US3670007A
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Aminomalonitrile and method of preparation thereof
Assignee: Salk Institute for Biological Studies
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Filing: 1967-11-21
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Granted: 1972-06-13
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Expires: 1987-11-21
Abstract
Abstract The chemical aminomalononitrile and methods for making it comprising reacting oximinomalononitrile or phenazomalononitrile with approximately stoichiometric amounts of one of the group consisting of unoxidized aluminum, zinc and sodium dithionite. Formation of aminomalononitrile using zinc must take place in an acid solution. In each case, the reaction mixture is externally cooled until the initial exothermic reaction is substantially complete. Preferably, the aminomalononitrile so formed is isolated as a salt such as the hydrochloride, hydrobromide and toluenesulfonate.
Inventors
- 👤 James P Ferris
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 16:18
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/30; C07D263/34; C07C; C07C255/00; C07D233/00; C07D233/54; C07D233/66; C07D233/90
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
41 words
A process in accordance with claim 1 wherein a strong acid, selected from the group consisting of hydrogen chloriDe, hydrogen bromide and p-toluene sulfonic acid, is added to said aminomalononitrile formed, from said reaction mixture, to produce the corresponding salt thereof.
Claim 2
Dependent Claim
78 words
A process for preparing aminomalononitrile which comprises reacting an etheral solution of a malononitrile selected from the group consisting of oximinomalononitrile and phenazomalononitrile with aluminum and water, the initial molar ratio of aluminum to malononitrile being between about 1.3 to 1 and about 4 to 1 and the initial molar ratio of water to malononitrile being at least about 2 to 1, said reaction being carried out at a temperature below the reflux temperature of the reaction mixture.
Claim 3
Dependent Claim
39 words
A process in accordance with claim 3 wherein the aluminum is in the form of an amalgam with mercury and the initial molar ratio of water to malononitrile is between about 3 to 1 and about 6 to 1.
Claim 4
Dependent Claim
121 words
A process for preparing aminomalononitrile salts which comprises: a. reacting an ethereal solution of a malononitrile selected from the group consisting of oximinomalononitrile and phenazomalononitrile with aluminum and water, the initial molar ratio of aluminum to malononitrile being between about 1.3 to 1 and about 4 to 1, the initial molar ratio of water to malononitrile being between 3 to 1 and about 6 to 1, said reaction being carried out at a temperature below the reflux temperature of the reaction mixture, whereby said malononitrile is reduced to aminomalononitrile; b. separating any aniline present in the reaction mixture and then separating aminomalononitrile from the reaction mixture; and c. adding a strong acid to the aminomalononitrile to form the corresponding salt thereof.
Claim 5
Dependent Claim
28 words
A process in accordance with claim 5 wherein the stong acid is a member selected from the group consisting of hydrogen chloride, hydrogen bromide and p-toluene sulfonic acid.
Claim 6
Dependent Claim
66 words
A process for preparing aminomalononitrile which comprises reacting an etheral solution of a malononitrile selected from the group consisting of oximinomalononitrile and phenazomalononitrile with zinc in an aqueous acidic medium, the initial molar ratio of zinc to malononitrile being between about 2 to 1 and about 2.5 to 1, and said reaction being carried out at a temperature below the reflux temperature of the reaction mixture.
Claim 7
Dependent Claim
104 words
A process for preparing aminomalononitrile salts which comprises: a. reacting an ethereal solution of a malononitrile selected from the group consisting of oximinomalononitrile and phenazomalononitrile with zinc in an aqueous acidic medium, the initial molar ratio of zinc to malononitrile being between about 2 to 1 and about 2.5 to 1, and said reaction being carried out at a temperature below the reflux temperature of the reaction mixture, whereby said malononitrile is reduced to aminomalononitrile; b. separating aminomalononitrile from the reaction mixture after separating out any aniline first formed; and c. adding a strong acid to the aminomalononitrile to form the corresponding salt thereof.
Claim 8
Dependent Claim
82 words
A process for preparing aminomalononitrile which comprises reacting in an aqueous medium an etheral solution of a malononitrile selected from the group consisting of oximinomalononitrile and phenazomalononitrile with a reducing agent selected from the group consisting of sodium dithionite and potassium dithionite dissolved in water, the initial molar ratio of reducing agent to malononitrile being between about 2 to 1 and about 3 to 1, and said reaction being carried out at a temperature below the reflux temperature of the reaction mixture.
Claim 9
Dependent Claim
121 words
A process for preparing aminomalononitrile salts which comprises: a. reacting in an aqueous medium an ethereal solution of a malononitrile selected from the group consisting of oximinomalononitrile and phenazomalononitrile with a reducing agent selEcted from the group consisting of sodium dithionite and potassium dithionite dissolved in water, the initial molar ratio of reducing agent to malononitrile being between about 2 to 1 and about 3 to 1, and said reaction being carried out at a temperature below the reflux temperature of the reaction mixture, whereby said malononitrile is reduced to aminomalononitrile; b. separating any aniline formed and then separating out the animonalononitrile from the reaction mixture; and c. adding a strong acid to said aminomalononitrile to form the corresponding salt thereof.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-06-13 | 1975-12-13 | 1976-06-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-06-13 | 1979-12-13 | 1980-06-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-06-13 | 1983-12-13 | 1984-06-13 | $7700.00 | Window Closed / Lapsed |