US 7,547,807 B2
Method for producing phosphonium salts
Laszlo Szarvas, Ludwigshafen (Germany); Klemens Massonne, Bad Dürkheim (Germany); Harald Laas, Maxdorf (Germany); Kai Michael Exner, Eppelheim (Germany); and Detlev Glas, Frankenthal (Germany)
Assigned to BASF SE, Ludwigshafen (Germany)
Appl. No. 10/582,912
PCT Filed Dec. 14, 2004, PCT No. PCT/EP2004/014207
§ 371(c)(1), (2), (4) Date Jun. 14, 2006,
PCT Pub. No. WO2005/058924, PCT Pub. Date Jun. 30, 2005.
Claims priority of application No. 103 59 434 (DE), filed on Dec. 17, 2003.
Prior Publication US 2007/0123726 A1, May 31, 2007
Int. Cl. C07C 315/00 (2006.01)
U.S. Cl. 568—9 17 Claims
 
1. A process for preparing a quaternary phosphonium salt comprising reacting a trialkyl-, trialkenyl- or triarylphosphine with an optionally substituted monounsaturated or polyunsaturated aliphatic, cycloaliphatic aromatic-aliphatic alcohol having from 3 to 25 carbon atoms or its carboxylic acid esters or ethers in the presence of an acid, or by reacting a trialkyl, trialkenyl- or triarylphosphine with an optionally substituted aliphatic, cycloaliphatic or aromatic-aliphatic halide having from 3 to 25 carbon atoms, wherein the reaction is conducted in a ternary solvent mixture, and
wherein the quaternary phosphonium salt is of general formula I
[R1—P(R2)3]+X  (I),
where
R1 is an optionally substituted monounsaturated or polyunsaturated aliphatic, cycloaliphatic or aromatic-aliphatic group having from 3 to 25 carbon atoms,
R2 is an alkyl, alkenyl or aryl group having from 1 to 9 carbon atoms,
X is an anion equivalent of an organic or inorganic acid and
the trialkyl-, trialkenyl- or triarylphosphine is of general formula II
P(R2)3   (II),
where R2 has the meaning given above, and the triakyl-, trialkenyl-, or triarylphosphine is reacted with a monounsaturated or polyunsaturated electophile of the general formula III or IV,

OG Complex Work Unit Drawing
where R1 has the meaning given above, and
R1′ is an optionally substituted, aliphatic, cycloaliphatic or aromatic-aliphatic hydrocarbon group having from 1 to 21 carbon atoms,
Y is OH, Cl, Br, O(CO)R3 or OR3 and R3 is an aliphatic hydrocarbon group having from 1 to 6 carbon atoms, and
R4 is H or CH3 and, when an electrophile of the general formula IV is reacted,
R1 in formula I is a structural element of the general formula V

OG Complex Work Unit Drawing
where R1′ and R4 have the meanings given above.