United States Environmental Protection Agency Municipal Environmental Research Laboratory Cincinnati OH 45268 EPA-600/2-80-030 March 1980 Research and Development &EPA Analytical Procedures for Determining Organic Priority Pollutants in Municipal Sludges ------- RESEARCH REPORTING SERIES Research reports of the Office of Research and Development, U.S. Environmental Protection Agency, have been grouped into nine series. These nine broad cate- gories were established to facilitate further development and application of en- vironmental technology. Elimination of traditional grouping was consciously planned to foster technology transfer and a maximum interface in related fields. The nine series are: 1. Environmental Health Effects Research 2. Environmental Protection Technology 3. Ecological Research 4. Environmental Monitoring 5. Socioeconomic Environmental Studies 6. Scientific and Technical Assessment Reports (STAR) 7. Interagency Energy-Environment Research and Development 8. "Special" Reports 9. Miscellaneous Reports This report has been assigned to the ENVIRONMENTAL PROTECTION TECH- NOLOGY series. This series describes research performed to develop and dem- onstrate instrumentation, equipment, and methodology to repair or prevent en- vironmental degradation from point and non-point sources of pollution. This work provides the new or improved technology required for the control and treatment of pollution sources to meet environmental quality standards. This document is available to the public through the National Technical Informa- tion Service, Springfield, Virginia 22161. ------- EPA-600/2-80-030 March 1980 ANALYTICAL PROCEDURES FOR DETERMINING ORGANIC PRIORITY POLLUTANTS IN MUNICIPAL SLUDGES by J. S. Warner, G. A. Jungclaus, T. M. Engel, R. M. Riggin, and C. C. Chuang Battelle Columbus Laboratories Columbus, Ohio 43201 Contract No. 68-03-2624 Project Officer Richard A. Dobbs Wastewater Research Division Municipal Environmental Research Laboratory Cincinnati, Ohio 45268 MUNICIPAL ENVIRONMENTAL RESEARCH LABORATORY OFFICE OF RESEARCH AND DEVELOPMENT U.S. ENVIRONMENTAL PROTECTION AGENCY CINCINNATI, OHIO 45268 ------- DISCLAIMER This report has been reviewed by the Municipal Environmental Research Laboratory, U. S. Environmental Protection Agency, and approved for publica- tion. Approval does not signify that the contents necessarily reflect the views and policies, of the U.S. Environmental Protection Agency, nor does mention of trade names or commercial products constitute endorsement or recommendation for use. ii ------- FOREWORD The Environmental Protection Agency was created because of increasing public and government concern about the dangers of pollution to the health and welfare of the American people. Noxious air, foul water, and spoiled land are tragic testimony to the deterioration of our natural environment. The complexity of that environment and the interplay between its components require a concentrated and integrated attack on the problem. Research and development is that necessary first step in problem solution and it involves defining the problem, measuring its impact, and searching for solutions. The Municipal Environmental Research Laboratory develops new and improved technology and systems for the prevention, treat- ment, and management of wastewater and solid and hazardous waste pollutant discharges from municipal and community sources, for the preservation and treatment of public drinking water supplies, and to minimize the adverse economic, social, health, and aesthetic effects of pollution. This publication is one of the products of that research; a most vital communications link between the researcher and the user community. This report describes analytical procedures developed for the deter- mination of semivolatile organic priority pollutants in municipal sludge at levels down to 0.01 yg/g. 111 ------- ABSTRACT An analytical procedure was developed for the determination of 54 semivolatile organic priority pollutants in sludge at levels down to 0.01 yg/g wet weight. The procedure involved extraction with methylene chloride or chloroform, cleanup of groups of compounds having common properties, and in most cases analysis of the fractions by GC-MS using high-resolution glass capillary columns and selected ion searches. The final analyses involved the analysis of three separate fractions, namely benzidines, phenols, and neutrals. The benzidines were determined by HPLC analysis using an electrochemical detector instead of by GC-MS because GC-MS sensitivity for these compounds was too low. Quantitation in the GC-MS analyses involved the internal standard method applied to selected ion responses. Relative response factors obtained from the analysis of standard solutions were used as correction factors. The cleanup steps were considered the most critical parts of the program. Benzidines were cleaned up from neutral and acidic components by a simple acid-base extraction procedure. Phenols were cleaned up from neutral components by acid-base extraction. Fatty acids, a major inter- ference, were separated from phenols by gel permeation chromatography using Bio-Beads S-X8. Neutrals were cleaned up from acidic components by acid-base extraction. Triglycerides, a major interference in the neutrals, were removed by gel permeation chromatography using Bio-Beads S-X8. Saturated hydrocarbons, another major interference in the neutrals, were removed by adsorption chromatography using activated silica gel. This step also re- moved highly polar components. The procedure was applied to the analysis of sludge spiked with the priority pollutants of concern at a level of 0.05 yg/g, wet weight basis (1 yg/g dry weight basis for 5% solids sludge). Recoveries were generally good and in many cases were greater than 50 percent. For many of the phthalates and aromatic hydrocarbons, recoveries of several hundred percent were obtained indicative of their presence in the starting sludge. Some of the chloroethers, nitro compounds, and phenols were not recovered possibly because of retention by particulate material in the sludge , degradation during the 24-hour equilibration period, or loss in the relatively large amount of caustic wash required to remove the fatty acids. Good recoveries were obtained for benzidines even at 0.25 yg/g dry weight. IV ------- CONTENTS Foreword ill Abstract iv Figures vi Tables vi 1. Introduction 1 2. Conclusions 3 3. Recommendations 4 4. Statement of the Problem 5 5. Overall Approach 6 6. Experimental Studies 9 Extraction 9 Removal of Acids from Neutrals 11 GPC Studies 12 Sephadex LH-20 Chromatography 12 BioBeads Chromatography 14 Silica Gel Cleanup 18 Packed Column GC-MS Analysis 18 Analysis of Phenols 18 Determination of Pesticides 19 Analysis of Spiked and Nonspiked Samples 19 Appendix S-100 Method for Semivolatile Organic Components 33 v ------- FIGURES Number page 1 Scheme for determination of semivolatile priority pollutants in sludge 8 2 Elution profiles of whole sludge extract on (a) Bio-Beads S-X12, (b) Bio-Beads S-X8, and (c) Bio-Beads S-X4 15 3 Elution profiles of (a) whole sludge extract, (b) fatty acids, and (c) triglycerides on Bio-Beads S-X8 16 TABLES Number Page 1 EPA Semivolatile Organic Priority Pollutants 2 2 Yields From Various Extractions Methods 10 3 Repetitive Homogenization-Extraction of Sludge With DCM. ... 11 4 Test Solvent Systems For Sephadex LH-20 Fractionations .... 13 5 Capacity Factors of Reference Compounds Eluted with Methylene Chloride from Bio-Beads S-X8 17 6 Comparison of Packed Column and Capillary Column GC Analysis for Determining the Recovery of Priority Pollutants from Digested Municipal Sludge 20 7 Recovery of Priority Pollutants from Water 23 8 Recovery of Priority Pollutants from Digested Municipal Sludge 26 9 Recovery of Priority Pollutants from Raw Sludge 29 VI ------- SECTION 1 INTRODUCTION The U.S. Environmental Protection Agency has designated 114 organic chemicals as priority pollutants and is setting limits on the discharge levels permitted for these pollutants in wastewater, sludge, landfill leachate, etc. In order to establish programs for compliance with the discharge limits satisfactory analytical methodology is needed for use by the dischargers and by EPA. The objective of the study described in this report was the development of efficient methodology for the determination of 54 of the semivolatile organic priority pollutants in municipal sewage sludge. Those 54 chemicals were comprised of 11 acids (phenols), 2 bases (benzidines), 16 polycyclic aromatic hydrocarbons, 6 phthalates, 2 nitros- amines, 3 chloroalkyl ethers, 8 chlorinated hydrocarbons, and 6 miscellane- ous neutral compounds. They are listed in Table 1. The detection limit desired was 0.3 yg/g of sludge on a dry weight basis. The sludge of interest included both primary and activated sludge prior to treatment by an anaerobic digester and the digested sludge. ------- TABLE 1. EPA SEMIVOLATILE ORGANIC PRIORITY POLLUTANTS 1. 2. 3. 4. 5. 6. 7. 1. 2. 3. 1. 2. 3. 4. Polycyclic Aromatic Hydrocarbon Acenaphthene Acenaphthylene Anthracene Benzo(a)anthracene Benzo(b)fluoranthene Benzo(k)fluoranthene Benzo(g,h,i)perylene Benzo(a)pyrene 9. Chrysene 10. Dibenzo(a,g)anthracene 11. Fluoranthene 12. Fluorene 13. Indeno(l,2,3-cd)pyrene 14. Naphthalene 15. Phenanthrene 16. Pyrene Phthalates Bis(2-ethylhexyl) phthalate Butylbenzyl phthalate Diethyl phthalate 4. Dimethyl phthalate 5. Di-n-butyl phthalate 6. Di-n-octyl phthalate Chlorinated Hydrocarbons 2-Chloronaphthalene 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene 5. Hexachlorobenzene 6. 1,2,4-Trichlorobenzene 7. Hexachlorobutadiene 8. Hexachlorocyclopentadiene Chloroalkyl Ethers 1. Bis-(2-chloroethyl) ether 3. Bis-(2-chloroisopropyl) ether 2. Bis-(2-chloroethoxy)methane Nitrosamines 1. N-Nitrosodiethylamine 2. N-Nitrosodiphenylamine Miscellaneous Neutrals 1. 4-Bromophenyl phenyl ether 2. 4-Chlorophenyl phenyl ether 3. 2,4-Dinitrotoluene 1. 4-Chloro-3-methylphenol 2. 2-Chlorophenol 3. 2,4-Dichlorophenol 4. 2,4-Dimethylphenol 5. 4,6-Dinitro-2-methylphenol 6. 2,4-Dinitrophenol 4. 2,6-Dinitrotoluene 5. Isophorone 6. Nitrobenzene Acids 7. 2-Nitrophenol 8., 4-Nitrophenol 9. Pentachlorophenol 10.. Phenol 11. 2,4,6-Trichlorophenol Bases Benzidine 2. 3,3'-Dichlorobenzidine ------- SECTION 2 CONCLUSIONS The analysis scheme developed works very well in most cases for the analysis of neutrals, phenols, benzidines, pesticides, and PCBs in raw and digested sludge. The combination of extractions, gel permeation chromato- graphy, and adsorption chromatography used for cleanup is an effective approach. The use of HPLC with an electrochemical detector is highly sensitive and selective for the determination of benzidines. The computer- ized GC-MS system used with glass capillary columns is highly effective as a sensitive and selective method for detecting and quantitating nearly all of the other semivolatile organic priority pollutants. The primary remaining problems are (1) poor recoveries of nitrophenols, (2) poor recoveries of some of the more polar neutrals, namely, the nitro compounds, chloroethers, and isophorone, and (3) poor quantitative re- producibility. These problems could be caused by degradation during the 24-hour equilibration step, retention by the particulate material of the sludge, loss to the aqueous phase facilitated by soaps during caustic extraction, or alteration of separation patterns caused by large amounts of fatty acids. A systematic study should be made of each of these possible causes. Such a study could be carried out very efficiently without its being a major effort by using fatty acid and priority pollutant standards and determining recoveries by GC or HPLC. ------- SECTION 3 RECOMMENDATIONS Determine the recoveries and reproducibilities of recovery of chloro- ether and nitrobenzenes, with and without the addition of sludge extract- ables, in each of the following cleanup steps: (a) caustic extraction, (b) Bio-Beads S-X8 chromatography, and (c) silica gel chromatography. Determine the recoveries and reproducibilities of recovery of nitrophenols with and without the addition of sludge extractables, in each of the following cleanup steps: (a) Bio-Beads S-X8 chromatography, (b) caustic extraction, and (c) methylene chloride extraction of the acidified caustic extract. Determine the effect of equilibration time on the recoveries and reproducibilities of recovery of nitrophenols and polar neutrals from spiked sludge. Determine the effect of adding salt or a water-miscible organic solvent on the recoveries and reproducibilities of recovery of nitrophenols and polar, neutrals from spiked sludge. Use glass capillary column gas chromatography for the analyses of neutrals required in the above studies using a Hall detector for chloro- ethers and a thermionic detector in the nitrogen mode for the nitrobenzenes, Use HPLC with a variable wavelength UV detector for the analyses of nitrophenols required in the above studies. ------- SECTION 4 STATEMENT OF THE PROBLEM Sludge generally contains 1 to 8 percent solids on a dry weight basis and those solids in turn contain 10 to 15 percent solvent-extractable organic material. The desired detection limit of 0.3 yg/g on a dry weight basis thus corresponds to 2 to 3 yg/g of organic extractable material. The bulk of the extractable material is expected to be components such as petroleum fuels, lubricating oils, asphalt, fats, fatty acids, and deter- gents. The analysis problem can be equated to that of looking for a few parts per million of a lipophilic component in crankcase oil or cooking oil. In this perspective the complexity of the problem is immediately apparent. Extensive cleanup is desirable; however, the broad range of physical properties of the various priority pollutants makes it impossible to separate them as a single group. A combination of cleanup methods, detector sensitivity, and detector selectivity is needed. If the GC-MS detection limit is 10 ng and one percent of the sample extract, e.g. 2 yl out of a total of 200 yl, is injected, at least 100 mg of total extractable material must be dealt with in the cleanup process. If the maximum concentration of total material that can be handled satisfactorily by the GC-MS system is 10 mg/ml (2 mg/200 yl) then at least a 98 percent cleanup is required. If the GC-MS detection limit is higher, an even greater degree of cleanup is required. ------- SECTION 5 OVERALL APPROACH The basic approach used for determining semivolatile priority pollutants in sludge involved extraction with methylene chloride or chloro- form, cleanup of groups of compounds having common properties, and analysis by GC-MS using high-resolution glass capillary columns and selected ion searches. The benzidines were an exception in that they were determined by HPLC using an electrochemical detector according to the method of Riggin and Howard*. Several approaches to extraction were studied including freezedrying followed by Soxhlet extraction, methanol-drying followed by Soxhlet extract- ion, azeotropic drying and the extraction associated with it, and repetitive equilibration with solvent. The latter method, involving homogenizing to promote equilibration, centrifuging to promote phase separation, and withdrawal of the organic layer with a syringe, was chosen as an effective and convenient method. Also less decomposition would be expected using this method because of the absence of heat. The 54 compounds of concern are comprised of neutrals, phenols and benzidines. A separate aliquot of the sludge sample was used for the deter- mination of each of the three groups of compounds. The benzidines were cleaned up from the acidic and neutral components present in a chloroform extract by extraction into strong aqueous acid followed by neutralization and reextraction into chloroform. Because of the difficulty of protonating dichlorobenzidine, a very strong acid, 1.0.NH2S04, is required for this step. The use of 0.1N H2S04 is entirely inadequate. All hydrocarbons, triglycerides and fatty acids are removed in this process. The use of HPLC and the selectivity of the electrochemical detector provide additional discrimination from interferences. The phenols were cleaned up from neutral and basic components present in a methylene chloride extract by a combination of gel permeation chromato- graphy (GPC) and acid-base extraction. The extract was first passed through a GPC column of Bio-Beads S-X8, a porous styrene-divinylbenzene copolymer, with methylene chloride as the eluting solvent. Higher molecular weight components, primarily the triglycerides, long-chain hydrocarbons, and long- chain fatty acids, elute prior to the phenols and were thus removed by this R. M. Riggin and C. C. Howard, Anal. Chem. , 51, 210 (1979) ------- step. The phenols, which were contained in a lower molecular weight fraction, were cleaned up from the remaining neutral and basic components by extraction into aqueous base followed by acidification and reextraction into methylene chloride. The neutrals in a separate methylene chloride extract were separated from phenols and the large amounts of fatty acids by caustic extraction using rather large volumes of 0.1N NaOH in 10% NaCl. This left a solvent extract containing the neutral priority pollutants mixed with major amounts of triglycerides, hydrocarbons, and more polar interfering neutral components, Gel permeation chromatography, identical to that described for cleanup of phenols, was applied to the neutrals also. In this case the triglycerides eluted prior to the priority pollutants but separation of many of the hydro- carbons from the relatively large phthalate esters was not possible. There- fore, after the removal of the triglycerides by GPC, two additional GPC fractions were collected, the first of which was cleaned up further by adsorption chromatography on activated silica gel. The hydrocarbons were eluted first from the silica gel and discarded, followed by the more polar neutral components, the phthalates, chloroethers, nitroaromatics and isophorone. Any highly polar compounds were left on the silica gel column. The aromatic hydrocarbons and halocarbons were obtained in a second GPC fraction which was analyzed by GC-MS without further cleanup. The overall analysis scheme described above, involving the use of three separate sludge samples for phenols, neutrals, and benzidines, respectively, is outlined in Figure 1. The final analyses entailed HPLC- EC analysis of a benzidine fraction and GC-MS analysis of a methylated phenol fraction and combined neutral fraction. The largest group of frequently occurring interfering compounds were the alkylbenzenes and alkylnaphthalenes present in the neutrals. Since these compounds have physical properties similar to those of dichlorobenzenes and naphthalene they cannot be Temoved—thus the selectivity of the GC-MS system must be relied upon for the determination of dichlorobenzenes and naphthalene in the presence of such interferences. It should also be recognized however, that the alkylbenzenes and alkylnaphthalenes may represent nearly as great an environmental hazard as some of the priority pollutants and thus their presence should be of interest. The GC-MS system used employed high-resolution glass capillary columns and selected ion searching. Such a system provided high sensitivity, high resolution of priority pollutants from any remaining interferences, and high selectivity of detector responses. Quantitation was based upon the total area of the selected ions of a priority pollutant peak relative to the total area of the selected ions of an internal standard peak. Relative response factors obtained from the analysis of standard solutions were used as correction factors in the calculations of priority pollutant concentrations. ------- SLUDGE 00 JOO g Wet Weight Acidify With KHS04 Extract With CU2C1 Cleanup Using Bio-Beads S-X8 Extract With 0.2 N NaOH I Acidify Aqueous Phase With 6 N HC1 | Extract With CH2C12 | Methylate .Using C112N2 Analyze by CC-MS PHENOLS 100 g Wet Weight Acidify With K1ISO, Extract With CH C12 Wash With 0.1 N NaOH Fractionate Using Bio-Beads S-X8 Collect Two Fractions, GPC-1 and GPC-2 Cleanup GPC-1 Using Activated Silica Gel Combine GPC-2 and Cleaned up GPC-1 Analyze by GC-MS NEUTRALS 10 g Wet Weight Dilute with 0.1 M Phosphate Buffer, pH7 Extract With C1IC1 Preserved With Ethanol Extract With 2 N lUSO, T Neutralize Aqueous Extract to pll 6-7 Usine 1 M Na PO, Extract With ClICK Add Methanol to CHC1., Extract and Concentrate Dilute With 0.1 M Acetate Buffer, pll 4.7 J Analyze by HPLC Using Electrochemical Detector BENZIDINES Figure 1. Scheme for determination of semi volatile priority pollutants in sludge. ------- SECTION 6 EXPERIMENTAL STUDIES The experimental details of the analytical procedure developed for this program are described in Appendix A. The various studies involved in developing and evaluating the procedure are discussed below. Although there was not sufficient time for a systematic study of recoveries of all of the compounds from each step during the development of the procedure various modifications were studied briefly. EXTRACTION Several methods of extraction were studied including freeze drying followed by Soxhlet extraction, methanol-drying followed by Soxhlet extractionsazeotropic drying and the extraction associated with it, and repetitive equilibration with solvent. Since the extraction step was studied prior to the development of efficient cleanup methods, the effective- ness of extraction was based on the yield of total extractable material obtained. Data comparing the effectiveness of various extraction techniques for both raw and digested sludge are shown in Table 2. The values given are in weight per cent of dry weight of sludge. The raw sludge was 4.0% solids by weight and the digested sludge was 2.8% solids by weight. The weight per cent of extractables recovered by each method was based on the residue weight obtained by evaporating the solvent from a 100-yl aliquot of the extract. The data suggest that extraction method 6, 7, 8, or 9 would be the best choice for the most efficient removal of the total organic material from sludge. Homogenization of the sludge with dichloromethane (Method 8) was selected for subsequent studies. The method is very rapid and simple and is carried out at room temperature. A Tekmar Tissumiser was used for the homogenization. Only Teflon and stainless steel, which are easily cleaned prior to each extraction, contact the sample. Following homogenization the sample is centirfuged and the organic layer withdrawn with a syringe. The process is repeated four times to give a total of five extracts which are combined and dried over magnesium sulfate. It is desirable to avoid methanol in the extracting solvent because it must be removed prior to subsequent cleanup on silica gel. This additional step would require extra effort and presents a potential loss of priority ------- TABLE 2. YIELDS FROM VARIOUS EXTRACTIONS METHODS Yield, mg per 1QQ mg of dry sludge Description of Extraction Method RawDigested 1. Soxhlet extract with MeOH then 1:1 benzene- MeOH 18.4 7.6 2. Freeze dry; Soxhlet extract with DCM3 18.7 6.9 3. Freeze dry; Soxhlet extract with 1:1 benzene- MeOH 20.2 4. MeOH wash; Soxhlet extract with 1:1 benzene- MeOH 15.0 9.0 5. MeOH wash; Soxhlet extract with DCM 17.4 8.3 6. MeOH wash; Soxhlet extract with MeOH then fresh 1:1 benzene-MeOH 25.6 11.3 7. Azeotropic drying with EDC ; centrifugation 25.6 11.6 8. Homogenization with DCM; centrifugation 22.4 12.1 9. Homogenization with 1:1 DCM-MeOH; centri- fugation 26.3 ,12.7 a. Dichloromethane (methylene chloride) b. Ethylene dichloride ------- pollutants as great as the possible increase recovery during the initial extraction. The effectiveness of each of the five homogenization-extraction steps using dichloromethane (DCM) as the solvent was determined. For this study lOOg of a wet digested sludge was extracted five times with dichloromethane. The results, shown in Table 3, indicate that the first three extractions remove 95 per cent of the total organic material obtained from the five extractions. Therefore only three extractions were used in subsequent studies. TABLE 3. REPETITIVE HOMOGENIZATION-EXTRACTION OF SLUDGE WITH DCM Extraction Step 1 2 3 4 5 Weight of Total Extract, mg 106 79 15 4 6 210 Weight Per cent of Total 50 38 7 2 3 100 REMOVAL OF ACIDS FROM NEUTRALS The approach initially tried for obtaining the neutrals involved start- ing with a single methylene chloride extract to obtain both a neutral fraction and an acid fraction. The acids were removed from the neutrals by extraction of the extract from lOOg of wet sludge with four 50-ml portions of 0.2 £J NaOH. The combined aqueous layers were acidified and back ex- tracted with methylene chloride to give an acid fraction containing fatty acids and phenols. However, the sludge used contained very high levels of fatty acids, 1 to 2% on a wet weight basis, which formed so much soap that the caustic extraction was not efficient. Some of the netural components stayed in the soap solution and some of the soaps stayed in the methylene chloride. Emulsions were also a problem. Because of the above problems the extraction scheme was modified by greatly increasing the amount of dilute caustic used for washing out fatty acids and by adding salt to the water to avoid emulsion formation. However, the large amount of water used made it difficult to back extract the nitrophenols into methylene chloride after acidification. Consequently a separate sludge extract was used for obtaining a cleaned up phenol fraction in which gel permeation chromatography (GPC) was used as the first cleanup step as will be discussed below. 11 ------- The neutral fraction was further fractionated by GPC to give one fract- ion containing the phthalates and the more polar priority pollutants and a second fraction containing the aromatic hydrocarbons, halocarbons, and ethers. Only the first fraction was cleaned up further by silica gel chromatography. The two fractions were then combined in most cases to give only one final neutral extract for GC-MS analysis. GPC STUDIES Sephadex LH-20 Chromatography Sephadex LH-20, a modified dextran gel was studied for use as a gel permeation fractionation step to clean up groups of compounds on the basis of molecular size. Three major conditions had to be considered. First, the solvent system had to be compatible with that of the sludge extract. Second, since Sephadex LH-20 is less dense than many common organic solvents, densi- ties of different solvents had to be taken into consideration. Third, the solvent system chosen had to optimize separations between different sizes of molecules. Since the concentrated sludge extract was in methylene chloride, the first choice was to use methylene chloride as the eluting solvent in the fractionation step. Since the Sephadex LH-20 was less dense than methylene chloride, this necessitated the use of an upward-flow liquid chromatographic apparatus. A 750 mm x 15 mm I.D. upward flow column was obtained for this purpose and packed with approximately 50 grams of Sephadex LH-20 swelled in methylene chloride. The apparatus was found to be an effective means of fractionating the sludge extracts but it was determined after actual applica- tion of sludge extracts that large amounts of material remained on the col- umn after elution of the priority pollutants. This indicated the need for washing the packing with a solvent which would remove the adsorbed material or using fresh Sephadex LH-20 for each sample. Either alternative necessi- tated repacking the upward flow column for each sample application. Since it took considerable time to pack the upward flow apparatus, a compatible solvent system for use in a downward flow system was considered to be a time- saving alternative. The choices of solvent systems in which the sludge was relatively solu- ble were somewhat limited. The sludge extract was soluble in such solvents as methylene chloride, ethylene dichloride, and benzene. The extract was moderately soluble in acetone, slightly soluble in n-butyl chloride and cyclopentane, and insoluble in methanol, ethanol, and isopropanol. Studies were also done to determine which mixtures of these and similar solvents would allow the use of a downward flow apparatus and also would be compatible with the sludge extract. Nine solvent systems were decided upon for evalua- tion, and are shown in Table 4. The solvent systems which provided the best conditions were 80:20 ethylene dichloride:n-butyl chloride and 70:30 methylene chloride:n-butyl chloride. The former, which contained less n-butyl chloride, was chosen for further study because it was more compatible with the sludge extract. It was also necessary to determine the amount of material that the gel could efficiently handle. Varying amounts of sludge extract was applied to 12 ------- TABLE 4. TEST SOLVENT SYSTEMS FOR SEPHADEX LH-20 FRACTIONATIONS Solvent System Comments 70:30 Methylene Chloride:Isopropanol 90:10 Ethylene Bichloride:Cyclopentane 80:20 Ethylene Bichloride:Acetone 80:20 Ethylene Bichloride:n-Butyl Chloride 80:20 Ethylene Dichloride:Benzene 70:30 Methylene Chloride:n-Butyl Chloride 70:30 Methylene Chloride:Cyclopentane 70:30 Methylene Chloride:Benzene 70:30 Methylene Chloride:Acetone Isopropanol caused precipitation. Gave poor separation. Gave poor separation. Designated for further studies. Benzene is restricted solvent. Designated for further study. Gave poor separation. Benzene is restricted solvent. Gave poor separation. ------- the Sephadex LH-20 columns, and it was found that approximately 5 mg of extractable material could be applied for each gram of dry Sephadex LH-20 without significantly overloading the column. After this process of optimizing the column run conditions, several standards containing various classes of priority pollutants were run on the column. It became evident that very polar compounds such as phenols did not elute from the column. BioBeads Chromatography BioBeads are porous styrene-divinylbenzene copolymers which do not have severe adsorption problems. The process of optimizing solvent systems was repeated, mainly concentrating on those solvent systems which were success- ful when used with Sephadex LH-20. Toluene was suggested by the manufacturer as a possible solvent for this application and was studied along with acetone, ethylene dichloride, methylene chloride, and 50:50 methylene chloride:acetone. Also studied were the different types of BioBeads differentiated by increasing pore sizes and hence increasing size exclusion limits. The grades studied were BioBeads S-X12, S-X8, S-X4 and S-X3, in order of increasing size exclusion limits. Toluene was found to be unsatisfactory as a solvent since it did not display good separating abilities. All of the other solvent systems dis- played good separation abilities. Acetone was rejected because it did not dissolve the sludge extractables as well as the other solvents. As the size exclusion limit of the BioBeads gel was increased its bed volume and separation ability increased. This indicated a tradeoff between good separation ability and short fractionation times. BioBeads S-X8 provided good fractionation capabilities and an acceptable analysis time and was chosen for further study- Elution profiles of whole sludge extracts on BioBeads S-X12, S-X8, and S-X4 are shown in Figure 2. The column flow parameter was found to be an important factor in optimization of this technique. The flow rate was optimized at approximately 4 to 8 ml/hour/cm2. Therefore, a 15 mm I.D. column, which has a cross- sectional area of 1.8 cm , would have an optimum flow rate of 7 to 14 ml/ hour. It was anticipated that certain classes of compounds, specifically fatty acids, triglycerides, and saturated hydrocarbons, would be present in large amounts in the sludge extracts and would subsequently cause problems in detecting low levels of the priority pollutants. It was therefore necessary to ascertain the efficiency of the BioBeads S-X8 system in separating these interfering compounds from the priority pollutants. Figure 3 represents three samples run on a 40 mm x 9 mm I.D. column packed with 10 grams of Bio- Beads S-X8 in 50:50 methylene chloride:acetone. The first sample (Figure 3(a)) was whole sludge extract, the second sample (Figure 3(b)) was com- posed of fatty acids, and the third sample (Figure 3(c)) contained tri- glycerides. It was ascertained by subsequent gas chromatographic analysis that the later eluting material, as indicated in Figure 3(a), was composed 14 ------- Elution Volume, ml Figure 2. Elution profiles of whole sludge extract on (a) BioBeads S-X12, (b) BioBeads S-X8, and (c) BioBeads S-X4 ------- 10 (a) 0 10 Triglycerldes Fatty Acids Saturated Hydrocarbons (b) Fatty Acids 10 bO- B (c) Trlglycerides 10 15 Elution Volume, rnl 20 25 Figure 3. Elution profiles of (a) whole sludge extract, (b) fatty acids, and (c) triglycerldes on BioBeads S-X8 ------- of saturated hydrocarbons. Capacity tests were also performed using BioBeads S-X8, and it was estimated that a maximum of 5 milligrams of sludge extractables per gram of BioBeads S-X8 could be applied without significantly overloading the column. The use of BioBeads S-X8 in the place of Sephadex LH-20 eliminated the adsorption problems encountered in the latter. When whole sludge was run through a BioBeads S-X8 column, virtually all of the material was recovered from the gel. This was also evident when phenol standards were run through the BioBeads S-X8 and no adsorbance problems were observed. Since material did not seem to adsorb to this column it was possible to reuse this column for more than one sample, thus saving the time necessary to pack new BioBeads S-X8 columns and also eliminating the necessity of purchasing large amounts of the gel. This also made the use of BioBeads S-X8 upward flow column packed in methylene chloride more desirable since the need for repeated re- packing of the column was eliminated. The size of the column was increased to increase its capacity to handle up to 1 gram of extractable material. The performance of the column in terms of efficiency and retention times of reference compounds was studied. Approximately 2500 theoretical plates were achieved for the elution of di-n-octyl phthalate. The capacity factors, K', for a number of reference compounds are given in Table 5. TABLE 5. CAPACITY FACTORS OF REFERENCE COMPOUNDS ELUTED WITH METHYLENE CHLORIDE FROM BIO-BEADS S-X8 Compound Capacity Factor r Di-n-octyl phthalate 0.40 Dimethyl phthalate 0.67 Phenylacetic acid 0.70 2,4-Dinitrophenol 0.76 Hexaethylbenzene 0.83 2-Nitrophenol 0.92 4-Nitrophenol 0.99 2,4-Dimethylphenol 1.01 Phenol 1.08 2-Chlorophenol 1.09 2,4-Dichlorophenol 1.11 Benzene 1.19 Dibenz(a,h)anthracene 1.19 Pyrene 1.31 Sulfur 1.80 It is of particular interest to note that the K' for sulfur is consid- erably higher than that of the other compounds. Because of this the GPC 17 ------- cleanup works very well for the removal of sulfur which would otherwise interfere with the GC-MS analysis. SILICA GEL CLEANUP It was necessary to include relatively large molecules in the fraction taken from the BioBeads cleanup of the neutral fraction in order to analyze for the larger phthalates. This necessitated a cleanup step to remove the relatively large amounts of long-chain hydrocarbons that were contained in that fraction. Silica gel chromatography was evaluated as a method to fractionate this extract on the basis of compound polarity. Standards con- taining a wide variety of compounds were run on silica gel, and the type of solvent system needed to elute each compound was noted. Nonpolar compound such as saturated hydrocarbons eluted with nonpolar solvent such as petroleum ether. Addition of increasing percentages of methylene chloride in petroleum ether eluted more polar molecules such as subsituted benzenes, naphthalenes and polynuclear aromatic hydrocarbons. It was necessary to go to 5% acetone in methylene chloride to elute polar neutral compounds such as isophorone, nitro compounds, and the phthalates. Very polar molecules remained on the silica gel. PACKED COLUMN GC-MS ANALYSIS In an effort to simplify the GC-MS analysis somewhat and utilize pre- viously developed EPA methods, the use of packed GC columns instead of a capillary column was studied very briefly. It was found that the sensitiv- ities achieved using packed columns, in terms of GC-MS peak areas, were generally poorer, by a factor of 5 to 10, than those achieved using capillary columns. Resolution, of course, was much lower with the packed columns. The results of a single comparison of the two techniques applied to the determination of components in spiked sludge are given in Table 6. The amounts found using a capillary column were somewhat higher than those found with packed columns. In some cases where components were found by the capillary technique none were found using packed columns. Additional studies are necessary for making a more valid comparison. However, since the confirmation of the identity of each component detected by a selected ion search is based upon its full mass range spectrum, the superior resolution of capillary column systems should give significantly fewer false negatives in a matrix as complex as sludge extracts. ANALYSIS OF PHENOLS Methylation of phenols by diazomethane is used to improve their gas chromatographic properties. Although the more acidic phenols, e.g. nitro- phenols and trichlorophenol, methylate rather completely, the less acidic phenols, e.g. dimethylphenol, chlorophenol, or phenol itself, are only partially derivatized if at all. One approach that was studied in an effort to achieve an improvement in the analysis of phenols, was the use of a packed GC column, 1% SP-1240DA, for the analysis of free phenols. The column gave good separation and good peak shape for all of the phenols however the sensitivity was lower than that 18 ------- obtained with a capillary column. The packed column data for phenols in Table 6 was obtained using 1% SP-1240DA. Despite the disadvantage of poorer sensitivity the packed column approach offers the advantage of eliminating the methylation step and therefore solves the problem of incomplete methylation of the less acidic phenols. Another approach to the derivatization problem is the use of a different derivatizing agent that might be suitable for all phenols. With this in mind we investigated briefly the preparation of pentafluorobenzyl derivatives by reaction with pentafluorobenzyl bromide (PFBB) in the presence of potassium carbonate and a crown ether. The method worked very well for the less acidic phenols but did not work for nitrophenols at low levels. Since the less acidic phenols can be determined satisfactorily as free phenols using a capillary column and the more acidic phenols are readily methylated by diazomethane this method was retained as the method of choice. DETERMINATION OF PESTICIDES The pesticides and PCBs included in the list of priority pollutants are similar to the semivolatile neutrals in terms of solubility, polarity, and size. Accordingly they would be expected to be found in the same fraction as the neutrals in the analysis scheme developed on this program. This means that the pesticides and PCBs could be determined at the same time that the neutrals are being determined with no additional effort other than the additional selected ion searches and calibration studies to establish retention times and response factors. In an effort to validate this concept a sample of digested sludge was spiked with aldrin, eudrin, heptachlor, p,p'-DDT, p,p'-DDE, p,p'-DDD, y-BHC, and Arochlor 1254 at a level of 10 yg/100 g wet weight and analyzed using the procedure in Appendix A. All of the spiked components were found in the GPC-2 neutral fraction. The recoveries were greater than 50% for each component. The results indicate that separate analysis schemes for pest- icides and PCBs are not necessary. ANALYSIS OF SPIKED AND NONSPIKED SAMPLES Samples of distilled water, raw municipal sludge, and digested municipal sludge were spiked with all 54 of the priority pollutants of concern and analyzed in triplicate. Similar analyses were performed for nonspiked samples in triplicate. The spiking level varied from 2.5 to 6 yg/lOOg depending upon the concentrations in standard solutions obtained from Supelco, Inc. The analytical procedures used was that described in detail in Appendix A. The recoveries obtained are given in Tables 7, 8,and 9. The recoveries from the water samples were very good for nearly all of the components except for dibenzo(a,h)anthracene and some of the phenols. This indicates that with a few exceptions the components are not being lost by the cleanup procedure in the absence of interferences. Most of the components are also recovered from raw or digested sludge, however, in many cases, a meaningful value for percent recovery could not be calculated be- cause of the very significant but highly variable amounts found in the 19 ------- TABLE 6. COMPARISON OF PACKED COLUMN AND CAPILLARY COLUMN GC ANALYSIS FOR DETERMINING THE RECOVERY OF PRIORITY POLLUTANTS FROM DIGESTED MUNICIPAL SLUDGE£ Amount Amount Recovered, pg/100 Added, Compound'3 yg/100 ml Bis-(2-chloroethyl) ether 1, 3-Dichlorobenzene 1,4-Dichlorobenzene 1 , 2-Dichlo rob enzene Bis-(2-chloroisopropyl) ether N-Nitrosodipropylamine Nitrobenzene Bis- ( 2- chloroe thoxy ) me thane 1, 2,4-Trlchlorobenzene Naphthalene Hexachlorobutadiene 2-Chloronaphthalene 2, 6-Dlnltro toluene Dimethyl phthalate Acenaphthylene Acenaphthene 2 , 4-Dini tro toluene Diethyl phthalate Fluorene 4-Chlorophenyl phenyl ether 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Packed Column0 NAe 4.6f NA NA NA NA 1.9 5.7 ND§ ND NA NA ND ND NA NA ND ND ml, Using Given GC Method Capillary Columnd NA 2.1 2.1 2.1 NA NA NA NA 6.7 12 1.1 3.4 NA NA ND 1.8 NA NA 7.7 ND ------- -TABLE 6. (Continued) Amount Amount Recovered, pg/100 ml, Using Given GC Method Compound" N-Nitrosodiphenylamine 4-Bromophenyl phenyl ether Hexachlorobenzene Phenanthrene Anthracene Di-n-butyl phthalate Fluoranthene Pyrene Butylbenzyl phthalate Chrysene Benzo (a) anthracene Bis (2-e thy Ihexyl) phthalate Di-n-octyl phthalate Benzo (b ) f luoranthene Benzo (k) f luoranthene Benzo (a) pyrene Benzo ( g , h , i) perylene Indeno(l, 2, 3-cd) pyrene Dibenzo (a , h) anthracene Acids 2-Chlprophenol Added, yg/100 ml 5.0 5.0 5.0 5.0 5.0 5.0 2.5 2.5 5.0 2.5 2.5 5.0 5.0 2.5 2.5 2.5 2.5 2.5 2.5 5.0 Packed Column0 NA 0.4 0.5 9.0h NA 1.1 1.5 NA ND ND NA NA ND ND ND ND ND ND 1.3 Capillary Columnd NA 1.9 2.2 15 15 NA 6.0 7.7 NA 6.1 6.1 NA NA 3.7 3.7 4.0 2.1 2.3 ND 1.2 ------- TABLE 6. (Continued) Amount Amount Recovered, ug/100 ml, Using Given GC Method Compound^ Phenol 2 , 4-Dimethylphenol 2,4-Dlchlorophenol 2,4, 6-Trichlorophenol 2-Nitrophenol 4-Chloromethyphenol 4-Nitrophenol 4 , 6-Dinitro-o-cresol Pentachlorophenol 2,4-Dinitrophenol Added, IJg/lOO ml 6.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Packed Column0 7.0 2.0 3.0 3.0 ND 3.0 ND ND 3.0 ND Capillary Columnd 11.0 1.6 6.1 5.1 ND 10 ND ND 3.3 ND The digested sludge used had a dry solids content of 2.5 g/100 ml and a total lipids content of 0.5 g/100 ml. b. The priority pollutant standards used were purchased from Supelco, Inc. c. A2mx2mmI.D. glass column packed with 3% SP-2250-DB on 100-120 mesh Supelcoport was used for neutrals and a 2 m x 2 mm I.D. glass column packed with 1% SP-1240-DA on 100-200 Supelcoport was used for free phenols. d. A 30 m x 0.2 mm I.D. glass capillary column coated with SE-30 was used for neutrals and methylated phenols. e. Not appropriate; only fraction GPC-2 and the acid fraction were analyzed using the packed column; this component does not appear in these fractions. f. Total for all three isomers. g. Not detected. h. Total for phenanthrene and anthracene. ------- TABLE 7. RECOVERY OF PRIORITY POLLUTANTS FROM WATER Co Compound Neutrals Bis-(2-chloroethyl) ether 1 , 3-Dichlorobenzene 1 ,4-Dichlorobenzene 1,2-Dichlorobenzene Bis-(2-chloroisopropyl) ether N-Nitrosodipropylamine Nitrobenzene Bis-(2-chloroethoxy) methane 1 , 2 ,4-Trichlorobenzene Naphthalene Hexachlorobutadiene 2-Chloronaphthalene 2,6-Dinitrotoluene Dimethyl phthalate Acenaphthylene Acenaphthene 2 ,4-Dinitrotoluene Diethyl phthalate Amount Added, Ug/100 ml 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 Amount Recovered, yg/100 ml , in Given Sample Unspiked 1 NDe ND ND ND ND ND ND ND ND 0.4 ND ND ND 0.2 ND ND ND 0.8 2 ND 'ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND 0.2 3 Avg. ND ND ND ND ND ND ND ND ND 0.3 0.2 ND ND ND ND 0.1 ND ND ND 0.6 0.5 1 3 3 3 6 5 6 4 3 5 6 2 6 5 9 7 7 5 7 .3 .9 .9 .0 .4 .8 .8 .9 .0 .7 .8 .6 .6 .0 .3 .4 .3 .3 Spiked 2 1.3 2.8 2.8 2.9 1.1 1.1 4.3 2.6 3.5 4.0 4.7 3.2 ND 5.6 5.5 4.7 ND 5.8 3 (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) Avg. 2.3 3.4 3.4 4.5 3.3 4.0 4.6 3.3 4.3 5.4 3.8 4.9 2.8 7.3 6.4 6.1 2.7 6.6 Average , Recovery, % 46 67 67 89 65 79 91 65 85 104 75 98 56 144 128 121 54 121 ------- TABLE 7. (Continued) NJ -O 2 Compound Acids c 2-Chlorophenol c Phenol c 2 ,4-Dimethylphenol c 2 , 4-Dichlorophenol d 2 ,4 ,6-Trichlorophenol d 2-Nitrophenol 4-Chloromethylphenol 4 -Nitrophenol 4 ,6-Dinitro-o-cresol Pentachlorophenol 2,4-Dinitrophenol Bases Benzidine 3,3' -Dichlorobenzidine a. The priority pollutant standards Amount Added, Amount Recovered, pg/100 Unspiked Ug/100 ml 1 5.0 6.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 0.6 0.6 used were b. (Avg. Recovered from Spiked Sample) - (Avg. c. Determined as the free phenol d. Determined as the methyl ester e. Not detected f. Neutral fraction lost ND 0.9 ND ND ND ND ND ND ND ND ND ND ND purchased Recovered 2 ND ND ND ND ND ND ND ND ND ND ND ND ND from from 3 Avg. ND ND 0.3 ND ND ND ND ND ND ND ND ND ND ND Supelco, Inc. Unspiked Sample) Amount Added ml, in Given Sample Spiked 1 2 3 Avg. 0.7 0.9 ND 0.5 2.7 ND ND 0.9 ND ND ND — 4.0 0.6 2.2 2.3 4.8 ND 4.5 3.1 ND ND ND 6.4 ND 8.6 5.0 ND ND ND — 5.5 ND ND 1.9 4.7 0.1 3.1 2.6 ND ND ND — 0.4 0.4 0.4 0.4 0.4 0.6 0.6 0.5 •v i nn A -LUU Average Recovery , % 10 10 — 46 62 — 100 — 38 52 — 67 83 ------- TABLE 7. (Continued) N3 Ol Compound Neutrals Fluorene 4-Chlorophenyl phenyl ether N-Nitrosodiphenylamine 4-Bromophenyl phenyl ether Hexachlorobenzene Phenanthrene Anthracene Dl-n-butyl phthalate Fluoranthene Pyrene Butylbenzyl phthalate Chrysene Benzo (a) anthracene Bis ( 2-ethylhexyl ) phthalate Di-n-octyl phthalate Benzo (b) f luoranthene Benzo (k) f luoranthene Benzo(a)pyrene Benzo (g,h,i)perylene Indeno(l,2,3-cd)pyrene Dibenzo (a, h) anthracene Amount Added, Amount Recovered, yg/100 ml, in Given Sample Unspiked yg/100 ml 1 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 2.5 2.5 5.0 2.5 2.5 5.0 5.0 2.5 2.5 2.5 2.5 2.5 2.5 ND ND ND ND ND 0.6 ND 3.7 0.3 0.4 27 ND ND 0.9 0.4 ND ND ND ND ND ND 2 ND ND ND ND ND ND ND 0.6 ND ND 0.3 ND ND 0.1 ND ND ND ND ND ND ND 3 Avg. ND ND ND ND ND ND 0.2 ND 0.9 1.7 ND 0.1 ND 0.1 1.7 0.7 ND ND 0.9 0.6 0.3 0.2 ND ND ND ND ND ND 1 7.4 4.5 2.0 5.1 5.7 5.6 7.6 10.9 2.1 2.5 7.4 2.5 2.5 11.2 8.3 2.5 2.5 2.2 0.6 2.0 ND Spiked 2 5.1 4.1 5.7 6.2 6.2 6.3 7.8 6.6 3.4 4.6 2.6 3.2 3.2 0.3 0.4 2.2 2.2 1.6 0.9 0.3 ND 3 (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) (f) Avg. 6.3 4.3 3.9 5.7 6.0 6.0 7.7 8.8 2.8 3.6 5.0 2.9 2.9 5.8 4.4 2.4 2.4 1.9 0.8 1.2 — Average Recovery , °/ 125 86 77 113 119 116 154 142 108 140 86 114 114 104 84 96 96 76 30 48 — ------- TABLE 8. RECOVERY OF PRIORITY POLLUTANTS FROM DIGESTED MUNICIPAL SLUDGE NJ Compound Neutrals Bis-(2-chloroethyl) ether 1 , 3-Dichlorobenzene 1 , 4-Dichlorobenzene 1 , 2-Dichlorobenzene Bis- (2-chloroisopropyl) ether N-Nitrosodipropylamine Nitrobenzene Bis- (2-chloroethoxy)methane 1,2, 4-Tr ichlorobenzene Naphthalene Hexachlorobutadiene 2-Chloronaphthalene 2 , 6-Dinitrotoluene Dimethyl phthalate Acenaphthylene Acenaphthene 2,4-Dinitrotoluene Diethyl phthalate Amount Added, yg/100 ml 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 Amount Recovered, ng/100 ml, Unspiked 1 NDf ND ND ND ND ND ND ND 0.3 5.1 ND ND ND ND ND 1.4 ND 37 2 ND 9.3 9.3 9.3 ND ND ND ND 2.8 32 ND ND ND ND ND 6.2 ND 0.4 3 ND 1.8 1.8 1.8 ND ND ND ND 0.4 5.8 ND ND ND 1.0 ND 1.7 ND ND Avg. 3.7 3.7 3.7 1.2 14 — - 0.3 2.4 12 1 ND 0.1 0.1 0.1 ND ND ND ND 1.0 3.7 0.5 0.7 ND 0.7 ND 0.6 ND 1.5 in Gfven Sample Spiked 2 ND 10 10 10 ND 1.5 ND ND 13 38 4.9 10.1 ND 5.2 ND 6.4 ND 5.0 3 ND 2.1 2.1 2.1 ND 5.4 ND ND 6.7 12 1.1 3.4 ND 14 ND 1.8 ND 16 Avg. 4.1 4.1 4.1 — 2.3 — — 6.9 18 2.2 4.7 — 6.7 — 2.9 — 7.5 Average Recovery, % NM8 NM NM — 46 — — NM NM 44 94 — 128 — NM — NM ------- TABLE 8. (Continued) Compound Neutrals Fluorene 4-Chlorophenyl phenyl ether N-Nitrosodiphenylamine 4-Bromophenyl phenyl ether Hexachlorobenzene Phenanthrene Anthracene Di-n-butyl phthalate Fluoranthene Pyrene Butylbenzyl phthalate Chrysene Benzo (a) anthracene Bis(2-ethylhexyl)phthalate Di-n-octyl phthalate Benzo (b)f luoranthene Benzo (k) f luoranthene Benzo (a) pyrene Benzo(g,h, i)perylene Indeno(l, 2, 3-cd) pyrene Dibenzo (a , h) anthracene Amount Added, yg/100 ml 5 5 5 5 5 5 5 5 2 2 5 2 2 5 5 2 2 2 2 2 2 .0 .0 .0 .0 .0 .0 .0 .0 .5 .5 .0 .5 .5 .0 .0 .5 .5 .5 .5 .5 .5 Amount Recovered, pg/100 ml, in Given Sample Unspiked 1 1.9 ND ND ND ND 8.1 8.1 7.4 3.8 4.8 150 3.2 3.2 690 190 0.7 0.7 ND ND ND ND 2 6.6, ND ND ND ND 35 35 4.0 16 24 33 15.0 15.0 13 9.7 4.9 4.9 6.4 3.2 3.9 ND 3 ND ND ND ND ND 6.3 6.3 2.5 3.9 5.1 60 4-2 4.2 12 8.1 1.9 1.9 2.4 0.8 1.1 ND Avg. 2.8 — — — — 16 16 27 7.9 12 81 7.5 7.5 240 93 2.5 2.5 2.9 1.3 1.7 — 1 1.0 4.0 ND 0.7 ND 7.7 7.7 13.1 3.4 4.1 47 3.6 3.6 150 64 1.0 1.0 1.0 1.7 2.2 ND Spiked 2 16.0 ND ND 4.3 3.8 39 39 9.7 18 24 64 14 14 21 9 4.3 4.3 7.2 0.8 1.6 ND 3 7.7 ND ND 1.9 2.2 15 15 32 6.0 7.7 400 6.1 6.1 100 66 3.7 3.7 4.0 2.1 2.3 ND Avg. 8.5 1.3 — 2.3 2.0 21 21 18 9.1 12 170 7.9 7.9 90 46 3.0 3.0 4.1 1.5 2.0 — Average Recovery, NM 26 — 46 40 NM NM NM NM NM NM NM NM NM NM NM NM NM NM NM — ------- TABLE 8. (Continued) Compound Amount Added, pg/100 ml Amount Recovered, pg/100 ml, in Given Sample Unspiked Spiked Avg. Avg. Average Recovery, CO Acids 2-Chlorophenol Phenold 2,4-Dimethylphenol 2,4-Dichlorophenol 2,4,6-Trichlorophenol 2-Nitrophenol d 4-Chloromethyphenol e 4-Nitrophenol e 4,6-Dinitro-o-cresol e Pentachlorophenol g 2,4-Dinitrophenol 5.0 6.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 ND ND ND ND ND ND NU ND ND ND HD 15 ND ND ND ND ND ND ND ND NTJ ND 0.4 ND ND ND SID ND ND ND ND ND 5.1 1.2 4.5 11.0 14 1.6 6.1 5.1 ND 10 ND ND 3.3 ND ND 5.1 3.2 ND ND ND ND 1.6 ND 3.5 0.8 1.5 5.6 4.9 ND 2.9 ND ND 2.6 ND 3.1 8.6 1.0 5.6 4.4 4.3 2.5 6.2 MM 20 112 86 50 Bases Benzidine 3,3'-Dichlorobenzidine 0.6 0.6 ND ND ND ND ND ND 0.4 0.3 0.4 0.2 1.2 0.6 0.7 0.4 117 67 The priority pollutant standards used were purchased from Supelco, Inc. The digested sludge used had a dry solids content of 2.5 g/100 ml and a total lipid content of 0.5 g/100 ml. (Avg. Recovered from Spiked Sample) - (Avg. Recovered from Unspiked Sample) Amount Added x 100 Determined as the free phenol Determined as the methyl ether Not detected Not meaningful because of large amounts and/or wide variations in amounts found in unspiked samples as well as in spiked samples. ------- TABLE 9. RECOVERY OF PRIORITY POLLUTANTS FROM RAW SLUDGE Compound Neutrals Bis- (2-chloroethyl) ether 1, 3-Dichlorobenzene 1 , 4-Dichlorobenzene 1, 2-Dichlorobenzene Bis-(2-chloroisopropyl) ether N-Nitrosodipropylamine Nitrobenzene Bis-(2-chloroethoxy)methane 1,2, 4-Trichlorobenzene Naphthalene Hexachlorobutadiene 2-Chloronaphthalene 2 , 6-Dinitrotoluene Dimethyl phthalate Acenaphthylene Acenaphthene 2,4-Dinitrotoluene Diethyl phthalate Fluorene Amount Added, yg/100 ml 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 Amount Recovered, pg/100 ml, in Given Sample 1 NDf ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND ND 0.7 5.0 Unspiked 2 ND 55 55 55 ND ND ND ND ND 65 ND ND ND 0.6 ND 21 ND 1.1 30 3 ND 15 15 15 ND ND ND ND 0.4 30 ND ND ND 0.2 ND 5.9 ND 4.5 22 Avg. 33 33 33 — — — — 0.1 32 — — — 0.3 — 9.0 — 2.1 17 1 6.1 0.2 0.2 0.2 ND 2.3 ND 7.2 2.0 7.5 1.0 ND ND 6.1 ND 4.0 ND 3.5 8.0 Spiked 2 6.1 25 25 25 ND 6.7 ND 7.3 7.5 35 1.8 ND ND 5.9 OT 26 ND 6.9 19 3 0.2 20 20 20 ND 6.2 ND 6.3 8.6 46 2.6 1.0 ND 6.0 ND 9.1 ND 7.2 27 Avg. 4.1 15 15 15 — 5.1 — 6.9 6.0 29 1.8 0.3 — 6.0 — 13 — 5.9 18 Average c Recovery, % 82 NM8 NM NM NM 102 — 138 118 NM 36 6 — 114 — NM — 76 NM ------- TABLE 9. (Continued) UJ O Compound Neutrals 4-Chlorophenyl phenyl ether N-Nitrosodiphenylamine 4-Bromophenyl phenyl ether Hexachlorobenzene Phenanthrene Anthracene Di-n-butyl phthalate Fluoranthene Pyrene Butylbenzyl phthalate Chrysene Benzo (a) anthracene Bis(2-ethylhexyl)phthalate Dl-n-octyl phthalate Benzo (b) f luoranthene Benzo (k) f luoranthene Benzo (a) pyrene Benzo (g,h,i)perylene Ind eno(l, 2, 3-cd) pyrene Dibenzo (a , h) anthracene Amount Added, g/100 ml 5 5 5 5 5 5 5 2 2 5 2 2 5 5 2 2 2 2 2 2 .0 .0 .0 .0 .0 .0 .0 .5 .5 .0 .5 .5 .0 .0 .5 .5 .5 .5 .5 .5 Amount Recovered, g/100 ml, in Given Sample Unspiked 1 ND ND ND ND 39 39 13 25 19 280 7.6 7.6 140 78 3.3 3.3 4.3 1.3 2.7 ND 2 ND ND ND ND 27 27 53 34 35 180 22 22 44 48 5.7 5.7 5.9 4.8 5.5 ND 3 ND ND ND ND 50 50 22 8.9 8.9 40 7.5 7.5 29 26 2.3 2.3 2.4 ND ND ND Avg. — — 39 39 29 23 21 170 12 12 71 51 3.8 3.8 4.2 2.0 2.7 — 1 1.2 2.4 3.1 2.5 34 34 64 11 12 450 8.6 8.6 100 19 3.5 3.5 5.2 ND ND ND Spiked 2 3.3 5.0 2.4 1.4 38 38 55 26 26 180 25 25 45 34 12 12 7.6 2.2 3.3 ND 3 3.2 3.3 2.4 2.4 68 68 14 14 13 45 9.1 9.1 44 30 4.5 4.5 5.9 2.5 3.3 ND Avg. 2.6 3.6 2.6 2.1 47 47 44 17 17 225 14 14 63 28 6.7 6.7 6.2 1.6 2.2 — Average Recovery, % 54 72 52 42 NM NM NM NM NM NM NM NM NM NM 116 116 80 NM NM — ------- TABLE 9. (Continued) Amount Added Compound pg/100 ml Acids 2-Chlorophenol Phenold 2 , 4-Dimethylphenol 2 , 4-Dichlorophenol 2,4, 6-Trichlorophenol 2-Nitrophenole 4-Chloromethy] Dhenol 4-Nitropnenole 4, 6-Dinitro-o-cresol Pentachlorophenol 2, 4-Dinitrophenole Bases Benzidine 3, 3-Dichlorobenzidine 5.0 6.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 1.2 1.2 a. The priority pollutant standards used b. The raw sludge used had a dry 1.4 Mg/100 ml. solids c. (Avg. Recovered from Spiked Sample) - Amount Recovered, pg/100 ml, in Unspiked 1 ND 14 ND ND ND ND ND ND ND ND ND ND ND 2 ND ND ND ND ND ND ND ND ND ND ND ND ND were purchased content of 4.4 3 Avg. ND ND 5 ND ND ND ND ND ND ND ND ND ND ND from Supelco, yg/100 ml and a (Avg. Recovered from Unspiked Amount Added d. Determined as the free phenol e. Determined as the methyl ether f . Not detected 1 ND 16 ND 1.4 0.2 ND 2.9 ND ND 2.6 ND 0.8 1.2 Inc. Given Sample Spiked 2 ND ND ND ND ND ND ND ND ND ND ND 0.8 1.2 total lipid Sample) v i r\r\ x 1UU 3 Avg. ND 14 10 WD 3.9 1.8 2.0 0.7 ND ND 1.0 ND ND 6.7 3.1 ND 0.8 0.8 1.6 1.3 content of Average Recovery, % — NM — 36 14 — 20 — — 62 — 100 108 Not meaningful because of large amounts and/or wide variations in amounts found in unspiked samples as well as in spiked samples. ------- unspiked samples. There was a noticeable lack of success in recovering some of the more polar neutrals and the nitrophenols. The poor recoveries could have been caused by various factors including degradation during the 24-hour period of equilibration with sludge, poor extraction from the sludge matrix, loss to the aqueous phase during caustic extraction steps, and alteration of separation patterns caused by large amounts of fatty acids. These are discussed under Recommendations. 32 ------- APPENDIX S100 METHOD FOR SEMIVOLATILE ORGANIC COMPONENTS 110 Scope and Application 111 This method covers the determination of 54 semi-volatile organic priority pollutants. A complete list of these compounds is given in Table 111. 112 The method is applicable to the measurement of these compounds in raw and digested municipal sludge. 113 The method is capable in most cases of detecting 2 pg of a priority pollutant per 100 ml of wet sludge (0.5 yg/g dry weight basis for sludge containing 4% solids). 120 Summary 121 This method offers separate procedures for the analysis of the acidic, neutral, and basic components. The procedure involves the use of repetitive solvent extraction to efficiently recover components from the sludge matrix. Gel permeation chromatography, silica-gel chromatography, and acid-base extractions are used as cleanup procedures to eliminate interferences. The acidic (phenolic) and neutral components are determined by GC-MS analysis using high-resolution glass capillary columns and selected ion searches. The bases, benzidine and 3,3-dichlorobenzidine, are determined by HPLC analysis using an electrochemical detector. The overall analysis scheme is shown in Figure 121. 122 This method is recommended for use only by analysts experienced in liquid chromatography, glass capillary column GC-MS analysis, and trace organic analysis of environmental samples, or under the close supervision of such qualified persons. 130 Apparatus and Reagents 131 For sample extraction, Section 150: 131.1 Tekmar tissuemizer 131.2 Solvents, distilled-in-glass grade: a. Methylene chloride b. Chloroform preserved with ethanol 33 ------- TABLE 111. EPA SEMIVOLATILE ORGANIC PRIORITY POLLUTANTS 2. 3. 4. 5. 6. 7. 8. Polvcyclic Aromatic Hydrocarbon 1. 2. 3. 4. 1. 2. Acenaphthene Acenaphthylene Anthracene Benzo(a)anthracene Benzo(b)fluoranthene Benzo(k)fluoranthene Benzo(g,h,i)perylene 3enzo(a)pyrene 9. Chrysene 10. Dibenzo(a,g)anthracene 11. Fluoranthene 12. Fluorene 13. Indeno(l,2,3-cd)pyrene 14. Naphthalene 15. Phenanthrene 16. Pyrene Phthalates 1. Bis(2-ethylhexyl) phthalate 2. Butylbenzyl phthalate 3. Diethyl phthalate 4. Dimethyl phthalate 5. Di-n-butyl phthalate 6. Di-n-octyl phthalate Chlorinated Hydrocarbons 2-Chloronaphthalene 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene 5. 6. 7. 8. Chloroalkvl Ethers Hexachlorob enzene 1,2,4-Trichlorobenzene Hexachlorobutadiene Hexachlorocyclopentad iene 3is-(2-chloroethyl) ether Bis-(2-chloroethoxy) methane 3. Bis-(2-chloroisopropyl) ether Nitrosamines 1. N-Nitrosodiethylamine 2. N-Nitrosodiphenylamine Miscellaneous Neutrals 1. 4-Bromophenyl phenyl ether 2. 4-Chlorophenyl phenyl ether 3, 2,4-Dinitrotoluene 1. 4-Chloro-3-methylphenol 2. 2-Chlorophenol 3. 2,4-Dichlorophenol 4. 2,4-Diaethylphenol 5. 4,6-Dinitro-2-methylphenol 6. 2,4-Dinitrophenol Benzidine Acids 4. 2,6-Dinitrotoluene 5. Isophorone 6. Nitrobenzene 7. 2-Nitrophenol 8. 4-Nitrophenol 9 - Pentachlorophenol 10. Phenol 11. 2,4,6-Trichlorophenol Bases 3,3'-Dichlorobenzidine 34 ------- SLUDGE OJ 100 g Wet Weight Acidify With KHSO. I * Extract With CII2C12 Cleanup Using Bio-Beads S-X8 Extract With 0.2 N NaOH I Acidify Aqueous Phase With 6 _N HC1 Extract With CII2C12 Methylate Using CILN,, Analyze by GC-MS PHENOLS 100 g Wet Weight Acidify With KHSO Extract With CII Cl™ Wash With 0.1 N NaOH r Fractionate Using Bio-Beads S-X8 Collect Two Fractions, GPC-1 and CPC-2 i Cleanup GPC-1 Using Activated Silica Gel i Combine GPC-2 and Cleaned up GPC-1 i Analyze by GC-MS NEUTRALS 10 g Wet Weight Dilute with 0.1 M Phosphate Buffer, pll? Extract With CIIC1 Preserved With Ethanol Extract With 2 N H2SO/( Neutralize Aqueous Extract to pll 6-7 Using 1 M Na P0/ Extract With C1IC1, Add Methanol to CI1C1 Extract and Concentrate Dilute WJth 0.1 M Acetate Buffer, pll 4.7 Analyze by 1IPLC Using Electrochemical Detector BENZTD1NES Figure 121. Scheme for determination of semi volatile priority pollutants in sludge. ------- c. Methanol 131.3 Glassware a. Centrifuge tubes - 50 ml and 200 ml, with Teflon- lined screw caps b. Round-bottom flasks - 500 ml and 100 ml, with 24/40 joints c. Vortex evaporator tubes - 15 ml d. Separatory funnels - 125 ml with Teflon stopcocks 131.4 Rotating evaporator 131.5 Vortex evaporator 131.6 Reagents a. Magnesium sulfate, anhydrous - conditioned at 450°C b. Potassium bisulfate, anhydrous - conditioned at 450°C c. Phosphate buffer - 0.1 M, pH 7 131.7 Syringe - 50 ml with 8-inch 15-gauge square-tipped needle 131.8 Microbalance 131.9 Aluminum foil pans - 25 mm 132 For removal of interferences, Section 160. 132.1 Reagents a. Magnesium sulfate, anhydrous - conditioned at 450°C b. Sodium hydroxide - 0.1 N in 10% NaCl c. Sodium hydroxide - 20% d. Hydrochloric acid - 6 IS e. Trisodium phosphate - 0.4 M f. Sulfuric acid - 2 Jfl g. Diazald h. Acetate buffer - 0.1 M, pH 4.7 132.2 Glassware a. Separatory funnels - 60 ml, 125 ml, and 500 ml with Teflon stopcocks b. Micro diazomethane generating apparatus - obtained from Paxton Woods Glass Shop, 7500 Brill Road, Cincinnati, Ohio c. Round-bottom flasks - 100 ml and 500 ml d. Vortex evaporator tubes - 15 ml graduated, screw cap, conical centrifuge tubes e. Centrifuge tubes - 50 ml and 200 ml, screw cap f. Chromatography column - 400 mm x 9 mm I.D. Lab-Crest column with 100-ml reservoir, scintered glass frit, Teflon stopcock, and Solv-Seal joints 132.3 Solvents, distilled-in-glass grade a. Methylene chloride b. Petroleum ether, b.p. 30-60°C c. Acetone d. Hexane e. Ethylene dichloride f. Chloroform preserved with ethanol 132.4 Silica gel - 100-200 mesh Davison grade 923, activated for 16 hours at 150°C 36 ------- 132.5 Standard solutions a. GPC calibration solution for neutrals - methylene chloride containing 1 mg each of di-n-tridecyl phthalate, di-n-octyl phthalate, 4-chlorophenyl phenyl ether, dimethyl phthalate, pyrene, and sulfur per ml b. GPC calibraton solution for acids - methylene chloride containing 1 mg each of 4-phenylbutyric acid, 2,4- dinitrophenol, 2,4-dichlorophenol, and sulfur per ml c. DDA internal standard solution - 10 mg of deca- deuteroanthracene in 100 ml of heptane 132.6 Rotating evaporator 132.7 Vortex evaporator 132.8 Gel-permeation chromatography system* a. Chromatographic column - 1200 mm x 25 mm I.D. glass b. Bio-Beads S-X8 - 200 g per column c. Pump - capable of constant flow of 0.1 to 5 ml/min at up to 100 psi d. Injector - with 5 ml loop e. Ultra-violet detector - 254 nm f. Strip-chart recorder 132.9 Centrifuge capable of handling 50-ml tubes 133 For quantitation, Section 160: 133.1 GC-MS system a. Capable of scanning from 50 to 450 a.m.u. every 2 seconds b. Capable of producing a recognizable mass spectrum at unit resolution from 10 ng of methyl stearate when the sample is introduced through the GC inlet c. Interfaced with a gas chromatograph equipped with an injector system designed for splitless injection glass capillary column work. All sections of the transfer lines must be glass or glass-lined and deactivated with Carbowax 20M d. Interfaced with a computer data system having a selected ion search program, i.e., a program capable of searching a full mass range total ion chromatogram for selected ions after the run is completed** e. Glass capillary column - 30mx0.2mmI.D. coated with SE-30 133.2 HPLC System a. Pump - capable of constant flow of 0.1 to 5 ml/min at up to 5000 psi *For the processing of large numbers of samples a GPC Auto Prep 1001, avail- able from Analytical Biochemistry Laboratories, Inc., or equivalent may be used with an operations procedure that will give performance equal to that described herein. **The system should have capabilities which at least meet the requirements of the EMSL guidelines contianed in "Sampling and Analysis Procedures for Screening of Industrial Effluents for Priority Pollutants", April, 1977. 37 ------- b. High-pressure injector - with 50 yl loop c. Chromatographic column - 4.6 mm I.D. x 25 cm stainless steel, packed with Lichrosorb RP-2, 5 micron particle diameter d. Electrochemical detector - equipped with a thin layer glassy carbon electrode e. Strip-chart recorder - 1 to 10 volts full scale f. Mobile phase - 50:50 acetonitrile: 0.1 M acetate buffer, pH 4.7 133.3 Syringes - 10 yl and 100 yl 133.4 Standard solutions - 0.2 mg/ml of neutrals, 0.5 mg/ml of phenols, and 0.1 mg/ml of benzidines in methanol. 140 Sampling and Preservation 141 Samples should be collected in 2000-ml wide-mouth glass containers with clean Teflon-lined or foil-lined caps. The containers should be heated in an oven at 450-500°C overnight to remove any traces' or organic contamination before use. The containers should be filled no more than two-thirds full with sample to minimize breakage during freezing. 142 Samples should be refrigerated at 4°C immediately after collection and extracted within 24 hours. If extraction within 24 hours is not possible the samples should be frozen. Samples may be stored for up to 30 days at -20°C or indefinitely at -75°C. In order to prevent breakage during storage it is essential that the container not be permitted to be slightly warmed and recooled. 150 Sample Extraction 151 Three separate samples are extracted, one each for neutral, acidic, and basic fractions. 152 Neutral fraction 152.1 Place 100 g of homogeneous sludge into a 200-ml centrifuge tube and acidify with 5 g of KHS04. 152.2 Add 100 ml methylene chloride to the centrifuge tube and homogenize for one minute with a tissuemizer. As a safety precaution in case of breakage place the glass tubes in the metal holders of the centrifuge prior to homogenization. 152.3 Cap the centrifuge.-tubes tightly with Teflon-lined screw caps and centrifuge to achieve good phase separation. Remove the methylene chloride layer with a 50-ml syringe and transfer to a 500-ml round-bottom flask. 152.4 Repeat extraction procedure two more times and combine the methylene chloride layers. 152.5 Concentrate to 60-80 ml on a rotating evaporator at 35°C. 38 ------- 153 Acid fraction 153.1 Extract 100 g of homogenized sludge following the procedure of 152.1 to 152.4 and dry the combined extracts by shaking with 2 g of MgS04. 153.2 Decant the extract into a 500-ml round-bottom flask and concentrate to 50 ml on a rotating evaporator at 35°C. Transfer concentrate to a 100-ml round-bottom flask and concentrate to 8-10 ml. Transfer to a 15-ml vortex evaporator tube and make up to 10 ml with methylene chloride. Mix thoroughly. Obtain a residue weight of 100 yl of the 10-ml concentrate and calculate the total amount of material in the sample. The residue weight is determined by placing the 100 yl on a tared aluminum foil pan, allowing the solvent to evaporate, and reweighing the pan using a microbalance. Concentrate the extract further as necessary on a vortex evaporator at 25°C to adjust the final total volume to 1.0 ml for every 200 mg of material in the sample. Centrifuge the concentrate to remove traces of particulate material. 154 Basic fraction 154.1 Place 10 g of homogenized sludge in a 50-ml centrifuge tube and dilute with 20 ml 0.1 M phosphate buffer (pH 7). Add 10 ml of chloroform and homogenize the mixture for one minute using a tissuemizer. Centrifuge to achieve a good phase separation and remove the chloroform layer using a 50-ml syringe. 154.2 Repeat the above extraction two more times using 10 ml of chloroform each time and combine the chloroform layers. 160 Removal of Interferences 161 The cleanup procedures described in this section are designed to remove the major interfering classes of compounds found in sludge extracts, namely triglycerides, fatty acids, and long-chain hydrocarbons. 162 Neutral fraction - Base extraction is used to remove phenols and fatty acids. Gel permeation chromatography is used to remove triglycerides and to obtain an intermediate-sized molecule fraction containing the higher alkyl phthalates and a small-molecule fraction containing the remaining neutral compounds of interest. Silica gel chromatography is used to remove saturated hydrocarbons from the higher alkyl phthalates. 162.1 Transfer the extract from Section 152.5 to a 1000-ml separatory funnel and add 200 ml of petroleum ether. Extract three times with 400-ml portions of 0.1 N^ NaOH in 10% NaCl followed by two washes with 200-ml portions of 10% NaCl and discard the aqueous layers. If an emulsion forms 39 ------- at the solvent interface, collect the emulsion in a centrifuge tube and centrifuge to separate the layers. 162.2 Dry the final organic layer by shaking with 2 g of MgSCty. 162.3 Concentrate to 200 mg/ml as described in Section 153.2. Centrifuge the concentrate to remove any traces of particulate material. 162.4 Prepare a 1200 mm x 25 mm I.D. gel permeation chromatography (GPC) column by slurry packing using 200 g of Bio Beads S-X8 that have been swelled in methylene chloride for at least 4 hours. Prior to initial use, rinse the column with methylene chloride at 1 ml/min for 16 hours to remove any traces of contaminants. Calibrate the system by injecting 5 ml of the GPC calibration solution for neutrals (132.5-a), eluting with methylene chloride at 2 ml/min for at least 3 hours and observing the resultant UV detector trace. The column may be used indefinitely as long as no darkening or pressure increases occur and a column efficiency of at least 1200 theoretical plates is acheived. The pressure should not be permitted to exceed 50 psi. Recalibrate the system daily. 162.5 Inject up to 5 ml of the neutral concentrate (from 162.3) onto the GPC column and elute with methylene chloride at 2 ml/min for at least 3 hours. Discard the first fraction that elutes up to a retention time represented by the minimum between the di-n-tridecyl phthalate peak and the di-n-octyl phthalate peak in the calibration run. Collect as Fraction GPC-1 the next fraction eluting up to a re- tention time represented by the minimum between the dimethyl phthalate peak and the 4-chlorophenyl phenyl ether peak in the calibration run. Collect as Fraction GPC-2 the remaining eluate that elutes up to a retention time represented by the minimum between the pyrene peak and the sulfur peak in the calibration run. 162.6 Apply the above GPC separation to any remaining neutral concentrate using only up to 5 ml at a time. Combine the fractions to give one "Fraction GPC-1" and one "Fraction GPC-2". 162.7 Prepare a 400 mm x 9 mm I.D. silica gel chromatography column by slurry packing using 20 g of activated silica gel suspended in 25% acetone in methylene chloride. Wash the column, using gravity flow, with 50 ml of 25% acetone in methylene chloride to remove any traces of impurities and then wash it with 50 ml of petroleum ether to remove the polar solvent. Care should be taken to avoid any bubbles of air or solvent vapor in the column. Solvent flow should be continued only until the solvent level is within 1 mm of the top of the silica gel. 162.8 Concentrate Fraction GPC-1 to 2 ml using the procedures described in Section 153.2 and add 2 ml of petroleum ether. 162.9 Apply the Fraction GPC-1 concentrate to the freshly prepared silica gel column and open the stopcock to permit flow until the liquid level is within 1 mm of the top of the 40 ------- silica gel. In a similar fashion rinse the sample onto the column completely with two 1-ml portions of 50% methylene chloride in petroleum ether. 162.10 Elute the column with 50 ml of 50% methylene chloride in petroleum ether to remove interfering nonpolar and slightly polar components. Discard this eluate. 162.11 Elute the column with 50 ml of 25% acetone in methylene chloride and collect the eluate as the phthalate fraction. The highly polar components remain on the silica gel which is then discarded. 162.12 Combine the phthalate fraction with Fraction GPC-2 and concentrate to 10 ml using the procedures described in Section 153.2. Add 0.1 ml of the DDA internal standard solution and 1.0 ml of ethylene chloride and concentrate to 0.2 ml using a vortex evaporator. This is the final neutral fraction used for GC-MS analysis. 163 Acid fraction - Gel permeation chromatography is used to remove triglycerides and fatty acids. Acid-base extraction is used to remove the remaining neutral and basic components. 163.1 Calibrate the GPC system described in Section 162.4 by injecting 5 ml of the GPC calibration solution for acids (132.5-b), eluting with methylene chloride at 2 ml/min for at least 3 hours and observing the resultant UV detector trace. Inject up to 5 ml of the acid concentrate (from 153.2) onto the GPC column. Elute with methylene chloride at 2 ml/min for at least 3 hours. Discard the first fraction that elutes up to a retention time represented by the minimum between the 4-phenylbutyric acid peak and the 2,4-dinitrophenol peak in the calibration run. Collect as the phenolic fraction the remaining eluate that elutes up to a retention time represented by the minimum between the 2,4-dichlorophenol peak and the sulfur peak in the calibration run. 163.2 Apply the above GPC separation to any remaining acid concentrate using only up to 5 ml at a time. Combine the phenolic fractions. 163.3 Concentrate the combined phenolic fractions to 2 ml using the procedures described in Section 153.2. Transfer the concentrate to a 50-ml centrifuge tube and add 20 ml of hexane. Extract two times with 20 ml of 0.1 N_ NaOH in 10% NaCl. Centrifuge if necessary to facilitate phase separation. Combine the aqueous layers in a 200-ml centrifuge tube and acidify with 1 ml of 6 _N HC1. 163.4 Extract the acidified aqueous phase two times with 20-ml portions of methylene chloride. Centrifuge, if necessary, to facilitate phase separation. Combine the organic layers and dry over MgS04. 163.5 Add 0.1 ml of the DDA internal standard solution and 10 ml of ethylene dichloride and concentrate to 3 ml using the procedures described in Section 153.2. 41 ------- 163.6 Methylate the phenols by bubbling diazomethane, generated from Diazald, into the solution until it turns yellow. Cap the sample and keep it at room temperature for 30 minutes. If the yellow color dissipates during this time add more diazomethane. 163.7 Concentrate the sample to 0.2 ml in a vortex evaporator at 30°C. This is the acid fraction for GC-MS analysis. 164 Basic fraction 164.1 Transfer the chloroform extract from'154.2 to a 50-ml centrifuge tube and extract twice with 10 ml 2 N^ H2SC-4 using a 50 ml syringe to withdraw the aqueous layer from the bottom. 164.2 Combine aqueous layers in a 50-ml beaker containing a magnetic stirring bar and neutralize by the dropwise addition with stirring of 1 ml of 0.4 M Na3?04 followed by the dropwise addition over at least a two-minute period of 20% NaOH to pH 6-7 (approximately 7 ml will be required). Do not allow the sample pH to ever exceed pH 8. 164.3 Transfer the neutralized aqueous extract to a 60-ml separatory funnel and extract twice with 10 ml portions of chloroform. Wash the combined chloroform extracts with 5 ml of distilled water. Add 5 ml of methanol to the chloroform extract and concentrate to 0.2 ml using a vortex evaporator at 25°C. 164.4 Dilute to 1 ml with 0.1 M acetate buffer (pH 4.7). This is the basic fraction used for the analysis of benzidines by HPLC. 170 Quantitation 171 The neutral and acidic (phenolic) components are quantitated by GC-MS analysis using an SE-30 glass capillary column. The basic components (benzidines) are quantitated by HPLC analysis using an electrochemical detector. 172 Neutral and acidic fractions 172.1 Inject 2 yl of sample into the GC-MS using the splitless mode with the injector at 270°C, column at 60°C, transfer "line at 280°C, and helium carrier gas flow at approximately 2 ml/min. Hold the column temperature at 60°C for 5 minutes, then temperature program at 4 degrees per minute to 270°C and hold at 270°C for 15 minutes. Scan m/e values of 40-450 at approximately 30 scans per minute. Start data acquisition four minutes after injection. 172.2 Locate the priority pollutant compounds in the GC-MS runs by selected ion searches (see 133.1-d) (SIS). In this method, the computer is instructed to search the full mass range mass spectra for several specified m/e values which are characteristic of the compound of interest. These 42 ------- TABLE 172.2. GC-MS DATA USED FOR DETERMINING SEHIVOLATILE PRIORITY POLLUTANTS Compound Approximate Retention Time, nin/^M.W. Ions Used For Quantitation, m/e (intensity) Bis-(2-chloroethyl) ether 1 , 3-Dichlorobenzene 1 , 4-Dichlorobenzene 1,2-Dichlorobenzene Bis-(2-chloroisopropyl) ether N-Nitrosodipropylamine Nitrobenzene Isophorone Bis- (2-chloroethoxy) me thane 1,2, 4-Trichlorobenzene Naphthalene Hexachlorobutadiene Eexachlorocyclopentadiene 2-Chloronaphthalene 2 , 6-Dinitro toluene Dimethyl phthalate Ac enaphthal ene Acenaphthene 2 , 4-Dinitro toluene Diethyl phthalate Fluor ene 4-Chlorophenyl phenyl ether N-Nitrosodiphenylamine -^) 4-Bromophenyl phenyl ether Hexachlorobenzene Phenanthrene Anthracene Di-n-butyl phthalate Fluoranthene Pyrene Butylbenzyl phthalate Chrysene Benzo (a) anthracene 3is(2-ethylhexyl) phthalate Di-n-octyl phthalate Benzo (b) fluoranthene Benzo (k) fluoranthene Eenzo (a) pyrene Benzo (g ,h , i) perylene Indeno(l ,2 ,3-cd) pyrene Dibenzo(a ,h) anthracene Neutrals 10.5 10.6 10.6 11.2 11.7 12.6 13.4 14.6 15.5 16.8 17.1 18.8 22.7 24.0 25.5 26.3 27.0 27.2 27.9 30.4 30.5 30.6 31.4 33.0 33.4 35.6 35.9 40.1 42.5 43.7 48.5 50.9 51.2 52.9 55.9 56.4 56.9 62.8 66. £ 68.3 72.5 142 146 146 146 170 130 123 138 180 180 128 258 270 162 182 194 152 154 182 222 166 204 198 248 282 178 178 278 202 202 298 228 228 390 390 252 252 252 276 276 278 93(100), 63(99), 146(100) , 148(65) , 146(100) , 148(65) , 146(100). 148(65) , 45(100), 77(19), 70(100), 130(30) 77(100), 123(50) 82(100), 138(15) 93(100), 95(32), 180(100), 182(97) 128(100) , 127(15) 225(100), 227(60) 237(100), 235(63), 162(100), 127(40) 165(100), 89(80) 163(100), 77(21) 152(100) , 151(23) 153(100) , 154(90) 165(100), 63(60) 149(100), 178(25) 166(100), 165(90) 204(100), 141(75) 169(100) , 168(72) 248(100), 250(95) 282(100) , 284(77) 178(100) , 176(17) 178(100) , 176(17) 149(100), 104(10) 202(100) , 101(25) 202(100) , 101(25) 149(100), 91(62) 228(100), 226(27) 228(100) 149(100), 167(38) 149(100) , 167(34) 252(100), 253(23) 252(100), 253(23) 252(100) , 253(23) 276(100) 276(100) 278(100) 95(31) 111(35) 111(35) 111(35) 79(12) 123(21) 272(12) 43 ------- TABLE 172.2. (Continued) Compound Approximate Retention Time, min£a) M.W. Ions Used for Quantitation, m/e (intensity) (c) 2-Chlorophenol(-c) Phenol 2,4-Dimethylphenol 2,4-Dichlorophenol 2,4,6-Trichlorophenol(Me) ophenol(Me)( } (d) 2-Nitrophenol(M< 4-Chloro-3-methylphenol 4-Nitrophenol(Me)(d) 4,6-Dinitro-o-cresol(Me) Pentachlorophenol(Me)(d) 2,4-Dinitrophenol(Me)(d) Decadeuteroanthracene (c) Phenols 11.0 11.7 16.9 18.1 22.6 22.9 23.3 25.8 33.8 34.9 35.5 Internal Standard 128 94 122 162 210 153 142 153 212 278 198 128(100), 94(100), 107(100), 162(100), 195(100), 77(100), 107(100), 107(100), 89(100), 237(100), 76(100), 130(33) 66(60), 121(97), 164(66) 197(95), 106(80), 142(69), 77(82), 165(61), 265(91), 151(69), 65(35) 122(85) 167(75) 92(65) 77(62) 153(12) 182(58) 280(70) 168(62) 35.9 188 188(100) a. b. c. d. GC conditions: 30 m x 0.2 mm I.D. glass capillary column coated with SE-30; hold the column temperature at 60°C for 5 minutes then program at 4 degree per minute to 270°C and hold at 270°C for 15 minutes. Decomposes upon injection in the GC to diphenylamine; therefore, it is detected as diphenylamine. Determined as the free phenol. Determined as the methyl ether. 44 ------- selected ions are given in Table 172.2. Whenever a peak is tentatively identified by SIS methods as a priority pollutant, its full mass spectrum and retention time should be studied manually for positive confirmation. The area counts for the selected ions of each identified priority pollutant and the DBA internal standard are then obtained by the computer. 172.3 Quantitate the identified priority pollutants using the following equation: PP 10 I X DDA X RF X W where X = concentration of the priority pollutant in the sludge in yg/g dry weight PP = area counts obtained for the priority pollutant DDA = area counts found for decadeuteroanthracene RF = response factor of the priority pollutant relative to that of DDA as determined by GC-MS analysis of standard solutions W = dry weight, g, of 100 g of wet sludge Response factors for the particular GC-MS system used should be determined at least weekly- 173 Basic fraction 173.1 Inject 50 yl of the final base extract into the sample loop of the HPLC system described in Section 133.2. Use a flow rate of 0.8 ml/min and operate the detector at 0.8 volts versus a standard calomel electrode. 173.2 Quantitate the benzidine and 3,3'-dichlorobenzidine on the basis of peak heights using the following equation: H _ sample 5. A H , X W std where X = concentration of the benzidine in the sludge in yg/g dry weight TT sample = peak height of the benzidine found in the sample H = peak height of the benzidine obtained from 50 yl of a standard solution containing 0.5 yg/ml of each of the two benzidines 45 ------- W = dry weight, g, of 100 g of wet sludge 180 Quality Assurance 181 Sample processing 181.1 Process blanks - In order to assess any contamination sources during sample extraction and cleanup, at least one process blank (distilled water) should be run concurrently with each set of 10 sludge samples. The resulting neutral and acidic fractions may be analyzed by GC alone instead of by GC-MS. 181.2 Spiked process blanks - In order to assess recovery efficiencies of the extraction and cleanup procedures used, in the absence of matrix effects, at least one spiked blank should be run concurrently with each set of 10 sludge samples. The spike should contain 10 yg of each of the priority pollutants of concern. The resulting neutral and acidic fractions may be analyzed by GC alone instead of by GC-MS. Recoveries of at least 25% for each component should be achieved. Occasionally in order to assess the lower sensitivity of the method a spike containing only 2 yg per 100 ml should be used. At the 2 yg level recoveries of at least 25% should not be expected for all compounds. 181.3 Spiked sludge - In order to assess overall recovery efficiencies, including matrix effects, and also assess the reproducibility of the method, triplicate samples of a representative sludge should be run with every 10 sludge samples. The sludge should be spiked with each of the priority pollutants of concern at a level of 10 yg per 100 ml. The spiked sludges should be equilbriated at 4°C for 1 hour prior to extraction. Recoveries of at least 10 percent for each component should be achieved. Occasionally in order to assess the lower sensitivity of the method a spike level of only 2 yg per 100 ml should be used. At the 2 yg level recoveries of at least 10% should not be expected for all compounds. 181.4 Replicate samples - In order to assess the reproducibility of the method, one of every 10 sludge samples should be run in triplicate. 182 GPC fractionation - The GPC system should be calibrated daily or after every 10 runs to determine retention times and column efficiency by injecting 5 ml of the GPC calibration solutions. The column efficiency or number of theoretical plates (N) is calculated from the retention time, t, and the peak width at half height, W]_/2, obtained for the di-n-octyl phthalate peak on the UV trace using the equation 46 ------- The column should not be used unless at least 1200 theoretical plates can be achieved. 183 GC-MS analysis - Strict performance standards need to be main- tained to ensure that the GC-MS system is providing adequate sensitivity and high quality chromatograms and mass spectra. 183.1 Capillary column performance - Prior to installing the glass capillary column in the GC-MS, evaluate the column in a GC system designed for all-glass capillary column work. With the helium carrier gas flow adjusted to 30-40 cm/sec, the split ratio adjusted to 10:1 and, column oven temperature set at 100°C, inject 2 yl of a column per- formance test mixture containing 25 ng/yl each of 2,6-dimethylphenol, 2,4-dimethylaniline, n-decyl alcohol, n-decyl aldehyde, n-tridecane, and n-tetradecane. a. The acidity of the column is measured as the ratio of the peak height of dimethylphenol to that of dimethylaniline. A value of 0.5 to 2.0 is considered acceptable. b. The polarity of the column is determined from the degree of tailing of the n-decyl alcohol peak. This is evaluated by drawing a perpendicular from the apex of the peak to the baseline and measuring, at one- tenth peak height, the width from the front of the peak to the perpendicular line and from the back of the peak to the perpendicular line. If the width at the back of the peak is greater than four times the width of the front of the peak, the column is too polar for sample analyses. Low polarity is particularly important for achieving satisfactory sensitivity in the analyses of polycyclic aromatic hydrocarbons and more polar compounds. c. The number of effective plates (Neff) is determined from the n-tetradecane peak using the equation: ? t Neff = 5.5' W 1/2 where tc = the corrected retention time of n- tetradecane, and ^1/2 = tne Peak width at half height. The number of effective plates of acceptable columns must be at least 50,000. Only columns which meet all of the above criteria are to be used for the GC-MS analyses. 47 ------- 183.2 Mass spectrometer tune up - Calibrate and tune the mass spectrometer each day before samples are analyzed. After tuning and calibration has been completed, admit decafluorotriphenylphosphine (DFTPP) into the mass spectrometer via the solids probe. Its spectrum should be comparable to that described by Eichelberger, et al. [Anal. Chem., ^16, 995 (1975)]. Retune and recalibrate the instrument if necessary. 183.3 Capillary column GC-MS performance - Evaluate the performance of the complete glass capillary column GC-MS system each day prior to its use for the analysis of neutral fractions. Using splitless injection techniques and the standard sample analysis conditions inject 2.0 yl of a heptane solution containing 20 ng each of 1-naphthylamine, 2-naphthol, 1-pentadecanol, DFTPP, 3-methylnonadecane, tridecylcyclohexane, n-eicosane, pyrene, n-heneicosane, and methyl stearate. The total ion chromatogram is used to assess the system performance. a. The acidity of the system is measured as the ratio of the peak areas of the naphthylamine and naphthol. It must be between 0.5 and 2.0 to be acceptable. b. The polarity of the system is measured by the peak height of 1-pentadecanol, pyrene, or methyl stearate relative to that of n-eicosane. In each case a value of at least 0.2 must be obtained. c. The sensitivity of the system is measured by the signal to noise ratio obtained for pyrene. It must be at least 20. d. The resolution of the system is assessed by the resolution achieved between tridecylcyclohexane and 3-methylnonadecane. The resolution should be sufficient to give a valley between the two peaks which is no more than 20% of the peak heights. e* The high/low mass spectral balance of the system is determined from the mass spectrum of DFTPP. The ratio of the intensities of the 442 ion and the 198 ion should be 0.4 to 0.7. This is a check on the earlier MS tuneup. 183.4 Response factors and retention times - Once each week or each time a substantal change in GC-MS performance is observed, the response factors and retention times for the . priority pollutants should be determined. This is accomplished by analyzing 2 yl of standard solutions containing 50 ng/yl of decadeuteroanthracene and each of the neutral and acidic priority pollutants. 184 HPLC analysis - With each set of samples analyzed, analyze a standard containing 0.5 yg/ml of each of the two benzidines. The retention times and peak heights are used for the detection and quantitation of the benzidines in the samples. 48 ------- TECHNICAL REPORT DATA (Please read Instructions on the reverse before completing) 1. REPORT NO. EPA-600/2-80-Q30 3. RECIPIENT'S ACCESSION-NO. 4. TITLE AND SUBTITLE Analytical Procedures For Determining Organic Priority Pollutants in Municipal Sludges 5. REPORT DATE March 1980 (Issuing Date) 6. PERFORMING ORGANIZATION CODE 7. AUTHOR(S) J. S. Warner, G. A. Jungclaus, T. M. Engel, R. M. Riggin, and C. C. Chuang 8. PERFORMING ORGANIZATION REPORT NO. 9. PERFORMING ORGANIZATION NAME AND ADDRESS Battelle Columbus Laboratories 505 King Avenue Columbus, Ohio 43201 10. PROGRAM ELEMENT NO. 1BC611 11. CONTRACT/GRANT NO. 68-03-2624 12. SPONSORING AGENCY NAME AND ADDRESS Municipal Environmental Research Laboratory—Cin.,OH Office of Research and Development U. S. Environmental Protection Agency Cincinnati, Ohio 45268 13. TYPE OF REPORT AND PERIOD COVERED Final 14. SPONSORING AGENCY CODE EPA/600/14 15. SUPPLEMENTARY NOTES Project Officer: Richard A. Dobbs (513) 684-7649 16. ABSTRACT An analytical procedure was developed for the determination of 54 semi- volatile organic priority pollutants in sludge at levels down to 0.01 yg/g wet weight. The procedure involved extraction with methylene chloride or chloroform, cleanup of groups of compounds having common properties, and in most cases analysis of the fractions by GC-MS using high-resolution glass capillary columns and selected ion searches. The final analyses involved the analysis of three separate fractions, namely benzidines, phenols, and neutrals. The benzidines were determined by HPLC analysis using an electrochemical detector instead of by GC-MS because GC-MS sensitivity for these compounds was too low. Quantitation in the GC-MS analyses involved the internal standard method applied to selected ion responses. Relative response factors obtained from the analysis of standard solutions were used as correction factors. 17. KEY WORDS AND DOCUMENT ANALYSIS DESCRIPTORS b.IDENTIFIERS/OPEN ENDED TERMS C. COSATI Field/Group Organic Compounds Activated Sludge Primary Sludge Chemical Analysis Mass Spectroscopy Gas Chromatography Priority Pollutants 07C 18. DISTRIBUTION STATEMENT Release to public 19. SECURITY CLASS (This Report) UNCLASSIFIED 21. NO. OF PAGES 55 20. SECURITY CLASS (Thispage) UNCLASSIFIED 22. PRICE EPA Form 2220-1 (9-73) 49 U S GOVERNMENT PRINTING OFFICE 1980-657-146/5639 ------- |