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

Patent metadata

Field	Value
Publication number	US-10711216-B2
Application number	US-201816032324-A
Country	US
Kind code	B2
Filing date	Jul 11, 2018
Priority date	Sep 29, 2017
Publication date	Jul 14, 2020
Grant date	Jul 14, 2020

Abstract

This disclosure relates to ester compounds derived from neo-alcohol, 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 a formula (F-I) below:

wherein:
R 1 and R 2 are independently each a hydrocarbyl group comprising at least 2 carbon atoms; 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 C2-C30 linear or branched alkyl group.

3. The compound of claim 1 , wherein at least one of R 1 and R 2 is a linear alkyl group.

4. The compound of claim 3 , wherein at least one of R 1 and R 2 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.

5. The compound of claim 4 , wherein at least one of R 1 and R 2 is selected from n-butyl, n-hexyl, n-octyl, n-decyl, and n-dodecyl.

6. The compound of claim 1 , wherein R 1 and R 2 are independently each a linear alkyl group.

7. The compound of claim 6 , wherein R 1 and R 2 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.

8. The compound of claim 1 , wherein at least one of R 1 and R 2 is a branched alkyl group.

9. The compound of claim 8 , wherein at least one of R 1 and R 2 is selected from ethylhexyl, 2-propylheptanyl, 2-butyloctyl, and 3,5-dimethyloctyl.

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

11. 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).

12. The compound of claim 11 , wherein the category (a) groups are selected from: methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-icosyl, phenyl, benzyl, 2-phenylethyl, 3-phenylpropryl, 4-phenylbutyl, 3-(3-15 methylphenyl)propyl, 3-(p-tolyl)propyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methyl-1-naphthyl, 6-phenylhexyl, 5-pentylphenyl, 4-butylphenyl, 4-tert-butylphenyl, 7-phenylheptanyl, 4-octylphenyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, 4-phenylcyclohexyl, cyclohexylpentyl, nitrophenylmethyl, xylylmethyl, xylylpropyl, methoxyphenylethyl, methoxyphenylpropyl, methoxyphenylbutyl, nitrophenylpropyl, nitrophenylbutyl, and xylylbutyl.

13. The compound of claim 1 , which is selected from:
2-methyl-2-octyldodecyl acetate, 2-methyl-2-octyldodecyl propanoate, 2-methyl-2-octyldodecyl butanoate, 2-methyl-2-octyldodecyl pentanoate, 2-methyl-2-octyldodecyl hexanoate, 2-methyl-2-octyldodecyl octanoate, 2-methyl-2-octyldodecyl decanoate, 2-methyl-2-octyldodecyl dodecanoate, 2-methyl-2-octyldodecyl tetradecanoate, 2-methyl-2-octyldodecyl hexadecanoate, 2-methyl-2-octyldodecyl octadecanoate, 2-methyl-2-octyldodecyl icosanoate, 2-methyl-2-octyldodecyl benzoate, 2-methyl-2-octyldodecyl 4-methylbenzoate, 2-methyl-2-octyldodecyl 4-ethylbenzoate, 2-methyl-2-octyldodecyl 4-butylbenzoate, 2-methyl-2-octyldodecyl 4-pentylbenzoate, 2-methyl-2-octyldodecyl 4-hexylbenzoate, 2-methyl-2-octyldodecyl 4-heptylbenzoate, 2-methyl-2-octyldodecyl 4-octylbenzoate, 2-methyl-2-octyldodecyl [1,1′-biphenyl]-4-carboxylate, 2-methyl-2-octyldodecyl 1-naphthoate, 2-methyl-2-octyldodecyl 2-naphthoate, 2-methyl-2-octyldodecyl-3-phenylpropanoate, 2-methyl-2-octyldodecyl 2-phenylacetate, 2-methyl-2-octyldodecyl 4-phenylbutanoate, 2-methyl-2-octyldodecyl 5-phenylpentanoate, 2-methyl-2-octyldodecyl 6-phenylhexanoate, 2-methyl-2-octyldodecyl 7-phenylheptanoate;
2-methyl-2-octyldodecyl 2-methylcyclohexane-1-carboxylate, 2-methyl-2-octyldodecyl 3-methylcyclohexane-1-carboxylate, 2-methyl-2-octyldodecyl 4-methylcyclohexane-1-carboxylate, 2-methyl-2-octyldodecyl 4-(tert-butyl)cyclohexane-1-carboxylate, 2-methyl-2-octyldodecyl 4-phenylcyclohexane-1-carboxylate, 2-methyl-2-octyldodecyl 4-pentylcyclohexane-1-carboxylate;
2-butyl-2-methyloctyl acetate, 2-butyl-2-methyloctyl propanoate, 2-butyl-2-methyloctyl butanoate, 2-butyl-2-methyloctyl pentanoate, 2-butyl-2-methyloctyl hexanoate, 2-butyl-2-methyloctyl octanoate, 2-butyl-2-methyloctyl decanoate, 2-butyl-2-methyloctyl dodecanoate, 2-butyl-2-methyloctyl tetradecanoate, 2-butyl-2-methyloctyl hexadecanoate, 2-butyl-2-methyloctyl octadecanoate, 2-butyl-2-methyloctyl icosanoate, 2-butyl-2-methyloctyl benzoate, 2-butyl-2-methyloctyl 4-methylbenzoate, 2-butyl-2-methyloctyl 4-ethylbenzoate, 2-butyl-2-methyloctyl 4-butylbenzoate, 2-butyl-2-methyloctyl 4-pentylbenzoate, 2-butyl-2-methyloctyl 4-hexylbenzoate, 2-butyl-2-methyloctyl 4-heptylbenzoate, 2-butyl-2-methyloctyl 4-octylbenzoate, 2-butyl-2-methyloctyl [1,1′-biphenyl]-4-carboxylate, 2-butyl-2-methyloctyl 1-naphthoate, 2-butyl-2-methyloctyl 2-naphthoate, 2-methyl-2-octyldodecyl-3-phenylpropanoate, 2-butyl-2-methyloctyl 2-phenylacetate, 2-butyl-2-methyloctyl 4-phenylbutanoate, 2-butyl-2-methyloctyl 5-phenylpentanoate, 2-butyl-2-methyloctyl 6-phenylhexanoate, 2-butyl-2-methyloctyl 7-phenylheptanoate, 2-butyl-2-methyloctyl 2-methylcyclohexane-1-carboxylate, 2-butyl-2-methyloctyl 3-methylcyclohexane-1-carboxylate, 2-butyl-2-methyloctyl 4-methylcyclohexane-1-carboxylate, 2-butyl-2-methyloctyl 4-(tert-butyl)cyclohexane-1-carboxylate, 2-butyl-2-methyloctyl 4-phenylcyclohexane-1-carboxylate, 2-butyl-2-methyloctyl 4-pentylcyclohexane-1-carboxylate;
2-hexyl-2-methyldecyl acetate, 2-hexyl-2-methyldecyl propanoate, 2-hexyl-2-methyldecyl butanoate, 2-hexyl-2-methyldecyl pentanoate, 2-hexyl-2-methyldecyl hexanoate, 2-hexyl-2-methyldecyl octanoate, 2-hexyl-2-methyldecyl decanoate, 2-hexyl-2-methyldecyl dodecanoate, 2-hexyl-2-methyldecyl tetradecanoate, 2-hexyl-2-methyldecyl hexadecanoate, 2-hexyl-2-methyldecyl octadecanoate, 2-hexyl-2-methyldecyl icosanoate, 2-hexyl-2-methyldecyl benzoate, 2-hexyl-2-methyldecyl 4-methylbenzoate, 2-hexyl-2-methyldecyl 4-ethylbenzoate, 2-hexyl-2-methyldecyl 4-butylbenzoate, 2-hexyl-2-methyldecyl 4-pentylbenzoate, 2-hexyl-2-methyldecyl 4-hexylbenzoate, 2-hexyl-2-methyldecyl 4-heptylbenzoate, 2-hexyl-2-methyldecyl 4-octylbenzoate, 2-hexyl-2-methyldecyl [1,1′-biphenyl]-4-carboxylate, 2-hexyl-2-methyldecyl 1-naphthoate, 2-hexyl-2-methyldecyl 2-naphthoate, 2-hexyl-2-methyldecyl 3-phenylpropanoate, 2-hexyl-2-methyldecyl 2-phenylacetate, 2-hexyl-2-methyldecyl 4-phenylbutanoate, 2-hexyl-2-methyldecyl 5-phenylpentanoate, 2-hexyl-2-methyldecyl 6-phenylhexanoate, 2-hexyl-2-methyldecyl 7-phenylheptanoate, 2-hexyl-2-methyldecyl 2-methylcyclohexane-1-carboxylate, 2-hexyl-2-methyldecyl 3-methylcyclohexane-1-carboxylate, 2-hexyl-2-methyldecyl 4-methylcyclohexane-1-carboxylate, 2-hexyl-2-methyldecyl 4-(tert-butyl)cyclohexane-1-carboxylate, 2-hexyl-2-methyldecyl 4-phenylcyclohexane-1-carboxylate, 2-hexyl-2-methyldecyl 4-pentylcyclohexane-1-carboxylate;
2-decyl-2-methyltetradecyl acetate, 2-decyl-2-methyltetradecyl propanoate, 2-decyl-2-methyltetradecyl butanoate, 2-decyl-2-methyltetradecyl pentanoate, 2-decyl-2-methyltetradecyl hexanoate, 2-decyl-2-methyltetradecyl octanoate, 2-decyl-2-methyltetradecyl decanoate, 2-decyl-2-methyltetradecyl dodecanoate, 2-decyl-2-methyltetradecyl tetradecanoate, 2-decyl-2-methyltetradecyl hexadecanoate, 2-decyl-2-methyltetradecyl octadecanoate, 2-decyl-2-methyltetradecyl icosanoate, 2-decyl-2-methyltetradecyl benzoate, 2-decyl-2

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Patil Abhimanyu O
• Lewis Kyle G
• Bodige Satish

Classifications

• C07C69/24

  esterified with monohydroxylic compounds · CPC title

• C07C69/003

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

• C10N2020/071

  Branched chain compounds · CPC title

• C07C69/612

  Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety · CPC title

• C07C69/75

  of acids with a six-membered ring · CPC title