Method for the catalytic epoxidation of olefins with hydrogen peroxide
First Claim
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1. A method for the catalytic epoxidation of olefins with hydrogen peroxide, comprising reacting an olefin in a homogeneous phase or in a two-phase system with a source of hydrogen peroxide in the presence ofrhenium-oxo-complexes ora binuclear compound of the type μ
- -oxobis [porphyrinatooxorhenium (V)]withoctaethyl porphyrin or5,10,15,20-tetraphenyl porphyrin or5,10,15,20-tetra(4-pyridyl)-porphyrinas ligands in which hydrogen atoms or free electron pairs are optionally substituted once or several times on the phenyl groups or pyridyl groups by halogen, hydroxy, carboxy, cyano, rhodano, nitro, C1 -C6 -alkyl, trihalogen methyl, C1 -C6 -alkoxy, C1 -C6 -alkane sulfonyloxy, aminocarbonyl, aminocarbonyl containing one or two C1 -C6 -alkyl groups, C1 -C6 -alkyl carbonyl, amino, di-C1 -C6 -alkyl amino, C1 -C6 -alkanoyl amino, C1 -C6 -alkyl-C1 -C6 -alkanoyl amino, C1 -C6 -alkane sulfonyl amino, C1 -C6 -alkyl-C1 -C6 -alkane sulfonyl amino, aminosulfonyl, aminosulfonyl containing one or two C1 -C6 -alkyl groups, C1 -C6 -alkoxysulfonyl (--SO2 --O--C1 --C6 -alkyl) sulfo or C1 -C6 -alkane sulfonyl and two of these groups can also be the methylene dioxy group, in which instance the complex in the case of the rhenium-oxo-complexes optionally carries an anion of the series F--, Cl--, Br--, I--, CH3 O--, C2 H5 O--, C3 H7 O--, t--C4 H9 O--, C6 H5 O--, HO--, AcO--, SCN--, OCN--, ClO4 -- on the central atom.
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Abstract
A method for the catalytic epoxidation of olefins with hydrogen peroxide in the presence of rhenium-oxo-complexes or of a binuclear compound of the type μ-oxobis [porphyrinato-oxo-rhenium(V)] with octaethyl porphyrin or 5,10,15,20-tetraphenyl porphyrin or 5,10,15,20-tetra(4-pyridyl)-porphyrin as ligands.
27 Citations
13 Claims
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1. A method for the catalytic epoxidation of olefins with hydrogen peroxide, comprising reacting an olefin in a homogeneous phase or in a two-phase system with a source of hydrogen peroxide in the presence of
rhenium-oxo-complexes or a binuclear compound of the type μ - -oxobis [porphyrinatooxorhenium (V)]with
octaethyl porphyrin or 5,10,15,20-tetraphenyl porphyrin or 5,10,15,20-tetra(4-pyridyl)-porphyrin as ligands in which hydrogen atoms or free electron pairs are optionally substituted once or several times on the phenyl groups or pyridyl groups by halogen, hydroxy, carboxy, cyano, rhodano, nitro, C1 -C6 -alkyl, trihalogen methyl, C1 -C6 -alkoxy, C1 -C6 -alkane sulfonyloxy, aminocarbonyl, aminocarbonyl containing one or two C1 -C6 -alkyl groups, C1 -C6 -alkyl carbonyl, amino, di-C1 -C6 -alkyl amino, C1 -C6 -alkanoyl amino, C1 -C6 -alkyl-C1 -C6 -alkanoyl amino, C1 -C6 -alkane sulfonyl amino, C1 -C6 -alkyl-C1 -C6 -alkane sulfonyl amino, aminosulfonyl, aminosulfonyl containing one or two C1 -C6 -alkyl groups, C1 -C6 -alkoxysulfonyl (--SO2 --O--C1 --C6 -alkyl) sulfo or C1 -C6 -alkane sulfonyl and two of these groups can also be the methylene dioxy group, in which instance the complex in the case of the rhenium-oxo-complexes optionally carries an anion of the series F--, Cl--, Br--, I--, CH3 O--, C2 H5 O--, C3 H7 O--, t--C4 H9 O--, C6 H5 O--, HO--, AcO--, SCN--, OCN--, ClO4 -- on the central atom. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13)
- -oxobis [porphyrinatooxorhenium (V)]with
Specification
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Current AssigneeDegussa AG (Rag-Stiftung)
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Original AssigneeDegussa AG (Rag-Stiftung)
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InventorsSchmidt, Manfred, Buchler, Johann, Prescher, Guenter
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Primary Examiner(s)Hollrah, Glennon H.
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Assistant Examiner(s)Trinh, Ba K.
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Application NumberUS07/247,300Time in Patent Office797 DaysField of Search549/531, 540/145US Class Current549/531CPC Class CodesC07D 301/12 with hydrogen peroxide or i...C07D 303/04 containing only hydrogen an...
