A study was made of the composition of the alkylate obtained with alkylation of phenol using the 240–320°C fraction of α-olefins of normal structure, in the presence of an alumosilicate catalyst, using a combination of the methods of rectification, adsorption separation of the fractions obtained, and study of the fractions by adsorption separation using IR spectrometry; the monoalkylphenol fraction was investigated by nuclear magnetic resonance.
The investigations clarified certain questions with respect to the mechanism of the main and side reactions taking place during alkylation. It was established that, during the alkylation process, there are formed secondary isomeric alkylphenols, predominantly o-alkylphenols. There is practically no structural isomerization, or destructive decomposition of α-olefins or of the alkyl chains of alkylphenols; there is, however, a migration of the double bond in the molecules of α-olefins, accompanied by the formation of cis and trans isomers. Polymerization of the olefins takes place only to a slight degree.
To decrease the yields of dialkylphenols, it is expedient to increase the phenol: olefins molar ratio.
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Potolovskii, L.A., Vasil'eva, V.N., Kirsanova, T.I. et al. Investigation of the composition of an alkylate obtained in the alkylation of phenol with high-molecular α-olefins of normal structure. Chem Technol Fuels Oils 6, 837–840 (1970). https://doi.org/10.1007/BF00717686
- Nuclear Magnetic Resonance
- Double Bond