Low viscosity low volatility lubricating oil base stocks and methods of use thereof

Patent metadata

Field	Value
Publication number	US-9976099-B2
Application number	US-201615384471-A
Country	US
Kind code	B2
Filing date	Dec 20, 2016
Priority date	Dec 28, 2015
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

A composition including one or more aromatic alkanoate monoester compounds represented by the formulae (I) and (II) as defined herein. The composition has a viscosity (Kv 100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800. 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 thermal and oxidative stability, solubility and dispersancy of polar additives, deposit control and traction control in a lubricating oil by using as the lubricating oil a formulated oil containing the composition.

First claim

The invention claimed is:

1. A composition comprising one or more compounds represented by the formula selected from the group consisting of

wherein R 1 and R 2 are independently a substituted or unsubstituted alkyl group (C 1 -C 30 ), R 3 , R 4 and R 13 are independently hydrogen or a substituted or unsubstituted alkyl group (C 1 -C 30 ), alkenyl group (C 1 -C 30 ), or alkoxy group (C 1 -C 30 ), R 7 is an unsubstituted aryl group (C 4 -C 30 ) and R 8 is a substituted or unsubstituted aryl group (C 4 -C 30 ), heteroaryl group (C 4 -C 30 ), or arylalkyl group (C 5 -C 30 ), R 5 , R 6 , R 9 , R 10 , R 11 and R 12 are hydrogen, m is a value from about 1 to about 10, and n is a value greater than or equal to 1; wherein said composition has a viscosity (Kv 100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800.

2. The composition of claim 1 having a Noack volatility of no greater than Noack=[−18(Kv 100 )+70] as determined by ASTM D5800.

3. The composition of claim 1 wherein R 1 and R 2 are independently a substituted or unsubstituted alkyl group (C 1 -C 20 ), R 3 , R 4 and R 13 are independently hydrogen or a substituted or unsubstituted alkyl group (C 1 -C 20 ), alkenyl group (C 1 -C 20 ), or alkoxy group (C 1 -C 20 ), R 7 is an unsubstituted aryl group (C 4 -C 20 ) and R 8 is a substituted or unsubstituted aryl group (C 4 -C 20 ), heteroaryl group (C 4 -C 20 ), or arylalkyl group (C 5 -C 20 ), R 5 , R 6 , R 9 , R 10 , R 11 and R 12 are hydrogen, m is a value from about 1 to about 9, and n is a value greater than or equal to 2.

4. The composition of claim 1 wherein R 1 and R 2 are independently a substituted or unsubstituted alkyl group (C 1 -C 10 ); R 3 , R 4 and R 13 are independently hydrogen or a substituted or unsubstituted alkyl group (C 1 -C 10 ), alkenyl group (C 1 -C 10 ), or alkoxy group (C 1 -C 10 ), R 7 is an unsubstituted aryl group (C 4 -C 10 ) and R 8 is a substituted or unsubstituted aryl group (C 4 -C 10 ), heteroaryl group (C 4 -C 10 ), or arylalkyl group (C 5 -C 10 ), R 5 , R 6 , R 9 , R 10 , R 11 and R 12 are hydrogen, m is a value from about 1 to about 8, and n is a value greater than or equal to 1.

5. The composition of claim 1 which is selected from the group consisting of 2-hexyl-1-decyl phenylacetate, 2-hexyl-1-decyl 3-phenylpropionate, 2-hexyl-1-decyl 4-phenylbutyrate, 2-octyl-1-dodecyl phenylacetate, 2-octyl-1-dodecyl 3-phenylpropionate, 2-octyl-1-dodecyl 4-phenylbutyrate, 2-heptyl-1-undecyl phenylacetate, 2-heptyl-1-undecyl 3-phenylpropionate, 2-heptyl-1-undecyl 4-phenylbutyrate, 2-decyl-1-tetradecyl phenylacetate, 2-decyl-1-tetradecyl 3-phenylpropionate, 2-butyl-1-octyl 4-phenylbutyrate, 2-phenylethyl 2-hexyldecanoate, 3-phenylpropyl 2-hexyldecanoate, 4-phenylbutyl 2-hexyldecanoate, 2-phenylethyl 2-heptylundecanoate, 3-phenylpropyl 2-heptylundecanoate, and 4-phenylbutyl 2-heptylundecanoate.

6. The composition of claim 1 which has a high temperature high shear (HTHS) viscosity of less than about 1.7 cP as determined by ASTM D4683, and a Noack volatility from about 6 to about 30 percent as determined by ASTM D5800.

7. The composition of claim 1 which has a high temperature high shear (HTHS) viscosity of less than about 1.6 cP as determined by ASTM D4683, and a Noack volatility from about 8 to about 28 percent as determined by ASTM D5800.

8. The composition of claim 1 which has a viscosity (Kv 100 ) from about 2 cSt to about 8 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about 25 to about 150 as determined by ASTM D2270, and a Noack volatility of no greater than 25 percent as determined by ASTM D5800.

9. A composition comprising one or more compounds represented by the formula selected from the group consisting of

wherein R 1 and R 2 are independently a substituted or unsubstituted alkyl group (C 1 -C 30 ), R 3 , R 4 and R 13 are independently hydrogen or a substituted or unsubstituted alkyl group (C 1 -C 30 ), alkenyl group (C 1 -C 30 ), or alkoxy group (C 1 -C 30 ), R 7 is an unsubstituted aryl group (C 4 -C 30 ) and R 8 is a substituted or unsubstituted aryl group (C 4 -C 30 ), heteroaryl group (C 4 -C 30 ), or arylalkyl group (C 5 -C 30 ), R 5 , R 6 , R 9 , R 10 , R 11 and R 12 are hydrogen, m is a value from about 1 to about 10, and n is a value greater than or equal to 1; wherein said composition has a viscosity (Kv 100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800; wherein said one or more compounds of formula (I) are produced by a process comprising reacting a substituted or unsubstituted alcohol with a substituted or unsubstituted aromatic alkanoic acid, optionally in the presence of a catalyst and a solvent, under reaction conditions sufficient to produce said one or more compounds of formula (I); or wherein said one or more compounds of formula (II) are produced by a process comprising reacting a substituted or unsubstituted aromatic alcohol with a substituted or unsubstituted alkanoic acid, optionally in the presence of a catalyst and a solvent, under reaction conditions sufficient to produce said one or more compounds of formula (II).

10. A lubricating oil base stock comprising one or more compounds represented by the formula selected from the group consisting of

wherein R 1 and R 2 are independently a substituted or unsubstituted alkyl group (C 1 -C 30 ), R 3 , R 4 and R 13 are independently hydrogen or a substituted or unsubstituted alkyl group (C 1 -C 30 ), alkenyl group (C 1 -C 30 ), or alkoxy group (C 1 -C 30 ), R 7 is an unsubstituted aryl group (C 4 -C 30 ) and R 8 is a substituted or unsubstituted aryl group (C 4 -C 30 ), heteroaryl group (C 4 -C 30 ), or arylalkyl group (C 5 -C 30 ), R 5 , R 6 , R 9 , R 10 , R 11 and R 12 are hydrogen, m is a value from about 1 to about 10, and n is a value greater than or equal to 1; wherein said lubricating oil base stock has a viscosity (Kv 100 ) from about 1 cSt to about 10 cSt at 100° C. as determined by ASTM D445, a viscosity index (VI) from about −100 to about 300 as determined by ASTM D2270, and a Noack volatility of no greater than 50 percent as determined by ASTM D5800.

11. The lubricating oil base stock of claim 10 having a Noack volatility of no greater than Noack=[−18(Kv 100 )+70] as determined by ASTM D5800.

12. The lubricating oil base stock of claim 10 wherein R 1 and R 2 are independently a substituted or unsubstituted alkyl group (C 1 -C 20 ), R 3 , R 4 and R 13 are independently hydrogen or a substituted or unsubstituted alkyl group (C 1 -C 20 ), alkenyl group (C 1 -C 20 ), or alkoxy group (C 1 -C 20 ), R 7 is an unsubstituted aryl group (C 4 -C 20 ) and R 8 is a substituted or unsubstituted aryl group (C 4 -C 20 ), heteroaryl group (C 4 -C 20 ), or arylalkyl group (C 5 -C 20 ), R 5 , R 6 , R 9 , R 10 , R 11 and R 12 are hydrogen, m is a value from about 1 to about 9, and n is a value greater than or equal to 2.

13. The lubricating oil base stock of claim 10 wherein R 1 and R 2 are independently a substituted or u

Assignees

• Exxonmobil Res & Eng Co

Inventors

• Ng Man Kit
• Oumar-Mahamat Halou
• Cheng Hong
• Blain David A

Classifications

• C10N2030/02

  Pour-point; Viscosity index · CPC title

• C07C69/78

  Benzoic acid esters · CPC title

• C07C69/614

  of phenylacetic acid · CPC title

• C10M2207/281

  of (cyclo)aliphatic monocarboxylic acids · CPC title

• C10N2030/08

  Resistance to extreme temperature · CPC title