Origin of impurities formed in the polyurethane production chain. 1. Conditions for chlorine transfer from an aryl isocyanide dichloride byproduct

June Callison, Ruth Edge, Kimberly R. De Cuba, Robert H. Carr, Joseph J W McDouall, David Collison, Eric J L McInnes, Willem Van Der Borden, Klaas Van Der Velde, John M. Winfield, David Lennon

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Phenyl and 4-methylphenyl isocyanide dichlorides are models for byproduct that may be formed in the later stages of certain polyurethane production chains. Photochemical electron paramagnetic resonance (EPR) studies (λ > 310 nm), using the spin trap, N-tert-butyl-α-phenylnitrone, confirm a previously made suggestion that ArN=CCl 2 can behave as a chlorine radical source. EPR spectra recorded during and after irradiation and supported by simulations evolve over time and indicate formation of the short-lived spin trap-Cl • adduct and a longer lived benzoyl-N-tert-butylnitroxide radical. Photolysis of C 6H 5N=CCl 2, either alone or mixed with methylene diaryl isocyanate species, in o-C 6H 4Cl 2, a polyurethane process solvent, led to the formation of mixtures containing dichloro- and trichlorobiphenyl isomers. © 2011 American Chemical Society.
    Original languageEnglish
    Pages (from-to)2515-2523
    Number of pages8
    JournalIndustrial and Engineering Chemistry Research
    Volume51
    Issue number6
    DOIs
    Publication statusPublished - 15 Feb 2012

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