Formation of brominated disinfection byproducts from natural organic matter isolates and model compounds in a sulfate radical-based oxidation process.

A sulfate radical-based advanced oxidation process (SR-AOP) has received increasing application interest for the removal of water/wastewater contaminants. However, limited knowledge is available on its side effects. This study investigated the side effects in terms of the production of total organic bromine (TOBr) and brominated disinfection byproducts (Br-DBPs) in the presence of bromide ion and organic matter in water. Sulfate radical was generated by heterogeneous catalytic activation of peroxymonosulfate. Isolated natural organic matter (NOM) fractions as well as low molecular weight (LMW) compounds were used as model organic matter. Considerable amounts of TOBr were produced by SR-AOP, where bromoform (TBM) and dibromoacetic acid (DBAA) were identified as dominant Br-DBPs. In general, SR-AOP favored the formation of DBAA, which is quite distinct from bromination with HOBr/OBr(-) (more TBM production). SR-AOP experimental results indicate that bromine incorporation is distributed among both hydrophobic and hydrophilic NOM fractions. Studies on model precursors reveal that LMW acids are reactive TBM precursors (citric acid > succinic acid > pyruvic acid > maleic acid). High DBAA formation from citric acid, aspartic acid, and asparagine was observed; meanwhile aspartic acid and asparagine were the major precursors of dibromoacetonitrile and dibromoacetamide, respectively.

[1]  George P. Anipsitakis,et al.  Radical generation by the interaction of transition metals with common oxidants. , 2004, Environmental science & technology.

[2]  J. Rabani,et al.  Oxidation of aqueous bromide(1-) by hydroxyl radicals, studies by pulse radiolysis , 1977 .

[3]  B. Podkrajšek,et al.  Scavenging of SO4− radical anions by mono- and dicarboxylic acids in the Mn(II)-catalyzed S(IV) oxidation in aqueous solution , 2007 .

[4]  D. Reckhow,et al.  Effect of bromide and iodide ions on the formation and speciation of disinfection byproducts during chlorination. , 2006, Environmental science & technology.

[5]  P. Neta,et al.  Rate Constants for Reactions of Inorganic Radicals in Aqueous Solution , 1979 .

[6]  D. W. Margerum,et al.  Equilibrium and Kinetics of Bromine Hydrolysis. , 1996, Inorganic chemistry.

[7]  John J. Evans,et al.  Occurrence and mammalian cell toxicity of iodinated disinfection byproducts in drinking water. , 2008, Environmental science & technology.

[8]  P. Neta,et al.  Decarboxylation by S . O 4 - Radicals , 1978 .

[9]  U. Gunten,et al.  Advanced Oxidation of Bromide-Containing Waters: Bromate Formation Mechanisms , 1998 .

[10]  S. Richardson,et al.  Occurrence of a new generation of disinfection byproducts. , 2006, Environmental science & technology.

[11]  Jian-hui Sun,et al.  Oxone/Co(2+) oxidation as an advanced oxidation process: comparison with traditional Fenton oxidation for treatment of landfill leachate. , 2009, Water research.

[12]  U. von Gunten,et al.  Formation of iodinated organic compounds by oxidation of iodide-containing waters with manganese dioxide. , 2009, Environmental science & technology.

[13]  D. Dionysiou,et al.  Sulfate radical-based ferrous-peroxymonosulfate oxidative system for PCBs degradation in aqueous and sediment systems , 2009 .

[14]  R. Watts,et al.  Mechanism of base activation of persulfate. , 2010, Environmental science & technology.

[15]  D. Reckhow,et al.  DBP formation during chlorination and chloramination: Effect of reaction time, pH, dosage, and temperature , 2008 .

[16]  R. W. Fessenden,et al.  Rate constants and mechanism of reaction of sulfate radical anion with aromatic compounds , 2002 .

[17]  J. Croué,et al.  Production of sulfate radical from peroxymonosulfate induced by a magnetically separable CuFe2O4 spinel in water: efficiency, stability, and mechanism. , 2013, Environmental science & technology.

[18]  P. Westerhoff,et al.  Reactivity of natural organic matter with aqueous chlorine and bromine. , 2004, Water research.

[19]  P C Singer Mechanisms of organic halide formation during fulvic acid chlorination and implications with respect to preozonation , 1985 .

[20]  B. Legube,et al.  Chlorination studies of free and combined amino acids , 1994 .

[21]  D. Dionysiou,et al.  Intermediates and reaction pathways from the degradation of microcystin-LR with sulfate radicals. , 2010, Environmental science & technology.

[22]  Qian-Yuan Wu,et al.  Dichloroacetonitrile and dichloroacetamide can form independently during chlorination and chloramination of drinking waters, model organic matters, and wastewater effluents. , 2012, Environmental science & technology.

[23]  J. Croué,et al.  The formation of halogen-specific TOX from chlorination and chloramination of natural organic matter isolates. , 2009, Water research.

[24]  J. Barker,et al.  Free Radical Reactions Involving Cl•, Cl2-•, and SO4-• in the 248 nm Photolysis of Aqueous Solutions Containing S2O82- and Cl- , 2004 .

[25]  R. Larson,et al.  Citric acid: Potential precursor of chloroform in water chlorination , 1978, Naturwissenschaften.

[26]  B. Jefferson,et al.  Disinfection byproduct formation and fractionation behavior of natural organic matter surrogates. , 2009, Environmental science & technology.

[27]  N. Thomson,et al.  Persulfate injection into a gasoline source zone. , 2013, Journal of contaminant hydrology.

[28]  C. Shang,et al.  Bromate formation from bromide oxidation by the UV/persulfate process. , 2012, Environmental science & technology.

[29]  T. Schmidt,et al.  Formation of bromate in sulfate radical based oxidation: mechanistic aspects and suppression by dissolved organic matter. , 2014, Water research.

[30]  D. DeMarini,et al.  Occurrence, genotoxicity, and carcinogenicity of regulated and emerging disinfection by-products in drinking water: a review and roadmap for research. , 2007, Mutation research.

[31]  Paul G Tratnyek,et al.  Persulfate persistence under thermal activation conditions. , 2008, Environmental science & technology.

[32]  Alicia C. Diehl,et al.  DBP formation during chloramination , 2000 .

[33]  B. Nicholson,et al.  Bromide levels in natural waters: its relationship to levels of both chloride and total dissolved solids and the implications for water treatment. , 2004, Chemosphere.

[34]  George P. Anipsitakis,et al.  Chemical and microbial decontamination of pool water using activated potassium peroxymonosulfate. , 2008, Water research.

[35]  R. Summers,et al.  Haloacetic acid and trihalomethane formation from the chlorination and bromination of aliphatic beta-dicarbonyl acid model compounds. , 2008, Environmental science & technology.

[36]  J. Edwards,et al.  The Kinetics of the Oxidation of Halide Ions by Monosubstituted Peroxides , 1960 .

[37]  Jun Ma,et al.  Influence of pH on the formation of sulfate and hydroxyl radicals in the UV/peroxymonosulfate system. , 2011, Environmental science & technology.

[38]  J. Rabani,et al.  Oxidation of aqueous bromide ions by hydroxyl radicals. Pulse radiolytic investigation , 1972 .

[39]  W. Mitch,et al.  Halonitroalkanes, halonitriles, haloamides, and N-nitrosamines: a critical review of nitrogenous disinfection byproduct formation pathways. , 2012, Environmental Science and Technology.

[40]  Yang Deng,et al.  Sulfate radical-advanced oxidation process (SR-AOP) for simultaneous removal of refractory organic contaminants and ammonia in landfill leachate. , 2011, Water research.

[41]  Xiaoli Chai,et al.  Novel insights into enhanced dewaterability of waste activated sludge by Fe(II)-activated persulfate oxidation. , 2012, Bioresource technology.

[42]  H. Weiss The aqueous bromination of maleate and fumarate ions , 1977 .