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US4242285A
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Novel 2,6-dinitrophenyl selenium compounds and their use as epoxidation catalysts
Assignee: Dow Chemical Co
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Filing: 1979-03-16
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Granted: 1980-12-30
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Expires: 1999-03-16
Abstract
Abstract Novel unsubstituted and 4-substituted, 2,6-dinitrophenyl seleninic acids, selenium halides and diselenides are described. The above-described selenium compounds are particularly useful to catalyze the oxidation of olefins to the corresponding epoxide in the presence of hydrogen peroxide.
Inventors
- 👤 James M. Renga
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:02
CPC Classifications
C; C07; C07C; C07C391/00; C07C391/02; C07D; C07D301/00; C07D301/02; C07D301/03; C07D301/12
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
44 words
A 2,6-dinitrophenyl selenium compound corresponding to the formula I or II ##STR3## wherein in each of the above formulas, X is selected from the group consisting of hydrogen, trifluoromethyl, trichloromethyl, nitro, chloro and bromo moieties; and in Formula II, Y is bromine or chlorine.
Claim 2
Dependent Claim
44 words
A 2,6-dinitrophenyl selenium compound corresponding to the formula I or II ##STR3## wherein in each of the above formulas, X is selected from the group consisting of hydrogen, trifluoromethyl, trichloromethyl, nitro, chloro and bromo moieties; and in Formula II, Y is bromine or chlorine.
Claim 3
Dependent Claim
16 words
The selenium compound as described in claim 1 wherein X is hydrogen or a nitro moiety.
Claim 4
Dependent Claim
15 words
The selenium compound as described in claim 2 wherein the compound corresponds to formula I.
Claim 5
Dependent Claim
63 words
A process for preparing epoxides from olefins comprising admixing an olefin bearing at least one alkyl, aryl or oxyalkyl substituent in an α-position to an olefinic carbon with hydrogen peroxide in a liquid reaction medium in the presence of an effective amount of an epoxidation catalyst prepared by introducing at least one of the compounds described in claim 1 to the reaction medium.
Claim 6
Dependent Claim
35 words
The process as described in claim 4 wherein the reaction medium comprises two phases, the olefin being present in a water-immiscible organic solvent phase and the hydrogen peroxide being present in a separate aqueous phase.
Claim 7
Dependent Claim
28 words
The process as described in claim 5 wherein the organic solvent is selected from the group consisting of chlorinated alkanes, aromatic carbocyclic compounds, heterocyclic compounds and epoxidizable olefins.
Claim 8
Dependent Claim
28 words
The process as described in claim 5 wherein about 0.1 to about 2 equivalents of hydrogen peroxide per equivalent of olefin are present in the biphasic reaction medium.
Claim 9
Dependent Claim
30 words
The process as described in claim 7 wherein the aqueous phase consists of about 30 to greater than 90 weight percent hydrogen peroxide at the beginning of the epoxidation reaction.
Claim 10
Dependent Claim
26 words
The process as described in claim 5 or 8 wherein the olefin is propylene, butene-1, butene-2, isobutylene, pentene-1, hexene-1, pentene-2, octene-1, cyclopentene, cyclohexene, cyclooctene or 1,2-diphenylethylene.
Claim 11
Dependent Claim
16 words
The selenium compound as described in claim 1 wherein Y is bromine and X is hydrogen.
Claim 12
Dependent Claim
12 words
The selenium compound as described in claim 3 wherein X is hydrogen.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-12-30 | 1984-06-30 | 1984-12-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-30 | 1988-06-30 | 1988-12-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-30 | 1992-06-30 | 1992-12-30 | $7700.00 | Window Closed / Lapsed |