| 词条 | Hydrofuramide |
| 释义 |
| ImageFile = Hydrofuramide.svg | ImageSize = | IUPACName = (E)-1-(Furan-2-yl)-N-[furan-2-yl-[(E)-furan-2-ylmethylideneamino]methyl]methanimine | OtherNames = N,N-Difurfurylidene-2-furanmethanediamine |Section1={{Chembox Identifiers | CASNo = 494-47-3 | PubChem = 9570073 | EINECS = 207-790-8 | ChemSpiderID = 7844541 | SMILES = C1=COC(=C1)/C=N/C(/N=C/C2=CC=CO2)C3=CC=CO3 | InChI = 1/C15H12N2O3/c1-4-12(18-7-1)10-16-15(14-6-3-9-20-14)17-11-13-5-2-8-19-13/h1-11,15H/b16-10+,17-11+ | InChIKey = CYGDSXFTXXFMNI-OTYYAQKOBP | StdInChI = 1S/C15H12N2O3/c1-4-12(18-7-1)10-16-15(14-6-3-9-20-14)17-11-13-5-2-8-19-13/h1-11,15H/b16-10+,17-11+ | StdInChIKey = CYGDSXFTXXFMNI-OTYYAQKOSA-N |Section2={{Chembox Properties | C=15 | H=12 | N=2 | O=3 | Appearance = crystals | Density = 1.23 g/mL @ 20 °C | MeltingPtC = 118 to 119 | MeltingPt_notes = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}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] SynthesisHydrofuramide was prepared in 1960 by Kapur via the reaction of furfural with aqueous ammonia in chilled ethanol solution.[3] ReactionsThe 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] ApplicationsRubber vulcanizationHydrofuramide 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] RaticideHydrofuramide 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 technologyDevelopment of a pink color in a modified Badouin test, employing hydrofuramide, is diagnostic for adulteration of butter with cheap hydrogenated vegetable oil.[10] References1. ^{{cite journal | author = Chin-Hsing Chou | title = Synthesis of N,N-di(arylmethylidene)arylmethanediamines by flash vacuum pyrolysis of arylmethylazides| journal = Tetrahedron | volume = 60 | pages = 6581–6584 | year = 2004| last2 = Chu| first2 = Li-Tse|last3 = Chiu| first3 = Shao-Jung| last4 = Lee| first4 = Chin-Fan|last5 = She| first5 = Yao-Teng | doi = 10.1016/j.tet.2004.06.082 | issue = 31}} 2. ^1 {{cite journal | author = G. Marches| title = Biological study of a new raticide substance, hydrofuramide| journal = Acad. rep. populare Romine, Studii cercetari biol., Ser. "Biol. animala"| volume = 10| pages = 335–44| year = 1958}} 3. ^{{cite journal | author = O. P. Kapur| title = The preparation and properties of hydrofuramide| journal = Journal of Scientific & Industrial Research| volume = 19B | pages =509–10| year = 1960| last2 = Srinivasan | first2 = M. |last3 = Subrahmanyan | first3 = V.}} 4. ^Gustav Sotek, “N,N-bisfurfuryl-2-furylmethanediamine, its production and use in pharmaceuticals”, World Patent 8704160 (1987) 5. ^{{cite journal | author = Charles F. Winans| title = Hydrogenation of aldehydes in the presence of ammonia| journal = Journal of the American Chemical Society| volume = 61|pages = 3566–7| year = 1939|doi=10.1021/ja01267a102 }} 6. ^{{cite journal | author = Henry Gilman| title = The reduction of hydrofuramide to tri-α-furfurylamine| journal = Iowa State College Journal of Science| volume = 5| pages = 193–4| year = 1931| last2 = Dickey| first2 =J. B.}} 7. ^{{cite journal | author = M. Aguilar| title = Chemical and electrochemical reduction of nitrogenated furfural derivatives. Synthesis of furfurylamine | journal = Revista de la Sociedad Quimica de Mexico| volume = 40 | issue = 2| pages = 81–87| year = 1996| last2 = Alfan| first2 = F. J. | last3 = Albores Velasco| first3 = M.}} 8. ^{{cite journal | author = M. Bravar| title = Kinetics of additive-containing sulfur-thiazole vulcanization of styrene-butadiene| journal = Kautschuk Gummi Kunststoffe| volume = 41 | issue = 5| pages =462–5| year = 1988| last2 = Jelencic | first2 = J. |last3 = Dabetic | first3 = M.}} 9. ^{{cite journal | author = B. Banerjee | title = Vulcanization of natural rubber: influence of hydrofuramide on sulfenamide acceleration system| journal = Journal of the Indian Chemical Society| volume = 59 | issue = 3| pages =403–7| year = 1982| last2 = Chakravarty| first2 = S. N.}} 10. ^{{cite journal | author = O. P Kapur| title = A modified Baudouin test for the detection of adulteration of butter and ghee with vanaspati| journal = Journal of Scientific & Industrial Research| volume = 17B| pages = 471–2| year = 1958| last2 = Srinivasan| first2 = M.|last3 = Subrahmanyan| first3 = V.}} 2 : Furans|Imines |
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