Two alternative routes for 1,2-cyclohexanediol synthesis by means of green processes: Cyclohexene dihydroxylation and catechol hydrogenation

Authors:  Claudia Antonetti, Anna Maria Raspolli Galletti, Pasquale Accorinti, Stefano Alini, Pierpaolo Babini, Katerina Raabova, Elena Rozhko, Aurora Caldarelli, Paolo Righi, Fabrizio Cavani, Patricia Concepcion

Abstract:
In this paper we compare two different reactions, aimed at the synthesis of 1,2-cyclohexanediol. Specifically: (a) the direct epoxidation and hydrolysis (dihydroxylation) of cyclohexene to trans-1,2- cyclohexanediol, with an aqueous solution of hydrogen peroxide, and (b) the hydrogenation of catechol to a mixture of cis and trans-1,2-cyclohexanediol, in an attempt to establish green protocols for the synthesis of diols. Both reactions, the dihydroxylation of cyclohexene and the hydrogenation of catechol, were carried out without organic solvents. In the former case, an unprecedented 97.4% yield to the glycol was obtained, by selecting proper reaction conditions and using a tungstic acid/phosphoric acid catalyst, in a biphasic system with a phase-transfer agent. In the second approach, a heterogeneous aluminasupported Ru(OH)x catalyst was used, and a 90% yield to the glycol was obtained. A comparison of the two processes allowed to show the lower environmental impact of the catechol hydrogenation route.

Keywords:
Cyclohexene dihydroxilation
1,2-Cyclohexanediol
Catechol hydrogenation
Tungstate catalyst
Supported ruthenium hydroxide

Published in: Applied catalysis A: General  (Volume 466, Pages 1-314, 10 September 2013)

Publisher: Elsevier  

ISSN Information: 0926-860X

Two alternative routes for 1,2-cyclohexanediol synthesis by means of green processes: Cyclohexene dihydroxylation and catechol hydrogenation

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