Production of 1,6-hexanediol from tetrahydropyran-2-methanol by dehydration–hydration and hydrogenation
Samuel P. Burt, et al.
Green Chem., 2017,19, 1390-1398.
1,6-Hexanediol (1,6-HDO) is an important building block chemical used in the synthesis of specialty chemicals and various polymers. The biomass-derived feedstock tetrahydropyran-2-methanol (THP2M) can be converted to 1, 6-HDO. However, the high cost of catalysts and low productivity limit the industrial application of these systems. This study introduces an alternative to traditional Pt, Rh, and Ir-based catalysts for the conversion of THP2M to 1,6-HDO.
This work presents a catalytic system for a renewable pathway to 1,6-HDO with a three-step synthesis of 1,6-HDO from THP2M via THO. Concrete synthetic routes include:
> THP2M dehydration: THP2M is dehydrated over an aluminosilicate catalyst in a continuous flow gas phase reactor to produce 2,3,4,5-tetrahydroheptidine (THO).
> THO hydration: THO is hydrated to 6-hydroxyhexanal (6HDHX) and 2-oxepanol (OXL) in 85% yield without using any catalyst.
> Hydrogenation to 1,6-HDO: 6HDHX and OXL are almost quantitatively hydrogenated to 1,6-HDO with Ru/C or Ni/C.
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