Solvophobic acceleration of Diels-Alder reactions in supercritical carbon dioxide

Jin Qian, Michael Timko, Jefferson Tester, Jeffrey Steinfeld, Brian Buckley, Bozena Winni

    Research output: Contribution to journalConference articlepeer-review

    Abstract

    The kinetics of the Diels-Alder reaction of dienophile N-ethylmaleimide and 9-ydroxymethylanthracene was studied. The Diels-Alder reaction of dienophile N-ethylmaleimide with 9-hydroxymethylanthracene proceeded at rates in scCO 2 that are much faster than in traditional organic solvents, e.g., acetonitrile, methanol, etc. The transformation of reactants to transition state was concurrent with a decrease in the exposed surface area of the solutes, which decreased the molecular interaction between the solute (reactants or transition state) and the solvent. This decrease in solute-solvent interaction accelerated the reaction. The results indicated negative pressure and density dependencies of the rate constant, which was consistent with the solvophobic mechanism due to the direct positive relationship between fluid density and solute solubility. This is an abstract of a paper presented at the 6th Annual Green Chemistry and Engineering Conference (Washington, D.C. 6/24-27/2003).

    Original languageEnglish (US)
    JournalACS Division of Environmental Chemistry, Preprints
    Volume43
    Issue number1
    StatePublished - 2003
    EventAmerican Chemical Society 6th Annual Green Chemistry and Engineering Conference Proceedings: Meeting Global Challenges Through Economic and Environmental Innovations - Wahisngton, DC, United States
    Duration: Jun 24 2002Jun 27 2002

    All Science Journal Classification (ASJC) codes

    • Chemical Engineering(all)

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