Mechanism of Catalytic Alkylation of 2,6-di-tert-Butylphenol by Methyl Acrylate

Alexander Volod´kin and Gennady Zaikov
N. M. Emanuel Institute of Biochemical Physics Russian Academy of Sciences 4, Kosygin str., 119334 Moscow, Russia;
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The determining factor of the reaction of 2,6-di-tert-butylphenol with alkaline metal hydroxides is temperature, depending on which two types of potassium or sodium 2,6-di-tert-butyl phenoxides are formed with different catalytic activity in the alkylation of 2,6-di-tert-butylphenol with methyl acrylate. More active forms of 2,6-But2C6H3OK or 2,6-But2C6H3ONa are synthesized at temperatures higher than 433 K and represent predominantly monomers of 2,6-di-tert-butyl phenoxides producing dimers on cooling.

[1] Volod'kin A., Paramonov V., Egidis F. and Popov L.: Chem. Ind., 1988, 12, 7.

[2] Volod'kin A., Zaitsev A., Rubailo V. et al.: Polym. Degrad. Stab., 1989, 26, 69.

[3] Prokof'ev A., Solodovnikov S., Volod'kin A. and Erschov V.: Izv. Akad. Nauk SSSR, Ser.Chim., 1972, 640.

[4] Volod'kin A. and Zaikov G.: Ross. Khim. Zh., 2000, 44, 81.

[5] Volod'kin A. and Zaikov G.: Rus. Chem. Bull., Int. Edn., 2002, 51, 2189.

[6] Becker G.: Einfuhrung in die Elektronentheorie organischemischer Reaktionen. Deutscher Verlag der Wissenschaften, Berlin 1974.