Appendix A Chemical Formulae of Compounds Cited in this Book NAME MOLECULAR FORMULA STRUCTURAL FORMULA ACENAPHTHENE C 12 H 10 & 0-... 1/ ACENAPHTHYLENE CI2 He " " 00 1/ / 0 " ACETONE C3 H60 CH3-C-CH3 ACETYLENE He := CH ACROLEIN C 3 H4 0 CH2oCH-CH=O CI CI ALDRIN C I2 He CI 6 CI CI OH m-ALKYLPHENOLS RC 6 OH 5 0 0-... R ALLYLALCOHOL C 3 H6 0 CHz;::.CH-CHz-OH m- AMINOPHENOL C6 H 7 NO 0 0-... NH 2
48
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Appendix A Chemical Formulae of Compounds
Cited in this Book
NAME MOLECULAR FORMULA STRUCTURAL FORMULA
ACENAPHTHENE C 12 H 10 & 0-... 1/
ACENAPHTHYLENE CI2 He " " 00 1/ /
0
" ACETONE C3 H60 CH3-C-CH3
ACETYLENE He := CH
ACROLEIN C3 H4 0 CH2oCH-CH=O
CI
CI
ALDRIN CI2 He CI 6 CI
CI
OH
m-ALKYLPHENOLS RC 6 OH 5 0 0-... R
ALLYLALCOHOL C3 H6 0 CHz;::.CH-CHz-OH
m- AMINOPHENOL C6H7 NO 0 0-... NH 2
Appendix A 245
NAME MOLECULAR FORMULA STRUCTURAL FORMULA
OH
m-AMYLPHENOL CII HI60 0 /- CHz - (CHzl, - CH,
ANILINE C6 H7 N 0 ANTHRACENE CI4 HIO CCCJ :0.... :0.... I /-
BENZ (A) ANTHRACENE CIS HI2
BENZENE C 6 HI2 0
BENZYLCHLORIDE C7 H7 CI Cr BENZO (B)
C20 HI2 FLUORANTHENE
BENZO (J) C20 HI2 FLUORANTHENE
BENZO (K) C20 HI2 FLUORANTHENE
BENZOFURAN C s H6 0 (IL] :0.... I I
COOH
BENZOIC ACID C7 H6 O2 en
246
NAME MOLECULAR FORMULA
iso-BUTANOL
BUTENE
BUTYLENE C4 Ha
1,4-BUTYLPHENOL C1O HI4 O
CAPROLACTAM C6 HII NO
CARBON TETRACHLDRIDE CCI 4 (Tetrachloromethane)
CARBONYL SULPHIDE COS
CAROTENE C40 H56
CHLORANIL C6 0 2CI 4
CHLORDANE C'OH 6 Cl a
Appendix A
STRUCTURAL FORMULA
~H.
CH.- ~-OH
CH.
CH.-CH.CH-CH.
OH
0 C(CH.).
~ 0
0 CI I
CI-C-CI I CI
s·c.o
0
Clt)C' CI CI
0
CI CI
C'~;(:t' Icci. CI
CI
Appendix A
NAME
BENZO (GHI) PERYLENE
BENZO(A)PYRENE
BENZO (E) PYRENE
BENZOTHIOPHENE
BICYCLOOCTANE
BISPHENOL A
BROMODICHLORtlMETHANE
BROMOETHYLPROPANE
BROMOFORM
BROMOMETHANE
MOLECULAR FORMULA
C20HI2
CeHsS
Ce HI4
CIS HIS 0 2
CHCI 2Br
Cs HII Br
CHBr 3
CH3 Br
247
STRUCTURAL FORMULA
CC> ~ ~
<t> o-CHU-HO '/ _ '\ i '/ _ '\ OH
CH,
H I
CI-C-Br I CI
Br I
H C-C-CH 'I '
C H2CH 3
H I
8r -c - Br I Br
H I
H-C-Br I H
248
NAME MOLECULAR FORMULA
CHLOROETHYLENE
CHLOROETHYLVINYLETHER C 4 H7 0CI
CHLOROFORM
CHLOROMETHANE
CHLOROMETHYLMETHYLETHER C2 HS 0 CI
CHLOROMETHYL GUAIACOL
CHLOROMETHYL PHENOL
CHLOROMETHYLVERATROLE C9 HII O2 CI
CHLORQNAPHTHALENE
o-CHLORONITROBENZENE Cs H4 CI N02
Appendix A
STRUCTURAL FORMULA
CI-CHZ-CHZ-O-CH; CH z
CI I
CI-C - H I CI
H I
H - C - H I CI
OH
CH3~
Y CI
CI
~ VJ
Appendix A
NAME MOLECULAR FORMULA
CHLORDENE
CHLORDENE EPOXIDE
CHLOROBENZENE
m-CHLOROBENZOIC ACID C7 H5 CIO Z
CHLOROBIPHENYL
CHLORODECANE
CHLORODIBENZOFURAN C IZ He OCI
CHLORODIBROMOMETHANE CH BrzCI
CHLORODIFLUOROMETHANE CH CI F z
CHLOROETHANE
249
STRUCTURAL FORMULA
<f' H ~,C'C~,
CI CI ~ H H
£/H CI~CI~:
CI CI H 0
COOH o VCI
o
H I
CI-C-Br I Or
H I
CI-C-F I F
H I
CH3-~-CI
H
250
NAME MOLECULAR FORMULA
o-CHLOROPHENOL
2 -CHLOROPROPANE
CHLOROPROPENE
CHRYSENE
CORONENE C24 H'2
CREOSOTE mixture of phenols
m-CRESOL C7 Ha O (methylphenol)
CYCLOHEPTANE C7 H'4
CYCLOHEXANE Cs H'2
CYCLOHEXANOL Cs H'2 0
Appendix A
STRUCTURAL FORMULA
OH
ACI o CI I
CH,-CH-CH,
CI-CH' CH-CH,
OH
0 /. CH ,
0
0 OH
0
Appendix A
NAME MOLECULAR FORMULA
CYCLOHEXANONE C6 HIOO
2.4- 0 (2.4- dichlorophenoxyacetic Ce H6 CI 2 0 3
acid)
OBH (4.4'-dichlorobenzhydrol) CI3 H10CI 2
o B P C H OCI (4.4'-dichlorobenzophenone) 13 e 2
OOA (4.4'-dichlorodiphenyl acetic Cl4HI002 CI 2
acid)
OOCN (4.4'-dichlorodiphenylacetonitrile) C 14 H 9 N CI 2
OOCO (dichloro diphenyl carbonyl) CI3 He OCI2
DOD (4.4'-dichlorodiphenyldichloroethane) CI4H tOC 14
251
STRUCTURAL FORMULA
o o o
CIQ 0- CHz- COOH CI
C10CHOHOCI
CI-<D-~ b ~ CI \_ 1~/r-- C'O I OH
H
C10+OCI CN
HCCI Z CIOCIHOCI
252
NAME MOLECULAR FORMULA
DOE (4,4'-dichlorodiphenyldichloroethylene) CI4 H 8 CI 4
DDM
(4,4'-dichlorodiphenylmethone )
DO M S C H CI (4,4'-dichlorodiphenylchloroethone) 14 1\ 3
DO M U (4,4'-dichlorodiphenylchloroethylene) CI4 Hg CI3
DONS ( 4,4' -dichlorodiphenylethone )
DDNU (4,4~dichlorodiphenylethylene )
DDT (4.4'-dichlorodiphenyltrichloroethone) CI4 Hg CI 5
o ECACHLOROBIPHENYL
DECAHYDRONAPHTHALENE
DIBENZ (A,H) ACRIDINE
Appendix A
STRUCTURAL FORMULA
CI -Q-CH2-Q- CI
CI -Q-TI-D- CI C-CI I H
hi cH' CI <:;-----DCI
CI CI CI CI
en H
Appendix A 253
NAME MOLECULAR FORMULA STRUCTURAL FORMULA
rnBENZ(A,H)ANTHRACENE C22 HI4
DIBENZOFURAN CI2 He 0 ~ Br
p-DI BROMOBENZENE C6 H4 Br 2 0 Br
H
DIBROMOCHLOROMETHANE CHBr2CI I CI-C-Br
I Br
DIBROMOETHANE C2 H4 Br2 Sr -CH z -CH2-Br
DIBROMOMETHANE CH 2 Br2 Br - CHz- Sr
2,3 -DIBROMOTOLUENE CH 3 C6 H3 Br2 OBr
/- Br
OH
2,4-DIBUTYLPHENOL CI4 H22O I ' QC(CH,1
/.
C(CH,I,
CI
DICHLOBENIL C7 H3 CI 2 N QCN CI
CI
m-DICHLOROBENZENE C6 H4 CI 2 0 /. CI
254 Appendix A
NAME MOLECULAR FORMULA STRUCTURAL FORMULA
DICHLOROBE NZOF URAN Ca H 3 CI 2 O ! I C'(JQ
c, '" 0
4,4'- DICHLOROBIPHENYL CI2 H a CI 2 c'-Q---Oc,
H , DICHLOROBROMOMETHANE CHCI 2 Br Br-C-CI
I CI
c,
DICHLOROCATECHOL C6 H4 O2 CI 2 CIO
'" OH
OH
F
DICHLORODIFLUOROMETHANE CCI 2 F2 I
F - C - CI I c,
DICHLOROETHANE C2 H4 CI 2 CI-yH-CH 3
CI
CI
DICHLOROETHYLENE C2 H2 CI 2 I
CH.' ~ CI
H I
DICHLOROFLUOROMETHANE CHCI 2 F F-C -CI , C,
CI
DICHLOROGUAIACOL C7 H6 0 2 CI 2 CIO
'" 1 OCH.
OH
DICHLOROMETHANE CH 2 CI 2
~ CI-C-H
( methylene chloride) I CI
Appendix A 255
NAME MOLECULAR FORMULA STRUCTURAL FORMULA
DICHLOROMETHYL GUAIACOL CeH7 0 2CI 2 CIO
CI ::---- ' OCH,
OH
OH
01 C HLOROME THYLPH ENOL C7 HSOCI2 CH'OCI
::----' CI
CH,
DICHLOROMETHYLVERATROLE Cg H100 2 CI 2 CI¢C' ::---- OCH,
OCH 3
OH
2,3 - DICHLOROPHENOL Cs H4 OCI 2 (j( ::---- CI
1,2-DICHLOROPROPANE C 3 Hs CI2 ~H2-~H-CH3
CI CI
1,3-DICHLOROPROPENE C3 H4 CI 2 CI-CH"CH-CH.-CI
(d ichloropropylene 1
2,4-DICHLOROTHIOPHENOL CS H3 SHCI 2 (]ISH
CI ~, CI
CI
~CI DIELDRIN CI2 He Cis 0 o CCI.' CI
CI
OH
3,5 -[)IETHYLP!iENOL C'OH'4 O 0 Hs C2 C2 H S
OH
1,5-DIHYDRODIHYDROXY-BENZO C H 0 (Al PYRENE 20 14 2
OH
256 Appendix A
NAME MOLECULAR FORMULA STRUCTURAL FORMULA
ETHYLENE OXIDE C2 H4 ° CHz - CH z "'0/
OH
m-ETHYLPHENOL Ce HloO G ",I C2 H5
CH,O\S
FENITROTHION C9 HI2 N0 5 PS ~-OQNO / _ 2 CH,O CH,
0& FLUORANTHENE C1sH 1O /'1 '" 1 '" '"
FLUORENE CI3 HIO CC)J /- '"
CI I
F LUOROTRICHLOROMETHANE CCI3F CI - C -CI I F
0
FORMALDEHYDE H CHO II
H- c- H
COOH
GLUCURONIC ACID Cs HI00 7 ~ OH OH OH
GLUTATHIONE CIO HI7 N3OSS H2 NCHCH2CH 2CONHCHCONHCH2COOH I I COOH CH2SH
GLYCERINE (GLYCEROL) C3 He 03 HOCH. CHOH CH2 0H
Appendix A 257
NAME MOLECULAR FORMULA STRUCTURAL FORMULA
CI
CI~CH,OH
ENDOSUlFAN DIOl CgHeCI602 I CCI,
CI/~f'.,.CH OH I ' CI
CI
CI~CH'-O~ ENDOSUlFAN SULPHATE C9 H 6 CI6 0 4S I CCI, ..-/ so,
Alkylation Transfer of an alkyl group (Cn H21l+ 1) to a metal atom Anthropogenic Any material originating from human activity Arylation Transfer of an aryl group (C6Hs) to a metal atom Chelator A ligand with more than one binding site Chromophore A chemical group that gives rise to color in a molecule Colloids Particles of size range 0.1-0.45 f.lm Complex A simple ligand with one binding site Concentration Factor (CF) Quotient relating concentrations of pollutant in
two different phases. For example, biota/water Conditional Stability Constant Stability constant valid for a given set of
conditions, such as pH, and ionic strength. cf Stability Constant Contamination Natural and/or man-induced adulteration of abiotic and/or
biotic substrates Cracking Decomposition of petroleum with heat, steam, or other agents I:DDT All DDT analogs combined Dehalogenation Loss of one or more halide atoms from a compound Desorption Release of surface bound pollutants from solid matrices Disproportionation Nonstoichiometric breakdown of a compound Eh Redox potential Evaporation Transport of a compound from the liquid phase to the gas
phase Fractionation Separation of a compound( s) into different physical and
chemical components Fulvic Acid An acid-alkali-soluble humic material, originating from the
breakdown of lignin and tannins
Appendix B
Glycoside Acetals derived from hydroxy compounds and sugars Halogenation Combination of Cl, Br, I, or F with a compound
273
Humic Acid An acid-insoluble component of humic material, with molecular weight greater than fulvic acid
Hydrolysis Interaction of a compound with hydrogen, hydroxyl radicals, or water molecules
IUPAC International Union of Pure and Applied Chemistry Koc Partition coefficient normalized to organic carbon Lactone Internal cyclic monoester of a hydroxycarboxylic acid Ligand A molecule containing a donor atom capable of forming a bond with
a metal Mercaptan Compounds resembling alcohols but having the oxygen of the
hydroxyl group replaced by sulfur Nucleophile Atoms or groups with an excess of nonbonding electrons
having an affinity for positively charged sites Parachor Molecular volume Partition Coefficient Distribution of a compound in different phases or
matrices (tissue, water, sediments, etc.) Photolysis Chemical decomposition by the action of radiant energy Photooxidation Oxidation induced by radiant energy Refracture Index Measure of the biodegradability of a compound Sorption Reversible binding of a pollutant to a solid matrix Substituted Compound Replacement of one or more hydrogen atoms with
other atoms or groups Unsubstituted Compound No replacement of hydrogen atoms with other
atoms Uptake Nonreversible accumulation of a pollutant Volatilization Transport of a compound from the surface of a liquid to the
gas phase Vapor Pressure Solubility of a compound in air from the liquid phase Xenobiotic Foreign substance in a living system
Appendix C Common and Scientific Names
of Fish Cited in This Book
Alewife Alosa pseudoharengus American shad Alosa sapidissima Atlantic cod Gadus morhua Atlantic salmon Salmo salar
Bass Micropterus sp. Black bullhead lctalurus melas Blenny Blennius pavo Bluefin tuna Thunnus thynnus Bluegill Lepomis machrochirus Brook trout Salvelinus jontinalis Brown bullhead lctalurus nebulosus Brown trout Salmo trutta
Lake trout Salvelinus namaycush Lake whitefish Coregonus clupeaformis Largemouth bass Micropterus salmoides Largescale sucker Catostomus macrocheilus Little skate Raja erinacea
Mosquito fish Gambusia affinis Mummichog Fundulus heteroclitus
Walleye Stizostedion vitreum White perch Morone americana White sucker Castostomus commersoni Whiting Merlangius merlangus Winter flounder Pseudopleuronectes americanus
Yellow perch Perca flavescens
Appendix C
Appendix D Equations for the Evalution of
Physico-Chemical Fate Processes
D-I. Calculation of the aqueous solubility of an organic compound using Quayle's parachor value.
where S = aqueous solubility in molal concentration, Pr = Quayle's parachor, and Ew = hydrophilic group factor. The validity of this equation was tested with 156 compounds of known solubility, and the correlation coefficient was found to be 0.962 (Moriguchi, 1975).
D-2. Calculation of vapor pressure by the equation of Weast (1974)
10glO P = (-0.2185 A/K) + B
where P = vapor pressure in torr, A = molar heat of vaporization, K = temperature in degrees Kelvin, and B = constant. For a given compound, values of A and B are constant over a moderate range of temperature. Values of A and B for several pollutants have been listed by Weast ( 1974) and can be used to calculate vapor pressures directly. Where A and B are not available and two or more vapor pressure values are given for temperatures bracketing 25 QC, this equation can be used to calculate A and B from the known two sets of ordered pairs (KI , PI) and (K2' P2). Then the constants A and B are substituted in the equation to calculate P at T = 298°K (=25°C).
D-3. Calculation of vapor pressure by the Clausius-Clapeyron equation
278 Appendix D
where P = vapor pressure in torr, 6.Hv = molal heat of vaporization, T= temperature in degrees Kelvin, R = gas law constant (1.99 cal! moleOK), and subscripts 1 and 2 refer to two different temperatures. The solution of this equation requires the knowledge of boiling point and heat of vaporization. Calculations from this equation provide only a rough estimate of vapor pressure.
D-4. Calculation of volatilization rate constant
where
and
Rv Cw = k" L = kg =
Hc= kg =
R T =
d[cw ] R = --- = k [c ]
v dt v W
1 k=-
v L
volatilization rate of a chemical, C (moles L-I hr- I) aqueous concentration of C (moles L- 1 (=M» volatilization rate constant (hr-I) depth (cm) mass transfer coefficient in the liquid phase (cm hr- I) Henry's law constant (torr M-1)
transfer coefficient in the gas phase (cm hr -I) gas constant (Iiter-atm-mole- I degree-I) and absolute temperature (degrees Kelvin).
In both phases,
ke =DRjae and kg = Dgjag
where D = diffusion coefficient and a = boundary layer thickness.
D-S. Calcl,llation of the volatilization loss of an organic compound
(J<;)env = (k~)Rab (~)env
where J<, = volatilization rate constant for the chemical (hr- I)
and Ie:, = oxygen reaeration constant (hr- I) in the laboratory or environment.
Appendix D 279
F or example, the quotient k;,/ ~ for benzene was independent of turbulence, salt concentration, temperature (4-50aC), and presence of surface active compounds (Smith et al., 1980).
D-6. Equations for electron and proton changes
Equations for Electron and Proton Changes
Concentration of proton, H
pH = - log [H]
High pH = low H+ activity and conversely
pH = pI(" when [A-] = [HA]
Ka = acid dissociation constant, HA ;=0 H+ + A-
Concentration of electron, E
PE = log [e-]
High PE = low c activity and conversely
[oxidized] PE = PEQ + log
[reduced]
PE = PEa when [oxidized] = [reduced]
PEQ = equilibrium potential
D-7. Calculation of the rate of hydrolysis of a chemical compound
de - - = kA [H+] [e] + kB [OH] [C) + kN [C)
dt
where kh = first-order hydrolysis rate constant at a specific pH; kA and kB = second-order acid and base hydrolysis constants, respectively; and kN = first-order hydrolysis rate constant for pH independent reaction.
D-8. Rate of disappearance of an organic compound by direct photolysis
de dt = Kp [C) = ka O[C]
where kp = first-order rate constant, ¢ = reaction quantum yield, and ka = rate constant for light absorption by the chemical that depends on the light intensity, chromaticity of light, and extinction coefficient of the chemical.
D-9. Rate of disappearance of an organic compound by indirect photolysis
280
de = k2 [C] [X] = k; [C]
dt
Appendix D
where k2 = second-order constant for the interaction between the chemical and the intermediate, X; for a photosensitized reaction the k; would be a combined term including the concentration of the excited state species and the quantum yields for the energy transfer to and subsequent reaction of the chemical. In any estimate of kp or k;, values of ka or [X] should be specific, taking into account the variation of the intensity of sunlight with time of the day, season, and latitude.
D-10. Rate of substrate utilization
de
dt Y (Y)
(CX) (CX) (Ks + C) = (kb)' (Ks + C)
where f.l = specific growth rate, X = biomass per unit volume, J.lm = maximum specific growth rate,Ks = concentration of the substrate to support half-maximum specific growth rate (0.5 J.lm), kb = substrate utilization constant or biodegradation constant, (=J.lm/Y), and Y= biomass produced from a unit amount of substrate consumed. These constants f.lm, Ks , and Y are dependent on the characteristics of the microbes, pH, temperature, and media.
D-ll. Reduced equation for the rate of substrate utilization
When the substrate concentration C ~ Ks , the equation D-IO reduces to:
de --=kX
dt b
This means that the biodegradation rate is first order with respect to all . biomass concentration and zero order with respect to chemical concentration.
D-12. Reduced equation for the rate of substrate utilization
In actual environmental situations for many pollutants, C< <Ks , hence equation D-IO becomes:
de (CX) = (kb)' -- = kb2 [C] [X]
dt (Ks)
where kb2 is a second-order rate constant.
Appendix D 281
D-13. Reduced equation for the degradation rate of a chemical
When the biomass concentration is relatively large compared with the pollutant concentration, the degradation rate is pseudo-first order and given by:
de -- = k'C
dt b
where k'b is the pseudo-first-order rate constant and dependent on the cell concentration (Xo).
D-14. Calculation of the half-life of a chemical under degradation
The half-life of the chemical under degradation (t\1 at a given Xo) will be
In 2 0.693 t =---
1/2 k X b2 0
where
(k'b = pseudo-first-order rate constant and Xo = cell concentration.)
D-15. Kinetic half-lives of chemicals
Half-lives of organic compounds are calculated from the respective rate constants and their dependence on physical parameters such as temperature.
For a first-order kinetic reaction, A1. products at a constant volume.
The rate of disappearance of A is given by:
dCA -dt = kj CA
where CA = concentration of A in moles L- I
t = time in appropriate units ~ = reaction rate for the process j in units of inverse time, and
dCA -- = rate of change of CA with time.
dt
282 Appendix D
Integrating the equation between the limits of to (initial time) and t, yields:
where CAo = initial concentration of CA at to. For CA = 0.5 CAO ' the half-life is given by:
_ 1 (2CAQ )
t\/2 - kj In (CAO )
or
t\/2 = 0.693 (:j) If all the transformation processes are expressed as a first-order or pseudo
first-order kinetic process, the net half-life for the chemical is given by:
References
Moriguchi, I. 1975. Quantitative structure-activity studies. I. Parameters relating to hydrophobicity. Chemical and Pharmaceutical Bulletin (Tokyo) 23:247-257.
Smith, J.H., D.C. Bomberger, Jr., and O.L. Haynes. 1980. Prediction of the volatilization rates of high-volatility chemicals from natural water bodies. Environmental Science and Technology 14:1332-1337.
Weast, RC. (Ed.). 1974. CRC handbook of chemistry and physics. 54th edition. CRC Press, Cleveland, Ohio, pp. 0-162-0-188.
Index
Aliphatic hydrocarbons, 16-42 accumulation, 28-33 air,28-29 algae, 33-36 alkanes, 16ff American Public Health Association,
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