Process for producing 1,3-butanediol and for optionally further producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate

Abstract

A process is described for producing 1,3-butanediol, wherein an ester of poly-(R)-3-hydroxybutyrate such as formed by transesterification with an alcohol is reduced by hydrogenation in the presence of a skeletal copper-based catalyst to provide 1,3-butanediol. The 1,3-butanediol may be transesterified by reaction with additional poly-(R)-3-hydroxybutyrate ester to produce (R)-3-hydroxybutyl (R)-3-hydroxybutyrate.

1 . A process for producing 1,3-butanediol, comprising contacting an ester of poly-(R)-3-hydroxybutyrate with a source of hydrogen in the presence of a skeletal copper-based catalyst under elevated temperature conditions. 
     
     
         2 . The process of  claim 1 , wherein the ester of poly-(R)-3-hydroxybutyrate is a methyl, ethyl, propyl, butyl, pentyl or hexyl ester. 
     
     
         3 . The process of  claim 2 , wherein the ethyl ester is used. 
     
     
         4 . The process of  claim 1 , wherein the process is conducted continuously, using a fixed catalyst bed. 
     
     
         5 . The process of  claim 4 , wherein the skeletal copper-based catalyst is a promoted or unpromoted copper-aluminum alloy catalyst containing from 10 to 60 weight percent of aluminum and with the balance consisting of copper and any promoters present. 
     
     
         6 . The process of  claim 5 , wherein the catalyst contains from 20 to 55 weight percent of aluminum. 
     
     
         7 . The process of  claim 1 , conducted at a reactor temperature between 120 degrees Celsius and 220 degrees Celsius, a liquid hourly space velocity of from 0.1 hr −1  to 2 hr −1  and a hydrogen supply at a pressure of from 5.5 MPa, gauge to 17.2 MPa, gauge. 
     
     
         8 . The process of  claim 7 , conducted at a reactor temperature between 150 degrees Celsius and 220 degrees Celsius, a liquid hourly space velocity of from 0.2 hr −1  to 1 hr −1  and a hydrogen supply at a pressure of from 8.3 MPa, gauge to 12.4 MPa, gauge. 
     
     
         9 . The process of  claim 8 , conducted at a reactor temperature between 160 degrees Celsius and 200 degrees Celsius, a liquid hourly space velocity of from 0.2 hr −1  to 1 hr −1  and a hydrogen supply at a pressure of from 9.7 MPa, gauge to 12.4 MPa, gauge. 
     
     
         10 . A process for producing (R)-3-hydroxybutyl (R)-3-hydroxybutyrate, comprising:
 contacting poly-(R)-3-hydroxybutyrate with an alcohol under transesterification conditions for transesterifying the poly-(R)-3-hydroxybutyrate and producing an ester of the alcohol and poly-(R)-3-hydroxybutyrate;   separating the product of the transesterification step into first and second portions comprising the ester of the alcohol and poly-(R)-3-hydroxybutyrate;   reducing the first portion of the poly-(R)-3-hydroxybutyrate ester through a process according to any one of  claims 1 - 9  to produce 1,3-butanediol;   contacting the 1,3-butanediol with the second portion of the poly-(R)-3-hydroxybutyrate ester under transesterification conditions for producing (R)-3-hydroxybutyl (R)-3-hydroxybutyrate.