US4247641A
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US
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Method for producing epoxides and glycols from alkenes
Assignee: Novartis Vaccines and Diagnostics Inc
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Filing: 1979-05-29
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Granted: 1981-01-27
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Expires: 1999-05-29
Abstract
Abstract A method is described for the manufacture of epoxides or glycols from olefins. An olefin is contacted with a reaction mixture of a halogenating enzyme, an oxydizing agent and a halide ion source, for a sufficient period to convert the olefin to a halohydrin. The halohydrin is then converted to an epoxide or glycol.
Inventors
- 👤 Saul L. Neidleman
- 👤 William F. Amon, Jr.
- 👤 John Geigert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 00:20
CPC Classifications
C; C12; C12N; C12N9/00; C12N9/0004; C12N9/0071; C07; C07C; C07C29/00; C07C29/09; C07C29/10; C07D; C07D301/00; C07D301/02; C12N9/0065; C12P; C12P17/00; C12P17/02; C12P7/00; C12P7/02; C12P7/04
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
71 words
A method for the manufacture of epoxides or glycols from olefins comprising, providing a reaction mixture of a halogenating enzyme, an oxidizing agent and a halide ion source in a reaction vessel, introducing an olefin into said reaction vessel and maintaining said olefin in contact with said reaction mixture for a sufficient period of time to convert said olefin to a halohydrin, and converting said halohydrin to an epoxide or glycol.
Claim 2
Independent Claim
71 words
A method for the manufacture of epoxides or glycols from olefins comprising, providing a reaction mixture of a halogenating enzyme, an oxidizing agent and a halide ion source in a reaction vessel, introducing an olefin into said reaction vessel and maintaining said olefin in contact with said reaction mixture for a sufficient period of time to convert said olefin to a halohydrin, and converting said halohydrin to an epoxide or glycol.
Claim 3
Dependent Claim
34 words
A method in accordance with claim 1 wherein said halogenating enzyme is a perioxidase derived from a member selected from the group consisting of the micoroorganism Caldariomyces fumago, seaweed, milk, thyroid, leukocytes and horseradish.
Claim 4
Dependent Claim
31 words
A method in accordance with claim 1 wherein said halogenating enzyme is a peroxidase derived from a member selected from the group consisting of the microorganism Caldariomyces fumago, seaweed and milk.
Claim 5
Dependent Claim
14 words
A method in accordance with claim 1 wherein said oxidizing agent is hydrogen peroxide.
Claim 6
Dependent Claim
18 words
A method in accordance with claim 1 wherein said halide ion source is a water soluble halide salt.
Claim 7
Dependent Claim
23 words
A method in accordance with claim 1 wherein the reaction is conducted with the pH range of from about 2.2 to about 8.0.
Claim 8
Dependent Claim
32 words
A method in accordance with claim 4 wherein said hydrogen peroxide is present during said reaction at a molar ratio of from about 0.5:1 to about 50:1 with respect to said olefin.
Claim 9
Dependent Claim
15 words
A method in accordance with claim 4 wherein said hydrogen peroxide is generated in situ.
Claim 10
Dependent Claim
48 words
A method according to claim 1 wherein said oxidizing agent is hydrogen peroxide generated in situ by means of glucose-2-oxidase on a glucose substrate with co-production of D-arabino-2-hexosulose, and wherein the D-arabino-2-hexosulose is converted to D-fructose to provide the latter as a by-product to the epoxide or glycol.
Claim 11
Dependent Claim
29 words
A method according to claim 1 wherein said oxidizing agent is hydrogen peroxide generated in situ by means of methanol oxidase on a methanol substrate with co-production of formaldehyde.
Claim 12
Dependent Claim
30 words
A method according to claim 1 wherein said oxidizing agent is hydrogen peroxide generated in situ by means of glucose oxidase on a glucose substrate with co-production of gluconic acid.
Claim 13
Dependent Claim
72 words
A method in accordance with claim 1 wherein said halogenating enzyme is derived from a member selected from the group consisting of the microorganism Caldariomyces fumago, lactoperoxidase, and seaweed, said oxidizing agent is hydrogen peroxide, said halide ion source is selected from the group consisting of the chloride, bromide and iodide salts of sodium and potassium, and said reaction takes place in an aqueous environment at ambient conditions of temperature and pressure.
Claim 14
Dependent Claim
21 words
A method in accordance with claim 1 wherein said halohydrin is converted to an epoxide by reaction with aqueous slaked lime.
Claim 15
Dependent Claim
17 words
A method in accordance with claim 12 wherein said epoxide is converted by hydration to a glycol.
Claim 16
Dependent Claim
22 words
A method in accordance with claim 1 wherein said halohydrin is converted to an epoxide enzymatically by means of a halohydrin epoxidase.
Claim 17
Dependent Claim
37 words
A method in accordance with claim 15 wherein said halohydrin epoxidase is produced by an organism selected from the group consisting of a bacterium of the species Flavobacterium, the fungus Caldariomyces fumago, and the seaweed Laurencia pacifica.
Claim 18
Dependent Claim
26 words
A method in accordance with claim 15 wherein said halohydrin is enzymatically converted to an epoxide in the same reactor in which said halohydrin is formed.
Claim 19
Dependent Claim
60 words
A method in accordance with claim 15 wherein said halogenating enzyme is immobilized by attachment to a carrier in a first zone of said reaction vessel, said epoxidase is immobilized by attachment to a carrier in a second zone in said reaction vessel, and said olefin is passed continuously through said reaction vessel to continuously provide an olefin epoxide product.
Claim 20
Dependent Claim
92 words
A method in accordance with claim 15 wherein said halogenating enzyme is immobilized by attachment to a carrier in a first zone of said reaction vessel, said epoxidase is immobilized by attachment to a carrier in a second zone in said reaction vessel, wherein said oxidizing agent is hydrogen peroxide generated in situ by use of an enzyme which is immobilized by attachment to a carrier in said first zone of said reaction vessel, and wherein said olefin is passed continuously through said reaction vessel to continuously provide an olefin epoxide product.
Claim 21
Dependent Claim
33 words
A method in accordance with claim 1 wherein said olefin is selected from the group consisting of: ethylene, propylene, butene-1, pentene-1, octene-1, decene-1, dodecene-1, isobutylene, cis-butene-2, transbutene-2, 2-methyl-butene-2, 1,3-butadiene, 1,4-pentadiene, isoprene, and 1,7-octadiene.
Claim 22
Dependent Claim
26 words
A method in accordance with claim 1 wherein said olefin is selected from the group consisting of: styrene, allyl alcohol, allyl chloride, allyl bromide, and allene.
Claim 23
Dependent Claim
34 words
A method in accordance with claim 1 wherein said hydrogen peroxide is generated in situ by means of an enzyme, and wherein said halohydrin is converted to an epoxide by means of an enzyme.
Claim 24
Dependent Claim
86 words
In a method for the manufacture of epoxides or glycols from olefins wherein an intermediate halohydrin is provided which is converted to an epoxide or glycol, the step of producing the halohydrin from the olefin comprising, providing a reaction mixture of a halogenating enzyme, an oxidizing agent and a halide ion source in a reaction vessel, and introducing an olefin into said reaction vessel and maintaining said olefin in contact with said reaction mixture a sufficient period of time to convert said olefin to a halohydrin.
Claim 25
Dependent Claim
86 words
In a method for the manufacture of epoxides or glycols from olefins wherein an intermediate halohydrin is provided which is converted to an epoxide or glycol, the step of producing the halohydrin from the olefin comprising, providing a reaction mixture of a halogenating enzyme, an oxidizing agent and a halide ion source in a reaction vessel, and introducing an olefin into said reaction vessel and maintaining said olefin in contact with said reaction mixture a sufficient period of time to convert said olefin to a halohydrin.
Claim 26
Dependent Claim
34 words
A method in accordance with claim 23 wherein said halogenating enzyme is a peroxidase derived from a member selected from the group consisting of the microorganism Caldariomyces fumago, seaweed, milk, thyroid, leukocytes, and horseradish.
Claim 27
Dependent Claim
31 words
A method in accordance with claim 24 wherein said halogenating enzyme is a peroxidase derived from a member selected from the group consisting of the microorganism Caldariomyces fumago, seaweed and milk.
Claim 28
Dependent Claim
14 words
A method in accordance with claim 25 wherein said oxidizing agent is hydrogen peroxide.
Claim 29
Dependent Claim
18 words
A method in accordance with claim 25 wherein said halide ion source is a water soluble halide salt.
Claim 30
Dependent Claim
47 words
A method according to claim 25 wherein said hydrogen perioxide is generated in situ by means of an enzyme at a rate such that the hydrogen peroxide is present during said reaction at a molar ratio which is about 1:1 or less with respect to said olefin.
Claim 31
Dependent Claim
36 words
A method according to claim 25 wherein said oxidizing agent is hydrogen peroxide generated in situ by means of glucose-2-oxidase on a glucose substrate with co-production of D-arabino-2-hexosulose, and wherein the D-arabino-2-hexosulose is converted to D-fructose.
Claim 32
Dependent Claim
85 words
In a method for the manufacture of epoxides or glycols from olefins by producing an intermediate halohydrin from the olefin by reaction with a halogenating enzyme, an oxidizing agent and a halide ion source, and by conversion of the halohydrin to an epoxide or glycol, the steps of generating hydrogen peroxide as the oxidizing agent in situ by reaction of glucose-2-oxidase on a glucose substrate to produce D-arabino-2-hexosulose as a co-product, and converting the D-arabino-2-hexosulose to D-fructose as a co-product to the epoxide or glycol.
Claim 33
Dependent Claim
85 words
In a method for the manufacture of epoxides or glycols from olefins by producing an intermediate halohydrin from the olefin by reaction with a halogenating enzyme, an oxidizing agent and a halide ion source, and by conversion of the halohydrin to an epoxide or glycol, the steps of generating hydrogen peroxide as the oxidizing agent in situ by reaction of glucose-2-oxidase on a glucose substrate to produce D-arabino-2-hexosulose as a co-product, and converting the D-arabino-2-hexosulose to D-fructose as a co-product to the epoxide or glycol.
Claim 34
Dependent Claim
17 words
A method in accordance with claim 30 wherein the D-arabino-2-hexosulose is converted to D-fructose by chemical hydrogenation.
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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) | 1984-01-27 | 1984-07-28 | 1985-01-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-27 | 1988-07-28 | 1989-01-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-27 | 1992-07-28 | 1993-01-27 | $7700.00 | Window Closed / Lapsed |