Method for producing arylpropenes

Patent metadata

Field	Value
Publication number	US-9765001-B2
Application number	US-201515111841-A
Country	US
Kind code	B2
Filing date	Jan 16, 2015
Priority date	Jan 17, 2014
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

The present invention relates to a process for preparing arylpropenes, especially 1-methoxy-4-(1-propenyl)benzene (anethole), by means of thermolysis of the corresponding 1,1-diarylpropanes.

First claim

The invention claimed is:

1. A process for preparing arylpropenes of the formula (I)

in which
k has the values of 0, 1, 2 or 3 and
R 1 is independently selected from the group consisting of C 1 -C 6 -alkoxy, di(C 1 -C 6 -alkyl)amines and hydroxyl,
comprising thermolyzing at least one 1,1-diarylpropane compound of the formula (II)

in which k and R 1 have the definitions given above,
wherein the compound of the formula II in the gas phase is contacted with at least one solid acidic oxidic catalyst in a reaction zone.

2. The process according to claim 1 , wherein, in the formulae I and II, k=1 and R 1 is hydroxyl or C 1 -C 6 -alkoxy.

3. The process according to claim 1 , wherein the 1,1-diarylpropane compounds (II) comprise, to an extent of at least 50 mol %, based on the total amount of the compounds of the formula II, compounds of the formula (II.a)

in which both R 1 are the same.

4. The process according to claim 1 , wherein the reaction zone is supplied, together with the compound of the formula II, additionally with at least one solvent S.

5. The process according to claim 4 , wherein the solvent S is water.

6. The process according to claim 4 , wherein the mass ratio of solvent S to the compound of the formula II is in the range from 20:1 to 1:100.

7. The process according to claim 1 , wherein the catalyst comprises silicon dioxide.

8. The process according to claim 7 , wherein the catalyst is a silica which has optionally been impregnated with one or more inorganic acids.

9. The process according to claim 1 , wherein the compound of the formula II is contacted with the catalyst at a temperature in the range from 250 to 650° C.

10. The process according to claim 1 , wherein the compound of the formula II is conducted continuously through the reaction zone comprising the solid oxidic catalyst.

11. The process according to claim 10 , wherein the compound of the formula II is supplied continuously to the reaction zone and the reaction product is quenched immediately after leaving the reaction zone.

12. The process according to claim 10 , wherein the compound of the formula II is supplied to the reaction zone with the aid of a carrier gas.

13. The process according to claim 10 , wherein the compound of the formula II is conducted through the reaction zone with a catalyst load of 0.01 to 5 kg of compound II per kg of catalyst and hour.

14. The process according to claim 1 , wherein, in the formulae I and II, k=1 and R 1 is hydroxyl or methoxy.

Assignees

• BASF SE (Herzog Fiesser & Partner)
• Basf Se

Inventors

• Rüdenauer Stefan
• Lanver Andreas
• Pelzer Ralf
• Ebel Klaus
• Fenlon Thomas

Classifications

• C07C43/215

  having unsaturation outside the six-membered aromatic rings · CPC title

• C07C41/18 Primary

  by reactions not forming ether-oxygen bonds · CPC title

• C07C67/00

  Preparation of carboxylic acid esters · CPC title

• C07C43/20

  having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring · CPC title