Bis-phosphonium salt and process for producing the same

Details Bis-phosphonium salt and process for producing the same Bis-phosphonium salt and process for producing the same

2003-12-24

2004-08-10

Vollano, Jean F (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Phosphorus containing

C568S009000

Reexamination Certificate

active

06774265

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a new bis-phosphonium salt useful for producing intermediates of various organic phosphorus compounds such as flame retardants and optically active bis-phosphines and also relates to a process for producing the bis-phosphonium salt.
2. Discussion of the Related Art
Organic phosphorus compounds have been widely used for pharmaceuticals, agricultural chemicals, flame retardants, and catalysts for asymmetric synthesis. The bis-phosphonium salt disclosed herein can be converted into various organic phosphorus compounds having two phosphorus atoms according to, for example, the following reaction scheme (I):
wherein the symbol * represents an asymmetric atom.
For example, phosphine oxide represented by formula (5) in scheme (I) has a high phosphorus content and is therefore useful for flame retardants. The organic phosphorus compound represented by formula (7) in scheme (I) has asymmetric phosphorus atoms and functions as a bis-phosphine ligand having a 1,2-bis(phosphino) ethane skeleton. As is known, bis-phosphine ligands have high asymmetric selectivity and catalytic activity and therefore function as satisfactory catalysts for asymmetric hydrogenation reactions.
As an example of bis-phosphonium salts functioning as antistatic agents, bis-phosphonium bis-sulfonate represented by the following formula (8) is disclosed in pages 1 and 5 of Japanese Unexamined Patent Application Publication No. 7-70361 hereinafter referred to as Patent Document 1):
wherein R represents an alkyl group, aryl group, or aralkyl group having 1 to 18 carbon atoms, Z represents an alkylene group having 1 to 6 carbon atoms, and R
7
represents an alkyl group having 1 to 40 carbon atoms.
The bis-phosphonium bis-sulfonate is different from the bis-phosphonium salt, represented by formula (1) in scheme (I), according to the present invention.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a bis-phosphonium salt that is a new compound useful for producing various organic phosphorus compounds and represented by formula (1). It is another object of the present invention to provide a process for producing the bis-phosphonium salt.
A first aspect of the present invention provides a bis-phosphonium salt represented by the following formula (1):
wherein R
1
, R
2
, R
3
, and R
4
each represent a linear or branched alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group; A represents an alkylene group; Y represents an anion; R
1
and R
2
may form a ring; R
3
and R
4
may form a ring; and R
1
, R
2
, R
3
, and R
4
may be the same or different.
A second aspect of the present invention provides a process for producing a bis-phosphonium salt includes a step of allowing a first secondary phosphine and second secondary phosphine to react with a compound in an alcohol solvent selected from a secondary alcohol and tertiary alcohol. The bis-phosphonium salt is represented by the following formula (1):
wherein the first secondary phosphine is represented by the following formula (3):
the second secondary phosphine is represented by the following formula (4):
and the compound is represented by the following formula (5):
Y—A—Y  (5)
where R
1
, R
2
, R
3
, and R
4
each represent a linear or branched alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group; A represents an alkylene group; Y represents an anion; R
1
and R
2
may form a ring; R
3
and R
4
may form a ring; and R
1
, R
2
, R
3
, and R
4
may be the same or different.
The bis-phosphonium salt represented by formula (1) according to the present invention is a new compound and is useful for producing various phosphorus compounds, particularly flame retardants and bis-phosphonium ligands having a 1,2-bis(phosphino)ethane skeleton.
According to a process of the present invention, the bis-phosphonium salt can be selectively produced at high yield. Such a process is industrially advantageous.


REFERENCES:
patent: 2862971 (1958-12-01), Thielen et al.
patent: 3364107 (1968-01-01), Berenson et al.
patent: 3957978 (1976-05-01), Gastrock et al.
patent: 4620020 (1986-10-01), Schmidbaur et al.
patent: 4692504 (1987-09-01), Frank
patent: 7-70361 (1995-03-01), None
patent: 10-114782 (1998-05-01), None
patent: 10-147590 (1998-06-01), None
CA:72:132860 abs of Journal of Pharmacy and Phamacology by Clark et al 22(4) pp 279-283 1970.*
H. Hays, “The Controlled Alkylation of Mono-n-alkylphosphines”, Journal of Organic Chemistry, Nov. 1966, pp. 3817-3820, vol. 31.

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