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Molecules 2013, 18(2), 2419-2437; doi:10.3390/molecules18022419
Article

Sonolytic and Silent Polymerization of Methacrlyic Acid Butyl Ester Catalyzed by a New Onium Salt with bis-Active Sites in a Biphasic System — A Comparative Investigation

1, 1,*  and 2
Received: 22 November 2012 / Revised: 9 January 2013 / Accepted: 28 January 2013 / Published: 21 February 2013
(This article belongs to the Special Issue Phase Transfer Catalysis)
Download PDF [256 KB, 18 June 2014; original version 18 June 2014]

Abstract

Currently, ingenious new analytical and process experimental techniques which are environmentally benign techniques, viz., ultrasound irradiation, have become immensely popular in promoting various reactions. In this work, a novel soluble multi-site phase transfer catalyst (PTC) viz., 1,4-bis-(propylmethyleneammounium chloride)benzene (BPMACB) was synthesized and its catalytic efficiency was assessed by observing the kinetics of sonolytic polymerization of methacrylic acid butyl ester (MABE) using potassium persulphate (PPS) as an initiator. The ultrasound–multi-site phase transfer catalysis (US-MPTC)-assisted polymerization reaction was compared with the silent (non-ultrasonic) polymerization reaction. The effects of the catalyst and various reaction parameters on the catalytic performance were in detail investigated by following the kinetics of polymerization of MABE in an ethyl acetate-water biphasic system. From the detailed kinetic investigation we propose a plausible mechanism. Further the kinetic results demonstrate clearly that ultrasound-assisted phase-transfer catalysis significantly increased the reaction rate when compared to silent reactions. Notably, this environmentally benign and cost-effective process has great potential to be applied in various polymer industries.
Keywords: ultrasonic irradiation; phase transfer catalysis (PTC); polymerization; kinetics; multi-site phase transfer catalyst; bi-phase system ultrasonic irradiation; phase transfer catalysis (PTC); polymerization; kinetics; multi-site phase transfer catalyst; bi-phase system
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Vivekanand, P.A.; Wang, M.-L.; Hsieh, Y.-M. Sonolytic and Silent Polymerization of Methacrlyic Acid Butyl Ester Catalyzed by a New Onium Salt with bis-Active Sites in a Biphasic System — A Comparative Investigation. Molecules 2013, 18, 2419-2437.

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