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Aminolysis of socrose. I

I. Ježo

Slovak Academy of Sciences, Bratislava

 

Abstract: The influence of time, temp., and various types and amts. of catalysts on the interaction of 100 ml. sucrose and 250 ml 25% NH4OH was studied. After the end of the reaction, 525g. Na2CO3 was added and the mixt. aerated to expel NH3. The mixt. was continuously extd. with Et2O and the ext. subjected to fractional distn. at normal and reduced pressure. Detailed analysis indicated that the mixt. consisted mainly of the 2-Me, 2,5-di-Me,2,6-di-Me derivs. of pyrazine(pyrazine fraction),and the 4-Me,2,4-di-Me and -hydroxymethyl derivs. of imidazole (imidazole fraction). The overall yield of both fractions increased with time indefinitely,18hrs. being the most convenient time. In the absence of catalyst,220° was the optimal temp. (25%) yield). The best catalysts were (NH4)3PO4 (0.625% in the reaction mixt. as optimal concn.) and ZnO with respective yields, at the optimal temp. (180°), 19% and 12.5%. Although in the presence of ZnCl2 or Cu(NH34SO4yields are high,these catalysts favor also the formation of humin substances. It is suggested that these products are formed through hydrolysis of sucrose, formation of glucosamine (I), condensation to deoxyfructosazine (II), (Kuhn, et al., CA 55, 27094b), or to the resp.6isomer by condensation of I with fructosamine. These latter compds. by thermal detachment of their side chains yield the pyrazine fraction and the fragments which by further condensations lead to the formation of the compds. of the imidazole fraction. This hypothesis is based on the fact that I and II under identical conditions yield mixts. of reaction products which are quant. and qual. similar to those obtained from sucrose.

Full paper in Portable Document Format: 172a126.pdf (in Slovak)

 

Chemical Papers 17 (2) 126–139 (1963)

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