Bis(6-methyl-3-sulphophenyl)phenylphosphine, ammonium salt thereof, and method for producing same

Patent metadata

Field	Value
Publication number	US-10696701-B2
Application number	US-201815872550-A
Country	US
Kind code	B2
Filing date	Jan 16, 2018
Priority date	Mar 27, 2013
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

Provided are a water-soluble triarylphosphine for a palladium catalyst, which has high selectivity in a telomerization reaction and can be recovered with efficiency, an ammonium salt thereof, and a method for efficiently producing the same. Specifically, provided are bis(6-methyl-3-sulphophenyl)phenylphosphine; a bis(6-methyl-3-sulphonatopheyl)phenylphosphine diammonium salt obtained by reacting the phosphine with a tertiary amine having a total of 3 to 27 carbon atoms in groups bonded to one nitrogen atom; and a method for producing the same.

First claim

The invention claimed is:

1. A method of performing a telomerization reaction, comprising reacting an alkadiene with water in the presence of a solid bis(6-methyl-3-sulphonatophenyl)phenylphosphine diammonium salt,
wherein the solid bis(6-methyl-3-sulphonatophenyl)phenylphosphine diammonium salt is obtained by a process comprising: reacting bis(6-methyl-3-sulphophenyl)phenylphosphine with a tertiary amine comprising a total of 3 to 27 carbon atoms in groups bonded to one nitrogen atom.

2. The method of claim 1 , wherein the tertiary amine is at least one selected from the group consisting of trimethylamine, triethylamine, tripropylamine, triisopropylamine, tributylamine, triisobutylamine, tri-s-butylamine, tri-t-butylamine, tripentylamine, triisopentylamine, trineopentylamine, trihexylamine, triheptylamine, trioctylamine, triphenylamine, tribenzylamine, N,N-dimethylethylamine, N,N-dimethylpropylamine, N,N-dimethylisopropylamine, N,N-dimethylbutylamine, N,N-dimethylisobutylamine, N,N-dimethyl-s-butylamine, N,N-dimethyl-t-butylamine, N,N-dimethylpentylamine, N,N-dimethylisopentylamine, N,N-dimethylneopentylamine, N,N-dimethylhexylamine, N,N-dimethylheptylamine, N,N-dimethyloctylamine, N,N-dimethylnonylamine, N,N-dimethyldecylamine, N,N-dimethylundecylamine, N,N-dimethyldodecylamine, N,N-dimethylphenylamine, N,N-dimethylbenzylamine N,N-diethylmonomethylamine, N,N-dipropylmonomethylamine, N,N-diisopropylmonomethylamine, N,N-dibutylmonomethylamine, N,N-diisobutylmonomethylamine, N,N-di-s-butylmonomethylamine, N,N-di-t-butylmonomethylamine, N,N-dipentylmonomethylamine, N,N-diisopentylmonomethylamine, N,N-dineopentylmonomethylamine, N,N-dihexylmonomethylamine, N,N-diheptylmonomethylamine, N,N-dioctylmonomethylamine, N,N-dinonylmonomethylamine, N,N-didecylmonomethylamine, N,N-diundecylmonomethylamine, N,N-didodecylmonomethylamine, N,N-diphenylmonomethylamine, N,N-dibenzylmonomethylamine, N,N-dipropylmonomethylamine, N,N-diisopropylmonoethylamine, N,N-dibutylmonoethylamine, N,N-diisobutylmonoethylamine, N,N-di-s-butylmonoethylamine, N,N-di-t-butylmonoethylamine, N,N-dipentylmonoethylamine, N,N-diisopentylmonoethylamine, N,N-dineopentylmonoethylamine, N,N-dihexylmonoethylamine, N,N-diheptylmonoethylamine, N,N-dioctylmonoethylamine, N,N-dinonylmonoethylamine, N,N-didecylmonoethylamine, N,N-diundecylmonoethylamine, N,N-didodecylmonoethylamine, N,N-diphenylmonoethylamine, N,N-dibenzylmonoethylamine, and trinonylamine.

3. The method of claim 1 , wherein the tertiary amine comprises a total of 5 to 7 carbon atoms in groups bonded to one nitrogen atom.

4. The method of claim 1 , wherein the tertiary amine is at least one selected from the group consisting of triethylamine and N,N-dimethylisopropylamine.

5. The method of claim 1 , wherein the tertiary amine comprises triethylamine.

6. The method of claim 1 , wherein the alkadiene comprises butadiene.

7. The method of claim 6 , wherein the reacting of the alkadiene with water in the presence of the solid bis(6-methyl-3-sulphonatophenyl)phenylphosphine diammonium salt produces at least one product selected from the group consisting of 2,7-octadien-1-ol, 1,7-octadien-3-ol, 1,3,6-octatriene, 1,3,7-octatriene, 2,4,6-octatriene, and 4-vinylcyclohexene.

8. The method of claim 6 , wherein the reacting of the alkadiene with water in the presence of the solid bis(6-methyl-3-sulphonatophenyl)phenylphosphine diammonium salt produces 2,7-octadien-1-ol.

9. The method of claim 1 , wherein the reacting of the alkadiene with water in the presence of the solid bis(6-methyl-3-sulphonatophenyl)phenylphosphine diammonium salt produces at least one product selected from the group consisting of 2,7-octadien-1-ol, 1,7-octadien-3-ol, 1,3,6-octatriene, 1,3,7-octatriene, 2,4,6-octatriene, and 4-vinylcyclohexene.

10. The method of claim 1 , wherein the reacting of the alkadiene with water in the presence of the solid bis(6-methyl-3-sulphonatophenyl)phenylphosphine diammonium salt produces 2,7-octadien-1-ol.

Assignees

• Kuraray Co
• Hokko Chem Ind Co

Inventors

• Honda Eriko
• Yoshikawa Tatsuya
• Tsuji Tomoaki
• Koizumi Hitoshi
• Sugita Kyoko
• KUMAMOTO Nobumichi

Classifications

• Y02P20/584

  Recycling of catalysts · CPC title

• C07F9/5022 Primary

  Aromatic phosphines (P-C aromatic linkage) · CPC title

• C07C211/08

  containing alkyl groups having a different number of carbon atoms · CPC title

• C07C211/07

  containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three · CPC title

• B01J31/0225

  comprising sulfonic acid groups or the corresponding salts · CPC title