# US 10,246,404 B2 · Bifunctional compound having norbornane skeleton and production method therefor

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- Number: US 10,246,404 B2
- Document ID: US10246404B2
- Status: Granted
- Kind: B2
- Application number: 15/560,713
- Filed: 2016-03-25
- Published: 2018-02-22
- Granted: 2019-04-02
- Earliest claimed: 2015-03-25
- Assignees: Mitsubishi Gas Chemical Company, Inc.
- Applicants: Mitsubishi Gas Chemical Company, Inc.
- Inventors: Taku Watanabe; Takashi Motoi; Yasuaki Yoshimura
- Web page: https://patentgrep.com/patent/US10246404B2

## CPC

- C07C 69/757: 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
- C07C 67/31: by introduction of functional groups containing oxygen only in singly bound form
- C07C 67/313: by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
- C07C 2603/86: containing four rings
- C08G 63/06: derived from hydroxycarboxylic acids
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The bifunctional compound according to the present invention is represented by the following formula (1): wherein R1 is a hydrogen atom, CH3, or C2H5; R2 and R3 are each independently a hydrogen atom or CH3; and X is a hydrogen atom or a hydrocarbon group having no more than 4 carbon atoms and optionally containing a hydroxyl group.

## Claims

### Claim 1

A bifunctional compound, represented by formula (1):
wherein
R1 is a hydrogen atom, CH3, or C7H5;
R2 and R3 are each independently a hydrogen atom or CH3; and
X is a hydrogen atom or a hydrocarbon group comprising no more than 4 carbon atoms and optionally a hydroxyl group.

### Claim 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
R1 is a hydrogen atom, CH3, or C2H5;
R2 and R3 are each independently a hydrogen atom or CH3; and
X is a hydrogen atom or a hydrocarbon group comprising no more than 4 carbon atoms and optionally a hydroxyl group.

### Claim 3 (depends on 2)

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.

### Claim 4 (depends on 2)

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 R1, R2, R3, and X are as defined in the formulae (1) and (2).

### Claim 5 (depends on 4)

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.