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Interactions of Emerging Contaminants- Antibiotics with Functionalized Biochar Prof John L Zhou, Md. B. Ahmed School of Civil and Environmental Engineering UTS 21 August 2018 Graphics created by by created Graphics volupta re conecum Ullupta doluptuam. et pe evelignis BIOCHAR 2018 2 Outline of the Talk 1. Antibiotic residues in the environment 2. Preparation and characterization of functionalized biochar 3. Application of functionalized biochar in antibiotic removal from water and wastewater 4. Conclusions BIOCHAR 2018 3 Emerging Contaminants in the Environment • Pharmaceuticals and personal care products (PPCPs) • Nano-materials • Disinfection by-products • New pesticides • Degradation products Halpern et al. (2008) Science 319, 948 BIOCHAR 2018 4 Pharmaceutical Residues in the Environment • Of the greatest concern worldwide are pharmaceuticals, in particular antibiotic residues: ü Produced in large quantity, e.g. > 25000 tons per annum produced in China alone. ü Between 80-90% are excreted unmetabolized once consumed in human and animals. ü Poorly removed in sewage treatment plants. ü Potential to cause antibiotic resistance, leading to the so-called “superbugs” with antibiotic resistance genes. BIOCHAR 2018 5 Comparative Removal Efficiency of Emerging Contaminants Ahmed et al. (2017) JHM 323, 274-298 BIOCHAR 2018 6 Antibiotic Resistance Germs Take a Bite Out of Antibiotics D-CYCLOSERINE AMIKACIN GENTAMICIN KANAMYCIN SISOMICIN CHLORAMPHENICOL THIAMPHENICOL CARBENICILLIN DICLOXACILLIN PENICILLIN G VANC OM YC IN CIPROFLOXACIN LEVOFLOXACIN NALIDIXIC ACID MAFENIDE Taste test. Harvard University researchers Morten SULFAMETHIZOLE SULFISOXAZOLE Sommer and Gautam Dantas and colleagues used TRIMETHOPRIM soil samples from a Massachusetts forest and a cornfield (inset) to screen for antibiotic-eating Growth No Growth microbes. Science (2008) 320, 33 BIOCHAR 2018 7 Antibiotics in Water and Sediments from Mariculture Sites in China Chen et al. (2017) STOTEN 580, 1175 BIOCHAR 2018 8 Outline of the Talk 1. Antibiotic residues in the environment 2. Preparation and characterization of functionalized biochar 3. Application of functionalized biochar in antibiotic removal from water and wastewater 4. Conclusions BIOCHAR 2018 9 Why Biochar and Functionalized Biochar? 1000000 • Biochar is a C-rich product obtained Lower price Higher price 100000 when biomass is heated at elevated temperature in a closed reactor with little 10000 or no available air. 1000 • Functionalized biochar (fBC) is obtained 100 when biochar is further treated either 10 chemically or physically in order to Price of adsorbent ($/kg) improve its functional groups and 1 sorption performance. 0.1 BCs ACs Resins MWCNTs SWCNTs Adsorbent Ahmed et al. (2015) STOTEN 532, 112-126 BIOCHAR 2018 10 Preparation of Biochar and Functionalized Biochar Wash & Pyrolysis at Increased N Crushed into Cut into 2 Cooling at Biomass drying at 380 °C for 2 h pressure 10 psi at desired size, Biochar small sizes room 105 °C at 2 psi 380 °C for 15 min temp. wash with DI (BBC380) & drying Gasses Outlet N2 Inlet Vent Pyrolyser Head Soaking in Wash 50% Leave at Heated at Cooling with DI & Biochar phosphoric 50 °C for 600 °C for 2 adjust Screws in room fBC acid 3 h h at 2.0 psi temp. pH to solution 7.0 and Valve dry Pyrolysis Chamber Furnace N2 Cylinder BIOCHAR 2018 11 Physicochemical Properties of Biochar & fBC Sample Composition data Yielddry basis (%) Moisture content (%) Ash (%) Volatile mater (%) Fixed carbon (%) Biomass 5.61 12.93 63.83 26.67 BBC380 43.50 1MbBBC600 Initial pH 1.62 3.00 4.35 6.13 10.00 Final pH 1.15 2.74 3.39 4.09 8.28 Zeta potential (mV) 5.34±0.32 -3.25±0.24 -12.76±1.23 -19.6±1.15 -45.9±4.67 Sample EDS analysis BET surface area BJH Adsorption pore diameter C % O% P% Molar O/C BBC380 81.18 18.83 - 0.232 0.50 m2 g-1 113.5 Å 1MbBBC600 51.96 39.52 8.16 0.761 1.12 m2 g-1 83.8 Å 1 BIOCHAR 2018 12 SEM of BBC380 and 1MbBBC600 BIOCHAR 2018 13 Raman Spectra of fBC FTIR Spectra of fBC Zeta Potential Value of fBC is 2.20 BIOCHAR 2018 14 XPS Spectra of fBC Name Peak BE Atomic % Surface group Assignment C (1s) A 284.8 56.98 C=C Graphitic carbon C (1s) B 286.27 13.6 C-O- Phenolic, alcoholic, etheric C (1s) C 287.8 4.15 C=O Carbonyl or quinone C (1s) D 289 3.13 COO- Carboxyl or ester C (1s) E 290.54 2.77 C=O/ C=C Carbonate, ocluded CO, p-electrons in aromatic ring C (1s) F 292.35 1.13 π-π* transition The transition due to conjugation N (1s) 401.47 0.8 C–N+H-C Forms of quaternary nitrogen, protonated pyridinic ammonium ions, nitrogen atoms replacing carbon in graphene, O (1s) B 533.3 8.52 C-O- Oxygen singly bonded to carbon in aromatic rings, in phenols and ethers O (1s) A 531.62 4.8 C=O Oxygen doubly bonded to carbon P (2p) 133.79 2.3 C-O-PO3 Polyphosphates and/or phosphates BIOCHAR 2018 15 Outline of the Talk 1. Antibiotic residues in the environment 2. Preparation and characterization of functionalized biochar 3. Application of functionalized biochar in antibiotic removal from water and wastewater 4. Conclusions BIOCHAR 2018 16 Single and Competitive Sorption of Sulfonamides by fBC H2N CH3 pK a1 O SMT N R S 1 NH O H N pK N CH STZ 2 a2 3 pK SMT a1 O N SMX S R NH 2 O pK S Sulfonamide 3D structures H2N a2 STZ pK a1 O + + + SMT / SMX /STZ - - - N O SMT / SMX /STZ S R NH 3 O pK CH3 a2 0 0 0 SMX SMT / SMX /STZ Sulfonamide structures H2N O +/- +/- +/- SMT / SMX /STZ S NH R 1/R2/R3 Sulfonamide species O General formula of sulfonamides BIOCHAR 2018 17 pH Effect on Sorption • Functionalized biochar can sorb antibiotics in both single and competitive mode • Sorption capacity for antibiotics was three times higher in single mode than in competitive mode • Sorption capacity decreases as sulfathiazole > sulfamethoxazole > sulfamethazine • Solution pH is a significant parameter for removing ionisable sulfonamides • Sorption is mostly governed by the H-bond formation and π-π interactions Ahmed et al. (2017) CEJ 311, 348-358 BIOCHAR 2018 18 Proposed Sorption Mechanism - H δ + SMX O δ .. π O R N S NH2 SMT - .. π δ - δ H N S NH R O + 2 δ STZ at low pH + + Hδ O For neutral molecules π - π EDA - Lewis acid base interaction δ Diffusion .. O O H O: OH OH ligend exchange with -OH - δ P O group but not favorable O H π π H π OH R O π O Higher electron density π NH - δ O H O S O - CAHB + δ + δ δ H O at high pH O + π δ .. - - π EAA δ - π H N π π π - + 2 π S N R δ δ O H O O at higher pH where H H N O 2.. negative species O O exist (less favorable) H O CAHB - - δ- .. Oδ R N S π NH2 .. + - δ δ H N S N 2 π R O - at higher pH where negative species + δ O δ + Where, exist(mostly favored) Hδ R=R /R /R 1 2 3 π electron acceptor BIOCHAR 2018 19 Sorption of Chloramphenicol 2.4x105 (a) STZ (b) 5 10 2.1x10 SMX 10 10 SMT 5 1.8x10 CP (c) 0 8 8 1.5x105 ) -1 ) -10 -1 5 6 1.2x10 SMZ 6 (L kg (L SMT (mg g d s -20 SMX q K 4 9.0x10 4 CP PSO kinetic model fit for STZ 4 PSO kinetic model fit for SMT 4 (mV) potential Zeta -30 6.0x10 PSO kinetic model fit for SMX 2 PSO kinetic model fit for CP PFO kinetic model fit for STZ 4 2 3.0x10 PFO kinetic model fit for SMT -40 Zeta potential of fBC PFO kinetic model fit for SMX Initial sorption solution pH 0 PSO kinetic model fit for CP pH = 2.2 0.0 pzc Equlibrium sorption solution pH 1 2 3 4 5 6 7 8 9 10 11 0 200 400 600 800 1000 1200 1400 1600 1800 2000 -50 0 0 1 2 3 4 5 6 7 8 9 10 11 pH Time (min) pH (a) Effect of pH on Kd, (b) Sorption kinetics, (c) zeta potential of functionalized biochar Ahmed et al. (2017) BT 238, 306-3112 BIOCHAR 2018 20 Sorption of Chloramphenicol: Mechanism Resonance Structures Sorption Affinity M echanisms Competitive Sorption Affinity: STZ> SMX> CP >SMT - p-electron acceptor sites OHO Cl d + At very low pH: O d - d + (i). Repulsion interactions + .. d R NH dS NH O NH Cl (ii). BC-OH + sulfonamides/CP = EDA interactions d- 2 + d N - d-O d At pH 4.0-4.25: - + - Sulfonamides, R= Hetrocyclic -O OH d (i). BC-COO .....H .... O2N-chloramphenicol = CAHB formations with EDA interactions rings for SM T, STZ & SM X Chloramphenicol (ii). BC-COO..H + sulfonamides (NHSO 2-/NH/ -NH 2/CH3) = H-bond formations p-electron donor site At pH above 7.0: - + d - - d + d - (i). Repulsion interactions O d d ..+ .. (ii). Sulfonamides-N-+ H O = sulfonamides-NH + -OH+ O 2 O..H + + - - + - d d .. (iii). BC-O....H + N....sulfonamides =BC-O .....H .... N..sulfonamides = CAHB OH BC-C=O + BC-OH BC-COOH (iv). BC-OH + chloramphenicol (H /-OH/NO2/-NH-/-Cl) = H-bond formations Comparative Treatment Trend: Deionized water> Lake water > Synthetic wastewater BIOCHAR 2018 21 Sorption of Antibiotics in Mixture Mode Lake water Synthetic wastewater STZ SMX STZ SMX SMT CP SMT CP 100 100 (a) (b) 80 80 60 60 Percentage Percentage 40 40 20 20 200 300 400 500 600 700 200 300 400 500 600 700 fBC dosage (mg L-1) fBC dosage (mg L-1) BIOCHAR 2018 22 (a) Effects of Sample Composition on Chloramphenicol Sorption (b) Regeneration of Functionalized Biochar at 300 oC rd th fBC-2 (1st cycle) fBC-2 (3 cycle) fBC-2 (5 cycle) th th fBC-2 (2nd cycle) fBC-2 (4 cycle) fBC-2 (6 cycle) 100 3.0 Synthetic wastewater (a) (b) Lake water Deionized water 2.5 80 ) -1 2.0 M L M 60 μ ( 1.5 40 1.0 Residual conc.
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