Hydrogenation with copper compositions catalyst

• US 7,491,820 B2
• Filed: 04/20/2006
• Issued: 02/17/2009
• Est. Priority Date: 04/26/2005
• Status: Expired due to Fees

• Current Assignee: Archer Daniels Midland Company
• Original Assignee: Archer Daniels Midland Company
• Inventors: Sleeter, Ronald T.
• Primary Examiner(s): Sullivan; Daniel M
• Assistant Examiner(s): CUTLIFF, YATE KAI RENE
• Application Number:
  US11/407,193
• Publication Number:
  US 20060241313A1
• Time in Patent Office: 1,034 Days
• Field of Search: 544/141, 544/144
• US Class Current: 544/144
• CPC Class Codes: B01J 23/72 Copper
• CPC Class Codes: C11C 3/126 using catalysts based principally on other metals or derivates

Abstract

Copper compositions that are useful as hydrogenation catalysts are disclosed. In particular, the copper compounds are catalysts for the selective hydrogenation of oils that contain unsaturated fatty acyl components such as unsaturated vegetable oils. Methods of preparing the copper compositions are also disclosed. Methods of hydrogenating unsaturated compositions that contain at least two sites of unsaturation using the hydrogenation catalysts, along with products obtained from the hydrogenation reactions described herein are also disclosed.

Claims

1. A process for hydrogenating a polyunsaturated compound comprising:

placing the polyunsaturated compound in contact with a hydrogenation catalyst comprising a hydrogen peroxide-treated copper carbonate/copper hydroxide material, thus producing a mixture; and

heating the mixture at a temperature between 50°

C. and 250°

C. under a hydrogen atmosphere;

thus hydrogenating the polyunsaturated compound.

2. The process of claim 1, wherein the temperature is between 100°

C. and 200°

C.

3. The process of claim 1, wherein the hydrogen atmosphere is from 5 psi to 1000 psi.

4. The process of claim 1, wherein the polyunsaturated compound contains at least two sites of unsaturation in a carbon chain.

5. The process of claim 4, wherein the polyunsaturated compound is present in a composition selected from the group consisting of vegetable fat, vegetable oil, animal fat, animal oil, synthetic fat, synthetic oil, derivatives of any thereof, and mixtures of any thereof.

6. The process of claim 5, wherein the compound is an edible oil.

7. The process of claim 6, wherein the edible oil is a vegetable oil.

8. The process of claim 7, wherein the vegetable oil is selected from the group consisting of soybean oil, linseed oil, sunflower oil, canola oil, rapeseed oil, cottonseed oil, peanut oil, safflower oil, derivatives of the oils, conjugated derivatives of the oils, and mixtures of any thereof.

9. The process of claim 7, wherein the vegetable oil is hydrogenated to contain no greater than 5% linolenic acid.

10. The process of claim 7, wherein the vegetable oil is hydrogenated to contain no greater than 10% trans fatty acid(s).

11. The process of claim 10, further comprising removing the catalyst from the mixture, wherein removing the catalyst from the mixture comprises centrifugation, settling, decantation, filtration, contact with a filter aid, contact with a liquid or solid chelating agent, addition of an activated adsorbent, or any combination thereof.

12. The process of claim 1, wherein the hydrogenated compound is a vegetable oil comprising fatty acid chains having the following profile:

C18;

2/C18;

0 ratio above 11.0;

C18;

2/C18;

1 ratio no greater than 2.2;

C18;

3/18;

0 ratio no greater than 1.7.

13. The process of claim 1, wherein the hydrogenated compound is a vegetable oil comprising fatty acid chains having the following profile:

C18;

2/18;

0 ratio above 11.3;

C18;

2/C18;

1 ratio no greater than 1.65;

C18;

3/18;

0 ratio no greater than 0.65.

14. A process for hydrogenating a composition containing at least two sites of unsaturation comprising:

placing the composition containing at least two sites of unsaturation in contact with a hydrogenation catalyst consisting essentially of a hydrogen peroxide-treated malachite material, wherein the treated malachite material has an improved ability to catalyze hydrogenation as compared to a non-treated malachite material, thus producing a mixture; and

heating the mixture at a temperature between 50°

C. and 250°

C. under a hydrogen atmosphere;

thus hydrogenating the composition.

15. A process for hydrogenating a compound containing at least two sites of unsaturation comprising:

placing the compound in contact with a hydrogenation catalyst comprising an un-supported malachite material, thus producing a mixture; and

heating the mixture at a temperature between 50°

C. and 250°

C. under a hydrogen atmosphere;

thus hydrogenating the compound.

16. A catalyst for hydrogenating a composition containing at least two sites of unsaturation, consisting essentially of hydrogen peroxide-treated copper carbonate/copper hydroxide.