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US4143045A
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Method of preparing dibenzothiazolyl disulfides
Assignee: Goodyear Tire and Rubber Co
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Filing: 1977-11-17
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Granted: 1979-03-06
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Expires: 1997-11-17
Abstract
Abstract Method of preparing dibenzothiazolyl disulfides by oxidizing mercaptobenzothiazole in a substantially neutral saturated aliphatic alcohol solution with a hydroperoxide. The invention has particular utility by providing a relatively pollution-free method of preparing dibenzothiazolyl disulfides.
Inventors
- 👤 James J. Tazuma
- 👤 Angelo Bergomi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 05:42
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/76; C07D277/78
Claims Analysis
Total Claims: 2
Claim 1
Independent Claim
170 words
A method of preparing dibenzothiazolyl disulfide having a melting point of about 180° C. as determined with a capillary tube with a heating rate of about 1° C. per minute, in a yield of at least about 98 percent without the aid of a mineral acid where the byproducts are water and dimethylphenylcarbinol instead of inorganic salt byproducts, which method consists of oxidizing mercaptobenzothiazole in a solution of alcohol selected from at least one of methyl alcohol and isopropyl alcohol at a temperature in the range of about 30° C. to about 80° C., but not above the boiling point of said alcohol solution, by reacting cumene hydroperoxide therewith; where said alcohol solution has an autogenous acid-base condition developed by the reaction system itself, where said alcohol solution comprises from 100 to about 80 weight percent of said alcohol and correspondingly up to about 20 weight percent water, and where the mole ratio of said cumene hydroperoxide to said mercaptobenzothiazole is in the range of about 0.3:1 to about 0.7:1.
Claim 2
Independent Claim
170 words
A method of preparing dibenzothiazolyl disulfide having a melting point of about 180° C. as determined with a capillary tube with a heating rate of about 1° C. per minute, in a yield of at least about 98 percent without the aid of a mineral acid where the byproducts are water and dimethylphenylcarbinol instead of inorganic salt byproducts, which method consists of oxidizing mercaptobenzothiazole in a solution of alcohol selected from at least one of methyl alcohol and isopropyl alcohol at a temperature in the range of about 30° C. to about 80° C., but not above the boiling point of said alcohol solution, by reacting cumene hydroperoxide therewith; where said alcohol solution has an autogenous acid-base condition developed by the reaction system itself, where said alcohol solution comprises from 100 to about 80 weight percent of said alcohol and correspondingly up to about 20 weight percent water, and where the mole ratio of said cumene hydroperoxide to said mercaptobenzothiazole is in the range of about 0.3:1 to about 0.7:1.
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) | 1982-03-05 | 1982-09-04 | 1983-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-05 | 1986-09-04 | 1987-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-05 | 1990-09-04 | 1991-03-06 | $7700.00 | Window Closed / Lapsed |