BOOK
Chemistry of Ozone in Water and Wastewater Treatment
Clemens von Sonntag | Urs von Gunten
(2012)
Additional Information
Book Details
Abstract
Even though ozone has been applied for a long time for disinfection and oxidation in water treatment, there is lack of critical information related to transformation of organic compounds. This has become more important in recent years, because there is considerable concern about the formation of potentially harmful degradation products as well as oxidation products from the reaction with the matrix components. In recent years, a wealth of information on the products that are formed has accumulated, and substantial progress in understanding mechanistic details of ozone reactions in aqueous solution has been made. Based on the latter, this may allow us to predict the products of as yet not studied systems and assist in evaluating toxic potentials in case certain classes are known to show such effects.
Keeping this in mind, Chemistry of Ozone in Water and Wastewater Treatment: From Basic Principles to Applications discusses mechanistic details of ozone reactions as much as they are known to date and applies them to the large body of studies on micropollutant degradation (such as pharmaceuticals and endocrine disruptors) that is already available. Extensively quoting the literature and updating the available compilation of ozone rate constants gives the reader a text at hand on which his research can be based. Moreover, those that are responsible for planning or operation of ozonation steps in drinking water and wastewater treatment plants will find salient information in a compact form that otherwise is quite disperse. A critical compilation of rate constants for the various classes of compounds is given in each chapter, including all the recent publications.
This is a very useful source of information for researchers and practitioners who need kinetic information on emerging contaminants. Furthermore, each chapter contains a large selection of examples of reaction mechanisms for the transformation of micropollutants such as pharmaceuticals, pesticides, fuel additives, solvents, taste and odor compounds, cyanotoxins.
Authors: Prof. Dr. Clemens von Sonntag, Max-Planck-Institut für Bioanorganische Chemie, Mülheim an der Ruhr, and Instrumentelle Analytische Chemie, Universität Duisburg-Essen, Essen, Germany and Prof. Dr. Urs von Gunten, Eawag, Swiss Federal Institute of Aquatic Science and Technology, Dübendorf, and Ecole Polytechnique Federal de Lausanne, Lausanne, Switzerland.
Table of Contents
Section Title | Page | Action | Price |
---|---|---|---|
Cover page | 1 | ||
Half-title page | 2 | ||
Title page | 3 | ||
Copyright page | 4 | ||
Contents | 5 | ||
About the Authors | 10 | ||
Chapter 1 | 11 | ||
Historical background and scope of the book | 11 | ||
Chapter 2 | 16 | ||
Physical and chemical properties of ozone | 16 | ||
2.1 INTRODUCTORY REMARKS | 16 | ||
2.2 GENERATION OF OZONE | 17 | ||
2.3 OZONE SOLUBILITY IN WATER | 18 | ||
2.4 UV–VIS SPECTRUM OF OZONE | 19 | ||
2.5 DETERMINATION OF THE OZONE CONCENTRATION | 21 | ||
2.5.1 The N,N-diethyl-p-phenylenediamine (DPD) method | 21 | ||
2.5.2 The indigo method | 22 | ||
2.6 METHODS FOR MEASURING OZONE KINETICS | 23 | ||
2.6.1 Ozone decay measurements | 24 | ||
2.6.2 Quenching of ozone with buten-3-ol | 25 | ||
2.6.3 Reactive absorption | 25 | ||
2.6.4 Competition kinetics | 26 | ||
2.7 REDUCTION POTENTIALS OF OZONE AND OTHER OXYGEN SPECIES | 27 | ||
2.8 STABILITY OF OZONE SOLUTIONS | 28 | ||
2.9 REACTIVITY OF OZONE | 28 | ||
2.9.1 pH dependence of ozone reactions and the \"reactivity pK” | 29 | ||
2.9.2 Multiple reaction sites within one molecule | 30 | ||
Chapter 3 | 32 | ||
Ozone kinetics in drinking water and wastewater | 32 | ||
3.1 STABILITY OF OZONE IN VARIOUS WATER SOURCES | 32 | ||
3.2 MOLECULAR WEIGHT DISTRIBUTION OF DISSOLVED ORGANIC MATTER | 40 | ||
3.3 MINERALISATION AND CHEMICAL OXYGEN DEMAND | 42 | ||
3.4 FORMATION OF ASSIMILABLE ORGANIC CARBON | 42 | ||
3.5 FORMATION AND MITIGATION OF DISINFECTION BY-PRODUCTS | 44 | ||
3.6 UV ABSORBANCE OF DISSOLVED ORGANIC MATTER | 45 | ||
3.7 RELEVANCE OF OZONE KINETICS FOR THE ELIMINATION OF MICROPOLLUTANTS | 46 | ||
3.8 HYDROXYL RADICAL YIELD AND •OH-SCAVENGING RATE OF DISSOLVED ORGANIC MATTER | 48 | ||
3.9 ELIMINATION OF OZONE-REFRACTORY MICROPOLLUTANTS BY THE •OH ROUTE | 49 | ||
3.10 OZONE-BASED ADVANCED OXIDATION PROCESSES | 51 | ||
3.10.1 Peroxone process | 51 | ||
3.10.2 UV photolysis of ozone | 54 | ||
3.10.3 Reaction of ozone with activated carbon | 55 | ||
Chapter 4 | 57 | ||
Inactivation of micro-organisms and toxicological assessment of ozone-induced products of micropollutants | 57 | ||
4.1 DISINFECTION KINETICS | 57 | ||
4.2 INACTIVATION MECHANISMS: ROLE OF MEMBRANES AND DNA | 60 | ||
4.3 REACTIONS WITH NUCLEIC ACID COMPONENTS | 61 | ||
4.4 REACTION WITH DNA | 62 | ||
4.5 APPLICATION OF OZONE FOR DISINFECTION IN DRINKING WATER AND WASTEWATER | 63 | ||
4.6 TOXICOLOGICAL ASSESSMENT OF OZONE INDUCED TRANSFORMATION PRODUCTS | 63 | ||
4.7 ENDOCRINE DISRUPTING COMPOUNDS | 64 | ||
4.7.1 Laboratory studies | 66 | ||
4.7.2 Full-scale studies | 67 | ||
4.8 ANTIMICROBIAL COMPOUNDS | 68 | ||
4.9 TOXICITY | 70 | ||
Chapter 5 | 73 | ||
Integration of ozonation in drinking water and wastewater process trains | 73 | ||
5.1 HISTORICAL ASPECTS | 73 | ||
5.1.1 Drinking water | 73 | ||
5.1.2 Municipal wastewater | 73 | ||
5.2 DRINKING WATER TREATMENT SCHEMES INCLUDING OZONATION | 74 | ||
5.3 MICROPOLLUTANTS IN WATER RESOURCES, DRINKING WATER AND WASTEWATER | 78 | ||
5.4 ENHANCED WASTEWATER TREATMENT WITH OZONE | 80 | ||
5.5 ENERGY REQUIREMENTS FOR MICROPOLLUTANT TRANSFORMATION IN DRINKING WATER AND WASTEWATER | 81 | ||
5.6 SOURCE CONTROL | 82 | ||
5.7 RECLAMATION OF WASTEWATER | 83 | ||
5.8 COMPARISON OF THE APPLICATION OF OZONE IN THE URBAN WATER CYCLE | 85 | ||
Chapter 6 | 88 | ||
Olefins | 88 | ||
6.1 REACTIVITY OF OLEFINS | 88 | ||
6.2 THE CRIEGEE MECHANISM | 91 | ||
6.3 PARTIAL OXIDATION | 94 | ||
6.4 DECAY OF THE OZONIDE VIA FREE RADICALS | 95 | ||
6.5 DETECTION OF α-HYDROXYALKYLHYDROPEROXIDES | 95 | ||
6.6 OZONE REACTIONS OF OLEFINS - PRODUCTS AND REACTIONS OF REACTIVE INTERMEDIATES | 96 | ||
6.6.1 Methyland halogen-substituted olefins | 96 | ||
6.6.2 Acrylonitrile, vinyl acetate, diethyl vinylphosphonate, vinyl phenyl sulfonate, vinylsulfonic acid and vinylene carbonate | 98 | ||
6.6.3 Acrylic, methacrylic, fumaric, maleic and muconic acids | 99 | ||
6.6.4 Muconic acids | 103 | ||
6.6.5 Cinnamic acids | 105 | ||
6.6.6 Dichloromaleic acid | 106 | ||
6.6.7 Pyrimidine nucleobases | 106 | ||
6.7 MICROPOLLUTANTS WITH OLEFINIC FUNCTIONS | 109 | ||
Chapter 7 | 115 | ||
Aromatic compounds | 115 | ||
7.1 REACTIVITY OF AROMATIC COMPOUNDS | 115 | ||
7.2 DECAY OF OZONE ADDUCTS | 122 | ||
7.3 OZONE REACTIONS OF AROMATIC COMPOUNDS - PRODUCTS AND REACTIONS OF REACTIVE INTERMEDIATES | 124 | ||
7.3.1 Methoxylated benzenes | 124 | ||
7.3.2 Phenols | 127 | ||
7.4 MICROPOLLUTANTS WITH AROMATIC FUNCTIONS | 130 | ||
Chapter 8 | 137 | ||
Nitrogen-containing compounds | 137 | ||
8.1 REACTIVITY OF NITROGEN-CONTAINING COMPOUNDS | 137 | ||
8.2 GENERAL MECHANISTIC CONSIDERATIONS | 144 | ||
8.2.1 Aliphatic amines | 144 | ||
8.2.2 Aromatic amines (anilines) | 149 | ||
8.2.3 Nitrogen-containing heterocyclic compounds | 151 | ||
8.3 MICROPOLLUTANTS WITH NITROGEN-CONTAINING FUNCTIONS | 152 | ||
8.3.1 The N-Nitrosodimethylamine (NDMA) puzzle | 162 | ||
Chapter 9 | 166 | ||
Reactions of sulfur-containing compounds | 166 | ||
9.1 REACTIVITY OF SULFUR-CONTAINING COMPOUNDS | 166 | ||
9.2 THIOLS | 167 | ||
9.3 SULFIDES, DISULFIDES AND SULFINIC ACIDS | 168 | ||
9.4 SULFOXIDES | 170 | ||
9.5 MICROPOLLUTANTS CONTAINING AN OZONE-REACTIVE SULFUR | 171 | ||
Chapter 10 | 173 | ||
Compounds with C–H functions as ozone-reactive sites | 173 | ||
10.1 REACTIVITY OF COMPOUNDS WITH C–H FUNCTIONS AS OZONE-REACTIVE SITES | 173 | ||
10.2 GENERAL MECHANISTIC CONSIDERATIONS | 175 | ||
10.3 FORMATE ION | 177 | ||
10.4 2-METHYL-2-PROPANOL (TERTIARY BUTANOL) | 179 | ||
10.5 2-PROPANOL | 180 | ||
10.6 CARBOHYDRATES | 184 | ||
10.7 DIHYDROGEN TRIOXIDE - PROPERTIES OF A SHORT-LIVED INTERMEDIATE | 186 | ||
10.8 SATURATED MICROPOLLUTANTS LACKING OZONE-REACTIVE HETEROATOMS | 188 | ||
Chapter 11 | 189 | ||
Inorganic anions and the peroxone process | 189 | ||
11.1 INTRODUCTORY REMARKS | 189 | ||
11.2 HYDROXIDE ION | 191 | ||
11.3 HYDROPEROXIDE ION - PEROXONE PROCESS | 192 | ||
11.4 FLUORIDE | 193 | ||
11.5 CHLORIDE | 194 | ||
11.6 HYPOCHLORITE | 195 | ||
11.7 CHLORITE | 196 | ||
11.8 BROMIDE | 196 | ||
11.9 HYPOBROMITE | 197 | ||
11.10 BROMITE | 198 | ||
11.11 IODIDE | 198 | ||
11.12 NITRITE | 199 | ||
11.13 AZIDE | 200 | ||
11.14 HYDROGEN SULFIDE | 201 | ||
11.15 HYDROGEN SULFITE | 202 | ||
11.16 BROMATE FORMATION AND MITIGATION IN WATER TREATMENT | 202 | ||
11.17 BROMIDE-CATALYSED REACTIONS | 205 | ||
11.18 MITIGATION OF IODIDE-RELATED PROBLEMS | 206 | ||
Chapter 12 | 208 | ||
Reactions with metal ions | 208 | ||
12.1 REACTIVITY OF METAL IONS | 208 | ||
12.2 ARSENIC | 209 | ||
12.3 COBALT | 210 | ||
12.4 COPPER | 210 | ||
12.5 IRON | 210 | ||
12.6 LEAD | 211 | ||
12.7 MANGANESE | 211 | ||
12.8 SELENIUM | 212 | ||
12.9 SILVER | 212 | ||
12.10 TIN | 214 | ||
12.11 METAL IONS AS MICROPOLLUTANTS | 214 | ||
Chapter 13 | 216 | ||
Reactions with free radicals | 216 | ||
13.1 REACTIVITY OF RADICALS | 216 | ||
13.2 OZONE REACTIONS WITH REDUCING RADICALS | 217 | ||
13.3 OZONE REACTIONS WITH CARBON-CENTERED RADICALS | 218 | ||
13.4 OZONE REACTIONS WITH OXYGEN-CENTERED RADICALS | 220 | ||
13.5 OZONE REACTIONS WITH NITROGENAND SULFUR-CENTRED RADICALS | 222 | ||
13.6 OZONE REACTIONS WITH HALOGEN-CENTRED RADICALS | 223 | ||
Chapter 14 | 228 | ||
Reactions of hydroxyl and peroxyl radicals | 228 | ||
14.1 INTRODUCTORY REMARKS | 228 | ||
14.2 HYDROXYL RADICAL REACTIONS | 228 | ||
14.2.1 Addition reactions | 228 | ||
14.2.2 H-abstraction reactions | 230 | ||
14.2.3 Electron transfer reactions | 231 | ||
14.3 DETERMINATION OF •OH RATE CONSTANTS | 232 | ||
14.4 DETECTION OF •OH IN OZONE REACTIONS | 233 | ||
14.5 DETERMINATION OF •OH YIELDS IN OZONE REACTIONS | 235 | ||
14.6 FORMATION OF PEROXYL RADICALS | 236 | ||
14.7 REDOX PROPERTIES OF PEROXYL RADICALS AND REACTION WITH OZONE | 236 | ||
14.8 UNIMOLECULAR DECAY OF PEROXYL RADICALS | 237 | ||
14.9 BIMOLECULAR DECAY OF PEROXYL RADICALS | 238 | ||
14.10 REACTIONS OF OXYL RADICALS | 239 | ||
14.11 INVOLVEMENT OF •OH RADICALS IN CHLORATE AND BROMATE FORMATION | 240 | ||
14.11.1 Chlorate formation | 240 | ||
14.11.2 Bromate formation | 241 | ||
14.12 DEGRADATION OF OZONE-REFRACTORY MICROPOLLUTANTS BY •OH/PEROXYL RADICALS | 244 | ||
14.12.1 Saturated aliphatic compounds | 244 | ||
14.12.2 Aromatic compounds | 246 | ||
14.12.3 Chlorinated olefins | 248 | ||
14.12.4 Perfluorinated compounds | 251 | ||
References | 252 | ||
Index | 289 |