US 7,501,522 B2
Method for the production of purified 1,3-substituted imidazolium salts
Matthias Maase, Speyer (Germany); and Klemens Massonne, Bad Dürkheim (Germany)
Assigned to BASF Aktiengesellschaft, Ludwigshafen (Germany)
Appl. No. 10/564,871
PCT Filed Jun. 30, 2004, PCT No. PCT/EP2004/007076
§ 371(c)(1), (2), (4) Date Feb. 06, 2006,
PCT Pub. No. WO2005/019183, PCT Pub. Date Mar. 03, 2005.
Claims priority of application No. 103 33 239 (DE), filed on Jul. 21, 2003.
Prior Publication US 2006/0149074 A1, Jul. 06, 2006
Int. Cl. C07F 9/80 (2006.01); C07F 5/02 (2006.01)
U.S. Cl. 548—102  [548/107; 548/110] 14 Claims
 
1. A process for preparing purified 1,3-substituted imidazolium salts of the formula (I)

OG Complex Work Unit Drawing
where
the radicals R1, R2, R3 and R4 are each, independently of one another, a carbon-comprising organic, saturated or unsaturated, acyclic or cyclic, aliphatic, aromatic or araliphatic radical which has from 1 to 30 carbon atoms and may comprise one or more heteroatoms and/or be substituted by one or more functional groups or halogens, where adjacent radicals R1 and R2, R2 and R3 or R3 and R4 may also be joined to one another and the radicals R2 and R3 may each also be, independently of one another, hydrogen, halogen or a functional group;
and
Aa− is the partly or fully deprotonated anion of an inorganic or organic protic acid HaA (III), where a is a positive integer and indicates the charge on the anion,
which comprises reacting a 1,3-substituted imidazolium salt of the formula (II),

OG Complex Work Unit Drawing
where the radicals R1, R2, R3 and R4 are as defined above and
the anion Yy− is the partly or fully deprotonated anion of an inorganic or organic protic acid
HyY  (IV),
where y is a positive integer and indicates the charge on the anion,
with a strong base at from 20 to 250° C. while distilling off the 1,3-substituted imidazol-2-ylidene formed, wherein the 1,3-substituted imidazol-2-ylidene which has been distilled off is brought into contact in the gaseous state with the protic acid
HaA  (III)
and/or the 1,3-substituted imidazol-2-ylidene which has been distilled off is passed in the gaseous or condensed state into a receiver comprising the protic acid HaA (III).