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

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.

2 . A bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine diammonium salt obtained by reacting the bis(6-methyl-3-sulphophenyl)(2-methylphenyl)phosphine of claim  1  with a tertiary amine having a total of 3 to 27 carbon atoms in groups bonded to one nitrogen atom. 
     
     
         3 . The bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine diammonium salt of  claim 2 ,
 wherein the tertiary amine is 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.   
     
     
         4 . A mixture, comprising:
 5% by mole or less of bis(2-methylphenyl)(6-methyl-3-sulphophenyl)phosphine,   80% by mole or more of bis(6-methyl-3-sulphophenyl)(2-methylphenyl)phosphine, and   15% by mole or less of tris(6-methyl-3-sulphophenyl)phosphine.   
     
     
         5 . A mixture, comprising:
 80% by mole or more of a bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine diammonium salt obtained by reacting the mixture of  claim 4  with a tertiary amine having a total of 3 to 27 carbon atoms in groups bonded to one nitrogen atom.   
     
     
         6 . A method for producing the bis(6-methyl-3-sulphophenyl)(2-methylphenyl)phosphine of claim  1 , comprising:
 reacting 2.5 moles to 4.5 moles of sulphur trioxide with 1 mole of tris(2-methylphenyl)phosphine in the presence of concentrated sulphuric acid, thereby producing a sulphonation reaction liquid, and diluting the obtained sulphonation reaction liquid with water, thereby producing a diluted liquid;   neutralizing the diluted liquid with an alkali metal hydroxide, thereby producing an aqueous solution; and   bringing the aqueous solution into contact with a strongly acidic cation exchange resin.   
     
     
         7 . A method for producing a bis(6-methyl-3-sulphonatophenyl)(2-methylphenyl)phosphine diammonium salt. the method comprising:
 reacting the bis(6-methyl-3-sulphophenyl)(2-methylphenyl)phosphine of claim  1  with a tertiary amine having a total of 3 to 27 carbon atoms in groups bonded to one nitrogen atom.