Patent ID: 8367859
Filing Date: 2013-02-05
Classification: C07B,C07C,C07D,C08G

Abstract:
1. A method for preparing a compound containing a cyclohexane ring, the compound having formula (I) the method comprising: (1) in a one-pot reaction, isomerizing one or more of cis,cis and cis,trans muconic acids or carboxylate derivatives thereof to form trans,trans muconic acid or carboxylate derivatives thereof, and contacting the trans,trans muconic acid or carboxylate derivatives thereof with a dienophile in a solvent under conditions such that one or more cyclohexene ring containing compounds having carboxylate groups at the 1 and 4 position are formed; and (2) contacting the one or more cyclohexene ring containing compounds having carboxylate groups at the 1 and 4 position with hydrogen in the presence of one or more hydrogenation catalysts under conditions such that one or more compounds of formula (I) containing a cyclohexane ring having carboxylate groups at the 1 and 4 position are prepared, wherein the cyclohexene ring containing compounds contain up to about 1 part per trillion of Carbon 14 as determined according to ASTM D6866-08, and 6 or more of the carbon atoms are derived from a muconate microbially synthesized from a biomass; wherein said carboxylate derivatives contain group wherein: R R R or R Z is independently in each occurrence an anion, oxygen, nitrogen, sulfur, nitrile or a halogen; and b is independently in each occurrence 0, 1 or 2 with the proviso that b is 0 when Z is an anion, halogen or nitrile; b is 1 when Z is oxygen or sulfur; and b is 2 when Z is nitrogen.