), 1.20-1.11 (m, 44H), 0.92-0.85 (m, 20H).

[00164] Target C6 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., benzoic acid (1), Chemical formula: C7H6O2; Molecular weight: 122.12 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

Target C6

[00165] Target C6 was synthesized via a Steglich esterification reaction following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), wherein the desired product was eluted in 2% ethyl acetate in petroleum ether. Pure fractions were collected and concentrated under reduced pressure to get 3 -methyltetradecyl benzoate (11 g, 32.7 mmol, 66.7 % yield) as colorless oil. Characterization of Target C6: Chemical Formula: C24H40O2; Molecular weight: 360.58 g/mol. LCMS: m\z: 360.58 (M+H), RT (min): 6.20, Area (%): 99.74 (Desired mass is not ionized). HPLC: RT (min): 4.05, Area (%): 99.58. 'H-NMR (400 MHz, CDC13): 5 8.07-8.07 (m, 2H), 7.58-7.56 (m, 1H), 7.47-7.43 (m, 2H), 4.40-4.26 (m, 2H), 1.80-1.49 (m, 2H), 1.15-1.04 (m, 24H), 0.88-0.84 (m, 10H).

[00166] Target C7 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 2-hydroxybenzoic acid (1) (salicylic acid), Chemical Formula: C7H2O3; Molecular weight: 138.12 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

Target C7

[00167] Target C7 was synthesized via a Steglich esterification reaction following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by gravity column chromatography using 230-400 silica gel. Desired product was eluted in 1% ethyl acetate in petroleum ether. Pure fractions were collected and concentrated under reduced pressure to get 3 -methyltetradecyl 2-hydroxybenzoate (7 g, 20.04 mmol, 27.7 % yield) as a colorless oil. Characterization of Target C7: Chemical formula: C24H40O3. Molecular weight: 376.58 g/mol. LCMS: m\z: 376.58 (M+H), RT (min): 4.61, Area (%): 98.41 (Desired mass is not ionized). HPLC: RT (min): 4.55, Area (%): 99.88. 'H-NMR (400 MHz, CDC13): 5 10.88 (s, 1H), 7.86-7.84 (m, 1H), 7.50-7.48 (m, 1H), 7.01-6.93 (m, 1H), 6.91-6.89 (m, 1H), 4.41-4.38 (m, 1H), 4.37-4.28 (m, 1H), 1.77-1.75 (m, 2H), 1.16-1.04 (m, 24H(e), 0.89-0.84 (m, 10H).

[00168] Target C8 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 3 -phenylpropanoic acid (1); Chemical Formula: C9H10O2; Molecular Weight: 150.18 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

Target C8

[00169] Target C8 was synthesized via a Steglich esterification reaction following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by gravity column chromatography using 230-400 silica gel. Desired products were eluted in 2% ethyl acetate in petroleum ether. Pure fractions were collected and concentrated under reduced pressure to yield 3 -methyltetradecyl 3-phenylpropanoate (14.5 g, 39.8 mmol, 85 % yield) as a colorless oil. Characterization of TargetB8: Chemical Formula: C26H44O2; Molecular Weight: 388.64 g/mol. LCMS: m\z: 388.64 (M+H), RT (min): 6.25, Area (%): 97.91 (Desired mass is not ionized). HPLC: RT (min): 4.54, Area (%): 99.61. 'H-NMR (400 MHz, CDC13): 5 7.33-7.31 (m, 2H), 7.29-7.24 (m, 3H), 4.11-4.07 (m, 2H), 3.00-2.96 (m, 2H), 2.68-2.67 (m, 2H), 1.61-1.57 (m, 1H), 1.10-0.91 (m, 19H), 1.15-1.10 (m, 3H), 0.89-0.85 (m, 10H).

[00170] Target C9 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where at step 1, precursor 42 (e.g., di(U/-imidazol-2- yl)methanone(l); chemical formula: C7H6N4O; molecular weight: 162.15 g/mol) was reacted with the disclosed C17 oxo alcohol (2) to form an intermediate product (3) (chemical formula: C21H38N2O2, molecular weight: 350.55 g/mol). At step 2, the intermediate product (3) was subsequently reacted with additional amounts of the disclosed C17 oxo alcohol (2) to generate Target C9. The example reaction scheme is shown below:

Target C9

[00171] Step 1 : To a stirred solution 3 -methyltetradecan- l-ol (e.g., LBA 32 C17 oxo alcohol) (30.0 g, 131 mmol)in DCM (300 mL)was added to di(lH-imidazol-l-yl)methanone (27.7 g, 171 mmol)at room temperature. The resulting reaction mixture was stirred at room temperature for 16 h. Completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with DCM and washed with cold water (200 mL). An organic layer was separated and concentrated under reduced pressure to afford the crude as a pale yellow liquid compound (45 g). The crude was purified by gravity column chromatography using 230-400 silica gel. The desired product was eluted in 12% ethyl acetate in petroleum ether. Pure fractions were collected and concentrated under reduced pressure to get the intermediate product, 3- methylhexadecyl IH-imidazole-l -carboxylate (3) (36 g, 107 mmol, 82 % yield) as a colorless liquid. LCMS: m\z: 350.55 (M+H), RT (min): 2.69, Area (%): 96.60 (Desired mass is not ionized). [00172] Step 2: To a stirred solution of 3 -methylhexadecyl lH-imidazole-2-carboxylate (36g, 112 mmol)in dimethyl formamide (DMF) (150 mL), sodium hydride (NaH) (60%) (5.80 g, 145 mmol)was added at 0 °C, after which the reaction mixture was heated or 2 h at 80 °C. Next, the reaction was cooled to room temperature and hexadecan- l-ol (e.g., LB A 32 C17 oxo alcohol) (33.1g, 145.mmol)was added. The resulting reaction mixture was stirred at room temperature for 16 h. Completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice and diluted with ethyl acetate (200 mL). Organic layer was washed with cold water (200 mL) and extracted with ethyl acetate (2x200 mL). The combined organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the crude (35g) as a pale yellow liquid. The crude was purified by gravity column chromatography using 230-400 silica gel. Desired product was eluted in 1% ethyl acetate in petroleum ether. Pure fractions collected was concentrated under reduced pressure to get bi s(3 -methyltetradecyl) carbonate (11.5 g, 23.58 mmol, 21.12 % yield) as a colorless oil. Characterization of Target C9: Chemical Formula: C35H70O3; Molecular Weight: 538.94 g/mol. LCMS: m\z: 538.94 (M+H), RT (min): 8.74, Area (%): 80% (Desired mass is not ionized). HPLC: RT (min): 5.25, Area (%): 98.64. 'H-NMR (400 MHz, CDC13): 5 4.18-4.15 (m, 2H), 4.14-4.05 (m, 2H), 1.67-1.60 (m, 2H), 1.28-1.11 (m, 47H), 0.97-0.92 (m, 22H).

[00173] Target CIO is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., oxalic acid (1), chemical formular: C2H2O4, molecular weight: 90.03 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

Target CIO

[00174] Target CIO was synthesized via the following: in a Dean Stark apparatus, a solution of hexadecan- l-ol (e.g., LBA 32 C17 oxo alcohol) (36.5 g, 160 mmol) in toluene (150 mL)was stirred at room temperature. Subsequently, sulfuric acid (1.307 g, 13.33 mmol) was added. The resulting reaction mixture was heated at 80 °C. Next, oxalic acid (6 g, 66.6 mmol) was added portion wise to the reaction mixture. The reaction continued at 140°C for 16 h. Completion of the reaction was monitored by TLC, and after completion, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to generate a crude residue. The crude residue was diluted with ethyl acetate and washed with cold water (2 x 150 mL). The organic layer was separated and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude as a pale yellow liquid (35 g). The crude was purified by gravity column chromatography using 230-400 silica gel. Desired products were eluted in 3% ethyl acetate in petroleum ether. Pure fractions collected were concentrated under reduced pressure to get bi s(3 -methyltetradecyl) oxalate (13.5 g, 26.2 mmol, 39.3 % yield)as a colorless oil. Characterization of Target CIO: Chemical Formula: C36H70O4; Molecular Weight: 566.95 g/mol. LCMS: m\z: 566.95 (M+H), RT (min): 8.46, Area (%): 98.80 (Desired mass is not ionized). HPLC: RT (min): 6.02, Area (%): 99.72. ‘H-NMR (400 MHz, CDC13): 5 4.32-4.29 (m, 2H), 4.28-4.23 (m, 2H), 1.75-1.70 (m, 4H), 1.50-1.27 (m, 50H), 1.18-1.12 (m, 22H).

[00175] Target Cll is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., phosphoryl trichloride (1), chemical formula: CI3OP, molecular weight: 153.32 g/mol) was reacted with the disclosed C17 oxo alcohol. The example reaction scheme is shown below:

Target Cl l

[00176] Target Cl l was synthesized via the following: To a stirred solution of heptadecan- l-ol (e.g., LBA 32 C17 oxo alcohol) (67.0 g, 293 mmol) in DCM (200 mL), TEA (40.9 mL, 293 mmol) and POC13 (6.08 mL, 65.2 mmol) were added at 0 °C. The resulting reaction mixture was stirred at room temperature for 16 h. Completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered using Celite bed, washed with n-hexane, and the filtrate was concentrated to give semi solid, which was further filtered and washed with n-hexane. The filtrate was concentrated to give crude compound (80 g). The crude compound tris(3- methyltetradecyl) phosphate (80 g, 110 mmol) was subjected to distillation up to 170°C. It should be noted that an air condenser was used to avoid the solid formation in the condenser line. The starting material was distilled at 170°C. (0.01 mbar vacuum): 10 g. Remaining residue (65 g) containing the product was obtained. The residue was diluted with pet ether (100 mL) and the organic layer was washed with water (100 mL), brine solution (100 mL), dried over ISfeSCU, filtered, and concentrated to give 53 g crude product. This crude compound was purified by flash column chromatography (silica-gel, 100 -200 mesh size). Desired products were eluted in 3% ethyl acetate in petroleum ether. Pure fractions collected were concentrated under reduced pressure to get tri s(3 -methyltetradecyl) phosphate (25.5 g, 34.8 mmol, 31.7 % yield) as a colorless oil. Characterization of Target Cl l: Chemical Formula: C51H105O4P; Molecular Weight: 813.57 g/mol. LCMS: m\z: 813.37 (M+H), RT (min): 7.78, Area (%): 99.45 (Desired mass is not ionized). 'H-NMR (400 MHz, CDC13): 5 4.06-4.01 (m, 6H), 1.81-1.69 (m, 3H), 1.27-1.02 (m, 60H), 0.99- 0.90 (m, 27H).

[00177] Target Cll is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., 2-ethyl-2-methylheptanoic acid (1), chemical formula: C10H20O2, molecular weight: 172.27 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

Target C12

[00178] Target C12 was synthesized following generally similar synthesis conditions as Target A12 with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents and/or temperature. The crude was purified by gravity column chromatography using 230-400 silica gel. Desired products were eluted in 2% ethyl acetate in petroleum ether. Pure fractions collected were concentrated under reduced pressure to get 3-methyltetradecyl 2-ethyl-2- methylheptanoate (6 g, 15.52 mmol, 26.7 % yield) as colorless oil. Characterization of Target C12: Chemical formula: C27H54O2; Molecular Weight: 410.73 g/mol. LCMS: m\z: 410.73 (M+H), RT (min): 12.67, Area (%): 99.07 (Desired mass is not ionized). HPLC: RT (min): 5.26, Area (%): 98.62. ‘H-NMR (400 MHz, CDC13): 54.11-4.05 (m, 2H), 1.61-1.51 (m, 6H), 1.45-1.18 (m, 28H), 1.14-1.01 (m, 17H).

[00179] Target C13 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., pivalic acid (1), chemical formula: C5H10O2; molecular weight: 102.13 g/mol) was reacted with the disclosed C17 oxo alcohol (2).

The example reaction scheme is shown below:

Target C13

[00180] Target C13 was synthesized following generally similar synthesis conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The crude was purified by gravity column chromatography using 230-400 silica gel. Desired product was eluted in 1% ethyl acetate in petroleum ether. Pure fractions collected were concentrated under reduced pressure to get 3- methyltetradecyl pivalate (5.5 g, 17.55 mmol, 29.9 % yield) as colorless liquid. Viscosity properties for Target C13 are shown in Table 25. Characterization of Target C13 includes: Chemical Formula: C22H44O2; Molecular Weight: 340.59 g/mol. LCMS: m\z: 340.59 (M+H), RT (min): 6.63, Area (%): 100 (Desired mass is not ionized). HPLC: RT (min): 4.70, Area (%): 99.07. 'H-NMR (400 MHz, CDC13): 5 4.12-4.10 (m, 2H), 1.22-1.19 (m, 32H), 0.88-0.86 (m, 10H). The Noack volatility of Target C13 is about 46.26%, pour point is less than -89°C, and viscosity index is about 102.

Table 25 shows viscosity properties for Target C13.

[00181] Target C14 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., benzene- 1, 2, 4-tricarboxylic acid (1); chemical formula: CgHeOe; molecular weight: 210.14 g/mol) was reacted with the disclosed C17 oxo alcohol (2). The example reaction scheme is shown below:

Target C14

[00182] Step 1 : To a stirred solution of benzene- 1,2, 4-tricarboxylic acid (5 g, 23.79 mmol) in toluene (60 mL), oxalyl chloride (9.18 mL, 107 mmol) and DMF (3 drops) was added and stirred at 80 °C for 2.5 h. Completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to get crude benzene- 1, 2, 4-tricarbonyl trichloride (6.5 g, 24.48 mmol, 103 % yield) as a pale brown gummy liquid. LCMS: m\z:265.47 (Desired mass not observed). The crude processed at step-2 based on the results of the TLC without any purification.

[00183] Step 2: To a stirred solution of benzene- 1,2, 4-tricarbonyl trichloride (3) (6.0 g, 22.60 mmol) in DCM (120 mL), pyridine (2.91 mL, 33.9 mmol), followed by 4-dimethylaminopyridine (0.276 g, 2.260 mmol) was added at 0 °C. The reaction mixture stirred for 10 min and hexadecan- l-ol (e.g., LBA 32 C17 oxo alcohol) (25.8 g, 113 mmol) was added. The resulting reaction mixture stirred at room temperature for 16 h. Completion of the reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with water (100 mL) and extracted with DCM (200 mL x 2). The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure (bath temperature: 45°C) to afford crude (pale brown gummy liquid). The crude (30 g) was purified by column chromatography using Biotage isolera snap-340 g (230-400 silica gel), Desired product was eluted in 1% ethyl acetate in petroleum ether. Pure fractions collected were concentrated under reduced pressure to get 19g of desired product as pale brown liquid. 19 g compound was further purified by bulb-to-bulb distillation at 0.001 mbar and 130°C to afford the residue tri s(3 -methyltetradecyl) benzene- 1, 2, 4-tricarboxylate (18 g, 19.83 mmol, 88 % yield) as a pale yellow liquid. Characterization of Target C14: Chemical Formula: CeoHiosOe; Molecular Weight: 924.81 g/mol. LCMS: 924.81 (M+H), RT (min): 4.71, Area (%): 99.14. HPLC: RT (min):5.32, Area (%): 98.99 'H-NMR (400 MHz, CDC13): 5 8.41 (m, 1H), 8.21-8.19 (m, 1H), 7.77-7.76 (m, 1H), 4.39-4.37 (m, 2H), 1.77-1.61 (m, 6H), 1.17-0.97 (m, 105H). [00184] In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may have a KV at 100°C that is ranging from about 8, 7, or 6 mm²/s to about 0.1 mm²/s. In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may have a KV at 40°C that is ranging from about 40, 35, or 30 mm²/s to about 0.1 mm²/s. In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may have a Noack TGA volatility that is less than 6%, 5%, 4%, or 3%. In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may have a viscosity index that is greater than 145, 150, or 155. In an embodiment, the diester composition 66,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may have a viscosity index that is about 160.

Examples of Neopentanoic Esters Generated using LBA 32

[00185] The following are example neopentanoic ester compositions 66, 46 generated using the LBA 32 (e.g., C9 oxo alcohol, C13 oxo alcohol, C17 oxo alcohol) as described by the methods of FIGS. 2 and 4. For simplicity, each reaction shows one example structure (i.e., representative structure) for LBA 32 (e.g., C9 oxo alcohol, C13 oxo alcohol, C17 oxo alcohol) that may be used to generate the neopentanoic ester compositions 66, 46. However, it should be noted that the structure of the disclosed C9 oxo alcohol, C13 oxo alcohol, C17 oxo alcohol below is meant to be exemplary. It should be noted that in some instances when a KV is measured close to the freezing point of a respective ester composition 46, the KV may increase rapidly and be a value that is undesirable for use in certain applications. Nonetheless, certain esters may have desirable KVs above the freezing point.

[00186] Target DI is an example of a comparative ester where precursor 42 (e.g., pivalic acid (1) chemical formula: C5H10O2; molecular weight: 102.13 g/mol) was reacted with a comparative alcohol (2) (e.g., combination of 70 wt.% lauryl alcohol (C12) (2a) and 30 wt.% myristyl alcohol (C14) (2b). The example reaction scheme is shown below:

Target DI [00187] Target DI was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The product was a colorless liquid including a mixture of products. Characterization of Target DI : Chemical Formula (3): C17H34O2; Molecular Weight (3): 270.46 g/mol; Chemical Formula (4): C19H38O2; Molecular Weight (4): 298.51 g/mol. LCMS: m\z:Not ionized (M+H), RT (min): 12.657, Area (%): 96.75. GCMS: m\z: 270.46 (M) ⁺, RT (min): 6.621, Area (%): 68.81. GCMS: m\z: 298.51 (M) ⁺, RT (min): 7.163, Area (%): 30.66. HPLC: RT (min): 4.300, Area (%): 95.31. 'H-NMR (400 MHz, CDC13): 5 4.06 (t, J = 6.80 Hz, 2H), 1.64 (t, J = 6.80 Hz, 2H), 1.20 (s, 18H), 1.16 (s, 9H), 0.92 (t, J= 4.40 Hz, 3H).

[00188] Target D2 is an example a comparative ester where precursor 42 (e.g., pivalic acid (1) chemical formula: C5H10O2; molecular weight: 102.13 g/mol) was reacted with a comparative alcohol (2) (e.g., linear alcohol, C15H32O, molecular weight: 228.42 g/mol). The example reaction scheme is shown below: , ,

Target D2

[00189] Target D2 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The product was a colorless liquid. Viscosity properties of Target D2 are shown in Table 26. Characterization of Target D2: Chemical Formula: C20H40O2; Molecular Weight: 312.54 g/mol. LCMS: m\z:285 (M+H), RT (min): 3.318, Area (%): 31.04. LCMS: m\z:313 (M+H), RT (min): 3.691, Area (%): 68.95. GCMS: m\z: 313 (M)⁺, RT (min): 6.423 to 7.967, Area (%): 91.97. HPLC: RT (min): 4.107, Area (%): 21.31 HPLC: RT (min): 4.449, Area (%): 78.68. 'H-NMR (400 MHz, CDC13): 54.06 (t, J= 6.80 Hz, 2H), 1.63 (t, = 2.00 Hz, 2H), 1.23 (s, 41H), 0.95-0.88 (m, 6H).

Table 26 shows viscosity properties of Target D2.

[00190] Target D3 is an example of a comparative ester where precursor 42 (e.g., pivalic acid (1) chemical formula: C5H10O2; molecular weight: 102.13 g/mol) was reacted with a comparative alcohol (2) (e.g., Comparative 2 C13 alcohol, chemical formula: C13H28O; molecular weight: 200.37 g/mol). The example reaction scheme is shown below: , ,

Target D3

[00191] Target D3 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The product was a colorless liquid. Viscosity properties for Target D3 are shown in Table 27. Characterization of Target D3: Chemical Formula: CisHseCh; Molecular Weight: 284.48 g/mol. LCMS: m\z:284.3 (M+H), RT (min): 3.097, Area (%): 99.80. HPLC: RT (min): 7.930, Area (%): 99.53. 'H-NMR (400 MHz, CDC13): 54.11-4.08 (m, 2H), 1.65-1.61 (m, 1H), 1.17-1.06 (m, 7H), 1.17 (s, 11H), 1.10-1.06 (m, 3H), 0.83-0.80 (m, 13H). The Noack volatility of Target D3 is about 100%, pour point is less than -81 °C, and viscosity index is about 102.

[00192] Table 27 shows viscosity properties for Target D3.

[00193] Target D4 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., pivalic acid (1) chemical formula: C5H10O2; molecular weight: 102.13 g/mol) was reacted with the disclosed C13 oxo alcohol (2) (e.g., LBA 32; chemical formula: C13H28O; molecular weight: 200.37 g/mol). The example reaction scheme is shown below:

DCM, RT,16h

Target D4 [00194] Target D4 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The product was a colorless liquid. Viscosity properties of Target D4 are shown in Table 28. Characterization of Target D4: Chemical formula: CisHaeCh. Molecular weight: 284.48 g/mol. GCMS: m\z: 284.48 (M) ⁺, RT (min): 6.192 to 6.716, Area (%): 95.01. HPLC: RT (min): 8.009, Area (%): 99.79.¹H-NMR (400 MHz, CDC13): 5 4.11-4.06 (m, 2H), 3.99-3.97 (m, 1H), 1.64-1.58 (m, 3H), 1.31 (s, 33H), 0.96-0.90 (m, 14H).

Table 28 shows viscosity properties of Target D4.

[00195] Target D5 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., pivalic acid (1) chemical formula:

C5H10O2; molecular weight: 102.13 g/mol) was reacted with the disclosed C17 oxo alcohol (2) (e.g., LBA 32; chemical formula: C17H36O2; 3 -methyltetradecan- l-ol; molecular weight: 256.47 g/mol). The example reaction scheme is shown below: Target D5

[00196] Target D5 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target Al with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions. The product was a colorless liquid. Viscosity properties of Target D5 are shown in Table 29. Characterization of Target D5: Chemical formula: C20H40O2. Molecular weight: 312.54 g/mol. GCMS: m\z: 312.5 (M) ⁺, RT (min): 7.266 to 7.711, Area (%): 97.67. HPLC: RT (min): 4.681, Area (%): 99.88. 'H-NMR (400 MHz, CDC13): 5 4.10-4.06 (m, 2H), 1.63-1.56 (m, 2H), 1.44 (s, 18H), 1.15 (s, 10H), 1.09-0.93 (m, 1H), 0.88-0.85 (m, 10H).

Table 29 shows viscosity properties of Target D5.

[00197] In an embodiment, the neopentanoic esters 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about 40°C ranging from about 0.1 mm²/s to about 10 mm²/s, about 0.1 to about 7 mm²/s, about 2 to 4.5 mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, or about 10 mm²/s. The neopentanoic esters 66,46 may exhibit a DV at about 40°C ranging from about 0.1 mPa-s to about 10 mPa-s, about 0.1 to 7 mPa-s, about 2 to 4.5 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, or about 10 mPa-s. The neopentanoic esters 66,46 may exhibit a density at about 40°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00198] In an embodiment, the neopentanoic esters 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about 100°C ranging from about 0.1 mm²/s to about 10 mm²/s, about 1 to about 5 mm²/s, about 1 to 4 about mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, or about 10 mm²/s. The neopentanoic esters 66,46 may exhibit a DV at about 100°C ranging from about 0.1 mPa-s to about 10 mPa-s, about 1 to 10 mPa-s, about 1 to 5 mPa-s, about 1 to 4 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, or about 10 mPa-s. The neopentanoic esters 66,46 may exhibit a density at about 100°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00199] In an embodiment, the neopentanoic esters 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about -35°C ranging from about 0.1 mm²/s to about 200 mm²/s, about 10 to about 175 mm²/s, about 20 to 150 about mm²/s, about 30 to about 125 mm²/s, about 40 to about 100 mm²/s, about 50 to 75 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, or about 200 mm²/s. The neopentanoic esters 66,46 may exhibit a DV at about -35°C ranging from about 0.1 mPa-s to about 200 mPa-s, about 10 to about 175 mPa-s, about 20 to 150 about mPa-s, about 30 to about 125 mPa-s, about 40 to about 100 mPa-s, about 50 to 75 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, or about 200 mPa-s. The neopentanoic esters 66,46 may exhibit a density at about -35°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00200] In an embodiment, the neopentanoic esters 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about -20°C ranging from about 0.1 mm²/s to about 50 mm²/s, about 5 to about 45 mm²/s, about 10 to 40 about mm²/s, about 15 to about 35 mm²/s, about 20 to about 30 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mm²/s. The neopentanoic esters 66,46 may exhibit a DV at about -20°C ranging from about 0.1 mPa-s to about 50 mPa-s, about 5 to about 45 mPa-s, about 10 to 40 about mPa-s, about 15 to about 35 mPa-s, about 20 to about 30 mPa-s such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mPa-s. The neopentanoic esters 66,46 may exhibit a density at about -20°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00201] In an embodiment, the neopentanoic esters 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about -10°C ranging from about 0.1 mm²/s to about 50 mm²/s, about 5 to about 45 mm²/s, about 10 to 40 about mm²/s, about 15 to about 35 mm²/s, about 20 to about 30 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mm²/s. The neopentanoic esters 66,46 may exhibit a DV at about -10°C ranging from about 0.1 mPa-s to about 50 mPa-s, about 5 to about 45 mPa-s, about 10 to 40 about mPa-s, about 15 to about 35 mPa-s, about 20 to about 30 mPa-s such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mPa-s. The neopentanoic esters 66,46 may exhibit a density at about -10°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00202] In an embodiment, the neopentanoic esters 66,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about 0°C ranging from about 0.1 mm²/s to about 50 mm²/s, about 5 to about 45 mm²/s, about 10 to 40 about mm²/s, about 15 to about 35 mm²/s, about 20 to about 30 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mm²/s. The neopentanoic esters 66,46 may exhibit a DV at about 0°C ranging from about 0.1 mPa-s to about 50 mPa-s, about 5 to about 45 mPa-s, about 10 to 40 about mPa-s, about 15 to about 35 mPa-s, about 20 to about 30 mPa-s such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mPa-s. The neopentanoic esters 66,46 may exhibit a density at about 0°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00203] In an embodiment, the neopentanoic ester compositions 66,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may exhibit a KV at about 40°C ranging from about 0.1 mm²/s to about 15 mm²/s, about 1 to about 12 mm²/s, about 2 to 11 about mm²/s, about 3 to about 10 mm²/s, about 4 to about 9 mm²/s, about 5 to 8 mm²/s, about 1 to 3 mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mm²/s. The neopentanoic ester compositions 66,46 may exhibit a DV at about 40°C ranging from about 0.1 mPa-s to about 15 mPa-s, about 1 to 12 mPa-s, about 2 to 11 mPa-s, about 3 to 10 mPa-s, about 4 to 9 mPa-s, about 5 to 8 mPa-s, about 1 to 3 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mPa-s. The neopentanoic ester compositions 66,46 may exhibit a density at about 40°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00204] In an embodiment, the neopentanoic ester compositions 66,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may exhibit a KV at about 100°C ranging from about 0.1 mm²/s to about 15 mm²/s, about 1 to about 12 mm²/s, about 1 to about 10 mm²/s, about 1 to 7 about mm²/s, about 1 to about 5 mm²/s, about 1 to about 3 mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mm²/s. The neopentanoic ester compositions 66,46 may exhibit a DV at about 100°C ranging from about 0.1 mPa-s to about 15 mPa-s, about 1 to 12 mPa-s, about 1 to 10 mPa-s, aboutl to 7 mPa-s, about 1 to 5 mPa-s, about 1 to 3 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mPa-s. The neopentanoic ester compositions 66,46 may exhibit a density at about 100°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00205] In an embodiment, the neopentanoic ester compositions 66,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may exhibit a KV at about -35°C ranging from about 0.1 mm²/s to about 500 mm²/s, about 50 to about 475 mm²/s, about 75 to 450 about mm²/s, about 350 to about 425 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, about 200, about 225, about 250, about 275, about 300, about 325, about 350, about 375, about 400, about 425, about 450, about 475, or about 500 mm²/s. The neopentanoic ester compositions 66,46 may exhibit a DV at about -35°C ranging from about 0.1 mPa-s to about 500 mPa-s, about 50 to about 475 mPa-s, about 75 to 450 about mPa-s, about 350 to about 425 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, about 200, about 225, about 250, about 275, about 300, about 325, about 350, about 375, about 400, about 425, about 450, about 475, or about 500 mPa-s. The neopentanoic ester compositions 66,46 may exhibit a density at about -35°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00206] In an embodiment, the neopentanoic ester compositions 66,46 generated using the disclosed LB A 32 (e.g., C17 oxo alcohol) may exhibit a KV at about -20°C ranging from about 0.1 mm²/s to about 200 mm²/s, about 10 to about 175 mm²/s, about 20 to 150 about mm²/s, about 30 to about 125 mm²/s, about 40 to about 100 mm²/s, about 50 to 75 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, or about 200 mm²/s. The neopentanoic ester compositions 66,46 may exhibit a DV at about -20°C ranging from about 0.1 mPa-s to about 200 mPa-s, about 10 to about 175 mPa-s, about 20 to 150 about mPa-s, about 30 to about 125 mPa-s, about 40 to about 100 mPa-s, about 50 to 75 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, or about 200 mPa-s. The neopentanoic ester compositions 66,46 may exhibit a density at about -20°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00207] In an embodiment, the neopentanoic ester compositions 66,46 generated using the disclosed LB A 32 (e.g., C17 oxo alcohol) may exhibit a KV at about -10°C ranging from about 0.1 mm²/s to about 70 mm²/s, about 5 to about 45 mm²/s, about 10 to 40 about mm²/s, about 15 to about 35 mm²/s, about 20 to about 30 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, or about 70 mm²/s. The neopentanoic ester compositions 66,46 may exhibit a DV at about -10°C ranging from about 0.1 mPa-s to about 70 mPa-s, about 5 to about 55 mPa-s, about 10 to 55 about mPa-s, about 20 to about 55 mPa-s, about 30 to about 30 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mPa-s. The neopentanoic ester compositions 66,46 may exhibit a density at about -10°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00208] In an embodiment, the neopentanoic ester compositions 66,46 generated using the disclosed LB A 32 (e.g., C17 oxo alcohol) may exhibit a KV at about 0°C ranging from about 0.1 mm²/s to about 50 mm²/s, about 5 to about 45 mm²/s, about 10 to 40 about mm²/s, about 15 to about 35 mm²/s, about 20 to about 30 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mm²/s. The neopentanoic ester compositions 66,46 may exhibit a DV at about 0°C ranging from about 0.1 mPa-s to about 60 mPa-s, about 5 to about 55 mPa-s, about 40 to about 55 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, or about 60 mPa-s. The neopentanoic ester compositions 66,46 may exhibit a density at about 0°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00209] In general, the disclosed neopentanoic ester compositions 66, 46 exhibit advantageous properties. For example, Target D5, which was synthesized using the disclosed C17 oxo alcohol LB A 32, is surprisingly less viscous than Target D2, which was synthesized using a linear alcohol, at KV100. Without wishing to be bound by theory, it is believed that an increase in branching index is associated with an increase in viscosity. Ostensibly, the disclosed C17 oxo alcohol LB A 32 exhibits a branching index of about 2.27, while the comparative alcohol Comparative 3 exhibits a branching index of about 0.42 (as shown in Table 4). However, the foregoing results demonstrate that the disclosed neopentanoic ester 66, 46 generated using the disclosed C17 oxo alcohol BLA 32 is less viscous than the comparative neopentanoic ester generated using the comparative alcohol. Accordingly, the disclosed LBA 32 provide downstream advantages when utilized to generate products (e.g., neopentanoic ester compositions 66,46).

Examples of Monoesters Generated using LBA 32

[00210] The following are example monoester compositions 86, 46 generated using the LBA 32 (e.g., C9 oxo alcohol, C13 oxo alcohol, C17 oxo alcohol) as described by the methods of FIGS. 2 and 5. For simplicity, each reaction shows one example structure (i.e., representative structure) for LB A 32 (e.g., C9 oxo alcohol, C13 oxo alcohol, C17 oxo alcohol) that may be used to generate the monoester compositions 86, 46. However, it should be noted that the structure of the disclosed C9 oxo alcohol, C13 oxo alcohol, C17 oxo alcohol below is meant to be exemplary. It should be noted that in some instances when a KV (KV) is measured close to the freezing point of a respective ester composition 46, the KV may increase rapidly and be a value that is undesirable for use in certain applications. Nonetheless, certain esters may have desirable KVs above the freezing point.

[00211] Target El is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., decanoic acid (1) chemical formula: C10H20O2; molecular weight: 172.27 g/mol) was reacted with the disclosed C13 oxo alcohol (2) (e.g., LBA 32; chemical formula: C13H28O; molecular weight: 200.37 g/mol). The example reaction scheme is shown below:

EDC.HCl (1.5 eq), DMAP (0.5 eq) DCM, RT, 16 h

Target El

[00212] Target El, 3 -methyldodecyl decanoate, was synthesized via Steglich esterification reaction by adding DMAP (3.55 g, 29.0 m mol), EDCHC1 (16.69 g, 87 m mol), and 3- methyldodecan-l-ol (LBA1300) (13.96 g, 69.7 m mol) at 0°C to a stirred solution of decanoic acid (10 g, 58.0 m mol) in DCM (250 ml). The reaction was stirred for 16 h at room temperature. Completion of reaction was monitored by TLC. After completion of reaction, reaction was diluted with ice cold water (300 mL), compound was extracted into DCM (1 x 300 mL). The aqueous layer was re-extracted with DCM (1 x 300 mL). The combined organic layer was washed with brine (200 mL), dried over Na2SOq, filtered, and concentrated under vacuum to afford crude as a colorless liquid. The crude was purified by column chromatography using Biotage isolera snap- 340g (230-400 silica gel) in 2-3% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 3 -methyldodecyl decanoate (12.0 g, 31.1 mmol, 65.7 % yield) as a colorless liquid. Viscosity properties for Target El are shown in Table 30. Characterization of Target El : Chemical Formula: C23H46O2. Molecular Weight: 354.62 g/mol.

Table 30 shows viscosity properties of Target El.

[00213] Target E2 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., decanoic acid (1) chemical formula: C10H20O2; molecular weight: 172.27 g/mol) was reacted with the disclosed C17 oxo alcohol (2)

(e.g., LBA 32; chemical formula: C17H36O; molecular weight: 256.47 g/mol). The example reaction scheme is shown below:

Target E2 [00214] Target E2 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 3 -methylhexadecyl decanoate (21.6 g, 48.4 mmol, 83 % yield) as a colorless liquid. Viscosity properties for Target E2 are shown in Table 31. Characterization of Target E2: Chemical Formula: C27H54O2. Molecular Weight: 410.41 g/mol. GCMS: m/z = 410.41 [M]⁺, RT (min):8.56-9.41 min, Area (%):98.58 %. 'H-NMR (400 MHz, CDC13): 54.09-3.92 (m, 2H), 2.30- 2.25 (m, 2H), 1.63-1.56 (m, 4H), 1.42-1.09 (m, 32H), 0.92-0.80 (m, 12H). | KV-20,001 | 155,74 | 137,7676 | 0,8846

Table 31 shows viscosity properties of Target E2.

[00215] Target E3 is an example of a comparative ester where precursor 42 (e.g., decanoic acid (1) chemical formula: C10H20O2; molecular weight: 172.27 g/mol) was reacted with a comparative alcohol (2) (e.g., Comparative 3, pentadecanol, chemical formula: C15H32O; molecular weight: 228.42 g/mol). The example reaction scheme is shown below:

Target E3

[00216] Target E3 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340 g (230-400 silica gel), in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get pentadecyl decanoate (23.2 g, 59.4 mmol, 91 % yield) as a colorless liquid. Viscosity properties for Target E3 are shown in Table 32. Characterization of Target E3 : Chemical Formula: C₂5H₅₀O2. Molecular Weight: 382.38 g/mol. GCMS: m/z = 382.38 [M]⁺, RT (min):8.001-8.91, Area (%): 99.12. 'H-NMR (400 MHz, CDC13): 54.04 (t, J= 6.8 Hz, 2H), 2.29- 2.24 (m, 2H), 1.61-1.56 (m, 4H), 1.41-1.24 (m, 46H), 0.9-0.81 (m, 10H).

Table 32 shows viscosity properties of Target E3.

[00217] Target E4 is an example of a comparative ester where precursor 42 (e.g., decanoic acid (1) chemical formula: C10H20O2; molecular weight: 172.27 g/mol) was reacted with a comparative alcohol (2) (e.g., Comparative 2, 4,6,9-trimethyldecan-l-ol, chemical formula: C13H28O; molecular weight: 200.21 g/mol). The example reaction scheme is shown below:

EDC. HCl (1.5eq) DMAP (0.5eq)

1 DCM, RT 16h

Target E4

[00218] Target E4 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions.

The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collected pure fractions of compound and concentrated to get 4,6,9-trimethyldecyl decanoate (23.5 g, 61.0 mmol, 90 % yield) as colorless liquid. Viscosity properties for Target E4 are shown in Table 33. Characterization of Target E4: Chemical Formula: C23H46O2. Molecular Weight: 354.35 g/mol. GCMS: m/z: 354.35 [M]⁺, RT (min): 7.53-8.34, Area (%): 99.65. 'H-NMR (400 MHz, CDC13): 5 4.06-4.04 (m, 2H), 2.30-2.26 (m, 2H), 1.63-1.58 (m, 4H), 1.42-1.13 (m, 20H), 0.91-0.73 (m, 16H).

Table 33 shows viscosity properties of Target E4.

[00219] Target E5 is an example of a comparative ester where precursor 42 (e.g., decanoic acid (1) chemical formula: C10H20O2; molecular weight: 172.27 g/mol) was reacted with a comparative alcohol (2) (e.g., 2-ethylhexan-l-ol, chemical formula: CsHisO; molecular weight: 130.14 g/mol). The example reaction scheme is shown below: Target E5

[00220] Target E5 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340 g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2-ethylhexyl decanoate (19.2 g, 64.6 m mol, 89 % yield) as a colorless liquid. Viscosity properties for Target E5 are shown in Table 34. Characterization of Target E5 : Chemical Formula: CisI . Molecular Weight: 284.27 g/mol. GCMS: m/z:284.27 [M]⁺, RT (min):6.952, Area (%): 99.10. 'H-NMR (400 MHz, CDC13): 5 3.98-3.95 (m, 2H), 2.27 (t, J= 7.60 Hz, 2H), 1.63-1.51 (m, 3H), 1.40-1.24 (m, 20H), 0.88-0.82 (s, 9H).

Table 34 shows viscosity properties of Target E5.

[00221] Target E6 is a comparative ester where precursor 42 (e.g., heptanoic acid (1) chemical formula: C7H14O2; molecular weight: 130.19 g/mol) was reacted with a comparative alcohol (2) (e.g., 2-methyl heptyl alcohol, chemical formula: CsHisO; molecular weight: 130.2 g/mol). The example reaction scheme is shown below:

DMAP (0.5 eq)

Target E6

[00222] Target E6 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get as a colorless liquid. Viscosity properties for Target E6 are shown in Table 35. Characterization of Target E6: Chemical Formula: CisEEeCE. Molecular Weight: 284.27 g/mol. GCMS: m/z:284.48 [M]⁺, RT (min): 7.003, Area (%):98.80. 'H-NMR (400 MHz, CDC13): 53.98- 3.84 (m, 2H), 2.32 (t, = 7.60 Hz, 2H), 1.79-1.76 (m, 1H), 1.67-1.62 (m, 2H), 1.40-1.30 (m, 18H), 1.28-1.15 (m, 1H), 0.94-0.92 (m, 9H).

Table 35 shows viscosity properties of Target E6.

[00223] Target E7 is an example of a comparative ester where precursor 42 (e.g., decanoic acid (1) chemical formula: C10H20O2; molecular weight: 172.27 g/mol) was reacted with a comparative alcohol (2) (e.g., dodecanol, chemical formula: C12H26O; molecular weight: 186.20 g/mol). The example reaction scheme is shown below:

EDC.HC1, (1.5 eq), DMAP (0.5 eq)

1 DCM, RT, 16h

Target E7

[00224] Target E7 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-3 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get dodecyl decanoate (22.4 g, 65.0 m mol, 93 % yield) as a colorless liquid. Viscosity properties for Target E7 are shown in Table 36. Characterization ofTargetE7: Chemical Formula: C22H44O2. Molecular Weight: 340.33 g/mol. GCMS: m/z: 340.5 [M]⁺, RT (min):8.108, Area(%): 98.80. ‘H-NMR (400 MHz, CDC13): 5 4.04 (t, J= 6.80 Hz, 2H), 2.27 (t, J= 7.60 Hz, 2H), 1.63-1.57 (m, 4H), 1.67-1.62 (m, 2H), 1.29-1.25 (m, 26H), 0.88-0.82 (m, 6H).

Table 36 shows viscosity properties of Target E7.

[00225] Target E8 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., dodecanoic acid (1) chemical formula: C12H24O2; molecular weight: 200.32 g/mol) was reacted with the disclosed C13 oxo alcohol (2) (e.g., LBA 32; chemical formula: C13H28O; molecular weight: 200.37 g/mol). The example reaction scheme is shown below:

EDC.HCl (1.5 eq), DMAP (0.5 eq) DCM, RT, 16 h

Target E8

[00226] Target E8 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get as 3 -methyldodecyl dodecanoate (14.0 g, 33.3 m mol, 74.9 % yield) as a colorless liquid. Viscosity properties for Target E8 are shown in Table 37. Characterization of Target E8: Chemical Formula: C25H50O2. Molecular Weight: 382.67 g/mol. GCMS: m/z: 382.67 [M]⁺, RT (min): 8.16-8.81, Area (%): 99.31. 'H-NMR (400 MHz, CDC13): 5 4.10-3.97 (m, 2H), 2.32-2.26 (m, 2H), 1.78-1.56 (m, 4H), 1.29-1.09 (m, 29H), 0.93-0.81 (m, 12H).

Table 37 shows viscosity properties of Target E8. [00227] Target E9 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., dodecanoic acid (1) chemical formula: C12H24O2; molecular weight: 200.32 g/mol) was reacted with the disclosed C17 oxo alcohol (2) (e.g., LBA 32; chemical formula: C17H36O; molecular weight: 256.47 g/mol). The example reaction scheme is shown below:

Target E9

[00228] Target E9 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 1-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 3 -methylhexadecyl dodecanoate (23.0 g, 47.2 m mol, 86 % yield) as a colorless liquid. Viscosity properties for Target E9 are shown in Table 38. Characterization of Target E7: Chemical Formula: C29H58O2. Molecular Weight: 438.44 g/mol. GCMS: m/z: 438.4 [M]⁺, RT (min):9.09-10.78, Area (%): 99.92. 'H-NMR (400 MHz, CDC13): 5 4.10-3.85 (m, 2H), 2.31-2.26 (m, 2H), 1.81-1.56 (m, 4H), 1.43-1.09 (m, 36H), 0.92-0.81 (m, 13H).

Table 38 shows viscosity properties of Target E9.

[00229] Target E10 is an example of a comparative ester where precursor 42 (e.g., dodecanoic acid (1) chemical formula: C12H24O2; molecular weight: 200.18 g/mol) was reacted with a comparative alcohol (2) (e.g., Comparative 3, pentadecanol, chemical formula: C15H32O; molecular weight: 228.42 g/mol). The example reaction scheme is shown below:

Target E10

[00230] Target E10 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 1-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get pentadecyl dodecanoate (22.8 g, 50.5 m mol, 85% yield) as a white wax. Characterization of Target E10: Chemical Formula: C27H54O2. Molecular Weight: 410.41 g/mol. GCMS: m/z: 438.4 [M]⁺, RT (min):8.37-9.74, Area (%): 99.40.¹H-NMR (400 MHz, CDC13): 5 4.05 (t, J= 6.40 Hz, 2H), 2.29-2.26 (m, 2H), 1.62-1.59 (m, 5H), 1.29-1.26 (m, 52H), 0.92-0.85 (m, 10H).

[00231] Target Ell is an example of a comparative ester where precursor 42 (e.g., dodecanoic acid (1) chemical formula: C12H24O2; molecular weight: 200.18 g/mol) was reacted with a comparative alcohol (2) (e.g., Comparative 2, 4,6,9-trimethyldecan-l-ol, chemical formula: C13H28O; molecular weight: 200.21 g/mol). The example reaction scheme is shown below:

Target El l

[00232] Target El 1 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-3 % ethyl acetate in pet ether to collected pure fractions of compound and concentrated to get 4,6,9-trimethyldecyl dodecanoate (20.5 g, 49.3 m mol, 89% yield) as a colorless liquid. Viscosity properties for Target El l are shown in Table 39. Characterization of Target El l : Chemical Formula: C25H50O2. Molecular Weight: 382.38 g/mol. GCMS: m/z: 382.5 [M]⁺, RT (min) 8.09-8.90, Area (%): 99.13. ‘H-NMR (400 MHz, CDC13): 5 4.07-4.03 (m, 2H), 2.28-2.24 (m, 2H), 1.61-1.58 (m, 5H), 1.28-1.06 (m, 30H), 0.88-0.72 (m, 16H).

Table 39 shows viscosity properties of Target El l.

[00233] Target E12 is an example of a comparative ester where precursor 42 (e.g., dodecanoic acid (1) chemical formula: C12H24O2; molecular weight: 200.18 g/mol) was reacted with a comparative alcohol (2) (e.g., 2-ethylhexan-l-ol, chemical formula: CsHisO; molecular weight:

130.14 g/mol). The example reaction scheme is shown below:

DCM, RT 16h

Target E12 [00234] Target E12 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 1-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2-ethylhexyl dodecanoate (19.0 g, 59.9 m mol, 95 % yield) as a colorless liquid. Viscosity properties for Target E12 are shown in Table 40. Characterization of Target E12: Chemical Formula: C20H40O2. Molecular Weight: 312.30 g/mol. GCMS: m/z: 312.30 [M]⁺, RT (min):7.45, Area (%): 98.66. 'H-NMR (400 MHz, CDC13): 5 3.99-3.91 (m, 2H), 2.26 (t, J= 7.20 Hz, 2H), 1.60-1.50 (m, 3H), 1.39-1.23 (m, 24H), 0.87-0.81 (m, 9H).

Table 40 shows viscosity properties of Target E12.

[00235] Target E13 is an example of a comparative ester where precursor 42 (e.g., dodecanoic acid (1) chemical formula: C12H24O2; molecular weight: 200.18 g/mol) was reacted with a comparative alcohol (2) (e.g., 2-m ethyl heptyl alcohol, chemical formula: CsHisO; molecular weight: 130.2 g/mol). The example reaction scheme is shown below: DMAP (0.5 eq) DCM, RT

Target El 3

[00236] Target El 3 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2-methylheptyl dodecanoate (10.1 g, 32.0 mmol, 92 % yield) as a colorless liquid. Viscosity properties for Target El 3 are shown in Table 41. Characterization of Target El 3:

Chemical Formula: C20H40O2. Molecular Weight: 312.54 g/mol. GCMS: m/z: 312.20 [M]⁺, R_f 7.486, Area (%): 98.98. 'H-NMR (400 MHz, CDC13): 5 3.98-3.84 (m, 2H), 2.31 (t, J= 7.60 Hz, 2H), 1.80-1.75 (m, 1H), 1.69-1.61 (m, 2H), 1.44-1.27 (m, 23H), 1.18-1.13 (m, 1H), 0.93-0.86 (m, 9H).

Table 41 shows viscosity properties of Target E13.

[00237] Target E14 is an example of a comparative ester where precursor 42 (e.g., dodecanoic acid (1) chemical formula: C12H24O2; molecular weight: 200.18 g/mol) was reacted with a comparative alcohol (2) (e.g., lauryl alcohol (1) chemical formula: C12H26O; molecular weight: 186.20 g/mol). The example reaction scheme is shown below:

Target El 4

[00238] Target E14 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 1-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get dodecyl dodecanoate (21.8 g, 57.9 m mol, 95 % yield) as white wax. Characterization of Target E14: Chemical Formula: C24H48O2. Molecular Weight: 368.37 g/mol. GCMS: m/z: 368.4a0 [M]⁺, RT (min) 8.651, Area (%):97.94. ’H-NMR (400 MHz, CDC13): 5 4.08 (t, J= 6.80 Hz, 2H), 2.31 (t, J= 7.60 Hz, 2H), 1.65-1.60 (m, 4H), 1.32-1.28 (m, 34H), 0.90 (t, J = 7.20 Hz, 6H).

[00239] Target E15 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., stearic acid (1) chemical formula: C18H36O2; molecular weight: 284.27 g/mol) was reacted with the disclosed C13 oxo alcohol (2) (e.g., LBA 32; chemical formula: C13H28O; molecular weight: 200.37 g/mol). The example reaction scheme is shown below: "OH DCM, RT 16h

Target El 5

[00240] Target El 5 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collected pure fractions of compound and concentrated to get 3 -methyldodecyl stearate (19.5 g, 35.5 m mol, 81 % yield) as a colorless liquid. Viscosity properties for Target El 5 are shown in Table 42. Characterization of Target El 5: Chemical Formula: C31H62O2. Molecular Weight: 466.47 g/mol. GCMS: m/z: 466.47 [M]⁺, RT (min): 8.33-9.46, Area (%):97.94. ¹H-NMR (400 MHz, CDC13): 5 4.10-3.96 (m, 2H), 2.31-2.26 (m, 2H), 1.63-1.57 (m, 4H), 1.43-1.09 (m, 41H), 0.93-0.81 (m, 13H).

Table 42 shows viscosity properties of Target E15.

[00241] Target E16 is an example of an ester that may be part of the ester composition 46. The ester may be formed by a reaction where precursor 42 (e.g., stearic acid (1) chemical formula: C18H36O2; molecular weight: 284.27 g/mol) was reacted with the disclosed C17 oxo alcohol (2) (e.g., LBA 32; chemical formula: C17H36O; molecular weight: 256.47 g/mol). The example reaction scheme is shown below:

Target El 6

[00242] Target El 6 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 3 -methylhexadecyl stearate (21.4 g, 37.6 m mol, 89 % yield) as a colorless liquid. Viscosity properties for Target E16 are shown in Table 43. Characterization of Target E16: Chemical Formula: C35H70O2. Molecular Weight: 522.54 g/mol. GCMS: m/z: 522.54 [M]⁺, RT (min): 7.50-10.18, Area (%): 99.34.¹H-NMR (400 MHz, CDC13): 5 4.11-3.95 (m, 2H), 2.32-2.27 (m, 2H), 1.70-1.57 (m, 4H), 1.44-1.11 (m, 50H), 0.94-0.83 (m, 13H).

Table 43 shows viscosity properties of Target E16.

[00243] Target E17 is an example of a comparative ester where precursor 42 (e.g., stearic acid (1) chemical formula: CisHseCE; molecular weight: 284.27 g/mol) was reacted with a comparative alcohol (2) (e.g., Comparative 3, pentadecanol, chemical formula: C15H32O; molecular weight: 228.42 g/mol). The example reaction scheme is shown below:

Target El 7

[00244] Target El 7 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get pentadecyl stearate (21.3 g, 39.6 m mol, 91 % yield) as a white wax. Characterization of Target E17: Chemical Formula: C33H66O2. Molecular Weight: 494.51 g/mol. GCMS: m/z: 494.60 [M]⁺, RT (min): 8.84-11.94, Area (%): 99.23. 'H-NMR (400 MHz, CDC13): 5 4.11-3.95 (m, 2H), 2.32-2.27 (m, 2H), 1.70-1.57 (m, 4H), 1.44-1.11 (m, 50H), 0.94-0.83 (m, 13H). [00245] Target E18 is an example of a comparative ester where precursor 42 (e.g., stearic acid (1) chemical formula: CisHaeCh; molecular weight: 284.27 g/mol) was reacted with a comparative alcohol (2) (e.g., Comparative 2, 4,6,9-trimethyldecan-l-ol, chemical formula: C13H28O; molecular weight: 200.21 g/mol). The example reaction scheme is shown below:

Target El 8

[00246] Target El 8 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-3 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 4,6,9-trimethyldecyl stearate (20.6 g, 40.9 m mol, 93 % yield) as a colorless liquid. Viscosity properties for Target El 8 are shown in Table 44. Characterization of Target El 8: Chemical Formula: C31H62O2. Molecular Weight: 466.47 g/mol. GCMS: m/z: 466.50 [M]⁺, RT (min):8.03-10.06, Area (%): 99.40. 'H-NMR (400 MHz, CDC13): 5 4.07 (t, J = 6.80 Hz, 2H), 2.32-2.29 (m, 3H), 1.65-1.60 (m, 5H), 1.37-1.28 (m, 66H), 0.93-0.88 (m, 6H).

Table 44 shows viscosity properties of Target El 8.

[00247] Target E19 is an example of a comparative ester where precursor 42 (e.g., stearic acid (1) chemical formula: C18H36O2; molecular weight: 284.27 g/mol) was reacted with a comparative alcohol (2) (e.g., 2-ethyl hexyl alcohol; chemical formula: CsHisO; molecular weight: 130.14 g/mol). The example reaction scheme is shown below:

Target El 9

[00248] Target El 9 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-3 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2-ethylhexyl stearate (16.4 g, 40.0 m mol, 92 % yield) as a colorless liquid. Viscosity properties for Target E19 are shown in Table 45. Characterization of Target E19: Chemical Formula: C26H52O2. Molecular Weight: 396.40 g/mol. GCMS: m/z: 396.40 [M]⁺, RT (min): 7.059, Area (%):96.74. 'H-NMR (400 MHz, CDC13): 54.07 (t, J= 6.80 Hz, 2H), 2.32-2.29 (m, 3H), 1.65-1.60 (m, 5H), 1.37-1.28 (m, 66H), 0.93-0.88 (m, 6H).

Table 45 shows viscosity properties of Target E19.

[00249] Target E20 is an example of a comparative ester where precursor 42 (e.g., stearic acid (1) chemical formula: CisHieCE; molecular weight: 284.27 g/mol) was reacted with a comparative alcohol (2) (e.g., 2-methyl heptyl alcohol; chemical formula: CsHisO; molecular weight: 130.23 g/mol). The example reaction scheme is shown below: DMAP (0.5 eq) DCM, RT Target E20

[00250] Target E20 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 1-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2-methylheptyl stearate (10.6 g, 25.9 m mol, 92 % yield) as a colorless liquid. Viscosity properties for Target E20 are shown in Table 46. Characterization of Target E20: Chemical Formula: C26H52O2. Molecular Weight: 396.70 g/mol. GCMS: m/z: 396.5 [M]⁺, RT (min): 9.084, Area (%): 96.88. 'H-NMR (400 MHz, CDC13): 5 3.98-3.84 (m, 2H), 2.31 (t, J = 7.60 Hz, 2H), 1.78-1.70 (m, 1H), 1.65-1.61 (m, 2H), 1.40-1.24 (m, 36H), 0.94-0.90 (m, 10H).

Table 46 shows viscosity properties of Target E20.

[00251] Target E21 is an example of a comparative ester where precursor 42 (e.g., stearic acid (1) chemical formula: CisHseCE; molecular weight: 284.27 g/mol) was reacted with a comparative alcohol (2) (e.g., lauryl alcohol; chemical formula: C12H26O; molecular weight: 186.20 g/mol). The example reaction scheme is shown below:

Target E21

[00252] Target E21 was synthesized via a Steglich esterification reaction following generally similar synthesis and purification conditions as Target El with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, temperature, and/or reaction conditions. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 0-2 % ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get dodecyl stearate (21.7 g, 47.0 m mol, 97 % yield) as a white wax. Characterization of Target E21 : Chemical Formula: C30H60O2. Molecular Weight: 452.46 g/mol. GCMS: m/z: 452.40 [M]⁺, RT (min): 11.44, Area (%): 98.05. ‘H-NMR (400 MHz, CDC13): 5 4.07 (t, J= 6.40 Hz, 2H), 2.30 (t, J= 7.60 Hz, 2H), 1.65-1.59 (m, 4H), 1.32-1.27 (m, 46H), 0.91- 0.88 (m, 6H). [00253] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about 40°C ranging from about 0.1 mm²/s to about 20 mm²/s, about 1 to about 18 mm²/s, about 2 to 15 about mm²/s, about 3 to about 10 mm²/s, about 4 to about 9 mm²/s, about 5 to 8 mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, about 15, about 16, about 17, about 18, about 19, or about 20 mm²/s. monoesters 86,46 may exhibit a DV at about 40°C ranging from about 0.1 mPa-s to about 20 mPa-s, about 1 to 18 mPa-s, about 2 to 15 mPa-s, about 3 to 10 mPa-s, about 4 to 9 mPa-s, about 5 to 8 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about

12, about 13, about 14, about 15, about 16, about 17, about 18, about 19, or about 20 mPa-s. The monoesters 86,46 may exhibit a density at about 40°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00254] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about 100°C ranging from about 0.1 mm²/s to about 15 mm²/s, about 1 to about 12 mm²/s, about 1 to 11 about mm²/s, about 1 to about 10 mm²/s, about 1 to about 8 mm²/s, about 1 to 5 mm²/s, about 1 to 3 mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about

13, about 14, or about 15 mm²/s. The monoesters 86,46 may exhibit a DV at about 100°C ranging from about 0.1 mPa-s to about 15 mPa-s, about 1 to 13 mPa-s, about 1 to 11 mPa-s, about 1 to 10 mPa-s, about 1 to 8 mPa-s, about 1 to 5 mPa-s, about 1 to 3 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mPa-s. The monoesters 86,46 may exhibit a density at about 100°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00255] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about 0°C ranging from about 0.1 mm²/s to about 40 mm²/s, about 5 to about 35 mm²/s, about 10 to 30 about mm²/s, about 15 to about 35 mm²/s, about 25 to about 40 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mm²/s. The monoesters 86,46 may exhibit a DV at about 0°C ranging from about 0.1 mPa-s to about 40 mPa-s, about 5 to about 35 mPa-s, about 10 to 30 about mPa-s, about 15 to about 35 mPa-s, about 20 to about 40 mPa-s such as about 0.1, about 1, about 10, about 20, about 30, about 40, or about 50 mPa-s. The monoesters 86,46 may exhibit a density at about 0°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00256] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about -10°C ranging from about 0.1 mm²/s to about 70 mm²/s, about 5 to about 45 mm²/s, about 10 to 40 about mm²/s, about 15 to about 35 mm²/s, about 45 to about 70 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, or about 70 mm²/s. The monoesters 86,46 may exhibit a DV at about -10°C ranging from about 0.1 mPa-s to about 70 mPa-s, about 5 to about 45 mPa-s, about 10 to 40 about mPa-s, about 15 to about 35 mPa-s, about 45 to about 70 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, or about 70 mPa-s. The monoesters 86,46 may exhibit a density at about -10°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00257] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about -20°C ranging from about 0.1 mm²/s to about 150 mm²/s, about 10 to about 125 mm²/s, about 20 to 100 about mm²/s, about 30 to about 75 mm²/s, about 40 to about 100 mm²/s, about 70 to about 140 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, or about 200 mm²/s. The monoesters 86,46 may exhibit a DV at about -20°C ranging from about 0.1 mPa-s to about 150 mPa-s, about 10 to about 125 mPa-s, about 20 to 100 about mPa-s, about 30 to about 75 mPa-s, about 40 to about 100 mPa-s, about 50 to 75 mPa-s, about 70 to about 140 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, or about 200 mPa-s. The monoesters 86,46 may exhibit a density at about -20°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00258] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C13 oxo alcohol) may exhibit a KV at about -35°C ranging from about 0.1 mm²/s to about 450 mm²/s, about 10 to about 375 mm²/s, about 225 to about 425 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, about 200, or about 225, about 250, about 275, about 300, about 325, about 350, about 375, about 400, about 425, or about 450 mm²/s. The monoesters 86,46 may exhibit a DV at about -35°C ranging from about 0.1 mPa-s to about 450 mPa-s, about 10 to about 375 mPa-s, about 225 to about 375 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, about 200, or about 225, about 250, about 275, about 300, about 325, about 350, about 375, about 400, about 425, or about 450 mPa-s. The monoesters 86,46 may exhibit a density at about -35°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00259] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may exhibit a KV at about 40°C ranging from about 0.1 mm²/s to about 20 mm²/s, about 1 to about 18 mm²/s, about 2 to 15 about mm²/s, about 5 to 12 mm²/s, about 8 to about 12 mm²/s, about 10 to 12 mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, about 15, about 16, about 17, about 18, about 19, or about 20 mm²/s. monoesters 86,46 may exhibit a DV at about 40°C ranging from about 0.1 mPa-s to about 20 mPa-s, about 1 to 18 mPa-s, about 2 to 15 mPa-s, about 5 to 12 mPa-s, about 8 to 12 mPa-s, about 8 to 11 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, about 15, about 16, about 17, about 18, about 19, or about 20 mPa-s. The monoesters 86,46 may exhibit a density at about 40°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00260] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may exhibit a KV at about 100°C ranging from about 0.1 mm²/s to about 15 mm²/s, about 1 to about 12 mm²/s, about 2 to 11 about mm²/s, about 3 to about 10 mm²/s, about 4 to about 9 mm²/s, about 1 to 4 mm²/s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mm²/s. The monoesters 86,46 may exhibit a DV at about 100°C ranging from about 0.1 mPa-s to about 15 mPa-s, about 1 to 13 mPa-s, about 2 to 11 mPa-s, about 3 to 10 mPa-s, about 4 to 9 mPa-s, about 1 to 4 mPa-s, such as about 0.1, about 1, about 2, about 3, about 4, about 5, about 6, about 7, about 8, about 9, about 10, about 11, about 12, about 13, about 14, or about 15 mPa-s. The monoesters 86,46 may exhibit a density at about 100°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00261] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may exhibit a KV at about 0°C ranging from about 0.1 mm²/s to about 70 mm²/s, about 5 to about 65 mm²/s, about 10 to 55 about mm²/s, about 15 to about 45 mm²/s, about 20 to about 35 mm²/s, about 40 to about 65 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, or about 70 mm²/s. The monoesters 86,46 may exhibit a DV at about 0°C ranging from about 0.1 mPa-s to about 70 mPa-s, about 5 to about 65 mPa-s, about 10 to 55 about mPa-s, about 15 to about 45 mPa-s, about 20 to about 35 mPa-s, about 40 to about 60 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, or about 70 mPa-s. The monoesters 86,46 may exhibit a density at about 0°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00262] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may exhibit a KV at about -10°C ranging from about 0.1 mm²/s to about 120 mm²/s, about 5 to about 110 mm²/s, about 10 to about 100 mm²/s, about 15 to about 90 mm²/s, about 75 to about 115 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, or about 120 mm²/s. The monoesters 86,46 may exhibit a DV at about -10°C ranging from about 0.1 mPa-s to about 120 mPa-s, about 5 to about 110 mPa-s, about 10 to about 100 mPa-s, about 15 to about 90 mPa-s, about 65 to about 100 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, or about 120 mPa-s. The monoesters 86,46 may exhibit a density at about -10°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00263] In an embodiment, the monoesters 86,46 generated using the disclosed LBA 32 (e.g., C17 oxo alcohol) may exhibit a KV at about -20°C ranging from about 0.1 mm²/s to about 300 mm²/s, about 25 to about 275 mm²/s, about 50 to 250 about mm²/s, about 75 to about 225 mm²/s, about 100 to about 200 mm²/s, about 125 to 175 mm²/s, about 150 to about 290 mm²/s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, about 200, about 210, about 220, about 230, about 240, about 250, about 260, about 270, about 280, about 290, or about 300 mm²/s. The monoesters 86,46 may exhibit a DV at about -20°C ranging from about 0.1 mPa-s to about 300 mPa-s, about 25 to about 275 mPa-s, about 50 to 250 about mPa-s, about 75 to about 225 mPa-s, about 100 to about 200 mPa-s, about 125 to 175 mPa-s, about 150 to about 290 mPa-s, about 130 to about 260 mPa-s, such as about 0.1, about 1, about 10, about 20, about 30, about 40, about 50, about 60, about 70, about 80, about 90, about 100, about 110, about 120, about 130, about 140, about 150, about 160, about 170, about 180, about 190, about 200, about 210, about 220, about 230, about 240, about 250, about 260, about 270, about 280, about 290, or about 300 mPa-s. The monoesters 86,46 may exhibit a density at about -20°C ranging from about 0.7 g/cm³ to about 1.00 g/cm³, such as about 0.75 to about 0.95, about 0.80 to about 0.98, about 0.80 to about 0.90, such as about 0.70, about 0.72, about 0.74, about 0.76, about 0.78, about 0.80, about 0.82, about 0.84, about 0.86, about 0.88, about 0.90, about 0.92, about 0.94, about 0.96, about 0.98, or about 1 g/cm³.

[00264] In general, the disclosed monoester compositions 86, 46 exhibit several advantages over the comparative monoesters. Surprisingly, the comparative esters (e.g., Target E4/Target El l/Target El 8), which were generated using a highly branched alcohol (e.g., Comparative 3), exhibit greater viscosities at KV40 and KV100 than the disclosed monoester compositions 86,46 (e.g., Target El/Target E8/Target El 5), which were generated using the disclosed LB A 32 (e.g., C13 oxo alcohol), even though both the disclosed LBA 32 and comparative alcohol (e.g., Comparative 3) exhibit a generally similar average carbon number. Additionally, the disclosed monoester compositions 86,46, Target El are surprisingly less viscous (e.g., KV40, KV100) than the comparative monoester (e.g., Target E3), which was synthesized using a linear comparative alcohol. Accordingly, these results demonstrate that the disclosed LBA 32 provides several advantages downstream when utilized to generate monoester compositions 86, 46 for lubricant formulations.

Examples of Comparative Esters Generated using Comparative 1 (C9 alcohol)

[00265] The following are example comparative esters generated using Comparative 1 of Table 1 (e.g., C9 alcohol).

[00266] Target Fl is an example of a comparative ester where precursor 42 (e.g., phthalic acid (1), Chemical Formula: C9H20O; Molecular Weight: 144.26 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below:

Target Fl

[00267] Target Fl was synthesized via a Steglich esterification reaction. To a stirred solution of phthalic acid (8 g, 48.2 mmol) in DCM (160 mL), 2,4-dimethylheptan-l-ol (Comparative 1) (15.28 g, 106 mmol), DMAP (5.88 g, 48.2 mmol) and followed by EDC.HC1 (27.7 g, 144 mmol) were added at 0°C. The resulting mixture was stirred at room temperature for 16 h. The completion of the reaction was monitored by TLC. After confirmation, the reaction mixture was diluted with ice cold water (500 mL) and extracted into DCM (2 x 200 mL). The aqueous layer was re-extracted with DCM (2 x 200 mL). The combined organic layer was washed with brine (500 mL), dried over Na2SO4, filtered and concentrated under vacuum to afford 23.8 g of crude as yellow liquid. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether. Pure product fractions were collected and concentrated to get bis(2,4-dimethylheptyl) phthalate (17.8 g, 42.1 mmol, 87 % yield) as colorless liquid. Viscosity properties of Target Fl are shown in Table 47. Characterization of Target Fl : Chemical Formula: C26H42O4; Molecular Weight: 418.62 g/mol. LCMS: m\z: 419.4 (M+H), RT (min): 2.700 to 2.752, Area (%): 96.4. GCMS: m\z: 418.4 (M) +, RT (min): 9.128 to 10.241, Area (%): 97.4. HPLC: RT (min): 4.155 to 4.443, Area (%): 99.7. 1H-NMR (400 MHz, CDC13): 5 7.75-7.73 (m, 2H), 7.56-7.53 (m, 2H), 4.37-4.30 (m, 4H), 1.76-1.73 (m, 4H), 1.20-1.39 (m, 12H), 0.81-0.94 (m, 18H)

Table 47 shows viscosity properties of Target Fl.

[00268] Target F2 is an example of a comparative ester where precursor 42 (e.g., terephthalic acid (1), chemical formula: CsHeCL, Molecular Weight: 166.13 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below:

[00269] Target F2 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether. Pure product fractions were collected and concentrated to get bis(2,4-dimethylheptyl) terephthalate (12.9 g, 30.5 mmol, 84 % yield) as colorless liquid. Viscosity properties of Target F2 are shown in Table 48. Characterization of Target F2: Chemical Formula: C26H42O4, Molecular weight: 418.62 g/mol. LCMS: m\z: 419.4 (M+H), RT (min): 3.835 to 3.908, Area (%): 99.9. GCMS: m\z: 418.4 (M) +, RT (min): 9.307 to 11.174, Area (%): 99.6. HPLC: RT (min): 4.369 to 4.496, Area (%): 97.69/ 1H-NMR (400 MHz, CDC13): 5 8.12 (d, J = 1.60 Hz, 4H), 4.40-4.34 (m, 4H), 1.38-1.34 (m, 3H), 1.22-1.31 (m, 13H), 0.83-0.96 (m, 18H).

Table 48 shows viscosity properties of Target F2.

[00270] Target F3 is an example of a comparative ester where precursor 42 (e.g., adipic acid (1), Chemical Formula: C6H20O4; Molecular Weight: 146.14 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below: Target F3

[00271] Target F3 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), eluted with 2% ethyl acetate in pet ether to collect the pure fractions of compound, and concentrated to get bis(2,4-dimethylheptyl) adipate (14.8 g, 36.8 mmol, 90 % yield) as colorless liquid. Viscosity properties of Target F3 are shown in Table 49. Characterization of Target F3: Chemical Formula: C24H46O4, Molecular weight: 398.63 g/mol. LCMS: m\z: 399.3 (M+H), RT (min): 3.567 to 3.853, Area (%): 99.4. GCMS: m\z: 398.6 (M) ⁺, RT (min): 8.412 to 9.171, Area (%): 99.8. HPLC: RT (min): 4.189 to 4.490, Area (%): 99.6. 'H- NMR (400 MHz, CDCI3): 5 4.10-4.05 (m, 2H), 2.33-2.32 (m, 4H), 1.70-1.60 (m. 8H), 1.35-1.11 (m, 12H), 0.92-0.76 (m, 18H).

Table 49 shows viscosity properties of Target F3.

[00272] Target F4 is an example of comparative ester where precursor 42 (e.g., glutaric acid (1), Chemical Formula: CsHsC ; Molecular Weight: 132.12 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below:

Target F4

[00273] Target F4 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), eluted with 2% ethyl acetate in pet ether to collect pure fractions of compound, and concentrated to get bis(2,4-dimethylheptyl) glutarate (17.1 g, 44.0 mmol, 97 % yield) as colorless liquid. Viscosity properties of Target F4 are shown in Table 50. Characterization of Target F4: Chemical Formula: C23H44O4. Molecular Weight: 384.60 g/mol. LCMS: m\z: 385.4 (M+H), RT (min): 2.656 to 2.740, Area (%): 99.8. GCMS: m\z: 383.1 (M) +, RT (min): 8.231 to 9.028, Area (%): 98.5. HPLC: RT (min): 4.044 to 4.353, Area (%): 99.76. 1H- NMR (400 MHz, CDC13): 5 4.11-4.07 (m, 4H), 2.40-2.37 (m, 4H), 1.99-1.95 (m, 2H), 1.60 (m,

4H), 1.18-1.33 (m, 12H), 0.79-0.90 (m, 18H). Table 50 shows viscosity properties of Target F4.

[00274] Target F5 is an example of comparative ester where precursor 42 (e.g., succinic acid (1), Chemical Formula: C4H6O4; Molecular Weight: 118.09 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below: Target F5

[00275] Target F5 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel), eluted with 3% ethyl acetate in pet ether to collect pure fractions of compound, and concentrated to get bis(2,4-dimethylheptyl) succinate (15.8 g, 42.6 mmol, 84 % yield) as colorless liquid. Viscosity properties of Target F5 are shown in Table 51. Characterization of Target F5: Chemical Formula: C22H42O4. Molecular Weight: 370.57 g/mol. LCMS: m\z: 371.4 (M+H), RT (min): 2.600 to 2.638, Area (%): 99.8. GCMS: RT (min): 7.990 to 8.652, Area (%): 99.7. HPLC: RT (min): 3.912 to 4.086, Area (%): 98.8. 1H-NMR (400 MHz, CDC13): 5 4.15-4.09 (m, 4H), 2.64 (s, 4H), 1.66-1.61 (m, 4H), 1.16-1.34 (m, 12H), 0.79-0.90 (m, 18H).

Table 51 shows viscosity properties of Target F5.

[00276] Target F6 is an example of a comparative ester where precursor 42 (e.g., benzoic acid (1), Chemical formula: C7H6O2; Molecular weight: 122.12 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below:

Target F6

[00277] Target F6 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2,4-dimethylheptyl benzoate (14.2 g, 56.6 mmol, 86 % yield) as pale yellow liquid. Viscosity properties of Target F6 are shown in Table 52. Characterization of Target F6: Chemical Formula: C16H24O2. Molecular Weight: 248.37 g/mol. LCMS: Not detected. GCMS: m\z: 248.1 (M) +, RT (min): 6.502 to 7.097, Area (%): 99.61. HPLC: RT (min): 2.784 to 3.050, Area (%): 99.1. 1H-NMR (400 MHz, CDC13): 5 8.07-8.05 (m, 2H), 8.59-8.55 (m, 1H), 8.48-8.44 (m, 2H), 4.38-4.32 (m, 2H), 1.58-1.19 (m, 8H), 0.98-0.81 (m, 9H).

Table 52 shows viscosity properties of Target F6. [00278] Target F7 is an example of a comparative ester where precursor 42 (e.g., 3- phenylpropanoic acid (1); Chemical Formula: C9H10O2; Molecular Weight: 150.18 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below: Target F7

[00279] Target F7 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2,4-dimethylheptyl 3-phenylpropanoate (16.5 g, 59.1 mmol, 89 % yield) as colorless liquid. Viscosity properties of Target F7 are shown in Table 53. Characterization of Target F7: Chemical Formula: CisFhsCh. Molecular Weight: 276.42 g/mol. LCMS: m\z: 277.4 (M+H), RT (min): 3.308 to 3.376, Area (%): 99.9. GCMS: m\z: 276.2 (M) +, RT (min): 7.086 to 7.604, Area (%): 99.7. HPLC: RT (min): 2.977 to 3.215, Area (%): 99.93. 1H-NMR (400 MHz, CDC13): : 5 7.34-7.31 (m, 2H), 7.25-7.22 (m, 3H), 4.15-4.09 (m, 2H), 3.02-2.98 (m, 2H), 2.69- 2.64 (m, 2H), 1.65-1.62 (m, 2H), 1.38-1.15 (m, 6H), 0.83-0.93 (m, 9H).

Table 53 shows viscosity properties of Target F7.

[00280] Target F8 is an example of a comparative ester where precursor 42 (e.g., pivalic acid (1), chemical formula: C5H10O2; molecular weight: 102.13 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below:

Target F8 [00281] Target F8 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect the pure fractions of compound and concentrated to get 2,4-dimethylheptyl pivalate (13.1 g, 56.8 mmol, 83 % yield) as colorless liquid. Viscosity properties of Target F8 are shown in Table 54. Characterization of Target F8: Chemical Formula: C14H28O2. Molecular Weight: 228.38 g/mol. LCMS: Not Detected. GCMS: RT (min): 5.006 to 5.808, Area (%): 97.8. HPLC: Not Detected. 1H-NMR (400 MHz, CDC13): 5 4.07-4.06 (m, 2H), 1.60-1.34 (m, 1H), 1.33-1.22 (m, 17H), 0.93-0.80 (m, 8H).

Table 54 shows viscosity properties of Target F8.

[00282] Target F9 is an example of a comparative ester where precursor 42 (e.g., decanoic acid (1), chemical formula: C10H20O2; molecular weight 172.27 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below:

Target F9

[00283] Target F9 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2,4-dimethylheptyl decanoate (14.8 g, 49.1 mmol, 85 % yield) as colorless liquid. Viscosity properties of Target F9 are shown in Table 55. Characterization of Target F9: Chemical Formula: C19H38O2. Molecular Weight: 298.51 g/mol. LCMS: RT (min): 3.752 to 3.842, Area (%): 99.9. GCMS: m\z: 298.2 (M) +, RT (min): 6.989 to 7.59, Area (%): 99.4. HPLC: RT (min): 4.161 to 4.317, Area (%): 99.8. 1H-NMR (400 MHz, CDC13): 5 4.11-4.07 (m, 2H), 2.33- 2.29 (m, 2H), 1.67-1.59 (m, 4H), 1.36-1.16 (m, 18H), 0.93-0.78 (m, 12H).

Table 55 shows viscosity properties of Target F9.

[00284] Target F10 is an example a comparative ester where precursor 42 (e.g., dodecanoic acid (1), chemical formula: C12H24O2, molecular weight: 200.32 g/mol) was reacted with Comparative 1 (2). The example reaction scheme is shown below:

Target F 10

[00285] Target F10 was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2,4-dimethylheptyl dodecanoate (15.2 g, 46.5 mmol, 93 % yield) as colorless liquid. Viscosity properties of Target F10 are shown in Table 56. Characterization of Target F10: Chemical Formula: C21H42O2. Molecular Weight: 326.57 g/mol. LCMS: RT (min): 3.752 to 3.842, Area (%): 99.9. GCMS: RT (min): 6.989 to 7.590, Area (%): 99.4.HPLC: RT (min): 4.161 to 4.317, Area (%): 99.7. 1H-NMR (400 MHz, CDC13): 5 4.11-4.07 (m, 2H), 2.33-2.29 (m, 2H), 1.67-1.59 (m, 4H), 1.36-1.28 (m, 20H), 1.18-0.92 (m, 2H), 0.90-0.78 (m, 12H).

Table 56 shows viscosity properties of Target F10.

[00286] Target Fll is an example of a comparative ester where precursor 42 (e.g., stearic acid (1), chemical formula CisHseCh, molecular weight 284.48 g/mol) was reacted with Comparative

1 (2). The example reaction scheme is shown below:

Target Fl l

[00287] Target Fl l was synthesized via a Steglich esterification reaction following generally similar synthesis as Target Fl with modifications to the relative amounts (e.g., equivalents (eq)) of one or more reagents, types of reagents, and/or reaction conditions as shown in the reaction scheme. The crude was purified by column chromatography using Biotage isolera snap-340g (230-400 silica gel) in 2% ethyl acetate in pet ether to collect pure fractions of compound and concentrated to get 2,4-dimethylheptyl stearate (15.8 g, 38.1 mmol, 90 % yield) as colorless liquid colorless liquid. Viscosity properties of Target Fl l are shown in Table 57. Characterization of TargetFl l : Chemical Formula: C27H54O2. Molecular Weight: 410.73 g/mol. LCMS: Not detected. GCMS: m\z: 326.4 (M) +, RT (min): 8.054 to 10.451, Area (%): 98.8. HPLC: RT (min): 5.276 to 5.377, Area (%): 96.3. 1H-NMR (400 MHz, CDC13): 5 4.09-4.07 (m, 2H), 2.33-2.29 (m, 2H), 1.67-1.58 (m, 4H), 1.16-1.34 (m, 34H), 0.80-0.90 (m, 12H). | KV100.000 | 3,4865 | 2,8102 | 0,80602 |

Table 57 shows viscosity properties of Target Fl 1.

[00288] Although the disclosed C9 oxo alcohol and Comparative 1 exhibit a generally similar average carbon number, the difference in branching index with respect to each alcohol affects viscosity properties in downstream esters. That is, the disclosed ester compositions 46 generated using the disclosed C9 oxo alcohol exhibit a lower KV, DV, and density than the comparatives (e.g., For example, Targets Fl-Fl 1). Additionally, the disclosed ester compositions 46 exhibit surprising properties. For example, Target A8 exhibits a much lower freezing point than Target F7 even though Target A8 exhibits a greater KV 100 value than Target F7. Accordingly, the viscosity properties of the disclosed ester compositions 46 may be leveraged in lubricant applications.

Examples of Diesters Generated Using LB A 32

[00289] Table 58 shows physical properties (e.g., KV, pour point, specific gravity, Noack TGA) of the disclosed diester 56,46 formed using the disclosed LBA 32 in the present disclosure. KV at 40°C (KV40) and KV at 100°C (KV100) were determined in accordance with ASTM D7042, pour points (PP) were determined in accordance with ASTM D5950, and TGA Noack was determined in accordance with ASTM D6375,

Table 58 shows properties of the disclosed diester compositions 56, 46 (e.g., an adipic diester composition) generated using LBA 32 (e.g., C13 oxo alcohol) compared to comparative adipic diesters generated using comparative alcohols (e.g., C13 alcohol comparatives) and Comparative 4 (e.g., branched CIO alcohol) with an average of 10 carbons, a branched index of 2.1, and a KV at 20°C of 21 mm²/s. [00290] Table 58 shows that the disclosed diester compositions 56, 46 generated using LBA 32 (e.g., C13 oxo alcohol) may have a KV at 40°C (KV40) between about 15 centistoke (cSt) and about 30 cSt, about 17 cSt to about 29 cSt, about 19 cSt to about 27 cSt, about 21 cSt to about 25 cSt, such as about 15, about 17, about 19, about 21, about 23, about 25, about 27, about 29, or about 31 cSt. The KV at 100°C (KV100) of disclosed diester compositions 56, 46 may range from about 0 cSt to about 10 cSt, about 2 cSt to about 8 cSt, about 4.0 cSt to about 6 cSt, such as about 0.01 cSt, about 2, about 4, about 6, about 8, or about 10 cSt.

[00291] Further, Table 58 shows example viscosity index values for diester compositions 56, 46 generated using LBA 32 (e.g., C13 oxo alcohol). The viscosity index is determined by measuring the variation in KV with respect to changes in temperature between 40°C and 100°C. In an embodiment, the disclosed diester compositions 56, 46 may have a viscosity index between approximately 140 and approximately 150, about 141 to about 149, about 143 to about 147, about 140, about 141, about 142, about 143, about 144, about 145, about 146, about 147, about 148, about 149, or about 150.

[00292] In an embodiment, the diester compositions 56, 46 generated using LBA 32 (e.g., C13 oxo alcohol) may have a pour point in Celsius (°C) ranging from about -80°C and about -70°C, about -78°C toa about -72°C, about -76°C to about -74°C, about -70, about -72, about -74, about -76, about -78, or about -80°C.

[00293] In an embodiment, the diester compositions 56, 46 generated using LBA 32 (e.g., C13 oxo alcohol) may have a specific gravity between about 0.905 and about 0.915, about 0.906 and about 0.914, about 0.907 and about 0.913, such as about 0.905, about 0.906, about 0.907, 0.908, about 0.909, about 0.910, about 0.911, about 0.912, about 0.913, about 0.914, or about 0.915.

[00294] In an embodiment, the diester compositions 56, 46 generated using LBA 32 (e.g., C13 oxo alcohol) may have a Noack TGA (thermogravimetric analysis) weight loss between about 1% to about 10%, about 2% to about 9%, about 3% to about 8%, such as about 1%, about 2%, about 3%, about 4%, about 5%, about 5%, about 7%, about 8%, about 9%, or about 10%.

[00295] Accordingly, Table 58 demonstrates that the disclosed diester compositions 56, 46 generated using the LBA 32 (e.g., C13 oxo alcohol) exhibit several advantages. For example, the diester compositions 56, 46 exhibit a larger viscosity index value (e.g., greater than 140) relative to the comparative diesters, which indicates that the diester compositions 56,46 will exhibit a more stable viscosity over a wider range of temperatures, thereby allowing them to be advantageously utilized base stocks in lubricant formulations. Additionally, the disclosed diester compositions 56, 46 exhibit a lower pour point relative to the comparatives, which indicates that the disclosed diester compositions 56, 46 can flow/pour and perform better at a lower temperature than the comparatives diesters. For example, it is generally understood that shorter alcohol-based esters will exhibit lower pour points than longer alcohol-based esters. However, it is surprising to observe that the disclosed LB A 32 C13 alcohol -based ester exhibits a lower pour point than the shorter Comparative 4 CIO alcohol -based ester. Furthermore, the diester compositions 56, 46 exhibit a lower specific gravity value than the comparative diesters which can provide advantages as it determines its utility in applications as lubricants. The disclosed diester compositions 56, 46 further exhibit little weight loss/minimal volatility (i.e., less than 10%), as indicated by the Noack TGA test, which enables the disclosed diester compositions 56, 46 to be utilized in applications such as lubricants, where having a low weight loss is desirable. As such, Table 58 demonstrates that the disclosed LBA 32, when utilized to synthesize the disclosed diester compositions 56,46, provide several advantages that can be leveraged in applications such as lubricant formulation.

[00296] With the foregoing in mind, FIG. 6 is a graph 90 illustrating friction coefficient (i.e., traction coefficient) (y-axis) versus slide-roll ratio (SRR) (x-axis) of the diester compositions 56,46 made in accordance with the method of FIG. 3 and of Table 58. The graph 90 shows traction coefficient curves (trace 92, trace 94, and trace 96) that were generated by measuring the friction coefficient of a mechanical component coated with the disclosed diester composition 56,46 and comparative diesters of Table 58 with respect to varying values of SRR in (%) using a mini traction machine (MTM). For example, the traction coefficient was measured at 40°C at 30 Newtons (N). As referred to herein, a “traction coefficient” is an analog to a friction coefficient that represents the ratio of the net tangential force to normal force in a rolling or sliding contact. In general, lower traction values are ideal for compositions that are intended to be used as lubricant compositions.

[00297] In the illustrated figure, trace 92 is representative of a comparative diester generated using the Comparative 2 alcohol, trace 94 is representative of a comparative adipic ester generated using a Comparative 4 alcohol, and trace 96 is representative of the disclosed diester compositions 56, 46 generated using the LBA 32 (e.g., C13 oxo alcohol). As shown in FIG. 6, trace 96 has a lower traction coefficient than the trace 92 and the trace 94. Without wishing to be bound by theory, it is believed that a diester exhibiting a large branching index value will exhibit a lower traction coefficient. However, these results unexpectedly demonstrate that the disclosed diester composition 56,46 generated using the disclosed LBA 32 C13 alcohol with a BI of about 2.2 (as shown in Table 2) exhibits a lower traction coefficient than the Comparative 2 alcohol -based diesters, wherein the Comparative 2 alcohol exhibits a BI of about 3. Furthermore, shorter alcohol- based esters are expected to exhibit a lower traction coefficient relative to longer alcohol-based esters. However, it is surprising to observe that the disclosed LB A 32 C13 alcohol based ester exhibits a lower traction coefficient than the shorter comparative 4 CIO alcohol based ester.

[00298] By way of example, FIG. 7 is a graph 100 illustrating friction coefficient (i.e., traction coefficient) (y-axis) versus slide-roll ratio (SRR) (x-axis) of the diester compositions 56,46 made in accordance with the method of FIG. 3. The graph 100 shows traction coefficient curves (trace 102, trace 104) that were generated by measuring the friction coefficient of a mechanical component coated with the disclosed diester 56,46 (e.g., Target Bl 3) and comparative diesters (e.g., Target D3) with respect to varying values of SRR in (%) using the MTM at 40°C 1 GigaPascals (GPa) at 3 meters/second (m/s).

[00299] In particular, trace 102 is representative of Target D3 generated using the Comparative 2 alcohol, and trace 104 is representative of the disclosed diester compositions 56, 46 generated using the LB A 32 (e.g., C13 oxo alcohol). As shown in FIG. 7, trace 104 has a lower traction coefficient than the trace 102 at 30% SRR (traction coefficient for Target D3 is about 0.0568 vs. traction coefficient for Target B13 is about 0.0415). Without wishing to be bound by theory, it is believed that a diester exhibiting a large branching index value will exhibit a lower traction coefficient. However, these results unexpectedly demonstrate that Target B13 (i.e., disclosed diester 56,46) generated using the disclosed LBA 32 with a BI of about 2.2 exhibits a lower traction coefficient than the Target D3, which is the comparative diester generated using the Comparative 2 alcohol with a BI of about 3. As such, it is presently recognized that producing diester 56,46 in accordance with the disclosed techniques may advantageously provide access to several properties (e.g., viscosity, branching index, pour point, specific gravity, Noack TGA weight loss, and traction properties), thereby allowing for utilization in applications such as lubricant formulations/composition.

[00300] Accordingly, the present disclosure is directed to techniques for producing a branched oxo alcohol (e.g., C9 alcohol, C13 alcohol, C17 alcohol) using butene and an optional propylene and subsequently utilizing the branched oxo alcohol and reacting it with precursors to produce ester compositions 46. In this way, the disclosed ester compositions 46 having certain physical properties, such as KV40, KV100, viscosity index, Noack TGA weight loss, specific gravity, and pour point are useful for lubricant applications. For example, lubricant compositions including the disclosed ester compositions 46 (e.g., diester composition 56, 46, neopentanoic ester composition 66, 46, and/or monoester composition 86, 46) may be applied to mechanical equipment consisting of a variety of moving parts (e.g., gears, joints) to reduce overall friction. In any case, the diesters may be utilized in automotive or industrial lubricant applications. [00301] 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.

[00302] Embodiment 1. A diester composition including: a plurality of branched C13 alkyl groups linked to an ester functional group, wherein the diester composition includes a viscosity index greater than 135, a pour point less than -65°C, a kinematic viscosity at 100°C less than 5.0 mm²/s, wherein the plurality of branched C13 alkyl groups has a branching index between 1.3 and 2.3, and wherein the diester composition is formed from a C13 alcohol composition and a fatty acid, wherein the C13 alcohol composition has a kinematic viscosity at 20°C less than 40.0 mm²/s.

[00303] Embodiment 2. The diester composition of the preceding claim, wherein the branching index of the plurality of branched C13 alkyl groups is between approximately 1.4 and approximately 2.2.

[00304] Embodiment 3. The diester composition of any preceding claim, wherein the diester composition has a specific gravity that is less than or equal to approximately 0.920.

[00305] Embodiment 4. The diester composition of any preceding claim, wherein the diester composition has a Noack TGA weight loss is less than or equal to 10%.

[00306] Embodiment 5. The diester composition of any preceding claim, wherein the diester composition has a kinematic viscosity at 40°C that is less than 25 mm²/s.

[00307] Embodiment 6. The diester composition of any preceding claim, wherein the C13 alcohol composition has an average carbon number between approximately 12.5 and approximately 13.5. [00308] Embodiment 7. The diester composition of any preceding claim, wherein the pour point is less than -68°C.

[00309] Embodiment 8. The diester composition of any preceding claim, wherein the kinematic viscosity at 20°C of the C13 alcohol composition is less than 37 mm²/s.

[00310] Embodiment 9. The diester composition of any preceding claim, wherein the viscosity index is greater than 140.

[00311] Embodiment 10. The diester composition of any preceding claim, wherein the diester composition has a Noack TGA weight loss is less than or equal to 6%.

[00312] Embodiment 11. A lubricant comprising the diester composition of any preceding claim.

[00313] Embodiment 12. A method, including providing a butene feedstock. The method also includes providing an optional propylene feedstock. The method further includes generating higher olefins by contacting the butene feedstock with the optional propylene feedstock in the presence of a catalyst. The method also includes fractionating the higher olefins to obtain lightly branched olefins. The method further includes hydroformylating the lightly branched olefins in the presence of a catalyst to produce C13 oxo alcohols. The method also includes performing an esterification reaction, wherein C13 oxo alcohols are contacted with diacid in the presence of catalyst, producing a di ester composition.

[00314] Embodiment 13. The method of the preceding claim, wherein average carbon number of the C13 oxo alcohol is between approximately 12.8 and approximately 13.2.

[00315] Embodiment 14. The method of any preceding claim, wherein a kinematic viscosity at 25°C of the C13 oxo alcohols is less than 37 mm²/s.

[00316] Embodiment 15. The method of any preceding claim, wherein a branching index of the C13 oxo alcohols is between approximately 1.3 and approximately 2.3.

[00317] Embodiment 16. The method of any preceding claim, wherein a pour point of the diester composition is less than -65°C.

[00318] Embodiment 17. The method of claim any preceding claim, wherein the diester composition has a Noack TGA weight loss is less than or equal to 5%. [00319] Embodiment 18. The method of any preceding claim, wherein a viscosity index of the diester composition is greater than 135.

[00320] Embodiment 19. The method of any preceding claim, wherein a specific gravity of the diester composition is less than 0.920.

[00321] Embodiment 20. The method of any preceding claim, wherein a kinematic viscosity at 100°C of the diester composition is less than 5.0 mm²/s.

[00322] Embodiment 21. A composition, including: a plurality of esters each having one or more branched alkyl chains, and wherein the one or more branched alkyl chains are selected from the group consisting of: lightly branched C9 alkyl chains having a branching index between 1.1 and 1.9; lightly branched C13 alkyl chains having a branching index between 1.1 and 2.3; or lightly branched C17 alkyl chains having a branching index between 1.9 and 2.6.

[00323] Embodiment 22. The composition of the preceding claim, wherein the plurality of esters includes adipic diesters.

[00324] Embodiment 23. The composition of any preceding claim, wherein the plurality of esters includes neopentanoic diesters.

[00325] Embodiment 24. The composition of any preceding claim, wherein the plurality of esters includes monoesters.

[00326] Embodiment 25. The composition of any preceding claim, wherein the plurality of esters each include three or more ester functional groups.

[00327] Embodiment 26. The composition of any preceding claim, wherein the one or more branched alkyl chains are the lightly branched C9 alkyl chains having a branching index between

1.1 and 1.9 and an average carbon number between 8.7 and 9.4.

[00328] Embodiment 27. The composition of any preceding claim, wherein the one or more branched alkyl chains are the lightly branched C13 alkyl chains having a branching index between

1.1 and 2.3 and an average carbon number between 12.5 and 13.5.

[00329] Embodiment 28. The composition of any preceding claim, wherein the one or more branched alkyl chains are the lightly branched C17 alkyl chains having a branching index between

2.1 and 2.4 and an average carbon number between 16.5 to about 17.5. [00330] Embodiment 29. A lubricant including the composition of any preceding claim.

[00331] Embodiment 30. The composition of any preceding claim, wherein the composition is formed from a C9 alcohol composition and a fatty acid, wherein the C9 alcohol composition has a kinematic viscosity at 20°C between 12 to 16 mm²/s and a branching index between 1.1 and 1.9.

[00332] Embodiment 31. The composition of any preceding claim, wherein the composition is formed from a C13 alcohol composition and a fatty acid, wherein the C13 alcohol composition has a kinematic viscosity at 20°C between 32 to 38 mm²/s and a branching index between 1.1 and 2.3.

[00333] Embodiment 32. The composition of any preceding claim, wherein the composition is formed from a C17 alcohol composition and a fatty acid, wherein the C17 alcohol composition has a kinematic viscosity at 20°C between 60 to 75 mm²/s and a branching index between 1.9 and 2.6.

[00334] Embodiment 33. A lubricant composition, including: a plurality of diesters each having two branched alkyl chains linked to a respective ester group of the plurality of diesters, and wherein the two branched alkyl chains are selected from the group consisting of: two lightly branched c9 alkyl chains having a branching index between 1.1 and 1.9; two lightly branched cl3 alkyl chains having a branching index between 1.1 and 2.3; or two lightly branched cl7 alkyl chains having a branching index between 2.1 and 2.4.

[00335] Embodiment 34. The lubricant composition of the preceding claim, wherein the respective ester groups of the plurality of diesters are linked via an aromatic functional group.

[00336] Embodiment 35. The lubricant composition of any preceding claim, wherein the respective ester groups of the plurality of diesters are linked via a linear alkyl chain.

[00337] Embodiment 36. The lubricant composition of any preceding claim, wherein the two branched alkyl chains are the two lightly branched cl 3 alkyl chains having a branching index between 1.1 and 2.3 and an average carbon number between 12.5 and 13.5.

[00338] Embodiment 37. The lubricant composition of any preceding claim, wherein the two branched alkyl chains are the two lightly branched c9 alkyl chains having a branching index between 1.1 and 1.9 and an average carbon number between 8.7 and 9.4. [00339] Embodiment 38. The lubricant composition of any preceding claim, wherein the two branched alkyl chains are the two lightly branched cl 7 alkyl chains having a branching index between 2.1 and 2.4 and an average carbon number between 16.5 to about 17.5.

[00340] Embodiment 39. The lubricant composition of any preceding claim, wherein the lubricant composition is formed from a C13 alcohol composition and a fatty acid, wherein the C13 alcohol composition has a kinematic viscosity at 20°C between 32 to 38 mm²/s and a branching index between 1.1 and 2.3.

[00341] Embodiment 40. The lubricant composition of any preceding claim, wherein the composition is formed from a C17 alcohol composition and a fatty acid, wherein the C17 alcohol composition has a kinematic viscosity at 20°C between 60 to 75 mm²/s and a branching index between 1.9 and 2.6.

I l l

Claims

CLAIMS:

1. A composition, comprising: a plurality of esters each having one or more branched alkyl chains, and wherein the one or more branched alkyl chains are selected from the group consisting of: lightly branched C9 alkyl chains having a branching index between 1.1 and 1.9; lightly branched C13 alkyl chains having a branching index between 1.1 and 2.3; or lightly branched C17 alkyl chains having a branching index between 1.9 and 2.6.

2. The composition of claim 1, wherein the plurality of esters comprises adipic diesters.

3. The composition of claim 1, wherein the plurality of esters comprises neopentanoic diesters.

4. The composition of claim 1, wherein the plurality of esters comprises monoesters.

5. The composition of claim 1, wherein the plurality of esters each comprise three or more ester functional groups.

6. The composition of claim 1, The composition of claim 1, wherein the one or more branched alkyl chains are the lightly branched C9 alkyl chains having a branching index between 1.1 and 1.9 and an average carbon number between 8.7 and 9.4.

7. The composition of claim 1, wherein the one or more branched alkyl chains are the lightly branched C13 alkyl chains having a branching index between 1.1 and 2.3 and an average carbon number between 12.5 and 13.5.

8. The composition of claim 1, wherein the one or more branched alkyl chains are the lightly branched C17 alkyl chains having a branching index between 2.1 and 2.4 and an average carbon number between 16.5 to about 17.5.

9. A lubricant comprising the composition of claim 1.

10. The composition of claim 1, wherein the composition is formed from a C9 alcohol composition and a fatty acid, wherein the C9 alcohol composition has a kinematic viscosity at 20°C between 12 to 16 mm²/s and a branching index between 1.1 and 1.9.

11. The composition of claim 1, wherein the composition is formed from a C13 alcohol composition and a fatty acid, wherein the C13 alcohol composition has a kinematic viscosity at 20°C between 32 to 38 mm²/s and a branching index between 1.1 and 2.3.

12. The composition of claim 1, wherein the composition is formed from a C17 alcohol composition and a fatty acid, wherein the C17 alcohol composition has a kinematic viscosity at 20°C between 60 to 75 mm²/s and a branching index between 1.9 and 2.6.

13. A lubricant composition, comprising: a plurality of diesters each having two branched alkyl chains linked to a respective ester group of the plurality of diesters, and wherein the two branched alkyl chains are selected from the group consisting of: two lightly branched c9 alkyl chains having a branching index between 1.1 and 1.9; two lightly branched cl3 alkyl chains having a branching index between 1.1 and 2.3; or two lightly branched cl7 alkyl chains having a branching index between 2.1 and 2.4.

14. The lubricant composition of claim 13, wherein the respective ester groups of the plurality of diesters are linked via an aromatic functional group.

15. The lubricant composition of claim 13, wherein the respective ester groups of the plurality of diesters are linked via a linear alkyl chain.

16. The lubricant composition of claim 13, wherein the two branched alkyl chains are the two lightly branched cl3 alkyl chains having a branching index between 1.1 and 2.3 and an average carbon number between 12.5 and 13.5.

17. The lubricant composition of claim 13, wherein the two branched alkyl chains are the two lightly branched c9 alkyl chains having a branching index between 1.1 and 1.9 and an average carbon number between 8.7 and 9.4.

18. The lubricant composition of claim 13, wherein the two branched alkyl chains are the two lightly branched cl7 alkyl chains having a branching index between 2.1 and 2.4 and an average carbon number between 16.5 to about 17.5.

19. The lubricant composition of claim 13, wherein the lubricant composition is formed from a C13 alcohol composition and a fatty acid, wherein the C13 alcohol composition has a kinematic viscosity at 20°C between 32 to 38 mm²/s and a branching index between 1.1 and 2.3.

20. The lubricant composition of claim 13, wherein the composition is formed from a C17 alcohol composition and a fatty acid, wherein the C 17 alcohol composition has a kinematic viscosity at 20°C between 60 to 75 mm²/s and a branching index between 1.9 and 2.6.