One-Pot Conversion of Epoxidized Soybean Oil (ESO) into Soy-Based Polyurethanes by MoCl₂O₂ Catalysis.

Vincenzo Pantone,Paola Fini,Antonella Russo,Angelo Nacci,Cosimo Annese,Lucia D’Accolti,Caterina Fusco

doi:10.3390/molecules22020333

Abstract

An innovative and eco-friendly one-pot synthesis of bio-based polyurethanes is proposed via the epoxy-ring opening of epoxidized soybean oil (ESO) with methanol, followed by the reaction of methoxy bio-polyols intermediates with 2,6-tolyl-diisocyanate (TDI). Both synthetic steps, methanolysis and polyurethane linkage formation, are promoted by a unique catalyst, molybdenum(VI) dichloride dioxide (MoCl2O2), which makes this procedure an efficient, cost-effective, and environmentally safer method amenable to industrial scale-up.

Highlights

In an era facing the depletion of fossil fuels and the increasing environmental concerns related to their burning, much of the current efforts have been directed to the challenging search for more sustainable sources that can ensure continuous manufacture of those commodities that have improved the quality of human life
2 O2 can efficiently catalyze the methanolysis of a range of terminal epoxides to carbamylation
MoCl2 O2, [10], as confirmed by the safety data given in databases of ECHA

Summary

Introduction

In an era facing the depletion of fossil fuels and the increasing environmental concerns related to their burning, much of the current efforts have been directed to the challenging search for more sustainable sources that can ensure continuous manufacture of those commodities that have improved the quality of human life. A practical approach to PU from vegetable oils involves epoxidation of the carbon-carbon double bonds of unsaturated fatty ester moieties and subsequent epoxide ring-opening reaction by nucleophilic reagents, providing the hydroxyl functionalities that form the urethane network upon reaction with isocyanates [3]. This is exemplified by the conversion of soybean oil (SO) into soy-based PU, through preliminary epoxidation, followed by methanolysis of the epoxidized oil (ESO), and reaction of the ensuing soy-methanol polyol 1 with suitable diisocyanates (Scheme 1)

Methods

Results

Conclusion