Acetylene and nitrogen

Ma.nufa.cture. The principal manufacturers of A/-vinyl-2-pyrrohdinone are ISP and BASF. Both consume most of their production captively as a monomer for the manufacture of PVP and copolymers. The vinylation of 2-pyrrohdinone is carried out under alkaline catalysis analogous to the vinylation of alcohols. 2-Pyrrohdinone is treated with ca 5% potassium hydroxide, then water and some pyrroHdinone are distilled at reduced pressure. A ca 1 1 mixture (by vol) of acetylene and nitrogen is heated at 150—160°C and ca 2 MPa (22 atm). Fresh 2-pyrrohdinone and catalyst are added continuously while product is withdrawn. Conversion is limited to ca 60% to avoid excessive formation of by-products. The A/-vinyl-2-pyrrohdinone is distilled at 70-85°C at 670 Pa (5 mm Hg) and the yield is 70-80% (8). 

Of the few recent publications in this field two papers are noteworthy these are Cramer s report on the synthesis of 3,3 -diisoxazolyl in 60-70% yield from acetylene and nitrogen oxides and on the synthesis of a mixture of 5,5 -diisoxazolyls [34 35, R = Me2C(OH)] from fulminic acid and diacetyiene. ... 

Although mechanisms have been advanced to account for the formation of the majority of the identified products from acetylenes and nitrogen-containing heterocycles, most are based on plausible analogies or on the trapping of an occasional postulated intermediate. Genuine mechanistic studies have been carried out for very few of the reactions noted in this review. 

The union of acetylene and nitrogen to hydrocyanic acid takes place rather smoothly if the easy clecomposability of acetylene is lessened by dilution with hydrogen, as was already done by Berthelot.6 His experiments were recently again taken up by Gruszkiewicz.7 The electrodes were blackened by a deposition of carbon except with a maximum content of acetylene of 5 per cent, by volume (composition of tne gas mixture 5 per cent, acetylene, 5 per cent, nitrogen and 90 per cent, hydrogen). 

Acetylene and nitrogen.—100 C2H24-100N2 gave no hydrogen and no hydrocarbon, but 88.6 N2 and a solid substance, C16H16N2. 

Hydrocyanic acid may be prepared in various ways by passing electric sparks through a mixture of acetylene and nitrogen,... 

Problem 9.7 Relate the structures of the isoelectronic molecules acetylene and nitrogen including a comparison of the corresponding molecular orbital description. 

Ammonia and amines add to simple olefins only when catalysed and under energetic conditions. For example, jV-methylaniline is obtained in 80-90% yield from aniline and ethylene at 300°/200 atm in the presence of sodium.1 Rather high pressures and catalysts are also necessary for addition of amines to a C-C triple bond 2-4 however, the reaction often does not stop at simple vinylation but gives the Schiff base instead of the expected isomeric vinyl-amine.2-4 Tertiary amines can also be vinylated, as when neurine2 is obtained in good yield from a 2 1 mixture of acetylene and nitrogen at 60-70°/20 atm 5... 

Koch, H. J. Evans, and S. Russell, Reduction of acetylene and nitrogen gas by breis and cell-free extracts of soybean root nodules. Plant Physiol. 42 466 (1967). 

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