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

Patent metadata

Field	Value
Publication number	US-11078140-B2
Application number	US-202017008640-A
Country	US
Kind code	B2
Filing date	Sep 1, 2020
Priority date	Jan 6, 2016
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

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.

First claim

What is claimed is:

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, wherein the term ester of poly-(R)-3-hydroxybutyrate refers to an ester formed by reaction of poly-(R)-3-hydroxybutyrate with an alcohol and wherein the term skeletal copper-based catalyst refers to a porous catalytic alloy based material comprising copper and aluminum.

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 any one of claims 1 - 3 , 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.

Assignees

• Archer Daniels Midland Co

Inventors

• Bloom Paul D
• Ma chi-cheng
• Martin Kevin J
• Smith Brennan

Classifications

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C29/149 Primary

  with hydrogen or hydrogen-containing gases · CPC title

• B01J25/02

  Raney nickel · CPC title

• C07B2200/07

  Optical isomers · CPC title

• B01J25/00

  Catalysts of the Raney type · CPC title