University of Delaware OEIP
University of Delaware

More Selective, Safer and Cheaper Synthesis of 4,4’-Dimethylbiphenyl

Technology #ud20-23

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Application:

This innovating technology pertains to a process that produces 4,4’-dimethylbiphenyl using a biomass derived intermediate, 5,5’-dimethylbifuran in high yield and selectivity. 4,4’-Dimethylbiphenyl can be used to produce diacids, diols, diamines and other compounds. Furthermore, 4,4’-biphenylcarboxylic acid can improve physical and barrier properties of polyesters such as PET and it can be used as a plasticizer for PVC.  This diacid also polymerizes with glycol to form copolymers with high tensile strength. 4,4’-Dimethylbiphenyl is a highly versatile compound that is a building block of many chemicals.

Problem Addressed:

The proposed processes for production of 4,4’-Dimethylbiphenyl are expensive and unsustainable. They rely on petrochemicals, toluene and benzene, as feedstocks. This novel process is environmentally safe and its production pathway is very selective. In this new process, dimethylbifuran is synthesized using furfural as the starting reagent. A very good and inexpensive catalyst has been identified, that produces the desired dimethylbiphenyl at low temperatures and moderate pressures. The petrochemical-based process is unselective to the desired product, requires large recycling streams and separation units, increasing both capital investment and production costs. In the new process, no by-products are formed using suitable catalysts and reaction conditions.

Benefits:

·  Dimethylbifuran[main reagent] synthesized from biomass-derived molecules

·  Overall simpler and sustainable alternative

·  Highly selective production process—no byproducts other than water

·  Efficient and inexpensive catalyst identified

Technology Summary:

Dimethylbifuran undergoes two Diels-Alder reactions with ethylene followed by dehydration. The tandem reactions are conducted at high pressure and moderate temperature with a specific catalyst to allow for higher yield. Product crystallizes in high purity. This production pathway offers more sustainable and environmentally friendly alternative to currently proposed processes.

PATENT STATUS: The technology is patent pending. Further information on licensing opportunities is available on request.