Transesterification process

• US 5,847,239 A
• Filed: 01/15/1997
• Issued: 12/08/1998
• Est. Priority Date: 01/15/1996
• Status: Expired due to Fees

• Current Assignee: Quest International B.V.. (Givaudan SA)
• Original Assignee: Quest International B.V.. (Givaudan SA)
• Inventors: Newman, Christopher Paul, Hart, Barrie R., Richardson, Clive Derek, Davey, Paul Nicolas
• Primary Examiner(s): Killos, Paul J.
• Application Number:
  US08/785,832
• Time in Patent Office: 692 Days
• Field of Search: 568/876, 568/877
• US Class Current: 568/877
• CPC Class Codes: C07C 29/128 by alcoholysis
• CPC Class Codes: C07C 33/025 with only one double bond
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 67/04 by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
• CPC Class Codes: C07C 69/007 Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
• CPC Class Codes: C07C 69/14 of monohydroxylic compounds
• CPC Class Codes: C07C 69/145 of unsaturated alcohols
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials

Abstract

Dihydromyrcene is reacted with a carboxylic acid, eg acetic acid, to produce an ester which is then reacted with an alcohol in a transesterification reaction to produce (dihydro)myrcenol and another ester. The preferred alcohol is 4-tertiarybutylcyclohexanol. Myrcenol can be produced in a similar way.

Claims

1. A process for preparing (dihydro)myrcenol comprising reacting a (dihydro)myrcenol ester of acetic, propionic, butyric or isobutyric acid, with an alcohol in a transesterification reaction to produce (dihydro)myrcenol.

2. A process according up to claim 1, wherein the (dihydro)myrcenyl ester is the acetate.

3. A process according to claim 1, wherein the transesterification reaction is carried out in the presence of a catalyst, preferably an alkoxide catalyst.

4. A process according to claim 1 wherein (dihydro)myrcenol or the product ester are removed from the reaction mixture by distillation.

5. A process according to claim 1, wherein the alcohol is chosen such that the boiling points of the (dihydro)myrcenol and the ester produced in the transesterification reaction are at least 2°

C. apart from each other, and from those of the starting (dihydro)myrcenyl ester and the starting alcohol at the distillation pressure.

6. A process according to claim 1 wherein the transesterification reaction is carried out below 300°

C.

7. A process according to claim 1, wherein the alcohol is 4-tertiarybutylcyclohexanol or 2-tertiary-butylcyclohexanol.

8. A process according to claim 1 wherein the (dihydro)myrcenyl ester is produced by reacting (dihydro)myrcene with acetic acid.

9. A process according to claim 8, wherein the ester-producing reaction is effected in the presence of a solid catalyst.

10. A process according to claim 9, wherein the solid catalyst is an ion-exchange catalyst.

11. A process according to claim 8, wherein the ester-producing reaction is carried out as a continuous process at a temperature consistent with a liquid phase reaction.

12. A process according to claim 8, wherein dihydromyrcene is reacted with acetic acid to produce dihydromyrcenyl acetate, which is then reacted with 4-tertiarybutylcyclohexanol to produce dihydromyrcenol and 4-tertiarybutylcyclohexyl acetate.

13. A process according to claim 1 wherein the transesterification reaction is carried out at a temperature below 250°

C.

14. A process according to claim 11 wherein the ester-producing reaction is carried out at a temperature in the range of 15°

-20 °

C.