Synthesis of a cardanol-amine derivative using an ionic liquid catalyst

Abstract

Cardanol is a biobased raw material derived from cashew nut shell liquid. In order to extend its utility, new derivatives and additional applications are useful. In this work cardanol was first epoxidized, and a novel aniline derivative prepared from it under mild reaction conditions with the help of an ionic liquid catalyst. The reaction chemistry was studied by using nuclear magnetic resonance. The resulting aminohydrin adduct showed antioxidant property and should also be a useful synthon for further reactions. As an example, the aminohydrin was shown to undergo a condensation reaction with formaldehyde to form a prepolymer, which could be further reacted to form thermosetting resins.

Graphical abstract

Keywords

cardanol / epoxidation / aminohydrin / aniline / ionic liquid / aniline-formaldehyde

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Acknowledgements

The authors thank Janet Berfield for expert technical assistance and Karl Vermillion for NMR data. Atanu Biswas and Roselayne Ferro Furtado thank CNPq (process no. 405506/2013-9) for the support of this work through the Science without Borders program. Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the U.S. Department of Agriculture. USDA is an equal opportunity provider and employer.

Funding

RIGHTS & PERMISSIONS

2016 Higher Education Press and Springer-Verlag Berlin Heidelberg