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Oxidation of n-alkanes using TS-1 and H2O2: Effects of chain length and solvents

Journal Article · · Applied Catalysis A: General

The selective oxidation of n-C8H18, n-C12H26, n-C16H34, n-C20H42, and n-C36H74 was studied with a goal of using these as models to provide insight into how to functionalize polyolefins. Reactions were carried out using a TS-1 catalyst and H2O2 in a batch reactor with different cosolvents, including methanol, acetone, acetonitrile, methyl ethyl ketone, and methyl butyl ketone. Rates decreased with increasing alkane size, possibly due to the reduced solubility of larger alkanes into the water-rich phases. Cosolvents that promote the partitioning of alkanes in the aqueous phase increased the rates. 1H NMR spectroscopy demonstrated that ketones were the primary products, although some alcohols also formed. There was preferential reaction at the 2 position in the alkanes, but reaction at central carbons was also observed. The results of this study suggest strategies for using this catalytic chemistry to functionalize polyolefins.

Research Organization:
University of Pennsylvania, Philadelphia, PA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0022238
OSTI ID:
2583362
Journal Information:
Applied Catalysis A: General, Journal Name: Applied Catalysis A: General Vol. 704; ISSN 0926-860X
Publisher:
Elsevier BVCopyright Statement
Country of Publication:
United States
Language:
English

References (37)

Continuous Synthesis of Epoxides from Alkenes by Hydrogen Peroxide with Titanium Silicalite‐1 Catalyst Using Flow Reactors journal July 2023
Ultra‐Narrow Alkane Product Distribution in Polyethylene Waste Hydrocracking by Zeolite Micro‐Mesopore Diffusion Optimization journal October 2024
Investigation of Small‐Pore Zeolites via Vapor‐Phase Adsorption of n ‐Hexane  journal March 2021
The influence of physicochemical properties of ZSM‐5 on catalytic dewaxing journal January 1990
Reusing a residue from the juice industry: extraction of oil from passion fruit seeds and its incorporation into liposomes
  • Suzuki, Rúbia Michele; Sérgi Gomes, Maria Carolina; Sgorlon, Juliana Guerra
  • Journal of Chemical Technology & Biotechnology, Vol. 99, Issue 3 https://doi.org/10.1002/jctb.7573
journal December 2023
Intrinsic Molecular Volume as a Measure of the Cavity Term in Linear Solvation Energy Relationships: Octanol-Water Partition Coefficients and Aqueous Solubilities journal July 1986
A Kinetic Investigation of Co-Solvent Effects in Oxyfunctionalization of n-Hexane by Hydrogen Peroxide on TS-2 journal August 1994
Studies on the Catalytic-Oxidation of Alkanes and Alkenes by Titanium Silicates journal September 1994
Kinetic Modeling ofn-Hexane Oxyfunctionalization by Hydrogen Peroxide on Titanium Silicalites of MEL Structure (TS-2) journal July 1996
Oxidation of octane and cyclohexane using a new porous substrate, Ti-MMM-1 journal March 2002
Conversion of polyethylene waste to short chain hydrocarbons under mild temperature and hydrogen pressure with metal-free and metal-loaded MFI zeolites journal December 2023
Intensified reactive extraction for the acid-catalyzed conversion of fructose to 5-hydroxymethyl furfural journal January 2022
Hydrogenolysis of n-eicosane over Ru-based catalysts in a continuous flow reactor journal January 2023
Gradient-temperature control enhances oxi-upcycling of polyethylene plastics to dicarboxylic acids over TS-1 zeolite journal January 2025
Selective, Catalytic Oxidations of C–H Bonds in Polyethylenes Produce Functional Materials with Enhanced Adhesion journal January 2021
Unique solvent effect of microporous crystalline titanosilicates in the oxidation of 1-hexene and cyclohexene journal May 2008
PFG NMR and QENS diffusion study of n-alkane homologues in MFI-type zeolites journal March 2006
Effective hierarchization of TS-1 and its catalytic performance in propene epoxidation journal April 2019
Regioselective alkane oxygenation with H2O2 catalyzed by titanosilicalite TS-1 journal May 2006
Catalytic Upcycling of Polyolefins journal August 2024
Adsorption of Small Alkanes on ZSM-5 Zeolites: Influence of Brønsted Sites journal June 2016
Catalytic Consequences of Hierarchical Pore Architectures within MFI and FAU Zeolites for Polyethylene Conversion journal April 2024
Demonstrating the Critical Role of Solvation in Supported Ti and Nb Epoxidation Catalysts via Vapor-Phase Kinetics journal January 2020
Catalytic Hydroxylation of Polyethylenes journal August 2017
Kinetics of dewaxing neutral oils over ZSM-5 journal June 1991
Universal Liquid Mixture Models for Vapor−Liquid and Liquid−Liquid Equilibria in the Hexane−Butanol−Water System journal January 2011
Cooperative Effects between Hydrophilic Pores and Solvents: Catalytic Consequences of Hydrogen Bonding on Alkene Epoxidation in Zeolites journal January 2019
Conversion of Polyolefin Waste to Liquid Alkanes with Ru-Based Catalysts under Mild Conditions journal December 2020
Ti-Peroxo Species in the TS-1/H 2 O 2 /H 2 O System journal March 2004
Oxyfunctionalization of alkanes with hydrogen peroxide on titanium silicalite journal May 1990
Electronic modulation of metal-support interactions improves polypropylene hydrogenolysis over ruthenium catalysts journal September 2022
Ultrafast flow chemistry for the acid-catalyzed conversion of fructose journal January 2019
Homogeneous and heterogeneous catalysts for hydrogenation of CO 2 to methanol under mild conditions journal January 2021
Switching between classical/nonclassical crystallization pathways of TS-1 zeolite: implication on titanium distribution and catalysis journal January 2022
Polyethylene upcycling to long-chain alkylaromatics by tandem hydrogenolysis/aromatization journal October 2020
Liquid-phase oxidation of normal C10–C13 hydrocarbons with hydrogen peroxide on the titanium-containing catalyst ts-1: The effect of process conditions on product composition journal September 2010
Recovery/Reuse of Heterogeneous Supported Spent Catalysts journal May 2021

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