Process for converting disulfides to conversion products and process for producing cysteic acid

Abstract

Embodiments of the present disclosure generally relate to processes for converting disulfides to conversion products and to processes for producing cysteic acid. In an embodiment, a process for converting cystine to a conversion product is provided. The process include introducing an organic peroxide and water to cystine to form a mixture. The process further includes reacting the mixture, under conversion conditions, to form the conversion product, wherein the conversion product comprises cysteic acid, an amount of cysteic acid in the conversion product is greater than about 90 wt % based on a total weight of the conversion product, and the conversion conditions comprise a conversion temperature from about 15° C. to about 50° C. The process further includes heating the conversion product to remove the organic peroxide.

What is claimed is: 
     
         1 . A process for converting cystine to a conversion product, comprising:
 reacting a mixture of an organic peroxide and cystine, under conversion conditions, to form the conversion product, wherein:
 the conversion product comprises cysteic acid; 
 an amount of cysteic acid in the conversion product is greater than 75 wt % based on a total weight of the conversion product; and 
 the conversion conditions comprise a conversion temperature of less than 95° C. 
   
     
     
         2 . The process of  claim 1 , wherein the conversion temperature is less than 80° C. 
     
     
         3 . The process of  claim 1 , wherein the organic peroxide is formed by introducing an organic acid to hydrogen peroxide. 
     
     
         4 . The process of  claim 3 , wherein the organic acid is a substituted or unsubstituted, branched or unbranched, cyclic or acyclic C 1 -C 40  organic acid. 
     
     
         5 . The process of  claim 3 , wherein the organic acid comprises acetic acid, formic acid, benzoic acid, triflouroacetic acid, propanoic acid, or butanoic acid. 
     
     
         6 . The process of  claim 1 , wherein the conversion product is heated to remove at least a portion of any remaining organic peroxide. 
     
     
         7 . The process of  claim 6 , wherein heating the conversion product to remove the organic peroxide includes heating the conversion product to a temperature of about 80° C. or less. 
     
     
         8 . The process of  claim 1 , wherein the conversion product is placed under a pressure of less than about 1 atm to remove at least a portion of any remaining organic peroxide. 
     
     
         9 . The process of  claim 1 , wherein a percent conversion of cystine to cysteic acid is about 50% or more. 
     
     
         10 . A process for converting an organic disulfide to a conversion product, comprising:
 reacting a mixture of an organic acid, hydrogen peroxide, and the organic disulfide, under conversion conditions, to form the conversion product, wherein
 the organic disulfide has the formula R 1 —S—S—R 2 , wherein each of R 1  and R 1  are, independently, a C 1 -C 100  unsubstituted hydrocarbyl or a C 1 -C 100  substituted hydrocarbyl; 
 the conversion product comprises a sulfonic acid; and 
 an amount of sulfonic acid in the conversion product is greater than 75 wt % based on a total weight of the conversion product. 
   
     
     
         11 . The process of  claim 10 , wherein R 1  and R 2  are the same. 
     
     
         12 . The process of  claim 10 , wherein at least a portion of any remaining organic peroxide is removed by evaporation. 
     
     
         13 . The process of  claim 10 , wherein a molar ratio of the organic acid to the organic disulfide in the mixture is from about 20:1 to about 1:1 
     
     
         14 . The process of  claim 10 , wherein the organic acid is a substituted or unsubstituted, branched or unbranched, cyclic or acyclic C 1 -C 40  organic acid. 
     
     
         15 . A process, comprising:
 reacting a mixture of an organic acid, hydrogen peroxide, and an organic disulfide to form a conversion product, the organic disulfide having the formula R 1 —S—S—R 2 , each of R 1  and R 2  are, independently, a C 1 -C 100  unsubstituted hydrocarbyl or a C 1 -C 100  substituted hydrocarbyl, R 1  and R 2  being the same or different.   
     
     
         16 . The process of  claim 15 , wherein the conversion product comprises an amount of a sulfonic acid of 75 wt % or more. 
     
     
         17 . The process of  claim 15 , wherein a percent conversion of the organic disulfide to the conversion product is 50% or more. 
     
     
         18 . The process of  claim 15 , wherein the organic acid is a substituted or unsubstituted, branched or unbranched, cyclic or acyclic C 1 -C 40  organic acid. 
     
     
         19 . The process of  claim 15 , wherein the reacting is performed at a temperature of 0° C. to 95° C. 
     
     
         20 . The process of  claim 15 , wherein a molar ratio of the organic acid to the hydrogen peroxide in the mixture is from 3:1 to 1:3.