US4082806A
Expired / Lapsed
US
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Preparation of tetraketones
Assignee: Wright State University
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Filing: 1975-12-18
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Granted: 1978-04-04
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Expires: 1995-12-18
Abstract
Abstract A method of preparing tetraketone precursors which are useful in the production of high temperature resistant polyquinoxaline resins. Suitable diketones are oxidized with a halogenating agent, such as cupric halide or hydrogen bromide, and dimethylsulfoxide to produce the corresponding tetraketone. The tetraketones which can be produced by the instant process have the formula: ##STR1## wherein R is hydrogen or an aryl, substituted aryl, heterocyclic or substituted heterocyclic radical and R' is an aryl, substituted aryl, arylalkyl, arylether, arylthioether, arylsulfoxide, arylsulfone, heterocyclic or substituted heterocyclic radical.
Inventors
- 👤 Frank W. Harris
- 👤 Bruce A. Reinhardt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 02:15
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/46; C07D213/50; C07C; C07C45/00; C07C45/27; C07C45/28; C07C45/30; C07C49/00; C07C49/76; C07C49/782; C07C49/784
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
94 words
The method of preparing a tetraketone having the formula ##STR8## wherein R' is selected from the group consisting of phenyl, diphenyl ether, diphenyl methane, pyridine, diphenyl sulfoxide, and xylene radicals and R is selected from the group consisting of phenyl, substituted phenyl, and pyridyl radicals from a diketone selected from the group consisting of 1,4-bis (phenylacetyl) benzene, 4,4'-bis(phenylacetyl) diphenyl ether, 1,3-diphenacylbenzene, 4,4'-bis(phenylacetyl)diphenylmethane, 2,6-diphenacylpyridine, 1,3-bis(2-pyridylacetyl) benzene, 4,4'-bis(phenylacetyl)diphenylsulfoxide, 1,3-bis(4-methylphenylacetyl)benzene, 1,4-bis(5-fluoro-2-nitrophenylacetyl)benzene, and α,α'-dibenzoyl-para-xylene, comprising oxidizing said diketone to said tetraketone with dimethylsulfoxide and a halogenating agent selected from the group consisting of cupric halide and hydrogen bromide.
Claim 2
Independent Claim
94 words
The method of preparing a tetraketone having the formula ##STR8## wherein R' is selected from the group consisting of phenyl, diphenyl ether, diphenyl methane, pyridine, diphenyl sulfoxide, and xylene radicals and R is selected from the group consisting of phenyl, substituted phenyl, and pyridyl radicals from a diketone selected from the group consisting of 1,4-bis (phenylacetyl) benzene, 4,4'-bis(phenylacetyl) diphenyl ether, 1,3-diphenacylbenzene, 4,4'-bis(phenylacetyl)diphenylmethane, 2,6-diphenacylpyridine, 1,3-bis(2-pyridylacetyl) benzene, 4,4'-bis(phenylacetyl)diphenylsulfoxide, 1,3-bis(4-methylphenylacetyl)benzene, 1,4-bis(5-fluoro-2-nitrophenylacetyl)benzene, and α,α'-dibenzoyl-para-xylene, comprising oxidizing said diketone to said tetraketone with dimethylsulfoxide and a halogenating agent selected from the group consisting of cupric halide and hydrogen bromide.
Claim 3
Dependent Claim
11 words
The method of claim 1 wherein an inert solvent is employed.
Claim 4
Dependent Claim
76 words
The method of claim 2 wherein said diketone is first contacted with a halogenating agent selected from the group consisting of cupric halide and hydrogen bromide in the presence of said inert solvent and reacted at 0° C to 150° C for between 1 and 24 hours to form a di(alpha-haloketone) reaction produce which is then treated with said dimethylsulfoxide at 0° C to 190° C for between 1 and 48 hours to form said tetraketone.
Claim 5
Dependent Claim
21 words
The method of claim 3 wherein said di(alphahaloketone) reaction product is isolated from said solvent prior to treatment with said dimethylsulfoxide.
Claim 6
Dependent Claim
12 words
The method of claim 3 wherein said halogenating agent is cupric bromide.
Claim 7
Dependent Claim
46 words
The method of claim 1 wherein a halogentating agent selected from the group consisting of cupric halide and hydrogen bromide and said dimethylsulfoxide are mixed together with said diketone and reacted at 0° to 150° C for between 1 and 48 hours to form said tetraketone.
Claim 8
Dependent Claim
11 words
The method of claim 1 wherein said diketone is 1,4-bis(phenylacetyl) benzene.
Claim 9
Dependent Claim
12 words
The method of claim 1 wherein said diketone is 4,4'-bis(phenylacetyl) diphenyl ether.
Claim 10
Dependent Claim
20 words
The method of claim 1 wherein said halogenating agent is cupric halide and cuprous halide is recovered as a by-product.
Claim 11
Dependent Claim
12 words
The method of claim 9 wherein said cupric halide is cupric bromide.
References Cited (Backward Citations)
US3839497A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-04-03 | 1981-10-03 | 1982-04-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-04-03 | 1985-10-03 | 1986-04-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-04-03 | 1989-10-03 | 1990-04-04 | $7700.00 | Window Closed / Lapsed |