Process for producing aldehyde compounds

Patent metadata

Field	Value
Publication number	US-9227925-B2
Application number	US-201214114774-A
Country	US
Kind code	B2
Filing date	May 7, 2012
Priority date	May 9, 2011
Publication date	Jan 5, 2016
Grant date	Jan 5, 2016

Abstract

A process for producing an aldehyde compound of the invention comprising: reacting a compound represented by the following formula (a1) or (a2) with a hydrogen and a carbon monoxide in a presence of a compound containing a metal belonging to Groups 8 to 10 and a phosphorous compound so as to satisfy the following conditions (1) and (2) to synthesize an aldehyde compound;
wherein the condition (1) is that a content of a metal included in the compound containing a metal belonging to Groups 8 to 10 is 0.01 ppmmol to 300 ppmmol with respect to 1 mol of the compound represented by the formula (a1) or (a2), and wherein the condition (2) is that a molar ratio represented by the phosphorous compound (mol)/the metal (mol) is 100 or more;

First claim

The invention claimed is:

1. A process for producing an aldehyde compound represented by the following formula (b1) or the following formula (b2) comprising:
a step of reacting a compound represented by the following formula (a1) or the following formula (a2) with a hydrogen and a carbon monoxide in a presence of a compound containing a metal belonging to Groups 8 to 10 and a phosphorous compound so as to satisfy the following conditions (1) and (2);
wherein the condition (1) is that a content of a metal included in the compound containing a metal belonging to Groups 8 to 10 is 0.015 ppm mol to 100 ppm mol with respect to 1 mol of the compound represented by the following formula (a1) or (a2), and
wherein the condition (2) is that a molar ratio represented by the phosphorous compound (mol)/the metal (mol) is 150 or more,

wherein, in the formula (a1), X represents a hydrogen atom, a cyano group, an aldehyde group or —CH═NR group, and R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an aryl group; in the formula (a1) and the formula (a2), n represents 0, 1 or 2,

wherein n and X are previously described, and
wherein the reacting step further satisfies the condition (3) in which is that a molar ratio of “the phosphorous compound (mol)” to “the compound (mol) represented by the formula (a1) or (a2)” is 0.003 to 0.05.

2. The process for producing the aldehyde compound according to claim 1 ,
wherein the compound containing a metal belonging to Groups 8 to 10 is a rhodium compound, a cobalt compound, a ruthenium compound or an iron compound.

3. The process for producing the aldehyde compound according to claim 1 ,
wherein the compound containing a metal belonging to Groups 8 to 10 is a rhodium compound.

4. The process for producing the aldehyde compound according to claim 1 ,
wherein the compound represented by the formula (a1) is used, and the compound is represented by the following formula (1)

wherein, in the formula (1), X is the same as in the formula (a1).

5. The process for producing the aldehyde compound according to claim 1 ,
wherein the phosphorous compound is a trivalent phosphorous compound.

6. The process for producing the aldehyde compound according to claim 5 ,
wherein the trivalent phosphorous compound is selected from group consisting of triphenyl phosphite, triphenyl phosphine, trimethyl phosphine, triethyl phosphine, tripropyl phosphine, tri(methylbenzene)phosphine, tri(ethylbenzene)phosphine, 1,2-bis(diphenylphosphino)ethylene, 1,3-bis(diphenylphosphino)propane, 2,2-bis(diphenylphosphino)-1,1-binaphthyl, trimethoxy phosphite, triethoxy phosphite, tripropoxy phosphite, triisopropoxy phosphite, trimethyl phenyl phosphite and tris(2,4-ditert-butylphenyl)phosphite.

7. The process for producing the aldehyde compound according to claim 1 ,
wherein the reacting step is carried out under solventless condition.

8. A process for producing an amine compound represented by the following formula (c1) or the following formula (c2) comprising:
a step (a) of reacting a compound represented by the following formula (a1) or the following formula (a2) with a hydrogen and a carbon monoxide in a presence of a compound containing a metal belonging to Groups 8 to 10 and a phosphorous compound so as to satisfy the following conditions (1) and (2) to synthesize an aldehyde compound represented by the following formula (b1) or the following formula (b2); and
a step (b) of reacting the aldehyde compound with an ammonia, and reacting with a hydrogen in a presence of a catalyst;
wherein the condition (1) is that a content of a metal included in the compound containing a metal belonging to Groups 8 to 10 is 0.015 ppm mol to 100 ppm mol with respect to 1 mol of the compound represented by the following formula (a1) or (a2), and
wherein the condition (2) is that a molar ratio represented by the phosphorous compound (mol)/the metal (mol) is 150 or more,

wherein, in the formula (a1), X represents a hydrogen atom, a cyano group, an aldehyde group or —CH═NR group, and R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an aryl group; in the formula (a1) and the formula (a2), n represents 0, 1 or 2,

wherein n and X are previously described,

wherein n is previously described, and
wherein the step (a) further satisfies the condition (3) in which is that a molar ratio of “the phosphorous compound (mol)” to “the compound (mol) represented by the formula (a1) or (a2)” is 0.003 to 0.05.

9. The process for producing the amine compound according to claim 8 ,
wherein the compound containing a metal belonging to Groups 8 to 10 is a rhodium compound, a cobalt compound, a ruthenium compound or an iron compound.

10. The process for producing the amine compound according to claim 8 ,
wherein the compound containing a metal belonging to Groups 8 to 10 is a rhodium compound.

11. The process for producing the amine compound according to claim 8 ,
wherein the compound represented by the formula (a1) is used, and that compound is represented by the following formula (1);

wherein, in the formula (1), X is the same as in the formula (a1).

12. The process for producing the isocyanate compound according to claim 11 ,
wherein the phosphorous compound is selected from group consisting of triphenyl phosphite, triphenyl phosphine, trimethyl phosphine, triethyl phosphine, tripropyl phosphine, tri(methylbenzene)phosphine, tri(ethylbenzene)phosphine, 1,2-bis(diphenylphosphino)ethylene, 1,3-bis(diphenylphosphino)propane, 2,2-bis(diphenylphosphino)-1,1-binaphthyl, trimethoxy phosphite, triethoxy phosphite, tripropoxy phosphite, triisopropoxy phosphite, trimethyl phenyl phosphite and tris(2,4-ditert-butylphenyl)phosphite.

13. The process for producing the amine compound according to claim 8 ,
wherein the trivalent phosphorous compound is selected from group consisting of triphenyl phosphite, triphenyl phosphine, trimethyl phosphine, triethyl phosphine, tripropyl phosphine, tri(methylbenzene)phosphine, tri(ethylbenzene)phosphine, 1,2-bis(diphenylphosphino)ethylene, 1,3-bis(diphenylphosphino)propane, 2,2-bis(diphenylphosphino)-1,1-binaphthyl, trimethoxy phosphite, triethoxy phosphite, tripropoxy phosphite, triisopropoxy phosphite, trimethyl phenyl phosphite and tris(2,4-ditert-butylphenyl)phosphite.

14. A process for producing an isocyanate compound represented by the following formula (d1) or the following formula (d2) comprising:
a step (a) of reacting a compound represented by the following formula (a1) or the following formula (a2) with a hydrogen and a carbon monoxide in a presence of a compound containing a metal belonging to Groups 8 to 10 and a phosphorous compound so as to satisfy the following conditions (1) and (2) to synthesize an aldehyde compound represented by the following formula (b1) or the following formula (b

Assignees

• Kuma Shigetoshi
• Sakata Michiharu
• Tokunaga Kouichi
• Shimakawa Chitoshi
• Kakinuma Naoyuki
• Furuya Masayuki
• Tanaka Mamoru
• Mitsui Chemicals Inc

Inventors

• Kuma Shigetoshi
• Sakata Michiharu
• Tokunaga Kouichi
• Shimakawa Chitoshi
• Kakinuma Naoyuki
• Furuya Masayuki
• Tanaka Mamoru

Classifications

• C07C263/10

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

• C07C2102/42

  Chemistry & Metallurgy · mapped topic

• C07C265/14

  containing at least two isocyanate groups bound to the same carbon skeleton · CPC title

• C07C45/49

  by reaction with carbon monoxide · CPC title

• C07C253/30 Primary

  by reactions not involving the formation of cyano groups · CPC title