Phosphorus, Sulfur, and Silicon, 185:832–837, 2010
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500903002537
MONITORING THE PHOSPHORYLATION OF PHENOL
WITH DIETHYL CHLOROPHOSPHATE IN AQUEOUS
MEDIUM IN THE PRESENCE OF SODIUM HYDROXIDE
BY IN SITU FOURIER TRANSFORM INFRARED
SPECTROSCOPY
Gyo¨rgy Keglevich,1 Re´ka Eszter Puska´s,1 Alajos Gru¨n,1,2
and Istva´n Csontos1
1Department of Organic Chemistry and Technology, Budapest University
of Technology and Economics, Budapest, Hungary
2Research Group of the Hungarian Academy of Sciences at the Department
of Organic Chemistry and Technology, Budapest University of Technology
and Economics, Budapest, Hungary
In situ Fourier transform IR spectroscopy has been found to be an appropriate tool for
monitoring the title reaction resulting in the formation of diethyl phenylphosphate.
Keywords Heterogeneous phase; in situ Fourier transform IR spectroscopy; monitoring;
phenol; phosphorylation
INTRODUCTION
In situ Fourier transform (FT) IR spectroscopy is a current method for monitoring or-
ganic chemical transformations.1–8 The time-dependent IR spectra allow the establishment
of formal kinetics, detection of intermediates, and optimization of the reaction investigated.
Hence, in situ FT-IR spectroscopy is a useful tool in environmentally friendly chemistry.
No matter if the reaction mixtures are homogeneous or heterogeneous, they can be studied
by the ReactIR 1000 spectrometer supplied with an attenuated total reflection (ATR) probe
in the range of –80 to 250◦C, even under pressure. In situ FT-IR spectroscopy is becoming a
routine method in the pharmaceutical and fine chemical, and even in the plastics industries.
In earlier studies, esterifications6 and oximation reactions7,8 were investigated. On the one
hand, a formal equilibrium constant was determined,6 while on the other hand, interme-
diates were pointed out under suitable reaction conditions.7,8 The reactions were, in all
cases, optimized. In situ FT-IR spectroscopy has been applied only rarely in organophos-
phorus chemistry.5 We decided to monitor an esterification involving a Schotten–Baumann
phosphorylation of phenol. This type of reaction is important in the industrial synthesis of
organophosphorus insecticides.9,10
Received 20 March 2009; accepted 27 April 2009.
The authors are grateful for the OTKA (T067679) support of this work.
Address correspondence to Gyo¨rgy Keglevich, Department of Organic Chemistry and Technology, Budapest
University of Technology and Economics, H-1521 Budapest, Hungary. E-mail: keglevich@mail.bme.hu
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