CA1054971A
Expired / Lapsed
CA
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Photosensitized reactions utilizing polymer-bound photosensitizing catalysts
Assignee: Research Corp
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Filing: 1978-07-07
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Granted: 1979-05-22
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Expires: 1998-07-07
Abstract
Abstract ABSTRACT OF THE DISCLOSURE The present invention provides a method for the hetero-geneously catalyzed singlet oxygen photooxidation of a photo-oxidizable organic compound capable of adding oxygen by reaction with singlet oxygen, which comprises simultaneously subjecting said photooxidizable organic compound in an inert solvent to light irradiation and contact with molecular oxygen and a polymer-bound photosensitizing catalyst insoluble in the reaction medium, thereby introducing oxygen into the molecule of said photo-oxidizable organic compound by reaction with singlet oxygen generated from said molecular oxygen by energy transfer from said light irradiation and said polymer-bound photosensitizing catalyst, said polymer-bound photosensitizing catalyst comprising the nucleophilic displacement reaction product of (A) a polymeric material having attached thereto an available leaving group which is capable of being displaced in a nucleophilic displacement reaction with a nucleophilic reagent and (B) a photosensitizer dye containing in its molecule a nucliophilic which is capable of displacing said leaving group attached to said polymeric material in a nucleophilic displacement reaction.
Inventors
- 👤 Douglas C. Neckers
- 👤 Erich C. Blossey
- 👤 A. Paul Schaap
Bibliographic Details
Application Number
—
Jurisdiction
CA
Data Source
google_patents
Last Synchronized
2026-11-04 08:14
CPC Classifications
—
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
152 words
A method for the heterogeneously catalyzed singlet oxygen photooxidation of a photooxidizable organic compound capable of adding oxygen by reaction with singlet oxygen, which comprises simultaneously subjecting said photooxidizable organic compound in an inert solvent to light irradiation and contact with molecular oxygen and a polymer-bound photosensitizing catalyst insoluble in the reaction medium, thereby introducing oxygen into the molecule of said photooxidizable organic compound by reaction with singlet oxygen generated from said molecular oxygen by energy transfer from said light irradiation and said polymer-bound photosensitizing catalyst, said polymer-bound photosensitizing catalyst comprising the nucleophilic displacement reaction product of (A) a polymeric material having attached thereto an available leaving group which is capable of being displaced in a nucleophilic displacement reaction with a nucleo-philic reagent and (B) a photosensitizer dye containing in its molecule a nucleophile which is capable of displacing said leaving group attached to said polymeric material in a nucleophilic displacement reaction.
Claim 2
Independent Claim
152 words
A method for the heterogeneously catalyzed singlet oxygen photooxidation of a photooxidizable organic compound capable of adding oxygen by reaction with singlet oxygen, which comprises simultaneously subjecting said photooxidizable organic compound in an inert solvent to light irradiation and contact with molecular oxygen and a polymer-bound photosensitizing catalyst insoluble in the reaction medium, thereby introducing oxygen into the molecule of said photooxidizable organic compound by reaction with singlet oxygen generated from said molecular oxygen by energy transfer from said light irradiation and said polymer-bound photosensitizing catalyst, said polymer-bound photosensitizing catalyst comprising the nucleophilic displacement reaction product of (A) a polymeric material having attached thereto an available leaving group which is capable of being displaced in a nucleophilic displacement reaction with a nucleo-philic reagent and (B) a photosensitizer dye containing in its molecule a nucleophile which is capable of displacing said leaving group attached to said polymeric material in a nucleophilic displacement reaction.
Claim 3
Dependent Claim
22 words
The method of Claim 1, wherein said polymeric material is selected from the group consisting of chloromethyl-ated styrene polymers and polyvinylidene chloride.
Claim 4
Dependent Claim
13 words
The method of Claim 2, wherein said polymeric material is a chloromethylated polystyrene.
Claim 5
Dependent Claim
15 words
The method of Claim 2, wherein said polymeric material is a chloromethylated styrene divinylbenzene copolymer.
Claim 6
Dependent Claim
45 words
The method of Claim 1, wherein said photosensitizer dye is selected from the group consisting of rose bengal, acridine orange, chlorophyllin, crystal violet, eosin Y, fluorescein, flavin mononucleotide, hemtoporphyrin, hemin, malachite green, methylene blue, rhodamine B, chlorophyll, eosin, erythrosin, methylene green, toluidire blue and thionine.
Claim 7
Dependent Claim
12 words
The method of Claim 4, wherein said photosensitizer dye is rose bengal.
Claim 8
Dependent Claim
14 words
The method of Claim 1, wherein a mono-olefin is oxidized to an allylic hydroperoxide.
Claim 9
Dependent Claim
15 words
The method of Claim 1, wherein a conjugated diene is oxidized to a cyclic peroxide.
Claim 10
Dependent Claim
24 words
9, The method of Claim 1, wherein a heterocyclic olefin is oxidized by 1,2-cycloaddition to a 1,2-dioxetane which leaves thermally to a carbonyl-containing compound.
Claim 11
Independent Claim
88 words
A method for the heterogeneously catalyzed photo-dimerization of a photodimerizable organic compound selected from the group consisting of coumarin and indene which comprises simultaneously subjecting said photodimerizable organic compound to light irradiation and contact with a polymer-bound photo-sensitizing catalyst insoluble in the reaction medium, said polymer-bound photosensitizing catalyst comprising the nucleo-philic displacement reaction product of para-benzoyl acid and a polymeric material having attached thereto an available leaving group which is capable of being displaced in a nucleophilic displacement reaction with the carbonyl group of said para-benzoyl benzoic acid.
Claim 12
Independent Claim
88 words
A method for the heterogeneously catalyzed photo-dimerization of a photodimerizable organic compound selected from the group consisting of coumarin and indene which comprises simultaneously subjecting said photodimerizable organic compound to light irradiation and contact with a polymer-bound photo-sensitizing catalyst insoluble in the reaction medium, said polymer-bound photosensitizing catalyst comprising the nucleo-philic displacement reaction product of para-benzoyl acid and a polymeric material having attached thereto an available leaving group which is capable of being displaced in a nucleophilic displacement reaction with the carbonyl group of said para-benzoyl benzoic acid.
Claim 13
Dependent Claim
14 words
The method of Claim 10, wherein said polymeric material is a chloromethylated styrene polymer.
Claim 14
Dependent Claim
15 words
The method of Claim 11, wherein said chloromethyl-ated styrene polymer is a chloromethylated styrene-divinylbenzene copolymer.
Claim 15
Independent Claim
81 words
A method for the heterogeneously catalyzed photo-cycloaddition for tetrachlorethylene to cyclopentadiene which comprises simultaneously subjecting a mixture of tetrachloro-ethylene and cyclopentadiene to light irradiation and contact with a polymer-bound photosensitizing catalyst insoluble in the reaction medium, said polymer-bound photosensitizing catalyst comprising the nucleophilic displacement reaction product of para-benzoyl benzoic acid and a polymeric material having attached thereto an available leaving group which is capable of being displaced in a nucleophilic displacement reaction with the carbonyl group of said para-benzoyl benzoic acid.
Claim 16
Independent Claim
81 words
A method for the heterogeneously catalyzed photo-cycloaddition for tetrachlorethylene to cyclopentadiene which comprises simultaneously subjecting a mixture of tetrachloro-ethylene and cyclopentadiene to light irradiation and contact with a polymer-bound photosensitizing catalyst insoluble in the reaction medium, said polymer-bound photosensitizing catalyst comprising the nucleophilic displacement reaction product of para-benzoyl benzoic acid and a polymeric material having attached thereto an available leaving group which is capable of being displaced in a nucleophilic displacement reaction with the carbonyl group of said para-benzoyl benzoic acid.
Claim 17
Dependent Claim
14 words
The method of Claim 13, wherein said polymeric material is a chloromethylated styrene polymer.
Claim 18
Dependent Claim
15 words
The method of Claim 14, wherein said chloromethyl-ated styrene polymer is a chloromethylated styrene-divinylbenzene copolymer.
References Cited (Backward Citations)
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