Methods for preparing epoxides

Abstract

The invention includes methods for preparing halohydrins and epoxides. A method of preparing halohydrins can include exposing (R 1 CHXCH 2 O—) 2 SO 2 to R 2 COOH to produce R 2 COOCH 2 CHXR 1 and hydrolyzing the R 2 COOCH 2 CHXR 1 to produce the halohydrin R 1 CHXCH 2 OH. R 1 and R 2 can be the same or different single elements and/or organic groups and X can be a halogen. A method of preparing an epoxide can include combining a sulfuric acid containing solution with a halogen to produce a first mixture and exposing the first mixture to trifluoropropene to produce a second mixture. The second mixture can be combined with acetic acid to produce an acetyl halohydrin of trifluoropropene and the acetyl halohydrin can be hydrolyzed to form a halohydrin of trifluoropropene. The halohydrin can be converted to a trifluoropropyl epoxide.

1 - 49 . (canceled)  
     
     
         50 : A method of preparing an epoxide comprising: 
 combining a sulfuric acid containing solution with a halogen to produce a first mixture;    exposing the first mixture to trifluoropropene to produce a second mixture;    combining the second mixture with acetic acid to produce an acetyl halohydrin of the trifluoropropene;    hydrolyzing the acetyl halohydrin to form a halohydrin of trifluoropropene; and    converting the halohydrin to a trifluoropropyl epoxide.    
     
     
         51 : The method of  claim 50  wherein the halogen is Br 2 , the acetyl halohydrin is acetyl bromohydrin, the sulfuric acid containing solution is oleum, and the halohydrin of trifluoropropene is the bromohydrin of trifluoropropene.  
     
     
         52 : The method of  claim 51  wherein the first mixture contains a ratio of oleum to bromine of at least 1:0.7.  
     
     
         53 : The method of  claim 51  wherein the first mixture contains a ratio of oleum to bromine of from about 1:0.7 to about 4:0.7.  
     
     
         54 : The method of  claim 51  wherein the first mixture contains a ratio of oleum to bromine of about 2:0.8.  
     
     
         55 : The method of  claim 50  wherein the exposing comprises maintaining the first mixture at a temperature of from about 12° C. to about 22° C. while bubbling the trifluoropropene into the first mixture.  
     
     
         56 : The method of  claim 51  wherein the second mixture comprises (CF 3 CHBrCH 2 O—)SO 2 .  
     
     
         57 : The method of  claim 51  wherein the hydrolyzing comprises exposing the acetyl bromohydrin to a sulfuric acid solution.  
     
     
         58 : The method of  claim 57  wherein the sulfuric acid solution comprises at least about 15% (wt./wt.) sulfuric acid.  
     
     
         59 : The method of  claim 51  wherein the converting comprises exposing the bromohydrin to a basic solution.  
     
     
         60 : The method of  claim 59  wherein the basic solution comprises at least about 20% (wt./wt.) sodium hydroxide.  
     
     
         61 : The method of  claim 59  wherein the basic solution comprises from about 40% (wt./wt.) to about 70% (wt./wt.) sodium hydroxide.  
     
     
         62 : The method of  claim 59  wherein the basic solution comprises from about 50% (wt./wt.) to about 60% (wt./wt.) sodium hydroxide.  
     
     
         63 : The method of  claim 50  wherein the converting occurs at a temperature of at least about 100° C.  
     
     
         64 : The method of  claim 50  wherein the converting occurs at a temperature of from about 100° C. to about 130° C.