Abstract
Activated carbons prepared from cashew nut shells by chemical activation with phosphoric acid were tested for the removal of acetaminophen. It was found that an increase in carbonization temperature resulted in increased pore volume and decreased amount of surface functional groups. Potentiometric titration analysis indicated that the majority of surface groups on carbons are acidic. Detailed surface characterization by FT-IR, XPS, and thermal analyses indicated the involvement of surface functional groups in the removal of acetaminophen either via hydrogen bonding or by acid hydrolysis. The carbon obtained at 600 °C, which contains high amount of carboxylic groups and high pore volume, exhibited the highest adsorption capacity. For this carbon, the removal of acetaminophen took place mostly via acid hydrolysis with the formation of p-aminophenol and acetic acid adsorbed on the surface. Carbon obtained at 400 °C was found to have the highest density of acidic functional groups, which resulted in dimerization reactions and pore blockage. No direct correlation was observed between the adsorption capacities of carbons and their textural or surface characteristics. This suggests the complexity of acetaminophen removal by the cashew nut shell-derived activated carbons, governed by their surface chemistry and supported by high surface area accessible via micro/mesopores.
Similar content being viewed by others
References
Ahmed MB, Zhou JL, Ngo HH, Guo W, Thomaidis NS, Xu J (2017) Progress in the biological and chemical treatment technologies for emerging contaminant removal from wastewater: a critical review. J Hazard Mater 323:274–298. https://doi.org/10.1016/j.jhazmat.2016.04.045
Annual Book of ASTM Standard (2011) Standard test for pH of Activated Carbon. ASTM D 3838–05, Philadelphia
Antunes SC, Freitas R, Figueira E, Gonçalves FJM, Nunes B (2013) Biochemical effects of acetaminophen in aquatic species: edible clams Venerupis decussata and Venerupis philippinarum. Environ Sci Pollut Res Int 20:6658–6666. https://doi.org/10.1007/s11356-013-1784-9
Baccar R, Sarrà M, Bouzid J, Feki M, Blánquez P (2012) Removal of pharmaceutical compounds by activated carbon prepared from agricultural by-product. Chem Eng J 211-212:310–317. https://doi.org/10.1016/j.cej.2012.09.099
Bandosz TJ, Jagiello J, Contescu C, Schwarz JA (1993) Characterization of the surfaces of activated carbons in terms of their acidity constant distributions. Carbon 31:1193–1202. https://doi.org/10.1016/0008-6223(93)90072-I
Bernal V, Erto A, Giraldo L, Moreno-Pirajan JC (2017) Effect of solution pH on the adsorption of paracetamol on chemically modified activated carbons. Molecules 22:1032–1046. https://doi.org/10.3390/molecules22071032
Biniak S, Szymański GS, Siedlewski ZJ, Świątkowski A (1997) The characterization of activated carbons with oxygen and nitrogen surface groups. Carbon 35:1799–1810. https://doi.org/10.1016/S0008-6223(97)00096-1
Cabrita I, Ruiz B, Mestre AS, Fonseca IM, Carvalho AP, Ania CO (2010) Removal of an analgesic using activated carbons prepared from urban and industrial residues. Chem Eng J 163:249–255. https://doi.org/10.1016/j.cej.2010.07.058
Chen YJ, Bao H, Yang P (2002) Determination of the rate constants and activation energy of acetaminophen hydrolysis by capillary electrophoresis. J Pharm Biomed Anal 29:843–850. https://doi.org/10.1016/S0731-7085(02)00211-X
Chowdhury ZZ, Hamid SBA, Das R, Hasan MR, Zain S, Khalisanni K, Uddin MN (2013) Preparation of carbonaceous adsorbents from lignocellulosic biomass and their use in removal of contaminants from aqueous solution. Bioresources 8:6523–6555. https://doi.org/10.15376/biores.8.4.6523-6555
Cloirec PL, Faur C (2006) Adsorption of organic compounds onto activated carbon – applications in water and air treatments. In: Bandosz TJ (ed) Activated carbon surfaces in environmental remediation. Elsevier, Oxford, pp 375–419
Das SK, Dickinson C, Lafir M, Broughamc DF, Marsili E (2012) Synthesis, characterization and catalytic activity of gold nanoparticles biosynthesized with Rhizopus oryzae protein extract. Green Chem 5:S1–S8. https://doi.org/10.1039/C2GC16676C
David A, Pancharatna K (2009) Effects of acetaminophen (paracetamol) on the embryonic development of zebra fish, Danio rerio. J Appl Toxicol 29:597–602. https://doi.org/10.1002/jat.1446
Deegan AM, Shaik B, Nolan K, Urell K, Oelgemöller M, Tobin J, Morrissey A (2011) Treatment options for wastewater effluents from pharmaceutical companies. Int J Environ Sci Technol 8:649–666. https://doi.org/10.1007/BF03326250
Demiral H, Baykul E, Gezer MD, Erkoҫ S, Engin A, Baykul MC (2014) Preparation and characterization of activated carbon from chestnut shell and its adsorption characteristics for lead. Sep Sci Technol 49:2711–2720. https://doi.org/10.1080/01496395.2014.942742
Dutta M, Das U, Mondal S (2015) Adsorption of acetaminophen by using tea waste derived activated carbon. Int J Environ 6:270–281. https://doi.org/10.6088/ijes.6031
Ebele AJ, Abdallah MA-E, Harrad S (2017) Pharmaceuticals and personal care products (PPCPs) in the freshwater aquatic environment. Emerg Contam 3:1–16. https://doi.org/10.1016/j.emcon.2016.12.004
Fallou H, Cimetière N, Giraudet S, Wolbert D, Cloirec PLE (2016) Adsorption of pharmaceuticals onto activated carbon fiber cloths – modeling and extrapolation of adsorption isotherms at very low concentrations. J Environ Manag 166:544–555. https://doi.org/10.1016/j.jenvman.2015.10.056
Ferreira RC, De Lima HHC, Cândido AA, Couto OM Jr, Arroyo PA, De Carvalho KQ, Gauze GF, Barros MASD (2015) Adsorption of paracetamol using activated carbon of dende and babassu coconut mesocarp. Int J Biol Biomol Agr Food Biotechnol Eng 9:717–722 https://waset.org/Publication/10001579
Figueiredo JL, Pereira MFR, Freitas MMA, Órfão JJM (1999) Modification of the surface chemistry of activated carbons. Carbon 36:1379–1389. https://doi.org/10.1016/S0008-6223(98)00333-9
Galhetas M, Mestre AS, Pinto ML, Gulyurtlu I, Lopes H, Carvalho AP (2014) Carbon-based materials prepared from pine gasification residues for acetaminophen adsorption. Chem Eng J 240:344–351. https://doi.org/10.1016/j.cej.2013.11.067
García-Mateos FJ, Moulefera I, Rosas JM, Benyoucef A, Rodríguez-Mirasol J, Cordero T (2017) Alcohol dehydrogenation on Kraft lignin-derived chars with surface basicity. Catalysts 7:308–322. https://doi.org/10.3390/catal7100308
Giannakoudakis DA, Hosseini-Bandegharaei A, Tsafrakidou P, Triantafyllidis K, Kornaros M, Anastopoulos I (2018) Aloe vera waste biomass-based adsorbents for the removal of aquatic pollutants: a review. J Environ Manag 227:354–364. https://doi.org/10.1016/j.jenvman.2018.08.064
Gregg SJ, Sing KSW (1982) Adsorption, surface area, and porosity, 2nd edn. Academic Press, London
Guo Y, Qi PS, Liu YZ (2017) A review on advanced treatment of pharmaceutical wastewater. IOP Conf Ser Earth Environ Sci 63:012025 http://iopscience.iop.org/1755-1315/63/1/012025
Ho YS, McKay G (1999) Pseudo-second-order model for sorption processes. Process Biochem 34:451–465. https://doi.org/10.1016/S0032-9592(98)00112-5
Iovino P, Canzano S, Capasso S, Erto A, Musmarra D (2015) A modeling analysis for the assessment of ibuprofen adsorption mechanism onto activated carbons. Chem Eng J 277:360–367. https://doi.org/10.1016/j.cej.2015.04.097
Jagiello J, Bandosz TJ, Putyera K, Schwarz JA (1995) Determination of proton affinity distributions for chemical systems in aqueous environments using a stable numerical solution of the adsorption integral equation. J Colloid Interface Sci 172:341–346. https://doi.org/10.1006/jcis.1995.1262
Jones OAH, Voulvoulis N, Lester JN (2007) The occurrence and removal of selected pharmaceutical compounds ina sewage treatment works utilizing activated sludge treatment. Environ Pollut 145:738–744. https://doi.org/10.1016/j.envpol.2005.08.077
Joss A, Keller E, Alder AC, Göbel A, McArdell CS, Ternes T, Siegrist H (2005) Removal of pharmaceuticals and fragrances in biological wastewater treatment. Water Res 39:3139–3152. https://doi.org/10.1016/j.watres.2005.05.031
Kampouraki ZC, Giannakoudakis DA, Triantafyllidis KS, Deliyanni EA (2019) Catalytic oxidative desulfurization of a 4,6-DMDBT containing model fuel by metal-free activated carbons: the key role of surface chemistry. Green Chem 21:6685–6698. https://doi.org/10.1039/C9GC03234G
Kaufman DW, Kelly JP, Rosenberg L, Anderson TE, Mitchell AA (2002) Recent patterns of medication use in the ambulatory adult population of the United States: the Slone survey. J Am Med Assoc 287:337–344. https://doi.org/10.1001/jama.287.3.337
Kostich MS, Batt AL, Lazorchak JM (2014) Concentrations of prioritized pharmaceuticals in effluents from 50 large wastewater treatment plants in the US and implications for risk estimation. Environ Pollut 184:354–359. https://doi.org/10.1016/j.envpol.2013.09.013
Kumar A, Jena HM (2016) Preparation and characterization of high surface area activated carbon from fox nut (Euryale ferox) shell by chemical activation with H3PO4. Results Phys 6:651–658. https://doi.org/10.1016/j.rinp.2016.09.012
Kyzas GZ, Deliyanni EA (2015) Modified activated carbons from potato peels as green environmental-friendly adsorbents for the treatment of pharmaceutical effluents. Chem Eng Res Des 97:135–144. https://doi.org/10.1016/j.cherd.2014.08.020
Lagergren S (1898) Zur Theorie der Sogenannten Adsorption Gelöster Stoffe, Kungliga Svenska Vetenskapsakademiens. Handlingar 24:1–39
Lastoskie C, Gubbins KE, Quirke NJ (1993) Pore size distribution analysis of microporous carbons: density functional theory approach. Phys Chem 97:4786–4796. https://doi.org/10.1021/j100120a035
László K, Josepovits K, Tombácz E (2001) Analysis of active sites on synthetic carbon surfaces by various methods. Anal Sci 17:1741–1744. https://doi.org/10.14891/analscisp.17icas.0.i1741.0
Lee WM (2008) Etiologies of acute liver failure. Semin. Liver Dis 28:142–152. https://doi.org/10.1055/s-2008-1073114
Li L, Yao X, Li H, Liu Z, Ma W, Liang X (2014) Thermal stability of oxygen-containing functional groups on activated carbon surfaces in a thermal oxidative environment. J Chem Eng Jpn 47:21–27. https://doi.org/10.1252/jcej.13we193
Lide DR (2005) RC handbook of chemistry and physics, 85th edn. CRC press, Boca Raton
Lladó J, Lao-Luque C, Ruiz B, Fuente E, Solé-Sardans M, Dorado AD (2015) Role of activated carbon properties in atrazine and paracetamol adsorption equilibrium and kinetics. Process Saf Environ 95:51–59. https://doi.org/10.1016/j.psep.2015.02.013
Mansouri H, Carmona RJ, Gomis-Berenguer A, Souissi-Najar S, Ouederni A, Ania CO (2015) Competitive adsorption of ibuprofen and amoxicillin mixtures from aqueous solution on activated carbons. J Colloid Interface Sci 449:252–260. https://doi.org/10.1016/j.jcis.2014.12.020
Matsuoka M, Isotani S, Mansano RD, Sucasaire W, Pinto RAC, Mittani JCR, Ogata K, Kuratani N (2012) X-ray photoelectron spectroscopy and Raman spectroscopy studies on thin carbon nitride films deposited by reactive RF magnetron sputtering. World J Nanosci Eng 2:92–102. https://doi.org/10.4236/wjnse.2012.22012
Mestre AS, Pires J, Nogueira JMF, Parra JB, Carvalho AP, Ania CO (2009) Waste-derived activated carbons for removal of ibuprofen from solution: role of surface chemistry and pore structure. Bioresour Technol 100:1720–1726. https://doi.org/10.1016/j.biortech.2008.09.039
Mestre AS, Bexiga AS, Proença M, Andrade M, Pinto ML, Matos I, Fonseca IM, Carvalho AP (2011) Activated carbons from sisal waste by chemical activation with K2CO3: kinetics of paracetamol and ibuprofen removal from aqueous solution. Bioresour Technol 102:8253–8260. https://doi.org/10.1016/j.biortech.2011.06.024
Mestre AS, Pires RA, Aroso I, Fernandes EM, Pinto ML, Reis RL, Andrade MA, Pires J, Silva SP, Carvalho AP (2014) Activated carbons prepared from industrial pre-treated cork: sustainable adsorbents for pharmaceutical compounds removal. Chem Eng J 253:408–417. https://doi.org/10.1016/j.cej.2014.05.051
Miranda WJNG, Yap GS, Sivadas M (1989) Biological treatment of a pharmaceutical wastewater. Biol Wastes 29:299–311. https://doi.org/10.1016/0269-7483(89)90021-9
Mohan D, Sarswat A, Singh VK, Alexandre-Franco M, Pittman CU Jr (2011) Development of magnetic activated carbon from almond shells for trinitrophenol removal from water. Chem Eng J 172:1111–1125. https://doi.org/10.1016/j.cej.2011.06.054
Moreno-Castilla C, López-Ramón MV, Carrasco-Marín F (2000) Changes in surface chemistry of activated carbons by wet oxidation. Carbon 1995-2001. https://doi.org/10.1016/S0008-6223(00)00048-8
Mostazo-López MJ, Salinas-Torres D, Ruiz-Rosas R, Morallón E, Cazorla-Amorós D (2019) Nitrogen-doped superporous activated carbons as electrocatalysts for the oxygen reduction reaction. Materials 12:1346–1363. https://doi.org/10.3390/ma12081346
Nassiri KN, Abdollahi M (2017) Health risks associated with the pharmaceuticals in wastewater. DARU J Pharma Sci 25:9–15. https://doi.org/10.1186/s40199-017-0176-y
Nche NAG, Bopda A, Tchuifon DRT, Ngakou CS, Kuete IHT, Gapche AS (2017) Removal of paracetamol from aqueous solution by adsorption onto activated carbon prepared from rice husk. J Chem Pharm Res 9:56–68
Nielsen L, Biggs MJ, Skinner W, Bandosz TJ (2014) The effects of activated carbon surface features on the reactive adsorption of carbamazepine and sulfamethoxazole. Carbon 80:419–432. https://doi.org/10.1016/j.carbon.2014.08.081
Ocampo-Perez R, Aguilar-Madera CG, Diaz-Blancas V (2017) 3D modelling of overall adsorption rate of acetaminophen on activated carbon pellets. Chem Eng J 321:510–520. https://doi.org/10.1016/j.cej.2017.03.137
Placke ME, Wyand DS, Cohen SD (1987) Extrahepatic lesions induced by acetaminophen in the mouse. Toxicol Pathol 15:381–387. https://doi.org/10.1177/019262338701500401
Puziy AM, Poddubnaya OI, Martınez-Alonso A, Suarez-Garcıa F, Tascon JMD (2002) Synthetic carbons activated with phosphoric acid: I. Surface chemistry and ion binding properties. Carbon 40:1493–1505. https://doi.org/10.1016/S0008-6223(01)00317-7
Ruiz B, Cabrita I, Mestre AS, Parra JB, Pires J, Carvalho AP, Ania CO (2010) Surface heterogeneity effects of activated carbons on the kinetics of paracetamol removal from aqueous solution. Appl Surf Sci 256:5171–5175. https://doi.org/10.1016/j.apsusc.2009.12.086
Santos LH, Araújo AN, Fachini A, Pena A, Delerue-Matos C, Montenegro MC (2010) Ecotoxicological aspects related to the presence of pharmaceuticals in the aquatic environment. J Hazard Mater 175:45–95. https://doi.org/10.1016/j.jhazmat.2009.10.100
Schönherr J, Buchheim JR, Scholz P, Adelhelm P (2018) Boehm titration revisited (part II): a comparison of Boehm titration with other analytical techniques on the quantification of oxygen-containing surface groups for a variety of carbon materials. C 4: 21. https://doi.org/10.3390/c4020021
Schultz ST, Klonoff-Cohen HS, Wingard DL, Akshoomoff NA, Macera CA, Ji M (2008) Acetaminophen (paracetamol) use, measles-mumps-rubella vaccination, and autistic disorder: the results of a parent survey. Autism 12:293–307. https://doi.org/10.1177/1362361307089518
Sellaoui L, Lima EC, Dotto GL, Lamine AB (2017) Adsorption of amoxicillin and paracetamol on modified activated carbons: equilibrium and positional entropy studies. J Mol Liq 234:375–381. https://doi.org/10.1016/j.molliq.2017.03.111
Spagnoli AA, Giannakoudakis DA, Bashkova S (2017) Adsorption of methylene blue on cashew nut shell based carbons activated with zinc chloride: the role of surface and structural parameters. J Mol Liq 229:465–471. https://doi.org/10.1016/j.molliq.2016.12.106
Stevens JS, De Luca AC, Pelendritis M, Terenghi G, Downes S, Schroeder SLM (2013) Quantitative analysis of complex amino acids and RGD peptides by X-ray photoelectron spectroscopy (XPS). Surf Interface Anal 45:1238–1246. https://doi.org/10.1002/sia.5261
Sych NV, Trofymenko SI, Poddubnaya OI, Tsyba MM, Sapsay VI, Klymchuk DO, Puziy AM (2012) Porous structure and surface chemistry of phosphoric acid activated carbon from corncob. Appl Surf Sci 261:75–82. https://doi.org/10.1016/j.apsusc.2012.07.084
Szymański GS, Karpiński Z, Biniak S, Świątkowski A (2002) The effect of the gradual thermal decomposition of surface oxygen species on the chemical and catalytic properties of oxidized activated carbon. Carbon 40:2627–2639. https://doi.org/10.1016/S0008-6223(02)00188-4
Ternes TA, Meisenheimer M, McDowell D, Sacher F, Brauch HJ, Haist-Gulde B, Preuss G, Wilme U, Zulei-Seibert N (2002) Removal of pharmaceuticals during drinking water treatment. Environ Sci Technol 36:3855–3863. https://doi.org/10.1021/es015757k
Terzyk AP, Rychlicki G (2000) The influence of activated carbon surface composition on the adsorption of acetaminophen (paracetamol) in vitro. The temperature dependence of adsorption at the neutral pH. Colloids Surf A Physicochem Eng Asp 163:135–150. https://doi.org/10.1016/s0927-7757(00)00594-x
Torres AR (2003) Is fever suppression involved in the etiology of autism and neurodevelopmental disorders? BMC Pediatr 3. https://doi.org/10.1186/1471-2431-3-9
Valero-Romero MJ, García-Mateos FJ, Rodríguez-Mirasol J, Cordero T (2017) Role of surface phosphorous complexes on the oxidation of porous carbons. Fuel Process Technol 157:116–126. https://doi.org/10.1016/j.fuproc.2016.11.014
Vieno NM, Tuhkanen T, Kronberg L (2005) Seasonal variation in the occurrence of pharmaceuticals in effluents from a sewage treatment plant and in the recipient water. Environ Sci Technol 39:8220–8226. https://doi.org/10.1021/es051124k
Villaescusa I, Fiol N, Poch J, Bianchi A, Bazzicalupi C (2011) Mechanism of paracetamol removal by vegetable wastes: the contribution of π-π interactions, hydrogen bonding and hydrophobic effect. Desalination 27:135–142. https://doi.org/10.1016/j.desal.2010.11.037
Watson DG (2017) Pharmaceutical analysis: a textbook for pharmacy students and pharmaceutical chemists, 4th edn. Elsevier, Edinburgh
Wu X, Radovic LR (2006) Inhibition of catalytic oxidation of carbon/carbon composites by phosphorus. Carbon 44:141–151. https://doi.org/10.1016/j.carbon.2005.06.038
Wu S, Zhang L, Chen J (2012) Paracetamol in the environment and its degradation by microorganisms. Appl Microbiol Biotechnol 96:875–884. https://doi.org/10.1007/s00253-012-4414-4
Yakout SM, Sharaf El-Deen G (2016) Characterization of activated carbons prepared by phosphoric acid activation of olive stones. Arab J Chem 9:S1155–S1162. https://doi.org/10.1016/j.arabjc.2011.12.002
Yang Y, Ok YS, Kim KH, Kwon EE, Tsang YF (2017) Occurrences and removal of pharmaceuticals and personal care products (PPCPs) in drinking water and water/sewage treatment plants: a review. Sci Total Environ 596-597:303–320. https://doi.org/10.1016/j.scitotenv.2017.04.102
Zawadzki J (1989) Infrared spectroscopy in surface chemistry of carbons. In: Thrower PA (ed) Chemistry and physics of carbon. Marcel Dekker, New York, pp 147–386
Zupanc M, Kosjek T, Petkovšek M, Dular M, Kompare B, Širok B, Blažeka Ž, Heath E (2013) Removal of pharmaceuticals from wastewater by biological processes, hydrodynamic cavitation and UV treatment. Ultrason Sonochem 20:1104–1112. https://doi.org/10.1016/j.ultsonch.2012.12.003
Acknowledgments
This work was supported by Novo Nordisk Undergraduate Research Program and Grant-In-Aid Program at Fairleigh Dickinson University. Authors are grateful to Vincent Menafro, Juster Rivera, and Tom Puleo for experimental help and Prof. Teresa J. Bandosz for providing the opportunity to use SAIEUS software.
Author information
Authors and Affiliations
Corresponding author
Additional information
Responsible editor: Tito Roberto Cadaval Jr
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Geczo, A., Giannakoudakis, D.A., Triantafyllidis, K. et al. Mechanistic insights into acetaminophen removal on cashew nut shell biomass-derived activated carbons. Environ Sci Pollut Res 28, 58969–58982 (2021). https://doi.org/10.1007/s11356-019-07562-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11356-019-07562-0