SCeLiO-4B: Sugars, Cellulose and Lignin upscaling towards biobased building blocks

Project

SCeLiO-4B: Sugars, Cellulose and Lignin upscaling towards biobased building blocks

Development of biobased aromatic chemicals is of eminent importance in order to green chemical industry. It offers unrivalled opportunities to the agrifood- and biomass processing industry. Currently, over forty percent of the chemicals and materials produced in the industries are based on aromatic building blocks like terephthalic acid, phenols or styrene. These building blocks are being used vastly in the construction of well-known consumer materials like PET based packaging materials, ABS based lego bricks and drinking bottles.

Another group of aromatic chemicals such as (methyl)phthalic acid, orthophthalic acid, cresols, substituted phenols, tri-or hemimellitic acid are receiving rising market interest as some of them are worldwide consumed by several million tonnes per year. Aromatic building blocks are being used in applications like resins for decorative and industrial coatings, specialty lubricants and plasticisers or as co-monomers for construction or packaging materials.

Project goal

In this project, Wageningen Food & Biobased Research (and partners) develop efficient and cost-effective routes for the production of biomass derived maleic acid anhydride or other potential dienophiles suitable for producing biobased aromatic chemicals.

Tailor-made aromatic compounds

Recently, we established an attractive route to develop a generic technology for the production of such bulk chemicals. The production route is focused on either ‘drop-in’ or ‘near drop-in’ aromatic chemicals from biomass that will enable replacement by biobased equivalents. We are using our expertise in organic chemistry and homogenous and heterogeneous catalysis in order to establish the desired routes.

The strategy involves either one-step or two-steps with the use of a Diels-Alder (DA) addition reaction between a biomass-derived furanic diene and an appropriate dienophile. This gives an oxabicyclo adduct that can, in principle, be directly or subsequently dehydrated to the desired aromatic compound. By choosing the appropriate choice of starting diene and dienophile, a tailor-made multifunctional aromatic compound (suitable for specific applications) can be obtained. The best examples of dienes include (substituted) furans and 5-hydroxymethylfurfuran (5-HMF); and for dienophiles, maleic acid anhydride and acrylic acid ester.

Publicaties

Substituted phthalic anhydrides from biobased furanics: A new approach to renewable aromatics
Shanmugam Thiyagarajan, H. Genuino, J. K. van der Waal, E. d. Jong, D.S. van Es, B.M. Weckhuysen, P.C. A. Bruijnincx, J. van Haveren
ChemSusChem
., 8, 3052-3056, 2015

A Facile Solid-Phase Route to Renewable Aromatic Chemicals from Biobased Furanics
Shanmugam Thiyagarajan, H. Genuino, J. K. van der Waal, E. d. Jong, D.S. van Es, B.M. Weckhuysen, P.C. A. Bruijnincx, J. van Haveren
Angew. Chem. Int. Ed.
, 55, 1368-1371, 2016