Study of the Effect of Temperature on the Reduction of Acetyldiphenyl with Aluminum Isopropoxide
Abstract Generated abstract
This study examines how temperature affects the reduction of acetyldiphenyl with aluminum isopropoxide in p-xylene, a reaction that yields both diphenylmethylcarbinol and the vinyl compound phenylstyrene. Experiments were conducted at 80, 100, and 120°C using a 1:1 ratio of ketone to reducing agent, with acetyldiphenyl and carbinol concentrations determined analytically and phenylstyrene estimated by difference. The results indicate that increasing temperature within the studied range increases the yield of phenylstyrene, probably due to enhanced dehydration of the intermediate carbinol.
Full Text
STUDY OF THE EFFECT OF TEMPERATURE ON THE PROCESS OF REDUCTION OF ACETYLDIPHENYL WITH ALUMINUM ISOPROPOXIDE
V. L. IVASENKO, E. E. SIROTKINA, V. P. LOPATINSKII
(Presented by the scientific-methodological seminar of the Faculty of Chemical Technology)
In studying the reduction of certain fatty-aromatic ketones with aluminum isopropoxide in a medium of aromatic hydrocarbons, the corresponding carbinols and vinyl compounds were obtained as final products. It was found that, with an increase in the electron density at the carbonyl group of the ketones, the yield of vinyl compounds increases [1]. For a more detailed study of the influence of various factors on the process of synthesis of vinyl compounds by the above-mentioned method, it was decided to investigate the process of reduction of acetyldiphenyl, since in the reduction of acetyldiphenyl with aluminum isopropoxide in a para-xylene medium, phenylstyrol and diphenylmethylcarbinol are obtained in approximately equal amounts [1]. The present communication gives the results of studies on the influence of temperature on the yield of phenylstyrol.
The reduction of acetyldiphenyl was carried out with freshly distilled aluminum isopropoxide; purified p-xylene, freed from sulfur compounds, was used as the solvent [2]. The reduction was carried out at temperatures of 80, 100, and 120°C, with a ratio of acetyldiphenyl to aluminum isopropoxide of 1:1. The reduction procedure is described in our previous communication [1]. The change in the concentration of acetyldiphenyl during the course of the reduction process was determined polarographically by the method developed by V. D. Bezuglyi [3]. The change in the concentration of carbinol during the process was determined by the method given in [4]. The concentration of phenylstyrol was determined by
Fig. 1. Effect of temperature on the yield of phenylstyrol.
—○— concentration of acetyldiphenyl;
—△— concentration of carbinol;
—×— concentration of phenylstyrol.
the difference between the amount of acetyldiphenyl and the amount of carbinol, since part of the phenylstyrene polymerizes during the reduction process. The results of the measurements performed are presented in Fig. 1.
From the data presented it is evident that, with increasing temperature, the yield of phenylstyrene increases, probably because, as the temperature rises, the rate of dehydration of the carbinol increases.
Conclusions
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The effect of temperature on the process of synthesizing phenylstyrene by reduction of acetyldiphenyl with aluminum isopropoxide in a p-xylene medium has been studied.
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It has been shown that, with increasing temperature in the investigated interval, the yield of the vinyl compound increases.
References
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V. L. Ivasenko, E. E. Sirotkina, V. P. Lopatinskii, V. P. Kozlova, V. T. Peremetina, V. D. Filimonov. Reduction of certain aromatic compounds with aluminum isopropoxide. Izv. TPI, vol. 185, 1970.
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A. Weisberger et al. Organic Solvents. IL, Moscow, 1958.
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V. D. Bezuglyi. Polarography in the Chemistry and Technology of Polymers. KhTU Publishing House, Kharkov, 1964.
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I. Houben-Weyl. Methods of Organic Chemistry, vol. II, Goskhimizdat, Moscow, 1963.