Method for producing dialkyl polysulfide, dialkyl polysulfide, extreme-pressure additive and lubricating fluid composition

Patent metadata

Field	Value
Publication number	US-10487285-B2
Application number	US-201415023862-A
Country	US
Kind code	B2
Filing date	Sep 18, 2014
Priority date	Sep 24, 2013
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

For efficiently producing a dialkyl polysulfide which is able to be favorably used as an extreme-pressure additive which does not easily corrode the metal surface, and an extreme-pressure additive and lubricating fluid composition including the dialkyl polysulfide, provided is a method for producing dialkyl polysulfide including a first step of reacting an olefin compound (a) represented by General Formula (1): R1R2C═CHR3 (where R1 and R2 each are an alkyl group, R3 is a hydrogen atom or an alkyl group, and the total number of carbon atoms of R1, R2 and R3 is 2 to 20) with sulfur in the presence of a hydrogen sulfide to thereby obtain crude dialkyl polysulfide (A), and a second step of reacting the crude dialkyl polysulfide (A) and a sulfide of an alkali metal in a solvent including an alcohol to thereby reduce the number of sulfur atoms in the crude dialkyl polysulfide (A).

First claim

The invention claimed is:

1. A method for producing dialkyl polysulfide, comprising:
a first step of reacting an olefin compound (a) represented by General Formula (1): R 1 R 2 C═CHR 3 (where R 1 and R 2 each are an alkyl group, R 3 is a hydrogen atom or an alkyl group, and the total number of carbon atoms of R 1 , R 2 and R 3 is 2 to 20) with sulfur in the presence of a hydrogen sulfide to thereby obtain a crude dialkyl polysulfide (A), and
a second step of reacting the crude dialkyl polysulfide (A) and a sulfide of an alkali metal in a solvent including an alcohol to reduce the number of sulfur atoms in the crude dialkyl polysulfide (A)
wherein, in the first step, the reaction is performed at 120° C. to 150° C. for 1 to 72 hours, and in the second step, the reaction is performed at 40° C. to 80° C. for 1 to 72 hours, and
wherein, in the second step, the content of the alcohol in the solvent including the alcohol is 45 to 75 parts by mass with respect to 100 parts by mass of the solvent; the amount of the solvent is 50 mass % to 300 mass % with respect to the mass of the sulfide of the alkali metal.

2. The method for producing dialkyl polysulfide according to claim 1 ,
wherein, in General Formula (1), the total number of carbon atoms of R 1 and R 2 is 2 to 14 and R 3 is a hydrogen atom.

3. The method for producing dialkyl polysulfide according to claim 1 ,
wherein the olefin compound (a) is diisobutylene.

4. The method for producing dialkyl polysulfide according to claim 1 ,
wherein the alcohol is ethylene glycol.

5. The method for producing dialkyl polysulfide according to claim 1 ,
wherein the first step is performed in the presence of a basic compound.

6. The method for producing dialkyl polysulfide according to claim 5 ,
wherein the basic compound is sodium hydroxide or potassium hydroxide.

7. The method for producing dialkyl polysulfide according to claim 1 ,
wherein, in the first step, the reaction of the olefin compound (a) represented by General Formula (1) with sulfur is performed at 120° C. to 130° C. for 5 to 48 hours.

8. The method for producing dialkyl polysulfide according to claim 1 ,
wherein the sulfide of an alkali metal is sodium sulfide.

9. The method for producing dialkyl polysulfide according to claim 1 ,
wherein the second step is performed in the presence of a hydroxide of an alkali metal.

10. The method for producing dialkyl polysulfide according to claim 9 ,
wherein the hydroxide of an alkali metal is sodium hydroxide or potassium hydroxide.

11. The method for producing dialkyl polysulfide according to claim 1 ,
wherein the dialkyl polysulfide is represented by General formula (2):

wherein R 1 and R 2 each are an alkyl group, R 3 is a hydrogen atom or an alkyl group, the total number of carbon atoms of one of R 1 , one of R 2 , and one of R 3 is 2 to 20, and n is an integer of 1 to 6,
the sum of the content ratio of the compound of General Formula (2) in which n is 2 and the content ratio of the compound of General Formula (2) in which n is 3 being 80 mass % to 100 mass % with respect to the total amount of the compound represented by General Formula (2).

12. An extreme-pressure additive comprising:
a dialkyl polysulfide (I) obtained by the method for producing dialkyl polysulfide according to claim 1 and further comprising
a dialkyl polysulfide other than the dialkyl polysulfide (I); and
wherein the dialkyl polysulfide other than the dialkyl polysulfide (I) is a dialkyl polysulfide (II) represented by General Formula (3):

wherein R 4 and R 5 each are a hydrogen atom or an alkyl group, the total number of carbon atoms of one of R 4 and one of R 5 is 4 to 20, and n is an integer of 1 to 6,
the sum of the content ratio of the compound of General Formula (3) in which n is 2 and the content ratio of the compound of General Formula (3) in which n is 3 being 80 mass % to 100 mass % with respect to the total amount of the compound represented by General Formula (3).

13. The extreme-pressure additive according to claim 12 ,
wherein the dialkyl polysulfide (I) is represented by General formula (2):

wherein R 1 and R 2 each are an alkyl group, R 3 is a hydrogen atom or an alkyl group, the total number of carbon atoms of one of R 1 , one of R 2 , and one of R 3 is 2 to 20, and n is an integer of 1 to 6,
the sum of the content ratio of the compound of General Formula (2) in which n is 2 and the content ratio of the compound of General Formula (2) in which n is 3 being 80 mass % to 100 mass % with respect to the total amount of the compound represented by General Formula (2).

14. A lubricating fluid composition comprising:
the extreme-pressure additive according to claim 12 ; and
a base oil.

15. A lubricating fluid composition comprising:
the extreme-pressure additive according to claim 13 ; and
a base oil.

16. The method for producing dialkyl polysulfide according to claim 3 ,
Wherein the amount of active sulfur in the dialkyl polysulfide is 0.1 mass % to 30 mass % based on the total sulfur content.

Assignees

• Dainippon Ink & Chemicals

Inventors

• Iba Takafumi
• Sakata Hiroshi

Classifications

• C07C319/22

  of hydropolysulfides or polysulfides · CPC title

• C10N2040/25

  Internal-combustion engines · CPC title

• C10N2040/08

  Hydraulic fluids, e.g. brake-fluids · CPC title

• C10N2020/071

  Branched chain compounds · CPC title

• C10M135/04

  Hydrocarbons · CPC title