Enhanced biodegradation of carbamazepine after UV/H 2 O 2 advanced. oxidation
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1 Supporting Information for the Environmental Science and Technology article: Enhanced biodegradation of carbamazepine after UV/H 2 O 2 advanced oxidation Prepared for submission to Environmental Science and Technology September 2011 Olya S. Keen 1, Seungyun Baik 2, Karl G. Linden 1*, Diana S. Aga 2 and Nancy G. Love 3 1 Civil, Environmental and Architectural Engineering, University of Colorado Boulder 2 Chemistry Department, University at Buffalo, The State University of New York, Buffalo, NY 3 Civil and Environmental Engineering Department, University of Michigan Ann Arbor * Corresponding author: karl.linden@colorado.edu 10 pages, including 1 narrative, 1 table and 7 figures S1
2 Text S1: Liquid chromatography/mass spectrometry analysis details Analyses for CBZ and byproducts in samples were performed using liquid chromatographer with ion trap mass spectrometer (LC-ITMS) detection (LCQ Advantage, Thermo Finnigan, CA, USA) equipped with a UV 6000LP UV-vis diode array detector. Analysis was performed using an electrospray ionization (ESI) source in positive ion mode. Data were collected under full scan conditions, from 50 to 500 m/z. Nitrogen gas was used as sheath gas. Electrospray voltage was 4500 V and capillary temperature and voltage were 250 ºC and 41 V, respectively. Separation was achieved using a Betabasic-18 C 18 column, (100 X 2.1 mm i.d., 3 µm particle size), equipped with a guard cartridge (10 X 2.1 mm i.d., 3 µm particle size) (Thermo Fisher Scientific, Waltham, MA). The gradient mobile phase consisted of LC/MSgrade acetonitrile (A, Honeywell B & J, Muskegon, MI) and Nanopure water with 0.3% formic acid (B). The initial conditions were 2% A and 98% B; after 5 min, A was increased to 95% over 15 minutes; this was held for 4 more minutes. The initial mobile phase condition was then restored within 1 min, and run for 5 more min to maintain the condition. The flow rate was set at 200 µl/min, the injection volume was 10 µl, and the column oven temperature was held at 30ºC. The total run time was 30 min, including post-run protocols. For radioactive samples, analysis was performed using Surveyor HPLC (Thermo Finnigan, San Jose, CA) equipped with an online radiochromatographic detector (IN/US Systems, Inc., Tampa, FL), which uses a flow-through cell with a volume of 0.5 ml and a 3:1 scintillation fluid/eluent ratio (Ecoscint, National Diagnostics, Atlanta, GA). For qualitative analysis, 3 ml aliquots were taken from each sample and reduced to 0.2 ml under a gentle stream of nitrogen. Furthermore, selected samples were subjected to a clean-up procedure using solid phase extraction (SPE) to reduce the sample matrix that affects both S2
3 separation and the signals of the analytes in the LC-ITMS. The SPE eluates were reduced in volume to 0.2 ml prior to analysis by LC-radiochromatography, and the results were compared with the samples that were concentrated by direct evaporation (without SPE clean up). For the SPE preparation, Phenomenex Strata-X (Polymeric Reversed Phase, 200 mg, 3 ml) cartridges were pre-conditioned with 3 ml HPLC-grade methanol (Honeywell B & J, Muskegon, MI) and washed with 3 ml Nanopure water. Cartridges were then loaded with 1 ml sample and 2 ml Nanopure water mixture. Cartridges were then washed with 4 ml 5% (v/v) HPLC-grade methanol and the eluate from each cartridge was collected. After 1 min of drying, cartridges were eluted with 4 ml 50:50 of HPLC-grade methanol and acetonitrile (Sigma-Aldrich, St. Louis, MO). At each step in the SPE procedure, a small aliquot was taken from the eluate and from the waste for analysis by LSC in order to check for percent recovery. S3
4 Table S1: Wastewater Treatment Plant Effluent Quality During Two Sampling Events. Water quality parameter Method used Units Effluent 1 Effluent 2 Alkalinity Hach digital titrator mg/l as CaCO ph Beckman ph meter Ammonium Nitrite Nitrate Dissolved organic carbon Total nitrogen Hach colorimetric test kit Hach colorimetric test kit Hach colorimetric test kit Shimadzu TOC analyzer Shimadzu TN analyzer mg/l as N < mg/l as N < < mg/l as N mg/l as C 7.5 -* mg/l as N * * TOC/TN measurement was discarded due to analytical problems that were discovered later. S4
5 (4) (3) (2) (1) Figure S1: Experimental setup for assessing the biological stability of effluents treated with AOP versus those not treated with AOP. The building air delivered to the system passed through a regulator which assured constant flow (1), a 0.2 micron filter removed non-gaseous particles (2), a check valve prevented backflow (3), and a wash bottle hydrated the air to minimize sample evaporation (4). Air was delivered to the samples through a series of manifolds. Each bottle had an individual regulator valve allowing for the gaseous flow rate to be adjusted. S5
6 % Radioactivity % Radioactivity Retention time, min Figure S2: Oxidation products retained after rotary evaporation (top) compared to solid phase extraction (bottom). S6
7 Normalized SUVA without CBZ with CBZ Duration of biodegradation, days Figure S3: Change in SUVA 254 during degradation of effluent with activated sludge, both with and without CBZ. S7
8 Pre-AOP sample Pre-AOP control Post-AOP sample Post-AOP control Figure S4: Sample 1 mass balance. Light gray color fraction of radioactivity due to parent compound and products still in solution. Dark gray color fraction of radioactivity that migrated into the KOH traps as CO 2, i.e. fraction of the radiolabeled compound fully mineralized. The results are for one of the two replicates. Left - samples; right - controls (Sample + NaN 3 ); top before AOP; bottom after AOP. The values are the means of several measurements taken from the same sample with error bars representing 95% confidence intervals for the measurements. S8
9 Pre-AOP sample Pre-AOP control Post-AOP sample Post-AOP control Days of biodgeradation Figure S5: Sample 2 mass balance. Light gray color fraction of radioactivity due to parent compound and products still in solution. Dark gray color fraction of radioactivity that migrated into the KOH traps as CO 2, i.e. fraction of the radiolabeled compound fully mineralized. The results are for the second of the two replicates. Left - samples; right - controls (Sample + NaN 3 ); top before AOP; bottom after AOP. The values are the means of several measurements taken from the same sample with error bars representing 95% confidence intervals for the measurements. S9
10 Intensity Retention time, min Figure S6: UV 254 absorbance chromatogram of the sample pretreated with AOP after 25 days of biodegradation. The main peak at min retention time is the parent CBZ. All other minor peaks were overlapped with their full-scan mass spectra, but none of these peaks showed m/z peak that corresponds to a tricyclic by-product of CBZ devoid of the 14 CONH 2 moiety. Intensity Retention time, min Figure S7: Extracted ion chromatogram for tricyclic fragment of CBZ (m/z 194) of the sample pretreated with AOP after 25 days of biodegradation. S10
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