C - Chemistry – Metallurgy – 09 – B
Patent
C - Chemistry, Metallurgy
09
B
C09B 47/04 (2006.01) C09B 47/24 (2006.01)
Patent
CA 2130853
Disclosed herein is a selective process for the preparation of single positional isomers of monosulphonated metallo derivatives of compounds selected from the group consisting of monosulphophthalocyanines of the following general formula: Image and Image wherein M is Zn (II), AL(III), Ga(III), Sn(IV); and R is SO3Na, SO2Cl and SO2NHR; monosulphonaphthobenzoporphyrazines of the following general formula: Image and Image wherein M and R are as defined above; and monosulphotetraphenylporphyrins of the following general formula: Image wherein M is HH or Zn(II) and R is 2-, 3- or 4-SO3Na, SO2Cl and SO2NHR; and salts or sulphonamides thereof, the method comprising the steps of: (a) obtaining a basic macrocycle by condensation of benzaldehyde and appropriate nitrobenzaldehyde with pyrrole; (b) converting the basic macrocycle to a monodiazonium salt by reducing the nitro group to an amine group followed by diazotization; (c) sulphonating the basic macrocycle by mixing a solution containing sulphur dioxide and a cupric ion catalyst to a suspension or solution of the monodiazonium salt to cause a reaction yielding a mixture of compounds including monosulphonated and monochlorinated derivates; (d) hydrolysing the mixture; (e) recovering from the hydrolysed mixture the single isomeric monosulphonated compound, wherein the method introduces the sulphonate substituents as the final step in the reaction sequence.
Ali Hasrat
Kudrevich Svetlana
Van Lier Johannes E.
Goudreau Gage Dubuc
Universite de Sherbrooke
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