Fully recyclable Brønsted acid catalyst systems

Abstract

Homogeneous and heterogeneous sulfonic acid catalysts are some of the most common catalysts used in organic chemistry. This work explores an alternative scheme using a fully recyclable polymeric solvent (a poly-α-olefin (PAO)) and soluble PAO-anchored polyisobutylene (PIB)-bound sulfonic acid catalysts. This PAO solvent is nonvolatile and helps to exclude water by its nonpolar nature which in turn drives reactions without the need for distillation of water, avoiding the need for excess reagents. This highly nonpolar solvent system uses polyisobutylene (PIB) bound sulfonic acid catalysts that are phase-anchored in solvents like PAO. The effectivenes of these catalysts was demonstrated by their use in esterifications, acetalizations, and multicomponent condensations. These catalysts and the PAO solvent phase show excellent recyclability in schemes where products are efficiently separated. For example, this non-volatile polymeric solvent and the PIB-bound catalyst can be recycled quantitatively when volatile products are separated and purified by distillation. In other cases, product purification can be effected by product self-separation or by extraction.