ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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)