title: Shape-selective Valorization of Biomass-derived Glycolaldehyde using Tin-containing Zeolites.
abstract: A highly selective self-condensation of glycolaldehyde to different C4molecules has been achieved using Lewis acidic stannosilicate catalysts in water at moderate temperatures (40-100 °C). The medium-sized zeolite pores (10-membered ring framework) in Sn-MFI facilitate the formation of tetrose sugars while hindering consecutive aldol reactions leading to hexose sugars. High yields of tetrose sugars (74 %) with minor amounts of vinyl glycolic acid (VGA), an α-hydroxyacid, are obtained using Sn-MFI with selectivities towards C4products reaching 97 %. Tin catalysts having large pores or no pore structure (Sn-Beta, Sn-MCM-41, Sn-SBA-15, tin chloride) led to lower selectivities for C4sugars due to formation of hexose sugars. In the case of Sn-Beta, VGA is the main product (30 %), illustrating differences in selectivity of the Sn sites in the different frameworks. Under optimized conditions, GA can undergo further conversion, leading to yields of up to 44 % of VGA using Sn-MFI in water. The use of Sn-MFI offers multiple possibilities for valorization of biomass-derived GA in water under mild conditions selectively producing C4molecules.
authors: Department of Chemistry, Technical University of Denmark, Kemitorvet, 2800-, Kgs. Lyngby, Denmark.|New Business R&D, Haldor Topsøe A/S, Haldor Topsøes Allé 1, 2800-, Kgs. Lyngby, Denmark.
authors: Søren
authors: http://orcid.org/0000-0001-8080-3599
authors: S
authors: Tolborg
authors: Department of Chemistry, Technical University of Denmark, Kemitorvet, 2800-, Kgs. Lyngby, Denmark.
authors: Sebastian
authors: http://orcid.org/0000-0003-3761-3217
authors: S
authors: Meier
authors: Department of Chemistry, Technical University of Denmark, Kemitorvet, 2800-, Kgs. Lyngby, Denmark.|Center of Innovative and Applied Bioprocessing (CIAB), Mohali, 160071-, Punjab, India.
authors: Shunmugavel
authors: http://orcid.org/0000-0002-8428-1895
authors: S
authors: Saravanamurugan
authors: Department of Chemistry, Technical University of Denmark, Kemitorvet, 2800-, Kgs. Lyngby, Denmark.
authors: Peter
authors: http://orcid.org/0000-0001-7175-3796
authors: P
authors: Fristrup
authors: New Business R&D, Haldor Topsøe A/S, Haldor Topsøes Allé 1, 2800-, Kgs. Lyngby, Denmark.
authors: Esben
authors: E
authors: Taarning
authors: New Business R&D, Haldor Topsøe A/S, Haldor Topsøes Allé 1, 2800-, Kgs. Lyngby, Denmark.
authors: Irantzu
authors: http://orcid.org/0000-0001-6997-7491
authors: I
authors: Sádaba
mesh_terms: D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D018533:Biomass; D002384:Catalysis; D006601:Hexoses / Q000138:chemical synthesis; D058116:Lewis Acids; D013780:Tetroses / Q000138:chemical synthesis; D014001:Tin; D017641:Zeolites / Q000737:chemistry*
chemical_list: D006601:Hexoses; D058116:Lewis Acids; D013780:Tetroses; D017641:Zeolites; D014001:Tin; D000079:Acetaldehyde; C010972:glycolaldehyde
keywords: aldol condensation; biomass conversion; tetrose sugars; tin; zeolites