é ESE-,1 , z a J. . Jud ’2 , .. 5 arm“? i 1.?- . if.!n€ .. V . . . 9.11,)... A). u. .7... u {H5933 nsmr LIBRAR a k llllllllllllllllllllllllilllllllllllllllll 3 1293 01396 6423 This is to certify that the thesis entitled The Partitioning of Phenanthrene and Benzo(a)pyrene to Humic Acid: The Comparison of Sep-Pak and Empore Disk C-18 Reverse Phase Materials Used in the Determination of the Partitioning Coefficient and the Effect of pH and a Solvent Phase on Partitioning Results presented by William H. Brunner has been accepted towards fulfillment of the requirements for M.S. degree inEnijonmenIal Engineering (fl fldé Major professor Date._Sum=r 1095 0-7639 1 MS U is an Affirmative Action/Equal Opportunity Institution v... '_. LIBRARY Mlchlgan State Unlverelty PLACE IN RETURN BOX to remove We checkout from your record. To AVOID FINES return on or before dete due. DATE DUE DATE DUE DATE DUE 1:1 II F I‘v- ‘ ‘L CVle s: '0». e ‘ F . Pita: ; ‘ ..’A e. :‘I'P‘Teeevh..‘- THE PARTITIONING OF PHENANTHRENE AND BENZO[A]PYRENE TO HUMIC ACID: THE COMPARISON OF SEP-PAKO AND EMPORETM DISK C-18 REVERSE PHASE MATERIALS USED IN THE DETERMINATION OF THE PARTITIONING COEFFICIENT AND THE EFFECT OF PH AND A SOLVENT PHASE ON PARTITIONING RESULTS BY William H. Brunner A THESIS Submitted to Michigan State University in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE Department of Civil and Environmental Engineering 1996 A l .3. e h Yr R..- 2‘ . l -‘OOAQE '1‘; ‘ elb¢C.‘s PAH . into but. bail-as, “39d. K Ami,”ta influx? ‘c Ee‘ECt 0f “id 50“... ‘H ABSTRACT THE PARTITIONING OF PHENANTHRENE AND BENZO[A]PYRENE To HUMIC ACID: THE COMPARISON OF SEP—PAKO AND EMPOREW DISK C-18 REVERSE PHASE MATERIALS USED IN THE DETERMINATION OF THE PARTITIONING COEFFICIENT AND THE EFFECT OF PH AND A SOLVENT PHASE ON PARTITIONING RESULTS BY William H. Brunner Reverse phase analysis, conducted with both Sep-PakO Cartridge and Emporem Disk C—18 materials, was used to determine the partitioning coefficient of phenanthrene and benzo[a]pyrene in Aldrich and Suwannee River humic acid solutions, respectively. Experimental results from both materials yielded similar Kpresults. A PAH was dissolved in solvent and either spiked directly into humic acid solution or spiked into the experiment bottles, the solvent evaporated, and humic acid solution added. Kp values in evaporated solvent solutions were higher than in carrier solvent solutions. Also, opposite data trends in the Rg‘vs. humic acid content experiments were shown. The effect of pH was also studied. Decreasing pH in a PAH/humic acid solution increased Kp. To my parents for their loving encouragement. iii franc; The. ad rese ACKNOWLEDGMENTS Thanks to Dr. Tom Voice and Dr. Simon Davies for their financial and technical support. Thanks to Dr. John Giesey for his theoretical discussions and research ideas. Thanks to Joseph Nguyen for his help with analytical techniques. Finally, thanks to Dr. Brad Upham for his theoretical discussions and. help ‘with research techniques and data analysis. iv .A.‘III I 123': C? l 2.23? C? I 536.9. 1 RAHWI‘ VUUE‘ e 5.- Q c.‘ q 1 --¢ fa ..~. ‘ I ‘v (d In.) (.41 IA) .(51 in ab bl A) P-J fig El [5/ Be. TABLE OF CONTENTS LIST OF TABLES LIST OF FIGURES CHAPTER 1 INTRODUCTION . 1.1 Polycyclic .Aromatic HydrOCarbons 1.2 Humic Acid . . . 1.3 Partitioning of PAH to Humic ACid . 1.3.1 Solid Phase Sorption from an Aqueous Environment 1.3.2 Humic Acid and PAH Interaction 1.4 Determination of Partitioning Coefficient 1.4.1 Experimental Solution 1.4.2 Methods of Analysis 1.5 Research Objectives . CHAPTER 2 A STUDY OF THE PARTITIONING OF PHENANTHRENE AND BENZOIAJPYRENE To HUHIC ACID: COMPARISON OF THE SEP- PAH” C-18 CARTRIDGE AND THE EMPORETM C-18 EXTRACTION DISK REVERSE PHASE TECHNIQUES 2.1 Introduction . . . 2. 2 Materials and MethOds 2. 3 Results and Discussion 2.4 Conclusions CHAPTER 3 THE EFFECT 0? PH AND THE ADDITION OF A SOLVENT PHASE ON THE PARTITIONING OP BENZOtAJPYRENE AND PHENANTHRENE To HUMIC ACID . . 3.1 Introduction . Materials and MethOds 3.2 3.3 Results and Discussion 3.4 Experimental Implications 3.5 Summary . . CHAPTER 4 FURTHER RESEARCH vii viii #LMF‘H HGJQQU'IIF [-1 12 12 13 15 28 29 29 32 4O 4O 41 ‘qe-e-‘c—C “:e-n-‘av‘ I???" .‘U. n-U'Dfivq one-\ofl ‘ ‘ I- 3.- 5.; ‘ T I.- .o..1 3.: ‘ fl. ‘ n. ‘ “4| ‘ 5.4 ‘ l (1,, ‘ I 5-. u - fl.‘ ‘ n 5-- APPENDICES APPENDIX A MATERIALS AND METHODS . . . . . . . . . . . . . . . . . . 43 A.1 Materials . . . . . . . . . . . . . . . . . . . . . 43 A.2 Methods . . . . . . . . . . . . . . . . . . . . . . 44 A.2.1 Glassware Preparation . . . . . . . . . . . . 44 A.2.2 Reagent Water Preparation . . . . . . . . . . 44 A.2.3 Humic Acid Preparation . . . 45 A.2.4 Radiolabeled Humic Acid SolutiOn PreparatiOn 45 A.2.5 Emporem Disk Reverse Phase Method . . . . . 46 A. 2. 5. 1 Normal Procedure . . . . . . 46 A. 2. 5. 2 Filtering Speed Test PrOCedure . . . 49 A.2.6 Sep- Pak0 Reverse Phase Method . . . . . . . . 51 A. 2. 6. 1 Normal Procedure . . . . . . 51 A.2.6.2 Filtering Speed Test Procedure . . . 53 A.2.7 Total Organic Carbon Analysis . . . . . . . . 55 A.2.8 Liquid Scintillation Analysis . . . . . . . . 56 APPENDIX 8 RAW DATA . . . . . . . . . . . . . . . . . . . . . . . . 62 LIST OF REFERENCES . . . . . . . . . . . . . . . . . . 222 vi b g..- u b— ... 2. v . L - . — . \w .1. 11.1 111 C .2“ .1..“ a». :1.“ 111‘ T1112; .1 ‘-e “u 1 1 m1. “W .1...“ .1..._‘ Lu ~.~.~.~ 1.1 ...1 “11.1.1.1... .~.~.~ .s.‘ ....1. 1.1.. .111. "schemes. .s—Xs wake .«n‘e Queues ....11. ....1.1....c1 «Take CHAPTER 1 Table CHAPTER 2 Table Table Table Table CHAPTER 3 Table Table APPENDICIES APPENDIX A Table Table Table Table APPENDIX B Table Table Table Table Table Table Table Table Table Table Table Table Table Table Table Table Table Table LIST OF TABLES Humic acid composition Radiolabeled PAH data . . Breakthrough of PAH through C— 18 media Mass balance of PAH/reagent water solutions Mass balance Of PAH/humic acid sOlutions Radiolabeled PAH data . pH= 7 and PAH solvent carrier test results Radiolabeled PAH data . . Solutions used in experimentation . PAH concentration in humic acid solutions Quench of Sep- -Pak0 solvent solutions Data for Figure 2-1 Data for Figure 2-2 Data for Table 2-2 Data for Table 2-3 Data for Table 2- 4 Data for Figure Data for Figure Data for Figure Data for Figure Data for Figure Data for Figure Data for Figure Data for Table 3 Data for Figure 3 Data for Figure A- 1 Data for Figure A-2 Data for Table A-4 Data for Figure A-5 I UNNNNNN IN! -3 -4 -5 -6 -7 -1 2 3 vii 14 18 20 20 31 36 43 44 46 62 67 75 76 79 83 .108 127 138 148 167 186 196 208 212 216 217 CHAPTER 1 Figure Figure Figure CHAPTER 2 Figure Figure Figure Figure Figure Figure Figure CHAPTER 3 Figure Figure Figure Figure LIST OF FIGURES Polycyclic aromatic hydrocarbon properties . . . . . . . . . 2 Behavior difference between dissolved and sorbed species . . . . . . 6 Experimental materials and setup . . . . 10 The effect of filtering speed on percent bound and K; for benzo[a]pyrene in Suwannee River humic acid . . . 16 TOC recovered from humic acid solutions after reverse phase analysis . 17 The effect of filtering speed on the % bound and KP of phenanthrene in Aldrich humic acid . . . 22 The effect of increasing humic acid content on the % bound and.Bg of benzo[a]pyrene in Suwannee River humic acid . . . . 24 The effect of increasing humic acid content on the % bound and Kp of phenanthrene in Aldrich humic acid . . . 25 The effect of time on the % bound and Kp of benzo[a]pyrene in Suwannee River humic acid . . . . . . . 26 The effect of time on the % bound and KP of phenanthrene in Aldrich humic acid . . . . . . . . . . . 27 Partitioning results: benzo[a]pyrene in Suwannee River humic acid . . . . . . . 33 Partitioning results: phenanthrene in Aldrich humic acid . . . . . . 35 Partitioning results: phenanthrene in Aldrich humic acid. Different Amounts of phenanthrene in 10 uL acetone carrier solvent . . . . . . . . . . 37 PAH/Humic Acid/Water/Solvent system . . 39 viii APPLY; APPZND APPENDICES APPENDIX A Figure A-1 The quenching effect of Aldrich humic acid content in liquid scintillation . . . . 58 Figure A-z Log TSIE values compared to solution quench . . . . . . . . . . . 59 ix CHAPTER 1 INTRODUCTION 1.1 Polycyclic Aromatic Hydrocarbons Benzo[a]pyrene and phenanthrene are polycyclic aromatic hydrocarbons (PAHs) . Physical properties are detailed in Figure 1-1. They are solids that exhibit low solubilities in water(1). Their octanol/water partitioning coefficients (Log K“) are high, meaning that in an octanol/water environment, they will exist primarily in octanol(2). Benzo[a]pyrene is produced by both manmade and natural sources. Manmade sources include coal, coke, and coal tar processing; petroleum refining; road bed and asphalt leachate; and the combustion of fossil fuels and tobacco(2) . In the environment, small quantities are produced by various bacteria and algae(2). Phenanthrene is used in the production of dye, explosives, drugs, and in biochemical research(2). It is found in gasoline, oil, and coal tar and is produced during the combustion of fossil fuels(2). Phenanthrene and benzo[a]pyrene have been shown to bioaccumulate in aquatic systems(3-7) . Benzo[a]pyrene is a confirmed carcinogen(8). Human mutagenic and reproductive 1 x\\ I a .28 V V . m b A Polycyclic Aromatic Hydrocarbon Properties r t r Molecular Wt. Sol ili Log KnW Phenanthrene ©© 178.24 0.816 ppm 4.46 BenzoIalDYrene ©© 252.32 0.003 ppm 6.50 Figure 1-1 Polycyclic aromatic hydrocarbon properties. “ O EbbeC5 r- vo‘fi obgee 3 effects have also been reported. Phenanthrene is a suspected carcinogen with neoplastigenic and tumorigenic data reported(8). It is moderately toxic by ingestion. 1.2 Humic Acid HUmic substances are soluble organic macromolecules that are prevalent in natural aquatic systems. They are composed of a mixture of organic materials including the remains of woody plants, terrestrial organisms, and planktonic remains( 1) . Humic substances are composed of both fulvic and humic acids(1). Fulvic acids are soluble in both acidic and basic solutions. Humic acid dissolves at a high pH. Humic acid contains 40-50% carbon by weight, almost as many oxygens, and a few nitrogens(1,9,10) . Suwannee River and Aldrich humic acids were used in this research. The composition details are listed in Table 1-1. Table 1-1 Humic acid composition. HA C H O N S P — Aldrich 58.39 4.24 33.13 .63 3.57 0.13 [Suwannee 54.55 4.16 39.24 1.22 0.82 0.01 I Note: All measurements in percent on a moisture-free basis, normalized to a 100% total. Information ,adapted from Chiou(9,10). In 4 1.3 Partitioning of PAH to Humic Acid 1.3.1 Solid Phase Sorption from an Aqueous Environment Sorption of PAHs to humic acid in water is governed by free energy in the system(1,11). The chemical is driven to the solid surface because the free energy is lower at the solid surface than in the bulk water solution. Equilibrium distribution of the chemical between the solid and water phases is attained when the free energy in the system reaches a minimum. A water system is a polar environment created by the electron affinities of the hydrogen and oxygen atoms(1) . Hydrogen carries a slight positiVe charge and oxygen a slight negative charge. Water molecules orient themselves so that their positive and negative ends are near each other, thus lowering the system free energy. This is called hydrogen bonding between water molecules and dipole—dipole interaction between non-similar, polar molecules. Nonpolar chemicals attract by inducing minute intramolecular polarity variations in each other(1,11). Nonpolar chemicals are much less stabilized in polar solutions than in nonpolar environments and will be driven to escape to these nonpolar environments. The relationship between the concentration of sorbate in solid (C,) and water (C.) phases is cs=x-c; m sxf cc 9"“§l q U--b-v be en: There I; 5 This is the Freundlich isotherm where K is the Freundlich constant and n is a measure of how difficult it is for multiple layers of molecules to bond to the solid surface( 1,11) . For constant concentrations of sorbate in solution, the equation can assumed to be linear (n=1) and can be expressed as Cs fig‘=-E: (2) where K5 is the distribution or partitioning coefficient(1). K5 is a measure of how much sorbate partitions between solid and water phases. This equation was used to determine the partitioning coefficient of phenanthrene in Aldrich humic acid solution and benzo[a]pyrene in Suwannee River humic acid solution. 1.3.2 Humic Acid and PAH Interaction Humic acid contains similar amounts of carbon and oxygen, elements that have a similar affinity for electrons(1) . Therefore, a relatively nonpolar environment is presented into which PAHs can escape from water, thus increasing their solubility. PAH mobility in the environment is increased due to ingestion by organisms, settling with humic acid to the sediment, and infiltration into groundwater systems(1). However, humic bound PAHs have been shown to be less bioavailable, less likely to volatize, and shielded from interaction with free radicals(1,3-7) (Figure 1-2). (a) (b) Water < /\>/\v > V<>AVV >V V v> > /\> > < v v v < > > > >>< /\ AA>< V v< v /\< V > > >< /\< VA dissolved organic molecules settlin with particles for colliding with air-water interface sorbe organic molecules and volatilizing Air- / Water < A> 7‘ > V>< >Avv V . > A“ <‘ A \/ /\ V V -v><< A A/V>v> R00 /\ > 1 > /\ >VV< < dissolved organic molecule more accessible to lig‘hat. other dissolved chemicals. and microorganisms t n sorbed molecules Figure 1-2 Behavior difference between dissolved and sorbed species(1). (a) Volatization and settling. (b) Rate of reaction. dry 1:: the de syste: n‘“ ‘ s‘cglc mi :33. p5 of PA}: 7 1.4 Determination of Partitioning Coefficient 1.4.1 Experimental Solution The experimental solution is prepared by first dissolving dry humic acid into reagent water, then adjusting the pH to the desired value. Next, the PAH must be introduced into the system. The system must then be mixed for a time period sufficient enough for the PAH distribution between the solid and the water phases to reach equilibrium(12). pH has been shown to have an effect on the partitioning of PAH to humic acid. Increasing the pH in a water system increases the number of charged sites in the humic acid polymer(13) . This is due to the presence of phenolic and carboxylic functional groups in the molecule(14). Although the polymer expands, fewer sites are available for bonding; the polymer becomes more hydrophilic due to the increased number of charged sites. Reducing pH in a water system neutralizes the charges, the humic polymer coils and becomes more hydrophobic(15) . Landrum found that decreasing the pH of benzo[a]pyrene in stream and well water increased the amount of benzo[a]pyrene trapped in a XAD-4 resin(16). Schlautman and Carter found that the K1, of hydrophobic organic chemicals decrease with increasing pH(15,17). Introduction of PAH into humic acid solution can be done in a number of ways. Solvent is commonly used to dissolve PAH. A small amount of PAH/solvent solution can then be injected into humic acid solution. Also, the PAH/solvent solution can be injected into a glass bottle, then the solvent evaporated ‘ ‘Av to hr.- and F: 8 Jbefore humic acid solution is added. Finally, the PAH/solvent solution can be dispersed amongst a number of glass beads. .After the solvent is evaporated, the humic acid solution is introduced and cycled through the glass beads until a equilibrium distribution of PAH in solution is attained. Solvents have been used by many researchers to introduce PAH to humic acid solution(7,12,18-22). Schlautman(23), Munz(24), and Morris(25) found that the addition of a small amount of methanol has no effect on the partitioning of perylene to Suwannee River humic acid. 1.4.2 Methods of Analysis Florescence quenching(18,26), dialysis(5,27), and reverse phase analysis(27,28) have been used to determine PAH partitioning coefficients in humic acid solutions. In florescence quenching, the decrease in florescence intensity is directly proportional to the increase of florescent chemical binding to dissolved organic material(26). Dialysis bags allow PAH to move freely through the dialysis membrane; humic acid cannot. water phase PAH is assumed to exist in the same concentration both inside and outside the bag. The humic bound PAH is the amount equal to the difference between PAH concentrations inside and outside the tube. Reverse phase analysis with XAD-4 resins has been used to separate humic bound and dissolved PAHs(29). Reverse phase analysis with C-18 cartridges can be used to rapidly determine the partitioning of PAHs to humic acid(27,28). The cartridge 9 material is composed of C18H37, which is bonded to a silica matrix. It presents a nonpolar environment into which the water phase PAH escapes while PAH/humic acid solution is passed through the system. Humic acid passes quantitatively through C-18 reverse phase materials at a pH greater than 5(27). PAHs bound to the C-18 matrix can be eluted with a solvent solution. The Waters Sep-PakO C-18 Classic Cartridge, shown in Figure 1-3, is used in this research. The reverse phase material is contained in the 13 mm long, 11 mm diameter center section. It contains 360 mg Packing Material and has a 125 A Pore Size. Fluid is passed though the cartridge with a syringe. Use of a C-18 disk in reverse phase analysis holds interesting possibilities. Compared with the cartridge, the disk is thin and composed of a smaller amount of hydrophobic material with a smaller average pore size. The solution has less of a distance to travel through the medium, and therefore, the mass balance of the reverse phase process may be improved. A disadvantage of the C-18 cartridge is that the partitioning coefficient depends on the flow rate. Since the disk is much thinner than the cartridge, flow rate variations may be less likely to affect the partitioning coefficient. The J. T. Baker Empore‘" 25 mm C-18 Extraction Disk was used in this research. It is 25 mm in diameter, 500 um Thick, and has a 60 A pore size. Fluid is passed through the disk with an exterior vacuum source and the frit/funnel/clamp assembly 10 (a) (13) film Dia. 13 mm 1’ Din. r— 19 L_Dia. (C) Figure 1-3 Experimental materials and setup. (a) Empore'" Disk Conditioning Assembly. (b) Empore Disk Vacuum Chamber. (c) Sep-Pak Cartridge. sh“ 11 shown in Figure 1-3. 1.5 Research Objectives The objective in this research was to investigate the use of the J. T. Baker Empore'" 25 mm C-18 Extraction Disk in the measurement of the partitioning coefficient of benzo[a]pyrene in Suwannee River humic acid and of phenanthrene in Aldrich humic acid. The research covered the following areas: Comparison of EmporeTM Disk and Sep-PakO Cartridges in the measurement of KP. Investigation of the effect of pH on the R1) of phenanthrene in Aldrich humic acid solution and benzo[a]pyrene in Suwannee River humic acid. Comparison of PAH introduction methods on the R9 of phenanthrene in Aldrich humic acid solution and benzo[a]pyrene in Suwannee River humic acid solution. Evaporated carrier solvent and solvent carrier methods were used. It! KL Fk-Ztol 1 ‘."'S ch Chapter-2 A STUDY or TEE PARTITIONING OP PEENANTERENE AND BENZO[A]PYRENE To EUHIC ACID: CONRRRIBON 0? THE BER-PAKG C-IB CARTRIDGE AND THE ENPOREn‘ C-IB EXTRACTION DISK REVERSE PHASE TECHNIQUES 2.1 Introduction Benzo[a]pyrene and phenanthrene are polycyclic aromatic hydrocarbons (PAHs) that are abundant in the environment. Hanmade sources include oil, gasoline, coal tar, and the incomplete. combustion. of fossil fuels(2). They' are hydrophobic, exhibit low solubilities in water(1), and have been to bioaccumulate in aquatic systems(3-7). They are also carcinogens and mutagens that have been shown to produce reproductive effects in animal life(8). Dissolved humic acid increases PAH solubility in a water system. Humic bound PAHs are also less susceptable to bioaccumulation(3-7), reaction. with. other chemicals, and photolysis(1). Floresence quenching(18,26) and dialysis(5,27) have been used to determine PAH partitioning coefficients in humic acid solutions. Also, XAD-4 resins have been used to separate humic bound and dissolved PAHs(29). It has been shown that C-18 cartridges can be used to rapidly determine the partitioning of PAHs to humic acid(27,28). Humic acid passes quanitatively 12 13 through C-18 reverse phase materials at a pH greater than 5(27). Freely dissolved PAH sorbs to the C-18 material and the humic bound PAH passes through the medium. Use of a C-18 disk in reverse phase analysis holds interesting possibilities. Compared with the cartridge, the disk is composed of a smaller amount of hydrophobic material with a smaller average pore size. Therefore, the mass balance of the reverse phase process may be improved. Also, since the disk is much thinner than the cartridge, flow rate variations may be less likely to affect the partitioning coefficient. In this set of experiments, the performance of the Empore'” C-18 Extraction Disk is Compared to that of the Sep- PakO C-18 Classic Cartridge in the investigation of the partitioning of benzo[a]pyrene to Suwannee River humic acid and of phenanthrene to Aldrich humic acid. 2.2 Materials and Methods Suwannee River Humic Acid Reference was obtained from the International Humic Substances Society, Colorado School of Mines, lot number 1R101H. Aldrich Humic Acid was obtained from Aldrich Chemical Company, lot number 01816HH. The humic acid solutions were created by dissolving the humic acid in reagent water at a pH of 10, reducing the pH to 7, then by passing the solution through a 0.45 pm glass filter. Two lots of radiolabeled phenanthrene and one lot of benzo[a]pyrene were obtained from Sigma Chemical. The details are given in Table 2-1. Benzo[a]pyrene was dissolved in a 1:1 ‘E‘ t3-u€: 5 838.31"; l4 toluene:acetone solution and phenanthrene was dissolved in acetone. These solvent/PAH solutions were spiked into 250 ml glass bottles which were then placed in a hood in order to evaporate the solvent. After three days, humic acid solutions were added to the bottles and the bottles were placed in an orbital shaker for at least 16 hours before reverse phase tests were performed. The concentrations of phenanthrene and benzo[a]pyrene in solution ranged from 0.61-10.9 ug/L and 32- 91 ug/L, respectively. Table 2-1 Radiolabeled PAH data. I Phen 1 Phen2_ll B[A]P J Product No. 31,528-1 31,528-1 B9776 Lot No. O49F927l O49F9271-l O8OH9216 Activity, 13.1 8.3 16.2 mCi/mmol ; Purity >983: >98% >98% Waters Sep-PakO C-18 Classic Cartridges and J. T. Baker Emporem 25 mm C-18 Extraction Disks were used in reverse phase analysis. The Empore'" Disk was conditioned with 5 mL of 1:1 ethyl acetate:methyl chloride solution, followed by a 5 mL methanol rinse. 105 mL reagent water was then passed through the disk. Next, 5 mL of the PAH/humic acid solution was filtered though the disk on top of the water meniscus. The disk was eluted sequentially with 5 mL aliquots of ethyl acetate, methylene chloride, and 1: 1 ethyl:methylene chloride. All filtering speeds were 24 mL/min. Both the bound and free '11 I" I: ‘57. 8-. b was C 15 PAH phase were counted in all experiments except in the filtering speed test. In this experiment, only the bound phase was counted. The Sep-PakO Cartridge was conditioned with 10 mL of methanol, followed by 100 mL of reagent water. 5 mL of the PAH/humic acid solution was then filtered through the cartridge. The cartridge was eluted sequentially with 5 um. aliquots of ethyl acetate, methylene chloride, and 1:1 ethyl:methylene chloride. All filtering speeds were 30 mL/min. Both the bound and free PAH phase were counted in all experiments except in the filtering speed test. In this experiment, only the bound phase was counted. 2.3 Results and Discussion PAH binding to humic acid is easily reversible(12). When a PAH/humic acid solution is passed through a hydrophobic medium, free PAH will be adsorbed. Given enough contact time with the media, PAH will desorb from humic acid to reestablish equilibrium. Landrum has shown that an 8 cm column packed with VYdac 2018C will allow benzo[a]pyrene to desorb from the humic acid at low flow rates (0-3 ml/min)(27). Therefore, filtering speeds were chosen to minimize the contact time between the PAH/humic solution and the C-18 media. Figure 2-1 illustrates that percent bound and K, for benzo[a]pyrene increase with increasing flow rate to an asymptotic value. Filtering speeds were chosen at the asymptotic point. In this way, the percent bound was maximized and the possibility of breakthrough was 16 avoided. The filtering speeds used were 30 ml/min and 24 ml/min for the Sep-Pakdb Cartridge and the Emporem Disk, respectively . BENZOtAlPYRENE IN SUWANNEE HA % BOUND VS FILTERING SPEED 55 50‘ x x g.“ + , x ., z“ x n I) § 1. x n 35 , B 30 ‘ B 25 4 c r : Afi ¢ ; 5 10 15 20 25 30 35 40 FILTERING SPEED. MUMIN [ o uni-km x mm BENZO[A]PYRENE IN SUWANNEE HA Kp VS FILTERING SPEED 14000 12000 .. x " £10000 xx x - ‘ a! :3 a? 0000 x 5'! I! 0000 B ‘ a m 3 t 4 : fi- t ; 5 1O 15 20 25 30 . 35 40 FILTERING SPEED. MUMIN l n up-pkprocodm x mm] Figure 2-1 The effect of filtering speed on percent bound and K, for benzo[a]pyrene in Suwannee River humic acid. 17 Any humic acid retained in the C-18 media will reduce the tested percent bound and the RP of the PAH/humic acid solution. Figure 2-2 shows the TOC tested in both Suwannee River and Aldrich humic acid solutions before and after passing them through the Emporem Disk and Sep-Pako Cartridge. TOC TEST: TOC RECOVERED AFTER REVERSE PHASE ANALYSIS 2 70 v & 4 V x z' 60 x A O A g % o 50 2 g 40 a: r g 3 30 2 Z ° A (E Aldrich Humic Acid Suwannee River Humic Acid sample sep-pak empore sample sep-pak empore CONDITIONS Figure 2-2 TOC recovered from humic acid solutions after reverse phase analysis. "Samples" were tested before reverse phase analysis. The standard deviations show that 100% of the humic acid is recovered. The averages indicate that the Sep-PakO retains a slight amount of Aldrich and Suwannee River humic acids (2.88% and 9.93%, respectively). These values are similar with those obtained by Landrum (9813% has, avgistd) with Aldrich humic acid solutions and the Sep-PakO Cartridge(27). Also, Gardner found that humic materials bind poorly to reverse phase sateri in thi I“ tested benzo: 9 I 1 18 materials at pH>5(30). No adjustment for loss of TOC was used in this series of experiments. Breakthrough of the PAHs through the C-18 media was tested by first preparing solutions of phenanthrene and benzo[a]pyrene in reagent water. Then the solutions were filtered through both the Sep-PakO Cartridge and Empore'" Disk. The breakthrough percentages are shown in Table 2-2. Table 2-2 Breakthrough of PAH through C-18 media. PAH Reverse Average Phase Breakthrough, % Technique (avg t std) Benzo[a]pyrene Emporem 2.59 :t 0.19 n=3 Benzo[a]pyrene Sep-PakO 10.71 i 0.14 n=3 Phenanthrene Emporem 5 . 95 :l: 0 . 46 n=3 Phenanthrene Sep-PakO 15.97 i 0.57 n=3 At these flow rates the Empore'" Disk is more efficient at removing free PAH from solution than the Sep-PakO Cartridge. Landrum found no breakthrough for 0.5, 2, and 5 ug/L solutions of benzo[a]pyrene at a flow rate of 12 ml/min through the Sep- PakO Cartridge(27). Maaret (Maaret 1992) used C-18 Cartridges to determine partitioning of 1 ug/L Benzo[a]pyrene to humic acid at flow rates of and 5-12 ml/min(28). No breakthrough was reported. The breakthroughs eXhibited in this experimentation could be the result of the higher flow rate or of the larger amount of benzo[a]pyrene in solution (32-91 ug/L). ‘ wk there X 19 The amount of free PAH that breaks through the C-18 material from a PAH/humic acid solution comes from the PAH that is free in solution. Therefore, in order to obtain the amount of PAH bound to humic acid, the breakthrough numbers obtained from the PAH/ reagent water solution cannot be subtracted directly from the apparent bound PAH (total amount of PAH that passes through the C-18 material). Instead, breakthrough is a percentage of the PAH that is free in the water solution. The total bound amount for reverse phase analysis was adjusted as follows: (100m? X73 = 100% - (1) (loo-x3?) where X13 = percent PAH bound to humic acid; x, = percent PAH free in solution, measured by the reverse phase technique; and x5, a percent PAH that broke through the C-18 material from the PAH/reagent water solution. KP, the coefficient that measures the equilibrium distribution of PAH in a humic acid/water solution,is denoted C K, = 'E: (2) where C, = the PAH associated with humic acid (mol/kg) and C" = the PAH in solution (mol/L) . Kp was calculated as follows: it re C., = Hass I the C-18 ma dividing t} aliquot ta 78113125 2 .. 3 39329? . 20 K = XTB -6 L'g _ (3’ (cm) (10 H—mDmg) (100 X”) where ka= concentration of humic acid solution (mg/L). Mass balance was obtained by adding the PAH eluted from the C-18 material to the PAH that passed through the media and dividing this number by the amount of PAH obtained from an aliquot taken directly from the PAH/humic acid solution. Tables 2-3 and 2-4 contain mass balance results. Table 2-3 Mass balance of PAH/reagent water solutions. PAH Reverse Average Phase Mass Balance, % Technique (avg i std) Benzo[a]pyrene Empore“‘ 85.46 i 2.52 n=3 Benzo[a]pyrene Sep-PakO 86.34 t 0.24 n=3 Phenanthrene mflrem 87 .93 t 0.79 n=3 Phenanthrene Sep-PakO 93.55 t_0.47 n=3 Table 2-4 Mass balance of PAH/humic acid solutions. Reverse Average Phase Mass Balance, % Techni e av i std Benzo[a]pyrene Emporen‘ 86.53 i 5.36 n=22 Benzo[a]pyrene Sep-PakO 88.66 t 1.97 n=12 Phenanthrene Emporem 90.48 i 1.67 n=21 Phenanthrene Sep-PakO 90.33 t 3.28 n=11 exception. Paint! tech: : 0.47%) t balances ( were Sin: SSIUtion Landrum 56mm: ¢ “31319239 iP-proved t 531' Phena; Fig.1: be t nzoia3p {1‘ - scngerlng {‘43 they ] a?- n 8‘ 21 The mass balance averages of the EmporeTM Disk and Sep-Pak® Cartridge techniques are statistically similar, with one exception. In the phenanthrene/reagent water solution the Sep- PakO technique exhibits a significantly higher recovery (93.55 i 0.47%) than the Emporem technique (87.93 i 0.79%). The mass balances obtained in both reagent water and humic acid water were similar to that obtained by Landrum in humic acid solution (92 i 8%)(27). In water containing no humic acid, Landrum obtained recovery of only 67 i 12% by eluting the Sep-Pakc Cartridge with methanol(27). With ethyl acetate and methylene chloride used as elutants, the mass balance is improved to 86.34 t 0.24% for benzo[a]pyrene and 90.48 i 1.67% for phenanthrene. Figure 2-1 shows that both the percent bound and R5 of benzo[a]pyrene in Suwannee River humic acid increase as the filtering speed is increased. There is a slope to both curves and they level off to a asymptotic level. This indicates that at slow filtering speeds, the PAH desorbs from the humic acid in order to replace some of the free PAH that sorbs to the C- 18 material. Less of a slope was observed, however, than was reported for an 8 cm column(27). The percent bound and Kp of phenanthrene in Aldrich humic acid curves are approximately level for the EmporeTM Disk technique as filtering speed is increased (Figure 2-3). The curves exhibit a slight positive slope for the Sep-PakO technique. For the analysis of phenanthrene in Aldrich humic heh. I“ 22 acid, therefore, the choice of flow rate is not as critical as for the more hydrophobic benzo[a]pyrene in Suwannee River humic acid . PHENANTHRENE IN ALDRICH HA % BOUND VS FILTERING SPEED J o D a c: D a 45 a D I c: o ’40 O z 1 D 8 as a: “ w x 5 I! 25 : t ; 4' e : 5 10 15 20 25 30 35 FILTERING SPEED. MUMIN [ 0 «upon proud” x cop-pal: um PHENANTHRENE IN ALDRICH HA Kp VS FILTERING SPEED 50000 1: a 1 D D a I: 45W u a ‘ o a 40000 3...... £- . 30000 x m X g It 1 2m x4 : 4 c c c 5 10 15 20 25 30 35 FILTERING SPEED. MUMIN Figure 2-3 The effect of filtering speed on the % bound and KP of phenanthrene in Aldrich humic acid. There is a significant difference in the filtering test values between the Empore'" Disk and Sep-PakO Cartridge methods. The tests were performed after 5 days for the phenanthrene solution and 19 days for the benzo[a]pyrene 23 solution. According to Johnsen, the strength of the PAH/humic acid bond increases with time (0 to 70 days)(31). The larger amount of C-18 packing material in the Sep-Pako Cartridge compared with the Emporem Disk means that a larger amount of surface area is available for the PAH/humic acid solution to contact. This could enable some of the more tightly bonded PAH to be drawn out of solution by the Sep-PakO along with the free PAH, leading to reduced percent bound and KP figures. Alternately, the difference in values could be the result of a mass balance artifact, since only the bound phase was counted in the filtering speed experiments. Figure 2-4 shows how percent bound and K1, of benzo[a]pyrene vary with increasing Suwannee River humic acid content. Percent PAH bound to humic acid increases and Kp decreases with increasing humic acid content. Sep-PakO Cartridge and Empore'” Disk results are similar. These results compare to those obtained by Landrum(27) and McCarthy(12) in which R, of benzo[a]pyrene in Aldrich humic acid decreased with increasing humic acid content. Percent bound and RF of phenanthrene in Aldrich humic acid vary with increasing humic acid content (Figure 2-5) . Visual inspection shows that the Sep-PakO and Empore'" results are similar. Both the percent bound and KP increase with increasing humic acid content. No results are available from other authors for phenanthrene and increasing humic acid content . However , McCarthy found that the K1, of the PAH 24 naphthalene in Aldrich humic acid increased with increasing humic acid content(12). Figure 2-6 shows how percent bound and K5 change with increasing time for benzo[a]pyrene in Suwannee River humic acid. Both exhibit a slight decrease over a six day period. ewe 96 BOUND TO SUWANNEE RIVER HUMIC ACID 00 55 50 g 45 §4> 8 3 30 X 25 20 0 20 40 60 00 100 TOTAL ORGANIC CARBON. PPM :1 «upon procedure x cop-pal: Mu B[A]P Kp IN SUWANNEE RIVER HUMIC ACID 9M0 X 00000 70000 gun» ‘3 x .50000 #40000 30000 2M0 10000 0 40 00 80 100 TOTAL ORGANIC CARBON. PPM I 1: «upon pncoduc x cop-pal: M0] Figure 2-4 The effect of increasing humic acid content on the % bound and KP of benzo[a]pyrene in Suwannee River humic acid. 25 PHENANTHRENE °/o BOUND TO ALDRICH HUMIC ACID X saouno 3888838 .5 (I a O 12 14 10 18 20 22 1TTIAL<.eqppnklw0ouhle PHENANTHRENE Kp h ALDRICH HUMIC ACID I x x D D DX - 4 A A - . r Y r 10 12 14 1B 18 20 22 'HDTALCMNEANK3CVUUKJN.FTNI a CflflIlIPNIIUUNI x Ilpilkpfllndlhl Figure 2-5 The effect of increasing humic acid content on the % bound and RF of phenanthrene in Aldrich humic acid. 26 % B[A]P BOUND TO SUWANNEE HUMIC ACID KINETIC TEST RESULTS 38 1 V x: 37 A * 38 g- 35 4 A a: L i a I! 32 c *f : a: 4. ; ¢ 0 1 2 3 4 5 6 7 DAY F n00 A 400 x m Kp: B[A]P BOUND TO SUWANNEE HUMIC ACID KINETIC TEST RESULTS 42000 40000 I g ‘ a A V 53000 ‘ “ " 34000 W : 1+ : e ; : I a 0 ‘I 2 3 4 5 B 7 DAY I v +8“ 5 4M x m1 Figure 2-6 The effect of time on the % bound and KP of benzo[a]pyrene in Suwannee River humic acid. Figure 2-7 shows how percent bound and Kp for phenanthrene in Aldrich humic acid change with increasing time. Both exhibit an increase over a time span of ten days. The Empore‘" Disk was 1.25 benzcfi \ N \ .M‘ .‘Mre k IKE" 2 “anthr 27 was used in the kinetic analysis for both phenanthrene and benzo[a]pyrene solutions. % PHENANTHRENE BOUND TO ALDRICH HA KINETIC TEST RESULTS BOUND.“ 6 b t as}: “DXG 4 S 8 10 DAY . lvntdaaulxavg] szPHENANTHRENE BOUND TO ALDRICH HA 0 N KINETIC TEST RESULTS nan amp an» «up gm numb a‘24::a000 «up an» an» 0 2 4 0 a 10 ww' [Tmauxm] Figure 2-7 The effect of time on the % bound and K9 of phenanthrene in Aldrich humic acid. 28 2.4 Conclusions The Sep-PakO C-18 Cartridge and the Emporem C-18 Extraction Disk give similar results when used to determine the distribution constants of phenanthrene and benzo[a]pyrene in humic acid. The mass balances, % bound, and KP results were similar for both methods. Even though the results were significantly different for the Emporem Extraction Disk and Sep-PakO Cartridge techniques in the filtering speed tests, the data trends were similar. The smaller breakthrough numbers obtained for the Empore‘“ Disk, however, may mean that the Empore'" Disk technique is more accurate than the Sep-PakO Cartridge when determining the K, of solutions in which the percent bound number is small. This occurs at low humic acid concentrations. Also, the Sep-PakO retains small amounts of humic acid. This could lead to lower Kp estimations due to the retention of PAH-humic complexes in the C-18 matrix. The RF of benzo[a]pyrene in Suwannee River humic acid decreases with increasing humic acid content and decreases with time. The RP of phenanthrene in Aldrich humic acid increases with increasing humic acid content and also increases with time. Chapter 3 was spruce or pn nun ran ADDITION or a convene pans: ON THE PARTITIONING OP EENZO[R]PYRENE AND PHENANTHRENE TO MIC ACID 3.1 Introduction Benzo[a]pyrene and phenanthrene are polycyclic aromatic hydrocarbons (PAHs) that are abundant in the environment. Manmade sources include oil, gasoline, coal tar, and the incomplete, combustion of fossil fuels(2). They are hydrophobic, exhibit low solubilities in water(1), and have been to bioaccumulate in aquatic systems(3-7). They are also carcinogens and mutagens that have been shown to produce reproductive effects in animal life(8). Dissolved humic acid increases PAH solubility in a water system. Humic bound PAHs are also less susceptible to bioaccumulation(3-7), reaction 'with other chemicals, and photolysis(1). pH has been shown to have an effect on the partitioning of PAH to humic acid. Increasing the pH in a water system increases the number of charged sites in the humic acid polymer(13). This is due to the presence of many phenolic and carboxylic functional groups in the humic acid solution(14). Landrum found that decreasing the pH of benzo[a]pyrene in stream and well water increased the amount of benzo[a]pyrene 29 trap-pa 30 trapped in a XAD-4 resin(16). Schlautman and Carter found that the K5 of hydrophobic organic chemicals decrease with increasing pH(15,17). Solvents have been used by many researchers to introduce PAH to humic acid solution. Schlautman found that the addition of small amounts of methanol has no effect on the partitioning of perylene to Suwannee River humic acid(23). This series of experiments investigates the effect of pH and the use of a solvent carrier on the K9 of benzo[a]pyrene in Suwannee River humic acid solution and phenanthrene in Aldrich humic acid solution. 3.2 Materials and Methods Suwannee River Humic Acid Reference was obtained from the International Humic Substances Society, Colorado School of Mines, lot number 1R101H. Aldrich Humic Acid was obtained from Aldrich Chemical Company, lot number 01816HH. The humic acid solutions were created by dissolving the humic acid in reagent water at a pH of 10. For some of the experiments, the pH was then reduced 7. Both types of solution were then passed through a 0.45 pm glass filter. Two lots of radiolabeled phenanthrene and one lot of benzo[a]pyrene were obtained from Sigma Chemical. The details are given in Table 3-1. Benzo[a]pyrene was dissolved in a 1:1 toluene:acetone solution and phenanthrene was dissolved in acetone. For some of the solutions, the solvent was then injected directly into the water solution: 1.5 uL and 10 uL of the 1 other spike- place: the s: 31 the phenanthrene and benzo[a]pyrene, respectively. In the other series of experiments, the solvent PAH solutions were spiked into 250 ml glass bottles. Next, the bottles were placed in a hood for at least three days in order to evaporate the solvent. Humic acid solutions were then added. Both the solvent carrier and the evaporated solvent solution bottles were placed in an orbital shaker for at least 16 hours before the reverse phase tests were performed. The concentrations of phenanthrene and benzo[a]pyrene in solution ranged from 0.61-312 ug/L and 50-106 ug/L, respectively. Table 3-1 Radiolabeled PAH data. Phen 1 Phen 2 B[A]P I Product NO. 31,528-1 31,528-1 B9776 Lot NO. 049F9271 049F9271-1 08OH9216 Activity, 13.1 8.3 16.2 mCi/mmol Purity >98% >98% >98% J. T. Baker Empore'" 25 mm C—18 Extraction Disks were used in reverse phase analysis. The EmporeTM Disk was conditioned with 5 mL of 1:1 ethyl acetate:methyl chloride solution, followed by a 5 mL methanol rinse. 105 mL reagent water was then passed through the disk. 5 mL of the PAH/humic acid solution was then filtered though the disk on top of the water meniscus. The disk was eluted sequentially with 5 mL aliquots of ethyl acetate, methylene chloride, and 1:1 ethyl/methylene chloride. All filtering speeds were 24 mL/min. 3.3 benz: A‘ug‘ BAH- 32 3.3 Results and Discussion Reverse phase analysis was conducted on benzo[a]pyrene/Suwanee River’ humic acid solutions. These solutions were prepared with two different sets of conditions, as follows: 1. Benzo[a]pyrene Experimental Condition One (DEC-1) a. Benzo[a]pyrene was dissolved in an acetone/toluene mixture. b. Suwannee River humic acid solution was prepared and then adjusted to a pH of 10. c. Approximately 10 uL of the acetone/toluene mixture was spiked into the humic acid solution. 2. Benzo[a]pyrene Experimental Condition Two (BEC-2) a. Benzo[a]pyrene ‘was dissolved in an acetone/toluene mixture. b. Suwannee River humic acid solution was prepared, adjusted to a pH of 10, and then adjusted to a pH of 7. c. The acetone/toluene mixture was spiked into the mixing bottle, the solvent was evaporated, and then the humic acid solution added. Figure 3-1 shows the results of the reverse phase analyses conducted on EEC-1 and BEC-2 solutions. The percent bound and the K9 were lower in BEC-l, indicating that these values decrease with increasing pH. Also, the BEC-l KP increases with increasing humic acid content. In BEG-2, however, KP decreases I _ .__. .. I . r L _ ‘ _ LI 1 \ A I I I. «J 4 _ :2. . \ \ \ ' 0h.“ . . . . . . . . . . k . 2 . _ . . . a. u 00 II vs is v £ 5 C I z t S C I Z we a. .e C. i.:.(.x2....3..¥:xi.a<.= I 2.3.. 3.2.2.: 3233:1741 5...... 33 3.. 3.. 8 WMTO ’58 20 40 00 00 100 SUWNIIEERNERHIMCACID.PPMTOC [VwA-fixml 20 40 N 00 100 SLMAMEERNERHMACD.PPMTOC LvosuiA-ddxml pH=7, Evaporated Solvent Solutions 100 140 “WWI-[MACDJ’PHTOC 0 20 0 N w 100 120 I'd-“A.“ um] KAI-00 3335333 I” 10 SUWABNEERNBQI'MACDJ’PMTOC 0 20 4O 00 00 100 IN lv+flda-“xm Ph=10, Toluene/Acetone Carrier Solution Figure 3-1 Partitioning results: benzo[a]pyrene in Suwannee river humic acid. with ix to the be:zo:a content Rt phenant 34 with increasing humic acid content. The BEC-2 results compare to those obtained by Landrum and McCarthy in which KP of benzo[a]pyrene decreased with increasing humic acid content(12,27). Reverse phase analysis was conducted on phenanthrene/Aldrich humic acid solutions. These solutions were prepared with two different sets of conditions, as follows: 1. Phenanthrene Experimental Condition One (PEC-l) a. Phenanthrene was dissolved in acetone. b. Aldrich humic acid solution was prepared and then adjusted to a pH of 10. c. Approximately 1.5 [2L of the acetone mixture was spiked into the humic acid solution. 2. Phenanthrene Experimental Condition Two (PEC-2) a. Phenanthrene was dissolved in acetone. b. Aldrich humic acid solution ‘was prepared, adjusted to a pH of 10, and then adjusted to a pH of 7. c. The acetone mixture was spiked into the mixing bottle, the solvent was evaporated, and then the humic acid solution added. Figure 3-2 shows the R5 and percent bound results of reverse phase analysis conducted on PEC-l and PEC-z solutions. As in the BEC tests, the K? and percent bound of PEC-l are lower than in PEC-2. Also, the PEC-l B; decreases with increasing m . . C . :.:. :... 1... z I z 7 ~ . . h- ;2...:..z:.“2.2.‘¢ I.- ..4 «a w.- II I. .4 3. F- ve a» . 1 2.1.5.2.: 42:32.}... N... ~ ur...u..~ 35 8888888 FTIBIBCKIIDTIDHUNISACII1§ 10 12 14 10 18 llIlHKfliFIJIK3Afilb.PFIITIX: vaadxml X I’XC ‘bxc 12 14 10 10 ALENRKfliFRJMKSAKflDnPFIITIXS vawwj 20 pH=7, Evaporated Solvent Solutions ‘510 £314 12 £2 0 FIIBIBCIIID ON‘. 100 IIIIUCIIPIJII3IIICLFTHITINB 150 I v '9000 I. .qfid ‘x una'l § 2200 2000 1000 1000 .1400 1200 1000 000 000 50 100 IIJJRK§1PIIIK3IK=ILFTHITIXS 150 [.w...“ xml Ph=10, Acetone Carrier Solution Figure 3-2 Partitioning results: phenanthrene in Aldrich humic acid. sclve‘ sclut‘ 36 humic acid content. In PEC-Z, however, the K5 increases with increasing humic acid content. In order to determine the effect of pH alone on KP, solvent. carrier 'was ‘used. to introduce PAH into neutral solutions. The results are indicated in Table 3-2. Table 3-2 pH=? and PAH solvent carrier test results. _ r Humic Acid 1 Conc. (L/kg) B[A]P Suwannee 68.9 8785 i 334 ‘ Phen Aldrich 46.6 2168 i 38 fl Phen Aldrich 50.6 ‘ 3026 t 3 fl (1) Average 1 Standard Deviation The Table 3-2 results are lower than those that can be visually interpolated from the neutral, solvent evaporated solution tests (BEC-2 and PEC-2). Also, the Table 3-2 results are higher than those that can be visually interpolated from the pH=10, solvent carrier solution tests (BEC-1 and PEC-1). These results indicate that increasing pH alone leads to decreasing KP. Similarly, Schlautman found that the KP of perylene dissolved in humic solutions decreased with increasing pH(17). Carter obtained the same results with DDT in Pakim Pond humic acid(lS). Figure 3-3 shows how different ratios of phenanthrene to acetone affect the RF of the phenanthrene/Aldrich humic acid solutions. In each instance, 10 uL of acetone was used to 37 PHENANTHRENE IN CARRIER SOLVENT % BOUND TO ALDRICH HUMIC ACID 10 3 14 o 212 §10 0 0.001 0.002 0.003 0.004 0.005 0.006 0.007 awmxnmnrouxwmnuwxem. rv-I-stda-stdxavg PHENANTHRENE IN CARRIER SOLVENT Kp IN ALDRICH HUMIC ACID 0 0.001 0.002 0.003 0.004 0.005 0.006 0.007 lumapmchsaNanJmnumu vWa-fidxmj Figure 3—3 Partitioning results: phenanthrene in Aldrich humic acid. Different amounts of phenanthrene in 10 ul acetone carrier solvent. f‘ f" l). [U 38 spike phenanthrene into 250 mL, 28.3 ppm TOC Aldrich humic acid solutions. A larger phenanthrene to acetone ratio resulted in lower Kp values. Also, these values are lower than those obtained in the evaporated solvent solutions and higher than those obtained in the previous solvent carrier tests. Methanol was used as a comparison. A similar result was obtained. Several researchers have determined that small amounts of methanol in solution have no effect on KP results(23-25). Indeed, several researchers have used methanol(6,12,18,19) and acetone(3,20-22) as carrier solvents to dissolve PAH in humic solutions. These results indicate that the affect of using acetone as a solvent carrier is not only to reduce the R9 of a solution but also to alter the trend of the K§*vs humic acid content graph. A model of the PAH-solvent-humic acid system can be constructed that will contain the components shown in Figure 3-4. The PAH first enters the humic acid solution dissolved in acetone. The following kinetic progression is assumed, setting up an equilibrium condition: 1. The PAH distributes between the water and the solvent phases. Simultaneously, humic acid will equilibrate between the water and the solvent. 2 . PAH distributes between bound and free states in the water phase. 3. The HA-PAH complex equilibrates between the water and the solvent. 39 SOLVENT PAH i—e» HA-PAH «AT A I 3 5 WATER PAH i—S HA-PAH LIQUID PHASE SOLID PHASE- IMSSOLVED IHUNHCAKID Figure 3-4 PAH/Humic Acid/Water/Solvent system. 1, 2, 3, and 4 are PAH distribution coefficients. 5 is the humic acid distribution coefficient. 4. PAH distributes between the bound and the free state in the solvent phase. An extremely hydrophobic solution, like benzo[a]pyrene, will exhibit much higher distribution coefficients 1 ({Pwacetone}/{PAHwator})l 2 ({HA’PAHIHPAHH: and 4 ({HA" PAH}/{PAH}) than a pollutant with lower hydrophobicity like phenanthrene. The interaction of this system with the C-18 reverse phase material will determine the amount of PAH that remains in the filter and, subsequently, the apparent K1, (distribution constant 2 in Figure 2-4) of the solution. Understanding this interaction could help to explain the e V 6' ‘1' If 40 difference in data trends between the solvent carrier and evaporated solvent solutions. 3.4 Experimental Implications This study indicates that there are difficulties associated with the use of a solvent carrier to introduce phenanthrene or benzo[a]pyrene into humic acid solutions. More studies must be conducted to determine the types and amounts of solvent which will not significantly affect the 35 of the PAH-humic acid solutions. 3.5 Summary The percent bound and the Kp of benzo[a]pyrene in Suwannee River humic acid and phenanthrene in Aldrich humic acid decrease with increasing pH. The pH=7, evaporated solvent KP of benzo[a]pyrene decreases with increasing humic acid content. The pH=7, evaporated solvent K5 of phenanthrene in Aldrich Humic acid increases with increasing humic acid content. The pH=10, solvent carrier solutions of both phenanthrene and benzo[a]pyrene exhibit the opposite data trends. The RF of carrier solvent, neutral humic acid solutions are lower than the value obtained in the neutral, evaporated solvent tests and higher than the results obtained in the carrier solvent, pH=10 solution. Increasing the phenanthrene to acetone ratio in the carrier solvent leads to decreasing K9 in the humic acid solution. CHAPTER 4 FURTHER RES EARCE The following are recommendations for future research which would further develop the topics addressed in this work. Research would be conducted using a reverse phase procedure with the Empore‘" Disk. 1. Studies can be conducted to further investigate the effect of carrier solvent use on KP. Different solvents, in varying amounts, can be used to spike PAH into humic acid solution. 2. B; vs humic acid content tests can be conducted at various flow rates to more fully investigate the effect of flow rate on Kp. 3. The combined effect of pH and carrier solvent use on K, can be researched. Tests can be run on solutions of benzo[a]pyrene and phenanthrene at a different pH values. Increasing amounts of humic acid in solution can be used at each pH. 4. The partitioning of other hydrophobic pollutants to 41 42 humic acid may be investigated. APPENDICIES APPENDIX A IF I h! P h h h. \N ‘0 P4 15. APPENDIX A MATERIALS AND METHODS A.1 Materials Suwannee River Humic Acid Reference was obtained from the ‘International Humic Substances Society, Colorado School of Mines, lot number 1R101H. Aldrich Humic Acid was obtained from .Aldrich Chemical Company, lot number 01816HH. TwO lots of radiolabeled phenanthrene and one lot of benzo[a]pyrene were obtained from Sigma Chemical. The details are given in Table A-1. Table A-1 Radiolabeled PAH data. I Phen 1 Phen 2 B[A]P I I Product No. 31,528-1 31,528-1 B9776 Lot No. O49F927l O49F9271-l 080H9216 Activity, 13 . 1 8 . 3 16 . 2 mCi/mmol Purit >98% >98% >98% Waters Sep-PakO C-18 Classic Cartridges and J. T. Baker Empore'" 25 mm C-18 Extraction Disks were used in reverse phase analysis. Details on the various solutions used are given in Table A-2. 43 (I) . (I! 44 Table A"2 Solutions used in experimentation. SW11 Manufacturer aexfies J.T. Baker 9‘“ xylgges J.T. Baker (p methanolj Absolute J.T. Baker ‘ Acetone J .T. Baker x Ethyl Acetate Aldrich Chemical Company Methylene Chloride Mallinckrodt Chrom AR HPLC L Safety--SolveTM Aqueous Research Products r Scintillation International Corporation j Cocktail A.2 Methods A.2.1 Glassware Preparation A. Solution Preparation Glassware Glassware was washed with Multi-Terge liquid alkaline soap (Em Diagnostic Systems) then rinsed thoroughly with deionized water. Next, the glassware was rinsed thoroughly in chromic acid then with ultra-pure deionized water. B. Radiolabeled Experimentation Glassware Glassware was first soaked in water with Multi-Terge alkaline soap. Next, the glassware was soaked in xylene. Then it was rinsed sequentially with xylene, methanol, and hexane. Finally, it was allowed to dry before use. A. 2 . 2 Reagent Water Preparation Experimental reagent water was prepared by first cleaning a 5 gallon glass carboy. The carboy was rinsed with Multi- r" A? 'v'e If 45 Terge filled with ultra-pure deionized water and spiked with 200 mL of 50 g/L sodium persulphate solution. The carboy was allowed to set for 3 days then rinsed thoroughly with ultra- pure deionized water. Ultra-pure deionized water was collected in the carboy and 90 ML of H202 was added in order to create a 60 M solution. The water in the carboy was ozonated for one hour at a rate of approximately 2.8 L/min ozone flow with a Polymetrics, Inc. Model T-408 Ozone Generator. The water was aerated with nitrogen for 15 minutes in order to drive out the carbon. A.2.3 Humic Acid Preparation The humic acid was mixed with reagent water and raised to a pH of about 10 with 0.15 N sodium hydroxide solution. For some of the experiments, the pH was then adjusted to about 7 with a 0.1 M sulfuric acid solution. Then the solution was then filtered through a Millipore 0.45 um glass filter in a vacuum filter system. A.2.4 Radiolabeled Humic Acid Solution Preparation The radiolabeled PAHs were mixed with solvent in order to effectively deliver them into the humic acid solution. The carrier solvents acetone and an 1:1 acetone:toluene solution were used for phenanthrene and benzo[a]pyrene, respectively. A glass syringe was used to deliver 1.5, 10, or 12 uL of the spiked carrier solvent into a glass 250 mL container half 46 full of humic acid solution. Then the bottle was filled with humic acid solution. In the evaporation tests, the spiked carrier solvent was delivered into an empty bottle and the solvent evaporated by setting the bottle in the hood for 3 days. Then, the humic acid solution was added to the bottle and the bottle was capped and put into an orbital shaker at room temperature for at least 18 hours. The concentrations of PAH used in the partitioning experiments are listed in Table A-3. Table A-3 PAH concentration in humic acid solutions. Spiking Concentration Condition Benzo[a]pyrene Solvent 10 50-98.2 ; Benzo[a]pyrene Solvent 7 106.4 ‘ Benzo[a]pyrene Evaporated ‘7 32-91 l Phenanthrene Solvent 10 57-198 Phenanthrene Solvent 7 152, 312 I Phenanthrene Eva-orated 7 0.61-10.9 I A. 2 . 5 Empore'” Disk Reverse Phase Method A.2.5.1 Normal Procedure A. Conditioning A 25 mm Empore‘" C-18 Extraction Disk was first clamped in the funnel/frit vacuum assembly shown in Figure 1-3(a). It was then cleaned by using an automatic pipet with a new tip to 47 add 5 mL of 1:1 ethyl acetate:methylene chloride solution to the reservoir by rinsing the sides of the reservoir at least three times in a circular motion. Then the disk was allowed to soak for 3 minutes. The vacuum was then started and the solution was drawn through the disk at a rate of 24 mL/min. The vacuum was continued for one minute in order to dry the disk. Next, the disk was conditioned by delivering 5 mL methanol into the funnel in a circular motion and allowing the disk to soak for 3 minutes. Then, the vacuum was started and the solvent was drawn through the disk. When only a meniscus of methanol remained, about 15 mL organic-free water was added to the reservoir by rinsing the reservoir at least three times in a circular motion. The vacuuming was continued until a meniscus of water remained, then another aliquot of water was delivered in the same manner. 105 mL (7 aliquots) of water was filtered in this fashion. The vacuuming was continued again until a meniscus of water was left on top of the disk surface, then the vacuum was turned off. B. Reverse Phase Procedure A liquid scintillation vial was fitted into the vacuum chamber shown in Figure 1-3(b). The filtration assembly was then disengaged from the flask and fit into the vacuum chamber assembly with the end of the frit inside the vial. A 5 mL volumetric pipette was rinsed once with 5 mL methanol, twice with 5 mL ultra-pure deionized water, and once with 5 mL of the spiked humic acid solution. Then, the vacuum was turned on 48 to a vacuuming rate of 24 mL/min (400 mm Hg vacuum pressure). The sample was dispensed into the bottom of the reservoir during the filtration so that the disk remained covered by a meniscus of water. After all of 'the solution was filtered through, the vacuuming was continued for one minute in order to dry the disk. The filtration assembly was lifted carefully from the vacuum chamber and set aside. The scintillation vial was then lifted out, capped, and weighed. Next, another empty vial was uncapped and placed onto the vacuum chamber. Then, the filtration assembly was fit into place as before. C. Disk Extraction First, the vacuum was started. Then, using the automatic pipet, 5 mL. of ethyl acetate ‘was slowly added, to the reservoir, forming and maintaining a meniscus in the bottom. In order to dry the disk, vacuuming was continued for 1 minute after the solution was drawn through the frit. The filtration assembly was lifted carefully from the vacuum chamber and set aside. The scintillation vial was then lifted out, capped, and weighed. Another empty vial was uncapped and placed onto the vacuum chamber. Then, the filtration assembly was fit onto the chamber with the frit end inside the vial. Then, methylene chloride, and 1:1 methylene chloride:ethyl acetate solution were added sequentially to the reservoir, in the fashion described above. A new pipette tip was used for each solution. Each tip was first rinsed with the solution before withdrawing the aliquot. A new vial was used for each solution. 49 Then, the funnel was unclamped from the frit and placed in a wash container. Using the forceps, the Empore"‘disk was removed and rinsed thoroughly in the cocktail of a scintillation vial. The disk was disposed of and the vial was capped and set aside. The frit was removed from the flask and set in a wash container. The scintillation vial was lifted out of the vacuum chamber with the removal cap, then, capped and weighed. A 1 ml volumetric pipette was rinsed once with 1 mL methanol, twice with 1 mL ultra-pure deionized water, and once 'with 1 mL of the spiked humic acid solution. Then, 1 ml of the spiked humic acid solution was delivered to three different scintillation vials in order to determine mass balance. Aqueous type liquid scintillation cocktail was added to the vials: 10 mL to the solvent vials, 15 mL to the water filtrate vials, and 19 ml to the mass balance vials. The vials were capped, shaken, and analyzed in the liquid scintillation machine. A.2.5.2 Filtering Speed Test Procedure A. Conditioning See Section A.2.5.1A. B. B. Reverse Phase Procedure A liquid scintillation vial was fitted into the vacuum chamber shown in Figure 1-3(b). The filtration assembly was then disengaged from the flask and fit into the vacuum chamber assembly with the end of the frit inside the vial. A 5 mL 50 volumetric pipette was rinsed once with 5 mL methanol, twice with 5 mL ultra-pure deionized water, once with 5 mL of the spiked humic acid solution, and filled with spiked humic acid solution. Then, the vacuum was turned on to a vacuuming rate of 24 mL/min (400 mm Hg vacuum pressure). The sample was dispensed into the bottom of the funnel during the filtration so that the disk remained covered by a meniscus of water. After all of the solution was filtered through except for a meniscus, the vacuum was turned off. Then, another 5 mL aliquot of the spiked humic acid solution was drawn into the pipette and filtered through the Emporem Disk as before. The filtration assembly was lifted carefully from the vacuum chamber and set aside. The scintillation vial was then lifted out and another empty vial was uncapped and placed onto the vacuum chamber. Then, the filtration assembly was fit onto the chamber with the frit end inside the vial and another 5 mL aliquot filtered through the disk at a high vacuum pressure. This vial was removed as before and another (4)-5 mL aliquots were filtered through the disk in this fashion at decreasing vacuum speeds. Then after the final aliquot, the radiolabeled solution. was filtered through the disk and the vacuum continued for one minute in order to dry the disk. The funnel was then unclamped from the frit and the disk removed. Both the funnel and the frit were placed in a wash container. The disk was placed in a waste container. The above disk conditioning/reverse phase sequence was followed for a new disk using increasing vacuum speeds in the 51 reverse phase procedure. All experimental scintillation vials were capped and weighed. The filtered solution weights and the filtering times were used to determine the filtering speed in mL/min. A 1 mL volumetric pipette was rinsed once with 1 mL methanol, twice with 1 mL ultra-pure deionized water, and once with 1 mL of the spiked humic acid solution. Then, 1 mL of the spiked humic acid solution was delivered to three separate scintillation vials in order to determine mass balance. Aqueous type liquid scintillation cocktail was added to the vials: 15 mL to the water filtrate vials and 19 ml to the mass balance vials. The vials were capped, shaken, and analyzed in the liquid scintillation machine. A. 2 . 6 Sep-PakO Reverse Phase Method A.2 . 6. 1 Normal Procedure A. Conditioning Six new scintillation vials were uncapped and set aside. 2 m1. of methanol was drawn into a 10 mL glass syringe. The syringe was then turned upside down and the plunger was pulled out in order to rinse the syringe. Then the methanol was discarded. This was repeated three times in order to clean the syringe. 10 mL of methanol was then drawn into the syringe, a Sep- PakO Cartridge fitted onto the end, and the methanol was pushed through the cartridge at a constant rate of speed (12 mL/min or 30 mL/min) . The setup was disassembled and the 52 cartridge was set in the first scintillation vial. Next, the syringe was rinsed three times with three 2 mL aliquots of ultra-pure deionized water. Then, 10 mL of water was drawn into the syringe, the Sep-PakG Cartridge was fitted onto the end of the syringe, and the water pushed through the cartridge at a constant rate of speed. In this manner, 100 mL of water was pushed through the cartridge. The cartridge was set in the first scintillation vial between aliquots. B. Reverse Phase Procedure A second syringe was conditioned by rinsing it three times with three 2 mL aliquots of methanol and another three times with 2 mL aliquots of water. Then it was set aside. Three other glass syringes were similarly cleaned but with solvent only: one with ethyl acetate, one with methylene chloride and the other with 1: 1 ethyl acetate:methylene chloride. Humic acid solution spiked with radiolabeled PAH was poured into a beaker. The first syringe was rinsed with 5 mL of solution. 5 m1. of spiked humic acid solution was drawn into the syringe, the conditioned Sep-PakO Cartridge fitted onto the end, and the solution pushed through at a constant rate of speed into the second scintillation vial. The vial was capped and set aside. The cartridge was set-in the third vial. The second syringe was then filled with 5 mL of water, the Sep-PakO fitted on to the end, and the water pushed through at a constant speed into the third scintillation vial. Then, the cartridge was placed into the fourth vial. The third 53 ‘vial was capped and set aside. C. Cartridge Extraction 5 mL of ethyl acetate was drawn into the third syringe, ‘the Sep-PakO cartridge fitted onto the end, and the solution jpushed through at a constant speed into the fourth vial. The cartridge was placed into the fifth vial and the fourth vial was capped and set aside. Similarly, methylene chloride and 1:1 ethyl acetate:methylene chloride were used sequentially to elute the cartridge. A 1 mL volumetric pipette was rinsed once with 1 mL ‘methanol, twice with 1 mL ultra-pure deionized water, and once 'with.1 mL of the spiked humic acid solution. Then, 1 mL of the spiked humic acid solution was delivered to three separate scintillation vials in order to determine mass balance. .Aqueous type liquid scintillation cocktail was added to the scintillation vials: 10 mL to the solvent vials, 15 mL to the 'water vials, and 19 mL to the mass balance vials. The vials were capped, shaken, and analyzed in the liquid scintillation machine. The syringes were disassembled and placed in the wash container. A.2.6.2 Filtering Speed Test Procedure A. Conditioning See Section A.2.6.1A. B. Reverse Phase Procedure Humic acid solution spiked with radiolabeled PAH was poured into a beaker. The syringe was rinsed with 5 mL of 54 solution. 10 mL of spiked humic acid solution was drawn into the syringe, the conditioned Sep-PakO Cartridge fitted onto the end, and the solution pushed through at a constant rate of speed into the second scintillation vial. The vial was capped and set aside. The cartridge was set in the third vial. The syringe was then filled with 5 mL of spiked humic acid solution, the Sep-PakO fitted on to the end, and the water pushed through at 6 mL/min into the third scintillation vial. Then, the cartridge was placed into the fourth vial. The third vial was capped and set aside. (3)-5 mL aliquots were delivered in this manner at increasing speeds of 12 mL/min, 20 mL/min, and 30 mL/min. After the last aliquot was filtered through the cartridge, the syringe was disconnected from the cartridge. The syringe was placed in a wash container and the cartridge discarded . The previously described filtering speed test was repeated using a new cartridge and syringe. Filtering speeds were started high and then decreased in the following sequence: 30 mL/min, 20 mL/min, 12 mL/min, and 6 mL/min. After the last aliquot was filtered through the cartridge, the syringe and the cartridge were disconnected. The syringe was placed in a wash container and the cartridge discarded. A 1 mL volumetric pipette was rinsed once with 1 mL methanol, twice with 1 mL ultra-pure deionized water, and once with 1 m1. of the spiked humic acid solution. Then, 1 mL of the spiked humic acid solution was delivered to three separate scintillation vials in order to determine mass balance. -:—*-‘ r — _- 1‘ 55 Aqueous type liquid scintillation cocktail was added to the scintillation vials: 15 mL to the water vials and 19 mL to the :mass balance ‘vials. The 'vials 'were capped, shaken, and analyzed in the liquid scintillation machine. The syringes were disassembled and placed in the wash container. A.2.7 Total Organic Carbon Analysis 50 g/L sodium persulfate and 5% phosphoric acid solutions were used in the total organic carbon analyzer. The 50 g/L sodium persulfate solution was prepared by first dissolving 50 g of Nazszoa into enough ultra-pure deionized water in order to make 1 liter solution. Then the solution was purified by placing it in a reagent bottle with the cap loosely on top and heated until it just began to boil. The cap was tightened and the bottle placed in water to cool. The 0.1. Corporation Mbdel 700 Total Organic Carbon (TOC) Analyzer provides reagent bottle purge lines in order to purge the solution of C02 present from the oxidation of organics with nitrogen automatically during machine operation. The 5% phosphoric acid solution was prepared by adding 59 mL of 85% H3PO. to enough ultra-pure deionized water to create 1 liter of reagent solution. The acid solution was purified by placing it in a reagent bottle, adding 10 mL of the persulfate solution, placing the cap loosely on top, and placing it in boiling water for 2 hours. As before, the solution was purged during TOC machine operation. KHP was dried to constant mass by placing an amount of it range “v- 6 at. _ A.2.8 the SI COIEEC the 5 indie! Scint: 56 in an oven at 100°C. 1, 000 mg/L carbon standards were prepared by adding 2.128 g of KHP and enough reagent water in order to create 1 liter of solution. Dilutions were made with reagent water from this solution. The machine curve was set by injecting 20 pl of 1,000 mg\L into the machine. 5 standards were injected into the machine in order to create a standard curve. The amount of liquid injected was calculated in order to obtain 5 to 30 ug range of carbon in the machine. The samples were injected first to roughly determine the range needed for the standards. A.2.8 Liquid Scintillation Analysis Background values were determined by running one each of the Sep-PakG and Empore'" Disk reverse phase experiments with 5 mL of unspiked humic acid solution. All solutions were collected in scintillation vials as was normal, combined with the amounts of liquid scintillation cocktail previously indicted, and counted in the Packard 1500 Tri-CarbO Liquid Scintillation Analyzer (LSA) . These values were subtracted from their corresponding experimental raw scintillation counts (before quench adjustment). The LSA efficiency was determined by counting a standard for five minutes and dividing the number of counts by the standard value. The efficiency was 94.5%. In order to determine the quenching of the humic acid solutions, Aldrich Humic Acid was used to create 12 solutions increasing in humic acid content from 0 to 180 ppm total the 1 Cam I 0.2 Value RiVer Grier 57 organic content (TOC) . 1 mL aliquots were mixed in a scintillation vial with 19 mL cocktail and 10 uL of radiolabeled acetone/phenanthrene. 5 mL aliquots were mixed in a scintillation vial with 15 mL cocktail and 10 #1.. of radiolabeled acetone/phenanthrene. The standard was prepared with 20 mL of cocktail and 10 ALL of radiolabeled acetone/phenanthrene. The vials were each counted for 5 minutes each. Each vial was counted three times. The average regression lines are shown in Figure A-l. The r2 values of the 1 mL and the 5 mL regression lines are 0.975 and 0.997, respectively . Suwannee River Humic Acid quench was determined by using the log of the TSIE values obtained by the Packard 1500 Tri- CarbO LSA. For Aldrich Humic Acid, a curve was prepared of the % quench vs the log TSIE and is shown in Figure A-2. The r2 value was 0.9924. The log TSIE obtained from the Suwannee River Humic Acid water samples was applied to the curve in order to obtain the quench value . In order to determine the ethyl acetate, methylene chloride, and 1:1 ethyl acetate:methylene chloride solution quenchings, 0, 1, 2, 3, 4, and 5 mL aliquots of ethyl acetate were added separately to 10 pi. radiolabeled acetone/phenanthrene solution and 10 mL of cocktail in scintillation vials. The resultant curves are shown in Figure 3 . 5. Since the r2 value of the ethyl acetate quench regression curve was less than 0.50, the curve was used in the raw form to interpolate the data. The r2 value of the methylene 58 80 QUENCH. % A O O O N O / .——-—I-""‘- MW 50 100 150 ALDRICH HUMIC ACID CONTENT, PPM TOC +1mL—v—5mL 200 Figure A-1 The quenching effect of Aldrich humic acid content in liquid scintillation. Regression lines are shown. solutions were created with either 1 mL or 5 mL humic acid solution and liquid scintillation cocktail. ZOmL 59 1 ML REGRESSION CURVE Log TSIE 5 ML REGRESSION CURVE 2.4 g I» 22 x 2 L9 .. :2 1.8 \ gm \ \\- 1 4 I \ 1 2 \ T I 1 -20 0 20 4O 00 00 Qumch. 16 Fi Ne A-2 Log TSIE values compared to solution quench. I Q CLO! Iu‘ A‘ LA‘UI new: time: 60 chloride and 1:1 solution are 0.999 and 0.995, respectively. In order to determine the ethyl acetate, methylene chloride , and 1:1 ethyl acetate:methylene chloride solution quenchings for the Sep-PakO by running the procedure three times and collecting the solvents. These solutions were combined with 10 [IL of radiolabeled acetone/phenanthrene solution and 10 mL scintillation cocktail. 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N000 w 00.0..00 _. 00.N_.00.. 0.0000 _. 0.N000 .. 0N00 _. 0>< 0 0.00N00 0000 0 1.00000 0.0000 _. 0.0000 ... 0.0N00 w 00 ..0.. 0.0N 03. 1.033 0.0 ..0: 0.0—.30 0.0001. 0.0000 .. v.00N0 F 0.00 ..0.. N 0000 _. N680 .. N.0000 _. N 23m :00 0.00000 0. ..N00w 00000 0.00000 00000 0.00000 0.00N00 N.0w 0: 0.0001. 0.N00: 0.0002. N000: 0.N0 000 0.00 000 0 30.. _. N. 00000 0.0000 .. 0.0..000 _. 0 N w ..2 0 0 N _. ..E v 0 N _. ..2 0 0 N _. ..2 N 0 N w ..2 w 0..—km 0:. 0 N .. Omhzoo 221 mhuomdw m 332.2% LIST 0? REFERENCES 10. 11. 12. 13. LIST 0? REFERENCES Schwarzenbach, R.P.; Gschwend, P.M.; Imboden, D.M. "Environmental Organic Chemistry"; John Wiley & Sons: New York, NY, 1993, pp. 255—341, 618-625. Verschueren, K. "Handbook of Environmental Data on Organic Chemicals"; Van NOstrand Reinhold: New York, NY, 1983, pp. 263-277, 970-972. Black, M.C.; McCarthy, J.F. Environ. Tox. Chem. 1988, 7, 593. Johnsen, 8.; Kukkonen, J.; Grande, M. Sci. Tbt. Environ. 1989, 67, 691. 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