Bifunctional compound having norbornane skeleton and production method therefor

Patent metadata

Field	Value
Publication number	US-10246404-B2
Application number	US-201615560713-A
Country	US
Kind code	B2
Filing date	Mar 25, 2016
Priority date	Mar 25, 2015
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

The bifunctional compound according to the present invention is represented by the following formula (1):

wherein R 1 is a hydrogen atom, CH 3 , or C 2 H 5 ; R 2 and R 3 are each independently a hydrogen atom or CH 3 ; and X is a hydrogen atom or a hydrocarbon group having no more than 4 carbon atoms and optionally containing a hydroxyl group.

First claim

The invention claimed is:

1. A bifunctional compound, represented by formula (1):

wherein
R 1 is a hydrogen atom, CH 3 , or C 7 H 5 ;
R 2 and R 3 are each independently a hydrogen atom or CH 3 ; and
X is a hydrogen atom or a hydrocarbon group comprising no more than 4 carbon atoms and optionally a hydroxyl group.

2. A method for producing a bifunctional compound represented by formula (I), the method comprising
reducing a bifunctional compound represented by formula (2) in the presence of a catalyst having hydrogenation capability and hydrogen:

wherein
R 1 is a hydrogen atom, CH 3 , or C 2 H 5 ;
R 2 and R 3 are each independently a hydrogen atom or CH 3 ; and
X is a hydrogen atom or a hydrocarbon group comprising no more than 4 carbon atoms and optionally a hydroxyl group.

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

4. The method according to claim 2 , further comprising
subjecting a monoolefin represented by formula (3) to a hydroformylation reaction with carbon monoxide and hydrogen gas in the presence of a rhodium compound and an organophosphorus compound to obtain the bifunctional compound represented by the above formula (2):

wherein R 1 , R 2 , R 3 , and X are as defined in the formulae (1) and (2).

5. The method according to claim 4 , wherein in the hydroformylation reaction, 0.1 to 60 micromoles of the rhodium compound is used per mol of the monoolefin, and the organophosphorus compound is used in an amount of 300 to 10000 mol per mol of rhodium atoms in the rhodium compound.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Watanabe Taku
• Motoi Takashi
• Yoshimura Yasuaki

Classifications

• C08G63/06

  derived from hydroxycarboxylic acids · CPC title

• C07C67/31

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C07C67/313

  by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups · 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

• C07C2603/86

  containing four rings · CPC title