Formation of Organic Chlorides by Reactions of Various Organic Compounds with Chlorine or Chlorine Dioxide

Abstract

  Various organic compounds, e. g., aldehydes, ketones, carboxylic acids, alcohols, esters, ethers, phenols, and amines were allowed to react with chlorine and chlorine dioxide in water, and the effects of pH, chlorine or chlorine dioxide dosage, and the reaction time were investigated.
   The amount of organic chlorides formed was determined by measuring total organic chloride (TOCl) and purgeable organic chloride (POCl) using a combustion-coulometric method, and chloroform using a gas chromatographic method.
   The following results were obtained: (1) the amounts of TOCl, POCl, and chloroform formed in the reaction with chlorine dioxide were generally much smaller than those in the reaction with chlorine (Table 1 and 2); (2) although pH influenced the formation of organic chlorides remarkablly, its effect depended upon the nature of each organic compound tested (Fig.1 and 2); and (3) in the case of the reaction with chlorine, the amount of chloroform formed increased with increasing initial chlorine concentration; however, in the case of the reactions with chlorine dioxide there existed the optimum concentration of chlorine dioxide which produced the maximum amount of chloroform (Fig.4 and 5).