Process for the preparation of cyclohexyl-substituted tertiary alkanols

Patent metadata

Field	Value
Publication number	US-9340754-B2
Application number	US-201314090626-A
Country	US
Kind code	B2
Filing date	Nov 26, 2013
Priority date	Nov 27, 2012
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

The present invention relates to processes for the preparation of compounds of the formula (Ia)

by reacting styrene with a secondary alkanol and the hydrogenation of the resulting phenyl-substituted tertiary alkanol. In addition, the invention relates to compounds of the formula (Ia) and to the use of such compounds as fragrances, and also to compositions which comprise compounds of the formulae (Ia) and (Ib).

First claim

The invention claimed is:

1. A process for the preparation of a composition comprising a compound of formula (Ia) and a compound of formula (Ib)

the process comprising:
a) reacting styrene with a compound of the formula (II)

 to provide a compound of formula (IIIa) and a compound of formula (IIIb)

 and
b) the heterogeneous-catalytic hydrogenation of the compounds of the formula (IIIa) and formula (IIIb) to give the compounds of the formula (Ia) and the formula (Ib),
where R 1 and R 2 , independently of one another, are selected from C 3-7 -cycloalkyl-C 1-7 -alkyl-, C 3-7 -cycloalkyl-, or C 1-7 -alkyl-, and R 1 and R 2 together comprise in total 3 to 11 carbon atoms.

2. The process according to claim 1 , wherein R 1 and R 2 , independently of one another, are selected from C 1-7 -alkyl-, C 3-7 -cycloalkyl or C 4-7 -cycloalkylalkyl.

3. The process according to claim 1 , wherein the reaction in step a) takes place under conditions under which the compound of the formula (II) is present in a supercritical state.

4. The process according to claim 1 , wherein the reaction in step a) takes place at a temperature in the range from 250 to 500° C. and a pressure in the range from 5 to 50 MPa.

5. The process according to claim 1 , wherein the molar ratio of the styrene used in step a) to the compound of the formula (II) used in step a) is in the range from 1:5 to 1:200.

6. The process according to claim 1 , wherein the catalyst used in step b) comprises at least one active metal selected from the group consisting of palladium, platinum, cobalt, nickel, rhodium, iridium and ruthenium.

7. The process according to claim 6 , wherein the catalyst used in step b) comprises ruthenium as active metal.

8. The process according to claim 6 , wherein the catalyst used in step b) comprises at least one further active metal of sub-groups IB, VIIB or VIIIB of the Periodic Table (CAS version).

9. The process according to claim 1 , wherein step b) is carried out in trickle mode.

10. The process according to claim 1 , wherein R 1 is methyl and R 2 is ethyl.

11. A composition comprising a compound of the formula (Ia)

and a compound of the formula (Ib)

where R 1 and R 2 , independently of one another, are selected from C 3-7 -cycloalkyl-C 1-7 -alkyl-, C 3-7 -cycloalkyl-, and C 1-7 -alkyl-,and R 1 and R 2 together comprise in total 3 to 11 carbon atoms.

12. The composition according to claim 11 , wherein R 1 and R 2 , independently of one another, are selected from the group consisting of C 1-7 -alkyl-, C 3-7 -cycloalkyl and C 4-7 -cycloalkylalkyl.

13. The composition according to claim 11 , where R 1 is methyl and R 2 is ethyl.

14. A cosmetic composition comprising a compound of the formula (Ia) and a compound of formula (Ib)

where R 1 and R 2 , independently of one another, are selected from C 3-7 -cycloalkyl-C 1-7 -alkyl-, C 3-7 -cycloalkyl-, and C 1-7 -alkyl-,and R 1 and R 2 together comprise in total 3 to 11 carbon atoms, wherein the cosmetic composition is formulated as aqueous or alcoholic liquid, oil, spray, foam, mousse, gel, gel spray, cream, lotion, tabs or wax.

15. The cosmetic composition, textile detergent or cleaner for hard surfaces according to claim 14 , wherein R 1 is methyl and R 2 is ethyl.

Assignees

• Basf Se

Inventors

• Rüdenauer Stefan
• Pelzer Ralf
• Ebel Klaus
• Bock Martin

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• A61K2800/10

  General cosmetic use · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• A61K8/34 Primary

  Alcohols · CPC title

• C11D3/2065 Primary

  Polyhydric alcohols · CPC title