Process for producing cyanonorbornene

Patent metadata

Field	Value
Publication number	US-2020239408-A1
Application number	US-201816634929-A
Country	US
Kind code	A1
Filing date	Jul 23, 2018
Priority date	Jul 31, 2017
Publication date	Jul 30, 2020
Grant date	—

Abstract

A process for producing cyanonorbornene of the present invention includes Step 1 of preparing a mixture solution including 0.5% by weight to 28% by weight of methyl bicyclononadiene, with respect to a total amount of 100% by weight of dicyclopentadiene, acrylonitrile, and the methyl bicyclononadiene, in a container, and Step 2 of reacting the bicyclopentadiene with the acrylonitrile in the presence of the methyl bicyclononadiene, in the mixture solution.

First claim

1 . A process for producing cyanonorbornene, comprising:
Step 1 of preparing a mixture solution including 0.5% by weight to 28% by weight of methyl bicyclononadiene, with respect to a total amount of 100% by weight of dicyclopentadiene, acrylonitrile, and the methyl bicyclononadiene, in a container; and Step 2 of reacting the dicyclopentadiene with the acrylonitrile in the presence of the methyl bicyclononadiene, in the mixture solution.

2 . The process for producing cyanonorbornene according to claim 1 , further comprising:
after Step 2, Step 3 of obtaining cyanonorbornene and recovering the methyl bicyclononadiene and a non-reactive raw material, from a reaction product obtained in Step 2; and Step 4 of providing the recovered methyl bicyclononadiene and the non-reactive raw material to the container in Step 1 to reuse those, wherein Steps 1 to 4 are consecutively repeatedly performed.

3 . The process for producing cyanonorbornene according to claim 1 ,
wherein the reaction product obtained in Step 2 includes 0.5% by weight to 28% by weight of the methyl bicyclononadiene with respect to a total amount of 100% by weight of the cyanonorbornene, the methyl bicyclononadiene, and a non-reactive raw material.

4 . The process for producing cyanonorbornene according to claim 1 ,
wherein a reaction temperature in Step 2 is 160° C. to 220° C.

5 . A process for producing an amine compound, comprising:
a step of preparing cyanonorbornene by the process for producing according to claim 1 ; a step of causing hydroformylation reaction of the cyanonorbornene with carbon monoxide and hydrogen; and a step of causing imination by reacting an aldehyde compound obtained in the hydroformylation step with ammonia and reacting thereof with hydrogen in the presence of a catalyst.

6 . A process for producing an isocyanate compound, comprising:
a step of preparing an amine compound by the process for producing according to claim 5 ; and a step of reacting the amine compound with a carbonylating agent.

Assignees

• Mitsui Chemicals Inc

Inventors

• Kuma Shigetoshi
• Sanda Tomoya

Classifications

• C07C209/48 Primary

  by reduction of nitriles · CPC title

• C07C255/47

  to carbon atoms of rings being part of condensed ring systems · CPC title

• C07C253/30 Primary

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

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title

• C07C263/10

  by reaction of amines with carbonyl halides, e.g. with phosgene · CPC title