Bis(6-methyl-3-sulphophenyl)(2-methylphenyl)phosphine, ammonium salt thereof, and method for producing same

Patent metadata

Field	Value
Publication number	US-11021499-B2
Application number	US-201816183001-A
Country	US
Kind code	B2
Filing date	Nov 7, 2018
Priority date	Mar 27, 2013
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

Provided are a water-soluble triarylphosphine for a palladium catalyst, which has high selectivity in a telomerization reaction and is easily recovered with efficiency, an ammonium salt thereof, and a method for efficiently producing the same. Specifically, provided are bis(6-methyl-3-sulphophenyl)(2-methylphenyl)phosphine; a bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine 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, consisting essentially of:
reacting an alkadiene comprising butadiene with water in the presence of a bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine diammonium salt, palladium compound, a tertiary amine, and carbon dioxide,
wherein the bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine diammonium salt is obtained by reacting bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine with a tertiary amine having a total of 3 to 27 carbon atoms in groups bonded to one nitrogen atom, and
wherein in a product of the reacting of the alkadiene with water, a molar ratio of 2,7-octadien-1-ol to a total of 2,7-octadien-1-ol and 1,7-octadien-3-ol is at least 96.7%.

2. The method of claim 1 , wherein the tertiary amine is 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 2 , wherein the tertiary amine reacted with bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine is trioctylamine.

4. The method of claim 1 , wherein the tertiary amine reacted with bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine has a total of 5 to 10 carbon atoms in groups bonded to one nitrogen atom.

5. The method of claim 4 , wherein the tertiary amine reacted with bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine is selected from the group consisting of triethylamine, tripropylamine, triisopropylamine, 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, and N,N-dimethyloctylamine.

6. The method of claim 1 , wherein the tertiary amine reacted with bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine has a total of 5 to 7 carbon atoms in groups bonded to one nitrogen atom.

7. The method of claim 6 , wherein the tertiary amine reacted with bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine is selected from the group consisting of triethylamine, 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, and N,N-dimethylneopentylamine.

8. The method of claim 7 , wherein the tertiary amine reacted with bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine is triethylamine.

9. The method of claim 7 , wherein the tertiary amine reacted with bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine is N,N-dimethylisopropylamine.

10. A method of performing a telomerization reaction, comprising:
reacting an alkadiene comprising butadiene with water in the presence of a bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine diammonium salt, palladium compound, a tertiary amine, and carbon dioxide,
wherein the bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine diammonium salt is obtained by reacting bis(6-methyl-3-sulphophenyl)(2-methlyphenyl)phosphine with a tertiary amine having a total of 3 to 27 carbon atoms in groups bonded to one nitrogen atom, and
wherein in a product of the reacting of the alkadiene with water, a molar ratio of 2,7-octadien-1-ol to a total of 2,7-octadien-1-ol and 1,7-octadien-3-ol is at least 96.7%.

11. The method of claim 10 , wherein a noble metal is present during the reacting of the alkadiene with water.

12. The method of claim 11 , wherein the noble metal comprises palladium.

13. The method of claim 12 , further comprising:
recovering the palladium; and
reusing the recovered palladium in the reacting of the alkadiene with water.

14. The method of claim 10 , wherein triethylamine is present during the reacting of the alkadiene with water.

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

• B01J31/0267

  Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen · 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

• C07C211/08

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