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Title: Autoxidation of 1-decanethiol catalyzed by cobalt phthalocyaninetetrasulfonate on cationic latexes

Journal Article · · Journal of Organic Chemistry; (USA)
DOI:https://doi.org/10.1021/jo00274a029· OSTI ID:7196770
;  [1]
  1. Oklahoma State Univ., Stillwater (USA)

Cationic latexes 60 nm in diameter have been prepared by emulsion copolymerization of 2% of quaternary ammonium ion surfactant monomers and 1-5% of divinylbenzene with styrene. All of the surfactant monomers were bound to the product latexes, within experimental error. The cationic latexes bound cobalt phthalocyaninetetrasulfonate (CoPcTs) quantitatively from aqueous CoPcTsNa{sub 4}. The CoPcTs latexes catalyzed autoxidation of 1-decanethiol dispersed in water with zero-order consumption of dioxygen from a gas buret at 1 atm of pressure to at least 65% conversion of thiol. All reactions had an induction time before the start of oxygen consumption. Rates increased with pH in the range 7-9, and the following observations were made at pH 9. The zero-order rate constants with CoPcTs latexes were up to 14 times faster than with CoPcTsNa{sub 4} in aqueous solution. Hexadecyltrimethylammonium bromide and one of the surfactant monomers as micellar catalysts gave rate enhancements similar to those with latex catalysts. Rates of autoxidation in the three-phase mixtures of water, latex particles, and thiol droplets were not affected significantly by the method of mixing. The rate of latex-catalyzed oxidation increased with small amounts of added methanol and nonionic surfactant. Varied concentrations of dispersed 1-decanethiol in the range 1-4 {times} 10{sup {minus}2} M gave saturation kinetics. Increasing partial pressures of dioxygen in the range 0.25-1.0 atom gave small increases in rate.

OSTI ID:
7196770
Journal Information:
Journal of Organic Chemistry; (USA), Vol. 54:13; ISSN 0022-3263
Country of Publication:
United States
Language:
English