# US 2020/0399553 A1 · Glycol Ether Ester Compounds Of Neo-Alcohols Useful In Lubricating Oil Compositions And Methods Of Making The Same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2020/0399553 A1 - Document ID: US20200399553A1 - Status: Published application - Kind: A1 - Application number: 16/872,994 - Filed: 2020-05-12 - Published: 2020-12-24 - Earliest claimed: 2019-06-21 - Assignees: ExxonMobil Research and Engineering Company - Applicants: ExxonMobil Research and Engineering Company - Inventors: Abhimanyu O. Patil; Satish Bodige; Kyle G. Lewis - Web page: https://patentgrep.com/patent/US20200399553A1 ## CPC - C10M 105/34: of monocarboxylic acids - C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds - C07C 69/708: Ethers - C10M 107/34: Polyoxyalkylenes - C10M 2207/2815: used as base material - C10M 2209/109: esterified - C10M 2209/1095: used as base material - C10N 2020/02: Viscosity; Viscosity index - C10N 2020/065: {Saturated Compounds} - C10N 2020/071: {Branched chain compounds} - C10N 2030/02: Pour-point; Viscosity index - C10N 2030/74: {Noack Volatility} - C10N 2040/25: Internal-combustion engines - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS ## Abstract Compositions include ether ester compounds derived from neo-alcohols, lubricating oil base stocks containing such ester compounds, and lubricating oil compositions containing such ester compounds. Methods can include making and formulating compositions containing ether ester compounds derived from neo-alcohols. ## Claims ### Claim 1 A compound of the structural Formula F-I: wherein R1 and R2 are independently each a hydrocarbyl group comprising at least 2 carbon atoms; and R3 is a glycol ether or a polyglycol ether. ### Claim 2 (depends on 1) The compound of claim 1, wherein R1 and R2 are each independently a C2 to C30 linear or branched alkyl group. ### Claim 3 (depends on 1) The compound of claim 1, wherein at least one of R1 and R2 is a linear alkyl group. ### Claim 4 (depends on 3) The compound of claim 3, wherein at least one of R1 and R2 is selected from ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-icosyl, n-docosyl, n-tetracosyl, n-hexacosyl, and n-octacosyl. ### Claim 5 (depends on 4) The compound of claim 4, wherein at least one of R1 and R2 is selected from n-butyl, n-hexyl, n-octyl, n-decyl, and n-dodecyl. ### Claim 6 (depends on 1) The compound of claim 1, wherein R1 and R2 are independently each a linear alkyl group. ### Claim 7 (depends on 1) The compound of claim 1, wherein at least one of R1 and R2 is a branched alkyl group. ### Claim 8 (depends on 7) The compound of claim 7, wherein at least one of R1 and R2 is selected from ethylhexyl, 2-propylheptanyl, 2-butyloctyl, and 3,5-dimethyloctyl. ### Claim 9 (depends on 1) The compound of claim 1, wherein R1 and R2 are identical. ### Claim 10 (depends on 1) The compound of claim 1, wherein R3 is a glycol ether of the structural formula: wherein each R4 is the same or different and is hydrogen or a substituted or unsubstituted alkyl group (C1-C30), alkenyl group (C1-C30), alkoxy group (C1-C30), aryl group (C4-C30), or arylalkyl group (C5-C30), R5 is hydrogen or a substituted or unsubstituted alkyl group (C1-C30), alkenyl group (C1-C30), alkoxy group (C1-C30), aryl group (C4-C30), or arylalkyl group (C5-C30), x is a value from about 0 to about 10, and y is a value from about 1 to about 10. ### Claim 11 (depends on 1) The compound of claim 1, wherein R3 is a polyglycol ether of the structural formula: wherein each R4 is the same or different and is hydrogen or a substituted or unsubstituted alkyl group (C1-C30), alkenyl group (C1-C30), alkoxy group (C1-C30), aryl group (C4-C30), or arylalkyl group (C5-C30), R5 is hydrogen or a substituted or unsubstituted alkyl group (C1-C30), alkenyl group (C1-C30), alkoxy group (C1-C30), aryl group (C41-C30), or arylalkyl group (C5-C30), x is a value from about 0 to about 10, y is a value from about 1 to about 10, and z is a value from about 0 to about 100. ### Claim 12 (depends on 1) The compound of claim 1, wherein the compound is one or more compounds selected from the group of 2-methyl-2-octyldodecyl 2-(2-methoxyethoxy)acetate, 2-ethyl-2-octyldodecyl 2-(2-methoxyethoxy)acetate, 2-methyl-2-hexyldecyl 2-(2-methoxyethoxy)acetate, 2-methyl-2-octyldodecyl 2-(2-ethoxyethoxy)acetate, 2-methyl-2-octyldodecyl 2-(3-methoxypropoxy)acetate, 2-methyl-2-octyldodecyl 3-(2-methoxyethoxy)propionate, 2-methyl-2-octyldodecyl 2-(2-(2-methoxyethoxy)ethoxy)acetate, 2-ethyl-2-octyldodecyl 2-(2-(2-methoxyethoxy)ethoxy)acetate, 2-methyl-2-hexyldecyl 2-(2-(2-methoxyethoxy)ethoxy)acetate, 2-methyl-2-octyldodecyl 2-(2-(2-ethoxyethoxy)ethoxy)acetate, 2-methyl-2-octyldodecyl 24243-methoxypropoxy)ethoxy)acetate, 2-methyl-2-octyldodecyl 2-(3-(2-methoxyethoxy)propoxy)acetate, and 2-methyl-2-octyldodecyl 3-(2-(2-ethoxyethoxy)ethoxy)propionate. ### Claim 13 (depends on 1) The compound of claim 1, wherein the compound is 2-methyl-2-octyldodecyl 2-(2-methoxyethoxy)acetate or 2-methyl-2-octyldodecyl 2-(2-methoxyethoxy)ethoxy acetate. ### Claim 14 A lubricating oil composition comprising a compound defined by the structural Formula F-I: wherein R1 and R2 are independently each a hydrocarbyl group comprising at least 2 carbon atoms; and R3 is a glycol ether or a polyglycol ether. ### Claim 15 (depends on 14) A lubricating oil composition of claim 14, which is a lubricating oil formulation. ### Claim 16 (depends on 1) A lubricating oil composition comprising one or more compounds of claim 1. ### Claim 17 (depends on 16) A lubricating oil composition of claim 16, wherein the lubricating oil composition is formulated as a coolant for an electric vehicle. ### Claim 18 (depends on 16) The lubricating oil composition of claim 16 having a kinematic viscosity at 100° C. as determined pursuant to ASTM D445 in the range from 1 to 140 cSt. ### Claim 19 A method for making an ester product comprising an ester compound of the structural Formula F-I: where R1 and R2 are independently each a hydrocarbyl group comprising at least two carbon atoms; and R3 is a glycol ether or a polyglycol ether, the method comprising the steps of: providing a neo-alcohol of the structural Formula F-II: wherein R1 and R2 are the same as the R1 and R2 o Formula F-I, respectively; reacting the neo-alcohol with an acid of the structural Formula II: wherein R3 is the same as the R3 of Formula F-I, and/or an anhydride of the acid, in the presence of an acid catalyst to obtain a product mixture; and obtaining the ester compound and/or the lubricating oil base stock from the product mixture. ### Claim 20 (depends on 19) The method of claim 19, wherein R1 and R2 are independently each a C2 to C30 linear or branched alkyl group. ### Claim 21 (depends on 19) The method of claim 19, wherein R1 and R2 are independently selected from ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-icosyl, n-docosyl, n-tetracosyl, n-hexacosyl, and n-octacosyl. ### Claim 22 (depends on 19) The method of claim 19, wherein R3 is a glycol ether of the structural formula: wherein each R4 is the same or different and is hydrogen or a substituted or unsubstituted alkyl group (C1-C30), alkenyl group (C1-C30), alkoxy group (C1-C30), aryl group (C4-C30), or arylalkyl group (C5-C30), R5 is hydrogen or a substituted or unsubstituted alkyl group (C1-C30), alkenyl group (C1-C30), alkoxy group (C1-C30), aryl group (C4-C30), or arylalkyl group (C5-C30), x is a value from about 0 to about 10, and y is a value from about 1 to about 10. ### Claim 23 (depends on 19) The method of claim 19, wherein R3 is a polyglycol ether of the structural formula: wherein each R4 is the same or different and is hydrogen or a substituted or unsubstituted alkyl group (C1-C30), alkenyl group (C1-C30), alkoxy group (C1-C30), aryl group (C4-C30), or arylalkyl group (C5-C30), R5 is hydrogen or a substituted or unsubstituted alkyl group (C1-C30), alkenyl group (C1-C30), alkoxy group (C1-C30), aryl group (C4-C30), or arylalkyl group (C5-C30), x is a value from about 0 to about 10, y is a value from about 1 to about 10, and z is a value from about 0 to about 100. ### Claim 24 (depends on 19) The method of claim 19, wherein the neo-alcohol is 2-ethyl-2-methylhexan-1-ol; 2-methyl-2-propylheptan-1-ol; 2-butyl-2-methyloctan-1-ol; 2-methyl-2-pentylnonan-1-ol; 2-hexyl-2-methyldecan-1-ol; 2-heptyl-2-methylundecan-1-ol; 2-methyl-2-octyldodecan-1-ol; 2-decyl-2-methyltetradecan-1-ol; 2-dodecyl-2-methylhexadecan-1-ol; 2-methyl-2-tetradecyloctadecan-1-ol; and/or 2-methyl-2-hexadecylicosan-1-ol; and/or mixtures and/or combinations thereof. ### Claim 25 (depends on 19) The method of claim 19, wherein the acid is 2-methyl-2-octyldodecyl 2-(2-methoxyethoxy)acetate, 2-ethyl-2-octyldodecyl 2-(2-methoxyethoxy)acetate, 2-methyl-2-hexyldecyl 2-(2-methoxyethoxy)acetate, 2-methyl-2-octyldodecyl 2-(2-ethoxyethoxy)acetate, 2-methyl-2-octyldodecyl 2-(3-methoxypropoxy)acetate, 2-methyl-2-octyldodecyl 3-(2-methoxyethoxy)propionate, 2-methyl-2-octyldodecyl 2-(2-(2-methoxyethoxy)ethoxy)acetate, 2-ethyl-2-octyldodecyl 2-(2-(2-methoxyethoxy)ethoxy)acetate, 2-methyl-2-hexyldecyl 2-(2-(2-methoxyethoxy)ethoxy)acetate, 2-methyl-2-octyldodecyl 2-(2-(2-ethoxyethoxy)ethoxy)acetate, 2-methyl-2-octyldodecyl 2-(2-(3-methoxypropoxy)ethoxy)acetate, 2-methyl-2-octyldodecyl 2-(3-(2-methoxyethoxy)propoxy)acetate, and/or 2-methyl-2-octyldodecyl 3-(2-(2-ethoxyethoxy)ethoxy)propionate.