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Issue 7, 2018
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Process systems for the carbonate interchange reactions of DMC and alcohols: efficient synthesis of catechol carbonate

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Abstract

A range of organic carbonates was synthesised from dimethylcarbonate (DMC) and different alcohols by base-catalysed carbonate interchange reactions (CIRs). Dimethyl carbonate – used as a green and efficient reagent as well as the reaction solvent – was coupled to methanol-removing systems to break the reaction equilibrium and thus obtain near quantitative yields of the desired carbonates. Two different methanol-removing systems are described, one based on azeotropic distillation (reactive azeotropic distillation, RAD) and one based on methanol absorption (reactive vapour absorption, RVA). A comparison between the two systems is described and some conclusions based on reaction metrics are discussed. The methods were applied to the synthesis of aliphatic asymmetric alkyl-methyl carbonates and to the synthesis of catechol carbonate, using both homogeneous (NaOMe and trioctylmethylphosphonium methylcarbonate, P8881-MC) as well as heterogeneous (MgO) catalysts.

Graphical abstract: Process systems for the carbonate interchange reactions of DMC and alcohols: efficient synthesis of catechol carbonate

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Publication details

The article was received on 18 Jan 2018, accepted on 13 Mar 2018 and first published on 14 Mar 2018


Article type: Paper
DOI: 10.1039/C8CY00119G
Citation: Catal. Sci. Technol., 2018,8, 1971-1980
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    Process systems for the carbonate interchange reactions of DMC and alcohols: efficient synthesis of catechol carbonate

    T. Tabanelli, S. Cailotto, J. Strachan, A. F. Masters, T. Maschmeyer, A. Perosa and F. Cavani, Catal. Sci. Technol., 2018, 8, 1971
    DOI: 10.1039/C8CY00119G

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