2-Oxo-1, 3-dioxolane-4-carboxylic Acid and Derivatives Thereof, Their Preparation and Use

Abstract

2-Oxo-1,3-dioxolane-4-carboxylic acid and derivatives thereof, according to the following formula, in which R 1 represents a negative charge, hydrogen or may be methyl or ethyl or an n-valent radical, which may be substituted with at most n−1 further 2-oxo-1,3-dioxolane-4-carboxyl groups, as well as a process for their preparation by means of carboxylation of the corresponding epoxides, a process for their transesterification and their use for the preparation of hydroxyurethanes and as end groups for the blocking of amines.

We claim: 
     
         1 . A process for the preparation of a hydroxyurethane, comprising reacting a 2-oxo-1,3-dioxolane-4-carboxylic acid ester according to formula (V), 
       
         
           
           
               
               
           
         
         wherein R 1  represents a negative charge, hydrogen, or a group selected from straight-chain or branched aliphatic groups, aryl groups, aralkyl groups and alkylaryl groups, 
       
       with at least one of a primary amine or a secondary amine. 
     
     
         2 . The process according to  claim 1 , wherein the at least one of a primary amine or a secondary amine has an alkyl group, aryl group, aralkyl group, or alkylaryl group as a radical. 
     
     
         3 . The process according to  claim 1 , wherein R 1  represents a C 1-12 -alkyl group, optionally wherein R 1  is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, 2-ethyl-n-hexyl, n-lauryl, cyclohexyl, phenyl and benzyl. 
     
     
         4 . The process according to  claim 1 , wherein R 1  is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, 2-ethyl-n-hexyl, n-lauryl, cyclohexyl, and phenyl. 
     
     
         5 . The process according to  claim 1 , wherein R 1  is a radical having a valency of 2 to 5 derived by abstraction of all the OH groups of a polyol having a valency of 2 to 5 and which is substituted by an amount of further 2-oxo-1,3-dioxolane-4-carboxylate groups of formula (VI) 
       
         
           
           
               
               
           
         
       
       equal to the radical valency minus 1. 
     
     
         6 . The process according to  claim 5 , wherein the polyol comprises C 2-4 -(poly)oxyalkylene groups. 
     
     
         7 . The process according to  claim 5 , wherein the polyol is selected from the group consisting of diol, glycol, triol, tetraol, 1,4-butanediol, neopentyl glycol (2,2-dimethylolpropane), 1,1,1-trimethylolpropane, pentaerythritol and tetramethylolmethane. 
     
     
         8 . The process according to  claim 7 , wherein the polyol is modified with C 2-4 -alkylene oxide. 
     
     
         9 . The process according to  claim 1 , wherein the 2-oxo-1,3-dioxolane-4-carboxylic acid ester is selected from 4-methoxycarbonyl-2-oxo-1,3-dioxolane and 4-ethoxycarbonyl-2-oxo-1,3-dioxolane. 
     
     
         10 . A process comprising blocking an amine by reaction with a 2-oxo-1,3-dioxolane-4-carboxylic acid ester according to formula (V) as an end group, 
       
         
           
           
               
               
           
         
         wherein R 1  represents a negative charge, hydrogen, or a group selected from straight-chain or branched aliphatic groups, aryl groups, aralkyl groups and alkylaryl groups. 
       
     
     
         11 . The process according to  claim 10  wherein R 1  represents a C 1-12 -alkyl group, optionally wherein R 1  is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, 2-ethyl-n-hexyl, n-lauryl, cyclohexyl, phenyl and benzyl. 
     
     
         12 . The process according to  claim 10  wherein R 1  is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, 2-ethyl-n-hexyl, n-lauryl, cyclohexyl, and phenyl.