pp 1–11 | Cite as

Insight into adsorbate–adsorbent interactions between aromatic pharmaceutical compounds and activated carbon: equilibrium isotherms and thermodynamic analysis

  • Valentina Bernal
  • Liliana Giraldo
  • Juan Carlos Moreno-PirajánEmail author


The adsorption of phenol, salicylic acid and methylparaben on activated carbon is carried out using solvents with different pH, the adsorption and calorimetric data are analyzed in order to determine the effect of the substituent on the adsorption capacity. The adsorption isotherms were adjusted to the Langmuir model, which allows to assume the formation of specific adsorbate–adsorbent interactions between groups present in the adsorbate molecules, the substituents of the aromatic ring, and chemical groups on the activated carbon. According to the Lagmuir model the formation of specific interactions generates the monolayer adsorption so it is possible to correlate the adsorption capacity with changes in the interactions present in the system. It was determined that the adsorption process is disadvantaged at extremes pH values. From the Langmuir model it was calculated that the maximum adsorbed capacity of phenol and methylparaben in activated carbon granular activated carbon using water as solvent was 3.11 and 1.58 mmol g−1 respectively. The adsorption process of salicylic acid does not adjust to the Langmuir model due to the presence of different interactions that includes repulsion forces. From thermodynamic calculations and calorimetric data, it was determined that the immersion enthalpies vary between − 8.33 and − 59.3 J g−1, while the change in the enthalpy associated with interactions substituents-activated carbon is between − 15.1 and 6.40 J g−1 for the carboxylic acid and between − 0.50 and 20.0 J g−1 for the ester group.


Adsorption activated carbon Gibbs energy Immersion enthalpy Interactions Methylparaben Phenol and salicylic acid Salicylic acid 



The authors thank the Framework Agreement between the Universidad de Los Andes and the National University of Colombia and the act of agreement established between the Chemistry Departments of the two universities. The authors also appreciate the grant for the funding of research programs for Associate Professors, Full Professors, and Emeritus Professors announced by the Faculty of Sciences of the University of the Andes, 20-12-2019-2020, 2019, according to the project “Enthalpy, free energy and adsorption energy of the activated carbon interaction and solutions of emerging organic compounds”.


  1. Afrin, S., Simol, H.A., Sultana, G.N.N., Islam, M.S., Haque, P., Khan, M.N., Rahman, M.M.: Determination of serum methylparaben concentrations of Bangladeshí breast cancer patients by RP-HPLC. Anal. Chem. Lett. 7, 589–595 (2017)CrossRefGoogle Scholar
  2. Bernal, V., Erto, A., Giraldo, L., Moreno-Piraján, J.C.: Effect of pH solution on the adsorption of paracetamol on chemically modified activated carbons. Molecules 22, 1032 (2017)CrossRefGoogle Scholar
  3. Bernal, V., Giraldo, L., Moreno-Piraján, J.C.: Thermodynamic study of the interactions of salicylic acid and granular activated carbon in solution at different pHs. Adsorpt. Sci. Technol. 36, 833–850 (2018)CrossRefGoogle Scholar
  4. Bläker, C., pasel, C., Luckas, M., dreisbach, F., Bathen, D.: Investigation of load-dependent heat of adsorption of alkanes and alkenes on zeolite and activated carbon. Microporous Mesoporous Mater. 241, 1–10 (2017)CrossRefGoogle Scholar
  5. Boehm, H.P.: surface oxides on coal and their analysis: a critical assessment. Coal 40, 145–149 (2002)Google Scholar
  6. Carvajal-Bernal, A.M., Gomez-Granados, F., Giraldo, L., Moreno-Piraján, J.C.: Calorimetric evaluation of activated carbons modified for phenol and 2, 4-dinitrophenol adsorption. Adsorption 22, 13–21 (2016)CrossRefGoogle Scholar
  7. Chen, H.W., Chiou, C.S., Chang, S.H.: Comparison of methylparaben and propylparaben, ethylparaben adsorption onto magnetic nanoparticles with phenyl group. Powder Technol. 311, 426–431 (2017)CrossRefGoogle Scholar
  8. Daud, W.M.A.W., Ali, W.S.W.: Comparison on pore development of activated carbon produced from palm shell and coconut shell. Bioresour. Technol. 93, 63–69 (2004)CrossRefGoogle Scholar
  9. Delgado, N., Navarro, A., Marino, D., Peñuela, G.A., Ronco, A.: Surgical removal of pharmaceuticals and personal care products from domestic wastewater using rotating biological contactors. Int. J. Environ. Sci. Technol. 16, 1–10 (2018)CrossRefGoogle Scholar
  10. Foo, K.Y., Hameed, B.H.: Insights into the modeling of adsorption isotherm systems. Chem. Eng. J. 156(1), 2–10 (2010)CrossRefGoogle Scholar
  11. Giulivo, M., Alda, M.L., Capri, E., Barceló, D.: Human exposure to endocrine disrupting compounds: their role in reproductive systems, metabolic syndrome and breast cancer: a review. Environ. Res. 151, 251–264 (2016)CrossRefGoogle Scholar
  12. Gokce, Y., Aktas, Z.: Nitric acid modification of activated carbon produced from waste: tea and adsorption of methylene blue and phenol. Appl. Surf. Sci. 313, 352–359 (2014)CrossRefGoogle Scholar
  13. Jayakannan, M., Bose, J., Babourina, O., Rengel, Z., Shabala, S.: Salicylic acid in plant salinity stress signalling and tolerance. Plant Growth Regul. 76, 25–40 (2015)CrossRefGoogle Scholar
  14. Kårelid, V., Larsson, G., Björlenius, B.: Pilot-scale removal of pharmaceuticals in municipal wastewater: comparison of granular and powdered activated carbon treatment at three wastewater treatment plants. J. Environ. Manag. 193, 491–502 (2017)CrossRefGoogle Scholar
  15. Khan, M.I.R., Fatma, M., Peru, T.S., Anjum, N.A., Khan, N.A.: Salicylic acid-induced abiotic stress tolerance and underlying mechanisms in plants. Front. Plant Sci. 6, 462 (2015)Google Scholar
  16. Liu, Y.: Is the free energy change of adsorption correctly calculated? J. Chem. Eng. Released 54, 1981–1985 (2009)Google Scholar
  17. Nayak, A., Bhushan, B., Gupta, V., Sharma, P.: chemically activated carbon from lignocellulosic wastes for heavy metal wastewater remediation: effect of activation conditions. J. Colloid Interface Sci. 493, 228–240 (2017)CrossRefGoogle Scholar
  18. Nielsen, L., Bandosz, T.J.: Analysis of sulfamethoxazole and trimethoprim adsorption on sewage sludge and fish waste derived adsorbents. Microporous Mesoporous Mater. 220, 58–72 (2016)CrossRefGoogle Scholar
  19. Noh, J.S., Schwarz, J.A.: Estimation of the point of zero charge of simple oxides by mass titration. J. Colloid Interface Sci. 130, 157–164 (1989)CrossRefGoogle Scholar
  20. Pugajeva, I., Rusko, J., perkons, I., Lundanes, E., Bartkevics, V.: Determination of pharmaceutical residues in wastewater using high performance liquid chromatography coupled to quadrupole-orbitrap mass spectrometry. J. Pharm. Biomed. Anal. 133, 64–74 (2017)CrossRefGoogle Scholar
  21. Quadra, G.R., De Souza, H.O., dos Santos Costa, R., dos Santos Fernández, M.: OJ pharmaceuticals reach and affect the aquatic ecosystems in Brazil? a critical review of current studies in a developing country. Environ. Sci. Pollut. Res. 24, 1200–1218 (2017)CrossRefGoogle Scholar
  22. Savun-HekimoĞlu, B., Ince, N.H.: Reprint of: decomposition of PPCPs by ultrasound-assisted advanced Fenton reaction: a case study with salicylic acid. Ultrason. Sonochem. 40, 46–52 (2018)CrossRefGoogle Scholar
  23. Tran, H.N., Wang, Y.F., You, S.J., Chao, H.P.: Insights into the mechanism of cationic dye adsorption on activated charcoal: the importance of π-π interactions. Process. Saf. Environ. 107, 168–180 (2017)CrossRefGoogle Scholar
  24. Windsor, F.M., Ormerod, S.J., Tyler, C.R.: Endocrine disruption in aquatic systems: up-scaling research to address ecological consequences. Biol. Rev. 93, 626–641 (2018)CrossRefGoogle Scholar
  25. Wong, S., ngadi, N., inuwa, I.M., Hassan, O.: Recent advances in applications of activated carbon from biowaste for wastewater treatment: a short review. J. Clean. Prod. 175, 361–375 (2018)CrossRefGoogle Scholar
  26. Yan, B., Niu, C.H.: Adsorption behavior of norfloxacin and site energy distribution based on the Dubinin-Astakhov isotherm. Sci. Total Environ. 631, 1525–1533 (2018)CrossRefGoogle Scholar
  27. Yu, P., Wurster, D.E.: Thermodynamic estimate of the number of solvent molecules displaced by a solute molecule for Enthalpy-Driven adsorption: phenobarbital and activated carbons as the model system. J. Pharm. Sci. 107, 1055–1062 (2017)CrossRefGoogle Scholar
  28. Zhang, D., Huo, P., Liu, W.: Behavior of phenol adsorption on thermal modified activated carbon. Chin. J. Chem. Eng. 24, 446–452 (2016)CrossRefGoogle Scholar
  29. Zou, W., Cao, Y., Sun, C.: Adsorption of anionic polyacrylamide onto coal and kaolinite: changes of surface free energy components. Part. Sci. Technol. 35, 233–238 (2017)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Valentina Bernal
    • 1
  • Liliana Giraldo
    • 1
  • Juan Carlos Moreno-Piraján
    • 2
    Email author
  1. 1.Departamento de Química, Facultad de CienciasUniversidad Nacional de ColombiaBogotáColombia
  2. 2.Departamento de Química, Facultad de CienciasUniversidad de los AndesBogotáColombia

Personalised recommendations