Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter July 22, 2021

Chemical removal of m-cresol: a critical review

  • Yi Yang ORCID logo EMAIL logo , Xiyi Li , Huiqi Zhu , Xuhui Xu and Lulu Bao

Abstract

m-Cresol containing wastewater has generally become a globally environmental issue due to its refractory and high toxicity towards plants, animals and human being. The development of m-cresol related industries increases the risk of excessive m-cresol discharge, making high efficiency methods to treat m-cresol an urgent topic in both economic and environmental aspects. This review focuses on the chemical treatment methods of m-cresol wastewater, including chemical adsorption, photocatalytic degradation, electrocatalytic degradation and catalytic wet oxidation. The efficiency, cost and process optimization of different methods are discussed in detail. Chemical adsorption is convenient but has relatively low efficiency. Photocatalytic degradation is an easily operated technology with high efficiency, but the selection of catalyst is too limited and the cost of light source is relatively high. Electrocatalytic degradation is time-saving but energy-intensive, and operational difficulty brings a barrier to industrialization. Catalytic wet oxidation (CWO) is highly effective and easily modified, but the performance and stability of catalysts are still very moderate. Following this, the selection and application of different methods regarding the requirement of actual environment are analyzed. Finally, a perspective on the opportunities and development for efficient m-cresol removal method is given.


Corresponding author: Yi Yang, College of Education for the Future, Beijing Normal University, Zhuhai 519087, P. R. China, E-mail:

Funding source: Beijing Normal University 10.13039/501100002726

Award Identifier / Grant number: 29100-111032105

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: YY gratefully acknowledges the financial support from Beijing Normal University under the grant 29100-111032105.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

Abdollahi, Y., Zakaria, A., and Sairi, N.A. (2014). Degradation of high level m-cresol by zinc oxide as photocatalyst. Clean 42: 1292–1297, https://doi.org/10.1002/clen.201300451.Search in Google Scholar

Adishkumar, S. and Kanmani, S. (2012). Degradation of phenolic wastewaters by solar/TiO2 and solar/TiO2/H2O2 processes. Int. J. Environ. Waste Manag. 1–2: 169–180, https://doi.org/10.1504/ijewm.2012.044167.Search in Google Scholar

Ahamad, P.Y.A. and Kunhi, A.A.M. (1999). Degradation of high concentrations of cresols by Pseudomonas sp. CP4. World J. Microbiol. Biotechnol. 15: 321–323, https://doi.org/10.1023/a:1008821120432.10.1023/A:1008821120432Search in Google Scholar

Ahmed, S., Rasul, M.G., Martens, W.N., Brown, R., and Hashib, M.A. (2010). Heterogeneous photocatalytic degradation of phenols in wastewater: a review on current status and developments. Desalination 261: 3–18, https://doi.org/10.1016/j.desal.2010.04.062.Search in Google Scholar

Alfaya, E., Iglesias, O., Pazos, M., and Sanromán, M.A. (2015). Environmental application of an industrial waste as catalyst for the electro-Fenton-like treatment of organic pollutants. RSC Adv. 5: 14416–14424, https://doi.org/10.1039/c4ra15934a.Search in Google Scholar

Amen-Chen, C., Pakdel, H., and Roy, C. (1997). Separation of phenols from Eucalyptus wood tar. Biomass Bioenergy 13: 25–37, https://doi.org/10.1016/s0961-9534(97)00021-4.Search in Google Scholar

Araña, J., Melian, E.P., Lopez, V.M.R., Alonso, A.P., Rodriguez, J.M.D., Diaz, O.G., and Pena, J.P. (2007a). Photocatalytic degradation of phenol and phenolic compounds. Part I. Adsorption and FTIR study. J. Hazard Mater. 146: 520–528, https://doi.org/10.1016/j.jhazmat.2007.04.066.Search in Google Scholar

Araña, J., Rodríguez López, V.M., Pulido Melián, E., Suárez Reyes, M.I., Doña Rodríguez, J.M., and González Díaz, O. (2007b). Comparative study of phenolic compounds mixtures. Catal. Today 129: 177–184, https://doi.org/10.1016/j.cattod.2007.06.063.Search in Google Scholar

Aviam, O., Bar-Nes, G., Zeiri, Y., and Sivan, A. (2004). Accelerated biodegradation of cement by sulfur-oxidizing bacteria as a bioassay for evaluating immobilization of low-level radioactive waste. Appl. Environ. Microbiol. 70: 6031–6036, https://doi.org/10.1128/aem.70.10.6031-6036.2004.Search in Google Scholar

Balsama, S., Beltrame, P., Beltrame, P.L., Carniti, P., Forni, L., and Zuretti, G. (1984). Alkylation of phenol with methanol over zeolites. Appl. Catal. 13: 161–170, https://doi.org/10.1016/s0166-9834(00)83334-5.Search in Google Scholar

Barge, A.S. and Vaidya, P.D. (2018). Wet air oxidation of cresylic spent caustic – a model compound study over graphene oxide (GO) and ruthenium/GO catalysts. J. Environ. Manag. 212: 479–489, https://doi.org/10.1016/j.jenvman.2018.01.066.Search in Google Scholar PubMed

Barge, A.S. and Vaidya, P.D. (2019). Ruthenium-decorated carbon nanotubes as catalyst for wet air oxidation. J. Environ. Chem. Eng. 7: 102914, https://doi.org/10.1016/j.jece.2019.102914.Search in Google Scholar

Bounab, L., Iglesias, O., González-Romero, E., Pazos, M., and Sanromán, M.Á. (2019). Effective heterogeneous electro-Fenton process of m -cresol with iron loaded actived carbon. RSC Adv. 5: 31049–31056.10.1039/C5RA03050ASearch in Google Scholar

Bounab, L., Iglesias, O., Pazos, M., Sanromán, M.Á., and González-Romero, E. (2016). Effective monitoring of the electro-Fenton degradation of phenolic derivatives by differential pulse voltammetry on multi-walled-carbon nanotubes modified screen-printed carbon electrodes. Appl. Catal. B Environ. 180: 544–550, https://doi.org/10.1016/j.apcatb.2015.07.011.Search in Google Scholar

Brillas, E. and Martínez-Huitle, C.A. (2015). Decontamination of wastewaters containing synthetic organic dyes by electrochemical methods. An updated review. Appl. Catal. B Environ. 166–167: 603–643, https://doi.org/10.1016/j.apcatb.2014.11.016.Search in Google Scholar

Brillas, E., Sire S, I., and Oturan, M.A. (2009). Electro-Fenton process and related electrochemical technologies based on Fenton’s reaction chemistry. Chem. Rev. 109: 6570, https://doi.org/10.1021/cr900136g.Search in Google Scholar PubMed

Chaplin, B.P. (2014). Critical review of electrochemical advanced oxidation processes for water treatment applications. Environ. Sci.: Process. Impact 16: 1182–1203, https://doi.org/10.1039/c3em00679d.Search in Google Scholar PubMed

Chaplin, B.P., Schrader, G., and Farrell, J. (2010). Electrochemical destruction of N-nitrosodimethylamine in reverse osmosis concentrates using Boron-doped diamond film electrodes. Environ. Sci. Technol. 44: 4264, https://doi.org/10.1021/es903872p.Search in Google Scholar PubMed

Chen, C., Chen, G., Yang, F., Wang, H., and Han, J. (2015). Vapor phase hydrodeoxygenation and hydrogenation of m-cresol on silica supported Ni, Pd and Pt catalysts. Chem. Eng. Sci. 135: 145–154, https://doi.org/10.1016/j.ces.2015.04.054.Search in Google Scholar

Chen, D., Liu, F., Zong, L., Sun, X., Zhang, X., Zhu, C., Tao, X., and Li, A. (2016). Integrated adsorptive technique for efficient recovery of m-cresol and m-toluidine from actual acidic and salty wastewater. J. Hazard Mater. 312: 192–199, https://doi.org/10.1016/j.jhazmat.2016.03.056.Search in Google Scholar PubMed

Chen, W., Zou, C., Li, X., and Li, L. (2016). The treatment of phenolic contaminants from shale gas drilling wastewater: a comparison with UV-Fenton and modified UV-Fenton processes at neutral pH. RSC Adv. 6: 90682–90689, https://doi.org/10.1039/c6ra18662a.Search in Google Scholar

Cho, S.I., Kim, D.S., and Woo, S.I. (1997). Wet oxidation of wastewater containing hydrocarbons by novel supported Pd catalysts. Kor. J. Chem. Eng. 14: 479–485, https://doi.org/10.1007/bf02706596.Search in Google Scholar

Chu, Y., Zhang, D., Liu, L., Qian, Y., and Li, L. (2013). Electrochemical degradation of m-cresol using porous carbon-nanotube-containing cathode and Ti/SnO2–Sb2O5–IrO2 anode: kinetics, byproducts and biodegradability. J. Hazard Mater. 252–253: 306–312, https://doi.org/10.1016/j.jhazmat.2013.03.018.Search in Google Scholar PubMed

Das, M. and Bhattacharyya, K.G. (2013). Oxidative degradation of orange II dye in water with raw and acid-treated ZnO, and MnO2. Clean 41: 984–991, https://doi.org/10.1002/clen.201200341.Search in Google Scholar

Dirany, A., Sires, I., Oturan, N., Oezcan, A., and Oturan, M.A. (2012). Electrochemical treatment of sulfachloropyridazine: kinetics, reaction pathways, and toxicity evolution. Environ. Sci. Technol. 46: 4074, https://doi.org/10.1021/es204621q.Search in Google Scholar PubMed

Dos Reis, G.S., Adebayo, M.A., Sampaio, C.H., Lima, E.C., Thue, P.S., De Brum, I.A.S., Dias, S.L.P., and Pavan, F.A. (2017). Removal of phenolic compounds from aqueous solutions using sludge-based activated carbons prepared by conventional heating and microwave-assisted pyrolysis. Water Air Soil Pollut. 228: 33, https://doi.org/10.1007/s11270-016-3202-7.Search in Google Scholar

El-Ghenymy, A., Arias, C., Cabot, P.L., Centellas, F., Garrido, J.A., Rodríguez, R.M., and Brillas, E. (2012). Electrochemical incineration of sulfanilic acid at a boron-doped diamond anode. Chemosphere 87: 1126–1133, https://doi.org/10.1016/j.chemosphere.2012.02.006.Search in Google Scholar PubMed

Feng, L., Oturan, N., van Hullebusch, E.D., Esposito, G., and Oturan, M.A. (2014). Degradation of anti-inflammatory drug ketoprofen by electro-oxidation: comparison of electro-Fenton and anodic oxidation processes. Environ. Sci. Pollut. Res. 21: 8406–8416, https://doi.org/10.1007/s11356-014-2774-2.Search in Google Scholar PubMed

Flox, C., Cabot, P., Centellas, F., Garrido, J.A., Rodríguez, R.M., Arias, C., and Brillas, E. (2007). Solar photoelectro-Fenton degradation of cresols using a flow reactor with a boron-doped diamond anode. Appl. Catal. B Environ. 75: 17–28, https://doi.org/10.1016/j.apcatb.2007.03.010.Search in Google Scholar

Flox, C., Arias, C., Brillas, E., Savall, A., and Groenen-Serrano, K. (2009). Electrochemical incineration of cresols: a comparative study between PbO2 and boron-doped diamond anodes. Chemosphere 74: 1340–1347, https://doi.org/10.1016/j.chemosphere.2008.11.050.Search in Google Scholar PubMed

Flox, C., Brillas, E., Savall, A., and Groenen-Serrano, K. (2012). Kinetic study of the electrochemical mineralization of m-cresol on a boron-doped diamond anode. Curr. Org. Chem. 16: 1960–1966, https://doi.org/10.2174/138527212803251712.Search in Google Scholar

García, O., Isarain-Chávez, E., El-Ghenymy, A., Brillas, E., and Peralta-Hernández, J.M. (2014). Degradation of 2,4-D herbicide in a recirculation flow plant with a Pt/air-diffusion and a BDD/BDD cell by electrochemical oxidation and electro-Fenton process. J. Electroanal. Chem. 728: 1–9, https://doi.org/10.1016/j.jelechem.2014.06.019.Search in Google Scholar

Gogate, P.R. and Pandit, A.B. (2004). A review of imperative technologies for wastewater treatment I: oxidation technologies at ambient conditions. Adv. Environ. Res. 8: 501–551, https://doi.org/10.1016/s1093-0191(03)00032-7.Search in Google Scholar

Gupta, V.K., Suhas, Ali, I., and Saini, V.K. (2004). Removal of rhodamine B, fast green, and methylene blue from wastewater using red mud, an aluminum industry waste. Ind. Eng. Chem. Res. 43: 1740–1747, https://doi.org/10.1021/ie034218g.Search in Google Scholar

Gupta, V.K., Mittal, A., Jain, R., Mathur, M., and Sikarwar, S. (2006a). Adsorption of Safranin-T from wastewater using waste materials— activated carbon and activated rice husks. J. Colloid Interface Sci. 303: 80–86, https://doi.org/10.1016/j.jcis.2006.07.036.Search in Google Scholar PubMed

Gupta, V.K., Mittal, A., Kurup, L., and Mittal, J. (2006b). Adsorption of a hazardous dye, erythrosine, over hen feathers. J. Colloid Interface Sci. 304: 52–57, https://doi.org/10.1016/j.jcis.2006.08.032.Search in Google Scholar PubMed

Han, Y., Quan, X., Chen, S., Wang, S., and Zhang, Y. (2007). Electrochemical enhancement of adsorption capacity of activated carbon fibers and their surface physicochemical characterizations. Electrochim. Acta 52: 3075–3081, https://doi.org/10.1016/j.electacta.2006.09.059.Search in Google Scholar

Hatipo Lu, A., San, N., and Nar, Z. (2004). An experimental and theoretical investigation of the photocatalytic degradation of meta-cresol in TiO 2 suspensions: a model for the product distribution. J. Photochem. Photobiol. Chem. 165: 119–129.10.1016/j.jphotochem.2004.03.008Search in Google Scholar

Henam, S.D., Thiyam, D.S., and Nongmaithem, R.S. (2016). Degradation and mechanism of m-cresol by silver nanoparticles synthesized using night jasmine (Nyctanthes arbor-tristis) extracts through ultrasonic-assisted approach. Environ. Eng. Sci. 34: 433–442.10.1089/ees.2016.0348Search in Google Scholar

Hering, J.G., Waite, T.D., Luthy, R.G., Drewes, J.E., and Sedlak, D.L. (2013). A changing framework for urban water systems. Environ. Sci. Technol. 47: 10721–10726, https://doi.org/10.1021/es4007096.Search in Google Scholar PubMed

Herrmann, J., Disdier, J., Pichat, P., Malato, S., and Blanco, J. (1998). TiO2-based solar photocatalytic detoxification of water containing organic pollutants. Case studies of 2,4-dichlorophenoxyaceticacid (2,4-D) and of benzofuran. Appl. Catal. B Environ. 17: 15–23, https://doi.org/10.1016/s0926-3373(97)00098-2.Search in Google Scholar

Hu, M.Z., Shi, Z.H., and Zhao, H.Y. (2013). Study on treatment of m-cresol wastewater using potassium ferrate(VI). Adv. Mater. Res. 610-613: 2367–2371.10.4028/www.scientific.net/AMR.610-613.2367Search in Google Scholar

Huang, C. and Huang, Y. (2009). Application of an active immobilized iron oxide with catalytic H2O2 for the mineralization of phenol in a batch photo-fluidized bed reactor. Appl. Catal. Gen. 357: 135–141, https://doi.org/10.1016/j.apcata.2008.12.043.Search in Google Scholar

Hussain, A., Kumar, P., and Mehrotra, I. (2008). Treatment of phenolic wastewater in UASB reactor: effect of nitrogen and phosphorous. Bioresour. Technol. 99: 8497–8503, https://doi.org/10.1016/j.biortech.2008.03.059.Search in Google Scholar

Iniesta, J., Michaud, P.A., Panizza, M., and Comninellis, C. (2001). Electrochemical oxidation of 3-methylpyridine at a boron-doped diamond electrode: application to electroorganic synthesis and wastewater treatment. Electrochem. Commun. 3: 346–351, https://doi.org/10.1016/s1388-2481(01)00174-6.Search in Google Scholar

Jaramillo-Sierra, B., Mercado-Cabrera, A., López-Callejas, R., Pe A-Eguiluz, R., Barocio, S.R., Valencia-Alvarado, R., Rodríguez-Méndez, B., Mu Oz-Castro, A., and De, L.P.A. (2012). Degradation of m-cresol in aqueous solution by dielectric barrier discharge. Journal of Physics Conference 406: 12025, https://doi.org/10.1088/1742-6596/406/1/012025.Search in Google Scholar

Jiang, B., Shi, S., Song, L., Tan, L., Li, M., Liu, J., and Xue, L. (2016). Efficient treatment of phenolic wastewater with high salinity using a novel integrated system of magnetically immobilized cells coupling with electrodes. Bioresour. Technol. 218: 108–114, https://doi.org/10.1016/j.biortech.2016.06.080.Search in Google Scholar PubMed

Jiao, T., Gong, M., Zhuang, X., Li, C., and Zhang, S. (2015). A new separation method for phenolic compounds from low-temperature coal tar with urea by complex formation. J. Ind. Eng. Chem. 29: 344–348, https://doi.org/10.1016/j.jiec.2015.04.013.Search in Google Scholar

Jie, B., Loh, G., Gwie, C.G., Dewiyanti, S., Tasrif, M., and Borgna, A. (2011). Desulfurization of diesel fuels by selective adsorption on activated carbons: competitive adsorption of polycyclic aromatic sulfur heterocycles and polycyclic aromatic hydrocarbons. Chem. Eng. J. 166: 207–217.10.1016/j.cej.2010.10.063Search in Google Scholar

Kanmani, S., Thanasekaran, K., and Dieter, B. (2016). Studies on decolorization of textile dyeing rinse wastewaters in solar photocatalytic reactors. J. Adv. Oxid. Technol. 6: 166–175.10.1515/jaots-2003-0206Search in Google Scholar

Karr, C., Brown, P.M., Estep, P.A., and Humphrey, G.L. (1958). Identification and determination of low-boiling phenols in low temperature coal tar. Anal. Chem. 30: 1413–1416, https://doi.org/10.1021/ac60140a037.Search in Google Scholar

Karthikeyan, S. and Gopalakrishnan, A.N. (2011). Degradation of phenol and m-cresol in aqueous solutions using indigenously developed microwave-ultraviolet reactor. J. Sci. Ind. Res. 70: 71–76.Search in Google Scholar

Karthikeyan, S., Sekaran, G., and Gupta, V.K. (2013). Nanoporous activated carbon fluidized bed catalytic oxidations of aqueous o, p and m-cresols: kinetic and thermodynamic studies. Environ. Sci. Pollut. Res. 20: 4790–4806, https://doi.org/10.1007/s11356-012-1380-4.Search in Google Scholar

Kavitha, V. and Palanivelu, K. (2005). Destruction of cresols by Fenton oxidation process. Water Res. 39: 3062–3072, https://doi.org/10.1016/j.watres.2005.05.011.Search in Google Scholar

Kennedy, L.J., Vijaya, J.J., Sekaran, G., and Kayalvizhi, K. (2007). Equilibrium, kinetic and thermodynamic studies on the adsorption of m-cresol onto micro- and mesoporous carbon. J. Hazard Mater. 149: 134–143, https://doi.org/10.1016/j.jhazmat.2007.03.061.Search in Google Scholar

Kudo, A. and Miseki, Y. (2009). Heterogeneous photocatalyst materials for water splitting. Chem. Soc. Rev. 38: 253–278, https://doi.org/10.1039/B800489G.Search in Google Scholar

Lee, L.S., Lin, C.W., and Kao, C.H. (2000). Using tert-butyl alcohol as an adductive agent for separation of an m-cresol and 2,6-xylenol mixture. Ind. Eng. Chem. Res. 39: 2068–2075, https://doi.org/10.1021/ie990759n.Search in Google Scholar

Li, X., Wang, J., Rykov, A.I., Sharma, V.K., Wei, H., Jin, C., Liu, X., Li, M., Yu, S., Sun, C., and Dionysiou, D.D. (2015). Prussian blue/TiO2 nanocomposites as a heterogeneous photo-Fenton catalyst for degradation of organic pollutants in water. Catal. Sci. Technol. 5: 504–514, https://doi.org/10.1039/c4cy00947a.Search in Google Scholar

Li, X., Yu, J., and Jaroniec, M. (2016). Hierarchical photocatalysts. Chem. Soc. Rev. 45: 2603–2636, https://doi.org/10.1039/C5CS00838G.Search in Google Scholar

Lin, S. and Juang, R. (2009). Adsorption of phenol and its derivatives from water using synthetic resins and low-cost natural adsorbents: a review. J. Environ. Manag. 90: 1336–1349, https://doi.org/10.1016/j.jenvman.2008.09.003.Search in Google Scholar

Lin, C.H. and Yang, J.Y. (1992). Chemical burn with cresol intoxication and multiple organ failure. Burns 18: 162–166, https://doi.org/10.1016/0305-4179(92)90019-q.Search in Google Scholar

Liu, P., He, S., Wei, H., Wang, J., and Sun, C. (2015a). Characterization of α-Fe2O3/γ-Al2O3 catalysts for catalytic wet peroxide oxidation of m-cresol. Ind. Eng. Chem. Res. 54: 130–136, https://doi.org/10.1021/ie5037897.Search in Google Scholar

Liu, P., Wei, H., He, S., and Sun, C. (2015b). Catalytic wet peroxide oxidation of m-cresol over Fe/γ-Al2O3 and Fe-Ce/γ-Al2 O3. Chem. Pap. 69: 827–838, https://doi.org/10.1515/chempap-2015-0028.Search in Google Scholar

Liu, W., Duan, P., Hu, X., Gao, J., and Zhou, F. (2019a). Fabrication of efficient nano-MnOx/ACF particle electrodes and their application in the electrooxidation of m-cresol in the 3-D electrode system. Ind. Eng. Chem. Res. 58: 22114–22123, https://doi.org/10.1021/acs.iecr.9b04234.Search in Google Scholar

Liu, W., Hu, X., Sun, Z., and Duan, P. (2019b). Electrochemical modification of activated carbon fiber as 3-D particle electrodes: characterization and enhancement for the degradation of m-cresol. Environ. Sci. Pollut. Res. 26: 16433–16448, https://doi.org/10.1007/s11356-019-04979-5.Search in Google Scholar

Marczewski, M., Bodibo, J., Perot, G., and Guisnet, M. (1989). Alkylation of aromatics: Part I. Reaction network of the alkylation of phenol by methanol on ushy zeolite. J. Mol. Catal. 50: 211–218, https://doi.org/10.1016/0304-5102(89)85064-3.Search in Google Scholar

Marissa, C., Wudneh, S., Jerald, L., and Saravanan, S. (2014). Photocatalytic degradation of phenol and phenol derivatives using a nano-TiO2 catalyst: integrating quantitative and qualitative factors using response surface methodology. Water-Sui 6: 1785–1806.Search in Google Scholar

Martínez-Huitle, C.A., Rodrigo, M.A., Sirés, I., and Scialdone, O. (2015). Single and coupled electrochemical processes and reactors for the abatement of organic water pollutants: a critical review. Chem. Rev. 115: 13362–13407, https://doi.org/10.1021/acs.chemrev.5b00361.Search in Google Scholar PubMed

Mascia, M., Vacca, A., Polcaro, A.M., Palmas, S., Ruiz, J.R., and Pozzo, A.D. (2010). Electrochemical treatment of phenolic waters in presence of chloride with boron-doped diamond (BDD) anodes: experimental study and mathematical model. J. Hazard Mater. 174: 314–322, https://doi.org/10.1016/j.jhazmat.2009.09.053.Search in Google Scholar PubMed

Melián, E.P., Díaz, O.G., Araña, J., Rodríguez, J.M.D., Rendón, E.T., and Melián, J.A.H. (2007). Kinetics and adsorption comparative study on the photocatalytic degradation of o-, m- and p-cresol. Catal. Today 129: 256–262, https://doi.org/10.1016/j.cattod.2007.08.003.Search in Google Scholar

Mohammadi, M., Sabbaghi, S., Sadeghi, H., Zerafat, M.M., and Pooladi, R. (2016). Preparation and characterization of TiO2/ZnO/CuO nanocomposite and application for phenol removal from wastewaters. Desalination Water Treat. 57: 799–809, https://doi.org/10.1080/19443994.2014.968877.Search in Google Scholar

Nakata, K. and Fujishima, A. (2012). TiO2 photocatalysis: design and applications. J. Photochem. Photobiol. C Photochem. Rev. 13: 169–189, https://doi.org/10.1016/j.jphotochemrev.2012.06.001.Search in Google Scholar

Ncanana, Z.S. and Pullabhotla, V.S.R.R. (2018). Ozone initiated oxidation of cresol isomers using γ-Al2O3 and SiO2 as adsorbents. Catal. Lett. 148: 1535–1546, https://doi.org/10.1007/s10562-018-2360-1.Search in Google Scholar

Ncanana, Z.S. and Pullabhotla, V.S.R.R (2019). Oxidative degradation of m-cresol using ozone in the presence of pure γ-Al2O3, SiO2 and V2O5 catalysts. J. Environ. Chem. Eng. 7: 103072, https://doi.org/10.1016/j.jece.2019.103072.Search in Google Scholar

Nie, L., and Resasco, D.E. (2014). Kinetics and mechanism of m-cresol hydrodeoxygenation on a Pt/SiO_2 catalyst. J. Catal. 317: 22–29, https://doi.org/10.1016/j.jcat.2014.05.024.Search in Google Scholar

Pacheco, M.J., Morão, A., Lopes, A., Ciríaco, L., and Gonçalves, I. (2008). Degradation of phenols using boron-doped diamond electrodes: a method for quantifying the extent of combustion. Electrochim. Acta 53: 629–636.10.1016/j.electacta.2007.07.024Search in Google Scholar

Pang, K., Hou, Y., Wu, W., Guo, W., Peng, W., and Marsh, K.N. (2012). Efficient separation of phenols from oils via forming deep eutectic solvents. Green Chem. 14: 2398–2401, https://doi.org/10.1039/c2gc35400d.Search in Google Scholar

Panizza, M. and Cerisola, G. (2009). Direct and mediated anodic oxidation of organic pollutants. Chem. Rev. 109: 6541–6569, https://doi.org/10.1021/cr9001319.Search in Google Scholar

Park, S., Park, B., and Ryu, S. (1999). Electrochemical treatment on activated carbon fibers for increasing the amount and rate of Cr(VI) adsorption. Carbon 37: 1223–1226, https://doi.org/10.1016/s0008-6223(98)00318-2.Search in Google Scholar

Parra, S., Malato, S., and Pulgarin, C. (2002). New integrated photocatalytic-biological flow system using supported TiO2 and fixed bacteria for the mineralization of isoproturon. Appl. Catal. B Environ. 36: 131–144, https://doi.org/10.1016/s0926-3373(01)00293-4.Search in Google Scholar

Peijuan, L., Huangzhao, W., Ruiping, Q., Songbo, H., and Chenglin, S. (2013). Catalytic wet peroxide oxidation of m-cresol wastewater over Fe/γ-Al2O3 catalysts. Environ. Chem. 32: 2121–2126.Search in Google Scholar

Peiró, A.M., Ayllón, J.A., Peral, J., and Doménech, X. (2001). TIO2-photocatalyzed degradation of phenol and ortho-substituted phenolic compounds. Appl. Catal. B Environ. 30: 359–373, https://doi.org/10.1016/s0926-3373(00)00248-4.Search in Google Scholar

Pera-Titus, M., A-Molina, V.G., Ba Os, M.A., Gimnez, J., and Esplugas, S. (2004). Degradation of chlorophenols by means of advanced oxidation processes: a general review. Appl. Catal. B Environ. 47: 219–256, https://doi.org/10.1016/j.apcatb.2003.09.010.Search in Google Scholar

Qureshi, T., Memon, N., Memon, S.Q., and Ashraf, M.A. (2016). Decontamination of ofloxacin: optimization of removal process onto sawdust using response surface methodology. Desalination Water Treat. 57: 221–229.10.1080/19443994.2015.1006825Search in Google Scholar

Rahmani, A., Hadi, R., and Somayeh, B. (2019). Photocatalytic degradation of phenolic compound (Phenol, resorcinol and cresol) by titanium dioxide photocatalyst on ordered mesoporous carbon (CMK-3) support under UV irradiation. Desalination Water Treat. 144: 224–232, https://doi.org/10.5004/dwt.2019.23673.Search in Google Scholar

Rajkumar, D. and Palanivelu, K. (2003). Electrochemical degradation of cresols for wastewater treatment. Ind. Eng. Chem. Res. 42: 141–151, https://doi.org/10.1021/ie020759e.Search in Google Scholar

Rajkumar, D., Palanivelu, K., and Balasubramanian, N. (2005). Combined electrochemical degradation and activated carbon adsorption treatments for wastewater containing mixed phenolic compounds. J. Environ. Eng. Sci. 4: 1–9, https://doi.org/10.1139/s04-037.Search in Google Scholar

Sad, M.E., Padró, C.L., and Apesteguía, C.R. (2008). Synthesis of cresols by alkylation of phenol with methanol on solid acids. Catal. Today 133–135: 720–728, https://doi.org/10.1016/j.cattod.2007.12.074.Search in Google Scholar

Sanders, J.M., Bucher, J.R., Peckham, J.C., Kissling, G.E., and Chhabra, R.S. (2009). Carcinogenesis studies of cresols in rats and mice. Toxicology 257: 33–39, https://doi.org/10.1016/j.tox.2008.12.005.Search in Google Scholar

Santacesaria, E., Grasso, D., Gelosa, D., and Carrá, S. (1990). Catalytic alkylation of phenol with methanol: factors influencing activities and selectivities: I. Effect of different acid sites evaluated by studying the behaviour of the catalysts: γ-alumina, nafion-H, silica-alumina and phosphoric acid. Appl. Catal. 64: 83–99, https://doi.org/10.1016/s0166-9834(00)81555-9.Search in Google Scholar

Seraghni, N., Belattar, S., Mameri, Y., Debbache, N., and Sehili, T. (2012). Fe(III)-citrate-complex-induced photooxidation of 3-methylphenol in aqueous solution. Int. J. Photoenergy 2012: 630425, https://doi.org/10.1155/2012/630425.Search in Google Scholar

Seredych, M., Lison, J., Jans, U., and Bandosz, T.J. (2009). Textural and chemical factors affecting adsorption capacity of activated carbon in highly efficient desulfurization of diesel fuel. Carbon 47: 2491–2500, https://doi.org/10.1016/j.carbon.2009.05.001.Search in Google Scholar

Shi, R., Zhao, Y., Waterhouse, G.I.N., Zhang, S., and Zhang, T. (2019). Defect engineering in photocatalytic nitrogen fixation. ACS Catal. 9: 9739–9750, https://doi.org/10.1021/acscatal.9b03246.Search in Google Scholar

Sirés, I., Brillas, E., Oturan, M.A., Rodrigo, M.A., and Panizza, M. (2014). Electrochemical advanced oxidation processes: today and tomorrow. A review. Environ. Sci. Pollut. Res. 21: 8336–8367, https://doi.org/10.1007/s11356-014-2783-1.Search in Google Scholar PubMed

Sun, W.-J., Wang, Y.-M., Wei, H.-Z., Wang, S., Li, X.-N., Li, J.-M., Sun, C., and An, L.-Y. (2015). Degradation of m-cresol with Fe-MCM- 41 in catalytic ozonation. J. Environ. Sci. 36: 1345–1351.Search in Google Scholar

Tan, X., Ma, L., Han, P., Wei, H., and Sun, C. (2020). Fabrication of boron-doped diamond films electrode for efficient electrocatalytic degradation of cresols. Chemosphere 246: 125786, https://doi.org/10.1016/j.chemosphere.2019.125786.Search in Google Scholar PubMed

Tao, Y., Ai-Li, Z., and Ji-Ti, Z. (2009). Characteristics of adsorption and desorption isotherm of cresol isomers on activated carbon. Environ. Sci. 30: 1744–1748.Search in Google Scholar

Ton, S., Chang, S., Hsu, L., Wang, M., and Wang, K. (2012). Evaluation of acute toxicity and teratogenic effects of disinfectants by Daphnia magna embryo assay. Environ. Pollut. 168: 54–61, https://doi.org/10.1016/j.envpol.2012.04.008.Search in Google Scholar PubMed

Trellu, C., Mousset, E., Pechaud, Y., Huguenot, D., van Hullebusch, E.D., Esposito, G., and Oturan, M.A. (2016). Removal of hydrophobic organic pollutants from soil washing/flushing solutions: a critical review. J. Hazard Mater. 306: 149–174, https://doi.org/10.1016/j.jhazmat.2015.12.008.Search in Google Scholar PubMed

Valsania, M.C., Fasano, F., Richardson, S.D., and Vincenti, M. (2012). Investigation of the degradation of cresols in the treatments with ozone. Water Res. 46: 2795–2804, https://doi.org/10.1016/j.watres.2012.02.040.Search in Google Scholar PubMed

Venditti, F., Cuomo, F., Ceglie, A., Avino, P., Russo, M.V., and Lopez, F. (2015). Visible light caffeic acid degradation by carbon-doped titanium dioxide. Langmuir 31: 3627–3634, https://doi.org/10.1021/acs.langmuir.5b00560.Search in Google Scholar PubMed

Venter, D.L. and Nieuwoudt, I. (1998). Separation of m-cresol from neutral oils with liquid-liquid extraction. Ind. Eng. Chem. Res. 37: 4099–4106, https://doi.org/10.1021/ie980147n.Search in Google Scholar

Vidic, R.D., Suidan, M.T., and Brenner, R.C. (1993). Oxidative coupling of phenols on activated carbon: impact on adsorption equilibrium. Environ. Sci. Technol. 27: 2079–2085, https://doi.org/10.1021/es00047a013.Search in Google Scholar

Vörösmarty, C.J., Mcintyre, P.B., Gessner, M.O., Dudgeon, D., Prusevich, A., Green, P., Glidden, S., Bunn, S.E., Sullivan, C.A., Liermann, C.R., and Davies, P.M. (2010). Global threats to human water security and river biodiversity. Nature 467: 555–561, https://doi.org/10.1038/nature09440.Search in Google Scholar PubMed

Wang, Q. and Domen, K. (2020). Particulate photocatalysts for light-driven water splitting: mechanisms, challenges, and design strategies. Chem. Rev. 120: 919–985, https://doi.org/10.1021/acs.chemrev.9b00201.Search in Google Scholar PubMed

Wang, K., Hsieh, Y., and Chen, L. (1998). The heterogeneous photocatalytic degradation, intermediates and mineralization for the aqueous solution of cresols and nitrophenols. J. Hazard Mater. 59: 251–260, https://doi.org/10.1016/s0304-3894(97)00151-9.Search in Google Scholar

Wang, Y., Li, X., Zhen, L., Zhang, H., Zhang, Y., and Wang, C. (2012). Electro-Fenton treatment of concentrates generated in nanofiltration of biologically pretreated landfill leachate. J. Hazard Mater. 229–230: 115–121, https://doi.org/10.1016/j.jhazmat.2012.05.108.Search in Google Scholar PubMed

Wang, W., Song, J., and Han, X. (2013). Schwertmannite as a new Fenton-like catalyst in the oxidation of phenol by H2O2. J. Hazard Mater. 262: 412–419, https://doi.org/10.1016/j.jhazmat.2013.08.076.Search in Google Scholar PubMed

Wang, Y., Liu, Y., Wang, K., Song, S., Tsiakaras, P., and Liu, H. (2015). Preparation and characterization of a novel KOH activated graphite felt cathode for the electro-Fenton process. Appl. Catal. B Environ. 165: 360–368, https://doi.org/10.1016/j.apcatb.2014.09.074.Search in Google Scholar

Wang, Y., Wei, H., Zhao, Y., Sun, W., and Sun, C. (2017a). Low temperature modified sludge-derived carbon catalysts for efficient catalytic wet peroxide oxidation of m-cresol. Green Chem. 19: 1362–1370, https://doi.org/10.1039/c6gc03001g.Search in Google Scholar

Wang, Y., Wei, H., Zhao, Y., Sun, W., and Sun, C. (2017b). The optimization, kinetics and mechanism of m-cresol degradation via catalytic wet peroxide oxidation with sludge-derived carbon catalyst. J. Hazard Mater. 326: 36–46, https://doi.org/10.1016/j.jhazmat.2016.12.014.Search in Google Scholar PubMed

Wang, Y., Suzuki, H., Xie, J., Tomita, O., Martin, D.J., Higashi, M., Kong, D., Abe, R., and Tang, J. (2018). Mimicking natural photosynthesis: solar to renewable H2 fuel synthesis by Z-scheme water splitting systems. Chem. Rev. 118: 5201–5241, https://doi.org/10.1021/acs.chemrev.7b00286.Search in Google Scholar PubMed PubMed Central

Yang, Y., Zhang, H., and Yan, Y. (2018a). The preparation of Fe2O3-ZSM-5 catalysts by metal-organic chemical vapour deposition method for catalytic wet peroxide oxidation of m-cresol. Roy. Soc. Open Sci. 5: 171731, https://doi.org/10.1098/rsos.171731.Search in Google Scholar PubMed PubMed Central

Yang, Y., Zhang, H., and Yan, Y. (2018b). Synthesis of carbon nanotube on stainless steel microfibrous composite—comparison of direct and indirect growth and its application in fixed bed m-cresol adsorption. Chem. Eng. Res. Des. 139: 162–173, https://doi.org/10.1016/j.cherd.2018.09.027.Search in Google Scholar

Yang, Y., Zhang, H., and Yan, Y. (2018c). Catalytic wet peroxide oxidation of m‐cresol over novel Fe2O3 loaded microfibrous entrapped CNT composite catalyst in a fixed‐bed reactor. J. Chem. Technol. Biotechnol. 93: 2552–2563, https://doi.org/10.1002/jctb.5609.Search in Google Scholar

Yang, Y., Zhang, H., and Yan, Y. (2019a). Synthesis of CNTs on stainless steel microfibrous composite by CVD: effect of synthesis condition on carbon nanotube growth and structure. Compos. B Eng. 160: 369–383, https://doi.org/10.1016/j.compositesb.2018.12.100.Search in Google Scholar

Yang, Y., Zhang, H., and Yan, Y. (2019b). Preparation of novel iron-loaded microfibers entrapped carbon-nanotube composites for catalytic wet peroxide oxidation of m-cresol in a fixed bed reactor. Separ. Purif. Technol. 212: 405–415, https://doi.org/10.1016/j.seppur.2018.11.050.Search in Google Scholar

Yang, Y., Koh, K.Y., Li, R., Zhang, H., Yan, Y., and Chen, J.P. (2020a). An innovative lanthanum carbonate grafted microfibrous composite for phosphate adsorption in wastewater. J Hazard Mater 392: 121952.10.1016/j.jhazmat.2019.121952Search in Google Scholar PubMed

Yang, Y., Yan, Y., Zhang, H., and Wu, X. (2020b). Catalytic wet peroxide oxidation of phenol on Fe-ZSM-5/PSSF membrane catalysts: effect of framework Fe by hydrothermal synthesis. Separ. Purif. Technol. 237: 116452, https://doi.org/10.1016/j.seppur.2019.116452.Search in Google Scholar

Yang, Y., Zhang, H., Huang, H., Yan, Y., and Zhang, X. (2020c). Iron-loaded carbon nanotube-microfibrous composite for catalytic wet peroxide oxidation of m-cresol in a fixed bed reactor. Environ Sci Pollut R 27: 6338–6351.10.1007/s11356-019-07362-6Search in Google Scholar PubMed

Yu, Y., Wei, H., Yu, L., Zhang, T., Wang, S., Li, X., Wang, J., and Sun, C. (2015). Surface modification of sewage sludge derived carbonaceous catalyst for m-cresol catalytic wet peroxide oxidation and degradation mechanism. RSC Adv. 5: 41867–41876, https://doi.org/10.1039/c5ra00858a.Search in Google Scholar

Yu, Y., Wei, H., Yu, L., Wang, W., Zhao, Y., Gu, B., and Sun, C. (2016). Sewage-sludge-derived carbonaceous materials for catalytic wet hydrogen peroxide oxidation of m-cresol in batch and continuous reactors. Environ. Technol. 37: 153–162, https://doi.org/10.1080/09593330.2015.1065006.Search in Google Scholar PubMed

Yue, Z., She, R., Bao, H., Tian, J., Yu, P., Zhu, J., Chang, L., Ding, Y., and Sun, Q. (2012). Necrosis and apoptosis of renal tubular epithelial cells in rats exposed to 3-methyl-4-nitrophenol. Environ. Toxicol. 27: 653–661, https://doi.org/10.1002/tox.20688.Search in Google Scholar PubMed

Received: 2021-01-11
Accepted: 2021-04-04
Published Online: 2021-07-22
Published in Print: 2022-11-25

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 7.2.2023 from https://www.degruyter.com/document/doi/10.1515/revce-2021-0001/html
Scroll Up Arrow