US5086189A
Expired / Lapsed
US
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Process for the manufacture of epoxides
Assignee: Solvay Chimie SA
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Filing: 1990-02-02
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Granted: 1992-02-04
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Expires: 2010-02-02
Abstract
Abstract Epoxides are manufactured by reacting olefines, such as cyclohexene, isoamylene, alpha-pinene, allyl alcohol, 2,5-dihydrofuran and styrene, with hydrogen peroxide, in a homogeneous liquid reaction mixture containing less than 10% by weight of water, in the presence of a compound of a metal of group 6a, such as selenium dioxide or selenous acid, and of an organic nitrogen-containing base having a pKa of not more than 8, such as pyridine, chloropyridine, collidine, quinoline, isoquinoline or a lutidine.
Inventors
- 👤 Andre Lecloux
- 👤 Claude Declerck
- 👤 Franz Legrand
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:42
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/04; C07D301/00; C07D301/02; C07D301/03; C07D301/12; C07D303/00; C07D303/02; C07D303/04
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
80 words
A process for the manufacture of epoxides, comprising: reacting hydrogen peroxide with a compound containing an ethylenic double bond, in a homogenous liquid reaction mixture in which the concentration of water is kept below 10% by weight, containing a catalyst consisting essentially of a compound selected from the group consisting of selenium dioxide and selenous acid, and a base which is a member of the group consisting of pyridine, halogeno-substituted pyridine, amino-substituted pyridine, alkoxy-substituted pyridine, alkyl-substituted pyridine, quinoline, and isoquinoline.
Claim 2
Dependent Claim
80 words
A process for the manufacture of epoxides, comprising: reacting hydrogen peroxide with a compound containing an ethylenic double bond, in a homogenous liquid reaction mixture in which the concentration of water is kept below 10% by weight, containing a catalyst consisting essentially of a compound selected from the group consisting of selenium dioxide and selenous acid, and a base which is a member of the group consisting of pyridine, halogeno-substituted pyridine, amino-substituted pyridine, alkoxy-substituted pyridine, alkyl-substituted pyridine, quinoline, and isoquinoline.
Claim 3
Dependent Claim
11 words
Process according to claim 1, wherein the catalyst is selenium dioxide.
Claim 4
Dependent Claim
11 words
Process according to claim 1, wherein the catalyst is selenous acid.
Claim 5
Dependent Claim
23 words
Process according to claim 1, wherein the catalyst is used in amounts of between 0.05 and 25 g per liter of reaction mixture.
Claim 6
Dependent Claim
36 words
Process according to claim 1, wherein the base is chosen from amongst pyridine, chloropyridine, quinoline, isoquinoline and their derivatives substituted by one or more alkyl groups containing from 1 to 2 carbon atoms per alkyl group.
Claim 7
Dependent Claim
26 words
Process according to claim 1, wherein the base is used in amounts of between 0.1 and 10 mols per gram atom of metal in the catalyst.
Claim 8
Dependent Claim
38 words
Process according to claim 1, wherein the compound containing an ethylenic double bond is chosen from amongst acyclic or cyclic olefines containing from 2 to 20 carbon atoms and not containing more than 6 carbon atoms per ring.
Claim 9
Dependent Claim
34 words
Process according to claim 1, wherein the reaction is carried out in the presence of an inert organic solvent chosen from amongst primary, secondary or tertiary alcohols containing from 3 to 8 carbon atoms.
Claim 10
Dependent Claim
33 words
Process according to claim 1, wherein the compound containing the ethylenic double bond is an olefin, and the molar ratio of olefin to hydrogen peroxide is at least 0.9 and less than 10.
Claim 11
Dependent Claim
30 words
Process according to claim 1, wherein the compound containing the ethylenic double bond is an acyclic olefin or a cyclic olefin containing no more than 6 carbon atoms per ring.
Claim 12
Dependent Claim
21 words
Process according to claim 1, wherein the concentration of water in the reaction mixture is kept below 5 percent by weight.
Claim 13
Dependent Claim
21 words
Process according to claim 1, wherein the concentration of water in the reaction mixture is kept below 2 percent by weight.
Claim 14
Dependent Claim
21 words
Process according to claim 1, wherein the concentration of water in the reaction mixture is kept below 1 percent by weight.
Claim 15
Dependent Claim
13 words
Process according to claim 1, wherein the base employed is quinoline or pyridine.
Claim 16
Dependent Claim
15 words
Process according to claim 1, wherein the base has a pKa between 2.5 and 7.5.
Claim 17
Dependent Claim
67 words
Process according to claim 1, wherein the concentration of water in the reaction mixture is less than 5% by weight, the base is quinoline or pyridine, the catalyst is selenium oxide, and the hydrogen peroxide is introduced into the reaction mixture over a period of 10 minutes and the reaction of hydrogen peroxide with a compound containing an ethylenic double bond proceeds for a further 10 minutes.
Claim 18
Dependent Claim
21 words
Process according to claim 1, wherein the amino-substituted pyridine is a member of the group consisting of 2-aminopyridine, 3-aminopyridine, and 2,5-diaminopyridine.
Claim 19
Dependent Claim
20 words
Process according to claim 1, wherein the alkoxy-substituted pyridine is a member of the group consisting of 3-methyoxypyridine, and 4-methoxypyridine.
Claim 20
Dependent Claim
23 words
Process according to claim 1, wherein the alkyl-substituted pyridine is a member of the group consisting of picolines, lutidines, collidines, ethylpyridines, and propylpyridines.
Claim 21
Dependent Claim
36 words
Process according to claim 2, wherein the base is chosen from amongst pyridine, chloropyridine, quinoline, isoquinoline and their derivatives substituted by one or more alkyl groups containing from 1 to 2 carbon atoms per alkyl group.
Claim 22
Dependent Claim
22 words
Process according to claim 9 wherein the olefin is used in amounts between 1.5 and 5 mols per mol of hydrogen peroxide.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-02-03 | 1995-08-05 | 1996-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-02-03 | 1999-08-05 | 2000-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-02-03 | 2003-08-05 | 2004-02-04 | $7700.00 | Window Closed / Lapsed |