Valorization of the Exoskeletons of Crustaceans in Seafood Wastes to Chemicals in Renewable Solvents : A Catalytic and Mechanistic Study

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Detail(s)

Original languageEnglish
Pages (from-to)15350–15363
Journal / PublicationACS Sustainable Chemistry and Engineering
Volume11
Issue number42
Online published10 Oct 2023
Publication statusPublished - 23 Oct 2023

Abstract

Levulinic acid (LA) and γ-valerolactone (GVL) are considered valuable platform chemicals that can be derived from various types of biomass ranging from food wastes to agricultural residues. Herein, the valorization of the exoskeletons of crustaceans in seafood wastes into LA, GVL, acetic acid (AA), and ammonium (NH4)+ was studied including the catalytic and mechanistic aspects. Chitin was used as a model compound to optimize the conditions for converting the exoskeletons of crustaceans in seafood wastes using acetic acid (AA) and GVL as bio-originated renewable solvents. The same conditions were applied to convert various pretreated seafood wastes, such as the exoskeletons of crabs and lobsters. The decalcification of the crustacean samples using phosphoric acid was also studied. GVL was also used as a solvent to produce formic acid (FA), LA, NH4+, and GVL to simplify the product purification process. The reaction mixture of chitin (0.41 g, equivalent to 2 mmol of N-acetyl-glucosamine) in a mixture of 10 mL of GVL and 1.5 mL of 5 M H2SO4 was heated at 150 °C for 4 h followed by neutralization with additional NH4+ (NH4OH) to result in two phases due to the salting out effect of (NH4)2SO4. Ru-based Shvo’s catalyst was then added to the organic phase for transfer hydrogenation of LA with FA as the hydrogen donor to yield GVL. Uniformly labeled N-acetyl-[13C6]glucosamine (UL-13C6-NAG) was used to confirm the formation of 13C5-GVL in 12C5-GVL via 13C5-LA and 13C-FA. Detailed in situ NMR studies revealed the presence of two bicyclic compounds, protonated salt of 1,6-anhydro-2-deoxy-2-ammonio-glucopyranose (AGluNPH+) and 1,6-anhydro-2-deoxy-2-ammonio-glucofuranose (AGluNFH+), as proposed key intermediates of the of UL-13C6-NAG conversion. © 2023 The Authors. Published by American Chemical Society.

Research Area(s)

  • biomass conversion, levulinic acid, reaction mechanism, renewable solvents, waste valorization, γ-valerolactone

Citation Format(s)

Valorization of the Exoskeletons of Crustaceans in Seafood Wastes to Chemicals in Renewable Solvents: A Catalytic and Mechanistic Study. / Horváth, István T.; Wong, Claire Yuet Yan; Choi, Alex Wing-Tat et al.
In: ACS Sustainable Chemistry and Engineering, Vol. 11, No. 42, 23.10.2023, p. 15350–15363.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review