Chemistry:Hydrofuramide

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Hydrofuramide
Hydrofuramide.svg
Names
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)
ChemSpider
EC Number
  • 207-790-8
UNII
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).
Infobox references

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

Hydrofuramide was prepared in 1960 by Kapur via the reaction of furfural with aqueous ammonia in chilled ethanol solution.[3]

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]

References

  1. 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. 
  2. 2.0 2.1 G. Marches (1958). "Biological study of a new raticide substance, hydrofuramide". Acad. Rep. Populare Romine, Studii Cercetari Biol., Ser. "Biol. Animala" 10: 335–44. 
  3. O. P. Kapur; Srinivasan, M.; Subrahmanyan, V. (1960). "The preparation and properties of hydrofuramide". Journal of Scientific & Industrial Research 19B: 509–10. 
  4. Gustav Sotek, “N,N-bisfurfuryl-2-furylmethanediamine, its production and use in pharmaceuticals”, World Patent 8704160 (1987)
  5. 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. 
  6. Henry Gilman; Dickey, J. B. (1931). "The reduction of hydrofuramide to tri-α-furfurylamine". Iowa State College Journal of Science 5: 193–4. 
  7. 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. 
  8. M. Bravar; Jelencic, J.; Dabetic, M. (1988). "Kinetics of additive-containing sulfur-thiazole vulcanization of styrene-butadiene". Kautschuk Gummi Kunststoffe 41 (5): 462–5. 
  9. 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. 
  10. 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.