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Kinetics of radical telomerization of acrylic acid in the presence of 1-octadecanethiol

Authors
  • Mezhuev, Yaroslav O.1
  • Sizova, Oksana Y.1
  • Korshak, Yuri V.1
  • Luss, Anna L.1
  • Plyushchii, Ivan V.1
  • Svistunova, Alina Y.1
  • Stratidakis, Antonis K.2
  • Panov, Alexey V.3
  • Shtilman, Mikhail I.1
  • Tsatsakis, Aristidis M.2
  • 1 D. Mendeleev University of Chemical Technology of Russia, Russia , (Russia)
  • 2 Medical School, University of Crete, Voutes Campus, Heraklion , (Greece)
  • 3 Moscow Technological University, Russia , (Russia)
Type
Published Article
Journal
Pure and Applied Chemistry
Publisher
Walter de Gruyter GmbH
Publication Date
Oct 23, 2018
Volume
90
Issue
11
Pages
1743–1754
Identifiers
DOI: 10.1515/pac-2018-0601
Source
De Gruyter
Keywords
License
Yellow

Abstract

The oligomer of acrylic acid with a thiooctadecyl end-group was obtained by using octadecyl mercaptan as the chain-transfer agent. The resulting oligomer was characterized by 1H NMR and 13C NMR spectroscopy and critical micelle concentration was determined in aqueous solution. The order with respect to the initiator concentration was 0.5 and 1.6 with respect to the monomer concentration. The abnormal reaction order with respect to the monomer concentration was explained by participation in the chain propagation of unassociated and associated forms of acrylic acid, which were stabilized by formation of hydrogen bonds. The kinetic parameters of telomerization were determined. Telomerization with acrylic acid in the non-associated form had lower activation energy and lower pre-exponential factor than in the case of associated forms. The synthesis of the acrylic acid oligomer with a thiooctadecyl end-group having a low critical micelle concentration in water was carried out in one stage and corresponds to the concept of atom economy.

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