Dihydroxybiphenyl compound, bisphosphite compound, catalyst, production method of aldehydes, and production method of alcohol

Patent metadata

Field	Value
Publication number	US-10793497-B2
Application number	US-202016794316-A
Country	US
Kind code	B2
Filing date	Feb 19, 2020
Priority date	Aug 24, 2017
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

An object of the present invention is to provide a bisphosphite compound giving higher selectivity for the target product with maintaining a high reaction rate. The present invention relates to a dihydroxybiphenyl compound represented by the following formula (1) and a bisphosphite compound represented by the following formula (2):

wherein in formulae (1) and (2), each of R 1 to R 4 , R 11 to R 14 , and Z 1 to Z 4 is the same as defined in the description.

First claim

The invention claimed is:

1. A bisphosphite compound represented by the following formula (2):

wherein in formula (2), each of R 1 and R 11 independently represents a member selected from the group consisting of a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, and a cycloalkyl group having from 3 to 20 carbon atoms;
each of R 2 and R 12 independently represents a member selected from the group consisting of a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, an alkoxy group having from 1 to 20 carbon atoms, a cycloalkyl group having from 3 to 20 carbon atoms, a cycloalkoxy group having from 3 to 20 carbon atoms, a dialkylamino group having from 2 to 20 carbon atoms, an aryl group having from 6 to 20 carbon atoms, an aryloxy group having from 6 to 20 carbon atoms, an alkylaryl group having from 7 to 20 carbon atoms, an alkylaryloxy group having from 7 to 20 carbon atoms, an arylalkyl group having from 7 to 20 carbon atoms, an arylalkoxy group having from 7 to 20 carbon atoms, a cyano group, a hydroxy group, and a halogen atom;
each of R 3 and R 13 independently represents a member selected from the group consisting of a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms, a cycloalkyl group having from 3 to 20 carbon atoms, an aryl group having from 6 to 20 carbon atoms, an alkylaryl group having from 7 to 20 carbon atoms, and an arylalkyl group having from 7 to 20 carbon atoms;
each of R 4 and R 14 independently represents a member selected from the group consisting of a hydrogen atom, an alkyl group having from 1 to 12 carbon atoms, a cycloalkyl group having from 3 to 12 carbon atoms, an alkoxy group having from 1 to 12 carbon atoms, a silyl group, a siloxy group, and a halogen atom; and
each of Z 1 to Z 4 independently represents an aryl group having from 6 to 20 carbon atoms and may have a substituent, and both of paired Z 1 and Z 2 and paired Z 3 and Z 4 are not combined.

2. The bisphosphite compound according to claim 1 , wherein each of R 1 and R 11 independently represents a tertiary alkyl group having from 4 to 20 carbon atoms, R 2 and R 12 represent a hydrogen atom, each of R 3 and R 13 independently represents a tertiary alkyl group having from 4 to 20 carbon atoms, each of R 4 and R 14 independently represents a member selected from the group consisting of an alkyl group having from 1 to 3 carbon atoms, an alkoxy group having from 1 to 3 carbon atoms, and a halogen atom.

3. The bisphosphite compound according to claim 2 , wherein each of Z 1 to Z 4 independently represents an aryl group having no substituent on the aromatic ring carbon atom adjacent to the carbon atom bonded to oxygen atom or an aryl group having a substituent having from 1 to 2 carbon atoms on the aromatic ring carbon atom.

4. The bisphosphite compound according to claim 3 , wherein each of R 1 , R 11 , R 3 and R 13 independently represents a tertiary alkyl group having from 4 to 7 carbon atoms and each of R 4 and R 14 independently represents an alkyl group having from 1 to 3 carbon atoms.

5. The bisphosphite compound according to claim 4 , wherein each of Z 1 to Z 4 independently represents a 1-naphthyl group or a 2-naphthyl group.

6. The bisphosphite compound according to claim 5 , wherein R 1 , R 11 , R 3 and R 13 represent a tert-butyl group and R 4 and R 14 represent a methyl group.

7. A catalyst comprising a complex of the bisphosphite compound according to claim 1 and a metal of Groups 8 to 10.

8. The catalyst according to claim 7 , wherein a molar ratio of the bisphosphite compound to the metal of Groups 8 to 10 is from 0.00004 to 500.

9. The catalyst according to claim 7 , wherein a molar ratio of the bisphosphite compound to the metal of Groups 8 to 10 is from 0.0002 to 100.

10. The catalyst according to claim 7 , wherein a molar ratio of the bisphosphite compound to the metal of Groups 8 to 10 is from 0.001 to 50.

11. A method for producing aldehydes, comprising reacting an olefin compound with carbon monoxide and hydrogen in the presence of a compound of a metal of Groups 8 to 10 and the bisphosphite compound according to claim 1 .

12. The production method of aldehydes according to claim 11 , wherein a concentration of the compound of a metal of Groups 8 to 10 in a reaction solution is from 0.05 to 5,000 mg/L in terms of metal atoms.

13. A method for producing aldehydes, comprising reacting an olefin compound with carbon monoxide and hydrogen in the presence of the catalyst according to claim 7 .

14. A method for producing an alcohol, comprising producing aldehydes by the production method of aldehydes according to claim 11 , and then reacting the aldehydes with hydrogen.

15. A method for producing an alcohol, comprising producing aldehydes by the production method of aldehydes according to claim 13 , and then reacting the aldehydes with hydrogen.

Assignees

• Mitsubishi Chem Corp

Inventors

• Tanaka Yoshiyuki

Classifications

• C07C47/02

  Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen · CPC title

• C07C43/23

  containing hydroxy or O-metal groups · CPC title

• B01J31/185

  Phosphites ((RO)3P) , their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof · CPC title

• C07C29/153 Primary

  characterised by the catalyst used · CPC title

• C07F15/008 Primary

  without a metal-carbon linkage · CPC title