Ester compounds, lubricating oil compositions containing same and processes for making same

Patent metadata

Field	Value
Publication number	US-10683464-B2
Application number	US-201816032223-A
Country	US
Kind code	B2
Filing date	Jul 11, 2018
Priority date	Sep 29, 2017
Publication date	Jun 16, 2020
Grant date	Jun 16, 2020

Abstract

This disclosure relates to ester compounds derived from neo-acids, lubricating oil base stocks comprising such ester compounds, lubricating oil compositions comprising such ester compounds, and method for making such compounds and/or base stocks. The lubricating oil base stocks comprising the ester compounds exhibit desirable lubricating properties such as polarity and oxidation stability.

First claim

What is claimed is:

1. A compound having the following formula (F-I):

wherein R 1 and R 2 are each independently a hydrocarbyl group comprising a linear or branched alkyl group of more than ten (10) carbon atoms, or a cyclic group; and
R 3 is a substituted or unsubstituted hydrocarbyl group.

2. The compound of claim 1 , wherein R 1 and R 2 are each independently a C12 to C30 linear or branched alkyl group.

3. The compound of claim 1 , wherein R 1 and R 2 are each independently a C12 to C30 linear alkyl group.

4. The compound of claim 2 , wherein R 1 and R 2 are each independently selected from n dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-icosyl, n-docosyl, n-tetracosyl, n-hexacosyl, and n-octacosyl.

5. The compound of claim 4 , wherein R 1 and R 2 are each independently selected from n-dodecyl, and n-tetradecyl.

6. The compound of claim 1 , wherein R 1 and R 2 are each independently a branched alkyl group selected from 2 propylheptanyl, 2-butyloctyl and 3,5-dimethyloctyl.

7. The compound of claim 1 , wherein R 1 and R 2 are identical.

8. The compound of claim 1 , wherein R 3 is a C1 to C24 group selected from: (a) linear or branched alkyl group, alkylaryl group, aryl group, arylalkyl group, cycloalkyl group, alkylcycloalkyl group, and cycloalkylalkyl group; and (b) substituted derivatives of those in category (a).

9. The compound of claim 8 , wherein R 3 comprises 1 to 16 carbon atoms in total.

10. The compound of claim 1 , wherein R 3 is selected from: methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-icosyl, n-docosyl, n-tetracosyl, phenyl, 1-phenylmethyl, 2-phenylmethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 6-phenylhexyl, 7-phenylheptyl, 8-phenyloctyl, 9-phenylnonyl, and 10-phenyldecyl.

11. The compound of claim 10 , wherein R 3 is selected from n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl.

12. The compound of claim 1 , which is selected from the following:
phenyl 2-ethyl-2-methylhexanoate; p-tolyl 2-ethyl-2-methylhexanoate; 3,4-dimethylphenyl 2-ethyl-2-methylhexanoate; 3,5-dimethylphenyl 2-ethyl-2-methylhexanoate; 4-ethylphenyl 2-ethyl-2-methylhexanoate; 4-propylphenyl 2-ethyl-2-methylhexanoate; 4-butylphenyl 2-ethyl-2-methylhexanoate; 4-pentylphenyl 2-ethyl-2-methylhexanoate; 4-hexylphenyl 2-ethyl-2-methylhexanoate; 4-heptylphenyl 2-ethyl-2-methylhexanoate; 4-octylphenyl 2-ethyl-2-methylhexanoate; 4-nonylphenyl 2-ethyl-2-methylhexanoate; naphthalen-2-yl 2-ethyl-2-methylhexanoate; 4-benzylphenyl 2-ethyl-2-methylhexanoate; [1,1′-biphenyl]-4-yl 2-ethyl-2-methylhexanoate;
phenyl 2-butyl-2-methyloctanoate; p-tolyl 2-butyl-2-methyloctanoate; 3,4-dimethylphenyl 2-butyl-2-methyloctanoate; 3,5-dimethylphenyl 2-butyl 2-methyloctanoate; 4-ethylphenyl 2-butyl-2-methyloctanoate; 4-propylphenyl 2-butyl-2-methyloctanoate; 4-butylphenyl 2-butyl-2-methyloctanoate; 4-pentylphenyl 2-butyl-2-methyloctanoate; 4-hexylphenyl 2-butyl-2-methyloctanoate; 4-heptylphenyl 2-butyl-2-methyloctanoate; 4-octylphenyl 2-butyl-2-methyloctanoate; 4-nonylphenyl 2-butyl-2-methyloctanoate; naphthalen-2-yl 2-butyl-2-methyloctanoate; 4-benzylphenyl 2-butyl-2-methyloctanoate; [1,1′-biphenyl]-4-yl 2-butyl-2-methyloctanoate;
butyl 2-hexyl-2-methyldecanoate; pentyl 2-hexyl-2-methyldecanoate; hexyl 2-hexyl-2-methyldecanoate; heptyl 2-hexyl-2-methyldecanoate; octyl 2-hexyl-2-methyldecanoate; nonyl 2-hexyl-2-methyldecanoate; decyl 2-hexyl-2-methyldecanoate; dodecyl 2-hexyl-2-methyldecanoate;
butyl 2-dodecyl-2-methylhexadecanoate; pentyl 2-dodecyl-2-methylhexadecanoate; hexyl 2-dodecyl-2-methylhexadecanoate; heptyl 2-dodecyl-2-methylhexadecanoate; octyl 2-dodecyl-2-methylhexadecanoate; nonyl 2-dodecyl-2-methylhexadecanoate; decyl 2-dodecyl-2-methylhexadecanoate; dodecyl 2-dodecyl-2-methylhexadecanoate; phenyl 2-dodecyl-2-methylhexadecanoate; p-tolyl 2-dodecyl-2-methylhexadecanoate; 3,4-dimethylphenyl 2-dodecyl-2-methylhexadecanoate; 3,5-dimethylphenyl 2-dodecyl-2-methylhexadecanoate; 4-ethylphenyl 2-dodecyl-2-methylhexadecanoatee; 4-propylphenyl 2-dodecyl-2-methylhexadecanoate; 4-butylphenyl 2-dodecyl-2-methylhexadecanoate; 4-pentylphenyl 2-dodecyl-2-methylhexadecanoate; 4-heptylphenyl 2-dodecyl-2-methylhexadecanoate; 4-octylphenyl 2-dodecyl-2-methylhexadecanoate; 4-nonylphenyl 2-dodecyl-2-methylhexadecanoate; naphthalen-2-yl 2-dodecyl-2-methylhexadecanoate; 4-benzylphenyl 2-dodecyl-2-methylhexadecanoate; and [1,1′-biphenyl]-4-yl 2-dodecyl-2-methylhexadecanoate.

13. A lubricating oil composition comprising a compound having the following formula (F-I):

wherein R 1 and R 2 are each independently a hydrocarbyl group comprising a linear or branched alkyl group of more than ten (10) carbon atoms, or other hydrocarbyl group; and
R 3 is a substituted or unsubstituted hydrocarbyl group.

14. The lubricating oil composition of claim 13 , which is a lubricating oil base stock.

15. The lubricating oil composition of claim 14 , which consists essentially of one or more compounds having formula (F-I).

16. The lubricating oil composition of claim 14 , having a kinematic viscosity at 100° C. as determined pursuant to ASTM D445 in the range from 1 to 40 cSt.

17. The lubricating oil composition of claim 13 , which is a lubricating oil formulation comprising a compound having formula (F-I) as a first base stock.

18. The lubricating oil composition of claim 17 , wherein the concentration of the first base stock, based on the total weight of the lubricating oil formulation, is in the range from 5 to 95 wt %.

19. A process for making an ester product comprising a compound having the following formula (F-I):

wherein R 1 and R 2 are each independently a hydrocarbyl group comprising a linear or branched alkyl group of more than ten (10) carbon atoms, or other hydrocarbyl group;
R 3 is a substituted or unsubstituted hydrocarbyl group;
the method comprising:
reacting a neo-acid having a formula (F-II) and/or an anhydride thereof with an alcohol having a formula (F-III) below in the presence of an acid catalyst to obtain a reaction mixture, where R 1 , R 2 , and R 3 correspond to the R 1 , R 2 , and R 3 in formula (F-I), respectively:

R 3 —OH (F-III), and

obtaining the ester product from the reaction mixture.

20. The process of claim 19 , wherein R 1 and R 2 are each independently a C12 to C30 linear alkyl group.

21. The process of claim 20 , wherein R 1 and R 2 are each independently selected from n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-icosyl, n-docosyl, n-tetracosyl, n-hexacosyl, and n-octacosyl.

22. The process of claim 19 , wherein R 3 is a C1 to C24 group selected from: (a) linear or branched alkyl group, alkylaryl group, aryl group, arylalkyl group, cycloalkyl group, alkylcycloalkyl group, and cycloalkylalkyl group; and (b) substituted derivatives of those in category (a).

23. The process of claim 22 , wherein R 3 is selected from: methyl, ethyl, n-pro

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Patil Abhimanyu O
• Lewis Kyle G
• Bodige Satish

Classifications

• C10M2207/281

  of (cyclo)aliphatic monocarboxylic acids · CPC title

• C07C69/003

  Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom · CPC title

• C07C45/50

  by oxo-reactions · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C10N2030/74

  Noack Volatility · CPC title