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Derivatives of cardonol through the Ene reaction with diethyl azodicarboxylate

Atanu Biswas, Carlucio R. Alves, Maria T. S. Trevisan, Janet Berfield, Roselayne F. Furtado, Zengshe Liu, Huai N. Cheng
Journal of the Brazilian Chemical Society 2016 v.27 no.6 pp. 1078-1082
byproducts, cashew nuts, catalysts, chemical reactions, energy conservation, heat, hulls, liquids, microwave treatment, nuclear magnetic resonance spectroscopy, phenolic compounds, viscosity
Cardanol is an alkyl/alkenyl phenolic material obtained from cashew nut shell liquid (CNSL), which is a byproduct of cashew nut processing. In an effort to develop new uses, cardanol was derivatized for the first time with diethyl azodicarboxylate (DEAD) through the ene reaction. The reaction was facile and required only the application of heat without a catalyst. Both conventional heating and microwave heating were shown to be effective; the latter entailed much shorter reaction time and substantial energy savings. The reaction product (a hydrazino-ester derivative of cardanol) was characterized by nuclear magnetic resonance (NMR). The product increased in viscosity with time and may be useful as a viscosifier in oil-based commercial formulations and as a synthon for further organic reactions.