Catalyst compositions and the use thereof in the hydrogenation of carboxylic acid esters

• US 4,929,777 A
• Filed: 02/13/1989
• Issued: 05/29/1990
• Est. Priority Date: 02/13/1989
• Status: Expired due to Term

• Current Assignee: Eastman Chemical Company
• Original Assignee: Eastman Kodak Company
• Inventors: Irick, Gether Jr., Mercer, Patricia N., Simmons, Kenneth E.
• Primary Examiner(s): LONE, WERREN
• Application Number:
  US07/309,641
• Time in Patent Office: 470 Days
• Field of Search: 568/861, 568/864, 568/862, 568/833
• US Class Current: 568/864
• CPC Class Codes: B01J 23/72 Copper
• CPC Class Codes: B01J 23/76 combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 29/149 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 31/04 Methanol
• CPC Class Codes: C07C 31/08 Ethanol
• CPC Class Codes: C07C 31/207 1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol
• CPC Class Codes: C07C 31/276 with a six-membered ring
• CPC Class Codes: Y02P 20/52 using catalysts, e.g. selective catalysts

Abstract

Disclosed are catalyst compositions comprised of chemically-mixed, copper-titanium oxides and the use of such catalyst compositions in the hydrogenation of certain esters to obtain the alcohol corresponding to the acid residue of the ester.

Claims

1. A process for hydrogenating an ester of an aliphatic or cycloaliphatic carboxylic acid to obtain the alcohol corresponding to the acid residue of the ester which comprises contacting the ester with hydrogen in the presence of catalyst comprising as the essential ingredient chemically-mixed, copper-titanium oxide under hydrogenation conditions of temperature and pressure.

2. Process according to claim 1 wherein the hydrogen pressure is less than 3000 psi and the temperature is about 150 to 300°

C.

3. A process according to claim 2 for hydrogenating an ester of an aliphatic or cycloaliphatic carboxylic acid to obtain the alcohol corresponding to the acid residue of the ester which comprises contacting the ester with hydrogen in the presence of a catalyst composition comprising as the essential ingredient chemically-mixed, copper-titanium oxide wherein the copper oxide content, calculated as CuO, of the catalyst composition is from about 3 to 65 weight percent wherein the hydrogen pressure is less than 3000 psi and the temperature is about 200°

to 300°

C.

4. A process according to claim 3 wherein the catalyst composition also contains an oxide of lanthanum or zinc.

5. A process according to claim 3 wherein the copper oxide content, calculated as CuO, of the catalyst composition is from about 8.8 to 44.0 weight percent.

6. A process according to claim 5 wherein the catalyst composition also contains an oxide of lanthanum or zinc.

7. Process according to claim 5 wherein the ester is dimethyl 1,4-cyclohexanedicarboxylate.

8. Process according to claim 5 wherein the ester is a lower alkyl ester of a C₁₀ -C₂₀ carboxylic acid.

9. Process according to claim 5 wherein the ester is a di-lower alkyl adipate.

10. Process according to claim 5 wherein the ester is a di-lower alkyl maleate.

11. A process for hydrogenating an ester of an aliphatic or cycloaliphatic carboxylic acid to obtain the alcohol corresponding to the acid residue of the ester which comprises contacting the ester hydrogen in the presence of a catalyst composition comprising as the essential ingredient chemically-mixed, copper-titanium oxide of the formula

View Dependent Claims (12, 13, 14, 15, 16, 17)

12. A process according to claim 11 wherein x is about 0.09 to 0.44, y is about 0.91 to 0.56 and z is about 1.91 to 1.56.

13. A process according to claim 12 wherein the catalyst composition also contains an oxide of lanthanum or zinc.

14. A process according to claim 12 wherein the catalyst composition is combined with or deposited on an oxide of silicon, aluminum, germanium, boron, tin or zinc.

15. Process according to claim 14 wherein the ester is a lower alkyl ester of 1,4-cyclohexanedicarboxylic acid.

16. Process according to claim 14 wherein the ester is a lower alkyl ester of a C₁₀ -C₂₀ carboxylic acid.

17. Process according to claim 14 wherein the ester is a di-lower alkyl maleate.