Title page for ETD etd-05252004-122641


Type of Document Master's Thesis
Author Rule, Krista Lynn
Author's Email Address krule@vt.edu
URN etd-05252004-122641
Title The Mechanisms, Products, and Kinetics of Triclosan-Free Chlorine Reactions
Degree Master of Science
Department Environmental Engineering
Advisory Committee
Advisor Name Title
Vikesland, Peter J. Committee Chair
Edwards, Marc A. Committee Member
Little, John C. Committee Member
Keywords
  • Chlorophenoxyphenols
  • Pharmaceutical and Personal Care Products
  • Triclosan
  • Free Chlorine
  • Chlorophenols
Date of Defense 2004-05-24
Availability restricted
Abstract
The kinetics, products, and reaction pathways of triclosan/free chlorine reactions were investigated for the pH range 3.5-11. Although pH dependent speciation occurs in both triclosan and free chlorine, only the reaction between HOCl and the phenolate-triclosan was found to play a significant role in the kinetics. The second order rate constant for the reaction between phenolate-triclosan and HOCl was found to be 5.40 (±1.82) × 103 M-1s-1. Three chlorinated triclosan intermediates were tentatively identified based on mass spectral analysis. Additionally, 2,4-dichlorophenol, 2,4,6-trichlorophenol, and chloroform formed under excess free chlorine conditions. The majority of the chloroform formed during the reactions does not form via 2,4-dichlorophenol and 2,4,6-trichlorophenol oxidation. Therefore, the majority of chloroform is likely formed via the oxidation of triclosan’s phenolic ring. Based on the identified products, a reaction pathway was proposed for the oxidation of triclosan in the presence of free chlorine.

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