Preparation method of aldehyde compound using a metal compound and a phosphorus compound

Patent metadata

Field	Value
Publication number	US-9475760-B2
Application number	US-201314440976-A
Country	US
Kind code	B2
Filing date	Nov 8, 2013
Priority date	Nov 9, 2012
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

Abstract

A preparation method of an aldehyde compound of the present invention includes a step of reacting the compound represented by the following general formula (a1) or (a2) with hydrogen and carbon monoxide in the presence of a metal compound including 0.01 ppmmol to 10 ppmmol of a metal belonging to Groups 8 to 10 with respect to 1 mole of the compound and a phosphorus compound, and the amount of a chlorine portion in the reaction system in the step is equal to or less than 1.5 parts by weight with respect to 1 part by weight of the metal belonging to Groups 8 to 10.

First claim

The invention claimed is:

1. A preparation method of an aldehyde compound, comprising:
a step of reacting a compound represented by formula (a1) or (a2) with hydrogen and carbon monoxide in the presence of a metal compound including 0.01 ppmmol to 10 ppmmol of a metal belonging to Groups 8 to 10 with respect to 1 mole of the compound represented by formula (a1) or (a2) and a phosphorus compound to prepare the aldehyde compound,
wherein the amount of a chlorine portion in the reaction system in the step is equal to or more than 0.1 parts by weight and equal to or less than 1.5 parts by weight with respect to 1 part by weight of the metal belonging to Groups 8 to 10,

wherein X represents a hydrogen atom, a cyano group, an aldehyde group, or a —CH═NR group, R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group, and n represents 0, 1 or 2 and
wherein the aldehyde compound is represented by formula (b1) when compound (a1)) is reacted and the aldehyde compound is represented by formula (b2) when compound (a2) is reacted,

2. The preparation method of an aldehyde compound according to claim 1 ,
wherein the metal compound including the metal belonging to Groups 8 to 10 is a rhodium compound, a cobalt compound, a ruthenium compound, or an iron compound.

3. The preparation method of an aldehyde compound according to claim 1 ,
wherein the metal compound including the metal belonging to Groups 8 to 10 is a rhodium compound.

4. The preparation method of an aldehyde compound according to claim 1 ,
wherein the amount of the metal belonging to Groups 8 to 10 is 1 ppmmol to 5 ppmmol with respect to 1 mole of the compound represented by formula (a1) or (a2).

5. The preparation method of an aldehyde compound according to claim 1 ,
wherein the phosphorus compound is a trivalent phosphorus compound.

6. The preparation method of an aldehyde compound according to claim 1 ,
wherein the compound represented by formula (a1) is used, and the is represented by formula (1),

wherein X is the same as that in the general formula (a1).

Assignees

• Mitsui Chemicals Inc

Inventors

• Tokunaga Koichi
• Kakinuma Naoyuki
• Kuma Shigetoshi

Classifications

• B01J25/00 Primary

  Catalysts of the Raney type · CPC title

• C07C263/10

  by reaction of amines with carbonyl halides, e.g. with phosgene · CPC title

• C07C211/38

  containing condensed ring systems · CPC title

• B01J2231/321

  Hydroformylation, metalformylation, carbonylation or hydroaminomethylation · CPC title

• C07C255/47 Primary

  to carbon atoms of rings being part of condensed ring systems · CPC title