IP Library Granted Patent US 9,035,094
Granted Patent B2
US 9,035,094 · App. 13/915,120 · Granted May 19, 2015

Process for production of adipic acid from 1,6-hexanediol

Inventors: Eric L. Dias (Belmont, CA); Vincent J. Murphy (San Jose, CA); James A. W. Shoemaker (Gilroy, CA)
Assignee: Rennovia, Inc.
C07C51/235B01J23/42B01J23/52B01J23/44B01J35/0006B01J21/066B01J23/6527B01J23/687B01J35/1014B01J35/1061
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,035,094
App. No.
13/915,120
Granted
May 19, 2015
Kind
B2
Abstract

Processes are disclosed for the conversion of 1,6-hexanediol to adipic acid employing a chemocatalytic reaction in which 1,6-hexanediol is reacted with oxygen in the presence of particular heterogeneous catalysts including at least one of platinum or gold. The metals are preferably provided on a support selected from the group of titania, stabilized titania, zirconia, stabilized zirconia, silica or mixtures thereof, most preferably zirconia stabilized with tungsten. The reaction with oxygen is carried out at a temperature from about 100° C. to about 300° C. and at a partial pressure of oxygen from about 50 psig to about 2000 psig.

Claims (37)

1. A process for preparing an adipic acid product, the process comprising chemocatalytically converting 1,6-hexanediol to the adipic acid product by a method comprising reacting the 1,6-hexanediol with oxygen in the presence of a heterogenous catalyst comprising gold and platinum on a support, wherein the support is selected from the group consisting of silica, carbon, zirconia, titania, metal oxide-composite and mixtures thereof.

2. A process for preparing an adipic acid product, the process comprising reacting 1,6-hexanediol and oxygen in the presence of a heterogeneous catalyst comprising gold on a support, wherein the support is selected from the group consisting of silica, carbon, zirconia, titania, alumina, metal oxide-composite and mixtures thereof, and wherein the weight percent of gold to the total weight of the finished catalyst is from about 0.1 wt % to about 10 wt %.

3. The process of claim 1 , wherein the heterogeneous catalyst comprises a support, the outer surfaces of the support comprising a material selected from the group consisting of zirconia, stabilized zirconia, zirconia-metal or -metal oxide composites, titania, stabilized titania, titania-metal or -metal oxide composites, silica and mixtures thereof.

4. The process of claim 2 , wherein the surface area of the support is equal to or less than about 220 m 2 /g and the average pore diameter is at least about 5 nm.

5. The process of claim 3 , wherein the support is a zirconia or stabilized zirconia support and further comprises tungsten.

6. The process of claim 1 , wherein the heterogeneous catalyst comprises a support selected from the group consisting of zirconia, stabilized zirconia, stabilized zirconia-metal or zirconia-metal oxide composite, titania, stabilized titania, stabilized titania-metal or titania-metal oxide composite, and mixtures thereof.

7. The process of claim 5 , wherein the tungsten is present in an amount ranging from about 1 wt % to about 15 wt % of the total weight of the support.

8. The process of claim 6 , wherein the support has a surface area equal to or less than about 220 m 2 /g and an average pore diameter of at least about 5 nm.

9. The process of claim 6 , wherein the support has a surface area equal to or less than about 100 m 2 /g and an average pore diameter of at least about 10 nm.

10. The process of claim 1 , wherein reacting the 1,6-hexanediol with oxygen in the presence of the heterogeneous catalyst comprises:

a) combining the 1,6-hexanediol and the heterogeneous catalyst, and optionally a solvent; and

b) contacting the combined 1,6-hexanediol and heterogeneous catalyst, and optionally the solvent, with oxygen.

11. The process of claim 1 , wherein reacting the 1,6-hexanediol with oxygen in the presence of the heterogeneous catalyst and, optionally a solvent comprises:

a) combining the 1,6-hexanediol and the heterogeneous catalyst, and optionally a solvent, at a temperature equal to or less than about 120° C. ; and

b) contacting with oxygen the combined 1,6-hexanediol and heterogeneous catalyst, and optionally the solvent.

12. The process of claim 1 , wherein reacting the 1,6-hexanediol with oxygen in the presence of the heterogeneous catalyst comprises:

a) combining the 1,6-hexanediol and a solvent;

b) contacting the combined 1,6-hexanediol and solvent with a heterogeneous catalyst; and

c) contacting the combined 1,6-hexanediol, solvent, and heterogeneous catalyst with oxygen.

13. The process of claim 11 , wherein the solvent is selected from the group consisting of water, alcohols, ethers, and mixtures thereof.

14. The process of claim 1 , wherein reacting the 1,6-hexanediol with oxygen in the presence of the heterogeneous catalyst and water comprises:

a) contacting the 1,6-hexanediol with water;

b) contacting the 1,6-hexanediol and water with the heterogeneous catalyst; and,

c) contacting the combined 1,6-hexanediol, water, and heterogeneous catalyst with oxygen.

15. The process of claim 3 , wherein the reaction is conducted under a partial pressure of oxygen ranging from about 50 psi to about 2000 psi.

16. The process of claim 3 , wherein the partial pressure of oxygen ranges from about 50 psig to about 1000 psig.

17. The process of claim 1 , wherein the reacting the 1,6-hexanediol with oxygen in the presence of a heterogeneous catalyst is carried out at a temperature ranging from about 100° C. to about 180° C.

18. The process of claim 4 , wherein the reacting the 1,6-hexanediol with oxygen in the presence of a heterogeneous catalyst is carried out at a temperature ranging from about 135° C. to about 165° C.

19. The process of claim 1 , wherein the catalyst further comprises palladium.

20. The process of claim 1 , wherein the ratio of platinum to gold is from about 10:1 to about 1:1.

21. The process of claim 1 , wherein the total weight percent of platinum and gold is from about 0.2 wt % to about 5 wt % of the total weight of the catalyst.

22. The process of claim 1 , wherein the total weight percent of platinum and gold is equal to or less than about 4 wt % of the total weight of the catalyst.

23. The process of claim 2 , wherein the total weight percent of gold is from about 0.2 wt % to about 5 wt % of the total weight of the catalyst.

24. The process of claim 2 , wherein the total weight percent of gold is equal to or less than about 4 wt % of the total weight of the catalyst.

25. The process of claim 1 , wherein the support is selected from the group consisting of silica, carbon and zirconia.

26. The process of claim 2 , wherein the support is selected from the group consisting of silica, carbon and zirconia.

27. The process of claim 11 , wherein the solvent is water.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2018
From: RENNOVIA INC.
To: ARCHER-DANIELS-MIDLAND COMPANY
Reel/Frame 045385/0614 →
RELEASE OF SECURITY INTEREST Recorded Feb 15, 2018
From: PACIFIC WESTERN BANK
To: RENNOVIA INC.
Reel/Frame 044946/0264 →
SECURITY INTEREST Recorded Jan 23, 2018
From: RENNOVIA INC.
To: PACIFIC WESTERN BANK
Reel/Frame 044703/0960 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2013
From: DIAS, ERIC L.; MURPHY, VINCENT J.; SHOEMAKER, JAMES A.W.
To: RENNOVIA, INC.
Reel/Frame 030685/0225 →
Continuity (2)
Provisional Application 61658364 · Jun 11, 2012
Related Publication 20130331606A1 · Dec 12, 2013