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Kinetics and mechanism for thermal and photochemical decomposition of 4,4′-azobis(4-cyanopentanoic acid) in aqueous media

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Abstract

4,4′-Azobis(4-cyanopentanoic acid) comprises two diastereoisomers that decompose at different rates in aqueous media [racemic-ACPA: Ea = 132.2 kJ mol−1, A = 4.76 × 1015 s−1, 10 h t1/2 = 65 °C; meso-ACPA: Ea = 131.7 kJ mol−1, A = 2.98 × 1015 s−1,10 h t1/2 = 67 °C], but both decompose at a similar though faster rate in N,N-dimethylformamide [Ea = 134.0 kJ mol−1, A = 1.26 × 1016 s−1,10 h t1/2 = 63 °C]. The major product of decomposition in both aqueous and organic media is the ketenimine formed by C–N coupling of the radicals formed, which is irreversibly trapped as an amide in aqueous media.

Graphical abstract: Kinetics and mechanism for thermal and photochemical decomposition of 4,4′-azobis(4-cyanopentanoic acid) in aqueous media

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Publication details

The article was received on 05 Apr 2019, accepted on 07 May 2019 and first published on 08 May 2019


Article type: Communication
DOI: 10.1039/C9PY00507B
Polym. Chem., 2019, Advance Article

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    Kinetics and mechanism for thermal and photochemical decomposition of 4,4′-azobis(4-cyanopentanoic acid) in aqueous media

    Y. Zhou, Z. Zhang, A. Postma and G. Moad, Polym. Chem., 2019, Advance Article , DOI: 10.1039/C9PY00507B

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