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Evaluating Possible Formation Mechanisms of Criegee Intermediates during the Heterogeneous Autoxidation of Squalene.
Environ Sci Technol
July 2024
Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, United States.
Organic molecules in the environment oxidatively degrade by a variety of free radical, microbial, and biogeochemical pathways. A significant pathway is heterogeneous autoxidation, in which degradation occurs via a network of carbon and oxygen centered free radicals. Recently, we found evidence for a new heterogeneous autoxidation mechanism of squalene that is initiated by hydroxyl (OH) radical addition to a carbon-carbon double bond and apparently propagated through pathways involving Criegee Intermediates (CI) produced from β-hydroxy peroxy radicals (β-OH-RO•).
View Article and Find Full Text PDFCatalytic carbon-carbon bond cleavage in lignin via manganese-zirconium-mediated autoxidation.
Nat Commun
January 2024
Renewable Resources and Enabling Sciences Center, National Renewable Energy Laboratory, Golden, CO, 80401, USA.
Efforts to produce aromatic monomers through catalytic lignin depolymerization have historically focused on aryl-ether bond cleavage. A large fraction of aromatic monomers in lignin, however, are linked by various carbon-carbon (C-C) bonds that are more challenging to cleave and limit the yields of aromatic monomers from lignin depolymerization. Here, we report a catalytic autoxidation method to cleave C-C bonds in lignin-derived dimers and oligomers from pine and poplar.
View Article and Find Full Text PDFAutoxidation Catalysis for Carbon-Carbon Bond Cleavage in Lignin.
ACS Cent Sci
December 2023
Renewable Resources and Enabling Sciences Center, National Renewable Energy Laboratory, Golden, Colorado 80401, United States.
Selective lignin depolymerization is a key step in lignin valorization to value-added products, and there are multiple catalytic methods to cleave labile aryl-ether bonds in lignin. However, the overall aromatic monomer yield is inherently limited by refractory carbon-carbon linkages, which are abundant in lignin and remain intact during most selective lignin deconstruction processes. In this work, we demonstrate that a Co/Mn/Br-based catalytic autoxidation method promotes carbon-carbon bond cleavage in acetylated lignin oligomers produced from reductive catalytic fractionation.
View Article and Find Full Text PDFCooperative Interplay of Brønsted Acid and Lewis Acid Sites in MIL-101(Cr) for Cross-Dehydrogenative Coupling of C-H Bonds.
ACS Appl Mater Interfaces
March 2021
Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, P. R. China.
Cross-dehydrogenative coupling (CDC) is an effective tool for carbon-carbon bond formation in chemical synthesis. Herein, we report a metal-organic framework (MOF) possessing dual Lewis acidic Cr sites and sulfonic acid sites (MIL-101(Cr)-SOH) as an efficient catalytic material for direct cross-coupling of xanthene and different nucleophiles using O as the oxidant. The highly porous structure of MIL-101(Cr)-SOH enables the free access of reactants to the catalytic active sites inside MOF pores.
View Article and Find Full Text PDFDouble Bonds Are Key to Fast Unimolecular Reactivity in First-Generation Monoterpene Hydroxy Peroxy Radicals.
J Phys Chem A
April 2020
Department of Chemistry, University of Copenhagen, Universitetsparken 5, Copenhagen Ø DK-2100, Denmark.
Monoterpenes are a group of volatile organic compounds (VOCs) emitted to the atmosphere in large amounts. Studies have linked the autoxidation of monoterpenes to the formation of secondary organic aerosols, which impact Earth's climate and human health. Here, we study the hydroxy peroxy radicals formed by OH- and O-addition to the six atmospherically relevant monoterpenes α-pinene, β-pinene, Δ-carene, camphene, limonene, and terpinolene.
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