Hybrid compositions from a type of lightly branched olefins

Abstract

Provided herein is a method for generating a hybrid composition with a linear alpha olefin and lightly branched olefin. The method includes contacting a lightly branched C12 olefin (e.g., linear dodecene, 2-methyl undecene, 3-methyl undecene, 4-methyl undecene, 5-methyl undecene, 6-methyl undecene, or any combination thereof) feed stream with a linear alpha olefin feed stream, wherein the linear alpha olefin feed stream comprises a carbon length (e.g., C8, C10, C12, C14, C16, C18, larger carbons, or any combination thereof) in the presence of a catalyst, the contacting taking place under conditions to catalytically react the olefins into a hybrid oligomer. Further, the method includes hydrogenating and fractionating the hybrid oligomer, thereby producing the hybrid composition. The hybrid compositions described herein are particularly suitable for lubricant applications.

Description

HYBRID COMPOSITIONS FROM A TYPE OF LIGHTLYBRANCHED OLEFINSCROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of U.S. Provisional Application No. 63 / 567,279, filed on March 19, 2024, the entire contents of which is incorporated herein by reference.FIELD

[0002] This disclosure relates to a composition of matter and processes for producing the composition of matter that is a hybrid composition with a relatively high viscosity index and low pour point. In particular, the processes may include using a feed stream having lightly branched C12 olefins (LBO) with linear alpha olefins (LAOs) of varying carbon containing species (e.g., greater than Cs, greater that Ci6, or between Cs and Cis). The composition of matter and processes of this disclosure are especially useful for lubricant applications (e.g., 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-olefms (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 carboxylicacid. 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.SUMMARY

[0007] 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.

[0008] As discussed above, developing good performance lube stock with excellent lubricant properties such as high viscosity index, low Noack volatility, and low pour point is a challenging endeavor.

[0009] The present disclosure relates to techniques for producing or generating a hybrid composition, wherein the hybrid composition is produced from a mixture including the inventive lightly branched C12 olefin (LBOs) and linear alpha olefins (LAOs). The lightly branched C12 olefins described herein are produced using a mixture including butene and optionally propylene in the presence of a catalyst. The lightly branched C12 olefins exhibit a branching index ranging between about 1.0 and about 1.9. In some embodiments, a total sum of mono-methyl branched C12 isomers and linear C12 isomers accounts for 40-80% of LBO olefin compositions, as determined by hydrogenation gas chromatography (hydro-GC). The conditions described herein may provide a defined distribution of mono-methyl branched and linear C12 olefins based on the sum of mono-methyl branched isomers and linear dodecene (e.g., about 5 to about 15% of linear dodecene, about 5 to about 20% of 2-methyl undecene, about 10 to about 25% of 3-methyl undecene, about 15 to about 25% of 4-methyl undecene, and about 30 to about 55% of 5- and 6- methyl undecene). It has been surprisingly found that the hybrid composition produced from amixture including the lightly branched Cl 2 olefins and LAOs exhibits excellent lubricating properties such as high viscosity index (VI), low pour point, low Noack volatility, and high flash point. Accordingly, the disclosed LBOs may react with LAOs to produce hybrid compositions for lubricant base stocks in lubricant 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 process for producing LBOs and further reacting it with LAOs to produce hybrid composition, in accordance with the present disclosure;

[0013] FIG. 2 is a flow diagram of a method for producing LBOs based on butene and an optional amount of propylene, in accordance with the present disclosure;

[0014] FIG. 3 illustrates various LBO isomers made in accordance with the method of FIG. 2, in accordance with the present disclosure; and

[0015] FIG. 4 is a flow diagram of a method for producing hybrid composition based on LAOs and LBOs, in accordance with the present disclosure.DETAILED DESCRIPTION

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

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

[0018] 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.

[0019] The term "alkane" refers to non-aromatic saturated hydrocarbons with the general formula C„H(2n±2), where n is 1 or greater. An alkane may be straight chained or branched. Examples of alkanes include methane, ethane, propane, butane, pentane, hexane, heptane and octane. "Alkane" is intended to embrace all structural isomeric forms of an alkane. For example, butane encompasses n-butane and isobutane; pentane encompasses n-pentane, isopentane and neopentane.

[0020] As used herein, 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 includes the general formula CnH(2n), where n is 2 or greater. Examples of olefins include ethylene, propylene, butene, 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.

[0021] As used herein, the term “oligomer” refers to any two or more of the same or different repeating units / mer units or units. The term “hybrid composition(s)” refers to an oligomer having a linear alpha olefin and a lightly branched olefin that has subsequently been fractionated and hydrogenated. The term “oligomer composition” refers to a combination of multiple, different oligomers.

[0022] As used herein, the term “linear alpha olefin (LAO)” refers to an alkenic hydrocarbon bearing a carbon-carbon double bond at a terminal (end) carbon atom of the main carbon chain. Most often, no side chain branches are present in a LAO, although there may occasionally be a minor amount of branching component in a given LAO sample.

[0023] As used herein, the term “lightly branched olefin (LBO)” refers to an isomeric mixture of linear, mono-methyl branched, mono-alkyl (e.g., mono-methyl, mono-ethyl, mono-n-propyl, mono-z-propyl) branched, di-branched and multiple-branched alkenic hydrocarbon bearing a carbon-carbon double bond along the backbone of the molecule. The disclosed LBO in this application has a BI of 1.0-1.9 and a defined distribution of mono-methyl branched isomers.

[0024] As used herein, the term “lightly branched olefin composition (e.g., LBO composition)” refers to a mixture that includes linear, mono-methyl branched, mono-alkyl (e.g., mono-methyl, mono-ethyl, mono-n-propyl, mono-z-propyl) branched, di-branched, multiple-branched, lighter, higher alkenic hydrocarbon bearing a carbon-carbon double bond along the backbone of the molecule. The LBO composition may be fractionated to obtain the disclosed lightly branched olefin. At least in some instances, the lightly branched olefin composition may include cycloalkanes, dienes, or other hydrocarbon products other than the linear, mono-methyl branched, mon-alkyl branched, di-branched, multiple-branched, lighter, higher alkenic hydrocarbons mentioned above. It should be noted that the LBO composition may also include small amounts (e.g., trace amounts) of diene and cyclic olefins.

[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. Product carbon number distribution and average branching as well as dodecene (C12H24) isomers were detected off-line by Agilent 8890 GC equipped by a 100-meterDB -Petro column (0.25 mm I D., 0.5 pm film thickness) equipped with a H2 gas line and Pt / ALCL catalyst for hydrogenation of the olefins prior to the GC analysis, which hydrogenates the olefins prior to the GC analysis similar to described in WO2022233875A1. Accordingly, hydrocarbons ranging from 5 to over 17 carbon atoms were identified and quantified with this GC method. In addition, the latter further allowed to quantify isomers or group of isomers for C12H24, among others, and the corresponding average branching index (BI) that was calculated using equation Eq. 1,where BI is the average branching index of C12H24, wt%'inear, wt%mono branched, wt%dibranched, andsumme(jweight fractions in the product effluent of all the C12H24 isomers that possess no branched alkyl groups, or have a single, two, or three or more branches, respectively. Isomers containing a single methyl, ethyl or propyl branch are all considered monobranched since a singular hydrogen atom has been exchanged for an alkyl group. Furthermore, the summed weight fractions of each isomer group are weighted by a branching factor, BF, which value is set to 0, 1, 2, or 3 for linear, monobranched, dibranched, and multibranched, respectively. Therefore, if BI is close to 0, C12H24 will be predominantly linear onaverage, while if it approaches 3, its isomer distribution will be shifted towards a highly branched one. Finally, using the aforementioned GC method, the C12H24 isomer distribution was determined according to the retention times for selected isomers. Since the hydro-GC fully hydrogenates all olefins in the samples, the peaks detected are those of dodecane (C12H26) and its structural isomers, whose distribution directly reflects that of C12H24. However, for simplicity and clarity, the relative amounts (e.g., percentages) of hydrocarbons present in the LBO composition will be discussed in terms of the corresponding alkenes, rather than the alkanes that were determined using hydro-GC. Further, although the relative amounts of hydrocarbons (i.e., linear, mono-methyl branched, dibranched, multiple-branched, lighter, higher alkenic hydrocarbons) discussed herein were characterized using hydro-GC, it should be noted that the relative amounts may be characterized by other suitable techniques that include, but are not limited to, high performance liquid chromatography (HPLC), Fourier Transform infrared spectroscopy (FTIR), and GC-MS.

[0026] The average carbon number is determined by C13NMR It utilizes the unsaturated and saturated 13C integrals and relies on the assumption that all unsaturated carbons are olefins and there is an average of one olefinic bond per molecule.

[0027] 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.

[0028] Reference is now made to the embodiments illustrated in FIGS. 1-4 wherein like numerals are used to designate like parts throughout.Lightly Branched Olefins

[0029] FIG. 1 illustrates a flow diagram of a process 10 for producing LBOs and further reacting it with LAOs to produce hybrid composition in accordance with the present disclosure. As shown, the process 10 includes, at block 12, providing a butene (e.g., a butene feedstock, wherein the butene feedstock may include isomers of butene (e.g., 1 -butene, 2-butene, isobutylene) and, optionally propylene (e.g., a propylene monomer feed) to a reactor. The process 10 includes, at block 14, contacting butene and the propylene, in embodiments when propylene is used, in the presence of a catalyst to form lightly branched C12 olefins (LBOs) after fractionation. As described herein, the LBOs may include advantageous properties, or combinations thereof, such as branchingindex, for use as a feedstock for producing alcohols as described in WO2022233878A1 and WO2022233879A1 or oligomers which are further hydrogenated to form hybrid composition, among other physical properties, that provide suitable uses. Further, the process 10 includes, at block 16, contacting the LBOs with linear alpha olefins (LAOs) of varying carbon lengths (Cs, Cio, C12, C14, Ci6, Cis, larger carbons, or any combination thereof) in the presence of a catalyst to form hybrid oligomers. In particular, the hybrid oligomers described herein may include advantageous properties after hydrogenation and fractionation, such as viscosities (e.g., kinematic viscosity, viscosity index), Noack thermogravimetric analysis (TGA) weight loss, flash points, pour points, among other physical properties, that provide suitable properties advantageous for lubricant base stock application.

[0030] As discussed above with respect to block 14 of the process 10, an LBO may be produced by contacting butene and (optionally) propylene in the presence of catalyst. To illustrate one example of the block 14, FIG. 2 illustrates a flow diagram of a method 20 for synthesizing the LBOs in accordance with certain embodiments of the present disclosure. As shown, the method 20 includes providing butene 22 (e.g., a butene feedstock) and optionally propylene 24 (e.g., a propylene feedstock) in the presence of a catalyst 26, wherein the butene 22 and the propylene 24 are contacted in the presence of a catalyst 26 to produce an LBO olefin composition 30.

[0031] Referring to the method 20, at block 28, butene 22 and the optional propylene 24 are contacted in the presence of a catalyst 26. For example, the catalysts were disclosed in US 11,905,227 B2, US 11,312,669 B2, WO2022233875A1, WO2022233876A1 such as a zeolite catalyst. In some embodiments contacting butene 22 and, optionally, propylene 24 in the presence of the catalyst 26 may include providing a flow of a feedstock (e.g., butene feed flow rate and the optional propylene feed flow rate) including the butene 22 and the optional propylene 24 over a solid support formed of the catalyst 26 into a reactor. For example, the catalyst 26 may be stored or otherwise contained in a reaction vessel, and the feedstock including butene 22 and 24 may be provided, flowed, or otherwise directed into the reaction vessel including the catalyst 26. In some embodiments, the reactor may be a single fixed bed reactor or preferably a multi-tubular reactor.

[0032] Solid acid catalysts suitable for producing olefin oligomers having an average branching index of about 1.9 or less, particularly for C 12 olefin oligomers having an average branching index of about 1.9 or less, such as an average branching index of about 1.0 to about 1.9, may include, for example, zeolite catalysts having an MTT or TON framework, including unmodified zeolite catalysts having these frameworks. Suitable examples may include, for instance, ZSM-22, ZSM-23, ZSM-57, and SAPO-11 . Such solid acid catalysts and other zeolite catalysts may be modified by steaming, modified with an organic acid, modified with a transition metal, modified with coke, impregnated with NiO, or any combination thereof Suitable modification conditions are described further below. Although already suitable for producing an average branching index of about 1.9 or less, such modifications to these zeolite catalysts may further improve selectivity and / or decrease the average branching index, as explained further below.

[0033] Such solid acid catalysts may afford selectivity for forming C10-C13 olefin oligomers when exposed to suitable oligomerization reaction conditions, wherein selectivity may be characterized, in at least one embodiment, by production of at least about 10% C12 olefin oligomers and at least about 25% C10-C13 olefin oligomers, based upon total olefin oligomers produced in the oligomerization reaction. C12 olefin oligomers having an average branching index of about 1.9 or less, preferably about 1.0 to about 1.9, may be produced under these oligomerization reaction conditions. Other examples of solid acid catalysts suitable for producing olefin oligomers, particularly with selectivity toward formation of C10-C13 olefin oligomers, may include, for example, zeolite catalysts having an MTT, MWW, MRE, MFI, MTW or TON framework, wherein the zeolite catalyst is further modified by steaming, modified with an organic acid, modified with a transition metal, modified with coke, modified by impregnation with NiO, or any combination thereof. Such zeolite catalysts may afford a selectivity value exceeding 25% when producing C10-C13 olefin oligomers under suitable oligomerization reaction conditions. In general, preparation of the zeolite catalysts described herein may be prepared as described in WO2022233879A1, which is incorporated herein by reference.

[0034] Referring to the method 20, at block 32, the LBO olefin composition 30 undergoes a fractionation process, wherein the process results in higher olefins 36 (e.g., olefins heavier than C12, such as Ci6, C20, C24, etc.), lighter olefins 38 (e.g., olefins lighter than C12, such as C4 feed, C8), and lightly branched olefins (LBO) 34 (e.g., lightly branched C12 olefins including one or more of linear dodecenes, mono-methyl branched isododecenes, mono-alkyl branched isododecenes, di-branched isododecenes, multi-branched isododecenes, and, in some instances, trace amounts of cyclic alkanes and dienes. As described here, the LBOs 34 may include advantageous properties, or combinations of properties, such as branching index, for use as a feedstock for producing oligomers, or overall weight percent of isomer composition.

[0035] The LBOs 34 include linear dodecenes and mono-methyl branched isododecenes (e.g., mono-methyl branched C12 isomers), wherein the mono-methyl branched isododecenes includesone or more of 2-methyl undecene, 3-methyl undecene, 4-methyl undecene, 5-methyl undecene, 6-methyl undecene, or any combination thereof. The branching index of the LBOs 34 may be between approximately 1.0 to 1.9 and the average carbon number is between 11.2 and approximately 12.8. The LBOs 34 were characterized using techniques including, but not limited to, hydro-GC, to determine overall weight percent of the isomer compositions (e.g., 2-methyl undecene, 3-methyl undecene, 4-methyl undecene, 5-methyl undecene, 6-methyl undecene, or any combination thereof). As noted above, techniques such as high-performance liquid chromatography (HPLC), Fourier transform infrared spectroscopy (FTIR), and mass spectrometry, may be used to determine overall isomer compositions. As noted above, hydro-GC characterization produces the alkane hydrocarbons instead of the alkene hydrocarbons mentioned above. However, for simplicity and clarity, the compositions are discussed in terms of the alkenes.

[0036] Accordingly, FIG. 3 illustrates examples of various LBO 34 isomers made in accordance with the method of FIG. 2, in accordance with certain embodiments of the present disclosure. In particular, the sum of mono-methyl branched and linear C 12 isomers account for 40-80% of LBO 34 isomers. In general, the mono-methyl branched isododecenes and linear dodecenes after hydrogenation includes approximately 5 to 15% linear dodecane, 5 to approximately 20 wt% 2- m ethyl undecane, approximately 10 to approximately 25 wt% 3-methyl undecane, approximately 15 to approximately 25 wt% 4-methyl undecane, and approximately 30 to approximately 55 wt% 5-methyl undecane, 6-methyl undecane, or both. Several non-limiting examples of the composition of the LBOs 34 are described below.Hybrid compositions

[0037] As discussed above with respect to block 16 of the process 10, a hybrid composition may be produced by contacting LBOs 34 with LAO in the presence of catalyst. To illustrate one example of the block 16, FIG. 4 illustrates a flow diagram of a method 40 for producing the hybrid compositions 54 based on LAOs and LBOs, in accordance with certain embodiments of the present disclosure. As shown, the method 40 includes providing LBOs 34 (e.g., an LBO feedstock, wherein the feedstock includes one or more of linear dodecene, 2-methyl undecene, 3-methyl undecene, 4-methyl undecene, 5-methyl undecene, 6-methyl undecene, or any combination thereof) and a linear alpha olefin (LAO) 42 of varying carbon lengths (Cs, Cio, C12, C14, Ci6, Cis, larger carbons, or any combination thereof) in the presence of catalyst 46, wherein LAO 42 andLBO 34 are contacted in the presence of a catalyst 46 to produce a hybrid oligomer 48. The hybrid oligomer is further fractionated and hydrogenated, thereby producing the hybrid composition 54. As described here, the hybrid composition 54 may include advantageous properties, or combinations of properties, such as kinematic viscosity, viscosity index, Noack volatility, flash points, pour points, among other physical properties, that provide suitable lubrication applications.

[0038] Referring to method 40, at block 44, LAO 42 and LBO 34 are contacted in the presence of a catalyst 46, wherein the catalyst 46 may include a catalyst and optionally an activator. In some embodiments, contacting LAO 42 and LBO 34 in the presence of the 46 may include providing a flow of a feedstock (e.g., LAO feed flow rate and LBO feed flow rate) including the LAO 42 and an LBO 34 with an active catalyst 46. For example, the catalyst 46 may be stored or otherwise contained in a reaction vessel, and the feedstock including LAO 42 and LBO 34 may be provided, flowed, or otherwise directed into the reaction vessel including the catalyst 46. The relative amounts (e.g., molar ratio) of the LBO 34 and the LAO 42 (e.g., LBO 34:LAO 42) may be approximately 10: 1, 5: 1, 3: 1, 2: 1, 1 : 1, 1.5:5, 1 :2, 1 :3, 1 :5, 1 : 10. For example, the molar ratio of LBO 34 to LAO 42 may range from 0.1 : 1 to 10: 1, more preferably 1.5: 1, and so on. In some embodiments, the relative amounts of the LAO 42 and the LBO 43 less than or equal to approximately 5: 1 (e.g., 4.9: 1, 4.8: 1, 4.7: 1, and so on), less than or equal to approximately 4: 1, less than or equal to approximately 3:1, less than or equal to approximately 2: 1, or less than or equal to approximately 1 : 1.

[0039] The catalyst 46 may be a suitable Lewis acid catalyst, such as boron trifluoride (BF3), alkyl aluminums, aluminum halides (e.g., AICI3), or Friedel-Crafts catalyst. For example, the catalyst 46 may be boron trifluoride alone or complexed with activators (e.g., promoters) including water or alcohols (e.g., ethanol, propanol, butanol). In some embodiments, the boron trifluoride may be complexed with other activators, for example carboxylic acids or esters such as ethyl acetate or ethyl propionate. Suitable catalysts that may be used as the catalyst 46 are described in U.S. Patents 4, 149,178 and 3,382,291, the relevant portions of which are incorporated by reference herein. Other descriptions of PAO synthesis can be found in the following U.S. Patent Nos.: 3,742,082; 3,769,363; 3,876,720; 4,239,930; 4,367,352; 4,413,156; 4,434,408; 4,910,355; 4,956,122; and 5,068,487, US 8,865,959, US 5,498,815 and US 2022 / 0298087. The dimers of Ci4to Ci8 olefins are described in U.S. Patent No. 4,218,330.

[0040] Alternatively or additionally, the catalyst 46 may include one or more non-metallocene Ziegler-Natta catalysts. Alternatively or additionally, the catalyst system can include a metal oxidesupported on an inert material, (e.g., chromium oxide supported on silica). Such catalyst systems and uses thereof in the process for making PAOs are disclosed in the following U.S. Patent Nos. : 4,827,073; 4,827,064; 4,967,032; 4,926,004; and 4,914,254, the relevant portions of which are incorporated by reference herein.

[0041] Referring to the method at block 44, the process 40 includes the contacting of LAO 42 and LBO 34 in the presence of catalyst 46 to form the hybrid oligomer 48. In some embodiments, the resulting hybrid oligomer 48 may be provided, flowed or otherwise directed for fractionation, as described in block 50. For example, fractionation may include fractionating a boiling point range of oligomers from monomers of both LBO and LAO. Further, at block 52, the hybrid oligomer 48 may be hydrogenated, thereby producing hybrid composition 54. In other embodiments, the hybrid oligomer may be hydrogenated prior to fractionation. For example, contacting the LAO 42 and the LBO 34 in the presence of the catalyst 46 may form an oligomer composition. Then, a portion of the oligomer composition may be fractionated by fractionating at a particular viscosity range (e.g., kinematic viscosity at 40°C between 9.0 to 20.0 cSt or a kinematic viscosity at 100°C between 2.0 to 4.5 cSt). As such, the fractionated portion of the oligomer composition is the hybrid oligomer 48. Accordingly, the hybrid composition 54 may include advantageous properties, or combinations of properties, such as kinematic viscosity, viscosity index, Noack volatility, flash points, pour points, among other physical properties, that provide properties advantageous for lubricant base stock application. Several non-limiting examples of the composition of the hybrid oligomers 54 are described below.

[0042] All kinematic viscosity values in this disclosure are as determined pursuant to ASTM D445 or ASTM 7279. Kinematic viscosity at 100°C is reported herein as KV100, and kinematic viscosity at 40°C is reported herein as KV40. Unit of all KV100 and KV40 values herein is cSt unless otherwise specified.

[0043] All viscosity index (“VI”) values in this disclosure are as determined pursuant to ASTM D2270.

[0044] All flash point values in this disclosure are as determined pursuant to ASTM D6450.

[0045] All Noack volatility (“NV”) values in this disclosure are as determined pursuant to ASTM D5800 or ASTMD6375 unless specified otherwise. Unit of all NV values is wt%, unless otherwise specified.

[0046] All pour point values in this disclosure are as determined pursuant to ASTM D5950 or D97.ExamplesLBO Olefin Catalyst, Reaction Conditions, and Examples

[0047] The LBO C12 olefins are prepared by ZSM-23 zeolite catalysts. The ZSM-23 catalyst can be prepared using the recipe described in U.S. Pat. Nos.: 4,076,842, 5,332,566, 8,500,991, and 11,312,669 B2 to have a Si / Ah molar ratio of 40. The catalysts were not impregnated with a metal and were not treated with an amine. The ZSM-23 zeolite was shaped into a quadrulobe extrudate with a diameter between 1 / 10” and 1 / 20” using an AI2O3 binder and ultimately steamed. The reaction was carried out at a temperature of 170°C to 300°C, a weight hourly space velocity (WHSV) of 2 hr1to 20 h-1, and a pressure of 70 bar. All the compositions were benchmarked against a standard feed, referred to as clean feed, composed of 1 -butene as the primary olefin reactant, isobutane and butane as balance with a typical composition of l-butene:butane:isobutane at relative wt.% of 5:4: 1.

[0048] The oligomerization reaction was carried out in a fixed bed reactor with an internal diameter of 13 mm, which was loaded with 8-10 grams of catalyst particles with a size of 1-1.18 mm diluted with SiC. Prior to the reaction, the catalyst was heated up to 170°C under N2 and maintained overnight for drying. The reaction was operated in downflow mode. Mass flow controllers delivered the hydrocarbon feed to the catalyst.Table 1 : Example A of LBOs 34 shows a distribution of mono-methyl branched isododecenes and linear dodecene based on the sum of mono-methyl branched isododecenes and linear dodecenes.

[0049] Example A: The oligomerization reaction was run with a clean feed over a ZSM-23 catalyst at a WHSV of 10 hr-1, per-pass conversion (PPC) of 70% to 80% and a temperature of 225 to 245 °C. The fractionated lightly branched C12 cut product was subjected to hydro-GC andNMR characterization with the method described in the Detailed Description section. The results were summarized in Table 1.Table 2: Example B of LBOs 34 shows a distribution of mono-methyl branched isododecenes and linear dodecene based on the sum of mono-methyl branched isododecenes and linear dodecenes.

[0050] Example B: The oligomerization reaction was run by co-feeding 1-C4H8 and C8H16 as olefins reactants at a relative wt.% of 1: 1.1 over a ZSM-23 catalyst and in the presence of 350 wt.ppm of butadiene (C4H6) and 0.2 wt. ppm of acetonitrile (CH3CN). Additional reaction parameters included a WHSV of 10 hr-1, a PPC of 50% to 60% and a temperature of 170 to 190 °C. Isomer analysis of C12H24 yielded an average branching index of 1.3 and a distribution that is summarized in Table 2.Table 3: Example C of LBOs 34 shows a distribution of mono-methyl branched isododecenes and linear dodecene based on the sum of mono-methyl branched isododecenes and linear dodecenes.

[0051] Example C: The oligomerization reaction was run by feeding I-C4H8 as olefin reactant over a ZSM-23 catalyst in the presence of 500 wt.ppm of butadiene (C4H6), 0.3 wt.ppm of acetonitrile (CH3CN) and 1 wt.% of isobutylene (i-C4Hs) at a WHSV of 10 hr1, a PPC of 80 to90% and a temperature of 190 to 210°C. Isomer analysis of C12H24 yielded an average branching index of 1.3 and a distribution that is summarized in Table 3.

[0052] In general, Tables 1, 2, and 3 (e.g., Tables 1-3) below show examples of a distribution of the different LBO C12 isomers 34 produced in accordance with the method 20 as disclosed in FIG. 2 in weight percent. As described herein, LBOs 34 are formed by contacting butene 22 with, optionally, propylene 24 in the presence of catalyst 26, which produces LBO olefin composition 30. LBO olefin composition 30 is then fractionated, resulting in LBOs 34. With respect to Tables 1-3, the LBOs 34 were hydrogenated for ease of characterizing the composition of the LBOs 34. As such, the compositional ranges for mono-methyl branched isododecenes and linear dodecenes may be used interchangeably for mono-methyl branched isododecanes and linear dodecanes. The composition of the LBOs 34 was characterized using hydro- gas chromatography (GC). In general, LBOs 34 includes 40-80% mono-methyl branched isododecenes and linear dodecenes. For example, mono-methyl branched isododecenes and linear dodecenes may range between 45% and 75%, 50% and 70%, 55% and 65%, about 40%, about 45, about 50, about 55, about 60 about 65, about 70, about 75, or about 80%.

[0053] Tables 1-3 further show examples of the branching indices of the LBOs 34. The branching index of LBOs 34 may range between about 1.0 and about 1.9, about 1.1 and about 1.7, or about 1.3 and about 1.5.

[0054] Additionally, Tables 1-3 further show examples of the distribution of mono-methyl branched isododecenes and linear dodecene based on the sum of mono-methyl branched isododecenes and linear dodecenes. Further, linear dodecene may range between approximately 5% to approximately 15% of the total sum of mono-methyl branched isododecenes and linear dodecenes. For example, linear dodecenes may range between 7% to 13%, 9% to 11%, about 5%, about 7%, about 9%, about 11%, about 13%, or about 15%.

[0055] Tables 1 -3 further describe the distribution of the types of LBOs 34 produced as described in the present disclosure. In general, 2-methyl undecane may range between approximately 5 to approximately 20%. For example, 2-methyl undecane may have a range between approximately 7% to 19%, 9% to 17%, 11% to 15%, about 5, about 7, about 9, about 11, about 13, about 15, about 17, or about 19%. In another embodiment, 3 -methyl undecane may range between approximately 10 to approximately 25%. For example, 3-methyl undecane may range between 11 % to 23%, 13% to 21%, 15% to 19%, about 10, about 12, about 14, about 16, about 18, about 20, about 22, or about 24%. Further, 4-methyl undecane may range between approximately 15 toapproximately 25 wt%. For example, 4-methyl undecane may have a range between 17% to 23%, 19% to 21%, about 15, about 17, about 19, about 21, about 23, or about 25%. In another embodiment, 5-methyl undecane, 6-methyl undecane, or both, may range between approximately 30 to 55%. For example, 5-methyl undecane, 6-methyl undecane, or both, may range between 35% to 50%, 40% to 45%, about 30, about 32, about 34, about 36, about 38, about 40, about 42, about 44, about 46, about 48, about 50, about 52, or about 54.

[0056] In general, Examples A, B and C demonstrate that the LBOs 34 obtained using the ZSM- 23 catalyst is compositionally consistent regardless of the C4-based feedstock or the reaction conditions.Hybrid Compositions Catalyst, Reaction Conditions, and Examples

[0057] Example D: Abase stock made from LBO C12 olefin and LAO C12 — A flask was charged with 22.5g of LBO C12 olefin, 15g of 1-dodecene (LAO C12) and 5 mL of an n-Butanol, n- butylacetate mixture in a 1 :9 molar ratio. The solution was cooled to 0°C with stirring and then BF3 gas was sparged through the solution for 2 hours (h). Gas chromatography of the crude mixture showed 80% LBO-LAO dimer product formation. The reaction was purged with nitrogen, quenched with water, and then the organic layer was separated and distilled under reduced pressure (2 mbar pressure heating at 150-180 °C) to remove unreacted starting materials to yield 20.5 g of undistilled product material. The undistilled product material was hydrogenated over Pd / C with 10 mL of hexane for 36 h under 10 barH2 at 120 °C for 36h. Following hydrogenation, the solution was filtered through CELITE and then purified by distillation to yield 8.5 g of D as a mixture of isomers. Product was characterized by gas chromatography with El mass spectrometry: m / z 336 (M-H2), m / z 281 (M-C4H9), m / z 225 (M-C8HI7), m / z 154 (M-CI3H2S).

[0058] The base stock product of this Example D exhibits a low KV100, a high viscosity index, a low NOACK, and a low pour point, rendering it suitable as a primary base stock or a co-base stock in low viscosity formulated lubricants or cooling fluids.

[0059] Example E: A base stock made from LBO C12 olefin and LAO C14, the synthesis procedure and characterization method are similar to Example D, which yields 11g of E as a mixture of isomers. Product was characterized by gas chromatography with El mass spectrometry: m / z 365 (M-H), m / z 323 (M-C3H7), m / z 238 (M-C9H19).

[0060] Example F: A base stock made from LBO C12 olefin and LAO C16, the synthesis procedure and characterization method are similar to Example D, which yields 8.5g of F as a mixture of isomers. Product was characterized by gas chromatography with El mass spectrometry: m / z 337 (M-C4H9), m / z 308 (M-C6HI4).

[0061] Example G: A base stock made from LBO C12 olefin and LAO C18, the synthesis procedure and characterization method are similar to Example D, which yields 8.5g of G as a mixture of isomers. Product was characterized by gas chromatography with El mass spectrometry: m / z 422 (M), m / z 365 (M-C4H9), m / z 337.40 (M-C6HI4), m / z 308 (M-CsHn).Table 4 shows physical properties of the hybrid compositions 54 produced using linear alpha olefins and the disclosed lightly branched C12 olefins.

[0062] As shown in Table 4, the hybrid compositions 54 produced using the LBOs 34 exhibit advantageous properties such as high VI, high flash point, low Noack volatility, relative to the commercial product produced from the GTL route and other comparatives (e.g., Yubase 4 (Gr III), GTL 4 (Gr III), and PAO 4 (Gr IV)). The control sample (e.g., Control) includes a hybrid composition that was formed by reacting the LBO 34 with itself. As such, the VI of the control sample is 44, which is significantly lower than the VI for a hybrid composition 54 produced by LAO C12 and LBO 34 (e.g., Example C, Table 4). Further, the Noack volatility of the hybrid composition 54 produced by LBO 34 and LAO C12 is lower than the control sample.

[0063] In general, Table 4 shows the kinematic viscosity of the hybrid compositions 54 comprising LAOs 24 of varied lengths (e.g., C8, CIO, C12, C14, C16, C18, larger carbons, or any combination thereof) and the disclosed LBOs 34. Accordingly, the hybrid compositions 54 may have an average carbon number ranging between Cl 8 to C30. For example, the hybrid compositions 54 may have an average carbon number between C20 and C28, C22 and C26, about C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, about C28, about C29, or about C30. Hybrid compositions 54 may have a kinematic viscosity at 40°C (KV40) between approximately 5 centistoke (cSt) and approximately 20 cSt. For example, the hybrid compositions 54 may have a kinematic viscosity at 40°C (KV40) between 5 cSt and 19 cSt, 7 cSt and 17 cSt, 9 cSt and 15 cSt, 11 cSt and 13 cSt, about 5 cSt, about 7 cSt, about 9 cSt, about 11 cSt, about 13, about 15, about 17, or about 19 cSt. Further, Table 4 shows the kinematic viscosity at 100°C (KV100) of hybrid compositions 54. It is noted that the hybrid compositions 54 may have a kinematic viscosity at 100°C (KV100) between approximately 1.5 cSt and approximately 4.5 cSt. For example, the hybrid compositions 54 may have a kinematic viscosity at 100°C (KV100) between 1.5 cSt and 4.0 cSt, 2.0 cSt and 3.5 cSt, 2.5 cSt and 3.0 cSt, about 1.6 cSt, about 1.8 cSt, about 2.0 cSt, about 2.2 cSt, about 2.4, about 2.6, about 2.8, about 3.0, about 3.2, about 3.4, about 3.6, about 3.8, about 4.0, about 4.2, or about 4.4 cSt.

[0064] Further, Table 4 shows example viscosity index (VI) values for hybrid compositions 54. The viscosity index is determined by measuring the variation in kinematic viscosity with respect to changes in temperature between 40°C and 100°C. For example, hybrid compositions 54 may have a viscosity index between approximately 40 and approximately 145. It is noted that the hybrid compositions 54 may have a viscosity index between 50 and 135, 60 and 125, 70 and 115, 80 and 105, about 40, about 45, about 50, about 55, about 60, about 65, about 70, about 75, about 80, about 85, about 90, about 95, about 100, about 105, about 110, about 115, about 120, about 125,about 130, about 135, about 140, or about 145. It is presently recognized that hybrid compositions 54 that exhibit a large viscosity index value (e.g., greater than 100) will advantageously demonstrate a more stable viscosity over a wider range of temperatures, allowing them to be utilized in applications including, but not limited to, cooling fluids and lubricants.

[0065] In another embodiment, Table 4 shows Noack TGA weight loss results for hybrid compositions 54. It is noted that hybrid compositions 54 may have weight loss results between approximately 5% and 100%. For example, weight loss may be between 10% and 95%, 15% and 90%, 20% and 85%, 25% and 80%, 30% and 75%, 35% and 70%, 40% and 65%, 45% and 60%, 50% and 55%, about 6%, about 12, about 18, about 24, about 30, about 36, about 42, about 48, about 54, about 60, about 66, about 72, about 78, about 84, about 90, about 96, or about 100%. It should be noted that hybrid compositions 54 that consisting of shorter LAOs (e.g., Example 1, Example 2, and Example 3) are more volatile. In general, it is advantageous for hybrid compositions 54 to exhibit little weight loss or minimal volatility (e.g., less than 15%, less than 10%, less than 5%), as this allows hybrid compositions to be utilized in applications such as cooling fluids and lubricants, where these properties would be desirable.

[0066] Table 4 also shows the pour point in Celsius (°C) for hybrid compositions 54. Hybrid compositions 54 may have exhibit a pour pint < -83°C. For example, hybrid compositions may have a pour point between approximately -83°C and -10°C. It is noted that the hybrid compositions 54 may have a pour point between -80°C and -15°C, -75°C and -20°C, -70°C and -25°C, -65°C and -30°C, -60°C and -35°C, -55°C and -40°C, -50°C and -45°C, about -84°C, about -74, about -64, about -54, about -44, about -34, about -24, or about -14°C. As such, obtaining a low pour point (e.g., less than or equal to -83°C) temperature is advantageous, as it determines its utility in applications such as lubrications.

[0067] In any case, the hybrid compositions 54 may be utilized as lubricant base stocks for lubricant applications. For example, hybrid compositions 54 may be utilized in the lubrication of mobile and stationary mechanical systems and components, which include, for example, mobile or stationary systems, mobile or stationary power systems, vehicles, engines, pistons, piston rings, cylinder liners, cylinders, cam shafts, cams, tappets, lifters, bearings (journal, roller, tapered, needle, ball, and others), drivelines, drivetrains, powertrains, transmissions, power transfer systems, differentials, gears, gear trains, gear sets, gear boxes, bearings, bushings, axles, turbines, compressors, pumps, hydraulic systems, valves, seals, filters, and others.

[0068] Further, the hybrid compositions 54 may be utilized to transfer heat from heat-generating components of electric vehicles and other apparatuses or locales in need of effective thermal management via direct contact (e.g., direct thermal contact). The heat-generating components may include one or more batteries, power electronics, or electric vehicle power components. As described above, the disclosed hybrid compositions may be used in direct cooling applications (e.g., direct cooling fluid contact) due to the relatively low electrical conductivity of the hybrid compositions. In any case, the hybrid compositions may be utilized in systems that include heatgenerating components. In some embodiments, the heat-generating components may include components utilized in data center cooling.

[0069] Accordingly, the present disclosure is directed to techniques for producing a lightly branched C12 olefin using butene and the optional propylene and subsequently utilizing the lightly branched C12 olefin and reacting it with LAOs that include carbons of varying lengths to produce hybrid compositions. For example, the LAO streams may include Cs carbons, C10 carbons, C12 carbons, CM carbons, Cis carbons, Ci6 carbons, or larger carbons, or a combination thereof. In general, the LAO streams may be characterized by a C# number that is about 8-18. It is presently recognized that such a LAO stream in the presence of the lightly branched C12 olefin may produce a hybrid composition or hydrocarbon fluid stream having certain physical properties, such as KV40, KV100, viscosity index, Noack TGA weight loss, flash point, and pour point that are useful for lubricant applications. Technical effects of the present disclosure also include compositions for direct heat transfer applications and lubricant applications.

[0070] The present invention is well adapted to attains the ends and advantages mentioned as well as those that are inherent therein. The particular embodiments disclosed above are illustrative only, as the described isomeric composition may be achieved in different but equivalent manners apparent to those skilled in the art having the benefit of the teachings herein. Furthermore, no limitations are intended to the span of isomer ratios herein shown, other than as described in the claims below. It is therefore evident that the particular illustrative embodiments disclosed above may be altered, combined, or modified and all such variations are considered within the scope and spirit of the present invention.

[0071] 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 otherembodiments / 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.

[0072] Embodiment 1. An olefin composition including an average carbon number is between approximately 11.2 and approximately 12.8; and a branching index between approximately 1.0 and approximately 1.9; wherein the olefin composition comprises greater than or equal to 40 wt% of the sum of mono-methyl branched isododecenes and linear dodecenes, and wherein the monomethyl branched isododecenes comprise one or more of 2-methyl undecene, 3-methyl undecene, 4-methyl undecene, 5-methyl undecene, and 6-methyl undecene.

[0073] Embodiment 2. The olefin composition of the preceding claim, wherein approximately 40 to approximately 80 wt% of the mono-methyl branched isododecenes and linear dodecene.

[0074] Embodiment 3. The olefin composition of any preceding claim, wherein approximately 5 to approximately 15 wt% of linear dodecene of a total sum of mono-methyl branched isododecenes and linear dodecene.

[0075] Embodiment 4. The olefin composition of any preceding claim, wherein approximately 5 to approximately 20 wt% 2-methyl undecane of a total sum of mono-methyl branched isododecenes and linear dodecene.

[0076] Embodiment 5. The olefin composition of any preceding claim, wherein approximately 10 to approximately 25 wt% 3-methyl undecane of a total sum of mono-methyl branched isododecenes and linear dodecene.

[0077] Embodiment 6. The olefin composition of any preceding claim, wherein approximately 15 to approximately 25 wt% 4-methyl undecane of a total sum of mono-methyl branched isododecenes and linear dodecene.

[0078] Embodiment 7. The olefin composition of any preceding claim, wherein approximately 30 to approximately 55 wt% 5-methyl undecane, 6-methyl undecane, or both of a total sum of mono-methyl branched isododecenes and linear dodecene.

[0079] Embodiment 8. The olefin composition of any preceding claim, wherein the olefin composition comprises greater than or equal to 45 wt% of the mono-methyl branched isododecenes and linear dodecene.

[0080] Embodiment 9. The olefin composition of any preceding claim, wherein approximately 30 to approximately 55 wt% 5-methyl undecane, 6-methyl undecane, or both of a total sum of mono-methyl branched isododecenes and linear dodecene

[0081] Embodiment 9. A hybrid composition produced from a mixture including lightly branched C12 olefins and a linear alpha olefin of varying carbon lengths, wherein a linear alpha olefin can be Cs, Cio, C12, CM, Ci6, Cis, larger carbons, or any combination thereof, and wherein the lightly branched C12 olefins comprise mono-methyl branched isododecenes.

[0082] Embodiment 10. The hybrid composition of the preceding claim, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins have a kinematic viscosity at 40°C between 9.0 to 20.0 cSt.

[0083] Embodiment 11. The hybrid composition of any preceding claim, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins have a kinematic viscosity at 100°C between 2.0 to 4.5 cSt.

[0084] Embodiment 12. The hybrid composition of any preceding claim, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a viscosity index between approximately 120 and approximately 140.

[0085] Embodiment 13. The hybrid composition of any preceding claim, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a viscosity index is approximately 130.

[0086] Embodiment 14. The hybrid composition of any preceding claim, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a Noack TGA weight loss between approximately 8% and approximately 15%.

[0087] Embodiment 15. The hybrid composition of any preceding claim, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a pour point below -40°C.

[0088] Embodiment 16. The hybrid composition of any preceding claim, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a pour point below -83°C.

[0089] Embodiment 17. A lubricant composition having the hybrid composition of any preceding claim.

[0090] Embodiment 18. A thermal management fluid having the hybrid composition of any preceding claim to form a base fluid.

[0091] Embodiment 19. The hybrid composition of any preceding claim, wherein a ratio of an amount of lightly branched C12 olefins to an amount of linear alpha olefins is approximately 5: 1, 4: 1, 3: 1, 2: 1, 1 :1, 1 :5, 1 :2, 1 :3, 1 :4, or 1 :5.

[0092] Embodiment 20. A method includes providing a butene feedstock. The method also includes optionally providing a propylene feedstock. The method also includes generating higher olefins by contacting the butene feedstock with the propylene feedstock in the presence of a catalyst. The method also includes fractionating the higher olefins to obtain lightly branched C12 olefins. The method also includes generating an oligomer composition by contacting lightly branched C12 olefins with linear alpha olefins of varying lengths in the presence of a catalyst and optionally activators.

[0093] Embodiment 21. The method of the preceding claim, wherein the linear alpha olefin includes C14, Ci6, Cis, or any combination thereof.

[0094] Embodiment 22. The method of any preceding claim, further including hydrogenating the oligomer composition.

[0095] Embodiment 23. The method of any preceding claim, further including fractionating a viscosity range of the oligomer composition from monomers of both lightly branched C12 olefins and linear alpha olefins to obtain hybrid oligomers.

Claims

CLAIMS:

1. An olefin composition, comprising: an average carbon number is between approximately 11.2 and approximately 12.8; and a branching index between approximately 1.0 and approximately 1.9; wherein the olefin composition comprises greater than or equal to 40 wt% of the sum of mono-methyl branched isododecenes and linear dodecenes, and wherein the mono-methyl branched isododecenes comprise one or more of 2-methyl undecene, 3-methyl undecene, 4-methyl undecene, 5 -methyl undecene, and 6-methyl undecene.

2. The olefin composition of claim 1, comprising approximately 40 to approximately 80 wt% of the mono-methyl branched isododecenes and linear dodecene.

3. The olefin composition of claim 2, comprising approximately 5 to approximately 15 wt% of linear dodecene of a total sum of mono-methyl branched isododecenes and linear dodecene.

4. The olefin composition of claim 1, comprising approximately 5 to approximately 20 wt% 2-methyl undecane of a total sum of mono-methyl branched isododecenes and linear dodecene.

5. The olefin composition of claim 1, comprising approximately 10 to approximately 25 wt% 3-methyl undecane of a total sum of mono-methyl branched isododecenes and linear dodecene.

6. The olefin composition of claim 1, comprising approximately 15 to approximately 25 wt% 4-methyl undecane of a total sum of mono-methyl branched isododecenes and linear dodecene.

7. The olefin composition of claim 1, comprising approximately 30 to approximately 55 wt% 5 -methyl undecane, 6-methyl undecane, or both of a total sum of mono-methyl branched isododecenes and linear dodecene.

8. The olefin composition of claim 1 , wherein the olefin composition comprises greater than or equal to 45 wt% of the mono-methyl branched isododecenes and linear dodecene.

9. A hybrid composition produced from a mixture comprising lightly branched C12 olefins and a linear alpha olefin of varying carbon lengths, wherein a linear alpha olefin can be Cs, C10, C12, C14, Ci6, Cis, larger carbons, or any combination thereof, and wherein the lightly branched C12 olefins comprise mono-methyl branched isododecenes.

10. The hybrid composition of claim 9, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins have a kinematic viscosity at 40°C between 9.0 to 20.0 cSt.

11. The hybrid composition of claim 9, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins have a kinematic viscosity at 100°C between 2.0 to 4.5 cSt.

12. The hybrid composition of claim 9, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a viscosity index between approximately 120 and approximately 140.

13. The hybrid composition of claim 9, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a viscosity index is approximately 130.

14. The hybrid composition of claim 9, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a Noack TGA weight loss between approximately 8% and approximately 15%.

15. The hybrid composition of claim 9, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a pour point below -40°C.

16. The hybrid composition of claim 9, wherein the hybrid composition produced from linear alpha olefins and lightly branched C12 olefins has a pour point below -83°C.

17. A lubricant comprising the hybrid composition of claim 9.

18. A thermal management fluid comprising the hybrid composition of claim 9 to form a base fluid.

19. The hybrid composition of claim 9, wherein a ratio of an amount of lightly branched C12 olefins to an amount of linear alpha olefins is approximately 5: 1, 4: 1, 3: 1, 2: 1, 1 : 1, 1 :5, 1 :2, 1 :3, 1 :4, or 1 :5.

20. A method, comprising: providing a butene feedstock; optionally providing a propylene feedstock; generating higher olefins by contacting the butene feedstock with the propylene feedstock in the presence of a catalyst; fractionating the higher olefins to obtain lightly branched C12 olefins; and generating an oligomer composition by contacting lightly branched C12 olefins with linear alpha olefins of varying lengths in the presence of catalyst and optionally activators.

21. The method of claim 20, wherein the linear alpha olefin comprises C14, Ci6, Cis, or any combination thereof.

22. The method of claim 20, further comprising hydrogenating the oligomer composition.

23. The method of claim 20, further comprising fractionating a viscosity range of the oligomer composition from monomers of both lightly branched C12 olefins and linear alpha olefins to obtain hybrid oligomers.

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