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Production of Hexane-1,2,5,6-tetrol from Biorenewable Levoglucosanol over Pt-WOx/TiO2

We have investigated the synthesis of hexane-1,2,5,6-tetrol (hereafter "tetrol") from aqueous solutions of biomass-derived levoglucosanol (hereafter "Lgol") using a (10 wt %)Pt-(10 wt %)WOx/TiO2 catalyst in both batch and continuous flow reactors. The tetrol selectivity was over 90% with Lgol feed concentrations of 10-30 wt %. Most of the Lgol feed stereochemistry was preserved (notably 91%), with threo-Lgol (hereafter "t-Lgol") and erythro-Lgol (hereafter "e-Lgol") converting to (S,S)-tetrol and (S,R)-tetrol, respectively. The rate of Lgol conversion was found to be first-order in the Lgol concentration, suggesting that the catalyst surface is not saturated with Lgol. The measured reaction order for H2 was zero, which is consistent with either a mechanism involving acid-catalyzed irreversible C-O bond cleavage of Lgol followed by metal-catalyzed hydrogenation of reactive intermediates or one where all of the metal sites are saturated with H2. When the reaction was run in a continuous flow reactor, the catalyst exhibited deactivation with increasing time-on-stream but was found partially regenerable with a consecutive calcination and reduction treatment. Deactivation was concluded to be caused mainly by carbon deposition, with some W-leaching from the catalyst in the initial stages of reaction. The here demonstrated understanding of reaction kinetics and catalyst stability could facilitate the development of improved processes to produce hexane-1,2,5,6-tetrol from biomass.
- University of Graz Austria
- Ave Maria University United States
- Chinese Academy of Sciences China (People's Republic of)
- University of Wisconsin–Oshkosh United States
- Utrecht University Netherlands
lgol followed, reaction orders, General Chemical Engineering, lgol feed concentrations, lgol ”), Biochemistry, lgol feed stereochemistry, sub ><, Taverne, derived levoglucosanol, improved processes, Ecology, lgol ”) converting, lgol conversion, x </, bond cleavage, mechanism involving acid, Infectious Diseases, bifunctional acid-metal solid catalysts, 2 </ sub, reaction kinetics, hereafter “, notably 91 %), found partially regenerable, stereochemistry preservation, reduction treatment, caused mainly, aqueous solutions, lgol concentration, Chemical Sciences not elsewhere classified, hereafter “ e, Information Systems not elsewhere classified, reactive intermediates, scalable processes, catalyst surface, polymer precursors, Environmental Chemistry, catalyst stability, SDG 7 - Affordable and Clean Energy, levoglucosenone and derivates, 660, Renewable Energy, Sustainability and the Environment, biorenewable levoglucosanol, Computational Biology, continuous flow reactor, General Chemistry, continuous flow reactors, carbon deposition, r </, initial stages, catalyzed hydrogenation, increasing time, measured reaction order, activation energy, catalyst exhibited deactivation, consecutive calcination, biomass conversion, demonstrated understanding
lgol followed, reaction orders, General Chemical Engineering, lgol feed concentrations, lgol ”), Biochemistry, lgol feed stereochemistry, sub ><, Taverne, derived levoglucosanol, improved processes, Ecology, lgol ”) converting, lgol conversion, x </, bond cleavage, mechanism involving acid, Infectious Diseases, bifunctional acid-metal solid catalysts, 2 </ sub, reaction kinetics, hereafter “, notably 91 %), found partially regenerable, stereochemistry preservation, reduction treatment, caused mainly, aqueous solutions, lgol concentration, Chemical Sciences not elsewhere classified, hereafter “ e, Information Systems not elsewhere classified, reactive intermediates, scalable processes, catalyst surface, polymer precursors, Environmental Chemistry, catalyst stability, SDG 7 - Affordable and Clean Energy, levoglucosenone and derivates, 660, Renewable Energy, Sustainability and the Environment, biorenewable levoglucosanol, Computational Biology, continuous flow reactor, General Chemistry, continuous flow reactors, carbon deposition, r </, initial stages, catalyzed hydrogenation, increasing time, measured reaction order, activation energy, catalyst exhibited deactivation, consecutive calcination, biomass conversion, demonstrated understanding
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