PhD ceremony Mr. Teddy: Caprolactam from renewable resources: catalytic conversion of 5-hydroxymethylfurfural into caprolactone

PhD ceremony: Mr. Teddy, 16.15 uur, Academiegebouw, Broerstraat 5, Groningen

Dissertation: Caprolactam from renewable resources: catalytic conversion of 5-hydroxymethylfurfural into caprolactone

Promotor(s): prof. H.J. Heeres, prof. J.G. de Vries

Faculty: Mathematics and Natural Sciences

C6-sugars in lignocellulosic biomass are interesting precursors for a broad range of chemicals with high application potential. An example is 5-hydroxymethylfurfural (HMF). It can be prepared in high yields from D-fructose, and potentially also from other cheaper resources (D-glucose).

In this thesis, experimental studies on the conversion of HMF into caprolactam, the monomer for nylon-6, a widely used synthetic polymer, are described.

A major breakthrough in this research involved the development of catalytic technology for the conversion of HMF to 1,6-hexanediol (1,6-HD). Four different routes were explored involving catalytic hydrogenation and hydrodeoxygenation reactions with various homogeneous and heterogeneous catalysts: i) The direct hydrogenation of HMF to 1,6-HD; ii) a two-step sequence via 2,5-THF-dimethanol (THFDM); iii) a three-step synthesis via THFDM and 1,2,6-hexanetriol (1,2,6-HT); and iv) a four-step synthesis via THFDM, 1,2,6-HT, and tetrahydro-2H-pyran-2-ylmethanol (2-THPM)