Boron Based Catalysts for Cycloaddition Reactions

Executive Summary

Increasing there is greater interest in replacing petroleum based chemicals with bio-based alternatives. The packaging market in particular, has actively sought “greener” alternatives for important materials such as poly(ethylene terephthalate), a.k.a. PET. MSU researchers have developed a new catalyst and method to make cycloaddition products at high yields while avoiding deleterious side reactions. The process allows the efficiency conversion of biobased materials to important starting monomers used in the production of PET, thus enables 100% biobased polymer.


Description of the Technology

This invention is a high yielding Diels-Alder reaction of unesterified acrylic acids with various dienes using boron based catalysts. The reactions can be carried out in bulk or low solvent concentrations. As demonstrated, biobased acrylic acid could be reacted with biobased isoprene to yield up to 96% of para cycloadduct. The adducts could then be aromatized and oxidized to form terephthalic acid, isophthalic acid or mixtures, which in turn can be polymerized with ethylene glycol to form bio-based PET.



  • Solvent free, room temperature reaction
  • High yields
  • No competing olefin polymerization



  • Synthesis of bio-based terephthalic acid, isophthalic acid, poly(ethylene terephthalate)
  • Biobased packaging
  • Polyester from 100% renewable materials


Patent Status

Issued US Patent 10,858,318B2, Brazilian Patent BR112018006004-6, Others pending


Licensing Rights

Licensing Rights Available in the Non Beverage Field



ACS Sustainable Chemistry and Engineering Paper, 2015



Dr. John Frost, Dr. Peng Zhang




Patent Information:


For Information, Contact:

Jon Debling
Technology Manager
Michigan State University
John Frost
Peng Zhang