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  • Reaction behaviour of sterically hindered alpha-(substituted methyl)acrylic esters with tert-butoxy radicals studied by a nitroxide trapping technique

    Author(s)
    Sato, E
    Zetterlund, PB
    Yamada, B
    Busfield, WK
    Jenkins, ID
    Griffith University Author(s)
    Jenkins, Ian D.
    Year published
    2003
    Metadata
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    Abstract
    The nitroxide free radical trapping technique in connection with HPLC and electrospray ionization mass spectrometry has been employed to study reactions of tert-butoxy radicals with methyl -(2-methyl-2-carbomethoxypropyl)acrylate (methyl methacrylate dimer (MMAD)) and methyl -(2,2,2-tris(carbomethoxy)ethyl)acrylate (M(TM)EA). It has been shown that the adduct radical derived from MMAD undergoes -fragmentation and expels the 2-carbomethoxy-2-propyl radical. No fragmentation was detected in the case of M(TM)EA. Rate coefficients of trapping and -fragmentation of the tert-butoxy radical in the literature have enabled estimations ...
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    The nitroxide free radical trapping technique in connection with HPLC and electrospray ionization mass spectrometry has been employed to study reactions of tert-butoxy radicals with methyl -(2-methyl-2-carbomethoxypropyl)acrylate (methyl methacrylate dimer (MMAD)) and methyl -(2,2,2-tris(carbomethoxy)ethyl)acrylate (M(TM)EA). It has been shown that the adduct radical derived from MMAD undergoes -fragmentation and expels the 2-carbomethoxy-2-propyl radical. No fragmentation was detected in the case of M(TM)EA. Rate coefficients of trapping and -fragmentation of the tert-butoxy radical in the literature have enabled estimations of absolute rate coefficients for additions of the tert-butoxy radical and the methyl radical to monomer, hydrogen abstraction from monomer by the tert-butoxy radical, and -fragmentation of the adduct radical (MMAD only). The reactions of tert-butoxy radicals with M(TM)EA are slower than with MMAD due to the steric hindrance of the -substituent.
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    Journal Title
    Polymer International
    Volume
    52
    Publisher URI
    https://onlinelibrary.wiley.com/doi/10.1002/pi.1293
    DOI
    https://doi.org/10.1002/pi.1293
    Subject
    Analytical chemistry
    Chemical engineering
    Materials engineering
    Publication URI
    http://hdl.handle.net/10072/6346
    Collection
    • Journal articles

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