Patent US3979450A successfully refreshed from Google Patents.
US3979450A
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US
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Method for preparing dicarboxylic acids
Assignee: Individual
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Filing: 1973-02-08
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Granted: 1976-09-07
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Expires: 1993-02-08
Abstract
Abstract A method for preparing dicarboxylic acids by subjecting cycloolefins to ozonolysis in a medium of lower monocarboxylic acids so as to form an ozonalyzate; treating the ozonalyzate with a solution of hydrogen peroxide; passing the thus obtained mixture through a solid acid catalyst, such as an Amberlite IR-120 cation-exchange resin; and subjecting the thus obtained catalyzed product first to thermal treatment at a temperature of from 50° to 80°C and then to thermal decomposition at a temperature of from 90° to 110°C to form desired dicarboxylic acids such as succinic, suberic or 1,10-decanedicarboxy acids, depending on the starting cycloolefin, in a yield 98 per cent of the theoretical value and of 99.5 per cent purity.
Inventors
- 👤 Jury Leonidovich Moskovich
- 👤 Jury Nikolaevich Juriev
- 👤 Viktor Karlovich Tsyskovsky
- 👤 Ljudmila Vasilievna Berezova
- 👤 Nokhum Davidovich Gilchenok
- 👤 Vladimir Avgustovich Yanshevsky
- 👤 Dmitry Vasilievich Mushenko
- 👤 Evgeny Semenovich Zelikman
- 👤 Rufina Alexandrovna Filippova
- 👤 Vladimir Leonidovich Klimenko
- 👤 Valerian Mikhailovich Sobolev
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:42
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/34; C07C51/16; C07C51/285
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
152 words
A method for preparing dicarboxylic acids, comprising ozonolyzing a cycloolefin reactant with ozonized air in a lower alkanoic acid medium at a temperature of from 20° to 40°C to form an ozonolyzate; treating the ozonolyzate with an aqueous solution of hydrogen peroxide having a concentration of from 20 to 30 percent of said hydrogen peroxide; passing the obtained mixture through a solid acid catalyst which is a cation exchange resin having a polystyrene matrix cross-linked wih divinylbenzene and containing sulfonic acid groups, said cation exchange resin being in the H-form at a temperature of from 30° to 60°C at a space velocity of from 2 to 4 hours - 1 ; heat-treating the cartalyzed product to a temperature of from 50° to 80°C and at a space velocity of from 0.3 to 0.5 hour - 1 ; and thermally degrading the heat-treated catalyzed product at a temperature of from 90° to 110°C.
Claim 2
Independent Claim
152 words
A method for preparing dicarboxylic acids, comprising ozonolyzing a cycloolefin reactant with ozonized air in a lower alkanoic acid medium at a temperature of from 20° to 40°C to form an ozonolyzate; treating the ozonolyzate with an aqueous solution of hydrogen peroxide having a concentration of from 20 to 30 percent of said hydrogen peroxide; passing the obtained mixture through a solid acid catalyst which is a cation exchange resin having a polystyrene matrix cross-linked wih divinylbenzene and containing sulfonic acid groups, said cation exchange resin being in the H-form at a temperature of from 30° to 60°C at a space velocity of from 2 to 4 hours - 1 ; heat-treating the cartalyzed product to a temperature of from 50° to 80°C and at a space velocity of from 0.3 to 0.5 hour - 1 ; and thermally degrading the heat-treated catalyzed product at a temperature of from 90° to 110°C.
Claim 3
Dependent Claim
13 words
A method as claimed in claim 1, wherein the cycloolefin reactant is cyclododecatriene.
Claim 4
Dependent Claim
13 words
A method as claimed in claim 1, wherein the cycloolefin rectant is cyclododecene.
Claim 5
Dependent Claim
13 words
A method as claimed in claim 1, wherein the cycloolefin reactant is cyclooctadiene.
Claim 6
Dependent Claim
13 words
A method as claimed in claim 1, wherein the cycloolefin reactant is cyclooctene.
Claim 7
Dependent Claim
21 words
A method as claimed in claim 1, wherein the ozonolyzate is treated with a 29-30 percent aqueous solution of hydrogen peroxide.
Claim 8
Dependent Claim
17 words
A method as claimed in claim 1, wherein said lower alkanoic acid is 99.2-99.6 percent acetic acid.
Claim 9
Dependent Claim
31 words
A method as claimed in claim 1, wherein the ozonolyzate is passed through a solid acid catalyst at a volumetric rate of 4 hour - 1 at a temperature of 50°C.
Claim 10
Dependent Claim
27 words
A method as claimed in claim 1, wherein the catalyzed product is thermally treated at a rate of 0.5 hour - 1 at a temperature of 80°C.
Claim 11
Dependent Claim
29 words
A method as claimed in claim 1, wherein said catalyst is a cation-exchange resin having a polystyrene matrix cross-linked with approximately 8% of divinylbenzene and containing sulfonic acid groups.
Claim 12
Independent Claim
135 words
A method for preparing dicarboxylic acids, comprising ozonolyzing a cycloolefin reactant with ozonized air in a lower alkanoic acid medium at a temperature of from 20° to 40°C to form an ozonolyzate; treating the ozonolyzate with an aqueous solution of hydrogen peroxide having a concentration of from 20 to 30 percent of said hydrogen peroxide; passing the obtained mixture through a solid acid catalyst consisting of phosphoric acid supported on a silica gel at a temperature of from 30° to 60°C at a space velocity of from 2 to 4 hours - 1 ; heat-treating the catalyzed product to a temperature of from 50° to 80°C and at a space velocity of from 0.3 to 0.5 hour - 1 ; and thermally degrading the heat-treated catalyzed product at a temperature of from 90°C to 110°C.
Claim 13
Independent Claim
135 words
A method for preparing dicarboxylic acids, comprising ozonolyzing a cycloolefin reactant with ozonized air in a lower alkanoic acid medium at a temperature of from 20° to 40°C to form an ozonolyzate; treating the ozonolyzate with an aqueous solution of hydrogen peroxide having a concentration of from 20 to 30 percent of said hydrogen peroxide; passing the obtained mixture through a solid acid catalyst consisting of phosphoric acid supported on a silica gel at a temperature of from 30° to 60°C at a space velocity of from 2 to 4 hours - 1 ; heat-treating the catalyzed product to a temperature of from 50° to 80°C and at a space velocity of from 0.3 to 0.5 hour - 1 ; and thermally degrading the heat-treated catalyzed product at a temperature of from 90°C to 110°C.
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) | 1979-09-07 | 1980-03-08 | 1980-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-07 | 1984-03-08 | 1984-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-07 | 1988-03-08 | 1988-09-07 | $7700.00 | Window Closed / Lapsed |