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Use of metal complexes of tripodal ligands as oxidation catalysts

IP.com Disclosure Number: IPCOM000127745D
Publication Date: 2005-Sep-13
Document File: 8 page(s) / 103K

Publishing Venue

The IP.com Prior Art Database

Abstract

Disclosed is the use of metal complexes of tripodal ligands, especially N,N',N''-tris[salicylideneaminoethyl]amine, as oxidation catalysts for a variety of organic reactions.

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Use of metal complexes of tripodal ligands as oxidation catalysts

The majority of bulk organic products contain oxygen functionalities. Many of these are produced in chemical and petrochemical industries by direct oxy-functionalization of hydrogen feedstock. For this purpose oxidation catalysts in heterogeneous and homogenous reactions are widely applied: epoxides, alcohols, ketones, carboxylic acids, the direct oxidation products of saturated or unsaturated hydrocarbons, may be transformed into a variety of valuable oxygen functionalized derivates, which are important building blocks in organic synthesis. Unquestionably, the selective and catalytic oxidation of organic substrates is an important process of huge interest.

It is known that some manganese complexes, especially those of the salen type, are useful catalysts for oxidations with peroxygen compounds, especially as part of a washing process. It is also known that certain other manganese complexes have a marked bleaching effect on dirt and dyes in wash liquors. There is nevertheless a demand for further compounds having an improved effect and/or having a broader application range.

It has now been found that certain metal complexes of tripodal ligands, obtainable by reacting tris(2-aminoethyl)amine with aldehydes or ketones, substantially meet the stated requirements, when used as catalysts. They enhance the action of oxidizing agents in a wide variety of applications to a high degree.

This publication describes the oxidation catalyst uses of metal complexes containing a tripodal ligand of the formula

N

    R1 R2

R3

R4

R1''

R2''

R3''

R4''

OH

 O H

R9''

N

N

(1)

where R1, R2, R3, R4, R1', R2', R3', R4', R1", R2", R3" and R4" are each independently hydrogen, cyano, halogen, SO3M, where M is hydrogen, an alkali metal cation, an alkaline earth metal cation, ammonium or an organic ammonium cation, SO2NH2, SO2NHR5, SO2N(R5)2, OR5 or COOR5, where R5 is hydrogen or linear or branched C1-C4alkyl, nitro, linear or branched C1-C8alkyl, linear or branched fluorinated or perfluorinated C1- C8alkyl, NHR6 , NR6R7, NR6R7R10 or linear or branched C1-C8alkyl-R8, where R8 is OR5, COOR5, NH2, NHR6, NR6R7 or NR6R7R10, where R6, R7 and R10 are identical or different and each is linear or branched C1-C12alkyl or where R6 and R7 combine with the joining nitrogen atom to form a 5-, 6- or 7-membered ring, which may contain

R3'

R2'

R1'

R4'

N

OH

R9'

R9

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further heteroatoms, and where R9, R9' and R9" are each independently hydrogen, linear or branched C1-C8alkyl or aryl, as catalysts for oxidations.

Particular preference is given to the use of Mn(III) and Fe(III) complexes containing a ligand of the above formula (1), especially an Mn(III) and Fe(III) complex which contains a ligand of the above formula (1) and metal in a molar ratio of 1:1.

Halogen is preferably chlorine, bromine or fluorine, particularly preferably chlorine.

Alk...