Production of farnesol

Patent metadata

Field	Value
Publication number	US-10450250-B2
Application number	US-201615757685-A
Country	US
Kind code	B2
Filing date	Sep 16, 2016
Priority date	Sep 17, 2015
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

The present invention relates to an improved way for the production of farnesol.

First claim

The invention claimed is:

1. A process for the production of the compound of formula (I):

wherein the process comprises the steps of:
(1) reacting a compound of formula (II):

by a rearrangement process in the presence of:
(i) at least one mononuclear vanadium catalyst having the following formula:

 wherein R is an alkyl or aryl group or a M(R 1 ) 3 group, where M is Si, Sn or Ge and R 1 is an alkyl or aryl group, and wherein the catalyst is present in a weight ratio of the compound of formula (II) to the catalyst in a range of 10:1 to 500:1, and
(ii) 0.001 to 0.015 mol equivalent relative to the compound of formula (II) at least one least one saturated fatty acid with a 16-22 carbon chain selected from the group consisting of stearic acid, palmitic acid, arachidic acid and behenic acid to thereby form a compound of formula (III):

and thereafter

(2) conducting hydrogenation of the compound of formula (III) to the compound of formula (I).

2. The process according to claim 1 , wherein the mononuclear vandium catalyst is at least one catalyst compound selected from the group consisting of:

3. The process according to claim 1 , wherein the reaction of step (1) is carried out in at least one non-polar aprotic solvent.

4. The process according to claim 3 , wherein the at least one non-polar aprotic solvent is selected from aliphatic solvents having a boiling point above 280° C., and aromatic solvents.

5. The process according to claim 1 , wherein the reaction of step (1) is carried out at a temperature between 30° C. and 180° C.

6. The process according to claim 1 wherein the hydrogenation of step (2) is carried out with H 2 gas.

7. The process according to claim 1 , wherein the hydrogenation of step (2) is a transfer hydrogenation.

8. The process according to claim 7 , wherein the transfer hydrogenation is carried out in the presence of at least one metal-complex, wherein the metal is selected from the group consisting of Ir, Rh and Ru.

9. The process according to claim 8 , wherein the metal-complex is selected from the group consisting of pentamethylcyclopentadienyl Ir-complex (Cp*Ir), pentamethylcyclopentadienyl Rh-complex (Cp*Rh) and Ru-arene-complexes.

10. The process according to claim 8 , wherein the metal-complex also comprises at least one organic ligand which comprises at least one N and/or P atom.

11. The process according to claim 10 , wherein the at least one organic ligand comprises 1,2 amino alcohols and/or mono-sulfonated 1,2-diamines.

12. The process according to claim 7 , wherein the transfer hydrogenation is carried out in the presence of at least one alcohol or a salt thereof, formic acid or a salt thereof or a formic acid/trimethylamine complex.

13. The process according to claim 4 , wherein the solvent is xylene or toluene.

14. The process according to claim 9 , wherein the metal-complex is a Ru-p-cymene complex or a Ru-benzene complex.

Assignees

• Dsm Ip Assets Bv

Inventors

• Bonrath Werner
• Beumer Raphael
• Medlock Jonathan Alan

Classifications

• C07C45/512

  the singly bound functional group being a free hydroxyl group · CPC title

• C07C29/141 Primary

  with hydrogen or hydrogen-containing gases · CPC title

• C07C29/14

  of a —CHO group · CPC title

• B01J31/2295

  Cyclic compounds, e.g. cyclopentadienyls · CPC title

• B01J31/0275

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0269 · CPC title