Hydrofuramide
Chemical compound
From Wikipedia, the free encyclopedia
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]
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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 | |
| Other names
N,N'-Difurfurylidene-2-furanmethanediamine | |
| 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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Synthesis
Reactions
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
Rubber vulcanization
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
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
Development of a pink color in a modified Badouin test, employing hydrofuramide, is diagnostic for adulteration of butter with cheap hydrogenated vegetable oil.[10]