Materials and methods for producing alkenes and derivatives thereof

Abstract

The present disclosure relates to processes for production of alkene products from their alkene precursors, such as 3-hydroxyacid and alcohols, via either (1) high temperature reactive distillation with steam contact at optimal pH, (2) solvent extraction and Mulzer dehydration, (3) solid phase adsorption, desorption into an organic solvent and catalytic reaction and (4) high temperature reactive distillation with steam contact at optimal pH followed by catalytic conversion.

1 - 18 . (canceled) 
     
     
         19 . A method producing an alkene product comprising:
 (a) extracting fermentation broth to produce an extracted alkene precursor mixture; and   (b) implementing a dehydration reaction to produce from the extracted alkene precursor mixture an alkene product mixture comprising the alkene product.   
     
     
         20 . The method of  claim 19 , further comprising a polishing distillation step after step (b). 
     
     
         21 . The method of  claim 19 , wherein the extraction step (a) comprises contacting the fermentation broth with a solvent to extract the at least one alkene precursor. 
     
     
         22 . The method of  claim 21 , wherein the solvent is selective for 3-hydroxyacids and secondary alcohols, largely immiscible in water and supports Mulzer dehydration reactions. 
     
     
         23 . The method of  claim 22 , wherein the solvent comprises a long chain ester. 
     
     
         24 . The method of  claim 23 , wherein the long chain ester solvent comprises at least one of hexyl acetate and octanyl acetate. 
     
     
         25 . The method of  claim 22 , wherein the 3-hydroxyacid precursor to an alkene product is chosen from mevalonate, 3-methyl-3-hydroxybutyrate, 3-hydroxypent-4-enoate, 3-methyl-3-hydroxypent-4-enoate and 4-methyl-3-hydroxypent-4-enoate. 
     
     
         26 . The method of  claim 22 , wherein the alcohol precursor to an alkene product is chosen from 3-methyl-2-buten-1-ol, 3-methyl-3-buten-1-ol, 2-methyl-3-buten-2-ol, 3-buten-2-ol and 3-methyl-3-buten-2-ol. 
     
     
         27 . The method of  claim 19 , wherein the alkene product is chosen from isoprene, 1,3-butadiene, and isobutene. 
     
     
         28 . The method of  claim 19 , wherein the dehydration reaction comprises contacting the extracted alkene precursor mixture and a Mulzer dehydrating agent. 
     
     
         29 . The method of  claim 28 , wherein the Mulzer dehydrating agent is dimethyl-formamide-dimethylacetal. 
     
     
         30 . The method of  claim 19 , further comprising separating the alkene product from the alkene product mixture. 
     
     
         31 . The method of  claim 30 , wherein the alkene product is separated from the alkene product mixture by at least one of adsorption, membrane separation, and distillation. 
     
     
         32 . The method of  claim 31 , wherein the alkene product is separated from the alkene product mixture by adsorption. 
     
     
         33 . The method of  claim 32 , wherein the alkene product is separated from the alkene product mixture by adsorption to a zeolite. 
     
     
         34 . The method of  claim 31 , wherein the alkene product is separated from the alkene product mixture by membrane separation. 
     
     
         35 . The method of  claim 34 , wherein the alkene product is separated from the alkene product mixture using a zeolite membrane. 
     
     
         36 . The method of  claim 31 , further comprising condensing the alkene product. 
     
     
         37 - 77 . (canceled)