Enzyme-catalyzed reactions involving diphenyl carbonate

• US 4,892,822 A
• Filed: 10/22/1987
• Issued: 01/09/1990
• Est. Priority Date: 10/22/1987
• Status: Expired due to Fees

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Keese, Charles R., Abramowicz, Daniel A.
• Primary Examiner(s): Griffin, Ronald W.
• Assistant Examiner(s): Webber, Pamela S.
• Application Number:
  US07/111,248
• Time in Patent Office: 810 Days
• Field of Search: 435/132, 528/196
• US Class Current: 435/132
• CPC Class Codes: C08G 64/307 and phenols
• CPC Class Codes: C12P 7/22 aromatic
• CPC Class Codes: C12P 7/62 Carboxylic acid esters

Abstract

Enzyme-catalyzed exchange reactions with diphenyl carbonate compounds are disclosed. Nucleophiles participating in these reactions include water and a wide range of hydroxy-containing compounds. Polycarbonate products can be prepared according to this invention by the use of various bisphenols in a transesterification reaction with the diphenyl carbonate compound.

Claims

1. A method for performing an exchange reaction with a diphenyl carbonate compound of the formula ##STR7## wherein each A is individually selected from the group consisting of hydrogen, lower alkyl groups, lower alkoxy groups, and halogens, comprising the reaction of the diphenyl carbonate compound with water or an alcohol in the presence of an enzymatic catalyst having an active site capable of binding the diphenyl carbonate while retaining a catalytic residue after binding.

2. The method of claim 1 wherein the exchange reaction is transesterification, and the enzymatic catalyst is selected from the group consisting of Candida Cylindracea lipase, Porcine liver esterase, Pseudomonas Fluorescens cholesterol esterase, and Rhizopus lipase.

3. The method of claim 1 wherein the exchange reaction is transesterification and the enzymatic catalyst is Candida Cylindracea lipase.

4. The method of claim 2 wherein the alcohol has the formula ROH, R being a lower alkyl group or a lower aromatic group.

5. The method of claim 4 wherein the alcohol is in the form of a racemic mixture, and wherein at least one of the products of the transesterification reaction is optically active.

6. The method of claim 5 wherein the alcohol is 2-butanol.

7. The method of claim 2 wherein the alcohol is dihydric or polyhydric.

8. The method of claim 7 wherein the alcohol is a spirobiindane bisphenol.

9. The method of claim 7 wherein the alcohol is a di-(monohydroxylaryl)-alkane.

10. The method of claim 9 wherein the di-(monohydroxylaryl)-alkane is bisphenol A.

11. The method of claim 7 wherein the reaction is performed in a water-restricted environment which maximizes transesterification products and minimizes hydrolysis by-products.

12. The method of claim 11 wherein the water-restricted environment comprises a hydrophobic solvent and between about 0.1% and 0.4% by weight water.

13. The method of claim 12 wherein the solvent is methylene chloride.

14. The method of claim 12 wherein the enzymatic catalyst is first adsorbed onto an inert surface which is then inserted into the reaction medium containing the diphenyl carbonate compound and the water or alcohol.

15. The method of claim 14 wherein the inert surface is that of fumed silica.

16. The method of claim 1 wherein the exchange reaction is hydrolysis.

17. A method for the preparation of polycarbonates, comprising the transesterification of a diphenyl carbonate compound with a dihydric phenol in the presence of an enzymatic catalyst selected from the group consisting of Candida Cylindracea lipase, Porcine liver esterase, Rhizopus lipase, and Pseudomonas Fluorescens cholesterol esterase.

18. The method of claim 17 wherein the dihydric phenol is bisphenol A.

19. The method of claim 18 wherein transesterification occurs in a water-restricted environment.