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Chemical-Switching Strategy for Synthesis and Controlled Release of Norcantharimides from a Biomass-Derived Chemical.

ABSTRACT: Catalytic strategies were developed to synthesize and release chemicals for applications in fine chemicals, such as drugs and polymers, from a biomass-derived chemical, 5-hydroxymethyl furfural (HMF). The combination of the diene and aldehyde functionalities in HMF enabled catalytic production of acetalized HMF derivatives with diol or epoxy reactants to allow reversible synthesis of norcantharimide derivatives upon Diels-Alder reaction with maleimides. Reverse-conversion of the acetal group to an aldehyde yielded mismatches of the molecular orbitals in norcantharimides to trigger retro Diels-Alder reaction at ambient temperatures and released reactants from the coupled molecules under acidic conditions. These strategies provide for the facile synthesis and controlled release of high-value chemicals.

SUBMITTER: Chang H

PROVIDER: S-EPMC8014990 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Chemical-Switching Strategy for Synthesis and Controlled Release of Norcantharimides from a Biomass-Derived Chemical.

Chang Hochan H Huber George W GW Dumesic James A JA

ChemSusChem 20200825 19

Catalytic strategies were developed to synthesize and release chemicals for applications in fine chemicals, such as drugs and polymers, from a biomass-derived chemical, 5-hydroxymethyl furfural (HMF). The combination of the diene and aldehyde functionalities in HMF enabled catalytic production of acetalized HMF derivatives with diol or epoxy reactants to allow reversible synthesis of norcantharimide derivatives upon Diels-Alder reaction with maleimides. Reverse-conversion of the acetal group to ...[more]

PMID: 32964595

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Project description:The synthesis of magnetic iron-carbon composites (Fe/C) from waste avocado seeds via hydrothermal carbonization (HTC) has been demonstrated for the first time. These materials are shown to be effective in adsorption and catalytic applications, with performances comparable to or higher than materials produced through conventional processing routes. Avocado seeds have been processed in high-temperature water (230 °C) at elevated pressure (30 bar at room temperature) in the presence of iron nitrate and iron sulfate, in a process mimicking natural coalification. Characterization of the synthesized material has been carried out by X-ray diffraction (XRD), atomic absorption spectroscopy (AAS), X-ray fluorescence (XRF), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma-optical emission spectrometry (ICP-OES), Fourier-transform infrared spectroscopy (FT-IR), magnetometry, and through surface area measurements. The supported iron particles are observed to be predominately magnetite, with an oxidized hematite surface region. The presence of iron catalyzes the formation of an extended, ordered polymeric structure in the avocado seed-derived carbon. The magnetic Fe/C has been demonstrated as an adsorbent for environmental wastewater treatment using methylene blue and indigo carmine. Kinetic analysis suggests that the adsorbates are chemisorbed, with the positive surface charge of Fe/C being preferential for indigo carmine adsorption (49 mg g-1). Additionally, Fe/C has been evaluated as a heterogeneous catalyst for the hydroalkoxylation of phenylacetylene with ethylene glycol to 2-benzyl-1,3-dioxolane. Product yields of 45% are obtained, with 100% regioselectivity to the formed isomer. The solid catalyst has the advantages of being prepared from a waste material and of easy removal after reaction via magnetic separation. These developments provide opportunities to produce carbon-based materials for a variety of high-value applications, potentially also including energy storage and biopharmaceuticals, from a wide range of lignocellulosic biomass feedstocks.

Dataset Information

Chemical-Switching Strategy for Synthesis and Controlled Release of Norcantharimides from a Biomass-Derived Chemical.

Publications

Chemical-Switching Strategy for Synthesis and Controlled Release of Norcantharimides from a Biomass-Derived Chemical.

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