C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/558.2
C07C 253/14 (2006.01) C07C 255/50 (2006.01)
Patent
CA 2010159
CYANATION OF HALOAROMATICS UTILIZING CATALYSTS GENERATED IN SITU STARTING WITH NiCl2 Or NiCl2?6H2O Abstract of the Disclosure Aromatic halide is converted to aromatic nitrile, e.g., p-chlorobenzotrifluoride is converted to 4-(trifluoromethyl)benzonitrile, utilizing Ni(P?3)3 as a catalyst where said catalyst is formed starting with NiCl2 or NiCl2?6H2O where formation of said catalyst starting with NiCl2 or NiCl2?6H2O and conversion of halide to nitrile are carried out in a single reactor vessel. The method comprises the steps of (a) forming catalyst by steps comprising (i) forming essentially dry Ni(P?3)Cl2 in situ in said reactor vessel starting with NiCl2 or NiCl2-6H2O, (ii) reacting said essentially dry Ni(P?3)2Cl2 with P?3 in the presence of a reducing metal in C2-C5 alcohol or aprotic polar reaction solvent in said reactor vessel to produce Ni(P?3)3 catalyst therein, and (b) adding said halide into said reactor vessel to form a complex in C2-C5 alcohol or aprotic polar reaction solvent from said halide and said catalyst and adding alkali metal cyanide to convert halogen to CN and thereby produce nitrile. When anhydrous NiCl2 is a starting material, steps (a)(i) and (a)(ii) are preferably carried out as a single step where anhydrous NiCl2 and at least three equivalents of P?3 are added to C2-C5 alcohol or aprotic polar solvent followed by addition of reducing metal powder and reaction is carried out to convert NiCl2 to Ni(P ?)3 with intermediate formation of Ni(P ?3)2Cl2. When NiCl2-6H2O is a starting material, essentially dry Ni(P?3)2Cl2 is formed in step (a)(i) by forming an admixture thereof with azeotrope-forming liquid (e.g., anhydrous C2-C5 alcohol or aprotic polar solvent or toluene) and heating to distill off water and forming essentially dry NiCl2 which is converted to essentially dry Ni(P?3)2Cl2 or the NiCl2- 6H2O is reacted with P?3 to form wet Ni(P?3)2Cl2 which is dried by forming an azeotropic mixture and distilling to remove water or by heating or the NiCl2?6H2O is made essentially dry by heating with or without P?3 present in the absence of reaction solvent to flash off water and form essentially dry NiCl2 which is reacted with P?3. The preferred C2-C5 alcohol is t-butanol which minimizes formation of hydrodehalogenation side-product in step (b) compared to other alcohols. The preferred aprotic polar solvent is acetonitrile.
Lin Henry C.
Maul James J.
Seper Karl W.
Lin Henry C.
Maul James J.
Occidental Chemical Corporation
Seper Karl W.
Swabey Ogilvy Renault
LandOfFree
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