US4229364A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Synthesis of 1,4-bis(dicyanomethylene) cyclohexane
Assignee: Procter and Gamble Co
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Filing: 1979-05-14
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Granted: 1980-10-21
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Expires: 1999-05-14
Abstract
Abstract 1,4-Bis(dicyanomethylene)cyclohexane is the chemical of choice for the synthesis of TCNQ. The present invention provides a simple convenient, three-step synthesis of 1,4-bis(dicyanomethylene)cyclohexane from hydroquinone which uses water as the reaction solvent.
Inventors
- 👤 Robert J. Crawford
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 08:37
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/45
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
62 words
A process for the preparation of 1,4-bis(dicyanomethylene)cyclohexane, comprising the steps: I. hydrogenating hydroquinone to provide 1,4-cyclohexanediol; II. oxidizing the 1,4-cyclohexanediol from Step (I) in the presence of a ruthenium catalyst to provide 1,4-cyclohexanedione; and III. condensing the 1,4-cyclohexanedione from Step (II) with two equivalents of malononitrile said steps (I), (II) and (III) each being carried out in water as the reaction solvent.
Claim 2
Dependent Claim
62 words
A process for the preparation of 1,4-bis(dicyanomethylene)cyclohexane, comprising the steps: I. hydrogenating hydroquinone to provide 1,4-cyclohexanediol; II. oxidizing the 1,4-cyclohexanediol from Step (I) in the presence of a ruthenium catalyst to provide 1,4-cyclohexanedione; and III. condensing the 1,4-cyclohexanedione from Step (II) with two equivalents of malononitrile said steps (I), (II) and (III) each being carried out in water as the reaction solvent.
Claim 3
Dependent Claim
17 words
A process according to claim 1 wherein hydrogenation Step (I) is carried out using W-7 Raney nickel.
Claim 4
Dependent Claim
21 words
A process according to claim 1 wherein oxidation step (II) is carried out using a ruthenium oxide or its equivalent, catalyst.
Claim 5
Dependent Claim
22 words
A process according to claim 3 wherein the ruthenium catalyst is ruthenium oxide, or its equivalent, and the oxidizing agent is hypochlorite.
Claim 6
Dependent Claim
21 words
A process according to claim 1 wherein condensation Step (III) is carried out in the presence of beta-alanine as the catalyst.
Claim 7
Dependent Claim
79 words
A process according to claim 1, comprising: hydrogenating hydroquinone in the presence of W-7 Raney nickel catalyst and water solvent to provide 1,4-cyclohexanediol; (II) oxidizing the 1,4-cyclohexanediol from Step (I) with sodium hypochlorite in the presence of a ruthenium oxide catalyst, or its equivalent, in water solvent to provide 1,4-cyclohexanedione; and (III) condensing the 1,4-cyclohexanedione from Step (II) with two equivalents of malononitrile in the presence of beta-alanine catalyst in water solvent, whereupon 1,4-bis(dicyanomethylene(cyclohexane precipitates from said water solvent.
References Cited (Backward Citations)
US2675390A
Cited
US3115506A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-21 | 1984-04-21 | 1984-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-21 | 1988-04-21 | 1988-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-21 | 1992-04-21 | 1992-10-21 | $7700.00 | Window Closed / Lapsed |