Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 349530
Title Mild hydrolysis of 2-trifluoromethylphenol: Kinetics, mechanism and environmental relevance
Author(s) Reinscheid, U.M.; Vervoort, J.J.M.; Zuilhof, H.
Source Chemosphere 65 (2006)2. - ISSN 0045-6535 - p. 318 - 323.
Department(s) Biochemistry
Laboratory for Organic Chemistry
Publication type Refereed Article in a scientific journal
Publication year 2006
Keyword(s) trifluoromethyl group - organic-compounds - water-systems - degradation - density - molecules - exchange - behavior - models - diuron
Abstract 2-Trifluoromethylphenol was hydrolysed in a phosphate buffer at neutral pH. At mild temperatures ranging from 34 °C to 69 °C this compound liberates consecutively fluorine anions to form salicylic acid. This process is energetically driven by the hydration of the fluorine anions. No intermediates have been detected by HPLC and 19F-NMR and this was confirmed by computer calculations which favor the first step in the whole reaction sequence being rate-limiting. Accordingly, the reaction energy of the first dehalogenation of the trifluoromethyl anion is 28.4 kcal mol¿1 higher than for the second dehalogenation. The pseudo-first-order kinetic was determined and from an Arrhenius diagram an activation energy of Ea = 25.1 kcal mol¿1 has been estimated. At 37 °C and a pH of 7.4 the half-life was 6.9 h. The rate of hydrolysis was favored at higher pH and it was not influenced by oxygen, sunlight or trace elements found in natural water. The latter was shown by incubations with lake water instead of distilled water.
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