Method for preparing dinitrile compound

Patent metadata

Field	Value
Publication number	US-9394242-B2
Application number	US-201314026233-A
Country	US
Kind code	B2
Filing date	Sep 13, 2013
Priority date	Mar 18, 2011
Publication date	Jul 19, 2016
Grant date	Jul 19, 2016

Abstract

Disclosed is a method for preparing a dinitrile compound. The method includes reacting an alcohol compound with a nitrile compound having a terminal carbon-carbon unsaturated bond under anhydrous conditions. A potassium alkoxide having 1 to 5 carbon atoms is used as a catalyst in the course of the reaction. According to the method, a high-purity dinitrile compound can be prepared in a simple manner within a short reaction time indicating high productivity.

First claim

What is claimed is:

1. A method for preparing a dinitrile compound, the method comprising:
reacting an alcohol compound of the formula H—(O—R 2 ) m —OH, wherein R 2 is C 1 -C 5 alkylene or alkenylene and m is 1-5, with a nitrile compound having a terminal carbon-carbon unsaturated bond, where the nitrile group is bonded to the carbon-carbon unsaturated bond directly or through at least one alkylene,
wherein the alcohol compound reacts with and adds to the terminal carbon of the carbon-carbon unsaturated bond of the nitrile compound, under anhydrous conditions,
wherein a potassium alkoxide having 4 to 5 carbon atoms is used as a catalyst for the reaction, and
wherein the reaction is carried by stirring the alcohol compound and the potassium alkoxide, adding the nitrile compound to prepare a reaction mixture, stirring the reaction mixture, wherein the reaction is carried out at 40° C.,
wherein the dinitrile compound is represented by Formula 1:
NC—R 1 O—R 2 m —O—R 3 —CN  (1)

wherein R 1 , R 2 and R 3 are each independently C 1 -C 5 alkylene or alkenylene and m is an integer from 1 to 5.

2. The method according to claim 1 , wherein the potassium alkoxide is selected from the group consisting of potassium tert-butoxide, potassium tert-pentoxide, and mixtures thereof.

3. The method according to claim 1 , wherein the potassium alkoxide is used in an amount of 0.01 to 5 parts by weight, based on 100 parts by weight of the alcohol compound.

4. The method according to claim 1 , wherein the alcohol compound is selected from the group consisting of ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, and mixtures thereof.

5. The method according to claim 1 , wherein the nitrile compound having a terminal carbon-carbon unsaturated bond is selected from the group consisting of acrylonitrile, 3-butenenitrile, 4-pentenenitrile, and mixtures thereof.

6. The method according to claim 1 , wherein the dinitrile compound is selected from the group consisting of 3,5-dioxa-heptanedinitrile, 1,4-bis(cyanoethoxy)butane, bis(2-cyanoethyl)-monoformal, bis(2-cyanoethyl)-diformal, bis(2-cyanoethyl)-triformal, ethylene glycol bis(2-cyanoethyl)ether, bis(2-(2-cyanoethoxy)ethyl)ether, 4,7,10,13-tetraoxahexadecanedinitrile, 4,7,10,13,16-pentaoxanonadecane-1,14-dinitrile, 3,6,9,12,15,18-hexaoxaeicosan dinitrile, 4,10-dioxa-undecanedinitrile, 1,10-dicyano-3,8-dioxadecane, 4,10-dioxa-tridecanedinitrile, 6,9-dioxa-tetradecanedinitrile, and mixtures thereof.

7. The method according to claim 1 , wherein the nitrile compound having a terminal carbon-carbon unsaturated bond is acrylonitrile.

Assignees

• Lg Chemical Ltd

Inventors

• Lee Byoung-Bae
• Oh Jae-Seung
• Shim You-Jin
• Hong Yeon-Suk

Classifications

• B01J2231/32

  Addition reactions to C=C or C-C triple bonds · CPC title

• C07C255/13

  containing cyano groups and etherified hydroxy groups bound to the carbon skeleton · CPC title

• B01J31/0212

  Alkoxylates · CPC title

• C07C253/30 Primary

  by reactions not involving the formation of cyano groups · CPC title

• B01J23/04

  Alkali metals · CPC title