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

Callison, J. et al. (2012) Origin of impurities formed in the polyurethane production chain. 1: conditions for chlorine transfer from an aryl isocyanide dichloride byproduct. Industrial and Engineering Chemistry Research, 51(6), pp. 2515-2523. (doi: 10.1021/ie2013136)

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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═CCl2 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 C6H5N═CCl2, either alone or mixed with methylene diaryl isocyanate species, in o-C6H4Cl2, a polyurethane process solvent, led to the formation of mixtures containing dichloro- and trichlorobiphenyl isomers.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Winfield, Professor John and Lennon, Professor David
Authors: Callison, J., Edge, R., Cuba de, K.R., Carr, R.H., McDouall, J.J.W., Collison, D., McInnes, E.J.L., Bordon van der, W., Velde van der, K., Winfield, J.M., and Lennon, D.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Industrial and Engineering Chemistry Research
ISSN:0888-5885
Published Online:23 December 2011

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