Process for preparing 1,4-bis(ethoxymethyl)cyclohexane

Patent metadata

Field	Value
Publication number	US-10106477-B2
Application number	US-201615753236-A
Country	US
Kind code	B2
Filing date	Aug 17, 2016
Priority date	Aug 18, 2015
Publication date	Oct 23, 2018
Grant date	Oct 23, 2018

Abstract

The present invention relates to a process for preparing, 4-bis(ethoxymethyl)cyclohexane, which comprises reacting 1,4-bis(hydroxymethyl)cyclohexane with ethyl chloride in the presence of an inorganic base, a solvent and a phase transfer catalyst to yield a reaction mixture containing 1,4-bis(ethoxymethyl)cyclohexane, where the inorganic base is selected from alkali metal hydroxides and earth alkaline metal hydroxides and where the solvent is selected from water or a mixture of water with at least one organic solvent.

First claim

We claim:

1. A process for preparing 1,4-bis(ethoxymethyl)cyclohexane, which comprises reacting 1,4-bis(hydroxymethyl)cyclohexane with ethyl chloride in the presence of an inorganic base, a solvent and a phase transfer catalyst to yield a reaction mixture containing 1,4-bis(ethoxymethyl)cyclohexane,
wherein the inorganic base is selected from the group consisting of alkali metal hydroxides and earth alkaline metal hydroxides, and wherein the solvent is selected from water or a mixture of water with at least one organic solvent.

2. The process of claim 1 , wherein the inorganic base is selected from the group consisting of potassium hydroxide and sodium hydroxide.

3. The process according to claim 1 , wherein the inorganic base is used in the form of an aqueous solution.

4. The process of claim 1 , wherein the molar ratio of OH − in the inorganic base to 1,4-bis(hydroxymethyl)cyclohexane is in the range of 2:1 to 20:1.

5. The process of claim 1 , wherein the molar ratio of ethyl chloride to 1,4-bis(hydroxymethyl)cyclohexane is in the range of 2:1 to 15:1.

6. The process of claim 1 , wherein said at least one organic solvent is selected from the group consisting of aliphatic hydrocarbons, aromatic hydrocarbons, aliphatic ethers, alicyclic ethers and mixtures thereof.

7. The process of claim 1 , wherein the solvent comprises at least 90% by weight, of water based on the total amount of solvent.

8. The process of claim 1 , wherein the phase transfer catalyst is selected from quaternary ammonium salts.

9. The process of claim 1 , wherein the phase transfer catalyst is selected from tetra-(C 1 -C 10 -alkyl)ammonium salts.

10. The process of claim 1 , wherein the amount of the phase transfer catalyst used is in the range of 1 to 20 mol-%, based on the amount of 1,4-bis(hydroxymethyl)cyclohexane.

11. The process of claim 1 , wherein the ethyl chloride is added to a mixture of 1,4-bis(hydroxymethyl)cyclohexane, the inorganic base, the solvent and the phase transfer catalyst.

12. The process of claim 1 , wherein the reaction is performed at a temperature in the range of 30 to 110° C.

13. The process of claim 1 , further comprising purifying the reaction mixture containing 1,4-bis(ethoxymethyl)cyclohexane.

14. The process of claim 1 , wherein the phase transfer catalyst is tetra-n butylammonium salts.

Assignees

• Basf Se

Inventors

• Fenlon Thomas
• Rüdenauer Stefan
• Pelzer Ralf
• Hindalekar Shrirang
• Swaminathan Vijay Narayanan
• Gupte Nitin
• Ardekar Sadanand

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• C07C2531/02

  containing organic compounds or metal hydrides · CPC title

• C07C41/01 Primary

  Preparation of ethers · CPC title

• C07C43/115

  containing carbocyclic rings · CPC title

• C07C41/16 Primary

  by reaction of esters of mineral or organic acids with hydroxy or O-metal groups · CPC title