Hydrofuramide
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| Names | |
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| IUPAC name
(E)-1-(Furan-2-yl)-N-[furan-2-yl-[(E)-furan-2-ylmethylideneamino]methyl]methanimine
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| Other names
N,N'-Difurfurylidene-2-furanmethanediamine
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.083 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C15H12N2O3 | |
| Molar mass | 268.272 g·mol−1 |
| Appearance | crystals |
| Density | 1.23 g/mL @ 20 °C |
| Melting point | 118 to 119 °C (244 to 246 °F; 391 to 392 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hydrofuramide is a condensation product of three molar equivalents of furfural with two molar equivalents of ammonia. Hydrofuramide is a crystalline solid with a melting point of 118-119 °C.[1] The molecule may be described as a diimine with three pendant furanyl rings. Hydrofuramide is a versatile specialty chemical with applications in diverse areas, including rubber additives, pharmaceutical intermediates, preservatives, and rodenticides.[2]
Synthesis
[edit]Hydrofuramide was prepared in 1960 by Kapur via the reaction of furfural with aqueous ammonia in chilled ethanol solution.[3]
Reactions
[edit]The reactive imine double bonds of hydrofuramide are easily reduced. Reduction with aqueous sodium borohydride yields N,N-bisfurfuryl-2-furylmethanediamine, useful as an antihypertensive drug compound.[4]
Catalytic hydrogenation of hydrofuramide with Raney nickel in the presence of ammonia in ethanol yields mixtures of furfurylamine and difurfurylamine.[5] By contrast, hydrogenation in acetic acid-ethanol, employing platinum oxide catalyst yielded the tertiary amine tri-furfurylamine after neutralization.[6] Furthermore, lithium aluminium hydride reduction of hydrofuramide yields furfurin, a tetracyclic compound.[7]
Applications
[edit]Rubber vulcanization
[edit]Hydrofuramide has shown effectiveness as a synergist with zinc stearate in enhancing the rate of vulcanization of styrene-butadiene rubber.[8] Similar synergistic effect was seen in the vulcanization of natural rubber with hydrofuramide-sulfenamide activator where introduction of hydrofuramide reduced induction time, scorch time, and optimum cure time.[9]
Raticide
[edit]Hydrofuramide has been found to be selectively toxic to rats. For all types of rats the lethal dose is 1 g/kg body weight. The chemical is less toxic to guinea pigs and has little or no toxicity to swine, dogs, cats or birds.[2]
Food technology
[edit]Development of a pink color in a modified Badouin test, employing hydrofuramide, is diagnostic for adulteration of butter with cheap hydrogenated vegetable oil.[10]
References
[edit]- ^ Chin-Hsing Chou; Chu, Li-Tse; Chiu, Shao-Jung; Lee, Chin-Fan; She, Yao-Teng (2004). "Synthesis of N,N-di(arylmethylidene)arylmethanediamines by flash vacuum pyrolysis of arylmethylazides". Tetrahedron. 60 (31): 6581–6584. doi:10.1016/j.tet.2004.06.082.
- ^ a b G. Marches (1958). "Biological study of a new raticide substance, hydrofuramide". Acad. Rep. Populare Romine, Studii Cercetari Biol., Ser. "Biol. Animala". 10: 335–44.
- ^ O. P. Kapur; Srinivasan, M.; Subrahmanyan, V. (1960). "The preparation and properties of hydrofuramide". Journal of Scientific & Industrial Research. 19B: 509–10.
- ^ Gustav Sotek, “N,N-bisfurfuryl-2-furylmethanediamine, its production and use in pharmaceuticals”, World Patent 8704160 (1987)
- ^ Charles F. Winans (1939). "Hydrogenation of aldehydes in the presence of ammonia". Journal of the American Chemical Society. 61 (12): 3566–7. doi:10.1021/ja01267a102.
- ^ Henry Gilman; Dickey, J. B. (1931). "The reduction of hydrofuramide to tri-α-furfurylamine". Iowa State College Journal of Science. 5: 193–4.
- ^ M. Aguilar; Alfan, F. J.; Albores Velasco, M. (1996). "Chemical and electrochemical reduction of nitrogenated furfural derivatives. Synthesis of furfurylamine". Revista de la Sociedad Química de Mexico. 40 (2): 81–87.
- ^ M. Bravar; Jelencic, J.; Dabetic, M. (1988). "Kinetics of additive-containing sulfur-thiazole vulcanization of styrene-butadiene". Kautschuk Gummi Kunststoffe. 41 (5): 462–5.
- ^ B. Banerjee; Chakravarty, S. N. (1982). "Vulcanization of natural rubber: influence of hydrofuramide on sulfenamide acceleration system". Journal of the Indian Chemical Society. 59 (3): 403–7.
- ^ O. P Kapur; Srinivasan, M.; Subrahmanyan, V. (1958). "A modified Baudouin test for the detection of adulteration of butter and ghee with vanaspati". Journal of Scientific & Industrial Research. 17B: 471–2.