ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

SnCl₂-catalyzed synthesis of carbamates from renewable origin alcohols

Márcio José da Silva and Diego Morais Chaves

Federal University of Viçosa, Viçosa, Brazil

E-mail: silvamj2003@ufv.br

Abstract: Effects of structure and reactivity of renewable origin alcohols in the conversion and selectivity of the SnCl₂-catalyzed reactions in the presence and absence of urea were assessed. Convenient simple and suitable method for the synthesis of carbamates from renewable origin alcohols and urea in one-step are provided. We have assessed the activity of SnCl₂ catalyst, a commercially affordable Lewis acid, in reactions of urea alcoholysis with different natural origin alcohols (geranyl, neryl, bornyl, cinnamyl, α-terpinyl and benzyl alcohols), aiming to synthesize carbamates, which are biologically active compounds, building blocks in organic synthesis and raw material to synthesize polyurethanes. The low cost of urea, the water tolerant catalyst and phosgene free reaction are positive aspects of this carbamates synthesis process. The different reaction pathways were assessed. A mechanism was proposed based on FT-IR experiments and experimental data.

Keywords: Tin(II) catalysts ; Carbamates ; Terpenic alcohols ; Phosgene free process 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-017-0349-7

Chemical Papers 72 (5) 1169–1180 (2018)