Low viscosity, low volatility lubricating oil basestocks

Patent metadata

Field	Value
Publication number	US-9422499-B2
Application number	US-201514630022-A
Country	US
Kind code	B2
Filing date	Feb 24, 2015
Priority date	Mar 31, 2014
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

A composition containing one or more sulfur-containing compounds represented by the formula

(R 1 ) a (X)(R 2 ) b

wherein R 1 and R 2 are the same or different and are the residue of an olefin (e.g., aliphatic, aromatic or cycloaliphatic olefin) having from 4 to 40 carbon atoms, X is the residue of a thiol or polythiol, a is a value from 1 to 6, and b is a value from 0 to 6. The composition has a kinematic viscosity at 100° C. (Kv 100 ) from 2 to 300 cst, a kinematic viscosity at 40° C. (Kv 40 ) from 5 to 4000 cst, a viscosity index (VI) from −100 to 300, and a Noack volatility of no greater than 90 percent. A process for producing the composition, a lubricating oil base stock and lubricating oil containing the composition, and a method for improving one or more of solubility and dispersancy of polar additives in a lubricating oil containing the composition.

First claim

What is claimed is:

1. A composition comprising one or more sulfur-containing compounds represented by the formula
(R 1 ) a (X)(R 2 ) b
wherein R 1 and R 2 are the same or different and are the residue of an olefin having from 4 to 40 carbon atoms, X is the residue of a polythiol, a is a value from 1 to 6, and b is a value from 0 to 6;
wherein the olefin is selected from the group consisting of an aliphatic olefin, an aromatic olefin, and a cycloaliphatic olefin; and the polythiol is selected from the group consisting of an aliphatic polythiol, an aromatic polythiol, a cycloaliphatic polythiol, an ether-, ester- or acid-containing polythiol, and a heteroatom-containing polythiol; and
wherein the composition has a kinematic viscosity at a temperature of 100° C. (Kv 100 ), measured according to ASTM standard D-445, from 2 to 300 cst, a kinematic viscosity at a temperature of 40° C. (Kv 40 ), measured according to ASTM standard D-445, from 5 to 4000 cst, a viscosity index (VI), measured according to ASTM standard D-2270, from −100 to 300, and a Noack volatility, measured according to ASTM D-5800, of no greater than 90 percent.

2. The composition of claim 1 wherein:
the aliphatic olefin is selected from polyalphaolefin dimer (C 6 -C 40 ), trimer (C 6 -C 40 ), tetramer (C 6 -C 40 ), pentamer (C 6 -C 40 ), and hexamer (C 6 -C 40 ), and alpha-olefin (C 4 -C 40 ).

3. The composition of claim 1 wherein:
the aromatic olefin is selected from 2,4-dimethylstyrene, 2,5-dimethylstyrene, 4-tert-butylstyrene, 4-tert-butoxystyrene, 3,4-dimethoxystyrene, 4-acetoxystyrene, 1,3-diisopropenylbenzene, 4-ethoxystyrene, 2,3,4,5,6-pentafluorostyrene, 4-fluorostyrene, 1-(trifluoromethyl)-4-vinylbenzene, 4-[N-(methylaminoethyl)aminomethyl]styrene, 4-benzyloxy-3-methoxystyrene, 2-methoxy-4-vinylphenol, ((4-vinylphenyl)methylene)dibenzene, 1-vinylnaphthalene, 2-vinylnaphthalene, divinylbenzene, trivinylbenzene, styrene, 4-methyl styrene, 2-methyl styrene, 1-methyl styrene, 4-methoxystyrene, 2-methoxystyrene, 1-allyl-4-(trifluoromethyl)benzene, 9-vinylanthracene, 1,1-diphenylethylene, 2,3-dibenzyl-1,3-butadiene, 1-allyl-2-methylbenzene, dipentene, 4-vinylbiphenyl, 9-vinylcarbazole, N-vinylphthalimide, and 4-(trifluoromethyl)styrene.

4. The composition of claim 1 wherein:
the cycloaliphatic olefin is selected from vinylcyclopentane, vinylcyclohexane, allylcyclohexane, 1,2,4-trivinylcyclohexane, and 5-vinyl-2-norbornene.

5. The composition of claim 1 wherein:
the aliphatic polythiol is selected from 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol, 1,8-octanedithiol, 1,9-nonanedithiol, 1,11-undecanedithiol, and 1,16-hexadecanedithiol;
the aromatic polythiol is selected from benzene-1,2-dithiol, benzene-1,3-dithiol, toluene-3,4-dithiol, 5-phenyl-1,3,4-oxadiazole-2-thiol, 1,3,4-thiodizole-2,5-dithiol, 1,2,4-thiadiazole-3,5-dithiol, 1,2-benzenedimethanedithiol, 1,3-benzenedimethanedithiol, and 1,4-benzenedimethanedithiol;
the cycloaliphatic polythiol is selected from 1,5-cyclooctanedithiol, 4-hexyl-1,2-cyclohexanedithiol, and p-menthane-2,9-dithiol;
the ether-, ester- or acid-containing polythiol is selected from 2-mercaptoethyl ether, 2,2′-(ethylenedioxy)diethanethiol, hexa(ethylene glycol)dithiol, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate); and
the heteroatom-containing polythiol is selected from, 2-thizoline-2-thiol, 2-mercaptobenzothiazole, 5-methoxylbenzoxazole-2-thiol, 5-phenyl-1H-1,2,4-trizole-3-thiol, 1H-1,24-trizole-3-thiol, 5-phenyl-1,3,4-oxadiazole-2-thiol, 2-thiazoline-2-thiol, 2-mercaptobenzothiazole, 5-methoxybenzoxazole-2-thiol, 4-phenylimidazole-2-thiol, 2-mercaptoimidazole, 1H-1,2,4-trizole-3-thiol, 5-phenyl-1,3,4-oxadiazole-2-thiol 1,3,4-thiodizole-2,5-dithiol, and 1,2,4-thiadiazole-3,5-dithiol.

6. The composition of claim 1 which has a kinematic viscosity at a temperature of 100° C. (Kv 100 ), measured according to ASTM standard D-445, from 2.2 to 200 cst, a kinematic viscosity at a temperature of 40° C. (Kv 40 ), measured according to ASTM standard D-445, from 20 to 2000 cst, a viscosity index (VI), measured according to ASTM standard D-2270, from 50 to 250, and a Noack volatility, measured according to ASTM D-5800, of no greater than 50 percent.

7. A composition comprising one or more sulfur-containing compounds, wherein said one or more sulfur-containing compounds are produced by a process which comprises:
reacting an olefin with a polythiol, optionally in the presence of a catalyst, under thiol-ene reaction conditions sufficient to produce the one or more sulfur-containing compounds;
wherein the olefin is selected from the group consisting of an aliphatic olefin, an aromatic olefin, and a cycloaliphatic olefin; and the polythiol is selected from the group consisting of an aliphatic polythiol, aromatic polythiol, cycloaliphatic polythiol, an ether-, ester- or acid-containing polythiol, and a heteroatom-containing polythiol; and
wherein the composition has a kinematic viscosity at a temperature of 100° C. (Kv 100 ), measured according to ASTM standard D-445, from 2 to 300 cst, a kinematic viscosity at a temperature of 40° C. (Kv 40 ), measured according to ASTM standard D-445, from 5 to 4000 cst, a viscosity index (VI), measured according to ASTM standard D-2270, from −100 to 300, and a Noack volatility, measured according to ASTM D-5800, of no greater than 90 percent.

8. A process for producing a composition comprising one or more sulfur-containing compounds, said process comprising:
reacting an olefin with a polythiol, optionally in the presence of a catalyst, under thiol-ene reaction conditions sufficient to produce said composition;
wherein the olefin is selected from the group consisting of an aliphatic olefin, an aromatic olefin, and a cycloaliphatic olefin; and the polythiol is selected from the group consisting of an aliphatic polythiol, aromatic polythiol, cycloaliphatic polythiol, an ether-, ester- or acid-containing polythiol, and a heteroatom-containing polythiol; and
wherein the composition has a kinematic viscosity at a temperature of 100° C. (Kv 100 ), measured according to ASTM standard D-445, from 2 to 300 cst, a kinematic viscosity at a temperature of 40° C. (Kv 40 ), measured according to ASTM standard D-445, from 5 to 4000 cst, a viscosity index (VI), measured according to ASTM standard D-2270, from −100 to 300, and a Noack volatility, measured according to ASTM D-5800, of no greater than 90 percent.

9. The process of claim 8 wherein:
the aliphatic olefin is selected from polyalphaolefin dimer (C 6 -C 40 ), trimer (C 6 -C 40 ), tetramer (C 6 -C 40 ), pentamer (C 6 -C 40 ), and hexamer (C 6 -C 40 ), and alpha-olefin (C 4 -C 40 ).

10. The process of claim 8 wherein:
the aromatic olefin is selected from 2,4-dimethylstyrene, 2,5-dimethylstyrene, 4-tert-butylstyrene, 4-tert-butoxystyrene, 3,4-dimethoxystyrene, 4-acetoxystyrene, 1,3-diisopropenylbenzene, 4-ethoxystyrene, 2,3,4,5,6-pentafluorostyrene, 4-fluorostyrene, 1-(trifluoromethyl)-4-vinylbenzene, 4-[N-(methylaminoethyl)aminomethyl]styrene, 4-benzyloxy-3-methoxystyrene, 2-methoxy-4-vinylphenol, ((4-vinylphenyl)methylene)dibenzene, 1-vinylnaphthalene, 2-vinylnaphthalene, divinylbenzene, trivinylbenzene, styrene, 4-methyl styrene, 2-methyl styrene, 1-methyl styrene, 4-methoxystyrene, 2-methoxystyrene, 1-allyl-4-(trifluoromethyl)benzene, 9-vinylanthracene, 1,1-diphenylethylene, 2,3-dibenzyl-1,3-butadiene, 1-allyl-2-methylbenzene, dipentene, 4-vinylbiphenyl, 9-vinylcarbazole, N-vinylphthalimide, and 4-(trifluoromethyl)styrene.

11. The process of claim 8 wherein:
the cycloaliphatic olefin is selected from vinylcyclope

Assignees

• Exxonmobil Res & Eng Co

Inventors

• Patil Abhimanyu O
• Bodige Satish
• Hagemeister Mark P

Classifications

• C10M139/04

  having a silicon-to-carbon bond, e.g. silanes · CPC title

• C07C321/20

  of an unsaturated carbon skeleton containing rings · CPC title

• C10M159/12

  Reaction products · CPC title

• C10M135/26

  containing carboxyl groups; Derivatives thereof · CPC title

• C10N2030/74

  Noack Volatility · CPC title