Method to convert fermentation mixture into fuels

Patent metadata

Field	Value
Publication number	US-9856427-B2
Application number	US-201214123064-A
Country	US
Kind code	B2
Filing date	Apr 26, 2012
Priority date	May 27, 2011
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

The present disclosure provides methods to produce ketones suitable for use as fuels and lubricants by catalytic conversion of an acetone-butanol-ethanol (ABE) fermentation product mixture that can be derived from biomass.

First claim

What is claimed is:

1. A method of producing two or more compounds of Formula I,

wherein each R 1 and R 2 is independently an optionally substituted member selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and arylalkyl,
wherein the method comprises:
a) contacting biomass or sugars with a fermentation host to produce a fermentation product mixture, wherein the fermentation product mixture comprises acetone and two or more optionally substituted primary alcohols;
b) combining the fermentation product mixture with metal-based catalyst in the presence of base, wherein the metal-based catalyst comprises rhodium, palladium, iridium, or platinum, or a combination thereof; and
c) producing two or more compounds of Formula I, wherein at least two of the two or more compounds of Formula I are double-alkylated.

2. The method of claim 1 , wherein each R 1 and R 2 is independently an optionally substituted C1-C20 alkyl.

3. The method of claim 1 , wherein the biomass or sugars and the fermentation host are further contacted with an extractant having one or more of the following properties:
i) is non-toxic to Clostridium;
ii) has partition coefficients for acetone and butanol equal to or greater than 1; and
iii) has a partition coefficient for ethanol of less than 0.5.

4. The method of claim 3 , wherein the extractant is glyceryl tributyrate, glyceryl tripropionate, oleyl alcohol, polypropylene glycol, or a combination thereof.

5. The method of claim 1 , wherein the fermentation product mixture has less than 5 wt % water.

6. The method of claim 1 , wherein the fermentation product mixture comprises acetone, butanol, and ethanol.

7. The method of claim 1 , wherein the metal-based catalyst comprises palladium supported or tethered on a solid support.

8. The method of claim 1 , wherein the metal-based catalyst comprises Pd(OAc) 2 , Pd 2 (dba) 3 , Pd(OH) 2 /C, Pd/C, Pd/CaCO 3 , Pd/Alumina, or Pd-polyethylenimines on silica.

9. The method of claim 1 , wherein the base is K 3 PO 4 , KOH, Ba(OH) 2 .8H 2 O, K 2 CO 3 , KOAc, KH 2 PO 4 , Na 2 HPO 4 , pyridine, Et 3 N, or a combination thereof.

10. The method of claim 1 , wherein the two or more compounds of Formula I are produced at a temperature between 110° C. to 145° C.

11. The method of claim 1 , wherein the two or more compounds of Formula I are produced at a temperature between 140° C. to 220° C.

12. The method of claim 1 , wherein the yield of the two or more compounds of Formula I relative to the amount of acetone present in the fermentation product mixture is at least 10%.

13. The method of claim 1 , wherein the yield of the double-alkylated compounds of Formula I relative to the amount of acetone present in the fermentation product mixture is at least 10%.

14. The method of claim 13 , wherein the metal-based catalyst comprises Pd(OAc) 2 , Pd 2 (dba) 3 , Pd(OH) 2 /C, Pd/C, Pd/CaCO 3 , Pd/Alumina, Pd-polytheylenimines on silica, PtCl 2 (COD), [Rh(COD)Cl] 2 , or Pt/C.

Assignees

• Toste F Dean
• Anbarasan Pazhamalai
• Binder Joseph B
• Willems Paul A
• Clark Douglas S
• Baer Zach
• Sreekumar Sanil
• Blanch Harvey W
• Univ California
• Bp Corp North America Inc

Inventors

• Toste F Dean
• Anbarasan Pazhamalai
• Binder Joseph B
• Willems Paul A
• Clark Douglas S
• Baer Zach
• Sreekumar Sanil
• Blanch Harvey W

Classifications

• C12P7/26

  Ketones · CPC title

• Y02E50/10

  Biofuels, e.g. bio-diesel · CPC title

• C12P7/16

  Butanols · CPC title

• C07C49/04

  Saturated compounds containing keto groups bound to acyclic carbon atoms · CPC title

• C10L1/02 Primary

  essentially based on components consisting of carbon, hydrogen, and oxygen only · CPC title