Cyclopentenones are common components of bio-oil produced from the pyrolysis of a variety of biomass feedstocks.  The goal of this project was to understand the thermal decomposition of both 2-cyclopentenone and 3-cyclopentenone.  Experimentally, this was done with a pulsed hyperthermal microtubular reactor and matrix-isolation FTIR.  Pyrolysis was performed on dilute, gas-phase mixtures of the individual cyclopentenones with argon at temperatures ranging from 700 to 1400 K.  Pyrolysis products were trapped in a low-temperature argon matrix and identified by FTIR spectroscopy.  Notable products include several unsaturated hydrocarbons, acrolein, carbon monoxide and propargyl radical.  Substituted ketenes were also observed and characterized for the first time in this work.  Gaussian 09 calculations were performed in order to understand the elementary steps leading to these pyrolysis products and intermediates, as well as to predict the reaction energetics involved.  As cyclopentenones are cyclic, oxygenated hydrocarbons that contain a ketone and a double bond, studying these molecules can begin to reveal how chemical structure affects the early steps in a pyrolysis mechanism.

Experimental and theoretical study of cyclopentenone pyrolysis

ACS Fall 2021

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