Open access peer-reviewed chapter

Physiochemical Properties and Removal Methods of Phenolic Compounds from Waste Waters

Written By

Yesim Gucbilmez

Submitted: September 8th, 2021 Reviewed: November 8th, 2021 Published: January 7th, 2022

DOI: 10.5772/intechopen.101545

Chapter metrics overview

92 Chapter Downloads

View Full Metrics

Abstract

In this chapter, phenol and chlorophenols are investigated in terms of their production histories, physiochemical properties, pollution resources, and removal methods. It is seen that both phenol and chlorophenols are highly toxic compounds, produced from natural and anthropogenic sources, which are hazardous to both humans and the environment even at very low concentrations. The typical industries which produce phenol and chlorophenol pollution are petrochemical, textile, plastics, resin, dye, pharmaceutical, iron and steel, pulp and paper industries as well as the petroleum refineries, and coal gasification operations. Phenol is a highly corrosive and nerve poisoning agent. It causes harmful health effects, such as sour mouth, diarrhea, and impaired vision. It is also toxic for the ecosystem with toxicity levels ranging between 10-24 mg/L for humans, 9-25 mg/l for fish, and lethal blood concentration around 150-mg/100 ml. Chlorophenols found in natural waters or drinking water also cause serious health problems such as histopathological alterations, genotoxicity, mutagenicity, and carcinogenicity among others. Due to the aforementioned reasons, the phenolic compounds in wastewaters or drinking water must be removed using a suitable wastewater treatment method such as adsorption, extraction, electrochemical oxidation, biodegradation, catalytic wet air oxidation, or enzyme treatment among others.

Keywords

  • phenol
  • chlorophenols
  • wastewater treatment
  • phenolic compounds
  • phenolics
  • organic pollutants

1. Introduction

Due to technological advances and rapid industrial growth, water systems around the world are under threat. In general, developing countries suffer from water pollution originating from agricultural sources whereas developed countries have chemical discharge problems. In most wastewaters and drinking water, one or more of the following toxic organic pollutants may occur [1]: Organochlorines, chlorobenzenes (CBs), polychlorinated dibenzo-p-dioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs), phenols, chlorophenols, and other phenol-derived compounds.

Phenolic compounds are phytochemicals found in nature that cannot be synthesized in the human body. They are mainly obtained from food and medicinal herbs and are present in most fruits and vegetables [2]. They are found in water systems due to the discharge streams of industrial, agricultural, and domestic activities as well as the result of natural phenomena. They cause severe and long-lasting health hazards including damage to red blood cells and the human liver. Their interaction with the aquatic ecosystem can produce new compounds, which can be as toxic as the original phenolic molecules [3].

Chlorophenols (CPs) are common contaminants that can be found in surface, ground, and drinking waters [4, 5, 6, 7, 8]. Thermal and chemical decomposition of chlorophenols leads to the formation of harmful compounds which cause public health problems such as genotoxicity, mutagenicity, and carcinogenicity among others. In addition, some electrophilic molecules may occur as a result of the transformation of chlorophenols, which may connect and harm the DNA or gene products [5, 6].

Advertisement

2. History of phenol and chlorophenols

The academic and industrial chemist F.F. Runge was born in 1794 in Billwerder near Hamburg. Runge isolated phenol from coal tar in the year 1834 in an impure form and gave it the name “carbolic acid” “Karbols¨aure” (carbolic acid) [7, 8, 9].

British surgeon Joseph Lister used phenol as a disinfectant for the first time in 1865 for sterilizing surgical dressings, instruments, and wounds [10]. However, the phenol sprays used during the surgeries were dangerous for the lung’s mucous membrane when inhaled. Thus, by 1890, the phenol spray was abandoned by the medical community [11].

During the Boer War, England placed an embargo on phenol causing phenol shortage on the continent. This led F. Raschig works at Ludwigshafen, Germany, to produce synthetic phenol on a large scale and in 1940, Hooker Chemical Corporation built a plant based on the so called the Raschig-Hooker process for the commercial production of phenol [12, 13].

During World War I and World War II, the existing sulfonation process for the production of phenol was further improved and other processes such as chlorination process and the Raschig Process were commercialized for the first time [14]. In 1924, Dow Chemical started the commercial production of synthetic phenol using direct chlorination of benzene to chlorobenzene which was called the Dow Process [11].

In terms of patent literature, since the middle of the twentieth century, researchers have mainly tried to improve the existing processes rather than developing new ones. One such example was the 1989 European patent of Mitsui Petrochemical Limited which used a recycle loop to reduce the amount of the side product acetone [15, 16].

Presently, phenol is used in the manufacture of phenolic and epoxy resins [17, 18], plastics [19], plasticizers [20], polycarbonates [21], nylon [22], dyes [23, 24] disinfectants [25], herbicides [26], polymers, drugs, pesticides [27] wood preservatives [28], and fungicides [29].

Chlorophenols (CPs) are produced by the electrophilic halogenation of phenol with chlorine. There are five basic types and 19 different CPs. CPs are mostly used as pesticides, herbicides, antiseptics, and disinfectants [30]. They are very toxic and their presence is dangerous for humans as well as aquatic life. They are found in the wastewaters of textile, pharmaceutical, petrochemical, pesticide, paper, and other industries [31].

The processes given in Figure 1 have been mainly used in the industry for the production of phenol up to date [10, 32, 33, 34, 35] and among them, only the Hock and Toluene Oxidation Processes are important for the phenol industry, the others have been discarded for economic reasons [10].

Figure 1.

Processes used up to date for the industrial production of phenol [10,32,33,34,35].

The global phenol market reached a value of 23.17 billion US Dollars (USD) in the year 2020. The phenol market is further expected to grow at a compound annual growth rate (CAGR) of 5.3% between the years 2021 and 2026 to reach a value of about 30 billion USD by the year 2026 [36].

In the case of CPs, their production and usage have caused the presence of persistent toxic components into the water systems which are resistant to biological degradation. However, microorganisms exposed to these pollutants have obtained the ability to biologically degrade some of them and the biodegradation routes were seen to depend on the physicochemical and biological properties of the particular wastewater system under question. Understanding the genetic basis of catabolism of CPs may increase the efficiency of naturally occurring microorganisms or help to raise new microorganisms which can degrade CPs successfully [37].

Advertisement

3. Physiochemical properties of phenol and chlorophenols

Phenol is an odorous chemical compound, found either as a colorless liquid or white solid at room temperature, and maybe highly toxic and corrosive. Phenols are similar to alcohols but form stronger hydrogen bonds. The presence of stronger hydrogen bonds makes them more water-soluble than alcohols and their boiling points higher than those of alcohols [38]. They are widely used as raw materials in the manufacture of phenolic resins, automotive parts, nylon, epoxy resins, polycarbonate engineering thermoplastics, wood preservatives, heavy-duty surfactants, pharmaceuticals, disinfectants, tank linings, and coating materials among others. They are also widely used in household products; for instance, phenol-derived n-hexylresorcinol, is used in cough drops and other antiseptic applications and butylated hydroxytoluene (BHT) is a common antioxidant in foods. Also, in the dye industry, substituted phenols are used to make intensely colored azo dyes [38, 39].

CPs, produced by chlorinating phenol or hydrolyzing chlorobenzenes, contain the benzene ring, the OH group, and chlorine atoms. All CPs, except 2-CP, are solids with melting points in the range of 33–191°C. They are weakly acidic and their acidity is slightly lower than that of phenols. In reactions with alkaline metals in water solutions, they yield highly soluble metal salts. Their level of toxicity depends on the chlorination degree and the place of the chlorine atoms with respect to the hydroxyl group [40].

Advertisement

4. Sources of phenol and chlorophenol pollution

The presence of phenolic compounds in wastewaters stem from two main sources: Natural and human-based activities. Natural activities include the decomposition of dead plants and animals, synthesis by microorganisms and plants in the aquatic ecosystem. Human activities, on the other hand, include industrial, domestic, agricultural, and municipal activities [10].

Phenol enters water systems in effluents from major industries, such as petrochemical, textile, plastics, resin manufacturing, dye, pharmaceutical, iron and steel, pulp and paper as well as petroleum refineries, and coal gasification operations. It is very important to remove phenols and aromatic compounds from industrial streams before discharging them because of their toxicity to aquatic organisms [41, 42].

The CPs are among the most important environmental pollutants. They are mostly used in the production of paper and pesticides and also as intermediate materials in the production of dyes, plastics, and pharmaceuticals [43, 44, 45]. These industries often cause wastewater and groundwater pollution. In addition, as a result of tap water chlorination treatment, CPs have also been detected in drinking water [46].

Advertisement

5. Removal methods of phenol and chlorophenols

Phenol is a nerve poisoning agent and it is highly corrosive. It causes health hazards, such as diarrhea, sour mouth, and impaired vision. It is also toxic for fish and the toxicity levels are in the range of 10–24 mg/L for humans and 9–25 mg/L for fish while the lethal blood concentration is around 150-mg/100 ml [47].

The available removal methods used for phenol can be separated into two main groups: Traditional and advanced. Traditional methods include steam distillation, extraction, adsorption, ion exchange [42] and advanced methods include wet air oxidation, catalytic wet air oxidation, ozonation, membrane processes, electrochemical oxidation, biological processes/biodegradation, and enzymatic treatment among others [42, 48].

Using the relative volatility of phenol, steam distillation can be carried out in order to remove phenol from aqueous mixtures. The phenol–water mixture forms a minimum azeotrope at 9.21% (w/w) phenol [42, 49, 50, 51]. Using this property, azeotropic distillation or steam distillation can be used to treat phenol wastewaters to obtain effluent concentrations as low as 0.01 mg/L [48].

Liquid–liquid extraction is a commonly employed technique used for the removal of phenolic compounds. It can be used for a wide range of phenol concentrations and is economical in some cases. Benzene and butyl acetate have been popular as solvents in this process in the past, however, presently, the most used solvent is di-isopropyl ether, which is used in the phenosolvan process [50, 51]. For the extraction process, the solubility of the preferred solvent in water should be tolerable so that further purification steps will not be necessary. The selectivity of the solvent depends mainly on the type of the solvent, the system temperature, and the amount of phenol in the wastewater [50].

The adsorption method has been found to be successful for the removal of phenols from wastewaters for a large concentration scale, depending on the adsorbent, recycling, and economics. Among the used adsorbents, activated carbon (AC) is the most preferred one in the industry. It is expensive but has been shown to be efficient for the removal of even very low amounts of organic pollutants [51, 52, 53].

Chemical oxidation processes can turn phenolic compounds into smaller molecules that are less toxic and easier to process or mineralize [54, 55]. Among the chemical oxidation processes, advanced oxidation processes (AOPs) such as the Fenton process, ozonation, photolysis, or their combinations are recommended for low-concentration wastewaters. Incineration, on the other hand, is suitable for wastewaters for which the COD values are higher than 100 g/L, however, it is no more commonly used since it is not an eco-friendly process [56].

Wet air oxidation (WAO) is a very clean technology since no additive is added to cause secondary pollution. The reaction is carried out at moderate temperatures (175–320°C) but at high pressures (2.17–20.71 MPa); the organic pollutants in the wastewater are oxidized into small organic acid molecules which are likely to biodegrade [57]. This method can be used for the treatment of wastewaters with initial COD values in the concentration range of 20–200 g/L [58].

Catalytic wet air oxidation (CWAO) offers an alternative path to treat refractory wastewaters. CWAO gained a lot of interest over the past 20 years due to its ability to oxidize toxic wastewaters and complete their mineralization [59, 60, 61, 62, 63]. In addition, it is a heterogeneous process, thus, an extra catalyst separation step is not necessary in most cases making the process more economical to apply [64].

Many researchers have studied the electrochemical oxidation of phenolic compounds [65, 66]. In this process, the electrode should be electrochemically stable, economically viable, and very efficient for the removal of organic pollutants [67]. There are different researches carried out using several anodic materials like Ti = SnO2, Pt [68], vitreous carbon [69], and PbO2 [70]. Among them, PbO2 electrodes have been successfully applied due to their high electrical conductivity values, strong oxidizing properties, and low costs [71, 72].

Biological treatment or biodegradation is the most widely employed method for the removal of phenols from water systems. The treatment is inexpensive, simple to design and maintain, and transforms the phenolic solutions into simple end products. Phenolic molecules such as Bisphenol A (BPA) can also be successfully treated with biological treatments such as activated sludge [73, 74, 75].

CPs, on the other hand, can be removed from wastewaters by a variety of methods including biological treatment [14], advanced oxidation processes [76], and adsorption [77, 78, 79].

Although various traditional and advanced methods are possible to apply for the removal of phenol from wastewaters; the two important parameters which define the suitable method are the initial and final phenol concentrations as seen in Table 1 [42].

Initial Concentration (mg/L)MethodInitial Concentration (mg/L)MethodFinal Concentration (mg/L)Method
Over 3000-6,000 or 20-500LLE~50Photocatalytic Oxidation<10Bio-degradation
Up to 4,000 or 300-3000Adsorption~50Chemical-Electrochem. OxidationVery lowAdsorption
~3,000Distillation<50Bio-degradationVery lowPhotocatalytic Oxidation

Table 1.

Initial and Final Phenol Concentrations of Waste Waters and Corresponding Removal Methods (Modified from [42]).

Advertisement

6. Comparison of different methods for the removal of phenol and chlorophenols

Researchers still extensively focus on phenol removal methods from wastewaters, considering both traditional methods such as adsorption and steam distillation and advanced processes, such as wet air oxidation and biodegradation. The traditional methods mostly have the drawbacks of low efficiency and high operational cost which can be cured by using low-cost adsorbents or increasing the surface area of the existing adsorbents. In the case of advanced methods, enzymatic treatment which uses different peroxidases seems to be an efficient method with removal efficiencies above 95% [49].

As for CPs, adsorption, biodegradation, and oxidation by AOPs seem more widely used than other methods [76, 77, 78, 79]. AOPs involve the formation and use of hydroxyl ions (OH) through chemical, photochemical, or photocatalytic methods [77]. Adsorption has been reported to be one of the most successful methods for CP removal from wastewaters since it is a simple method with a low-maintenance cost, high efficiency, and less toxic by-product generation [79].

Advertisement

7. Conclusions

Phenols and CPs are important compounds used in the manufacture of epoxy resins, plastics, polycarbonates, nylon, dyes, disinfectants herbicides, drugs, pesticides, wood preservatives, and fungicides among others. However, they are quite toxic chemicals, even at low concentrations, causing harmful effects ranging from sour mouth, diarrhea, and impaired vision to histopathological alterations, genotoxicity, mutagenicity, carcinogenicity, and death. Thus, wastewaters containing phenol and CPs have to be treated thoroughly before being discharged into water systems. The water treatment processes used in industry depend on the type of wastewater and initial and final concentrations of the phenol and CPs. Traditional methods such as adsorption and distillation or advanced methods such as wet air oxidation and biological treatment can be used to remove phenol and CPs from wastewaters. For the removal of phenol from wastewaters, among traditional methods, the adsorption method is efficient on a large scale of concentrations, depending on the economics, recycling, and the adsorbent properties. Among advanced methods, on the other hand, the inexpensive and simple to design biological treatment is the most commonly applied method and the enzymatic treatment yields more than 95% phenol removal efficiency using different peroxidases. Finally, for the removal of chlorophenols from wastewater systems, the most used methods are adsorption, biological treatment, and advanced oxidation processes.

References

  1. 1. Tang W. Physicochemical Treatment of Hazardous Wastes. 1st ed. Florida: Routledge Taylor & Francis Group, CRC Press; 2016. 608 p. ISBN: 9781566769273
  2. 2. Taamalli A, Contreras M, Abu-Reidah I, Trabelsi N, Ben YN. Quality of phenolic compounds: Occurrence, health benefits, and applications in food industry. Journal of Food Quality. 2019;2019:1-2. DOI: 10.1155/2019/9594646
  3. 3. Laura A, Moreno-Escamilla J, Rodrigo-García J, Alvarez-Parrilla E. Phenolic compounds. In: Yahia E, Carillo-Lopez A, editors. by. 1st ed. Woodhead Publishing; 2018. Ceccaroli B, Lohne O. Solar grade silicon feedstock. In: Luque A, Hegedus S, editors. Handbook of Photovoltaic Science and Engineering. 2nd ed. Chichester: Wiley; 2011. pp. 169-217. DOI: 10.1002/978047974704.ch5
  4. 4. Anku W, Mamo M, Govender P. Phenolic compounds in water: Sources, reactivity, toxicity and treatment methods. In: Soto-Hernández M, Palma-Tenango M, García-Mateos R, editors. Phenolic Compounds. London: InTechOpen; 2017. DOI: 10.5772/67213
  5. 5. Davı̀ M, Gnudi F. Phenolic compounds in surface water. Water Research. 1999;33(14):3213-3219. DOI: 10.1016/S0043-1354(99)00027-5
  6. 6. Olaniran A, Igbinosa E. Chlorophenols and other related derivatives of environmental concern: Properties, distribution and microbial degradation processes. Chemosphere. 2011;83(10):1297-1306. DOI: 10.1016/j.chemosphere.2011.04.009
  7. 7. Runge F. Ueber einige Produkte der Steinkohlendestillation. Annalen der Physik und Chemie. 1834;107(5):65-78. DOI: 10.1002/andp.18341070502
  8. 8. Runge F. Ueber einige Producte der Steinkohlendestillation. Annalen der Physik und Chemie. 1834;108(20-25):328-333
  9. 9. Reichenbach. Meinung von dem Kyanol, der Karbolsäure u. s. f. des Hrn. Runge. Annalen der Physik und Chemie. 1834;107(32):497-512
  10. 10. Nguyen MT, Kryachko ES, Vanquickenborne LG. General and theoretical aspects of phenols. In: Rappoport Z et al., editors. The Chemistry of Phenols. Chichester: Wiley; 2013. p. 6. DOI: 10.1002/0470857277
  11. 11. Reddy N, Elias A. Chlorine and the chemistry of disinfectants. Resonance. 2021;26(3):341-366. DOI: 10.1007/s12045-021-1135-y
  12. 12. Kenyon R, Boehmr N. Phenol by sulfonation. Industrial and Engineering Chemistry. 1950;42(8):1446-1455
  13. 13. Mukhopadhyay AK. Industrial Chemical Cresols and Downstream Derivatives. New York: Marcel Dekker; 2005. 202 p.
  14. 14. Shinohara Y. Development in the manufacturing process of phenol. Journal of Synthetic Organic Chemistry, Japan. 1977;35(2):138-146. DOI: 10.5059/yukigoseikyokaishi.35.138
  15. 15. Mitsui Petrochemical Industries. Preparation of Phenol Through Cumene. EP0371738A2. 1989
  16. 16. Daowdat B, Hoeltzel G, Tannenbaum R. Direct Route to Phenol from Benzene [Internet]. 2017. Available from:https://repository.upenn.edu/cgi/viewcontent.cgi?article=1089&context=cbe_sdr[Accessed: 2021-12-25]
  17. 17. Uyigue L, Kubiangha EO. Estimation of Product Yield and Kinetic Parameters of Phenolic Resin Pre-Polymer Synthesis Using Acid and Base Catalyst. International Journal of Engineering and Modern Technology. 2018;4(3):25-39
  18. 18. Yang G, Rohde B, Tesefay H, Robertson M. Biorenewable epoxy resins derived from plant-based phenolic acids. ACS Sustainable Chemistry & Engineering. 2016;4(12):6524-6533. DOI: 10.1021/acssuschemeng.6b01343
  19. 19. Cygan M, Szemień M, Krompiec S. Statistical screening analysis of the chemical composition and kinetic study of phenol-formaldehyde resins synthesized in the presence of polyamines as co-catalysts. PLoS One. 2018;13(5):e0195069. DOI: 10.1371/journal.pone.0195069
  20. 20. Kim W, Joshi U, Lee J. Making polycarbonates without employing phosgene: An overview on catalytic chemistry of intermediate and precursor syntheses for polycarbonate. Industrial & Engineering Chemistry Research. 2004;43(9):1897-1914. DOI: 10.1021/ie034004z
  21. 21. Wang B, Wang L, Zhu J, Chen S, Sun H. Condensation of phenol and acetone on a modified macroreticular ion exchange resin catalyst. Frontiers of Chemical Science and Engineering. 2013;7(2):218-225. DOI: 10.1007/s11705-013-1330-9
  22. 22. Vedamurthy T, Murugesan M. Synthesis, characterization, and evaluation of the hydrophobic, dielectric properties of phenols functionalized nylon 6 polymers by zinc acetate catalyst using Mannich reaction. Materials Chemistry and Physics. 2018;216:517-525. DOI: 10.1016/j.matchemphys.2018.05.070
  23. 23. Im KM, Jeon J. Synthesis of plant phenol-derived polymeric dyes for direct or mordant-based hair dyeing. Journal of Visualized Experiments. 2016;118:54772. DOI: 10.3791/54772
  24. 24. Ajani O, Akinremi O, Ajani A, Edobor-Osoh A, Anake W. Synthesis and spectroscopic study of naphtholic and phenolic azo dyes. Physical Review & Research International. 2013;3(1):28-41
  25. 25. DeBono R, Laitung G. Phenolic household disinfectants — further precautions required. Burns. 1997;23(2):182-185. DOI: 10.1016/s0305-4179(96)00114-3
  26. 26. Argese E, Bettiol C, Marchetto D, De Vettori S, Zambon A, Miana P, et al. Study on the toxicity of phenolic and phenoxy herbicides using the submitochondrial particle assay. Toxicology In Vitro. 2005;19(8):1035-1043. DOI: 10.1016/s0305-4179(96)00114-3. DOI: 0.1016/j.tiv.2005.05.004
  27. 27. Michałowicz J, Duda W. Phenols – Sources and Toxicity. Polish Journal of Environmental Studies. 2007;16(3):347-362
  28. 28. Rättö M, Ritschkoff A, Viikari L. Enzymatically polymerized phenolic compounds as wood preservatives. Holzforschung. 2004;58(4):440-445. DOI: 10.1515/HF.2004.067
  29. 29. Zabka M, Pavela R. Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi. Chemosphere. 2013;93(6):1051-1056. DOI: 10.1016/j.chemosphere.2013.05.076
  30. 30. Badanthadka M, Mehendale H. Chlorophenols. In: Wexler P. et al., ed. by. Encyclopedia of Toxicology Volume 1. Amsterdam: Elsevier; 2014. ISBN: 9780080548005
  31. 31. Igbinosa E, Odjadjare E, Chigor V, Igbinosa I, Emoghene A, Ekhaise F, et al. Toxicological profile of chlorophenols and their derivatives in the environment: The public health perspective. The Scientific World Journal. 2013;2013:1-11. DOI: 10.1155/2013/460215
  32. 32. Ullman F. Ullmann’s Encyclopedia of Industrial Chemistry. 6th ed. New York: Wiley; 2000. ISBN: 9783527306732 3527306730
  33. 33. Eikhman R, Shemyakin M, Vozhdaeva V. Anilinokrasochnaya. 1934;4:523
  34. 34. Tishchenko V, Churbakov A. Journal of Applied Chemistry of the USSR. 1934;7:764
  35. 35. Vorozhtzov NN Jr, Oshuev AG. Anilinokrasochnaya Promyshl. 1933;3:245
  36. 36. Global Phenol Market Report and Forecast 2021-2026 [Internet].Expertmarketresearch.com. 2021. [cited 7 September 2021]. Available from:https://www.expertmarketresearch.com/reports/phenol-market-report
  37. 37. Chaudhry G, Chapalamadugu S. Biodegradation of halogenated organic compounds. Microbiological Reviews. 1991;55(1):59-79. DOI: 10.1128/mr.55.1.59-79.1991
  38. 38. Wade L. phenol | Definition, Structure, Uses, & Facts [Internet]. Encyclopedia Britannica. 2021. [cited 7 September 2021]. Available from:https://www.britannica.com/science/phenol
  39. 39. [Internet]. Shell.com. 2021. [cited 7 September 2021]. Available from:https://www.shell.com/business-customers/chemicals/our-products/phenol/_jcr_content/par/textimage.stream/1447712147800/e2796436311990d667d25cd639351276d2ea574d/datasheet-phenol.pdf
  40. 40. Yao L, Jiang Y, Shi J, Tomas-Barberan F, Datta N, Singanusong R, et al. Flavonoids in Food and Their Health Benefits. Plant Foods for Human Nutrition. 2004;59(3):113-122. DOI: 10.1007/s11130-004-0049-7
  41. 41. Czaplicka M. Sources and transformations of chlorophenols in the natural environment. Science of the Total Environment. 2004;322(1-3):21-39. DOI: 10.1016/j.scitotenv.2003.09.015
  42. 42. Mohammadi S, Kargari A, Sanaeepur H, Abbassian K, Najafi A, Mofarrah E. Phenol removal from industrial wastewaters: A short review. Desalination and Water Treatment. 2014;53(8):2215-2234. DOI: 10.1080/19443994.2014.883327
  43. 43. Li D, Park J, Oh J. Silyl derivatization of alkylphenols, chlorophenols, and bisphenol A for simultaneous GC/MS determination. Analytical Chemistry. 2001;73(13):3089-3095. DOI: 10.1021/ac001494l
  44. 44. Santana C, Padrón M, Ferrera Z, Rodríguez J. Development of a solid-phase microextraction method with micellar desorption for the determination of chlorophenols in water samples. Journal of Chromatography A. 2007;1140(1-2):13-20. DOI: 10.1021/ac001494l
  45. 45. de Morais P, Stoichev T, Basto M, Vasconcelos M. Extraction and preconcentration techniques for chromatographic determination of chlorophenols in environmental and food samples. Talanta. 2012;89:1-11. DOI: 10.1016/j.talanta.2011.12.044
  46. 46. Jin M, Yang Y. Simultaneous determination of nine trace mono- and di-chlorophenols in water by ion chromatography atmospheric pressure chemical ionization mass spectrometry. Analytica Chimica Acta. 2006;566(2):193-199. DOI: 10.1016/j.aca.2006.03.017
  47. 47. Kulkarni S, Kaware D. Review on research for removal of phenol from wastewater. International Journal of Scientific and Research Publications. 2013;3(4):1-5
  48. 48. Pérez Ramírez EE, de la Luz Asunción M, Saucedo Rivalcoba V, Martínez Hernández A, Velasco Santos C. In: Soto-Hernández M, Palma-Tenango M, García-Mateos R, editors. Phenolic Compounds Natural Sources, Importance and Applications. London: InTechOpen; 2021. pp. 344-372. DOI: 10.5772/67213
  49. 49. Villegas L, Mashhadi N, Chen M, Mukherjee D, Taylor K, Biswas N. A short review of techniques for phenol removal from wastewater. Current Pollution Reports. 2016;2(3):157-167. DOI: 10.1007/s40726-016-0035-3
  50. 50. Busca G, Berardinelli S, Resini C, Arrighi L. Technologies for the removal of phenol from fluid streams: A short review of recent developments. Journal of Hazardous Materials. 2008;160(2-3):265-288
  51. 51. Chemat F, Boutekedjiret C. Extraction//Steam distillation. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Amsterdam: Elsevier; 2021. ISBN: 9780124095472 012409547X
  52. 52. Park H, Koduru J, Choo K, Lee B. Activated carbons impregnated with iron oxide nanoparticles for enhanced removal of bisphenol A and natural organic matter. Journal of Hazardous Materials. 2015;286:315-324. DOI: 10.1016/j.jhazmat.2014.11.012
  53. 53. Tran V, Ngo H, Guo W, Zhang J, Liang S, Ton-That C, et al. Typical low cost biosorbents for adsorptive removal of specific organic pollutants from water. Bioresource Technology. 2015;182:353-363. DOI: 10.1016/j.biortech.2015.02.003
  54. 54. Zhou L, Cao H, Descorme C, Xie Y. Phenolic compounds removal by wet air oxidation based processes. Frontiers of Environmental Science & Engineering. 2017;12(1):1-20. DOI: 10.1007/s11783-017-0970-2
  55. 55. Ribeiro A, Nunes O, Pereira M, Silva A. An overview on the advanced oxidation processes applied for the treatment of water pollutants defined in the recently launched Directive 2013/39/EU. Environment International. 2015;75:33-51. DOI: 10.1016/j.envint.2014.10.027
  56. 56. Andreozzi R. Advanced oxidation processes (AOP) for water purification and recovery. Catalysis Today. 1999;53(1):51-59. DOI: 10.1016/S0920-5861(99)00102-9
  57. 57. Víctor-Ortega M, Ochando-Pulido J, Martínez-Férez A. Phenols removal from industrial effluents through novel polymeric resins: Kinetics and equilibrium studies. Separation and Purification Technology. 2016;160:136-144. DOI: 10.1016/j.seppur.2016.01.023
  58. 58. Debellefontaine H, Chakchouk M, Foussard JN, Tissot D, Striolo P. Treatment of organic aqueous wastes: Wet air oxidation and wet peroxide oxidation(R). Environmental Pollution. 1996;1996(92):155-164. DOI: 10.1016/0269-7491(95)00100-x
  59. 59. Fortuny A, Ferrer C, Bengoa C, Font J, Fabregat A. Catalytic removal of phenol from aqueous phase using oxygen or air as oxidant. Catalysis Today. 1995;24(1-2):79-83. DOI: 10.1016/0920-5861(95)00002-w
  60. 60. Maugans C, Akgerman A. Catalytic wet oxidation of phenol in a trickle bed reactor over a Pt/TiO2 catalyst. Water Research. 2003;37(2):319-328. DOI: 10.1016/s0043-1354(02)00289-0
  61. 61. Suárez-Ojeda M, Fabregat A, Stüber F, Fortuny A, Carrera J, Font J. Catalytic wet air oxidation of substituted phenols: Temperature and pressure effect on the pollutant removal, the catalyst preservation and the biodegradability enhancement. Chemical Engineering Journal. 2007;132(1-3):105-115. DOI: 0.1016/j.cej.2007.01.025
  62. 62. Monteros A, Lafaye G, Cervantes A, Del Angel G, Barbier J Jr, Torres G. Catalytic wet air oxidation of phenol over metal catalyst (Ru,Pt) supported on TiO2–CeO2 oxides. Catalysis Today. 2015;258:564-569. DOI: 10.1016/j.cattod.2015.01.009
  63. 63. Baloyi J, Ntho T, Moma J. Synthesis and application of pillared clay heterogeneous catalysts for wastewater treatment: A review. RSC Advances. 2018;8(10):5197-5211. DOI: 10.1039/C7RA12924F
  64. 64. Serra-Pérez E, Ferronato C, Giroir-Fendler A, Álvarez-Torrellas S, Ovejero G, García J. Highly efficient Ru supported on carbon nanosphere nanoparticles for ciprofloxacin removal: Effects of operating parameters, degradation pathways, and kinetic study. Industrial & Engineering Chemistry Research. 2020;59(35):15515-15530. DOI: 10.1021/acs.iecr.0c02509
  65. 65. Comninellis C, Pulgarin C. Electrochemical oxidation of phenol for wastewater treatment using SnO2, anodes. Journal of Applied Electrochemistry. 1993;23:108-112
  66. 66. Simond O, Schaller V, Comninellis C. Theoretical model for the anodic oxidation of organics on metal oxide electrodes. Electrochimica Acta. 1997;42(13-14):2009-2012. DOI: 10.1016/S0013-4686(97)85475-8
  67. 67. Gu L, Wang B, Ma H, Kong W. Multi-phase electro-chemical catalytic oxidation of wastewater. Journal of Chemical Technology & Biotechnology. 2006;81(10):1697-1704. DOI: 10.1002/jctb.1594
  68. 68. Bashir M, Isa M, Kutty S, Awang Z, Aziz H, Mohajeri S, et al. Landfill leachate treatment by electrochemical oxidation. Waste Management. 2009;29(9):2534-2541. DOI: 10.1016/j.wasman.2009.05.004
  69. 69. Gomes L, Freitas R, Malpass G, Pereira E, Motheo A. Pt film electrodes prepared by the Pechini method for electrochemical decolourisation of Reactive Orange 16. Journal of Applied Electrochemistry. 2008;39(1):117-121. DOI: 10.1007/s10800-008-9649-5
  70. 70. Gaudet J, Tavares A, Trasatti S, Guay D. Physicochemical Characterization of Mixed RuO2−SnO2 Solid Solutions. Chemistry of Materials. 2005;17(6):1570-1579. DOI: 10.1021/cm048129l
  71. 71. Zhao T, Lu J, Hu C, Zhu C, Zhao J, Dong W. Electrochemical degradation of 4, 4′-(propane-2, 2-diyl) diphenol in water with CeO2=β-PbO2=Ti electrode. International Journal of Electrochemical Science. 2014;9:2354-2366
  72. 72. Stucki S, Kötz R, Carcer B, Suter W. Electrochemicalwastewater treatment using high overvoltage anodes. Part II: Anode performance and appliations. Journal of Applied Electrochemistry. 1991;21:99-104
  73. 73. Busca G, Berardinelli S, Resini C, Arrighi L. Technologies for the removal of phenol from fluid streams: A short review of recent developments. Journal of Hazardous Materials. 2008;160(2-3):265-288. DOI: 10.1016/j.jhazmat.2008.03.045
  74. 74. Saratale R, Hwang K, Song J, Saratale G, Kim D. Electrochemical oxidation of phenol for wastewater treatment using Ti/PbO2 electrode. Journal of Environmental Engineering. 2016;142(2):04015064. DOI: 10.1061/(ASCE)EE.1943-7870.0001007
  75. 75. Ramírez E, Asunción M, Rivalcoba V, Hernández A, Santos C. Removal of phenolic compounds from water by adsorption and photocatalysis. In: Soto-Hernández M, Palma-Tenango M, García-Mateos R, editors. Phenolic Compounds - Natural Sources, Importance and Applications. London: Intech Open; 2017. DOI: 10.5772/66895
  76. 76. Pera-Titus M, Garcı́a-Molina V, Baños M, Giménez J, Esplugas S. Degradation of chlorophenols by means of advanced oxidation processes: a general review. Applied Catalysis B: Environmental. 2004;47(4):219-256. DOI: 10.1016/j.apcatb.2003.09.010
  77. 77. Dąbrowski A, Podkościelny P, Hubicki Z, Barczak M. Adsorption of phenolic compounds by activated carbon—a critical review. Chemosphere. 2005;58(8):1049-1070. DOI: 10.1016/j.chemosphere.2004.09.067
  78. 78. Soto M, Moure A, Domínguez H, Parajó J. Recovery, concentration and purification of phenolic compounds by adsorption: A review. Journal of Food Engineering. 2011;105(1):1-27. DOI: 10.1016/j.jfoodeng.2011.02.010
  79. 79. Kuśmierek K. The removal of chlorophenols from aqueous solutions using activated carbon adsorption integrated with H2O2 oxidation. Reaction Kinetics, Mechanisms and Catalysis. 2016;119(1):19-34. DOI: 10.1007/s11144-016-1039-0

Written By

Yesim Gucbilmez

Submitted: September 8th, 2021 Reviewed: November 8th, 2021 Published: January 7th, 2022