Analysis of Organic Pollutants in the Pharmaceutical Manufacturing Industry Using USEPA Method 1666

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1 Application Note Analysis of Organic Pollutants in the Pharmaceutical Manufacturing Industry Using USEPA Method 1666 Keywords Pharmaceutical PMI Purge and Trap USEPA Method 1666 Volatile Organic Compounds Introduction On September 21, 1998, the USEPA established effluent limitations, guidelines, and standards for conventional, toxic, and nonconventional pollutants found in wastewater discharged from the Pharmaceutical Manufacturing Industry (PMI). 1 The PMI dischargers are required to use the test methods promulgated by the new rule to monitor for regulated contaminants. 2 The new methods are numbered 1666, 1667, and Method 1666, Volatile Organic Compounds Specific to the Pharmaceutical Manufacturing Industry by Isotope Dilution GC/MS, is a purge-andtrap method using a bench top GC/MS and incorporating quantitation by isotope dilution for eight of the 20 targeted compounds. 3 All existing PMI facilities must be in compliance with the new rule by September This application note presents data using an OI Analytical Model 4560 Sample Concentrator optimized for the analysis of target compounds specific to the PMI by USEPA Method Several of the target analytes in Method 1666 are polar compounds that are soluble in water and require that the sample be heated during the purge cycle for acceptable recovery. The described hardware system and operating conditions for determining purgeable organic compounds in water are shown to produce exceptional method performance in terms of response factors (RFs), method detection limits (MDLs), recovery, and reproducibility, which all fall well within the guidelines specified by the method. Optimal Analytical Conditions The range of chemistries represented by the target compound list in Method 1666, along with matrix problems unique to the analysis of volatile organic pollutants in water, pose a considerable challenge. The target analyte list includes four alcohols (isopropyl alcohol, t-butyl alcohol, n-butyl alcohol, and n-amyl alcohol) and methyl formate, all of which are extremely polar and soluble in water at essentially all concentrations. There are also acetates, ketones, and ethers on the list, which present similar difficulties. The primary dilemma with this type of analysis is two-fold. First, how do you purge the water soluble target analytes from the sample matrix with recoveries that will meet method criteria? And second, how do you remove the water from the trap, while retaining the water soluble analytes, prior to transferring to the analytical column?

2 The first problem is solved by heating the sample matrix during the purge cycle. Method 1666 requires that the sample be heated to 45 C while purging. Temperatures above 45 C result in little additional improvement in analyte recovery, as shown in Table 1, and may result in decreased chromatographic resolution for some compounds, primarily the polar ones. The deterioration of chromatography at higher sparge temperatures is due to the fact that at higher temperatures more water is transferred to the trap along with the analytes. The additional water will occupy adsorptive sites in the trap normally occupied by the target compounds. This forces the target compounds to migrate further into the trap, negatively impacting the desorption/chromatographic profile. The Model 4560 Sample Concentrator uses an infrared lamp to heat aqueous samples directly, heating the samples more rapidly and reproducibly than is possible with just a heater jacket. Additionally, cold spots in the sample path must be eliminated to minimize condensation of water and polar analytes. With other instrument designs, the ambient temperature of the sparge mount acts as a cold spot, allowing water and target analytes to condense out of the sample gas stream before they ever reach the trap. This can result in inconsistent results and low recoveries. The Model 4560 uses a heated sparge mount, with the temperature controlled by an independent heater and thermocouple, thus eliminating the cold spot found in other instruments. The second problem, removal of water while retaining target compounds, necessitates an effective water management system. OI Analytical s purge-and-trap sample concentrator incorporates an advanced condensation trap called the Cyclone Water Management system, which is covered by three patents. The cyclone chamber forces the desorb gas into a tight, turbulent vortex and is capable of removing up to 99% of the water released from the trap. The Cyclone Water Management system is sufficient to retain water from samples purged up to 85 C. Under the operating conditions defined in Method 1666, this system removes all but about 0.25 mg of trapped water, compared to up to 11 mg water without water management. 4 All of the instrument operating conditions necessary for obtaining optimal method performance are detailed in Table 2. Total analytical cycle times for the method are 23 minutes for purge and trap and 24 minutes for GC/MS. A typical chromatogram obtained under the described conditions is shown in Figure 1. Method Performance Calibration Calibration data were acquired according to the procedures outlined in USEPA Method 1666 and using the quantitation ions suggested in the method. Average response factors and correlation coefficients were determined for 15 of the 20 target compounds over the calibration range of 5 ppb to 200 ppb. (Section of the method suggests a calibration range of 10 ppb to 200 ppb.) The four alcohols and methyl formate are highly water soluble, and they are present in the commercially prepared standard mixtures at two-and-a-half times the concentration of the other 15 target analytes. The calibration range for those five compounds was 12.5 ppb to 500 ppb. Quantitative analysis was done using an isotope dilution technique for all compounds for which a stable, isotopically labeled analog was available. For all other compounds, quantitative analysis was performed using the internal standard technique. All percent relative standard deviations (%RSDs) met the method acceptance criteria of <20%. In general, RFs for the water soluble polar compounds tended to be lower, and %RSDs were higher due to their higher solubility in water relative to the internal standards. Calibration statistics for all target compounds are listed in Table 3. Calibration curves for all polar and nonpolar compounds are shown in Figure 2.

3 Table 1. Average Compound Recoveries (n=3) From Purge and Trap Relative to Direct Injection Sample Temp 45 C 45 C 55 C 65 C 75 C (4-mm liner) (2-mm liner) (4-mm liner) (4-mm liner) (4-mm liner) # Compound Name % Relative %Relative %Relative %Relative %Relative Recovery Recovery Recovery Recovery Recovery Internal Standards 10 IS Bromochloromethane IS 1,4-Difluorobenzene IS Chlorobenzene-d Labeled Compounds 5 LSS, W t-butyl alcohol-d LSS n-hexane-d LSS Ethyl acetate- 13 C LSS Tetrahydrofuran-d LSS Cyclohexane-d LSS n-heptane-d LSS m-xylene-d LSS o-xylene-d Target Analytes 1 T,W Methyl formate T Trichlorofluoromethane T,W Isopropanol T n-pentane T,W t-butyl alcohol T n-hexane T Isopropylether T Ethyl acetate T Tetrahydrofuran T,W n-butyl alcohol T Isopropyl acetate T Cyclohexane T n-heptane T Methylisobutyl ketone T,W n-amyl alcohol T n-butyl acetate T m-xylene T p-xylene T n-amyl acetate T o-xylene # = Elution Order IS = Internal Standard LSS = Labeled Surrogate Standard T = Target Compound W=Water Soluble Compound (present in standard mixture are at 2Q/w times the concentration of other target analytes)

4 Table 2. Equipment Description and Optimum Instrument Operating Conditions Purge and Trap Model 4560 Purge-and-Trap Sample Concentrator Autosampler Model 4551A Vial Autosampler Trap #10 Trap (Tenax /Silica Gel/Carbon Molecular Sieve) Purge Time 11 minutes Purge Temperature 18 C (Set point 15 C) Desorb Time 2 minutes Desorb Temperature 180 C Bake Time 10 minutes Bake Temperature 190 C Infasparge Temperature 45 C Sample Inlet Temperature 45 C Trap Preheat ON, 50 C Water Management ON Valve Temperature 100 C Transfer Line Temperature 100 C Total Cycle Time 23 minutes Gas Chromatograph HP 6890 Plus GC with EPC Column J&W DB-VRX, 60 m, 0.25 I.D., 1.4-mm film thickness Carrier Gas He Mode Pulsed Split Inlet Temperature 200 C Pressure 16.2 psi Split ratio 14:1 Pulse pressure 23.0 psi Pulse time 1 minute Split flow 14.0 ml/min Total flow 17.5 ml/min Gas saver ON Saver flow 15.0 ml/min Saver time 3.0 min Oven Program 35 C for 4 minutes 6 C/minute to 155 C 50 C/minute to 220 C hold for 2 minutes Mass Spectrometer HP 5973 with Turbo Pump Option Mode Scan amu Scans/Second 3.25 Solvent Delay 4 minutes Transfer Line Temp 240 C Source Temperature 230 C Quad Temperature 150 C

5 1.8e+07 TIC: [BSB1]200PB030.D e+07 27,28 1.4e e e , , , Methyl formate 2 Trichlorofluoromethane 3 Isopropanol 4 n-pentane 5 t-butyl alcohol-d 10 6 t-butyl alcohol 7 n-hexane-d 14 8 n-hexane 9 Diisopropyl ether 10 Bromochloromethane (IS) 11 Ethyl acetate- 13 C 2 12 Ethyl acetate 13 Tetrahydrofuran-d 8 14 Tetrahydrofuran 15 n-butyl alcohol 16 Cyclohexane-d Isopropyl acetate 18 Cyclohexane 19 1,4-Difluorobenzene (IS) 20 n-heptane-d n-heptane 22 Methylisobutyl ketone 23 n-amyl alcohol 24 n-butyl acetate 25 Chlorobenzene-d 5 (IS) 26 p-xylene-d m-xylene 28 p-xylene 29 o-xylene-d Amyl acetate 31 o-xylene Figure 1. Chromatogram of USEPA Method 1666 Target Compound List

6 Table 3. Calibration Statistics, Method Detection Limits (MDLs), and Minimum Levels (MLs) for all Target Compounds Compound Name IS or Quantitation RF %RSD R 2 MDL ML ID Standard (ppb) (ppb) Labeled Compounds t-butyl alcohol-d 10 IS Bromochloromethane n-hexane-d 14 IS Bromochloromethane Ethyl acetate- 13 C 2 IS Bromochloromethane Tetrahydrofuran-d 8 IS Bromochloromethane Cyclohexane-d 12 IS 1,4-Difluorobenzene n-heptane-d 16 IS 1,4-Difluorobenzene m-xylene-d 10 IS Chlorobenzene-d o-xylene-d 10 IS Chlorobenzene-d Target Analytes Methyl formate IS Bromochloromethane Trichlorofluoromethane IS Bromochloromethane Isopropanol IS Bromochloromethane n-pentane IS Bromochloromethane t-butyl alcohol ID t-butyl alcohol-d n-hexane ID n-hexane-d Isopropyl ether IS Bromochloromethane Ethyl acetate ID Ethyl acetate- 13 C Tetrahydrofuran ID Tetrahydrofuran-d n-butyl alcohol IS 1,4-Difluorobenzene Isopropyl acetate IS 1,4-Difluorobenzene Cyclohexane ID Cyclohexane-d n-heptane ID n-heptane-d Methylisobutyl ketone IS 1,4-Difluorobenzene n-amyl alcohol IS 1,4-Difluorobenzene n-butyl acetate ID Chlorobenzene-d m/p-xylene ID p-xylene-d n-amyl acetate IS 1,4-Difluorobenzene o-xylene ID o-xylene-d IS = Quantitation by Internal Standard ID = Quantitation by Isotope Dilution RF = Response Factor %RSD = Percent Relative Standard Deviation R 2 = Linear correlation coefficient MDL = Statistical Method Detection Limit ML = Minimum Level required by Method 1666, Table 3

7 Calibration of Selected Nonpolar Compounds 5 ppb to 200 ppb Response (Area Cnts) 1.E+08 1.E+08 8.E+07 6.E+07 4.E+07 Trifluorochloromethane R 2 = n -Pentane R 2 = n -Hexane R 2 = Isopropyl ether R 2 = Ethyl acetate R 2 = Isopropyl ether Ethyl acetate 2.E+07 n -Hexane F 3 Cl methane 0.E+00 n -Pentane Concentration (ppb) Calibration of Selected Nonpolar Compounds 5 ppb to 200 ppb Response (Area Cnts) 1.E+08 9.E+07 8.E+07 7.E+07 6.E+07 5.E+07 4.E+07 3.E+07 2.E+07 Tetrahydrofuran R 2 = Isopropyl acetate R 2 = Cyclohexane R 2 = n -Heptane R 2 = Methylisobutyl ketone R 2 = Methylisobutyl ketone Isopropyl acetate Cyclohexane n -Heptane 1.E+07 Tetrahydrofuran 0.E Concentration (ppb) Figure 2. Calibration Curves for all Polar and Nonpolar Compounds

8 Calibration of Selected Nonpolar Compounds 5 ppb to 200 ppb Response (Area Cnts) 1.E+08 1.E+08 1.E+08 8.E+07 6.E+07 4.E+07 n -Butyl acetate R 2 = m/p -Xylene R 2 = n -Amyl acetate R 2 = o -Xylene R 2 = m/p -Xylene o -Xylene n -Amyl acetate n -Butyl acetate 2.E+07 0.E Concentration (ppb) Calibration of Polar Compounds 12.5 ppb to 500 ppb Response (Area Cnts) 1.E+07 1.E+07 8.E+06 6.E+06 4.E+06 2.E+06 Methyl formate R 2 = Isopropyl alcohol R 2 = t -Butyl alcohol R 2 = n -Butyl alcohol R 2 = n -Amyl alcohol R 2 = t -Butyl alcohol Methyl formate Isopropyl alcohol n -Amyl alcohol n -Butyl alcohol 0.E Concentration (ppb) Figure 2 (cont.). Calibration Curves for all Polar and Nonpolar Compounds

9 Method Detection Limits and Minimum Levels Method Detection Limit (MDL) is defined as the minimum concentration of a substance that can be measured and reported with 99% confidence that the analyte concentration is greater than zero... 5 To determine the MDL, nine aliquots of the 5.0-ppb standard were analyzed, and the concentrations were calculated using the initial calibration curve. The MDLs were calculated by multiplying the standard deviation of the nine replicate runs by the student t value for the 99% confidence level (MDL = standard deviation x 2.896). Calculated MDLs range from 0.13 ppb for cyclohexane to 2.58 ppb for t-butyl alcohol. All MDLs fell well below the Minimum Levels (MLs) of 5 10 ppb for nonpolar compounds or ppb for the water soluble compounds specified in the method (USEPA Method 1666, Table 3). USEPA Method 1666 defines Minimum Level as the level at which the entire system shall give recognizable mass spectra (background corrected) and acceptable calibration points... While there is a difference between MDL and ML, it can be useful to compare the two. For example, the method specifies a ML of 200 ppb for isopropanol, and the calculated MDL was 1.69 ppb. Statistical MDLs determined for all 20 compounds are tabulated in Table 3. All analyses at the lowest calibration point (5 or 12.5 ppb) met the criteria outlined for MLs. Reproducibility Method accuracy and precision were estimated by analyzing either nine or five replicate runs of the analytical standards at concentrations across the calibration range. Table 4 details the average recoveries and %RSDs for all compounds at several different concentrations. Results were excellent for the 20 compounds, with %RSDs for the water soluble, polar compounds consistently higher than those for the nonpolar compounds, as expected. Analyte recoveries all fell well within the method acceptance criteria for ongoing recovery performance tests (Method 1666, Table 6). Conclusion The instrument configuration and operating conditions described here produce outstanding method performance for the target analyte list in USEPA Method Calibration RFs, RSDs, MDLs, accuracy, and precision for all 20 target compounds meet or exceed all specified method performance criteria. Optimized purge-and-trap design permits heated sample purging, eliminates cold spots, and optimizes water management for improved performance of the water soluble, polar compounds.

10 Table 4. Reproducibility and Percent Recovery for all Compounds Across the Calibration Range Sample Concentration Method 5 ppb 20 ppb 200ppb Criteria (n=9) (n=9) (n=5) Compound Name %Recy %RSD %Recy %RSD %Recy %RSD %Recy Internal Standards Bromochloromethane ,4-Difluorobenzene Chlorobenzene-d Labeled Compounds t-butyl alcohol-d n-hexane-d Ethyl acetate- 13 C Tetrahydrofuran-d Cyclohexane-d n-heptane-d m-xylene-d o-xylene-d Target Analytes Methyl formate Trichlorofluoromethane Isopropanol D n-pentane t-butyl alcohol D n-hexane Isopropyl ether Ethyl acetate Tetrahydrofuran n-butyl alcohol D Isopropyl acetate Cyclohexane n-heptane Methylisobutyl ketone n-amyl alcohol n-butyl acetate m/p-xylene n-amyl acetate o-xylene

11 References 1. Pharmaceutical Manufacturing Category Effluent Limitations Guidelines, Pretreatment Standards, and New Source Performance Standards; Final Rule, 40 CFR Parts 136 and 439; U.S. Environmental Protection Agency, September 21, Analytical Method Guidance for the Pharmaceutical Manufacturing Industry, Point Source Category, USEPA Office of Water, May USEPA Method 1666, Volatile Organic Compounds Specific to the Pharmaceutical Manufacturing Industry by Isotope Dilution GC/MS, Revision A, USEPA Office of Water, July Abeel, S.M.; Vickers, A.K.; Decker, D. Trends in Purge and Trap. J. Chromatogr. Sci. 1994, 32, Appendix B to Part 136 Definition and Procedure for the Determination of the Method Detection Limit, Revision Federal Reg. 1984, 49,

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