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Issue 69, 2014
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Driving an equilibrium acetalization to completion in the presence of water

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Abstract

Formation of an acetal from a carbonyl substrate by condensation with an alcohol is a classical reversible equilibrium reaction in which the water formed must be removed to drive the reaction to completion. A new method has been developed for acetalization of carbonyl substrates by diols in the presence of water. Complexation of poly(4-styrenesulfonic acid) with poly(4-vinylpyridine) generates a catalytic membrane of polymeric acid at the interface between two parallel laminar flows in a microchannel of a microflow reactor. The catalytic membrane provides a permeable barrier between the organic layer and water-containing layer in the reaction, and permits discharge of water to the outlet of the microreactor to complete the acetalization. Condensation of a variety of carbonyl substrates with diols proceeded in the presence of water in the microflow device to give the corresponding acetals in yields of up to 97% for residence times of 19 to 38 s.

Graphical abstract: Driving an equilibrium acetalization to completion in the presence of water

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Supplementary files

Article information


Submitted
15 Jul 2014
Accepted
13 Aug 2014
First published
13 Aug 2014

RSC Adv., 2014,4, 36864-36867
Article type
Communication
Author version available

Driving an equilibrium acetalization to completion in the presence of water

M. Minakawa, Y. M. A. Yamada and Y. Uozumi, RSC Adv., 2014, 4, 36864
DOI: 10.1039/C4RA07116F

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