Bifunctional compound having norbornane skeleton and method for producing same

Patent metadata

Field	Value
Publication number	US-9975843-B2
Application number	US-201515127969-A
Country	US
Kind code	B2
Filing date	Mar 27, 2015
Priority date	Mar 28, 2014
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

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

where 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 , by subjecting a monoolefin of formula (2):

where 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 , carbon monoxide and hydrogen gases to a hydroformylation reaction in the presence of a rhodium compound and an organic phosphorous compound. Compounds produced.

First claim

The invention claimed is:

1. A method for producing 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 ,
the method comprising 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.

2. The method according to claim 1 , further comprising producing the monoolefin of formula (2) by a Diels-Alder reaction of dicyclopentadiene with CH 2 ═CR 1 R 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 .

3. The method according to claim 1 , comprising performing the hydroformylation reaction using: the rhodium compound in an amount of 0.1 to 60 μmol relative to 1 mol of the monoolefin of formula (2); and the organic phosphorous compound in an amount of 300 to 10,000 times the molar quantity of the rhodium compound.

4. The method according to claim 1 , wherein a pressure at the time of hydroformylation of the monoolefin of formula (2) is 1 to 12 MPa.

5. The method according to claim 1 , comprising supplying the monoolefin of formula (2) or a solution thereof to a solution comprising the rhodium compound, the organic phosphorous compound and a solvent under an atmosphere comprising carbon monoxide and hydrogen gases.

6. The method according to claim 1 , further comprising isolating the bifunctional compound of formula (1) from a reaction solution after the hydroformylation reaction by distillation.

7. The method according to claim 1 , wherein R 1 in formula (1) and formula (2) represents COOCH 3 .

8. The method according to claim 1 , wherein R 1 in formula (1) and formula (2) represents COOC 2 H 5 .

9. The method according to claim 1 , wherein R 1 in formula (1) and formula (2) represents COOC 3 H 7 .

10. The method according to claim 1 , wherein R 1 in formula (1) and formula (2) represents COOC 4 H 9 .

11. The method according to claim 1 , wherein R 1 in formula (1) and formula (2) represents CHO.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Motoi Takashi
• Kitamura Mitsuharu
• Hirakawa Manabu

Classifications

• C07C45/50

  by oxo-reactions · 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

• C07C47/347

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

• C07C69/753

  of polycyclic acids · CPC title

• C07C67/347

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