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Aminolysis of sucrose. V. The reaction between sucrose and aqueous ethanolamine solution

I. Ježo and I. Luzak

Slovak Academy of Sciences, Bratislava

 

Abstract: cf. CA 62, 5322f. The aminolysis of sucrose was carried out by heating (autoclave, 18 hrs.) 50 g. in 100 ml. H2O and 61 g. ethanolamine in 150 ml. H2O at higher temps. The mixt. was sepd. into 2 fractions and the following compds. were isolated and identified: ethylenediamine, b. 116-18°/745mm. [dipicrate m. 239-40° (H2O); H2PtCl6 salt 252-3° (H2O-EtOH); diacetyl deriv. m. 171-2° (benzene)]; 1-ethylpiperazine, b. 156°/747, n20D 1.4605, d20 1.0059 [picrate m. 255-7° (H2O); tartrate m. 229-30° (H2O)]; 2-methyl-4-(2-hydroxyethyl-1,4,5,6-tetrahydropyrazine, b. 116-18°/64, n20D 1.5039, d20 1.0319 [dipicrate m. 253° (H2O); H2PtCl6 salt m. 226-7° (dil. EtOH)]; a mixt. of 1-(2-hydroxyethyl)-2-methyl 1,4,5,6-tetrahydropyrazine and 1-(2-hydroxyethyl)-2-methyl-2-imidazoline, b. 95-115°/0.01; 1-(2-hydroxyethyl)-2-methyl-2-imidazoline, b. 117-19°/0.01 [picrate m. 231-2° (H2O); 0.5 H2PtCl6 salt 166° (dil. EtOH)]; 1,4-bis(hydroxyethyl)-2-methyl-1,4-dihydropyrazine, b. 116-22°/0.001, n20D 1.5214 [picrate m. 219-2° (H2O)]; and a compd. C11H21N3O2, b. 125-7°/0.001, n20D 1.5327; picrate m. 240-1° (H2O). The formation of these compds. was explained by the same reaction mechanism as the reaction of sucrose with aq. NH3 solns. at higher temps.

Full paper in Portable Document Format: 1811a837.pdf (in Slovak)

 

Chemical Papers 18 (11) 837–851 (1964)

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