Bifunctional initiators: synthesis of phenylazo-formamidoethyl 4-t-butylazo-4-cyanovalerate |
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Authors: | C. I. Simionescu Eugenia Comanita Mariana Pastravanu Aura-Angelica Popa |
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Affiliation: | (1) Department of Organic and Macromolecular Chemistry, Polytechnic Institute of Jassy, RO-6600 Jassy, Romania |
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Abstract: | Summary The paper deals with the synthesis of the phenylazo-formamidoethyl 4-t-butylazo-4-cyanovalerate, a product which — by its two azo groups having different thermal stabilities — may be used in initiating processes of stepwise radicalic polymerization. The preparation is based on the condensation of the 4-t-butylazo-4-cyanovaleric acid chloride with N-hydroxy ethyl-phenylazoformamide (HEPF) in anhydrous chloroform, in the presence of pyridine. The initiator purification involves its passing over an alumina column, on using methylene chloride as eluent. HEPF is a new intermediate obtained by the reaction of the ethyl phenylazocarboxylate with ethanolamine. Both the HEPF structure and that of the bis-azo initiator is confirmed by elemental analysis and spectroscopic measurements (IR and H-NMR spectra), as well. |
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