Dialkyl sulfide, method for producing dialkyl sulfide, extreme-pressure additive, and lubricating fluid composition

Patent metadata

Field	Value
Publication number	US-10894767-B2
Application number	US-201615774359-A
Country	US
Kind code	B2
Filing date	Oct 27, 2016
Priority date	Dec 18, 2015
Publication date	Jan 19, 2021
Grant date	Jan 19, 2021

Abstract

An object of the present invention is to provide a dialkyl sulfide which can effectively form a metal sulfide film on a metal surface even in a low-temperature environment, has excellent storage stability, and is suitable as an extreme-pressure additive. The present invention provides a dialkyl sulfide represented by general formula (1) below (in the formula, R 1 and R 2 each independently represent an alkyl group, and n is an integer), wherein the content of a compound having an n value of 1 in the general formula (1) is 10.0% by mass or less relative to the total amount of compounds represented by the general formula (1)

First claim

The invention claimed is:

1. A dialkyl sulfide represented by general formula (1) below

(in the formula, R 1 and R 2 each independently represent an alkyl group, and n is an integer),
wherein the content of a compound having an n value of 1 in the general formula (1) is 10.0% by mass or less relative to the total amount of compounds represented by the general formula (1), the total of the content of a compound having an n value of 2 in the general formula (1), the content of a compound having an n value of 3, and the content of a compound having an n value of 4 is 50.0% to 70.0% by mass relative to the total amount of compounds represented by the general formula (1), and the total of the content of a compound having an n value of 5 in the general formula (1), the content of a compound having an n value of 6, the content of a compound having an n value of 7, and the content of a compound having an n value of 8 is 30.0% to 40.0% by mass relative to the total amount of compounds represented by the general formula (1).

2. The dialkyl sulfide according to claim 1 , wherein the content of a compound having an n value of 1 in the general formula (1) is 0.5% to 5% by mass relative to the total amount of compounds represented by the general formula (1), the total of the content of a compound having an n value of 2 in the general formula (1), the content of a compound having an n value of 3, and the content of a compound having an n value of 4 is 50.0% to 65.0% by mass relative to the total amount of compounds represented by the general formula (1), and the total of the content of a compound having an n value of 5 in the general formula (1), the content of a compound having an n value of 6, the content of a compound having an n value of 7, and the content of a compound having an n value of 8 is 30.0% to 40.0% by mass relative to the total amount of compounds represented by the general formula (1).

3. The dialkyl sulfide according to claim 1 , wherein R 1 and R 2 are each a linear alkyl group having 4 to 20 carbon atoms.

4. The dialkyl sulfide according to claim 3 , wherein R 1 and R 2 are each an octyl group.

5. A method for producing a dialkyl sulfide, the method comprising a first step of reacting a monosubstituted 1-olefin compound (a) with sulfur (b) in the presence of hydrogen sulfide (c) at a molar ratio [(a)/(b)] within a range of 0.6 to 2 in a reaction system of 60° C. to 130° C.; and a second step of maintaining the reaction system at 160° C. to 200° C.

6. The method for producing dialkyl sulfide according to claim 5 , wherein the monosubstituted 1-olefin compound (a) is reacted with sulfur (b) at a molar ratio [(a)/(b)] within a range of 0.65 to 1.7.

7. The method for producing dialkyl sulfide according to claim 5 , wherein the first step is a step of reacting the monosubstituted 1-olefin compound (a) with sulfur (b) at a molar ratio [(a)/(b)] within a range of 0.65 to 1.7 at 80° C. to 130° C.

8. The method for producing dialkyl sulfide according to claim 5 , wherein the second step is a step of maintaining the reaction system at 170° C. to 180° C. for 5 to 20 hours.

9. The method for producing dialkyl sulfide according to claim 5 , wherein the monosubstituted 1-olefin compound (a) is a monosubstituted 1-olefin compound having a linear alkyl group and 6 to 22 carbon atoms.

10. The method for producing dialkyl sulfide according to claim 5 , wherein the monosubstituted 1-olefin compound (a) is 1-decene.

11. The method for producing dialkyl sulfide according to claim 5 , wherein the monosubstituted 1-olefin compound (a) is reacted with the sulfur (b) in the presence of a basic catalyst.

12. The method for producing dialkyl sulfide according to claim 11 , wherein the basic catalyst is an aliphatic amine compound or an alkali metal hydroxide.

13. An extreme-pressure additive comprising the dialkyl sulfide according to claim 1 .

14. A lubricating fluid composition comprising the dialkyl sulfide according to claim 1 .

15. An extreme-pressure additive comprising the dialkyl sulfide according to claim 2 .

16. An extreme-pressure additive comprising the dialkyl sulfide according to claim 3 .

17. An extreme-pressure additive comprising the dialkyl sulfide according to claim 4 .

18. A lubricating fluid composition comprising the dialkyl sulfide according to claim 2 .

19. A lubricating fluid composition comprising the dialkyl sulfide according to claim 3 .

20. A lubricating fluid composition comprising the dialkyl sulfide according to claim 4 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• YONEDA Yuuki
• Sakata Hiroshi

Classifications

• C07B61/00 Primary

  Other general methods · CPC title

• C10M135/22

  containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms · CPC title

• C10M2219/082

  containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms · CPC title

• C10N2030/06

  Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure · CPC title

• C07C319/16 Primary

  by addition of hydrogen sulfide or its salts to unsaturated compounds · CPC title