1001-56-5Relevant articles and documents
Bouchy et al.
, p. 211 (1973)
Production of Acrylonitrile and Other Unsaturated Nitriles from Hydrocarbons Using a Plasma
Henis, Neil B.H.,So, Ying-Hung,Miller, Larry L.
, p. 4632 - 4633 (1981)
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Production of Acrylonitrile and Other Unsaturated Nitriles from Alkenes and Alkynes
Henis, Neil B.,Miller, Larry L.
, p. 2526 - 2529 (1982)
Passage of unsaturated organic molecules trough a 13.56-MHz radio-frequency discharge, in the presence of cyanogen, results in the formation of unsaturated nitriles.Acrylonitrile was the major product from ethylene, propylene, acrolein, methyl vinyl ketone, or 1,1,1-trifluoropropylene. 1-Butene, 2-butene, and isobutylene gave mixtures of nitrile products with the CN situated at vinylic or allylic positions. 2-Butyne gave 1-cyanopropyne.Other compounds gave only low yields of nitriles and considerable polymer.The effects of power, pressure, flow rate, and ratios of reactants on the yields of acrylonitrile from propylene and cyanogen were studied.A typical power yield of acrylonitrile was 30 g kW-1 h-1.Maximum material yields of nitrile products were obtained at intermediate powers and pressures.The products are consistent with a reaction scheme involving attack of initially formed cyano radicals on the organic substrate.This step forms activated radical intermediates, which decay through elimination of an atom or group.The atom or group which is most weakly bound is preferentially lost.
3-pyridazinylnitrenes and 2-pyrimidinylnitrenes
Torker, Sebastian,Kvaskoff, David,Wentrup, Curt
, p. 1758 - 1770 (2014/03/21)
Mild flash vacuum thermolysis of tetrazolo[1,5-b]pyridazines 8T generates small amounts of 3-azidopyridazines 8A (8aA, IR 2145, 2118 cm-1; 8bA, 2142 cm-1). Photolysis of the tetrazoles/azides 8T/8A in Ar matrix generates 3-pyridazinylnitrenes 9, detected by ESR spectroscopy (9a: D/hc = 1.006; E/hc = 0.003 cm-1). Cyanovinylcarbenes 11, derived from 4-diazobut-2-enenitriles 10, are also detected by ESR spectroscopy (11a: D/hc = 0.362; E/hc = 0.021 cm-1). Carbenes 11 rearrange to cyanoallenes 12 and 3-cyanocyclopropenes 13. Triazacycloheptatetraenes 20 were not observed in the photolyses of 8. Photolysis of tetrazolo[1,5-a]pyrimidines/2- azidopyridmidines 18T/18A in Ar matrices at 254 nm yields 2-pyrimidinylnitrenes 19, observable by ESR, UV, and IR spectroscopy (19a: ESR: D/hc = 1.217; E/hc = 0.0052 cm-1). Excellent agreement with the calculated IR spectrum identifies the 1,2,4-triazacyclohepta-1,2,4,6-tetraenes 20 (20a, 1969 cm -1; 20b, 1979 cm-1). Compounds 20 undergo photochemical ring-opening to 1-isocyano-3-diazopropenes 23. Further irradiation also causes Type II ring-opening of pyrimidinylnitrenes 19 to 2-(cyanimino)vinylnitrenes 21 (21a: D/hc = 0.875; E/hc = 0.00 cm-1), isomerization to cyaniminoketenimine 25 (2044 cm-1), and cyclization to 1-cyanopyrazoles 22. The reaction mechanisms are discussed and supported by DFT calculations on key intermediates and pathways. There is no evidence for the interconversion of 3-pyridazinylnitrenes 9 and 2-pyrimidinylnitrenes 19.
Process for producing 5-amino-3-methylpyrazole
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, (2008/06/13)
A process for producing 5-amino-3-methylpyrazole which comprises reacting hydrazine with a reaction intermediate containing at least one compound selected from the group consisting of 3-chloro-3-butenonitrile and 2,3-butadienenitrile, which intermediate is obtainable from 2,3-dichloropropene and hydrocyanic acid. A process for producing 5-amino-4-chloro-3-methylpyrazole which comprises chlorinating 5-amino-3-methylpyrazole obtainable by the above-mentioned reaction, in the presence of hydrochloric acid.