Process for the preparation of 3,7-dimethylnonan-1-ol

Patent metadata

Field	Value
Publication number	US-9718749-B2
Application number	US-201414774976-A
Country	US
Kind code	B2
Filing date	Mar 11, 2014
Priority date	Mar 13, 2013
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

The present invention is related to a novel and improved process for the preparation of 3,7-dimethylnonan-1-ol.

First claim

The invention claimed is:

1. A two-step process for the production of a compound of formula (I):

wherein
the process consists of:
(i) subjecting in a first step a compound of formula (II):

to a rearrangement reaction to obtain a compound of formula (III);

and thereafter
(ii) subjecting in a second step the compound of formula (III) to hydrogenation in the presence of a nickel/chromium catalyst with Fe/Cr promoter to obtain the compound of formula (I) with a conversion of greater than 99%.

2. The two-step process according to claim 1 , which comprises using in step (i) a catalyst of formula (IV):

wherein
R 1 , R 2 and R 3 are independently from each other a linear or branched C 1 -C 10 -alkyl moiety or Si(R 4 ) 3 , and wherein
each R 4 is independently from each other a linear or branched C 1 -C 10 -alkyl moiety or substituted or unsubstituted phenyl.

3. The two-step process according to claim 1 , which comprises using in step (i) a catalyst of formula (IV′):

4. The two-step process according to claim 1 , wherein the reaction of step (i) is carried out in at least one hydrocarbon solvent.

5. The two-step process according to claim 1 , wherein the reaction of step (i) is carried out at a temperature of 50° C. to 200° C.

6. The two-step process according to claim 1 , wherein the reaction of step (i) is carried out at normal pressure.

7. The two-step process according to claim 1 , wherein step (ii) is carried out using pure H 2 -gas or a gas mixture which comprises H 2 .

8. The two-step process according to claim 1 , wherein the hydrogenation of step (ii) is carried out at a pressure of 1.5-40 bar.

9. The two-step process according to claim 1 , wherein the catalyst of step (ii) is a sponge nickel/chromium catalyst with Fe/Cr promoter.

10. The two-step process according to claim 1 , wherein step (ii) is carried out in the absence of solvents.

11. The two-step process according to claim 1 , wherein step (ii) is carried out in a solvent or a solvent mixture.

12. The two-step process according to claim 11 , wherein the solvent is at least one selected from the group consisting of linear, branched or cyclic aliphatic hydrocarbons having 5-10 carbon atoms; aromatic hydrocarbons having 5-10 carbon atoms; esters; ethers; and alcohols.

13. The two-step process according to claim 12 , wherein the solvent is at least one selected from the group consisting tetrahydrofuran (THF), n-hexane, n-heptane, 2-propanol, toluene and ethyl acetate.

14. The two-step process according to claim 8 , wherein the hydrogenation of step (ii) is carried out at a pressure of 2-30 bar.

Assignees

• Dsm Ip Assets Bv
• Dsm Ip Assets Bv

Inventors

• Bonrath Werner
• Medlock Jonathan

Classifications

• C07C29/14

  of a —CHO group · CPC title

• C07C45/51

  by pyrolysis, rearrangement or decomposition · CPC title

• C07C31/125

  containing five to twenty-two carbon atoms · CPC title

• C07C29/172 Primary

  with the obtention of a fully saturated alcohol · CPC title

• C07C45/511

  involving transformation of singly bound oxygen functional groups to >C = O groups (involving two hydroxy groups C07C45/52; hydroperoxides C07C45/53) · CPC title