Methods of manufacturing derivatives of beta-hydroxycarboxylic acids

Abstract

Preparation of derivatives of β-hydroxycarboxylic acid, including β-hydroxycarboxylic acid esters, α,β-unsaturated carboxylic acids, esters of α,β-unsaturated carboxylic acid, and alkoxy derivatives.

1 - 13 . (canceled) 
     
     
         14 . A method for preparing an α,β-unsaturated carboxylic acid salt, comprising: (a) providing an aqueous solution comprising a β-hydroxycarboxylic acid salt; and (b) heating the solution to dehydrate the salt and form an α,β-unsaturated carboxylic acid salt. 
     
     
         15 . A method according to  claim 14  wherein the salt is selected from the group consisting of alkali metal salts, alkaline earth metal salts, ammonium salts, alkylammonium salts, and combinations thereof. 
     
     
         16 . A method according to  claim 14  wherein the salt comprises a sodium salt. 
     
     
         17 . A method according to  claim 14  wherein the salt comprises a calcium salt. 
     
     
         18 . A method according to  claim 14  wherein the β-hydroxycarboxylic acid is selected from the group consisting of 3-hydroxypropionic acid, 3-hydroxy-2-methylpropionic acid, 3-hydroxybutanoic acid, 3-hydroxy-2-methylbutanoic acid, 3-hydroxy-2-methylpentanoic acid, 3-hydroxy-3-methylbutanoic acid, 2,3-dimethyl-3-hydroxybutanoic acid, 3-hydroxy-3-phenylpropionic acid, and combinations thereof. 
     
     
         19 . A method according to  claim 14  wherein the β-hydroxycarboxylic acid is 3-hydroxypropionic acid. 
     
     
         20 . A method according to  claim 14  wherein the aqueous solution is derived from a fermentation broth. 
     
     
         21 . A method according to  claim 14  comprising heating the aqueous solution in the presence of a dehydration catalyst to dehydrate the salt and form an α,β-unsaturated carboxylic acid salt thereof. 
     
     
         22 . A method according to  claim 14  further comprising reacting the α,β-unsaturated carboxylic acid salt, with an alcohol to form an α,β-unsaturated carboxylic acid ester. 
     
     
         23 - 49 . (canceled)