Derivatives of cardanol through the ene reaction with diethyl azodicarboxylate

Authors: Biswas, Atanu; ALVES, CARLUCIO - Universidade Estadual Do Ceara; TREVISAN, MARIA - Universidade Federal Do Ceara (UFC); Berfield, Janet; FURTADO, ROSELAYNE - Embrapa; Liu, Zengshe - Kevin; Cheng, Huai

Submitted to: Journal of Brazilian Chemical Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 11/15/2015
Publication Date: 4/1/2016
Publication URL: https://handle.nal.usda.gov/10113/5695387
Citation: Biswas, A., Alves, C.R., Trevisan, M.T.S., Berfield, J., Furtado, R.F., Liu, Z., Cheng, H.N. 2016. Derivatives of cardanol through the ene reaction with diethyl azodicarboxylate. Journal of Brazilian Chemical Society. 27(6):1078-1082.

Interpretive Summary: There has been a constant demand for environmentally friendly industrial chemicals derived from agricultural commodities, because they are renewable resources and potentially cheaper. The interest intensified during the last decade due to strict government and environmental regulations. Most of the current industrial chemicals originate from petroleum stock, which is toxic to the environment and difficult to dispose of. We have developed a novel solvent and catalyst-free green pathway to incorporating nitrogen into cardanol, a phenolic lipid obtained from cashew nut shell liquid (CNSL), which is a byproduct of cashew nut processing. Only a fraction of the cardanol obtained from cashew nut processing is used in the industrial field. Therefore, there is strong interest in developing new applications such as new polymers. Impact: These new materials perhaps can find use in the chemical industry as viscosifiers in resins, coatings, frictional materials, and cements. They may also function as surfactants and pigment dispersants for water-based inks, lubricants, and cosmetics. It is possible that they may have antimicrobial or pharmaceutical activities because other hydrazine derivatives exhibit these properties.

Technical Abstract: 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.