Ester blends for electrically driven and cooling applications

Abstract

This disclosure relates to oil compositions of ester blends useful in the chemical field, such as in the manufacture of products (e.g., base oils and battery immersion cooling fluids). In particular, this disclosure relates to blends of alkenyl diesters (e.g., dialkyl fumarate or dialkyl maleate) and compounds of formula I.

Description

[0001] Related applications This application claims the benefit of U.S. Provisional Application No. 63 / 585,036, filed September 25, 2023, the entire disclosure of which is incorporated herein by reference. Background Technology

[0002] Base oils are used in automotive applications such as engine oils, transmission and gear lubricants, and greases. Base oils are typically the main component of engine oils or coolant fluids, along with other additives such as lubricants, corrosion inhibitors, detergents, dispersants, antioxidants, and viscosity modifiers.

[0003] Typical base oils are produced by refining crude oil to separate components of desired viscosity. Therefore, base oils are typically petroleum-based. There is a search for bio-based fluids to provide greener alternatives to base oils while maintaining performance. Compositions comprising bio-based esters (e.g., fatty acid esters based on mineral and vegetable oils) have been proposed.

[0004] Current industry trends focus on low-viscosity fluids that can improve system efficiency while maintaining good lubrication and cooling properties (flash point, evaporation, thermal degradation, electrical conductivity, thermal conductivity, etc.).

[0005] Electrical conductivity is considered in determining the suitability of oil compositions for use as electric drive fluids (EDFs) and / or coolant fluids. Low conductivity is particularly important for fluids used in electric vehicles. For example, oil compositions used in electric motors are designed to provide adequate low conductivity to prevent charge buildup and arcing that could damage hardware. External factors such as temperature, time, and moisture content can alter fluid conductivity. Polar components generated by oxidation will also increase the lubricant's ability to carry charge. For optimal performance, EDFs are expected to provide low and stable conductivity throughout the fluid's operating life.

[0006] Battery thermal management is also considered regarding the suitability of oil compositions for use in electric vehicles (EVs). Cells may need to be kept cool under loads from driving and charging, or warm in cold environments. This allows for more efficient battery operation and improved safety. In some instances, cooling is achieved via a water-cooled plate at the base of the battery pack or via coolant channels between the cells. Immersion cooling is a promising thermal management technique that can increase battery life, but there are certainly obstacles to its adoption. Most people are initially concerned with the weight of the fluid. For example, it is often above 1.5 g / cm³. 3 Heavy hydrofluoroether products with a density lower than that of water (1 g / cm³). However, using other types of dielectric fluids (such as synthetic esters or other oil mixtures) can provide products with a density lower than that of water (1 g / cm³).3 ) fluid.

[0007] Therefore, there is still a need for improved base oil compositions and cooling fluid compositions that target low viscosity and also provide high thermal stability and low electrical conductivity. Summary of the Invention

[0008] In one aspect, this disclosure provides an oil composition comprising (i) a blend of an alkenyl diester and (ii) a compound of formula I or a salt thereof. in R 1 It is an alkyl group. R 2 It is H or acyl, and n, m, and p are each an independent integer of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0009] In another aspect, this disclosure relates to oil compositions comprising a blend of dialkyl fumarate and alkyl castor oil.

[0010] On the other hand, this disclosure provides base oil compositions comprising the oil compositions described herein.

[0011] On the other hand, this disclosure provides a cooling fluid comprising an oil composition as described herein.

[0012] On the other hand, this disclosure provides additives for base oil compositions comprising the oil compositions as described herein.

[0013] In another aspect, this disclosure provides an additive for cooling fluids comprising an oil composition as described herein.

[0014] In another aspect, this disclosure provides a method for cooling an electric drive, which includes adding a composition to the electric drive, said composition comprising an oil composition as described herein.

[0015] In another aspect, this disclosure provides a method for preparing an oil composition blend comprising the composition described herein, comprising: combining an imide diester and a compound of formula I and mixing for at least 5 minutes.

[0016] In another aspect, this disclosure provides a method for preparing an oil composition blend comprising the composition described herein, comprising: combining (i) dialkyl fumarate and (ii) alkyl castor oil ester and mixing for at least 5 minutes.

[0017] Additional embodiments, features, and advantages of this disclosure will become apparent from the following detailed description and through practice. The compounds and methods of this disclosure may be described as embodiments in any of the following enumerated terms. It will be understood that any embodiment described herein may be used in combination with any other embodiment described herein to the extent that the embodiments do not contradict each other.

[0018] Brief description of the attached figures Figure 1 The graphs show the conductivity vs. temperature of different esters and ester blends. Bio-ester A (BA) is methyl ricinoleate A, bio-ester B (BB) is methyl ricinoleate B, synthetic ester A is dioctyl fumarate (DOF), and bio-oil (BO) is castor oil.

[0019] Figure 2 The graphs show the conductivity vs. temperature of different esters and ester blends. Bio-ester B (BB) is methyl ricinoleate B, synthetic ester B is dioctyl maleate (DOM), and synthetic ester C is dibutyl fumarate (DBF).

[0020] Figure 3 The graphs show the conductivity vs. temperature of different esters and ester blends. Synthetic ester A is dioctyl fumarate (DOF), synthetic ester B is dioctyl maleate (DOM), and synthetic ester D is dibutyl maleate (DBM).

[0021] Figure 4 The graphs show the thermal conductivity vs. temperature of different esters and ester blends. Bio-ester A (BA) is methyl ricinoleate A, bio-ester B (BB) is methyl ricinoleate B, synthetic ester A is dioctyl fumarate (DOF), Gr III MO is grade III mineral oil, and the comparative ester (Com. ester) is diisononyl adipate.

[0022] Figure 5 A graph showing the average wear scar diameter (WSD) of different esters and ester blends on a high-frequency reciprocating testing machine (HFRR) is presented. Bio-ester A (BA) is methyl ricinoleate A, bio-ester B (BB) is methyl ricinoleate B, synthetic ester A is dioctyl fumarate (DOF), and the comparative ester (Com. ester) is diisononyl adipate.

[0023] Figure 6 The graph shows the average coefficient of friction (COF) of HFRR for different esters and ester blends. Bio-ester A (BA) is methyl ricinoleate A, bio-ester B (BB) is methyl ricinoleate B, synthetic ester A is dioctyl fumarate (DOF), and the comparative ester (Com. ester) is diisononyl adipate.

[0024] Figure 7A shows images of flocculant formation and separation from an oil composition containing bio-ester A (methyl ricinoleate A).

[0025] Figure 7B shows an illustrative diol present in flocculent material isolated from an oil composition containing bio-ester A (methyl ricinoleate A).

[0026] Figure 7C shows the flocculent material separated from an oil composition containing bio-ester A (methyl ricinoleate A). 1 1H nuclear magnetic resonance (NMR) spectrum (left) and 13 C NMR spectrum (right). Arrows indicate the protons and carbons corresponding to the formation of diols. Detailed Implementation

[0027] Before further describing this disclosure, it should be understood that this disclosure is not limited to the specific embodiments described, as these can certainly vary. It should also be understood that the terminology used herein is for the purpose of describing specific embodiments only and is not intended to be limiting, as the scope of this disclosure will be limited only by the appended terms.

[0028] For the sake of brevity, the disclosures of publications (including patents) cited in this specification are incorporated herein by reference. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. All patents, applications, published applications, and other publications mentioned herein are incorporated herein by reference in their entirety. If a definition set forth in this section is contrary to or otherwise inconsistent with a definition set forth in a patent, application, or other publication incorporated herein by reference, the definition set forth in this section shall prevail over the definition incorporated herein by reference.

[0029] As used herein and in the attached terms, the singular forms “a,” “an,” and “the” include plural referents unless the context clearly provides otherwise. It should also be noted that terms may be drafted to exclude any optional elements. Therefore, this statement is intended to serve as a prior basis for the use of exclusive terms such as “uniquely,” “only,” and similar terms related to elements of the stated terms, or for the use of negative restrictions.

[0030] As used herein, the terms “including,” “containing,” and “comprising” are used in their open, non-restrictive sense.

[0031] To provide a more concise description, some quantitative expressions given herein do not conform to the term "about". It should be understood that, whether or not the term "about" is explicitly used, each quantity given herein is intended to refer to an actual given value, and also to an approximation of this given value that would be reasonably inferred by one of ordinary skill in the art, including equivalents and approximations attributable to experimental and / or measurement conditions for this given value. Whenever a yield is given as a percentage, such yield refers to the mass of the entity giving the yield relative to the maximum amount of the same entity available under specific stoichiometric conditions. Unless otherwise stated, concentrations given as percentages refer to mass ratios.

[0032] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. While any methods and materials similar to or equivalent to those described herein may be used in the practice or testing of this disclosure, preferred methods and materials are described hereafter. All publications referenced herein are incorporated by way of citation to disclose and describe the methods and / or materials in connection with those publications.

[0033] Unless otherwise stated, the methods and techniques of this embodiment are generally performed according to conventional methods known in the art and as described in the various general and more specific references cited and discussed throughout this specification. See, for example, Loudon, Organic Chemistry, 4th ed., New York: Oxford University Press, 2002, pp. 360-361, 1084-1085; Smith and March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed., Wiley-Interscience, 2001.

[0034] The chemical names of the compounds described in this article are typically derived using commercially available ACD / Name 2014 (ACD / Labs) or ChemBioDraw Ultra 13.0 (Perkin Elmer).

[0035] It should be understood that, for clarity, certain features of this disclosure described in the context of individual embodiments may also be provided in combination in a single embodiment. Conversely, for brevity, various features of this disclosure described in the context of individual embodiments may also be provided individually or in any suitable sub-combination. All combinations of embodiments relating to chemical groups represented by variables are specifically covered by this disclosure and are disclosed herein as if each and every combination were disclosed individually and explicitly, to the extent that such combinations cover compounds that are stable compounds (i.e., compounds that can be isolated, characterized, and tested for biological activity). Additionally, all sub-combinations of chemical groups listed in embodiments describing such variables are also specifically covered by this disclosure and are disclosed herein as if each and every sub-combination of such chemical groups were disclosed individually and explicitly herein.

[0036] definition Unless otherwise defined herein, the scientific and technical terms used in this application shall have the meanings commonly understood by one of ordinary skill in the art. Generally, the nomenclature and techniques used in relation to the chemistry, polymer, and materials chemistry described herein are those well-known and commonly used in the art.

[0037] Unless otherwise stated, the methods and techniques disclosed herein are generally performed in accordance with conventional methods known in the art and described in the various general and more specific references cited and discussed throughout this specification.

[0038] Unless otherwise defined herein, chemical terms used herein are used in accordance with their conventional usage in the art, as illustrated in "The McGraw-Hill Dictionary of Chemical Terms", Parker S., Ed., McGraw-Hill, San Francisco, Calif. (1985).

[0039] All of the foregoing and any other publications, patents and published patent applications mentioned in this application are specifically incorporated herein by reference. In case of conflict, this specification, including its specific definitions, shall prevail.

[0040] As used herein, the terms “optional” or “optionally” mean that an event or situation described below may or may not occur, and the description includes instances of the event or situation occurring as well as instances of it not occurring. For example, “optionally substituted alkyl” means that the alkyl group may be substituted as well as that the alkyl group may not be substituted.

[0041] As used herein, the term "salt" or "its salt" is used to refer to the acid addition salt or base addition salt of the compounds of this disclosure. Suitable salt selection will be known to those skilled in the art.

[0042] As used herein, the term "acid addition salt" means any organic or inorganic salt of any basic compound of the present disclosure. Exemplary inorganic acids that form suitable salts include hydrochloric acid, hydrobromic acid, sulfuric acid, and phosphoric acid, as well as metal salts such as sodium monohydrogen phosphate and potassium hydrogen sulfate. Exemplary organic acids that form suitable salts include monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids, such as glycolic acid, lactic acid, pyruvic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, malic acid, tartaric acid, citric acid, ascorbic acid, maleic acid, benzoic acid, phenylacetic acid, cinnamic acid, and salicylic acid, as well as sulfonic acids such as p-toluenesulfonic acid and methanesulfonic acid.

[0043] As used herein, the term "base addition salt" means any organic or inorganic salt of any acid compound of this disclosure. Exemplary inorganic bases that form suitable salts include lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, or barium hydroxide. Exemplary organic bases that form suitable salts include aliphatic organic amines, alicyclic organic amines, or aromatic organic amines, such as methylamine, trimethylamine, and methylpyridine or ammonia.

[0044] In some embodiments, the salts considered in this disclosure include, but are not limited to, alkyl, dialkyl, trialkyl, or tetraalkylammonium salts. In some embodiments, the salts considered in this disclosure include, but are not limited to, the following salts: L-arginine, benenthamine, benzathine, betaine, calcium hydroxide, choline, deanol, diethanolamine, diethylamine, 2-(diethylamino)ethanol, ethanolamine, ethylenediamine, N-methylglucosamine, hydrabamine, 1H-imidazolium, lithium, L-lysine, magnesium, 4-(2-hydroxyethyl)morpholine, piperazine, potassium, 1-(2-hydroxyethyl)pyrrolidine, sodium, triethanolamine, tromethamine, and zinc. In some embodiments, the salts considered in this disclosure include, but are not limited to, Na, Ca, K, Mg, Zn, or other metal salts. In some embodiments, the salts considered in this disclosure include, but are not limited to, the following: 1-hydroxy-2-naphtholic acid, 2,2-dichloroacetic acid, 2-hydroxyethanesulfonic acid, 2-oxoglutaric acid, 4-acetaminobenzoic acid, 4-aminosalicylic acid, acetic acid, adipic acid, 1-ascorbic acid, 1-aspartic acid, benzenesulfonic acid, benzoic acid, (+)-camphoric acid, (+)-camphor-10-sulfonic acid, decanoic acid (decacarbonate), hexanoic acid (hexacarbonate), octanoic acid (octacarbonate), carbonic acid, cinnamic acid, citric acid, cyclopentaenoic acid, and dodecyl groups. Sulfuric acid, ethane-1,2-disulfonic acid, ethanesulfonic acid, formic acid, fumaric acid, galactosic acid, gentic acid, d-glucoheponic acid, d-gluconic acid, d-glucuronic acid, glutamic acid, glutamate, glycerophosphate, glycolic acid, hippuric acid, hydrobromic acid, hydrochloric acid, isobutyric acid, lactic acid, lactobionic acid, lauric acid, maleic acid, 1-malic acid, malonic acid, mandelic acid, methanesulfonic acid, naphthalene-1,5-disulfonic acid, naphthalene-2-sulfonic acid, nicotinic acid, nitric acid, oleic acid, oxalic acid, palmitic acid, pamoic acid, phosphoric acid, propionic acid, L-pyroglutamic acid, salicylic acid, sebacic acid, stearic acid, succinic acid, sulfuric acid, 1-tartaric acid, thiocyanate, p-toluenesulfonic acid, trifluoroacetic acid, and undecanoic acid.

[0045] The term "acyl" is recognized in the art and refers to a group represented by the general formula hydrocarbon C(O)-, preferably alkyl C(O)-. An exemplary acyl group is an acetyl group (i.e., -C(O)CH3).

[0046] The term "alkyl" refers to a monovalent saturated aliphatic group, including straight-chain alkyl groups, branched alkyl groups, cycloalkyl (alicyclic) groups, alkyl-substituted cycloalkyl groups, and cycloalkyl-substituted alkyl groups. The term "alkylene" refers to a straight (i.e., linear) or branched divalent saturated aliphatic group. In a preferred embodiment, the straight (i.e., linear) or branched alkyl or alkylene group has 20 or fewer carbon atoms in its backbone (e.g., for a straight (i.e., linear) chain of C1646). 1-20 For a branch of C3-20 ), and more preferably 12 or less.

[0047] Furthermore, the terms “alkyl” and “alkylene” as used throughout the specification, examples and claims are intended to include both unsubstituted and substituted alkyl and alkylene groups, the latter referring to an alkyl or alkylene portion having a substituent replacing hydrogen on one or more carbons of the hydrocarbon backbone, including haloalkyl groups such as trifluoromethyl and 2,2,2-trifluoroethyl.

[0048] The term "alkenyl" refers to a monovalent, straight-chain or branched hydrocarbon group having one or more double bonds. The term "alkenylene" refers to a divalent, straight-chain or branched hydrocarbon group having one or more double bonds. In some embodiments, it may be advantageous to limit the number of atoms in "alkenyl" or "alkenylene" to a specific atomic range, such as C2-C. 20 alkenyl or alkenyl, C2-C 12 Alkenyl or alkenyl, or C2-C6 alkenyl or alkenyl. Examples of alkenyl groups include vinyl (or vinyl), allyl, and but-3-en-1-yl. These terms include cis (E) and trans (Z) isomers and mixtures thereof. The double bond of the alkenyl or alkenyl group can be formed by the structure " "or" This indicates that the structure "" represents the meaning of the sentence. It should be understood that this is due to the structure "" The double bond indicated by "" can represent an unspecified cis or trans configuration, or a mixture of cis and trans configurations. It should be understood that the alkenyl or alkenyl group can be unsubstituted or substituted as described herein. The alkenyl or alkenyl group can be substituted with any substituent in the various embodiments described herein, including one or more such substituents. For example, the alkenyl group can be substituted with an ester group to provide an alkenyl ester. It should be understood that the term "alkenyl diester" refers to an alkenyl group substituted with two ester groups. For example, an alkenyl diester can be depicted using the following structural formula: .

[0049] As used herein, the term "blend" refers to a mixture of two or more components. Blends or mixtures can be homogeneous or heterogeneous. A homogeneous mixture is a composition that is uniform throughout the mixture. A heterogeneous mixture is a composition comprising two or more phases. For example, a heterogeneous mixture includes regions that have properties different from those of another region, even if they are in the same physical state (e.g., liquid or solid).

[0050] As used herein, the term "bio-oil" refers to an oil that is not petroleum-based, such as mineral oil, vegetable oil, or any suitable oil derived from a biological source. A non-limiting example of a bio-oil is castor oil.

[0051] As used herein, the term "bio-based ester" or "bio-ester" refers to a fatty acid ester derived from a bio-oil. For example, alkyl ricinoleate is a fatty acid ester derived from castor oil, which may include ricinoleic acid.

[0052] When used in conjunction with a chemical moiety (such as an alkyl group), the term "C" is used. x-y "or "C x -C y "This is intended to include groups containing carbons from x to y in the chain. C0 alkyl indicates that the group is hydrogen at the terminal position or a bond if it is internal. For example, C..." 1-6 Alkyl groups contain one to six carbon atoms in the chain.

[0053] As used herein, the term "ester" refers to a group or -C(O)O alkyl group or -C(O)OR group. 8 , where R 8 The alkyl group represents a hydrocarbon group, preferably an alkyl group, and the alkyl group can be C1-C. 15 Alkyl, C2-C 12 Alkyl or C1-C6 alkyl.

[0054] As used herein, the terms “flocculant” or “flock” refer to agglomerated clumps of high-melting-point particles that separate from the liquid phase at ambient temperature. For example, the formation and / or presence of diols in an oil composition (e.g., diols present in bio-esters) may lead to floc formation.

[0055] As used herein, the term "hydrocarbon group" refers to a carbon-atom-bonded group that does not have a =O or =S substituent and typically has at least one carbon-hydrogen bond and a major carbon skeleton, but may optionally include heteroatoms. Therefore, for the purposes of this application, groups such as methyl, ethoxyethyl, 2-pyridyl, and even trifluoromethyl are considered hydrocarbon groups, but substituents such as acetyl (which has a =O substituent on the linking carbon) and ethoxy (which is linked by oxygen rather than carbon) are not. Hydrocarbon groups include, but are not limited to, aryl, heteroaryl, carbocyclic, heterocyclic, alkyl, alkenyl, ynyl, and combinations thereof.

[0056] As used herein, the terms "synthetic-based ester" or "synthetic ester" refer to an ester that has been chemically synthesized. For example, dialkyl fumarate and dialkyl maleate can be synthetic esters. A non-limiting example of a commercially available synthetic-based ester is the Esterex from ExxonMobil. TM A34 (diisononyl adipate).

[0057] As used herein, the terms “Group II base oil” or “Group II mineral oil” refer to petroleum-derived oils with a saturation content greater than 90%, a sulfur content less than 0.03%, and a viscosity index of 80 to 120. A non-limiting example of a Group II mineral oil is Chevron Neutral Oil (100R) purchased from Chevron.

[0058] As used herein, the terms “Group III base oil” or “Group III mineral oil” refer to petroleum-derived oils with a saturation content greater than 90%, a sulfur content less than 0.03%, and a viscosity index greater than 120. A non-limiting example of a Group III mineral oil is TS-VHVI 4, available from Tulstar Products, Inc.

[0059] Representative Implementation Plan In some embodiments, this disclosure relates to an oil composition comprising a blend of an alkenyl diester and a compound of formula I or a salt thereof. in R 1 It is an alkyl group. R 2 It is H or acyl, and n, m, and p are each an independent integer of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0060] In some embodiments, this disclosure relates to an oil composition comprising a blend of dialkyl fumarate and alkyl castor oil.

[0061] In some embodiments, this disclosure relates to base oil compositions comprising the oil compositions described herein. In some embodiments, this disclosure relates to base oil compositions comprising blends of alkenyl diesters and compounds of formula I. In some embodiments, this disclosure relates to base oil compositions comprising blends of dialkyl fumarate and alkyl ricinoleate. In some embodiments, the base oil is an automotive oil (i.e., an automotive base oil). In some embodiments, the base oil is a coolant (e.g., an automotive coolant and / or a submersible coolant).

[0062] In some embodiments, this disclosure relates to automotive oils (i.e., automotive base oils) comprising the oil compositions described herein. In some embodiments, this disclosure relates to automotive oils (i.e., automotive base oils) comprising blends of an alkenyl diester and a compound of formula I. In some embodiments, this disclosure relates to automotive oils (i.e., automotive base oils) comprising blends of a dialkyl fumarate and an alkyl ricinoleate.

[0063] In some embodiments, this disclosure relates to cooling fluids comprising the oil compositions described herein (e.g., automotive cooling fluids and / or immersion cooling fluids). In some embodiments, this disclosure relates to cooling fluids comprising blends of alkenyl diesters and compounds of Formula I (e.g., automotive cooling fluids and / or immersion cooling fluids). In some embodiments, the cooling fluid is an immersion cooling fluid. In some embodiments, the cooling fluid is a battery immersion cooling fluid or a data center hardware immersion cooling fluid. In some embodiments, this disclosure relates to cooling fluids comprising blends of dialkyl fumarate and alkyl castor oil (e.g., automotive cooling fluids and / or immersion cooling fluids).

[0064] In some embodiments, this disclosure relates to additives comprising the oil compositions described herein. In some embodiments, this disclosure relates to additives comprising blends of an allylene diester and a compound of formula I. In some embodiments, this disclosure relates to additives comprising blends of a dialkyl fumarate and an alkyl castor oil ester.

[0065] In some embodiments, this disclosure relates to additives for automotive oil (i.e., automotive base oil) compositions comprising the oil compositions described herein. In some embodiments, this disclosure relates to additives for automotive base oil compositions comprising blends of an allyl diester and a compound of formula I. In some embodiments, this disclosure relates to additives for automotive base oil compositions comprising blends of dialkyl fumarate and alkyl ricinoleate. In some embodiments, this disclosure relates to additives for automotive oil compositions comprising blends of dialkyl fumarate and alkyl ricinoleate.

[0066] In some embodiments, this disclosure relates to additives for cooling fluid (e.g., automotive cooling fluids and / or immersion cooling fluids) compositions comprising the oil compositions described herein. In some embodiments, this disclosure relates to additives for cooling fluid (e.g., automotive cooling fluids and / or immersion cooling fluids) compositions comprising blends of an alkenyl diester and a compound of formula I. In some embodiments, the cooling fluid is an immersion cooling fluid. In some embodiments, the cooling fluid (e.g., an immersion cooling fluid) is a battery immersion cooling fluid or a data center hardware immersion cooling fluid. In some embodiments, this disclosure relates to additives for cooling fluid (e.g., automotive cooling fluids and / or immersion cooling fluids) compositions comprising blends of dialkyl fumarate and alkyl ricinoleate. In some embodiments, this disclosure relates to additives for cooling fluid (e.g., automotive cooling fluids and / or immersion cooling fluids) compositions comprising blends of dialkyl fumarate and alkyl ricinoleate.

[0067] In some embodiments, this disclosure relates to a method of cooling an electric drive, which includes adding a composition to the electric drive. In some embodiments, this disclosure relates to a method of cooling an electric drive, which includes adding an oil composition described herein to the electric drive. For example, the electric drive (drivetrain) may include one or more components, such as a battery, power electronics, an e-axis, an electric motor, etc. In some embodiments, the composition added to the electric drive comprises a blend of an alkenyl diester and a compound of formula I. In some embodiments, the adding step includes immersing one or more components of the electric drive (e.g., a battery) in the oil composition. In some embodiments, the composition added to the electric drive comprises a blend of a dialkyl fumarate and an alkyl castor oil ester.

[0068] In some implementations, the cooling fluid is an immersion cooling fluid. In some implementations, the cooling fluid is a battery immersion cooling fluid or a data center hardware immersion cooling fluid.

[0069] In some embodiments, this disclosure relates to a method of cooling a data center (e.g., data center hardware), which includes adding a composition to the data center. In some embodiments, this disclosure relates to a method of cooling a data center, which includes adding the oil composition described herein to the data center. In some embodiments, the composition added to the data center comprises a blend of an alkenyl diester and a compound of formula I. In some embodiments, the adding step includes immersing one or more components of the data center in the oil composition. In some embodiments, the composition added to the data center comprises a blend of a dialkyl fumarate and an alkyl castor oil ester.

[0070] In some embodiments, this disclosure relates to methods for preparing oil composition blends comprising the oil compositions described herein. For example, the oil composition may be a base oil, such as an automotive oil (e.g., an automotive base oil) and / or a coolant (e.g., a submersible coolant). In some embodiments, this disclosure relates to methods for preparing oil composition blends comprising a blend of an alkenyl diester and a compound of formula I. In some embodiments, this disclosure relates to methods for preparing oil composition blends comprising a dialkyl fumarate and an alkyl ricinoleate. In some embodiments, this disclosure relates to methods for preparing automotive oil (i.e., automotive base oil) composition blends comprising a blend of a dialkyl fumarate and an alkyl ricinoleate.

[0071] In some embodiments, the method of preparing an oil composition blend includes combining an alkenyl diester and a compound of formula I. In some embodiments, the method of preparing an oil composition blend includes combining an alkenyl diester and a compound of formula I and mixing for at least 5 minutes. In some embodiments, the method of preparing an oil composition blend includes combining an alkenyl diester and a compound of formula I to provide a mixture and mixing the mixture for at least 5 minutes to provide a blend. For example, the mixing may be for at least about 10 minutes, at least about 15 minutes, at least about 20 minutes, at least about 25 minutes, or at least about 30 minutes. In some embodiments, the method of preparing an oil composition blend includes combining an alkenyl diester and a compound of formula I and mixing for about 5 minutes to about 1 hour. For example, the mixing may be for about 10 minutes to about 1 hour, about 15 minutes to about 1 hour, about 5 minutes to about 45 minutes, about 10 minutes to about 45 minutes, or about 15 minutes to about 45 minutes.

[0072] In some embodiments, the alkenyl diester is based on a synthetic ester (synthetic ester). In some embodiments, the compound of formula I is based on a biological ester (bio-ester). In some embodiments, this disclosure relates to an oil composition comprising a blend of a biologically based ester (bio-ester) and a synthetically based ester (synthetic ester).

[0073] In some embodiments, the oil composition comprises a blend of an alkenyl diester and an alkyl ester of castor oil, the alkenyl diester including an alkyl ester of fumarate (e.g., dialkyl fumarate), an alkyl ester of maleate (e.g., dialkyl maleate), or a combination thereof. In some embodiments, the oil composition comprises a blend of an alkenyl diester and a compound of formula I, the alkenyl diester including an alkyl ester of fumarate (e.g., dialkyl fumarate), an alkyl ester of maleate (e.g., dialkyl maleate), or a combination thereof.

[0074] In some embodiments, the compound (e.g., a bio-based ester) has formula I: or its salt, wherein R 1 It is an alkyl group. R 2 It is an H or acyl group. n, m, and p are each an independent integer of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0075] In some implementations, n is an integer of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. For example, n can be an integer of 2, 3, 4, 5, 6, 7, 8, 9, or 10; n can be an integer of 4, 5, 6, 7, 8, 9, or 10; n can be an integer of 6, 7, 8, or 10; n can be an integer of 2, 3, 4, 5, 6, 7, or 8; n can be an integer of 4, 5, 6, 7, or 8; or n can be an integer of 6, 7, or 8. In some preferred implementations, n is 7.

[0076] In some implementations, m is an integer of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. For example, m can be an integer of 1, 2, 3, 4, 5, 6, 7, or 8; m can be an integer of 1, 2, 3, 4, 5, or 6; m can be an integer of 1, 2, 3, or 4; or m can be 1 or 2. In some preferred implementations, m is 1.

[0077] In some implementations, p is an integer of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. For example, p can be an integer of 2, 3, 4, 5, 6, 7, 8, or 9; p can be an integer of 3, 4, 5, 6, 7, or 8; p can be an integer of 3, 4, 5, or 6; p can be an integer of 4, 5, 6, or 7; or p can be an integer of 4, 5, or 6. In some preferred implementations, p is 5.

[0078] In some embodiments, the compound of formula I is an alkyl ricinoleate or a trans-alkyl ricinoleate. In some embodiments, the compound of formula I is an alkyl ricinoleate. In some embodiments, the alkyl ricinoleate is a C1-C6 alkyl ricinoleate. In some embodiments, the alkyl ricinoleate is a C1-C3 alkyl ricinoleate. In some preferred embodiments, the alkyl ricinoleate is methyl ricinoleate. In some embodiments, the compound of formula I is a trans-alkyl ricinoleate. In some embodiments, the trans-alkyl ricinoleate is a C1-C6 alkyl ricinoleate. In some embodiments, the trans-alkyl ricinoleate is a C1-C3 alkyl ricinoleate. In some embodiments, the trans-alkyl ricinoleate is methyl ricinoleate.

[0079] In some embodiments, the compound of formula I is methyl ricinoleate (i.e., R... 1 It is methyl) or trans-ricinoleate methyl ester (i.e., R 1 It is methyl). In some embodiments, the compound of formula I (e.g., alkyl ricinoleate) is methyl ricinoleate (i.e., R 1 It is methyl). In some embodiments, the compound of formula I (e.g., alkyl trans-ricinoleate) is methyl trans-ricinoleate (i.e., R... 1 (It is methyl).

[0080] In some embodiments, the compound of formula I has formula II: or its salt, wherein R 1 It is an alkyl group (e.g., C1-C6 alkyl), and R 2 It is an H or acyl group (e.g., C1-C6 acyl group).

[0081] In some embodiments, the compound of formula I has formula IIa: or its salt, wherein R 1 It is an alkyl group (e.g., C1-C6 alkyl), and R 2 It is an H or acyl group (e.g., C1-C6 acyl group).

[0082] In some embodiments, the compound of formula I has formula IIb: or its salt, wherein R 1 It is an alkyl group (e.g., C1-C6 alkyl), and R 2 It is an H or acyl group (e.g., C1-C6 acyl group).

[0083] In some embodiments, the compound of formula I (e.g., compounds of formulas II, IIa, IIb, II-1, IIa-1, or IIb-1) is a mixture of the first and second compounds. In some embodiments, the compound of formula I is a mixture of the first compound of formula I and the second compound of formula I. In some embodiments, the compound of formula I is a mixture of the first compound of formula IIa (e.g., alkyl ricinoleate) and the second compound of formula IIb (e.g., alkyl transricinoleate).

[0084] In some embodiments, the compound of formula I has formula II-1: or its salt, wherein R 2 It is an H or acyl group (e.g., C1-C6 acyl group).

[0085] In some embodiments, the compound of formula I has formula IIa-1: or its salt, wherein R 2 It is an H or acyl group (e.g., C1-C6 acyl group).

[0086] In some embodiments, the compound of formula I has formula IIb-1: or its salt, wherein R 2 It is an H or acyl group (e.g., C1-C6 acyl group).

[0087] In some implementation schemes, R 1 It is an alkyl group (e.g., C1-C6 alkyl). In some embodiments, R 1 It is methyl, ethyl, or propyl, and preferably methyl.

[0088] In some implementation schemes, R 2 It is an H or acyl group. In some embodiments, R 2 It is H. In some implementations, R 2 It is an H or C1-C6 acyl group (e.g., C(O)C1-C6 alkyl). In some embodiments, R 2 It is an H or C1-C3 acyl group (e.g., C(O)C1-C3 alkyl). In some embodiments, R 2 It is either H or acetyl. In some implementations, R 2 It is a C1-C6 acyl group (e.g., C(O)C1-C6 alkyl). In some embodiments, R 2 It is a C1-C3 acyl group (e.g., C(O)C1-C3 alkyl). In some preferred embodiments, R 2 It is an acetyl group.

[0089] In some embodiments, the compound of formula I (e.g., compounds of formula II, IIa, IIb, II-1, IIa-1, or IIb-1) is selected from the following compounds:

[0090] In some embodiments, compounds of formula I (e.g., compounds of formulas II, IIa, IIb, II-1, IIa-1, or IIb-1) include unprotected alcohols (i.e., R...). 2 (H) or protected alcohols (i.e., R) 2 (Not H, such as acyl). For example, a protected alcohol can be esterified (i.e., acylated) to form an acyl-protected alcohol (i.e., an alkyl ester). In some embodiments, it is advantageous to protect the alcohol group in a compound of formula I (e.g., compounds of formula II, IIa, IIb, II-1, IIa-1, or IIb-1) to improve the shelf life of the oil composition. For example, including a protected alcohol (i.e., an acyl R). 2Compounds of formula I (e.g., compounds of formula II, IIa, IIb, II-1, IIa-1 or IIb-1) can improve the stability of compounds of formula I (e.g., compounds of formula II, IIa, IIb, II-1, IIa-1 or IIb-1) in oil compositions and / or minimize or prevent the formation of flocculent material in oil compositions.

[0091] In some embodiments, the compounds of formula I (e.g., compounds of formulas II, IIa, IIb, II-1, IIa-1, or IIb-1) are of the type of fatty acid esters synthesized from castor oil and alkyl alcohols. For example, methyl ricinoleate is a type of fatty acid methyl ester synthesized from castor oil and methanol.

[0092] In some embodiments, the alkenyl diester is an alkyl fumarate (e.g., dialkyl fumarate), an alkyl maleate (e.g., dialkyl maleate), or a combination thereof. In some embodiments, the alkenyl diester is a combination of one or more alkyl fumarates (e.g., dialkyl fumarate), one or more alkyl maleates (e.g., dialkyl maleate), or a combination thereof. In some embodiments, the alkenyl diester is a combination of a first alkenyl diester (e.g., dialkyl fumarate or dialkyl maleate) and a second alkenyl diester (e.g., dialkyl fumarate or dialkyl maleate). In some embodiments, the alkenyl diester is a combination of dialkyl fumarate and dialkyl maleate. In some embodiments, the alkenyl diester is a combination of a first dialkyl maleate (e.g., dioctyl maleate) and a second dialkyl maleate (e.g., dibutyl maleate). In some embodiments, the alkenyl diester is a combination of a first dialkyl fumarate (e.g., dioctyl fumarate) and a second dialkyl fumarate (e.g., dibutyl fumarate).

[0093] In some embodiments, the synthesized ester (e.g., an alkenyl diester) has Formula III: in R 3 R 4 R 5 and R 6 Each can be an H or an ester independently. The conditions are: R 3 and R 4 One of them is H, and R 3 and R 4 Another one is ester, and R 5 and R 6 One of them is H, and R 5 and R 6Another one is an ester.

[0094] In some implementation schemes, R 3 and R 5 Each of them is H, and R 4 and R 6 Each of these is an ester (e.g., -C(O)O alkyl). In some embodiments, R 3 and R 6 Each of them is H, and R 4 and R 5 Each of them is an ester. In some implementations, R 3 With R 5 Same, and R 4 With R 6 Same. In some implementations, R 3 With R 6 Same, and R 4 With R 5 same.

[0095] In some implementation schemes, R 3 and R 5 Each of these is H. In some implementations, R 4 and R 6 Each of these is an ester (e.g., -C(O)O alkyl). In some embodiments, R 4 and R 6 Each of them is -C(O)OC2-C 12 Alkyl group. For example, R 4 and R 6 Each of them can be -C(O)OC4-C8 alkyl, -C(O)OC6-C 12 Alkyl or -C(O)OC2-C6 alkyl. In some embodiments, R 4 and R 6 Each of them is a -C(O)OC4 alkyl group. In some embodiments, R 4 and R 6 Each of them is a -C(O)OC8 alkyl group.

[0096] In some implementation schemes, R 3 and R 6 Each of them is H. In some implementations, R 4 and R 5 Each of these is an ester (e.g., -C(O)O alkyl). In some embodiments, R 4 and R 5 Each of them is -C(O)OC2-C 12 Alkyl group. For example, R 4 and R5 Each of them can be -C(O)OC4-C8 alkyl, -C(O)OC6-C 12 Alkyl, or -C(O)OC2-C6 alkyl. In some embodiments, R 4 and R 5 Each of them is a -C(O)OC4 alkyl group. In some embodiments, R 4 and R 5 Each of them is a -C(O)OC8 alkyl group.

[0097] In some embodiments, the alkenyl diester has formula IV: Each R is an alkyl group (e.g., C2-C). 12 alkyl).

[0098] In some embodiments, each R is a straight (i.e., linear) alkyl chain or a branched alkyl chain, and preferably a straight-chain alkyl chain. In some embodiments, each R is C2-C. 12 Alkyl group. For example, each R can be a C4-C8 alkyl group, C6-C6 alkyl group, or C6-C6 alkyl group. 12 Alkyl or C2-C6 alkyl. In some embodiments, each R is butyl (C4). In some embodiments, each R is octyl (C8).

[0099] In some embodiments, the alkenyl diester is a dialkyl fumarate. In some embodiments, the alkenyl diester has formula IVa: Each R 7 It is an alkyl group (e.g., C2-C). 12 alkyl).

[0100] In some implementations, each R 7 It is a straight (i.e., linear) alkyl chain or a branched alkyl chain, and preferably a straight-chain alkyl chain. In some embodiments, each R 7 It is C2-C 12 Alkyl groups. For example, each R 7 It can be C4-C8 alkyl, C6-C 12 Alkyl or C2-C6 alkyl. In some embodiments, R 7 It is butyl (C4). In some implementations, each R 7 It is octyl (C8).

[0101] In some embodiments, the dialkyl fumarate is a di(C2-C) fumarate. 12Alkyl ester. In some embodiments, the dialkyl fumarate is a di(C4-C8) fumarate. In some embodiments, the dialkyl fumarate is a di(C6-C8) fumarate. 12 Alkyl ester. In some embodiments, the dialkyl fumarate is a di(C2-C6) alkyl fumarate. In some embodiments, each alkyl chain in the dialkyl fumarate is identical. In some embodiments, each alkyl chain in the dialkyl fumarate is C8 alkyl. In some embodiments, each alkyl chain in the dialkyl fumarate is C6 alkyl. In some embodiments, each alkyl chain in the dialkyl fumarate is C4 alkyl. In some embodiments, each alkyl chain in the dialkyl fumarate is independently branched or straight-chain. In some preferred embodiments, each alkyl chain in the dialkyl fumarate is straight-chain.

[0102] In some implementations, the dialkyl fumarate is: .

[0103] In some implementations, the dialkyl fumarate is: .

[0104] In some embodiments, the alkenyl diester is a dialkyl maleate ester. In some embodiments, the alkenyl diester has formula IVb: Each R 8 It is an alkyl group (e.g., C2-C). 12 alkyl).

[0105] In some implementations, each R 8 It is a straight (i.e., linear) alkyl chain or a branched alkyl chain, preferably a straight-chain alkyl chain. In some embodiments, each R 8 It is C2-C 12 Alkyl groups. For example, each R 8 It can be C4-C8 alkyl, C6-C 12 Alkyl or C2-C6 alkyl. In some embodiments, R 8 It is butyl (C4). In some implementations, each R 8 It is octyl (C8).

[0106] In some implementations, the dialkyl maleate is a di(C2-C) maleate. 12 Alkyl ester. In some embodiments, the dialkyl maleate is a di(C4-C8) maleate. In some embodiments, the dialkyl maleate is a di(C6-C8) maleate. 12Alkyl esters. In some embodiments, the dialkyl maleate is a di(C2-C6) alkyl maleate. In some embodiments, each alkyl chain in the dialkyl maleate is identical. In some embodiments, each alkyl chain in the maleate fumarate is C8 alkyl. In some embodiments, each alkyl chain in the dialkyl maleate is C6 alkyl. In some embodiments, each alkyl chain in the dialkyl maleate is C4 alkyl. In some embodiments, each alkyl chain in the dialkyl maleate is independently branched or straight-chain. In some preferred embodiments, each alkyl chain in the dialkyl maleate is straight-chain.

[0107] In some implementations, the dialkyl maleate is: .

[0108] In some implementations, the dialkyl maleate is: .

[0109] In some embodiments, the alkenyl diester is selected from:

[0110] In some embodiments, dialkyl fumarate can be produced by reacting fumaric acid with two equivalents of an alkyl alcohol. For example, dioctyl fumarate can be produced by reacting fumaric acid with two equivalents of octanol. An acidic catalyst can be used, and water is the byproduct. Fumaric acid can be produced by isomerization of maleic anhydride or by fermentation of glucose.

[0111] In some embodiments, dialkyl maleate can be produced by reacting maleic anhydride with two equivalents of alkyl alcohol. For example, dioctyl maleate can be produced by reacting maleic anhydride with two equivalents of octanol. An acidic catalyst can be used, and water is the byproduct.

[0112] In some embodiments, the alkenyl diester and the compound of formula I are present in the composition at a ratio of about 10:1 to about 1:10. For example, the alkenyl diester and the compound of formula I may be present in the composition at a ratio of about 9:1 to about 1:9, about 8:1 to about 1:8, about 7:1 to about 1:7, about 6:1 to about 1:6, about 5:1 to about 1:5, about 4:1 to about 1:4, about 3:1 to about 1:3, or about 2:1 to about 1:2. In some embodiments, the alkenyl diester and the compound of formula I are present in the composition at a ratio of about 3:1. In some embodiments, the alkenyl diester and the compound of formula I are present in the composition at a ratio of about 1:1. In some embodiments, the oil composition consists of an alkylene diester and a compound of formula I at a ratio of about 3:1. In some embodiments, the oil composition consists of an alkylene diester and a compound of formula I at a ratio of about 1:1.

[0113] In some embodiments, the oil composition comprises a compound of formula I, a first alkenyl diester (e.g., dioctyl maleate), and a second alkylene diester (e.g., dibutyl maleate), wherein the first alkenyl diester and the second alkenyl diester are present in a ratio of about 20:1 to about 1:1. For example, the first alkenyl diester and the second alkylene diester may be present in an oil composition comprising the first alkenyl diester, the second alkylene diester, and the compound of formula I in a ratio of about 15:1 to about 1:1, about 12:1 to about 1:1, about 10:1 to about 1:1, about 9:1 to about 1:1, about 8:1 to about 1:1, about 7:1 to about 1:1, about 6:1 to about 1:1, about 5:1 to about 1:1, about 4:1 to about 1:1, about 15:1 to about 4:1, about 12:1 to about 4:1, or about 10:1 to about 4:1. In some embodiments, the first alkenyl diester and the second alkylene diester are present in an oil composition comprising the first alkenyl diester, the second alkylene diester, and a compound of formula I at a ratio of about 6.5:1.

[0114] In some embodiments, dialkyl fumarate and alkyl ricinoleate are present in the composition at a ratio of about 10:1 to about 1:10. In some embodiments, dialkyl fumarate and alkyl ricinoleate are present in the composition at a ratio of about 5:1 to about 1:5. In some embodiments, dialkyl fumarate and alkyl ricinoleate are present in the composition at a ratio of about 4:1 to about 1:4. In some embodiments, dialkyl fumarate and alkyl ricinoleate are present in the composition at a ratio of about 3:1 to about 1:3. In some embodiments, dialkyl fumarate and alkyl ricinoleate are present in the composition at a ratio of about 2:1 to about 1:2. In some embodiments, dialkyl fumarate and alkyl ricinoleate are present in the composition at a ratio of about 1:1.

[0115] In some embodiments, dialkyl maleate and alkyl ricinoleate are present in the composition at a ratio of about 10:1 to about 1:10. In some embodiments, dialkyl maleate and alkyl ricinoleate are present in the composition at a ratio of about 5:1 to about 1:5. In some embodiments, dialkyl maleate and alkyl ricinoleate are present in the composition at a ratio of about 4:1 to about 1:4. In some embodiments, dialkyl maleate and alkyl ricinoleate are present in the composition at a ratio of about 3:1 to about 1:3. In some embodiments, dialkyl maleate and alkyl ricinoleate are present in the composition at a ratio of about 2:1 to about 1:2. In some embodiments, dialkyl maleate and alkyl ricinoleate are present in the composition at a ratio of about 1:1.

[0116] In some embodiments, the first alkenyl diester (e.g., dioctyl maleate), the second alkylene diester (e.g., dibutyl maleate), and the compound of formula I are present in the composition in a ratio of about 2:1:1 to about 10:1:5. In some embodiments, the first alkenyl diester (e.g., dioctyl maleate), the second alkylene diester (e.g., dibutyl maleate), and the compound of formula I are present in the composition in a ratio of about 6.5:1:2.5.

[0117] In some embodiments, the oil compositions described herein (e.g., bio-based esters and blends) exhibit excellent thermal conductivity, a key parameter for high cooling efficiency. Binary blends possess high flash points and high oxidation stability, critical requirements for use as lubricant base oils and cooling fluids exhibiting high dielectric properties.

[0118] In some embodiments, the low viscosity of the oil compositions described herein (e.g., ester blends) provides a high thermal conductivity value suitable for cooling. The natural corrosion inhibition and lubricity of esters may mean that some other additives can be reduced in dosage. In some embodiments, the oil compositions described herein may contain advantageous properties such as better thermal properties and higher efficiency (e.g., longer battery life, better fuel efficiency). In some embodiments, it may be advantageous to achieve improved thermal properties and higher efficiency through low-viscosity ester blends (e.g., blends of bio-based esters and synthetic esters).

[0119] In some embodiments, the oil composition described herein has a flash point greater than about 140°C. For example, the oil composition may have a flash point greater than about 145°C, greater than about 150°C, greater than about 155°C, greater than about 160°C, greater than about 165°C, greater than about 170°C, greater than about 175°C, greater than about 180°C, greater than about 185°C, or greater than about 190°C. In some embodiments, the oil composition has a flash point from about 140°C to about 200°C. For example, the oil composition may have a flash point from about 145°C to about 200°C, from about 150°C to about 200°C, from about 155°C to about 200°C, from about 160°C to about 200°C, from about 165°C to about 200°C, from about 170°C to about 200°C, from about 175°C to about 200°C, from about 180°C to about 200°C, from about 185°C to about 200°C, or from about 190°C to about 200°C. It should be understood that the flash point of an oil composition can be measured using the ASTM D93 test standard.

[0120] In some embodiments, the oil composition described herein has a viscosity (KV100) of less than about 3 cSt. For example, the oil composition may have a viscosity (KV100) of less than about 2.9 cSt, less than about 2.8 cSt, less than about 2.7 cSt, less than about 2.6 cSt, less than about 2.5 cSt, less than about 2.4 cSt, less than about 2.3 cSt, less than about 2.2 cSt, less than about 2.1 cSt, or less than about 2.0 cSt. In some embodiments, the oil composition has a viscosity (KV100) of from about 0.9 cSt to about 3.0 cSt. For example, the oil composition may have a viscosity (KV100) of about 0.9 cSt to about 2.9 cSt, about 0.9 cSt to about 2.8 cSt, about 0.9 cSt to about 2.7 cSt, about 0.9 cSt to about 2.6 cSt, about 0.9 cSt to about 2.5 cSt, about 0.9 cSt to about 2.4 cSt, about 0.9 cSt to about 2.3 cSt, about 0.9 cSt to about 2.2 cSt, about 0.9 cSt to about 2.1 cSt, or about 0.9 cSt to about 2.0 cSt. It should be understood that the viscosity of the oil composition can be measured using the ASTM D445 test standard.

[0121] In some embodiments, the oil composition described herein has a viscosity (KV40) of less than about 15 cSt. For example, the oil composition may have a viscosity (KV40) of less than about 14 cSt, less than about 13 cSt, less than about 12 cSt, less than about 11 cSt, less than about 10 cSt, less than about 9 cSt, less than about 8 cSt, less than about 7 cSt, less than about 6 cSt, or less than about 5 cSt. In some embodiments, the oil composition has a viscosity (KV40) of less than about 10.0 cSt, less than about 9.9 cSt, less than about 9.8 cSt, less than about 9.7 cSt, less than about 9.6 cSt, less than about 9.5 cSt, less than about 9.4 cSt, less than about 9.3 cSt, less than about 9.2 cSt, less than about 9.1 cSt, less than about 9.0 cSt, less than about 8.9 cSt, less than about 8.8 cSt, less than about 8.7 cSt, less than about 8.6 cSt, less than about 8.5 cSt, less than about 8.4 cSt, less than about 8.3 cSt, less than about 8.2 cSt, less than about 8.1 cSt, or less than about 8.0 cSt. In some embodiments, the oil composition has a viscosity (KV40) of from about 3 cSt to about 15 cSt. For example, the oil composition may have a viscosity (KV40) of about 3 cSt to about 14 cSt, about 3 cSt to about 13 cSt, about 3 cSt to about 12 cSt, about 3 cSt to about 11 cSt, about 3 cSt to about 10 cSt, about 5 cSt to about 15 cSt, about 5 cSt to about 14 cSt, about 5 cSt to about 13 cSt, about 5 cSt to about 12 cSt, about 5 cSt to about 11 cSt, or about 5 cSt to about 10 cSt. It should be understood that the viscosity of the oil composition can be measured using the ASTM D445 test standard.

[0122] In some embodiments, the oil compositions described herein have a conductivity of less than about 100 nS / m. For example, the oil compositions may have a conductivity of less than about 90 nS / m, less than about 80 nS / m, less than about 70 nS / m, less than about 60 nS / m, less than about 50 nS / m, less than about 40 nS / m, or less than about 30 nS / m. It should be understood that the conductivity of the oil compositions can be measured using the DIN EN 51 111 test standard.

[0123] In some embodiments, the oil composition described herein has a conductivity of less than about 100 nS / m when measured in the range of about 20°C to about 150°C. For example, when measured in the range of about 20°C to about 150°C, the oil composition may have a conductivity of less than about 90 nS / m, less than about 80 nS / m, less than about 75 nS / m, less than about 70 nS / m, less than about 60 nS / m, less than about 50 nS / m, less than about 40 nS / m, less than about 30 nS / m, less than about 25 nS / m, less than about 20 nS / m, or less than about 15 nS / m. In some embodiments, the oil composition has a conductivity of less than about 25 nS / m when measured in the range of about 20°C to about 150°C.

[0124] In some embodiments, the oil composition described herein has a conductivity of less than about 40 nS / m when measured in the range of about 20°C to about 150°C. For example, the oil composition may have a conductivity of less than about 25 nS / m when measured in the range of about 20°C to about 140°C, about 20°C to about 120°C, about 20°C to about 120°C, about 20°C to about 110°C, or about 20°C to about 100°C.

[0125] In some embodiments, the oil composition described herein has a conductivity of less than about 25 nS / m when measured in the range of about 20°C to about 150°C. For example, the oil composition may have a conductivity of less than about 25 nS / m when measured in the range of about 20°C to about 140°C, about 20°C to about 120°C, about 20°C to about 120°C, about 20°C to about 110°C, or about 20°C to about 100°C.

[0126] In some embodiments, the oil composition described herein has a conductivity of less than about 40 nS / m when measured at a temperature of about 30°C. In some embodiments, the oil composition described herein has a conductivity of less than about 25 nS / m when measured at a temperature of about 30°C. For example, the oil composition may have a conductivity of less than about 25 nS / m, less than about 25 nS / m, less than about 20 nS / m, less than about 15 nS / m, or less than about 10 nS / m when measured at a temperature of about 30°C.

[0127] In some embodiments, the oil composition described herein has a conductivity of about 0.1 nS / m to about 100 nS / m when measured in the range of about 20°C to about 150°C. For example, when measured in the range of about 20°C to about 150°C, the oil composition may have a conductivity of about 0.1 nS / m to about 80 nS / m, about 0.1 nS / m to about 75 nS / m, about 0.1 nS / m to about 70 nS / m, about 0.1 nS / m to about 60 nS / m, about 0.1 nS / m to about 50 nS / m, about 0.1 nS / m to about 40 nS / m, about 0.1 nS / m to about 30 nS / m, about 0.1 nS / m to about 25 nS / m, about 0.1 nS / m to about 20 nS / m, or about 0.1 nS / m to about 15 nS / m.

[0128] In some embodiments, the oil composition described herein has a thermal conductivity greater than about 120 mW / (m*K) when measured over a range of about 20°C to about 150°C. For example, the oil composition may have a thermal conductivity greater than about 120 mW / (m*K), greater than about 130 mW / (m*K), greater than about 140 mW / (m*K), or greater than about 150 mW / (m*K) when measured over a range of about 20°C to about 150°C. It should be understood that the thermal conductivity of the oil composition can be measured using the ASTM D7896-19 test standard.

[0129] In some embodiments, the oil composition described herein has a thermal conductivity of about 120 mW / (m*K) to about 200 mW / (m*K) when measured in the range of about 20°C to about 150°C. For example, when measured in the range of about 20°C to about 150°C, the oil composition may have a thermal conductivity of about 130 mW / (m*K) to about 200 mW / (m*K), about 140 mW / (m*K) to about 200 mW / (m*K), about 150 mW / (m*K) to about 200 mW / (m*K), about 140 mW / (m*K) to about 190 mW / (m*K), about 140 mW / (m*K) to about 180 mW / (m*K), about 140 mW / (m*K) to about 170 mW / (m*K), about 140 mW / (m*K) to about 160 mW / (m*K), or about 140 mW / (m*K) to about 150 mW / (m*K).

[0130] In some embodiments, the oil composition described herein has a thermal conductivity of about 120 mW / (m*K) to about 200 mW / (m*K) when measured at a temperature of about 30°C. For example, when measured at a temperature of about 30°C, the oil composition may have a thermal conductivity of about 130 mW / (m*K) to about 200 mW / (m*K), about 140 mW / (m*K) to about 200 mW / (m*K), about 150 mW / (m*K) to about 200 mW / (m*K), about 140 mW / (m*K) to about 190 mW / (m*K), about 140 mW / (m*K) to about 180 mW / (m*K), about 140 mW / (m*K) to about 170 mW / (m*K), about 140 mW / (m*K) to about 160 mW / (m*K), or about 140 mW / (m*K) to about 150 mW / (m*K).

[0131] In some embodiments, the oil composition described herein has a thermal conductivity greater than about 120 mW / (m*K) when measured in the range of about 20°C to about 150°C. For example, the oil composition may have a thermal conductivity greater than about 120 mW / (m*K), greater than about 130 mW / (m*K), greater than about 140 mW / (m*K), or greater than about 150 mW / (m*K) when measured in the range of about 20°C to about 150°C.

[0132] In some embodiments, the oil composition described herein has a thermal conductivity greater than about 120 mW / (m*K) when measured at a temperature of about 30°C. For example, the oil composition may have a thermal conductivity greater than about 120 mW / (m*K), greater than about 130 mW / (m*K), greater than about 140 mW / (m*K), or greater than about 150 mW / (m*K) when measured at a temperature of about 30°C.

[0133] In some embodiments, the oil composition as described herein has a specific gravity of less than about 1.00. For example, the oil composition may have a specific gravity of less than about 0.99, less than about 0.98, less than about 0.97, less than about 0.96, less than about 0.95, less than about 0.94, less than about 0.93, less than about 0.92, less than about 0.91, or less than about 0.90. In some embodiments, the oil composition has a specific gravity of from about 0.80 to about 1.00. For example, the oil composition may have a specific gravity of about 0.85 to about 1.00, about 0.90 to about 1.00, about 0.85 to about 0.99, about 0.85 to about 0.98, about 0.85 to about 0.97, about 0.85 to about 0.96, about 0.85 to about 0.95, about 0.85 to about 0.94, about 0.85 to about 0.93, about 0.85 to about 0.92, about 0.85 to about 0.91, about 0.85 to about 0.90, about 0.90 to about 0.99, about 0.90 to about 0.98, about 0.90 to about 0.97, about 0.90 to about 0.96, about 0.90 to about 0.95, about 0.90 to about 0.94, about 0.90 to about 0.93, about 0.90 to about 0.92, or about 0.90 to about 0.91. It should be understood that the specific gravity of an oil composition can be measured using the ASTM D891B test standard, for example, by using a hydrometer.

[0134] In some embodiments, the oil composition as described herein provides a wear scar diameter (WSD) of less than about 400 μm. For example, the oil composition may provide a WSD of less than about 375 μm, less than about 350 μm, less than about 325 μm, less than about 300 μm, less than about 290 μm, less than about 280 μm, less than about 270 μm, less than about 260 μm, less than about 250 μm, less than about 240 μm, less than about 230 μm, less than about 220 μm, less than about 210 μm, or less than about 200 μm. In some embodiments, the oil composition provides a wear scar diameter (WSD) of from about 100 μm to about 500 μm. For example, oil compositions may be available with a wear scar diameter (WSD) of about 100 μm to about 400 μm, about 100 μm to about 375 μm, about 100 μm to about 350 μm, about 100 μm to about 325 μm, about 100 μm to about 300 μm, about 100 μm to about 290 μm, about 100 μm to about 280 μm, about 100 μm to about 270 μm, about 100 μm to about 260 μm, about 100 μm to about 250 μm, about 200 μm to about 400 μm, about 1200 μm to about 375 μm, about 200 μm to about 350 μm, about 200 μm to about 325 μm, or about 200 μm to about 300 μm. It should be understood that the WSD of the oil composition can be measured using ASTM D6079 test standard or a modified version thereof.

[0135] In some embodiments, the oil composition as described herein provides an average coefficient of friction (COF) of less than about 0.25. For example, the oil composition may provide a COF of less than about 0.24, less than about 0.23, less than about 0.22, less than about 0.21, less than about 0.20, less than about 0.19, less than about 0.18, less than about 0.17, less than about 0.16, less than about 0.15, less than about 0.14, less than about 0.13, less than about 0.12, less than about 0.11, or less than about 0.10. In some embodiments, the oil composition provides a COF of from about 0.10 to about 0.25. For example, the oil composition may provide COF of about 0.10 to about 0.24, about 0.10 to about 0.23, about 0.10 to about 0.22, about 0.10 to about 0.21, about 0.10 to about 0.20, about 0.10 to about 0.19, about 0.10 to about 0.18, about 0.10 to about 0.17, about 0.10 to about 0.16, about 0.10 to about 0.15, about 0.10 to about 0.14, about 0.10 to about 0.13, about 0.10 to about 0.12, or about 0.10 to about 0.11.

[0136] In some embodiments, the oil composition as described herein is soluble in Group II mineral oil (Gr II MO). In some embodiments, the oil composition as described herein is soluble in Group III mineral oil (Gr III MO).

[0137] In some embodiments, the oil composition as described herein is biodegradable. For example, the biodegradability of the oil composition may be based on the percentage of Formula I compounds in the composition. In some embodiments, the oil composition as described herein is at least about 25% biodegradable. For example, the oil composition may be at least about 30%, at least about 40%, at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, or at least about 75% biodegradable.

[0138] Additional embodiments, features, and advantages of this disclosure will become apparent from the following detailed description and through practice. The compounds of this disclosure may be described as embodiments in any of the following enumerated embodiments. It will be understood that any embodiment described herein may be used in combination with any other embodiment described herein to the extent that the embodiments do not contradict each other.

[0139] 1. An oil composition comprising a blend of (i) a dialkyl fumarate and (ii) an alkyl castor oil.

[0140] 2. The oil composition according to embodiment 1, wherein the dialkyl fumarate and the alkyl castor oil are present in the composition in a ratio of about 1:1.

[0141] 3. The oil composition according to any one of embodiments 1-2, wherein the dialkyl fumarate is di(C6-C6) fumarate. 12 Alkyl ester.

[0142] 4. The oil composition according to any one of embodiments 1-3, wherein each alkyl chain in the dialkyl fumarate is a C8 alkyl chain.

[0143] 5. The oil composition according to any one of embodiments 1-4, wherein each alkyl chain in the dialkyl fumarate is a straight chain.

[0144] 6. The oil composition according to any one of embodiments 1-5, wherein the dialkyl fumarate is: .

[0145] 7. The oil composition according to any one of embodiments 1-6, wherein the alkyl ricinoleate is a C1-C3 alkyl ricinoleate.

[0146] 8. The oil composition according to any one of embodiments 1-7, wherein the alkyl ricinoleate is methyl ricinoleate.

[0147] 9. A base oil composition comprising the oil composition of any one of embodiments 1-8.

[0148] 10. An automotive oil comprising the oil composition described in any one of embodiments 1-8.

[0149] 11. An automotive cooling fluid comprising the oil composition described in any one of embodiments 1-8.

[0150] 12. An additive for use in automotive base oil compositions comprising the oil composition described in any one of embodiments 1-8.

[0151] 13. An additive for use in automotive oil compositions comprising any one of the embodiments 1-8.

[0152] 14. An additive for automotive cooling fluid compositions comprising the oil composition described in any one of embodiments 1-8.

[0153] 15. A method of cooling an electric drive, comprising adding a composition to the electric drive, wherein the composition comprises an oil composition according to any one of embodiments 1-8.

[0154] 16. A method for preparing an oil composition blend comprising the composition according to any one of embodiments 1-8, comprising combining the (i) dialkyl fumarate and (ii) alkyl castor oil ester and mixing for at least 5 minutes. Example

[0155] The embodiments and preparations provided below further illustrate and exemplify specific aspects of embodiments of this disclosure. It should be understood that the scope of this disclosure is not in any way limited by the scope of the following embodiments. All ASTM, ISO, and other standard test methods referenced or mentioned in this disclosure are incorporated herein by reference in their entirety.

[0156] Example 1: This embodiment provides exemplary compatibility and solubility data for oil compositions according to certain aspects of this disclosure. Oil compositions comprising blends of synthetic and bio-based esters were prepared by combining dioctyl fumarate (DOF, synthetic ester A), dioctyl maleate (DOM, synthetic ester B), dibutyl fumarate (DBF, synthetic ester C), dibutyl maleate (DBM, synthetic ester D), methyl ricinoleate A (bio-based ester A, BA), and methyl ricinoleate B (bio-based ester B, BB) in indicated ratios. Exemplary individual oils were analyzed as shown in Table 1, and exemplary oil blends were analyzed as shown in Tables 2, 3a, and 3b. The comparative ester (Com. ester, commercial reference fluid) was diisononyl adipate. The oil compositions of bio-based and synthetic ester blends exhibited good solubility in mineral base oils (Gr II MO and Gr III MO). The exemplary esters and ester blends provide opportunities for use as standalone products or as blends in mineral base oils.

[0157] Table 1. Compatibility of single esters used in oil compositions with mineral base oils

[0158] Table 2. Compatibility of ester blends (1:1) for use in oil compositions with mineral base oils

[0159] Table 3a. Compatibility of ester blends with mineral base oils at indicated ratios for use in oil compositions

[0160] Table 3b. Compatibility of ester blends with mineral base oils at indicated ratios for use in oil compositions.

[0161] Other exemplary blends of DOF with DOM at a ratio of 75:25, DOF with DOM at a ratio of 25:75, and DOF with DBM at a ratio of 75:25 are soluble in mineral base oils (Gr II MO and Gr III MO) and diisononyl adipate (Com. ester).

[0162] Example 2: This embodiment provides exemplary characterization data for oil compositions according to certain aspects of this disclosure. Oil compositions comprising blends of synthetic and bio-based esters were prepared by combining dioctyl fumarate (DOF, synthetic ester A), dioctyl maleate (DOM, synthetic ester B), dibutyl fumarate (DBF, synthetic ester C), dibutyl maleate (DBM, synthetic ester D), methyl ricinoleate A (bio-based ester A, BA), and methyl ricinoleate B (bio-based ester B, BB) in indicated ratios. The comparative ester (Com. Ester, Commercial Reference Fluid) was diisononyl adipate. Exemplary single oils were analyzed as shown in Table 4, and exemplary oil blends were analyzed as shown in Tables 5, 6a, and 6b.

[0163] Data were obtained and presented according to the ASTM methods provided in this document. Viscosity, KV100, and KV40 were determined according to the method described in ASTM D445. Pour point was determined according to the method described in ASTM D97. Flash point was determined according to the method described in ASTM D93. Noack volatility was determined according to the method described in ASTM D5800. Entrained water was determined according to the method described in ASTM D6304. Hydrolytic stability was determined according to the method described in ASTM D2619.

[0164] Table 4. Properties of single esters used in oil compositions (base oil / cooling fluid).

[0165] Table 5 Properties of ester blends with indicated ratios used in oil compositions

[0166] Table 6a. Properties of ester blends with indicated ratios used in oil compositions

[0167] Table 6b. Properties of ester blends with indicated ratios used in oil compositions

[0168] Example 3: Conductivity Conductivity measurements were performed using an Epsilon+ dielectric meter according to the requirements of DIN EN 51 111 test standard. Specific conductivity measurements were performed under pure (neat) conditions at an applied frequency of 20 Hz over a wide temperature range of 20 to 150 °C. For blends (e.g., 1:1 ratio), the components were mixed and stirred at room temperature for 30 minutes. All tests were performed on the resulting blends without any further treatment. The results are shown below. Figure 1-3 middle.

[0169] Example 4: Thermal conductivity The thermal conductivity of the fluid was measured using a Flucon Lambda thermal conductivity meter. The test was based on the hot-wire method and performed according to ASTM D7896-19. The test method was designed to measure the thermal conductivity of the test sample over a temperature range up to 300°C. Depending on the application, in this case, the equipment was set up to measure the temperature distribution in the range of 20°C–150°C. The results are shown below. Figure 4 middle.

[0170] Example 5: High Frequency Reciprocating Testing Machine (HFRR) The High Frequency Reciprocating Test Chamber (HFRR) is an industry-recognized test for measuring the lubricity of fuels and lubricants. Lubricity is a critical parameter of fluid quality and is important for maintaining the proper functioning of fuel injection system hardware. The industry has adopted the following standard tests to quantify the suitability of fuels for lubricity requirements: CEC F-06-A-96, ASTM D6079, ASTM 7688, ISO BS EN 590, ISO 12156-1, JPI-5S-50-98, and IP 450 / 2000. The test procedure involves repeatedly rubbing a 5 mm alloy steel ball against a 10 mm alloy steel disc at a high frequency (50 Hz) for 75 minutes under an 8 N load in the presence of a fluid sample maintained at 60 °C. The wear scar diameter (WSD) on the ball is measured in both parallel and perpendicular directions of sliding, and the average wear scar is reported. The coefficient of friction (COF) is also measured. The results are shown in Tables 7, 8, and 9. Figure 5-6 middle.

[0171] Table 7. Test data of the high frequency reciprocating tester (HFRR).

[0172] Table 8. High-Frequency Reciprocating Tester (HFRR) test data for synthetic esters and blends.

[0173] Table 9. High-Frequency Reciprocating Test (HFRR) Data of Bio-ester Blends in Comparative Esters

[0174] Example 6: Stability and Floc Formation The components were mixed in a flat-bottomed glass vial for 30 minutes at room temperature (approximately 25°C). The resulting blend was stored at room temperature (approximately 25°C) for 5 days, and then separately stored in a laboratory refrigerator (0°C) for 5 days. Any dropout / precipitation at the bottom of the vial (after 5 days) was recorded as flocculent material. The results are shown in Table 10. The sample flocculent material was separated and analyzed, as shown in Figures 7A-7C.

[0175] Table 10. Environmental temperature and low-temperature stability of bio-esters and blends

Claims

1. An oil composition comprising (i) a blend of an alkenyl diester and (ii) a compound of formula I or a salt thereof, in R 1 It is an alkyl group (e.g., C1-C6 alkyl). R 2 It is an H or acyl group (e.g., C1-C6 acyl group), and n, m, and p are each an independent integer of 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

2. The oil composition according to claim 1, wherein the compound of formula I is an alkyl ester of castor oil.

3. An oil composition comprising a blend of (i) a dialkyl fumarate and (ii) an alkyl castor oil.

4. The oil composition according to claim 2 or 3, wherein the alkyl ricinoleate is methyl ricinoleate.

5. The oil composition according to claim 2 or 3, wherein the alkyl castor oil ester has formula IIa: or its salt, wherein R 1 It is an alkyl group (e.g., C1-C6 alkyl), and R 2 It is an H or acyl group (e.g., C1-C6 acyl group).

6. The oil composition according to any one of claims 1, 2, 4 or 5, wherein R 2 It is H or acetyl.

7. The oil composition according to any one of claims 1, 2, or 4-6, wherein R 2 It is H.

8. The oil composition according to any one of claims 1, 2, or 4-6, wherein R 2 It is an acetyl group.

9. The oil composition according to any one of claims 1, 2, or 4-8, wherein the imendene diester has formula III: in R 3 R 4 R 5 and R 6 Each is independently H or an ester (e.g., -C(O)O alkyl). The conditions are: R 3 and R 4 One of them is H, and R 3 and R 4 Another one is ester, and R 5 and R 6 One of them is H, and R 5 and R 6 Another one is an ester.

10. The oil composition according to any one of claims 1, 2 or 4-9, wherein the imidene diester is a dialkyl fumarate, a dialkyl maleate, or a combination thereof.

11. The oil composition according to any one of claims 1, 2 or 4-10, wherein the imendene diester is a dialkyl fumarate.

12. The oil composition according to any one of the preceding claims, wherein the imendene diester (e.g., dialkyl fumarate) has the formula (IVa): Each R 7 It is an alkyl group (e.g., C2-C). 12 alkyl).

13. The oil composition according to claim 12, wherein each R 7 It is a C4-C8 alkyl group (e.g., butyl, pentyl, hexyl, heptyl, or octyl).

14. The oil composition according to any one of the preceding claims, wherein the imendene diester (e.g., dialkyl fumarate) is dioctyl fumarate (DOF), dibutyl fumarate (DBF), or a combination thereof.

15. The oil composition according to any one of the preceding claims, wherein the imendene diester (e.g., dialkyl fumarate) is: 。 16. The oil composition according to any one of claims 1, 2 or 4-10, wherein the imidene diester is a dialkyl maleate ester.

17. The oil composition according to any one of claims 1, 2, 4-10 or 16, wherein the imidene diester (e.g., dialkyl maleate) has the formula (IVb): Each R 8 It is an alkyl group (e.g., C2-C). 12 alkyl).

18. The oil composition according to claim 17, wherein each R 8 It is a C4-C8 alkyl group (e.g., butyl, pentyl, hexyl, heptyl, or octyl).

19. The oil composition according to any one of claims 1, 2, 4-10 or 16-18, wherein the imidene diester (e.g., dialkyl maleate) is dioctyl maleate (DOM), dibutyl maleate (DBM), or a combination thereof.

20. The oil composition according to any one of claims 1, 2, 4-10 or 16-19, wherein the imendene diester is a combination of dioctyl maleate (DOM) and dibutyl maleate (DBM).

21. The oil composition according to any one of the preceding claims, wherein the imidene diester (e.g., dialkyl fumarate or dialkyl maleate) and the compound of formula I are present in the composition in a ratio of about 5:1 to about 1:

5.

22. The oil composition according to any one of the preceding claims, wherein the imidene diester (e.g., dialkyl fumarate or dialkyl maleate) and the alkyl castor oil ester are present in the composition in a ratio of about 1:

1.

23. The oil composition according to any one of the preceding claims, wherein the oil composition has a viscosity (KV40) of less than about 15 cSt (e.g., about 3 cSt to about 15 cSt).

24. The oil composition according to any one of the preceding claims, wherein the oil composition has a conductivity of less than about 100 nS / m (e.g., about 0.1 nS / m to about 100 nS / m) when measured in the range of about 20°C to about 150°C.

25. The oil composition according to any one of the preceding claims, wherein the oil composition has a thermal conductivity greater than about 120 mW / (m*K) (e.g., about 120 mW / (m*K) to about 200 mW / (m*K)) when measured in the range of about 20°C to about 150°C.

26. The oil composition according to any one of the preceding claims, wherein the oil composition is a base oil (e.g., automotive base oil), a cooling fluid, or a combination thereof.

27. A base oil composition comprising the oil composition according to any one of claims 1-25.

28. A cooling fluid comprising the oil composition according to any one of claims 1-25.

29. The cooling fluid of claim 28, wherein the cooling fluid is an automotive cooling fluid.

30. The cooling fluid according to claim 28 or 29, wherein the cooling fluid is an immersion cooling fluid.

31. An additive for use in base oil compositions comprising an oil composition according to any one of claims 1-25.

32. The additive according to claim 31, wherein the base oil composition is an automotive base oil composition.

33. An additive for cooling fluids, comprising an oil composition according to any one of claims 1-25.

34. The additive of claim 33, wherein the cooling fluid is an automotive cooling fluid.

35. The additive according to claim 33 or 34, wherein the cooling fluid is an immersion cooling fluid.

36. A method of cooling an electric drive, comprising adding a composition to the electric drive, wherein the composition comprises an oil composition according to any one of claims 1-25.

37. A method for preparing an oil composition blend comprising the composition according to any one of claims 1, 2, or 4-25, comprising: Combine (i) the alkenyl diester (e.g., dialkyl fumarate or dialkyl maleate) and (ii) the compound of formula I, and mix for at least 5 minutes.

38. A method for preparing an oil composition blend comprising the composition according to claim 3, comprising: Combine (i) the dialkyl fumarate and (ii) the alkyl castor oil ester and mix for at least 5 minutes.

Images