Click for next page ( 140


The National Academies | 500 Fifth St. N.W. | Washington, D.C. 20001
Copyright © National Academy of Sciences. All rights reserved.
Terms of Use and Privacy Statement



Below are the first 10 and last 10 pages of uncorrected machine-read text (when available) of this chapter, followed by the top 30 algorithmically extracted key phrases from the chapter as a whole.
Intended to provide our own search engines and external engines with highly rich, chapter-representative searchable text on the opening pages of each chapter. Because it is UNCORRECTED material, please consider the following text as a useful but insufficient proxy for the authoritative book pages.

Do not use for reproduction, copying, pasting, or reading; exclusively for search engines.

OCR for page 139
I The Chemistry of Disinfectants in Water: Reactions and Products A major objective of this review of disinfectant chemistry is the identification of likely by-products that might be formed through the use of specific disinfectants. The review is part of a comprehensive study of the possible health elects of contaminants in drinking water. The prediction of possible products, which is attempted herein, is intended to be a guide to those contaminants that might require removal or toxicological evaluation; however, neither of these two aspects of the overall study is discussed in this chapter. While there is some current research on using combinations of disinfectants sequentially, the chemical consequences and benefits of this strategy are not yet clear. This subject has been omitted from the report. Similarly the subcommittee did not review the chemical side benefits of disinfection, such as removal of cyanides, phenols, and, possibly, many other compounds, although these side benefits may be of considerable Importance. Although there is now a rapidly growing body of scientific literature on chlorine by-products in drinking waters, comparable information for other disinfectants is very scarce. The subcommittee believed that reviewing chlorine by-products in detail, while saying little about other disinfectants, could suggest (probably erroneously) that these alternate disinfectants are free of the difficulties that are encountered with chlorine. In an attempt to circumvent this problem, the subcommittee found it necessary to broaden its information base by reviewing not only data on potable water, but also studies on nonpotable water, such as 139

OCR for page 139
140 DRINKING WATER AND HEALTH treated sewage effluents, and on synthetic model solutions, the data from which might be applicable to potable waters. These studies on nonpota- ble water shed light on the chemistry of disinfectants in drinking waters, although it is obvious that many compounds produced in treated sewage or in artificial laboratory experiments may never be found in drinking waters. To avoid confusion, a clear distinction has been drawn throughout this chapter between information acquired from actual drinking waters and information derived from other sources. A great deal of research on the chemistry of disinfectants is now in progress. An attempt was made to ensure that this chapter was current by contacting many scientists who are working in this field in the United States and abroad. However, in an active field such as this, any review can become rapidly outdated. The chapter begins with a preliminary discussion of the character of the natural organic substances from which by-products of organic disinfectants are thought to originate. Subsequent sections describe the chemistry of chlorine, chloramines, halogens (Br2 and I2), chlorine dioxide, and, finally, ozone. PRECURSOR COMPOUNDS AND THE HALOFORM REACTION Since 1975, many investigators have assumed that the ubiquitous appearance of chlorofo~ (CHCl3) and other THM's (trihalomethanes, or haloforms) in chlorinated water can be explained by the mechanisms involved in the "haloform reaction" and that the principal precursors of THM's that are found in natural waters are humic substances. As discussed subsequently in the section pertaining to chlorine chemistry, the haloform reaction will proceed only if specific functional groups are present in the available pool of organic compounds. It is likely that the haloform reaction does occur when natural waters are chlorinated and that humic substances provide the necessary functional groups, but it is not certain that either of these postulates is true. For that reason, both topics the haloform reaction and humic substancesmerit further . . . alscusslon. The Haloform Reaction The terms "trihalomethanes" and "haloforms" are synonymous, but the term "haloform reaction" is often misused in discussions of THM formation in natural waters. In recent literature, it has been used to mean any reaction between aqueous solutions of organic compounds

OCR for page 139
The Chemistry of Disinfectants in Water 141 and hypohalous acids that results in THM formation, but it actually has a classic chemical definition that is more restrictive. In the future, the expanded meaning may be preferred, but at present the term "haloform reaction" is inappropriate from a strict chemical interpretation, unless one is sure that the THM's are formed by reactions between hypohalous acids and compounds containing acetyl groups or substituents that can be converted to acetyl groups. The classic haloform reaction, which is actually a series of well-defined reactions, has been known since the 1800's (Fuson and Bull, 1934~. The earliest studies were conducted with nonaqueous solvents, high concen- trations of organic compounds, and chlorine gas, but research since 1974 has focused more on defining the reactions that yield THM's under conditions that are closer to those more commonly encountered during the treatment of drinking water supplies. Compounds, or classes of compounds, with the general formula CH3CHOHR or CH3COR, which includes ethanol, acetaldehyde, methyl ketones, and secondary alcohols, can participate in the haloform reaction. So may olefinic substances with the general structure CH3CH=CR,R2, which will be oxidized by hypochlorous acid (HOC1) first to secondary alcohols and then to methyl ketones. The site of attack by chlorine is the carbon adjacent to the one bearing oxygen, and this attack, wherein the hydrogen atoms are successively replaced by chlorine, is preceded by a dissociation of one hydrogen (as H+) to produce a carbanion ('H2-) that can react with C1(I), from hypochlo- rous acid. Chlorine substitution continues until all hydrogen atoms on the same carbon have been replaced. The final step involves a hydrolytic cleavage of the trihalogenated carbon (the trichlorinated carbon, in this example) to form the THM, which in this example would be chloroform (Morris, 1975). While it is well known that compounds containing acetyl groups are reactants in the haloform reaction, methyl ketone (acetone, CH3COCH3) itself is not a likely precursor during water treatment. According to Morris and Baum (1978), who cited a study by Bell and Lidwell (1940), the half-life for chloroform formation from acetone at pH 7 and room temperature is nearly a year. Stevens et al. (1978) also discounted acetone as a precursor of THM because of the slow reaction rate. The rate-limiting step in the haloform reaction is the ionization that produces carbanions, and, apparently, simple ketones are not representative of those which react quickly to produce chloroform under conditions in water treatment plants. Studies with model compounds, which are discussed in the section pertaining to chlorine chemistry, have shown

OCR for page 139
142 DRINKING WATER AND HEALTH that other types of compounds, including other ketones, may react more rapidly than the simple ketones. Humic Substances As was mentioned previously, it is an attractive assumption that naturally occurring humic substances, which are derived from the structural components of living and decaying plants and/or soil dissolution and runoff, provide the most ubiquitous source of haloform precursors in natural water systems. Only limited information is available concerning the structure of these complex natural products, and it is not yet known whether all the major structural features have been identified, if any structural differences exist among the hectic substances in waters from different geographic areas, and if these substances are closely or distantly related to soil humic and marine humic materials. The term "humic acid" is generic and refers to that fraction of soil organic material that is soluble in alkaline solutions but insoluble in acid and ethyl alcohol (Christman and Oglesby, 1971~. The fraction that is soluble in acid is commonly labelled "fulvic acid," and that material precipitated by acid but soluble in ethyl alcohol is "hymatomelanic acid." Soils vary widely in their relative compositions of these acids, but aquatic organic material behaves operationally as fulvic acid (Black and Christman, 1963), which typically contains more oxygen and less nitrogen than the humic acid fraction in both soil and aquatic organic matter. Marine organic matter (including sedimentary material) is derived largely from marine organisms and contains more sulfur than its fresh water equivalent (Nissenbaum and Kaplan, 1972; Stuermer and Harvey, 1978~. Christman and Oglesby (1971), Steelink (1977), Schnitzer and Kahn (1972), and Dubach et al. (1964) have reported the presence of carboxyl, phenolic and alcoholic hydroxyl, carboxyl, and methoxyl functional groups in humic material. It would appear that the more oxygenated fulvic acid fraction has a greater carboxyl acidity than the humic acid fraction. Whittaker and Likens (1973) estimated that 90~0 of the terrestrial biospheric carbon (standing biomass) is tied up in woody tissue. Lignin is a dominant (20~<~o) chemical entity in woody tissue. Because of its refractory nature, it is probably a principal precursor of soil humus, although a myriad of other natural products unquestionably contribute to the complex pool of soil organic matter. Lignin itself is a mixed polymer of guaiacyl (I), syringyl (II), end p-hydroxyphenylpropane (III) aromatic moieties:

OCR for page 139
The Chemistry of Disinfectants in Water 143 c3 c3 c3 ~ /[~\ ~ OCH3 CH3 O OCH3 OH OH OH I II III No other substitution patterns are known in nature and no other length of alkyl side chain has been found in lignin from any source. Oxidative degradation of lignin produces, therefore, only three aromatic substitu- tion patterns (I, II, and III), although the relative amounts of each vaIy among the gymnosperms, angiosperms, and the grasses. Intermonomeric linkages in the lignin macromolecule are of both carbon-to-carbon and ether linkage types. The largest single contributor is believed to be the ,8-4' ether configuration. Side-chain carbon atoms may be in various states of oxygenation or unsaturation, and may contain methyl ketone, allyl, and secondary alcohol configurations. Significant changes occur in the humification process as reflected by comparative functional group data for lignin and soil humic acid (Table III- 1~. This process, which is oxidative in nature, may strongly affect the characteristics of aquatic humic matenal. Microbial mediation is apparent when there is a marked decrease in methoxyl groups and increases in phenolic hydroxyl and carboxyl acidity. TABLE [it-] Comparative Functional Group Analysis of Soil Humic Acid and Spruce Lignina Group Content, mM/g Functional Group Soil Humic Acid Methoxyl Total hydroxyl Phenolic hydroxyl Alcoholic hydroxyl Carbonyl Carboxyl 5.1 6.2 1.6 4.6 1.0 Trace 86.0 0.2 5.1 2.9 2.2 5.5 a From Christman and Oglesby, 1971.

OCR for page 139
144 DRINKING WATER AND HEALTH The contribution of woody tissues to marine humus is not apparent from the results of degradative experiments on marine fulvic acids, which are considered to be autochthonous materials. Degradation of both soil humic acid and aquatic humic material reflects a partial lignitic origin (Table III-2), although a variety of other aromatic patterns (m-dihy- droxy) and aliphatic chain lengths (C~ Cay) must result from other natural product sources. The data in Table III-2 indicate key areas of inadequacy in our knowlege of the chemical nature of aquatic Ohmic substances. It is not possible to model natural aquatic humic material with a desirable degree of chemical accuracy, and it certainly is not possible to state that THM's, which appear in chlorinated water containing humic substances, are derived by the classic haloform reaction. The ultimate concern for public health protection is, of course, the fact that THM's are formed during the chlorination of drinking water sources. Consequently, a discussion of chemical mechanisms may appear to be rather academic. However, a precise understanding of the mechanisms by which the THM's are formed may prove to be truly beneficial by helping water utility personnel avoid the conditions during treatment that promote the appearance of high concentrations of these compounds in finished water. Studies with model compounds under well-defined laboratory conditions have been useful in elucidating these mechanisms and reaction conditions. Examples are given in the section pertaining to chlorine chemistry. CHLORINE Chlorine has been the principal disinfectant of community water supplies for several decades. Until recently, its use had never been questioned seriously because the health benefits derived from it were so obvious. Although an occasional taste-and-odor problem in finished water was attributable to the reaction of chlorine with some substance in the raw water, the events were usually intermittent, short-lived, and presumably did not affect the public health. However, in 1974, Rook (1974) in the Netherlands and Bellar et al. (1974) in the United States reported that chlorine reacts with organic precursors that are found in many source waters to produce a potential carcinogen, chloroform (CHC13~. In December 1974, Congress passed the Safe Drinking Water Act (PL 93-523), and in early 1975, the U.S. Environmental Protection Agency (EPA) began an 80-city water supply survey the National Organics Reconnaissance Survey (NORS) to determine the extent of the prob-

OCR for page 139
The Chemistry of Disinfectants in Water 145 lem (Symons et al., 1975~. As part of NORS, finished waters from five cities (Miami, Florida; Seattle, Washington; Ottumwa, Iowa; Philadel- phia, Pennsylvania; and Cincinnati, Ohio), which represented the major types of water sources in the United States, were analyzed as thoroughly as possible for all volatile organic compounds, i.e., those that can be stripped from solution by purging with an inert gas (Coleman et al., 19761. Seventy-two compounds were identified, 53% of them containing one or more halogens. A later study, the EPA National Organic Monitoring Survey (NOMS), included analyses of samples that had been taken from the water supplies of 113 cities (Brass et al., 1977) on four occasions over an 18-month period during 1976 and 1977. The source waters of a few cities were examined, but most of the effort was directed toward an analysis of finished waters for chloroform and 20 other volatile organic compounds. In addition to the 21 compounds that were ordinally selected, five others appeared frequently and were reported. Since 1974, there have been numerous other surveys similar to NORS and NOMS, but they have been more restricted in scope. In addition, research activity has been intensified to isolate and identify the precursors, products, and mechanisms that are associated with the presence of potentially toxic organic compounds in both water and wastewater. In December 1976, the EPA published a list of 1,259 compounds that had been identified in a variety of waters (including industrial effluents) in Europe and in the United States (Shackelford and Keith, 1976~. The agency is currently compiling a comprehensive register of all data concerning the identification of organic pollutants in water. Properties of Aqueous Chlorine Various aspects of chlorine chemistry have been reviewed by Jolley et al. (1978), Miller et al. (1978), Morris (1975, 1978), and Rosenblatt (1975~. A synopsis of the basic principles will provide some understanding of the various forms that chlorine can assume in water and the reactions that it can undergo with certain types of compounds. REACTIVE FORMS OF CHLORINE IN WATER "Aqueous chlorine" is a misleading term because the active form of chlorine that is present in treated water and wastewater is not the gaseous chlorine molecule (C12) but, rather, a hydrolysis product, hypochlorous acid (HOC1), which is formed from the reaction between the chlorine molecule and water: C12 + H2O = HOC1 + H+ + C1 `1)

OCR for page 139
146 to CSs _ .5 3 .0 ~ _ :r .O ~ Cd ~C .g ~ ^~ D := V, ~ O := o J!=l _ E ._ c - m - 3.o ,8 .g i_= ,, ~ ~ E a.~.Y Cot ._ o ,0 _ As-" ~ .~ ~ ~ o o _.D .g ~ o _ Cot a cO i_ ~ Came .m 5: .~ _ _ _ ,, c ~ ~ _ ~ _ ~ i) S as, 7 1 O _ ~ ~ .s ~ ~,C U, :^ ~ - o .5 ~ Cot .= ~ ~ S.O-~O 9 3~i ~ ~ . . ~ D ~ 0-~ g~ a, C~ c, ea ~ ~ . . 331 333 ti8-3~ ~ ~ ~ _ - o x ~ o~ ~ . .c o ~o X 8 -o . ,.. . ~ '; ~ ~ o . - . x o

OCR for page 139
147 at V\~.4 E9 -all= at i '- j 5 a 3 ~, ~ ~ R ~ sac a ~ a ~ - ~ ~ - ~ os e ~ ~ ~ R ~ Is ~ ~ ~ ~

OCR for page 139
148 DRINKING WATER AND HEALTH Hypochlorous acid, a weak acid, can ionize as follows: HOC1 = H+ + OC1 (2) The degree of ionization depends primarily on the pH and temperature of the water. The concentration of hypochlorous acid and the hypochlor- ite ion (OC1-) are approximately equal at pH 7.5 and 25C. Another form of chlorine, the hypochloronium acidium ion (H2OC1+), is known to exist (Miller et al., 1978; Rosenblatt, 1975), but its concentration would be extremely low in water at pH's between 5 and 9. Still another form of chlorine, the chloronium (or chlorinium) ion (C1+), has been proposed as an important reactant in aqueous solutions of organic compounds (Carlson and Caple, 1978), although its existence is disputed (Rosenblatt, 19751. Nevertheless, Morris (1978) pointed out that "the reactant behavior of HOC1 with organic carbon and amino nitrogen is as an electrophilic agent in which the chlorine atom takes on partially the characteristics of C1+ and combines with an electron pair in the substrate." Finally, Carlson and Caple (1978) mentioned that another form of chlorine, the chlorine radical (Coo), may react in the light to produce chlorine-substituted organic compounds when the parent chlorine molecule is not lost by any other significant reaction pathway. Rosenblatt (1975), citing others, described this form as "probably the most selective chlorinating species of all." Free chlorine species (HOC1, OC1-, C12, H2OC1+, C1+) will oxidize both the bromide ion (Br~) and iodide ion (I-) to hypobromous and hypoiodous acids (HOBr and HOI). This reaction, as will be discussed later, is postulated to account for the presence of bromine- and iodine- substituted organic compounds, particularly the mixed-halide haloforms, in waters that had been disinfected by chlorination. REACTIONS OF HYPOCHLOROUS ACID WITH ORGANIC COMPOUNDS Chlorine reacts in solutions of organic compounds by one or more of three basic mechanisms (Jolley et al., 1978; Miller et al., 1978; Morris, 1975; Morris, 1978), namely, addition, during which chlorine atoms are added to a compound; oxidation; and substitution, during which chlorine atoms are substituted for some other atom that is present in the organic reactant. All three of these reactions involve hypochlorous acid as an electrophile. Only addition and substitution reactions produce chlorinated organic

OCR for page 139
The Chemistry of Disinfectants in Water 149 compounds. Oxidation reactions account for most of the "chlorine demand" of natural waters and waste treatment effluents (Jolley et al., 1978; Morris, 1975), but the end products are not chlorinated organic compounds. That is not to say that those products cannot be harmful. Miller et al. (1978) have mentioned that epoxides can be produced from carbon-chlorinated compounds at pH values that are common in water treatment plants (e.g., pH 9.5-10.5) where softening is practiced. To illustrate, they describe the reaction between ethylene (COHN) and hypochlorous acid, which yields ethylene chlorohydrin (ClCH2CH2OH) as an intermediate. This hydrolyzes to form the epoxide, ethylene oxide (C2H4O). Carlson and Caple (1978) mentioned one such reaction, in which a mixture of chlorohydrins resulted from the reaction of oleic acid [CH3(CH2~7CH=CH(CH2~7COOH] with hypochlorous acid. Presum- ably, these would be converted to epoxides if the pH were to be increased. Carlson and Caple also showed how a ubiquitous natural compound, a-terpineol [CH3C6H4C(CH3~20H], could form epoxides when reacted with hypochlorous acid. These reactions illustrate how chlorination may result in the development of nonchlorinated products, e.g., the epoxides, which may pose health risks. In instances such as those just discussed, a chlorinated intermediate, which itself should be evaluated toxicologically, is involved. Chlorine By-Products Found in Drinking Water and Selected Nonpotable Waters The most frequently mentioned products of aqueous reactions between chlorine and selected types of organic compounds are discussed in this section. Special attention is given to the trihalomethanes (THM,s) because of the current interest in them as potentially hazardous by- products of chlorination in municipal water treatment facilities. The specific reactions by which THM's are produced in chlorinated natural waters are not well understood because the chemical structures of the precursor organic compounds, which are thought to be primarily heroic substances, are highly varied and extremely complex. A summary of the relevant facts concerning these ubiquitous, natural organic substances is presented in the section on precursors. The tea "haloform reaction" is often mentioned as the mechanism by which THM's are produced when natural waters are chlorinated. This has not been validated definitively in actual water treatment systems. However, the reaction will be discussed in conjunction with THM formation in natural waters because it is one possible mechanism that has been described thoroughly in the literature.

OCR for page 139
240 DRINKING WATER AND H"LTH Ejects, Vol. 2. Ann Arbor Science Publishers, Inc., Ann Arbor, Mich. 909 pp. Bellar, T.A., J.J. Lichtenberg, and R.C. Kroner. 1974. The occurrence of organohalides in chlorinated drinking waters. J. Am. Water Works Assoc. 66:703-706. Berliner, E. 1966. The current state of positive halogenating agents. J. Chem. Educ. 43: 124- 133. Black, A.P., W.C. Thomas, Jr., R.N. Kinman, W.P. Banner, M.A. Keirn, J.J. Smith, Jr., and A.A. Jabero. 1968. Iodine for the disinfection of water. J. Am. Water Works Assoc. 60:69-83. Bunn, W.W., B.B. Haas, E.R. Deane, and R.D. Kleopfer. 1975. Formation of tnhalometh- anes by chlorination of surface water. Environ. Lett. 10:205-213. Chang, S.L. 1958. The use of active iodine as a water disinfectant. J. Am. Pharm. Assoc. 47:417-423. Engel, P., A. Oplatka, and B. Perlmutter-Hayman. 1954. The decomposition of hypobrom- ite and bromite solutions. J. Am. Chem. Soc. 76:2010~2015. Environmental Health Directorate. 1977. National Survey for Halometh~nes in Dnnking Water. Department of National Health and Welfare, Health Protective Branch, Ottawa, Canada. Publ. No. 77-EHD. 119 pp. Freund, G., W.C. Thomas, Jr., E.D. Bird, R.N. Kinman, and A.P. Black. 1966. Effect of iodinated water supplies on thyroid function. J. Clin. Endocrinol. Metab. 26:619-624. Gilow, H.M., and J.H. Ridd. 1973. Mechanism of aromatic bromination by hypobromous acid in aqueous perchlonc acid. Kinetic evidence against the prior formation of 'positive bromine.' J. Chem. Soc. Lond. Perkin Trans. 2: 1321-1327. Goodenough, R.D., J.F. Mills, and J. Place. 1969. Anion exchange resin (polybromide form) as a source of active bromine for water disinfection. Environ. Sci. Technol. 3:85= 856. Helz, G.R., and R.Y. Hsu. 1978. Volatile chloro- and bromocarbons in coastal waters. Limnol. Oceanogr. 23:858- 869. Henderson, J.R., G.R. Peyton, and W.H. Glaze. 1976. A convenient liquid-liquid extraction method for the determination of halomethanes in water at the parts-per- billion level. Pp. 105-111 in L.H. Keith, ed. Identification ~ Analysis of Organic Pollutants in Water. Ann Arbor Science Publishers, Inc., Ann Arbor, Mich. Kuehl, D.W., G.D. Veith, and E.N. Leonard. 1978. Brominated compounds found in waste-treatment effluents and their capacity to bioaccumulate. Pp. 17~192 in R.L. Jolley, H. Gorchev, and D.H. Hamilton, Jr., eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 2. Ann Arbor Science Publishers, Inc., Ann Arbor, Mich. 909 pp. Johnson, J.D., and R. Overby. 1971. Bromine and bromamine disinfection chemistry. J. Sanit. Eng. Div., Am. Soc. Civ. Eng. 97:617-628. LaPointe, T.F., G. Inman, and J.D. Johnson. 1975. Kinetics of tribromamine decomposi- tion. Pp. 301-338 in J.D. Johnson, ed. Disinfection: Water and Wastewater. Ann Arbor Science Publishers, Inc., Ann Arbor, Mich. 425 pp. Laubusch, E.J. 1971. Chlonnation and other disinfection processes. Pp. 15~224 in American Water Works Association. Water Quality and Treatment. A Handbook of Public Water Supplies, 3rd ed. McGraw-Hill, New York. Livingstone, D.A. 1963. Chemical Composition of Rivers and Lakes. U.S. Geological Survey Professional Paper 440 G. Washington, D.C. 64 pp. Macalady, D.L., J.H. Carpenter, and C.A. Moore. 1977. Sunlight-induced brom~te formation in chlorinated seawater. Science 195: 1335-1337.

OCR for page 139
The Chemistry of Disinfectants in Water 241 Mills, J.F. 1975. Interhalogens and halogen mixtures as disinfectants. Pp. 113-143 in J.D. Johnson, ed. Disinfection: Water and Wastewater. Ann Arbor Science Publishers, Ann Arbor, Mich. 425 pp. Moelwyn-Hughes, E.A. 1971. The Chemical Statics and Kinetics of Solutions. Academic Press, New York. 530 pp. Morris, J.C., S.L. Chang, G.M. Fair, and G.H. Conant, Jr. 1953. Disinfection of drinking water under field conditions. Ind. Eng. Chem. 45: 1013-1015. Pauling, L. 1960. The Nature of the Chemical Bond, and the Structure of Molecules and Crystals: An Introduction to Modern Structural Chemistry, 3rd ed. Cornell University Press, Ithaca, N.Y. 644 pp. Rickabaugh, J.F., and R.N. Kinman, 1978. Tnhalomethane formation from iodine and chlorine disinfection of Ohio River water. Pp. 583-591 in R.L. Jolley, H. Gorchev, and D.H. Hamilton, Jr., eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 2. Ann Arbor Science Publishers, Inc., Ann Arbor, Mich. 905 pp. Rickabaugh, J.F. 1977. The study of trihalomethane formation when iodine is used for disinfection of drinking water. M.S. thesis. University of Cincinnati, Cincinnati, Ohio. llOpp. Rook, J.J. 1974. Formation of haloforms during chlorination of natural waters. Water Treat. Exam. 23:234-243. Rook, J.J., A.A. Gras, B.G. van der Heijden, and J. de Wee. 1978. Bromide oxidation and organic substitution in water treatment. J. Environ. Sci. Health A13:91-116. Shackleford, W.M., and L.H. Keith. 1976. Frequency of Organic Compounds Identified in Water. EPA-600/476~62. U.S. Environmental Protection Agency, Environmental Research Laboratory, Athens, Ga. 629 pp. Sugam, R.J. 1977. Chlorine degradation in estuarine waters. Ph.D. dissertation. University of Maryland, College Park, Md. 221 pp. Swain, C.G., and D.R. Crist. 1972. Mechanisms of chlonnation by hypochlorous acid. The last of chlonnium ion, C1 + . J. Am. Chem. Soc. 94:3195-3200. Turekian, K.K. 1971. Rivers, tributaries, and estuaries. Pp. 9-73 in D.W. Hood, ed. Impingement of Man on the Oceans. Wiley Interscience Publishers, New York. White, G.C. 1972. Handbook of Chlorination. Van Nostrand Reinhold, New York. 744 pp. Chlorine Dioxide Beuermann, L. 1965. Preparation of chlorine dioxide from sodium chlonte and hydrochlo- ric acid. Gas-Wasserfach. 106:783-788. Bowen, E.J., and W.M. Cheung. 1932. The photodecomposition of chlorine dioxide solutions. J. Chem. Soc. Lond. 1932(Part D: 120~1208. Bray, W. 1906. Beitrage zur Kenntnis der Halogensauerstoffverbindungen. Abhandlung III. Zur Kenatnis des Chlordioxyds. Z. Physik. Chem. 54:569-608. Buydens, R. 1970. Ozoni~ation and its effects on the mode of purification of river waters. (In French) Trib. CEBEDEAU 23:319- 320, 286-291. Dence, C.W., and K.V. Sarkanen. 1960. A proposed mechanism for the acidic chlorination of softwood lignin. Tappi 43:87-96. Dence, C.W., M.K. Gupta, and K.V. Sarkanen. 1962. Studies on oxidative delignification mechanisms. Part II. Reactions of vanillyl alcohol with chlorine dioxide and sodium chlorite. Tappi 45:29-38.

OCR for page 139
242 DRINKING WATER AND H"LTH Dowling, L.T. 1974. Chlonne dioxide in potable water treatment. Water Treat. Exam. 23(2): 190-204. Feuss, J.V. 1964. Problems in the determination of chlorine dioxide residuals. J. Am. Water Works Assoc. 56:607- 615. Flis, I.E. et al. 1955. Trans. Leningr. Techn. Inst. Tsell, B,~ma~hu Prom. 16:62-67. Fuchs, W., and H. Leopold. 1927. Hum~c acids. II. The action of bromine, thionyl chloride and chlorine dioxide on artificial humic acids. BrennstoffChem. 8: 101-103. Fujii, M., and M. Ukita. 1957. Mechanism of wheat protein coloring by chlorine dioxide. Nippon Nogei Kagaku Kaishi 31: 101-109. Gall, R.J. 1978. Chlorine dioxidean overview of its preparation, properties and uses. Pp. 356-382 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute, Inc., and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Glabisz, U. 1968. The Reaction of Chlonne Dioxide with Components of Phenolic WastewatersA Summary. Monograph 44. Wyd. Uczln. Politech., Szczecin, Poland. 127 pp. Glabisz, U. 1967. Action of chlonne dioxide on monohydric phenols. Chem. Tech. (Berlin) 19:352-355. Gordon, G., and F. Feldman. 1964. Stoichiometry of the reaction between uranium (IV) and chlorite. J. Inorg. Chem. 3: 1728-1733. Gordon, G., R.G. Kieffer, and D.H. Rosenblatt. 1972. The chemistry of chlonne dioxide. Pp. 201-286 in S.J. Kippard, ed. Progress in Inorganic Chemistry, Vol. 15. John Wiley Sons, Inc., New York. Granstron, M.L., and G.F. Lee. 1957. Rates and mechanisms of reactions involving oxy- chloro compounds. Public Works 88:90-92. Granstrom, M.L., and G.F. Lee. 1958. Generation and use of chlorine dioxide in water treatment. J. Am. Water Works Assoc. 50: 1453-1466. Hodgen, H.W., and R.S. Ingols. 1954. Direct colorimetric method for the determination of chlorine dioxide in water. Anal. Chem. 26: 1224-1226. Jeanes, A., and H.S. Isbell. 1941. Chemical reactions of the chlontes with carbohydrates. J. Res. Natl. Burl Stand. 27: 12~142. Kennaugh, J. 1957. Action of diaphanol on arthropod cuticles. Nature 180:238. Kieffer, R.G., and G. Gordon. 1968. Inorg. Chem. 7:235-238, 239-244. Leopold, B., and D.B. Mutton. 1959. The effect of chlorinating and oxidizing agents on derivatives of oleic acid. Tappi 42:21~225. Lindgren, B.O., and B. Ericsson. 1969. Reaction of chlorine dioxide with phenols: formation of a,,6 epoxy ketones from mesitol and 2,6-xylenol. Acta Chem. Scand. 23:3451- 3460. Lindgren, B.O., and T. Nilsson. 1972. Lignin reactions during chlorine dioxide bleaching of pulp. Oxidation by chlorite. Sven. Papperstidn. 75: 161-168. Lindgren, B.O., and C.M. Svahn. 1966. Reactions of chlorine dioxide with unsaturated compounds. II. Methyl oleate. Acta Chem. Scand. 20:211-218. Lindgren, B.O., C.M. Svahn, and G. Widmark. 1965. Chlorine dioxide oxidation of cyclohexene. Acta Chem. Scand. 19:7-13. Love, O.T., Jr., J.K. Carswell, R.J. Miltner, and J.M. Symons. 1976. Treatment for the prevention of removal of trihalomethanes in drinking water. In J.M. Symons. Interim Treatment Guide for the Control of Chloroform and Other Trihalomethanes. Water

OCR for page 139
The Chemistry of Disinfectants in Water 243 Supply Research Division, Municipal Environmental Research Laboratory, U.S. Environmental Protection Agency, Cincinnati, Ohio (App. 3). Mallevialle, J. 1976. Ozonation des substances de type humique ions les eaux. Pp. 262-270 in R.G. Rice, P. Pichet, and M.A. Vincent, eds. Proceedings of the 2nd International Conference on Ozone Technology. International Ozone Institute, Cleveland, Ohio. Masschelein, W. 1967. Development in the chemistry of chlorine dioxide and its applications. Chim. Ind. Genie Chim. 97:49-61. Masschelein, W. 1969. Les oxydes de chlore et le chlorite de sodium. Monogr. Dunod 74: 1~57. Miller, G.W., R.G. Rice, C.M. Robson, W. Kuhn, and H. Wolf. 1978. An assessment of ozone and chlorine dioxide technologies for treatment of municipal water supplies. Pp. 9-57 to 9-89 in Report of EPA Grant R804385-01. Municipal Environmental Research Laboratory, Office of Water Supply, U.S. Environmental Protection Agency, Cincinnati, Ohio. Miltner, R.J. 1977. Measurement of chlorine dioxide and related products. In Proceedings, American Water Works Association Water Quality Technology Conference, San Diego, Calif., Dec. 6-7, 1976. Paper No. 2A-5. American Water Works Association, Denver, Colo. Otto, J., and K. Paluch. 1965. Reactions of chlorine dioxide with some organic compounds. V. Reaction of benzaldehyde with chlorine dioxide. Roczniki Chem. 39:1711-1712. Paluch, K. 1964. The reaction of chlorine dioxide with phenols. I. Phenol and chlorophenols. II. Hydroquinone, chloro derivatives of hydroquinone, and nitrophenols. Rocznicki Chem. 38:35~2, 43~6. Paluch, K., J. Otto, and K. Kozlowski. 1965. Reaction of chlorine dioxide with some organic compounds. VI. Reaction of benzyl alcohol with chlorine dioxide and with acidified sodium chlorite solution. Rocznicki Chem. 39: 1603-1608. Reichert, J.K. 1968a. Kanzerogene Substanzen in Wasser und Boden. XXI. Die Entlernung polyzyklischer Aromaten bei der Trinkwasser-Aufbereitung durch Chlordi- oxid: Quantitative Befunde. Arch. Hyg. 152:37~4. Reichert, J.K. 1968b. Kanzerogene Substanzen in Wasser und Boden. XXIII. Die Entfernung polyyklischer Aromaten bei der Trinkwasseraufbereitung durch Isolierung und Identifizierung der 3,~Benzpyrenfolgeprodukte. Arch. Hyg. 152:265-276. Robson, H.L. 1964. Pp. 35-50 in H.F. Mark, J.J. McKetta, Jr., and D.F. Othmer, eds. Kirk- Othmer Encyclopedia of Chemical Technology. Vol. 5, 2nd ed. Interscience Publishers, New York. Rosenblatt, D.H. 1975. Chlorine and oxychlorine species reactivity with organic sub- stances. Pp. 249-276 in J.D. Johnson, ed. Disinfection: Water and Wastewater. Ann Arbor Science Publishers, Inc., Ann Arbor, NIich. 425 pp. Rosenblatt, D.H. 1978. Chlorine dioxide: chemical and physical properties. Pp 332-343 in R.G. Rice and J.A Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmen- tal Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Sarkanen, K.V., K. Kakehi, R.A. Murphy, and H. White. 1962. Studies on oxidative delignification mechanisms. Part I. Oxidation of vanillin with chlorine dioxide. Tappi 45:24-29. Sarkar, P.B. 1935. Chemistry of jute lignin. VII. Behaviour of organic compounds towards chlorine dioxide and its significance on the constitution of lignin. J. Indian Chem. Soc. 12:470~82.

OCR for page 139
24Ul DRINKING WATER AND H"LTH Schmidt, E., and K. Braunsdorf. 1922. Natural proteins. I. Behavior of chlorine dioxide towards organic compounds. Ber. 55B: 1529-1534. Somsen, R.A. 1960. Oxidation of some simple organic molecules with aqueous chlorine dioxide solutions. I. Kinetics. II. Reaction products. Tappi 43: 154-156, 157- 160. Spinks, J.W.T., and J.M. Porter. 1934. Photodecomposition of chlorine dioxide. J. Am. Chem. Soc. 56:26~270. Stevens, A.A., D.R. Seeger, and C.J. Slocum. 1978. Products of chlorine dioxide treatment of organic materials in water in ozone/chlorine oxidation products of organic materials. Pp. 383-399 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Sussman, S., and J.S. Rauh. 1978. Use of chlorine dioxide in water and waste~vater treatment. Pp. 34~355 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Symons, J.F., J.K. Carswell, R.M. Clark, P. Dorsey, E.E. Geldreich, W.P. Heffernam, J.C. Hoff, O.T. Love, L.J. McCabe, and A.A. Stevens. 1977. Ozone, Chlorine Dioxide, and Chloramines as Alternatives to Chlorine for Disinfection of ~inking Water: State of the Art. U.S. Environmental Protection Agency, Water Supply Research Division, Cincinnati, Ohio. 84 pp. Taylor, M.C., J.F. White, G.P. Vincent, and G.L. Cunningham. 1940. Sodium chlorite, properties and reactions. Ind. Eng. Chem. 32:899~903. Thielemann, H. 1972. Uber die Einwirkung von Chlordioxid auf einige polycyklische aromatische Kohlenwasserstoffe. Mikrochim. Acta 575-577. Toussaint, M. 1972. Chlorine dioxide in drin~ng water treatment. Trib. CEBEDEAU 25(342):260 266. Vilagenes, R., A. Monteil, A. Derremaux, and M. I ~mbert. 1977. A comparative study of halomethane formation during drinking water treatment by chlorine or its derivatives in a slow and sand filtration plant and in wastewater treatment plants. Paper presented at 96th Annual Conference, American Water Works Association, Anaheim, Calif., May 8, 1977. White, J.F., M.C. Taylor, and G.P. Vincent. 1942. The chemistry of chlorites. Ind. Eng. Chem. 34:782-792. Ozone Reactions and Products Ahmed, M., and C.R. Kinney. 1950. Ozonation of humic acids prepared from oxidized bituminous coal. J. Am. Chem. Soc. 72:559-561. Bailey, P.S. 1975. Reactivity of ozone with various organic functional groups important to water purification. Pp. 101-119 in R.G. Rice and M.E. Browning, eds. First International Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn. Bauch, H., and H. Burchard. 1970. Untersuchungen uber die Einw~rkung von Ozon auf Wasser mit geringen Verunreinigungen. Wasser Luft Beitr. 14:270-273.

OCR for page 139
The Chemistry of Disinfectants in Water 245 Bauch, H., H. Burchard, and H.M. Arsovic. 1970. Ozone as an oxidant for phenol degradation in aqueous solutions. Gesund. Ing. 91(9):258-262. Bollyky, L.J. 1975. Ozone treatment of cyanide and plating wastes. Pp. 522-532 in R.G. Rice and M.E. Browning, eds. First International Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn. Briner, E. 1959. Photochemical production of ozone. Pp. 1-6 in Ozone Chemistry and Technology. Advances in Chemistry Series No. 21. American Chemical Society, Washington, D.C. Brody, S.S. 1975. A proposed new analysis for ozone in water using a field portable chemiluminescent ozone analyzer. Pp. 84-92 in R.G. Rice and M.E. Browning, eds. First International Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn. Carlson, R.M., and R. Caple. 1977. Chemical/Biological Implications of Using Chlorine and Ozone for Disinfection. U.S. Environmental Protection Agency, Environmental Research Laboratory, Duluth, Minn. Report No. EPA/600/3-77/066. 99 pp. Cerkinsky, S.N., and N. Trahtman. 1972. The present status of research on the disinfection of drinking water in the USSR. Bull. WHO 46:277-283. Chian, E.S.K., and P.P.K. Kuo. 1976. Fundamental study on the post-treatment of RO permeates from army wastewater. Second Annual Summary Report, Report No. UILU- ENG-76-2019. U.S. Army Medical R ~ D Command, Washington, D.C. Criegee, R. 1959. Products of ozonization of some olefins. Pp. 13~135 in Ozone Chemistry and Technology. Advances in Chemistry Series No. 21. American Chemical Society, Washington, D.C. Dobinson, F. 1959. Ozonization of malonic acid in aqueous solution. Chem. Ind. Lond. 26:853-854. Eisenhauer, H.R. 1968. The ozonization of phenolic wastes. J. Water Pollut. Control Fed. 40: 1887-1899. FaLk, H.L., and J.E. Moyer. 1978. Ozone as a disinfectant of water. Pp. 38-58 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Press International, Cleveland, Ohio. 487 pp. Garrison, R.L., C.E. Mauk, and H.W. Prengle, Jr. 1975. Advanced ozone-oxidation system for complexed cyanides. Pp. 551-577 in R.G. Rice and M.E. Browning, eds. First International Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn. Gilbert, E. 1976. Ozonolysis of chlorophenols and maleic acid in aqueous solution. Pp. 25~261 in R.G. Rice, P. Pichet, and M.A. Vincent, eds. Proceedings of the Second International Symposium on Ozone Technology, Montreal, Canada, May 11-14, 1975. Ozone Press International, Jamesville, N.Y. 725 pp. Gilbert, E. 1978. Reactions of ozone with organic compounds in dilute aqueous solution: identification of their oxidation products. Pp. 227-242 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Gould, J.P., and W.J. Weber, Jr. 1976. Oxidation of phenols by ozone. J. Water Pollut. Control Fed. 48:47 60. .L

OCR for page 139
246 DRINKING WATER AND H"LTH Gunther, F.A., D.E. Ott, and M. Ittig. 1970. The oxidation of parathion to paraoxon. II. By use of ozone. Bull. Environ. Contam. Toxicol. 5:87-94. Helz, G.R., R.Y. Hsu, and R.M. Block. 1978. Bromoform production by oxidative biocides in marine waters. Pp. 68-76 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Hoigne, J., and H. Bader. 1975. Ozonation of water: role of hydroxyl radicals as oxicl~ng intermediates. Science 190:782-784. Hoigne, J., and H. Bader. 1976. Identification and kinetic properties of the oxidizing decomposition products of owne in water and its impact on water purification. Pp. 271- 282 in R.G. Rice, P. Pichet, and M.A. Vincent, eds. Proceedings of the Second International Symposium on Ozone Technology, Montreal, Canada, May 11-16, 1975. Ozone Press International, Jamesville, N.Y. 725 pp. Hoigne, J., and H. Bader, 1977. Rate constants for the reactions of ozone and organic pollutants and ammonia in water. Symposium on Advanced-Ozone Technology. International Ozone Institute, Toronto, Ontario, Canada. Hoigne, J., and H. Bader. 1978a. Ozone initiated oxidations of solutes in wastewater. A reaction kinetic approach. Paper presented at International Conference on Water Pollution, Stockholm, Sweden. Hoigne, J., and H. Bader. 1978b. Ozonation of water: kinetics of oxidation of ammonia by ozone and hydroxyl radicals. Environ. Sci. Technol. 12:79 84. Huibers, D.T.A., R. McNabney, and A. Halfon. 1969. Ozone treatment of secondary effluents front wastewater treatment plants. Federal Water Pollution Control Adminis- tration, U.S. Department of the Interior, Cincinnati, Ohio. Robert A. Taft Water Research Center Report No. TWRC4. 62 pp. Ingots, R.S. 1978. Ozonation of seawater. Pp. 77-81 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Jurs, R.H. 1966. Die Wirkung des Ozons auf in Wasser geloste Stoffe. Fortschr. Wasserchem. Ihrer Grenzgeb., Heft 4:4~64. Kilpatrick, M.L., C.C. Herrick, and M. Kilpatrick. 1956. The decomposition of ozone in aqueous solution. J. Am. Cbem. Soc. 78: 1784 1789. Kinman, R.N., J. Rickabaugh, V. Elia, K. McGinnis, T. Cody, S. Clark, and R. Christian. 1978. Effect of ozone on hospital wastewater cytotoxicity. Pp. 97-114 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Kinney, C.R., and L.D. Friedman. 1952. Ozonization studies of coal constitution. J. Am. Chem. Soc. 74:57~1. Kjos, D.J., R.R. Furgason, and L.L. Edwards. 1975. Ozone treatment of potable water to remove iron and manganese: preliminary pilot plant results and economic evaluation. Pp. 194-203 in R.G. Rice and M.E. Browning, eds. First International Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn.

OCR for page 139
The Chemistry of Disinfectants in Water 247 Klein, M.J., R.I. Brabets, and L.C. Kinney. 1975. Generation of ozone. Pp. 1-9 in R.G. Rice and M.E. Browning, eds. First Internatinal Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn. Kuo, P.P.K., E.S.K. Chian, and B.J. Chang. 1977. Identification of end products resulting from ozonization and chlorination of organic compounds commonly found in water. Environ. Sci. Technol. 11: 1177-1181. Lawrence, J. 1977. Identification of ozonization products in natural waters. Presented at the Symposium on Advanced Ozone Technology. International Ozone Institute, Toronto, Ontario, Canada. Lawrence, J., and F.P. Cappelli. 1977. Ozone in drinking water treatment: a review. Sci. Total Environ. 7:99-108. Maggiolo, A. 1978. Ozone's radical and ionic mechanisms of reaction with organic compounds in water. Pp. 59-67 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Mallevialle, J. 1975. Action de ['ozone dans la degradation des composes phenoliques simples et polymerizes: Application aux matieres h~niques contenues dans les eaux. Tech. Sci. Munic. Revue l'Eau 70: 107- 113. Mallevialle, J., Y. Laval, M. Lefebvre, and C. Rousseau. 1978. The degradation of humic substances in water by various oxidation agents (ozone, chlorine, chlorine dioxide). Pp. 189-199 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held at Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Manley, T.C., and S.J. Niegowski. 1967. Ozone. Pp. 41~432 in Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 14, 2nd ed. Interscience Publishers, New York. Mathieu, G.I. 1975. Application of film layer purifying chamber process to cyanide destructiona progress report. Pp. 533-550 in R.G. Rice and M.E. Browning, eds. First International Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn. Miller, G.W., and R.G. Rice. 1978. Testimony before House Science and Technology Committee, Subcommittee on the Environment and the Atmosphere (transcript by private co~unication). Murray, R.W. 1968. Ozone chemistry of organic compounds. Pp. 1 - in F.R. Mayo, ed. Oxidation of Organic Compounds. III. Ozone Chemistry Photo and Singlet Oxygen and Biochemical Oxidation. Advances in Chenustry Series No. 77. American Chemical Society, Washington, D.C. Netzer, A., and A. Bowers. 1975. Removal of trace metals from wastewater try lime and ozonation. Pp. 731-747 in R.G. Rice and M.E. Browning, eds. First International Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn. Oehlschlaeger, H.F. 1978. Reactions of ozone with organic compounds. Pp. 2(~37 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection A~ency. Ozone Press International, Cleveland, Ohio. 487 pp.

OCR for page 139
248 DRINKING WATER AND H"LTH . Rice, R.G. 1977. Reaction products of organic materials with ozone and with chlorine dioxide in water. Presented at International Ozone Institute Symposium on Advanced Ozone Technology, Toronto, Ontario, Canada. Rice, R.G., and J.A. Cotruvo. 1978. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmen- tal Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Rice, R.G., C. Gomella, and G.W. Miller. 1978. Rouen, France water treatment plant: Good organics and ammonia removal with no need to regenerate carbon beds. Civil Eng. ASCE (N.Y.) 48(5):76-82. Richard, Y., and L. Brener. 1978. Organic materials produced upon ozonization of water. Pp. 169-188 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 17-19, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Rogozhkin, G.I., T. Vsesayyzn, and I. Nauchno. 1970. Inta vodosnabzheniya kanalizatsii. Pp. 27~5 in Gidrotekhnicheskikh Sooruzheniy i Gidrogeologii. Schalekamp, M. 1978. Experiences in Switzerland with ozone particularly in connection with the charge of undesirable elements present in water. Ozone Technology Symposium and Exposition. International Ozone Institute, Los Angeles, Calif. Selm, R.P. 1959. Ozone oxidation of aqueous cyanide waste solutions in stirred batch reactors and packed towers. Pp. 6~77 in Ozone Chemistry and Technology. Advances in Chemistry Series No. 21. American Chemical Society, Washington, D.C. Shevchenko, M.A., and P.N. Taran. 1966. Investigation of the ozonolysis products of humus materials. Sov. Prog. Chem. 32:408~10. [Trans. of Ukr. Khim Zn. 32(5):532- 536.] Sievers, R.R., R.M. Barkley, G.Z. Eiceman, R.H. Shapiro, H.F. Walton, K.J. Kolonko, and L.R. Field. 1977a. Environmental trace analysis of organics in water by glass capillary column chromatography and ancillary techniques. J. Chromatogr. 142:745-754. Sievers, R.E., R.M. Barkley, G.A. Eiceman, L.P. Haack, R.H. Shapiro, and H.F. Walton. 1977b. Generation of volatile organic compounds from non-volatile precursors in water by treatment w~th chlorine or ozone. Presented at Conference on Water Chlorination, Gatlinsburg, Tenn. Sievers, R.E., R.H. Shapir~, H.F. Walton, G.A. Eiceman, and R.M. Barkley. 1977c. High resolution gas chromatographic determination of organic compounds in ozonized wastewater. Presented at ACS National Meeting, Chicago, Ill. Singer, P.C., and W.B. Zilli. 1975. Ozonation of ammonia: application to wastewater treatment. Pp. 269~287 in R.G. Rice and M.E. Browning, eds. First International Symposium on Ozone for Water and Wastewater Treatment. International Ozone Institute, Waterbury, Conn. Spanggord, R.J., and V.J. McClurg. 1978. Ozone methods and ozone chemistry of selected organics in water. 1. Basic chemistry. Pp. 115-125 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chlorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 15-17, 1976. Sponsored by the International Ozone Institute and the U.S. Environmental Protection Agency. Ozone Press International, Cleveland, Ohio. 487 pp. Stumm, W. 1954. Der Zerfall von Ozon in wassriger Losung. Helv. Chim. Acta 37:773-778. Sturrock, M.G., E.L. Cline, and K.R. Robinson. 1963. The ozonation of phenanthrene with water as participating solvent. J. Org. Chem. 28:234~2343.

OCR for page 139
The Chemistry of Disinfectants in Water 249 Symons, J., J.K. Carswell, R.M. Clark, P. Dorsey, E.E. Geldreich, W.P. Heffernam, J.C. Hoff, O.T. Love, L.J. McCabe, and A.A. Stevens. 1977. Ozone, Chlorine Dioxide and Chloramine as Alternatives to Chlorine for Disinfection of Water: State of the Art. Water Supply Research Division, U.S. Environmental Protection Agency, Cincinnati, Ohio. 84 pp. Well, L., B. Sttruif, and K.E. Quentin. 1977. Reaction mechanisms upon reaction of organic substances in water with ozone. Presented at the International Symposium on Ozone and Water, Berlin. International Ozone Institute, Cleveland, Ohio. Westgate Research Corp. 1978. The continued investigation into the chemistry of the UV- ozone water purification process. Westgate Research Corporation. Wynn, C.S., B.S. Kirk, and R. McNabney. 1973. Pilot plant for tertiary treatment of wastewater with ozone. U.S. Environmental Protection Agency, Washington, D.C. No. EPA-R2-73-146. 229 pp. Yocum, F.H. 1978. Oxidation of styrene with ozone in aqueous solution. Pp. 243-263 in R.G. Rice and J.A. Cotruvo, eds. Ozone/Chiorine Dioxide Oxidation Products of Organic Materials. Proceedings of a Conference held in Cincinnati, Ohio, November 15-17, 1976. Sponsored by the International Ozone Institute and the U.S. Environmen- tal Protection Agency. Ozone Press International, Cleveland, Ohio. Yokoyama, K., S. Sato, I. Yoshiyasu, and T. Imamura. 1974. Degradation of organic substances in water, by ozone. Mitsubishi Denki Giho Tech. Rev. 48: 1233-1238. .

OCR for page 139