The isobutylene-isobutane alkylation process in liquid HF revisited

PETR 164

Bruno A. C. Horta, bruno@iq.ufrj.br1, Ricardo Bicca Alencastro1, Carolina L. Araújo1, Alejandro Ramiréz-Solís2, Luis J. Alvarez3, Claudio M. Zicovich-Wilson4, and Pierre M. Esteves, pesteves@iq.ufrj.br1. (1) Physical Chemistry Group, Universidade Federal do Rio de Janeiro, Instituto de Química, Cidade Universitária CT Bloco A, Rio de Janeiro, Brazil, (2) Laboratoire de Physique Quantique, IRSAMC, Université Paul Sabatier, Université Paul Sabatier, 31062, Toulouse, France, (3) Depto. de Física, UniVersidad Auto´noma del Estado de Morelos, Facultad de Ciencias, Av Universidad 1001, CuernaVaca, Morelos. 62210, Mexico, (4) Instituto de Matemáticas, Universidad Nacional Autónoma de México, AV. UniVersidad s/n, 62210 CuernaVaca, Morelos, Mexico
Details on the mechanism of HF catalyzed isobutylene-isobutane alkylation were investigated. On the basis of available experimental data and high-level quantum chemical calculations, a detailed reaction mechanism is proposed taking into account solvation effects of the medium. We explain why the density of the liquid media and stirring rates are the most important parameters to achieve maximum yield of alkylate, in agreement with experimental findings. The ab initio Car-Parrinello molecular dynamics calculations show that isobutylene is irreversibly protonated in the liquid HF medium at higher densities, leading to the ion pair formation, which is shown to be a minimum on the potential energy surface after optimization using periodic boundary conditions. The HF medium solvates preferentially the fluoride anion. On the other hand, the tert-butyl cation is weakly solvated, where the closest HF molecules appear at a distance of about 2.9 Å with the fluorine termination of an HF chain.