Hydrogenation Process and High Monoene Compositions Obtained Therefrom

• US 20080091039A1
• Filed: 10/12/2007
• Published: 04/17/2008
• Est. Priority Date: 10/13/2006
• Status: Abandoned Application

• Current Assignee: Archer Daniels Midland Company
• Original Assignee: Archer Daniels Midland Company
• Inventors: SLEETER, Ronald T.
• Application Number:
  US11/871,747
• Publication Number:
  US 20080091039A1
• Time in Patent Office: Days
• US Class Current: 554/145
• CPC Class Codes: B01J 23/72 Copper
• CPC Class Codes: B01J 27/236 Hydroxy carbonates
• CPC Class Codes: C07C 51/36 by hydrogenation of carbon-to-carbon unsaturated bonds
• CPC Class Codes: C07C 57/03 Monocarboxylic acids
• CPC Class Codes: C07C 57/12 Straight chain carboxylic acids containing eighteen carbon atoms
• CPC Class Codes: C10M 101/04 Fatty oil fractions
• CPC Class Codes: C10M 105/38 of polyhydroxy compounds
• CPC Class Codes: C10M 105/40 containing free hydroxy or carboxyl groups
• CPC Class Codes: C10M 2207/2835 used as base material
• CPC Class Codes: C10M 2207/2895 used as base material
• CPC Class Codes: C10M 2207/401 used as base material
• CPC Class Codes: C10N 2020/013 Iodine value
• CPC Class Codes: C10N 2020/067 Unsaturated Compounds
• CPC Class Codes: C10N 2030/02 Pour-point; Viscosity index
• CPC Class Codes: C10N 2030/06 Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
• CPC Class Codes: C10N 2030/10 Inhibition of oxidation, e.g. anti-oxidants
• CPC Class Codes: C10N 2030/74 Noack Volatility
• CPC Class Codes: C10N 2040/00 Specified use or application for which the lubricating composition is intended
• CPC Class Codes: C10N 2040/16 Dielectric; Insulating oil or insulators
• CPC Class Codes: C10N 2040/20 Metal working
• CPC Class Codes: C11C 3/126 : using catalysts based principally on other metals or derivates

Abstract

A hydrogenation process for producing high monoene compositions is disclosed. In particular, a catalyst comprising basic copper carbonate is used for the selective hydrogenation of oils that contain unsaturated fatty acyl components such as unsaturated vegetable oils. Hydrogenation according to the methods of the invention yield high monoene compositions that are useful for industrial applications, such as lubricants.

Claims

1. A hydrogenation process comprising:

contacting a first composition containing at least two sites of unsaturation with a hydrogenation catalyst comprising basic copper carbonate in a hydrogen atmosphere under conditions effective to form a hydrogenated composition;

said hydrogenated composition having a ratio of monounsaturated content to saturated content of greater than about 2, and a saturated content not substantially higher than the saturated content of the first composition.

2. The process of claim 1, wherein hydrogenation occurs at a temperature of about 50°

C. to about 250°

C.

3. The process of claim 1, wherein hydrogenation occurs at a pressure of about 40 psi to about 80 psi.

4. The process of claim 1, wherein hydrogenation occurs for a time period of about 4 hours to about 8 hours.

5. The process of claim 1, wherein the catalyst comprises hydrogen peroxide-treated basic copper carbonate.

6. The process of claim 1, wherein the catalyst comprises a natural malachite mineral.

7. The process of claim 1, wherein the catalyst comprises precipitated basic copper carbonate.

8. The process of claim 1, wherein the catalyst is unsupported.

9. The process of claim 1, wherein said first composition comprises a fatty acyl-containing composition, wherein said fatty acyl contains at least two sites of unsaturation in a carbon chain.

10. The process of claim 9, wherein said fatty acyl-containing composition comprises a polyunsaturated vegetable, animal or synthetic fat or oil, or derivatives or mixtures thereof.

11. The process of claim 10, wherein said oil is a vegetable oil.

12. The process of claim 11, wherein said 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 and conjugated derivatives of said oils, and mixtures thereof.

13. The process of claim 1, wherein said hydrogenated composition is a vegetable oil comprised of fatty acid chains having a profile selected from the group consisting of:

(a) C18;

1/C18;

0 above about 6.0;

C18;

2/C18;

0 above about 6.0; and

C 18;

0 no greater than about 5%;

(b) C18;

1/C18;

0 above about 10.0;

C18;

2/C18;

0 above about 3.2; and

having C18;

0 no greater than about 5%;

(c) C18;

1/C18;

0 above about 13.9;

C18;

2/C18;

0 above about 3.9; and

having C18;

0 no greater than about 5%; and

(d) C18;

1/C18;

0 above about 10.7;

C18;

2/C18;

0 above about 7.2; and

having C18;

0 no greater than about 5%.

14. The process of claim 1, wherein said catalyst does not contain copper chromite.

15. A hydrogenated composition prepared by the process of claim 1.

16. A lubricant comprising a hydrogenated fatty acyl-containing composition having a ratio of monounsaturated content to saturated content of greater than about 2.

17. The lubricant of claim 16, wherein the fatty acyl containing-composition is a hydrogenated vegetable oil.

18. The lubricant of claim 17, wherein the hydrogenated vegetable oil is comprised of fatty acid chains having a profile selected from the group consisting of:

(a) C18;

1/C18;

0 above about 6.0;

C18;

2/C18;

0 above about 6.0; and

C18;

0 no greater than about 5%;

(b) C18;

1/C18;

0 above about 10.0;

C18;

2/C18;

0 above about 3.2; and

having C18;

0 no greater than about 5%;

(c) C18;

1/C18;

0 above about 13.9;

C18;

2/C18;

0 above about 3.9; and

having C18;

0 no greater than about 5%; and

(d) C18;

1/C18;

0 above about 10.7;

C18;

2/C18;

0 above about 7.2; and

having C18;

0 no greater than about 5%.

19. A method of producing a lubricant, comprising:

contacting a first composition containing at least two sites of unsaturation with a hydrogenation catalyst comprising basic copper carbonate in a hydrogen atmosphere under conditions effective to form a hydrogenated composition,

said hydrogenated composition having a ratio of monounsaturated content to saturated content of greater than about 2.

20. The method of claim 19, wherein said first composition is a polyunsaturated vegetable oil and wherein the hydrogenated composition has a saturated content that is not substantially higher than the saturated content of said first composition.

21. (canceled)