Solid-phase hydrohalogenation of 2-methyl-2-butene

Complex formation between 2-methyl-2-butene and hydrogen halides (HX, X=Cl, Br) and the hydrohalogenation reaction was studied in the solid phase in the range of 80–150°K by IR spectroscopy. It was shown that 2-methyl-2-butene forms 11 and 12 complexes with HX. The hydrohalogenation reaction is realized by rearrangement of the 12 complex into a complex of the hydrohalogenation product with HX. The kinetics of the transformation depend on the ratio of the reagents. With an excess of the olefin the reaction is described by a kinetic equation of first order with respect to the complex of the initial reagents up to 60–80% conversion; with an excess of HX it is described by an equation of polychronous kinetics. The effective activation energy of the solid-phase halogenation of 2-methyl-2-butene is not greater than 20 kJ/mole. A molecular mechanism of addition to olefins in the solid phase is examined.Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 23, No. 1, pp. 34–40, January–February, 1987.