A theoretical determination of the composition of by-products obtained in the production of butylated hydroxytoluene from 2,6-di-tert-butylphenol

Abstract

The hydrogenolysis of N,N-dimethyl(3,5-di-tert-butyl-4-hydroxybenzyl)amine, which leads to butylated hydroxytoluene (BHT) as the main product, has been investigated by the density functional theory (DFT) method with the BPE functional and the SVP basis set. A set of valid reaction paths was determined from both thermodynamic and kinetic points of view. Possible products of the reaction were identified, it was shown that the most probable by-product is 4,4′-ethylenebis(2,6-di-tert-butylphenol). The standard gas-phase enthalpies of formation of some possible products of the reaction have been predicted by using the BPE/SVP approach, coupled with isodesmic reactions.