Microgels with Trialkylmmoio Side-Chains Function as CAtalysts for the Alkaline-Hydrolysis of Substituted Phenyl Luarte Esters

Evans, David J. and Williams, Andrew and Pryce, R.J. (1995) Microgels with Trialkylmmoio Side-Chains Function as CAtalysts for the Alkaline-Hydrolysis of Substituted Phenyl Luarte Esters. Journal of Molecular Catalysis A: Chemical, 99 (1). pp. 41-46. ISSN 1381-1169. (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

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Official URL
http://dx.doi.org/10.1016/1381-1169(95)00010-0

Abstract

Microgels incorporating 2-(tetradecyldimethylammonio)ethyl methacrylate bromide have been prepared by emulsion polymerisation with methyl methacrylate, 2-ethoxyethyl methacrylate and ethylene glycol dimethacrylate in the molar ratio 0.15:0.45:0.30:0.10 respectively. The microgel solubilises aryl laurate esters in aqueous solution and catalyses the alkaline hydrolysis of these esters; the variation of rate constant with microgel concentration indicates a complexation phenomenon with the 4-nitrophenyl ester. The reactivity of the microgel sol with the laurate esters is similar to that of the analogous micellar system from cetyltrimethylammonium bromide (CTAB) described by Al-Awadi and Williams (J. Org. Chem., 55 (1990) 2001). The rate constant for the microgel-catalysed reaction of hydroxide ion with the substituted phenyl laurate esters obeys the Bronsted correlation: logk(OH)(cat)=-0.53pK(a)+4.49 The value of the Bronsted beta(lg) (-0.53) is similar to that observed for CTAB-catalysis and for uncatalysed alkaline hydrolysis; it indicates that the catalytic site of ester hydrolysis resides in an aqueous-like region of the microgel.

Item Type: Article
Uncontrolled keywords: Alkaline Hydrolysis; Cationic Surfactant; Microgels; Phenyl Eaters; Polsoap
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > School of Engineering and Digital Arts
Depositing User: P. Ogbuji
Date Deposited: 02 Jun 2009 11:43
Last Modified: 16 Jul 2014 14:14
Resource URI: https://kar.kent.ac.uk/id/eprint/19515 (The current URI for this page, for reference purposes)
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