Bifunctional compound having norbornane skeleton and method for producing same

Patent metadata

Field	Value
Publication number	US-10343973-B2
Application number	US-201816170113-A
Country	US
Kind code	B2
Filing date	Oct 25, 2018
Priority date	Mar 28, 2014
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

Abstract

A method for producing a bifunctional compound of formula (3)

wherein R 2 represents H, CH 3 or C 2 H 5 ,
the method comprising reducing a bifunctional compound of formula (1):

wherein R 1 represents COOCH 3 , COOC 2 H 5 , COOC 3 H 7 , COOC 4 H 9 , or CHO; and R 2 represents H, CH 3 or C 2 H 5 , provided that when R 1 represents CHO, R 2 represents C 2 H 5 , in the presence of a catalyst having hydrogenation activity and hydrogen.

First claim

The invention claimed is:

1. A method for producing a bifunctional compound of formula (3):

wherein R 2 represents H, CH 3 or C 2 H 5 ,
the method comprising reducing a bifunctional compound of formula (1):

wherein R 1 represents COOCH 3 , COOC 2 H 5 , COOC 3 H 7 , COOC 4 H 9 or CHO; and R 2 represents H, CH 3 or C 2 H 5 , provided that when R 1 represents CHO, R 2 represents C 2 H 5 , in the presence of a catalyst having hydrogenation activity and hydrogen.

2. The method according to claim 1 , wherein the catalyst having hydrogenation activity comprises at least one element selected from the group consisting of copper, chromium, iron, zinc, aluminium, nickel, cobalt and palladium.

3. The method according to claim 1 , further comprising producing the bifunctional compound of (1) by subjecting a monoolefin of formula (2):

wherein R 1 represents COOCH 3 , COOC 2 H 5 , COOC 3 H 7 , COOC 4 H 9 or CHO; and R 2 represents H, CH 3 or C 2 H 5 , provided that when R 1 represents CHO, R 2 represents C 2 H 5 , carbon monoxide and hydrogen gases to a hydroformylation reaction in the presence of a rhodium compound and an organic phosphorous compound.

4. The method according to claim 3 , further comprising performing the hydroformylation reaction using: the rhodium compound in an amount of 0.1 to 60 μmol relative to 1 mol of the monoolefins of formula (2); and the organic phosphorous compound in an amount of 300 to 10000 times the molar quantity of the rhodium compound.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Motoi Takashi
• Kitamura Mitsuharu
• Hirakawa Manabu

Classifications

• C08G64/0208

  saturated · CPC title

• C07C69/757 Primary

  having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] in the acid moiety · CPC title

• C07C69/753

  of polycyclic acids · CPC title

• C07C67/347

  by addition to unsaturated carbon-to-carbon bonds · CPC title

• C07C47/347

  having a —CHO group on a condensed ring system · CPC title