We report the catalytic conversion of 5-hydroxymethylfurfural(HMF) to monomers fornylon-6,6 production, which include adipic acid and hexamethylenediamine. Ithas been shown previously that 1,2,6-hexanetriol can be obtained in high yieldsfrom HMF. Selective dehydration of 1,2,6-hexanetriol to produce 1,6-hexanediolwas performed over 1wt% Pt supported on various acidic metal oxides(e.g., amorphous silica-alumina,Y-zeolite, H-ZSM5, amorphous niobia). Selective oxidation of 1,6-hexanediolwith molecular dioxygen catalyzed by 1wt% Au/C with added base and 3wt% Pt/TiO2with added acid have been carried out, resulting in adipic acid yield of 97mol%and 89mol% , respectively. Additionally, 1,6-hexanediol can undergo oxidativeamination to form adiponitrile in yields greater than 80mol% by a homogeneousiodine-containing organic molecule as oxidant and ammonia as nitrogen source inaqueous media . Subsequently, adiponitrile can be hydrogenated over Raneynickel catalyst to hexamethylenediamine in close to quantitative yields. Thisintegrated reaction pathway of nylon monomers production from renewablebiomass-derived platform chemical HMF represents an attractive alternative totheir petroleum derived counterparts.

Renewable production of nylon-6,6 monomers from biomass-derived 5-hydroxymethylfurfural(HMF)

247th National Meeting (2014)

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