Alkylated diphenyl ether compound and lubricating oil containing said compound

Patent metadata

Field	Value
Publication number	US-9561992-B2
Application number	US-201314395880-A
Country	US
Kind code	B2
Filing date	Oct 30, 2013
Priority date	Oct 31, 2012
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

A compound of the formula (2)

wherein R 3 and R 4 are the same or different and are a branched hydrocarbon group having 10 to 26 carbon atoms, 42 to 100 mole % of the benzylic carbons of each R 3 and R 4 are quaternary, m and n are each a real number of at least zero, and 2.0≦m+n≦3.0.

First claim

The invention claimed is:

1. A compound of the formula (2)

wherein R 3 and R 4 are the same or different and are a branched hydrocarbon group having 10 to 26 carbon atoms, 42 to 100 mole % of the benzylic carbons of each R 3 and R 4 are quaternary, m and n are each a real number of at least zero, and 2.0≦m+n≦3.0; and
the compound of the formula (2) contains monoalkylated diphenyl ether in an amount of about 0.1 to 20 mole %.

2. A compound of the formula (2) obtained by an addition reaction of diphenyl ether and a branched α-olefin of the formula (1) or its corresponding branched alkyl halide

wherein R 1 and R 2 are the same or different and are a hydrocarbon group having 4 to 12 carbon atoms, R 3 and R 4 are the same or different and are a branched hydrocarbon group having 10 to 26 carbon atoms, 42 to 100 mole % of the benzylic carbons of each R 3 and R 4 are quaternary, m and n are each a real number of at least zero, and 2.0≦m+n≦3.0; and
the compound of the formula (2) contains monoalkylated diphenyl ether in an amount of about 0.1 to 20 mole %.

3. A compound of the formula (2) obtained by an addition reaction of diphenyl ether derivative of the formula (3) and a branched α-olefin of the formula (1) or its corresponding branched alkyl halide

wherein R 1 and R 2 are the same or different and are a hydrocarbon group having 4 to 12 carbon atoms, R 3 and R 4 are the same or different and are a branched hydrocarbon group having 10 to 26 carbon atoms, 42 to 100 mole % of the benzylic carbons of each R 3 and R 4 are quaternary, m and n are each a real number of at least zero, and 2.0≦m+n≦3.0; and
the compound of the formula (2) contains monoalkylated diphenyl ether in an amount of about 0.1 to 20 mole %.

4. A compound of the formula (2) as defined claim 1 wherein a ratio of the carbon at benzyl position being quaternary is 45 to 95 mole %.

5. A compound of the formula (2) as defined claim 1 wherein 50 to 90 mole % of the benzylic carbons of each R 3 and R 4 are quaternary.

6. A compound of the formula (2) as defined in claim 1 wherein 50 to 65 mole % of the benzylic carbons of each R 3 and R 4 are quaternary.

7. A compound of the formula (2) as defined in claim 1 wherein R 3 and R 4 are each 1-butyl-1-methylheptyl, 1-methyl-1-pentyloctyl, 1-hexyl-1-methylnonyl, 1-heptyl-1-methyldecyl, 1-methyl-1-octylundecyl or 1-decyl-1-methyltridecyl.

8. A compound of the formula (2) as defined in claim 1 wherein 2.0≦m+n≦2.94.

9. A lubricating oil which is usable at high temperature containing a compound of the formula (2)

wherein R 3 and R 4 are the same or different and are a branched hydrocarbon group having 10 to 26 carbon atoms, 42 to 100 mole % of the benzylic carbons of each R 3 and R 4 are quaternary, m and n are each a real number of at least zero, and 2.0≦m+n≦3.0; and
the compound of the formula (2) contains monoalkylated diphenyl ether in an amount of about 0.1 to 20 mole %.

10. A compound of the formula (2) as defined in claim 2 wherein a ratio of the carbon at benzyl position being quaternary is 45 to 95 mole %.

11. A compound of the formula (2) as defined in claim 2 wherein 50 to 90 mole % of the benzylic carbons of each R 3 and R 4 are quaternary.

12. A compound of the formula (2) as defined in claim 2 wherein 50 to 65 mole % of the benzylic carbons of each R 3 and R 4 are quaternary.

13. A compound of the formula (2) as defined in claim 2 wherein R 3 and R 4 are each 1-butyl-1-methylheptyl, 1-methyl-1-pentyl octyl, 1-hexyl-1-methylnonyl, 1-heptyl-1-methyldecyl, 1-methyl-1-octylundecyl or 1-decyl-1-methyltridecyl.

14. A compound of the formula (2) as defined in claim 2 wherein 2.0≦m+n≦2.94.

15. A compound of the formula (2) as defined in claim 3 wherein a ratio of the carbon at benzyl position being quaternary is 45 to 95 mole %.

16. A compound of the formula (2) as defined in claim 3 wherein 50 to 90 mole % of the benzylic carbons of each R 3 and R 4 are quaternary.

17. A compound of the formula (2) as defined in claim 3 wherein 50 to 65 mole % of the benzylic carbons of each R 3 and R 4 are quaternary.

18. A compound of the formula (2) as defined in claim 3 wherein R 3 and R 4 are each 1-butyl-1-methylheptyl, 1-methyl-1-pentyloctyl, 1-hexyl-1-methylnonyl, 1-heptyl-1-methyldecyl, 1-methyl-1-octylundecyl or 1-decyl-1-methyltridecyl.

19. A compound of the formula (2) as defined in claim 3 wherein 2.0≦m+n≦2.94.

Assignees

• Moresco Corp

Inventors

• Hayashi Mayumi
• Maruyama Shingo

Classifications

• C10M2207/0406

  used as base material · CPC title

• C07C43/275 Primary

  having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings · CPC title

• C10M105/18

  Ethers, e.g. epoxides · CPC title

• C07C43/263

  the aromatic rings being non-condensed · CPC title

• C10N2030/08

  Resistance to extreme temperature · CPC title