Process for preparing alkanesulfonic acids

Patent metadata

Field	Value
Publication number	US-2016304446-A1
Application number	US-201415103784-A
Country	US
Kind code	A1
Filing date	Dec 10, 2014
Priority date	Dec 11, 2013
Publication date	Oct 20, 2016
Grant date	—

Abstract

The present invention relates to a process for preparing alkanesulfonic acids from dialkyl disulfides with nitric acid and oxygen.

First claim

1 . A process for preparing an alkanesulfonic acid of the formula R—SO 3 —H, comprising:
oxidizing a symmetrical dialkyl disulfide of the formula R—S 2 —R, in solution in an alkanesulfonic acid, in the presence of a catalytic amount of nitric acid, with R denoting a C 1 -C 12 alkyl radical and the alkanesulfonic acid used as solvent being identical with the alkanesulfonic acid obtained from the oxidation of the dialkyl disulfide,
wherein the concentration of the dialkyl disulfide in the solution is not more than 20 weight percent, the ratio of dialkyl disulfide to nitric acid ranges from 2000:1 (mol/mol) to 1:1 (mol/mol), and the concentration of the alkanesulfonic acid used as solvent is more than 70 weight percent.

2 . The process according to claim 1 , wherein the dialkyl disulfide is dimethyl disulfide and the alkanesulfonic acid is methanesulfonic acid.

3 . The process according to claim 1 , wherein the ratio of dialkyl disulfide to nitric acid ranges from 500:1 (mol/mol) to 1:1 (mol/mol).

4 . The process according to claim 1 , wherein the ratio of dialkyl disulfide to nitric acid ranges from 500:1 (mol/mol) to 2:1 (mol/mol).

5 . The process according to claim 1 , wherein the concentration of the dialkyl disulfide in the alkanesulfonic acid is up to about 10 weight percent.

6 . The process according to claim 1 , wherein the process is carried out at temperatures of not more than about 90° C.

7 . The process according to claim 6 , wherein the process is carried out at temperatures of about 70° C. to about 90° C.

8 . The process according to claim 1 , wherein the concentration of the alkanesulfonic acid used as solvent is at least 80 weight percent.

9 . The process according to claim 8 , wherein the concentration of the alkanesulfonic acid used as solvent is at least about 90 weight percent.

10 . The process according to claim 1 , wherein, for the oxidation, air, a gas stream enriched with oxygen in free form, and/or pure oxygen in free form is fed in.

11 . The process according to claim 10 , wherein, for the oxidation, a gas stream comprising oxygen, containing more than 21 vol.-% of oxygen in free form, is fed in.

12 . The process according to claim 1 , wherein the process is carried out at a pressure of more than 1 bara to about 20 bara.

13 . The process according to claim 12 , wherein the process is carried out at a pressure of more than 2 bara to about 15 bara.

14 . The process according to claim 1 , wherein a solubilizer between the dialkyl disulfide and the alkanesulfonic acid is used.

15 . The process according to claim 14 , wherein alkanesulfonic acid S-alkyl ester of the formula R—SO 2 —S—R is used as solubilizer between the dialkyl disulfide and the alkanesulfonic acid, with the alkyl radicals of the alkanesulfonic acid S-alkyl ester being identical with the alkyl radicals of the dialkyl disulfide to be converted and with the alkyl radical of the alkanesulfonic acid.

Assignees

• Fonfe Benjamin
• Jakob Harald
• He Chuanhua
• Doerflein Andreas
• Fuss Sebastian
• Evonik Degussa Gmbh

Inventors

• Fonfe Benjamin
• Jakob Harald
• He Chuanhua
• Doerflein Andreas
• Fuss Sebastian

Classifications

• C07C303/16 Primary

  by oxidation of thiols, sulfides, hydropolysulfides, or polysulfides with formation of sulfo or halosulfonyl groups · CPC title

• C07C309/04

  containing only one sulfo group · CPC title