A REVIEW ON BIODEGRADATION OF PHENOL FROM
M.V.V.chandana Lakshmi and V. Sridevi
Department of chemical Engineering (Biotechnology), College of Engineering, Andhra University, Visakhapantam 530 003, Andhra Pradesh, India
- *Corresponding Author:
- Chandana Lakshmi
Email : email@example.com
Visit for more related articles at
Journal of Industrial Pollution Control
The environment, as a consequence of industrial and agricultural revolutions, tends to harden with potentially carcinogenic and mutagenic halogen-substituted aromatic compounds. Phenol and its higher molecular homologues are dangerous environmental pollutants. Due to their toxic character, these molecules tend to accumulate in water and soil after being discharged without an adequate treatment. Physical and chemical methods have been designed to remove phenol from effluents but many of these methods are commercially impractical either because of their high operating costs or because of the difficulty encountered in treating the solid wastes generated. In recent years, Biodegradation has been studied as an alternative technology, one of the most efficient and cost effective waste treatment technologies available to industries. Treatment of polluted sites or waste streams can be performed by using systems, in which the number of desirable microorganisms increase because they proliferate at the expense of contaminants. In the present work, detailed description of the properties, sources, hazards, physico-chemical methods, microbial degradation, phenol degrading microorganisms, degradation methods, metabolic pathway and analysis are presented. It has been found that phenol degradation by Pseudomonas putida has been widely adopted as preferred alternative.
Phenol, Biodegradation, Bacteria, Fungi, Yeast, Algae, Metabolic pathway.
Environmental pollution is considered as a side effect of modern industrial society. The presence of man-made (anthropogenic) organic compounds in the environment is a very serious public health problem. Soil and water of lakes, rivers and seas are highly contaminated with different toxic compounds such as phenol, ammonia, cyanides, thiocyanate, phenol formaldehyde, acrylo- and aceto- nitrile, mercury, heavy metals like chromium, zinc, cadmium, copper, nickel etc. Thirty monoaromatics are on the EPA priority pollutant list and 11 of these compounds are among the top of hundred chemicals on the priority list of hazardous substances published by the Agency for toxic substances and disease registry. Monoaromatic hydrocarbons such as benzene, toluene and phenol are obvious choices for studies on biodegradation. Among these, phenols are considered to be pollutants.
Chemical identity, physical and chemical properties of phenol
Phenol, C6H5OH or hydroxybenzene, is an aromatic molecule containing hydroxyl group attached to the benzene ring structure. Phenol commonly known as carbolic acid (Gardner et al. 1978) has a molecular weight of 94.11gm/mol (Lide, 1993). It has a melting point of 43ºC and forms white to colorless crystals, colorless to pink solid or thick liquid. It has a characteristic acrid smell and a sharp burning taste. Phenol has relatively high water solubility and is soluble in most organic solvents such as aromatic hydrocarbons, alcohols, ketones, ethers, acids, halogenated hydrocarbons (Lide, 1993). However, the solubility is limited in aliphatic solvents. The odour threshold of phenol in air is 0.04 ppm (v/v) (Amoore and Hautala, 1983) and in water between 1 ppm and 7.9 ppm (w/v) (Amoore and Hautala, 1983).
Sources of phenol
The origin of phenol in the environment is from natural, man-made and endogenous sources. Phenol consequent to its manufacture and use in such practices as wood burning, auto exhaust, etc., finds released primarily in air and water. Phenol mainly enters into waters from industrial effluent discharges.
1. Natural Sources: Phenol is a constituent of coal tar, and is formed during decomposition of organic materials. Increased environmental levels may result from forest fires. It has been detected among the volatile components from liquid manure at concentrations of 7-55 μg/Kg dry weight and has an average concentration in manure of 30μg/Kg dry weight.
2. Man-made sources: Man-made sources are from industrial wastes from fossil fuel extraction, wood processing industry, pesticide manufacturing plants (Kumaran and Parachuri, 1997), petroleum refinery, petrochemicals, organic chemical manufacture, coal refining, plastics, pharmaceuticals, tannery, pulp and paper mills (Kumaran & Paruchuri, 1997), as well as from agricultural run-off. Domestic wastewater and chemical spills from several other process industries release phenolic compounds to the environment. (Table 1)
Table 1. Sources of phenol and other related aromatic compounds in wastewater
3. Endogenous Sources: An important additional source of phenol may be the formation from various xenobiotics such as benzene (Pekari et al. 1992) under the influence of light.
Hazards of phenol
Aromatic hydrocarbons are not as readily biodegradable as the normal and branched. But alkanes, they are somewhat more easily degradable than the alicyclic hydrocarbons. Many of these compounds are toxic and some are known or suspected carcinogens (Sheeja and Murugesan, 2002). The presence of phenol in drinking water and irrigation water represents a serious health hazards to humans, animals, plants and microorganisms.
to some form of aquatic life and ingestion of 1gm of phenol can be fatal in human beings (Seetharam and Saville, 2003). Continuous ingestion of phenol for a prolonged period of time causes mouth sore, diarrhea, excretion of dark urine and impaired vision at concentrations levels ranging between 10 and 240 mg/L (Barker et al. 1978). Lethal blood concentration for phenol is around 4.7 to 130 mg/100mL. Phenol affects the nervous system and key organs, i.e. spleen, pancreas and kidneys (Manahan, 1994). Phenol is lethal to fish even at relatively low levels, e.g. 5-25 mg/L, depending on the temperature and state of maturity of rainbow trout (Brown et al. 1967). Phenolic compounds are also responsible for several biological effects, including antibiosis (Gonzalez et al. 1990), ovipositional deterrence (Girolami et al. 1981) and phytotoxicity (Capasso et al. 1992).
Phenol is classified as a priority pollutant owing to their high toxicity and wide spread environmental occurrence. Various regulatory authorities have imposed strict limits to phenol concentration in industrial discharges. Many countries regulate phenol released into the environment. For drinking water, a guideline concentration of 1μg/L (WHO, 1994) has been prescribed. In Malaysia, the Environmental Protection Act, 1974 establishes a phenol concentration of 0.001mg/L for Standard A, 0.1 mg/L for standard B and 5 mg/L other than standard A and B as the limit for wastewater discharges into inland waters. Therefore, it can be seen that disposal of phenol has become a major global concern.
The impacts of pollution on the environment have led to intense scientific investigations. The removal of phenol from industrial effluents has attracted researchers from different fields. The increasing awareness on the environment in both developed and developing countries has initiated more studies of possible solutions for treating phenol.
Different treatment methods are available for reduction of phenol content in wastewater. Phenolic wastes are treated by several physico-chemical methods like Chlorination, Advanced oxidation process (Santiago et al. 2002), Adsorption, Solvent Extraction, Coagulation, Flocculation, Reverse osmosis, Ozonisation, Photo catalysis and Electrolytic oxidation (Arutchelvan et al. 2005).
Chlorine may be applied in gaseous form or as an ionized product of solids. Chlorine can react with naturally occurring organic compounds found in water and produce dangerous compounds, known as disinfection byproducts.
Advanced Oxidation Processes (AOPs)
The AOPs use ozone, UV, ozone in combination with UV (O3/UV), ozone plus hydrogen peroxide (O3/ H2O2), hydrogen peroxide and ultraviolet light (UV/ H2O2). The main problem of AOPs lies in the high cost of reagents such as ozone, hydrogen peroxide or energy light sources like ultraviolet lights.
In adsorption process solutes from liquid media are adsorbed onto solids. The most widely used adsorbent for wastewater treatment applications is activated carbon, since it has large internal surface area per unit rate. But its applicability is confined to low concentrations of solutes.
A mixture of two components is treated by a solvent that preferentially dissolves one or more of the components in the mixture. If the initial concentration is less than 2 gm/L, extra operating and capital costs is required.
Coagulation is the formation of small flocs from dispersed colloids using coagulating agents. The major disadvantage of coagulation / flocculation processes is the production of sludge and subsequent separation and removal of it.
Flocculation is the agglomeration of small flocs into larger settleable particles using flocculating agents.
uses the pressure to drive water through the membrane against the force of osmotic pressure. The main disadvantage is concentration polarization, which is the accumulation of solute molecules on the membrane surface and may cause membrane fouling. Unless membranes are well maintained, algae and other life forms can colonize the membranes.
The process of treating, impregnating, or combining with ozone. The main disadvantage of this process lies in the high cost of reagents.
It is the acceleration of a photoreaction in the presence of a catalyst. The main disadvantage is the additional cost associated with the downstream catalyst separation.
A cell containing an electrolyte through which an externally generated electric current is passed by a system of electrodes in order to produce an electrochemical reaction. The main disadvantage is high capital cost.
Hence, the disadvantages like incomplete phenol removal, high reagent and energy requirements, generation of toxic sludge or other waste products that require careful disposal has made it imperative to look for a cost-effective treatment method that is capable of removing phenol from industrial effluents. As alternatives, slowly biological tools are being substituted in pollution abatement programs. Researchers are studying pollutant degrading microorganisms, which inhabit polluted as well as contaminated environments. This new technology has been loosely grouped together under the term “Bioremediation”, a treatment process that uses microorganisms to breakdown, or degrades, hazardous substances into less toxic or non-toxic substances. Harnessing the potential of microbes to degrade phenol has been an area of considerable study to develop Bioremediation approaches, which is considered as “Green Option” for treatment of environmental contaminants.
Microbial degradation of chemicals in the environment is a route for their removal. The microbial degradation of these compounds is a complex series of biochemical reactions and often different when different microorganisms are involved. The interdependence of biodegradation, biotransformation and biocatalysis has been reviewed by Parales et al. 2002. Microbial degradation of pollutants is crucial in order to predict their longevity and long term effects and also important in the actual remediation process.
Depending on the type of bacteria that are responsible for the degradation i.e., in the presence of free oxygen or oxygen in combined state, bioremediation is classified as “aerobic” or “anaerobic”.
In aerobic respiration, oxygen acts as the electron acceptor. Molecular oxygen is a reactant for oxygenase enzymes and is incorporated into the final products. In anaerobic respiration, different inorganic electron acceptors are possible such as NO3 -, SO42 -, S0, CO2 and Fe3 +. Most of the biodegradation is aerobic as anaerobic process is relatively slow and is difficult to maintain for bioremediation process. It is preferred where reduction is favored over oxidation as in the case of chlorinated compounds. Many synthetic compounds accumulate in nature because the release rates exceed the rates of microbial and chemical degradation.
Two major reasons have been identified for low degradation rates. First, the biochemical potential to degrade certain compound is limited. This is more likely that fewer chemicals resemble natural compounds Secondly, the pollutant or other substrates, e.g., appropriate electron acceptors are unavailable to the microflora.
In the natural environment, the rate of degradation can be dependent on physical, chemical and biological factors, which may differ among ecosystems. Alexander 1985, reported that for a microbial transformation to occur, a number of conditions must be satisfied. These include :
1. Microorganisms must exist with the required enzyme to catalyze the specific transformations. There are unspecific enzymes that can attack several types of substrates, while other enzymes can only catalyze the breakdown of one specific bond in a specific compound. Duetz et al. 1994, reported that different bacterial strains may also degrade the same compound by different degradation patterns, depending on the types of enzymes used. Many degradation pathways are achieved only by the synergistic relationship of several species (Lappin et al. 1985).
2. The chemical must be made available for the microorganism. The inaccessibility may result if the chemical exists in a different phase from that of the bacteria, e.g., in a liquid phase immiscible with water, or sorbed to a solid phase.
3. The success of the degrading strains to proliferate will depend on their ability to compete for the organic compound, oxygen and other environmental factors.
Microorganisms that can degrade phenol were isolated as early as 1908 (Evans, 1947). The key components of microbial communities responsible for degradation of phenolic wastes are Pseudomonas species. Their physiological and genetic basis of phenol degradation has been described by many researchers (Kotturi et al. 1991; Nurk et al. 1991; Kiyohara et al. 1992; Motzkus et al. 1993; Arquiaga et al. 1995; Puhakka et al.1995; Buitron and Gonzalez, 1996).
Phenols are metabolized by microorganisms from a variety of different genera and species, as shown in Table 2. Bacteria, fungi, yeast and algae have been reported to be capable of degrading phenol. As shown in Table 2, Pseudomonas putida has been extensively investigated and has been reported to be capable of high rates of phenol degradation (Hutchinson and Robinson, 1988). According to Whitelely et al. 2001, isolates that were able to utilize phenol as a sole carbon source predominantly belonged to Pseudomonas pseudoalcaligenes. The earlier reports on the decomposition of phenolic compounds by yeasts were by strains belonging to the genera Oospora, Saccharomyces, Candida, Debaryomyces and Trichosporon cutaneum (Harris and Rickettes, 1962; Henderson, 1961; Neujahr and Varga, 1970; Neujahr et al. 1974; Hashimota, 1973). Among the yeast strains, Candida tropicalis has been the most studied and able to degrade phenol, phenol derivatives and aliphatic compounds at a relatively high phenol concentration (Krug et al. 1985; Chang et al. 1995; Ruiz-Ordaz et al. 2000). According to Yap et al. 1999, mutant strains Comamonas teststeroni E23 has been regarded as the best phenol degrader of all phenol degrading strains reported upto date.
Table 2. Phenol-degrading microorganisms
Table 3. Phenol biodegradation methods
Intermediates of phenol biodegradation and metabolic pathway
Phenol is converted by bacteria under aerobic conditions to carbon dioxide (Aquino et al. 1988) and under anaerobic conditions to carbon dioxide (Tschech and Fuchs 1987) or methane (Fedorak et al. 1986). The intermediates in the biodegradation of phenol are benzoate, catechol, cis, cis- muconate, ß-ketoadipate, succinate and acetate (Knoll and Winter, 1987). Phenol degradation by microbial pure and mixed cultures have been actively studied (Ahamad, 1995; Chang et al. 1998). Most of the cultures tested are capable of degrading phenol at low concentrations (Chang et al. 1998). Most studies on phenol degradation have been carried out with bacteria mainly from the Pseudomonas genus (Ahamad, 1995).
Phenol may be degraded in its free form as well as after adsorption onto soil or sediment, although the presence of sorbent reduces the rate of biodegradation. When phenol is the only carbon source, it can be degraded in a biofilm with first-order kinetics at concentrations below 20μg/L at 10ºC. The first-order rate constant are 3 to 30 times higher than those of easily degraded organic compounds and 100- 1000 fold at higher concentrations. Howard (1989) reported that phenol degradation rates suggest rapid aerobic degradation in sewage (typically 905 with an 8 h retention time), soil (typically complete biodegradation in 2-5 days), fresh water (typically biodegradation in <1 day), and sea water (typically 50% in 9 days). Anaerobic biodegradation is slower (Baker and Mayfield, 1980).
In bacteria, aromatic compounds are converted to few substrates: catechol, protocatechuate and more rarely gentisate. Representative aromatic compounds that are converted via catechol are shown in Fig. 1.
As mentioned earlier, bacteria play a major role in the degradation of phenol in soil, sediment and water. The number of bacteria capable of utilizing phenol is only a small percentage of the total population present in, for example, a soil sample (Hickman and Novak, 1989). However, a repeated exposure to phenol may result in acclimation as suggested by a number of researchers (Young and Rivera, 1985; Colvin and Rozich, 1986; Shimp and Pfaender, 1987; Wiggins and Alexander, 1988; Tibbles and Baecker, 1989a). Phenol may be degraded in its free form as well as after adsorption onto soil or sediment, although the presence of sorbent reduces the rate of biodegradation.
Phenol may be converted by bacteria by bacteria under aerobic conditions to carbondioxide and under anaerobic conditions to carbon dioxide or methane. The aerobic and anaerobic degradation of phenol has been studied extensively using various microorganisms. (Bak and Widdell, 1986; Karlsson et al. 1999; Ruiz-Ordaz et al. 2001; Mendoca et al. 2004; Yan et al. 2005)
Under aerobic condition, oxygen is used as electron acceptor for the transfer of electrons. The transfer of electrons between the electron-donor and electron-acceptor, substrates are essential for creating and maintaining biomass. For instance, in the biodegradation of phenol, phenol is the primary substrate and must be made available in order to have biomass active in the biodegradation process. According to Rittmann and Saez (1993) once active biomass is present, any biotransformation reaction can occur, provide the microorganisms possess enzymes for catalyzing the reaction. These enzymes that are involved in the aerobic metabolism of aromatic compounds usually define the range of substrates that can be transformed by certain metabolic pathway (Pieper and Reineke, 2000).
The first step in aerobic metabolism is phenol hydroxylation to catechol by phenol hydroxylase (EC 126.96.36.199) a NADPH-dependent flavoprotein (Neujahr and Gaal, 1973; Enroth et al. 1998). It incorporates one oxygen atom of molecular into the aromatic ring to form catechol. Phenol hydroxylases, strictly dependent on the presence of NADPH, have been described in extracts of T.cutaenum ( Neujhar and Gaal, 1973) and C. tropicalis (Neujhar et al. 1974). The second step is catalyzed by catechol 1,2-diooxygenase (EC 188.8.131.52; ortho fission ) or catechol 2,3-dioxygenase (EC 184.108.40.206; meta fission). After several subsequent steps, the products are incorporated into the Tricarboxylic acid cycle (TCA) or Krebs cycle (Shingler, 1996). It has been established that the aerobic degradation of phenolic compounds is metabolized by different strains through either the ortho- or the meta- cleavage pathway (Bayly and Barbour, 1984; Ahamad & Kunhi, 1996; Shingler, 1996).
A number of researchers (Shindo et al. 1995; Collins & Dauglis, 1997b; Fan et al. 1987; Livingstone and Chase, 1990) suggested that there are many possible biotechnological applications of aromatic- degrading organisms and their constituent enzymes have been investigated including the use in bioreactor systems for removal of toxic waste products or treatment of contaminated wastes. Other applications include the production of valuable biotransformation products such as picolinic acids from catechol (Asano et al. 1994), cis, cis-muconic acids from benzoic acid, benzene, toluene or catechol (Choi et al. 1997) and also as a reporter gene in diagnostic systems, for example, catechol 2, 3-dioxygenase gene as suggested by Shindo et al. (1995).
Determination of biomass concentration
With samples grown in batch culture, sampling was done periodically to determine the density. Cell density was monitored spectrophotometrically by measuring the absorbance at 600nm using the UVVIS Spectrophotometer.
The cell dry weight concentration was determined gravimetrically. 5ml aliquots were centrifuged for 15min at 15,000rpm at 10ºC in a pre-weighed 30ml tubes. The samples were washed twice with distilled water and the pellets were dried at 105ºC in an oven overnight. The difference between the first (empty) and the second weight was used to determine the dry weight of biomass as gm/L.
Dry cell weight was then estimated using calibration curve constructed based on the relationship between optical density at 600nm and dry weight cell.
Determination of specific growth rate
In a batch culture, the exponential increases in biomass after inoculation is measured as a function of time and analyzed to obtained specific growth rate (μ), for that substrate concentration (Yoong and Edgehill, 1993; Yoong et al. 2004).
The specific growth rate was measured from the slope of the biomass (dry weight) curve by delineating points between the log growth phase, represented by the equation below:
μ = (ln Xt – ln Xo) / t
Where Xo = Biomass concentration (dry weight) at time zero.
The process of biodegradation is a well-established and powerful technique for treating domestic and industrial effluents. Phenol degradation by Pseudomonas putida has been widely adopted. Many man-made organic compounds are also degraded by microorganism and there is an increase interest in the use of these organisms for pollution control. This paper can be extended by studying the optimization of the process of growth and degradation of phenol by the P.puitda using Box-Behnken design experiment, which works on regression analysis of the experimental data collected. The response methodology using the Box-Behnken design of experiments was used to develop a mathematical correlation between the parameters and degradation of phenol. The model predicted has been tested with the support of ANOVA.
- Abuhamed, T.A., Bayraktar, E., Mehmetoglu, T. and Mehmetoglu, U. 2003. Substrate interactions during the biodegradation of benzene, toluene and phenol mixtures. Process Biochemistry. 39 : 27-35.
- Ahamad, A.M. 1995. Phenol degradation by Pseudomonas aeruginosa. Environ. Sci. Health. 30 : 99-103.
- Ahamad, P.Y.A. and Kunhi, A.A.M. 1996. Degradation of phenol through ortho-cleavage pathway by Pseudomonas stutzeri strain SPCZ. Applied Microbiology Letters. 22 : 26-29.
- Alexander, M. 1985. Biodegradation of organic chemicals. Environ. Sci. Technol. 18 : 106-111.
- Alexieva, Z., Gerginova, M., Zlateva, P. and Peneva, N. 2004. Comparison of growth kinetics and phenol metabolizing enzymes of Trichosporoncutaneum R57 and mutants with modified degradation abilities. Enzyme Microbiology Technology. 34 : 242-247.
- Amoore, J.E. and Hautala, E. 1983. Odors as an aid to chemical safety: odor threshold limit values and volatilities for 214 industrial chemicals in air and water dilution. Appl. Toxicol. 3 : 272-290.
- Annadurai, G., MathalaiBalan, S. and Murugesan, T. 1999. Box-Behnken design in the development of optimized complex medium for phenol degradation using Pseudomonas putida (NICM 2174). Bioprocess Engineering. 21 : 415 - 421.
- Annadurai, G., Rajesh Babu, S. and Srinivasa Murthy, V. R. 2000. Mathematical modeling of phenol degradation system using fuzzy comprehensive evaluation. Bioprocess Engineering. 23 : 599-606.
- Aquino, M.D., Korol, S., Santini, P. and Moretton, J. 1988. Enzymatic synthesis of 4-hydroxybenzoic acid from phenol and carbondioxide: the first example of a biotechnological application of a carboxylase enzyme. Tetrehed. 54 : 8841-8846.
- Arquiaga, M.C., Canter, L.W. and Robinson, J.M. 1995. Microbiological characterization of the biological treatment of aircraft paint stripping waste water. Environ. Pollut. 89 : 189-195.
- ArianaFialova, ElkeBoschke and Thomas Bley. 2004. Rapid monitoring of the biodegradation of phenol-like compounds by the yeast Candida maltosa using BOD measurements. International Biodeterioration and Biodegradation. 54 (1) : 69-76.
- Arutchelvan,V., Kanakasabai, V., Nagarajan, S. and Muralikrishnan, V. 2005. Isolation and identification of novel high strength phenol degradaing bacterial strains from phenol-formaldehyde resin manufaturing industrial wastewater. Journal of Hazardous Materials. 238-243.
- Arutchelvan,V., Kanakasabai, V., Nagarajan, S. and Muralikrishnan, V. 2006.Kinetics of high strength phenol degradation using Bacillus brevis. Journal of Hazardous Materials. B129 : 216-222.
- Arzu, Y. Dursun, and Ozlem, Tepe 2005. Internal mass transfer effect on biodegradation of phenol by Ca-alginate immobilized Ralstoniaeutropha. Online.
- Asano, Y., Yamamota, Y. and Yamada, H. 1994. Catechol-2, 3-dioxygenase catalyzed synthesis of picolinic acids from catechols. Biosci. Biotechnol. Biochem. 58 : 2054-2056.
- Baek, S.H., Yin, C.R. and Lee, S.T. 2001. Aerobic nitrate respiration by newly isolated phenol degrading bacterium, Alcaligenes strain P5. Biotechnol. Lett. 23 : 627-630.
- Bak, F. and Widdell, F. 1986. Anaerobic degradation of phenol and phenol derivatives by Desulfobacteriumphenolicum, a new species. Arch. Microbiol. 146(2): 177-180.
- Baker, M.D. and Mayfield, C.I.1980. Microbial and non-biological decomposition of chlorophenols and phenol in soil. Wat. Air Soil Pollut. 13 : 411-424.
- Balasankar, T. and Nagarajan, S. 2000. Biodegradation of phenols by a plasmid free Bacillus brevis. Asian Journal of Microbiology, Biotechnology and Environmental Science. 2 (3-4) : 155-158.
- Bandhyopadhyaya, K., Das, D. and Maiti, B.R. 1998. Kinetics of phenol degradation using Pseudomonas putida MTCC 1194. Bioprocess Engineering. 18(5) : 373-377.
- Barker, E.L., Peter, E.B., Petrecia, H.F. and Grant, S.K. 1978. Phenol poisoning due to contaminated drinking water. Arch. Environ. Health. 33 : 89-94.
- Barkovskii, A.L., Korshunova, V.E. and Pozdnyacova, L.I. 1985. Catabolism of phenol and benzoate by Azospirillium strains. Applied Soil Ecol. 2 (1) : 17-24.
- Bastos, A.E.R., Tornisielo, V.L., Nozawa, S.R., Trevors, J.T. and Rossi, A. 2000a. Phenol metabolism by two microorganisms isolated from Amazonian forest soil amples. Indian Journal of Microbiology, Biotechnology. 24 (6) : 403-409.
- Bayly, R.C. and Barbour, M.G. 1984. The degradation of aromatic compounds by the meta and gentisate pathways: Biochemistry and regulation. In: Microbial Degradation of Organic Compounds (Gibson, D.T. ed.), Dekker, New York, pp. 253-293.
- Bhat, T.R., DivyaVenkataramani, Ravi, V. and Murty, C.V.S. 2006. An improved differential evolution method for efficient parameter estimation in biofilter modeling. Biochemical Engineering Journal. 28 : 167-176.
- Boopathy, R. 1995. Isolation and characterization of a phenol- degrading, sulfate-reducing bacterium from swine manure. Bioresearch Technology. 54 : 29-33.
- Boopathy, R.1997. Anaerobic phenol degradation by microorganisms of swine manure. Current Micorbiology. 35 : 64-67.
- Brown, V.M., Jordan, D.H.M. and Tiller, B.A. 1967. The effet of temperature on the acute toxicity of phenol to rainbow trout in hard water. Wat. Res. 1 : 587-97.
- Buitron, G. and Gonzalez, A. 1996. Characterization of the microorganisms from an acclimated activated sludge degrading phenolic compounds. Wat. Sci. Technol. 34 : 289-294.
- Capasso, R., Cristinzo, G., Evidnete, A. and Scognamiglio, F. 1992. Isolation, spectroscopy and selective phytotoxic effects of polyphenols from vegetable waste waters. Phytochem. 31 : 4125-4128.
- Chai, S.K., Das, S.B. and Bhaumik, G.C. 2004. Isolation of a phenol degrading culture and its application to remove phenols from coke oven plant effluent. Nature Environment Pollution Technology. 3 (3).
- Chang, S.Y., Li, C.T., Hiang. S.Y. and Chang, M.C. 1995. Intraspecific protoplast fusion of Candida tropicalis for enhancing phenol degradation. Appl. Microbiol. Biotechnol. 43 : 534-538.
- Chang, S.Y., Li, C.T., Chang, M.C. and Shieh, W.K. 1998. Batch phenol degradation by Candida tropicalis and its fusant. Biotechnol. Bioeng. 60 : 391-395.
- Chen, K.C., Lin, Y.H., Chen, W.H. and Liu, Y.C. 2002. Degradation of phenol by PAA-Immobilized Candida tropicalis. Enzyme Microbiology Technology. 31 : 490-497.
- Chirwa, E.N. and Wang, Y.T. 2000. Simultaneous chromium (VI) reduction and phenol degradation in an anerobic consortium of bacteria Water Research. 34 (8) : 2376-2384.
- Choi, W.J., Lee, E.Y., Cho, M.H. and Choi, C.Y. 1997. Enhanced production of cis,cismuconate in a cell-recycle bioreactor. FermBioeng. 84 (1) : 70-76.
- Collins, L.D. and Dauglis, A.J. 1997b. Characterization and optimization of a two phase partitioning bioreactor for the biodegradation of phenol. Appl. Microbiol. Biotechnol. 48 : 18-22.
- Colvin, R.J. and Rozich, A.R. 1986. Phenol growth kinetics of heterogenous populations in a two-stage continuous culture system. Wat. Pollut. Cont. Fed. 58 (4) : 326-332.
- Daraktchiev, R., Kolev, N. and Aleksandra, T.1996. A new bioreactor with a semi-fixed packing : investigation of degradation of phenol. Bioprocess Bioengineering. 16 : 5-7.
- DesoukyAbd-EI-Haleem, UsamaBeshay, Abdu O Abdelhamid, Hassan Moawad and Shar Zaki.2003. Effects of mixed nitrogen sources on biodegradation of phenol by immobilized Acinetobacter sp., strain W-17. African Jr. of Biotechnology. 2 (1) : 8-12.
- Duetz, W.A., Jong, C.D., Williams, P.A. and Van Andel, J.G. 1994. Competition in chemostat culture between Pseudomonas strains that use different pathways for the degradation of toluene. Appl. Environ. Micorbiol. 60 : 2858-2863.
- Ehlers, G.A. and Rose, P.D. 2004. Immobilized white-rot fungal biodegradation of phenol and chlorinates phenol in trickling packed-bed reactors by employing sequencing batch operation. Online.
- Enroth, C., Neujhar, H., Scheider, G. and Lindqvist, Y. 1998. The crystal structure of phenol hydroxylase in complex with FAD and phenol provides evidence for a concerted conformational change in the enzyme and its cofactor during catalysis. Structure. 6 (5) : 605-617.
- Ettayebi, K., Errachidi, F., Jamai, L., Tahri-Jouti, M.A., Sendide, K. and Ettayebi, M. 2003. Biodegradation of polyphenols with immobilized Candida tropicalis under metabolic induction. FEMS Microbiology Letters. 223 : 215-219.
- Evans, W.C. 1947. Oxidation of phenol and benzoic acid by some soil bacteria. Biol.Chem. 41 : 373 –382.
- Fan, L.S., Fujie, K., Long, T.R. and Tang, W.T. 1987. Characteristics of draft tube gas-liquid solid fluidized bioreactor with immobilized living cells for phenol degradation. Biotechnol. Bioeng. 30 : 498-504.
- Fedorak, P.M., Roberts, D.J. and Hrudey, S.E. 1986. The effects of cyanide on the methanogenic degradation of phenolic compounds. Wat. Res. 20 (10) : 1315- 1320.
- Fountoulakis, M.S., Dokianakis, S.N. and Kornaros, M.E. 2002. Removal of phenolics in olive mill wastewaters using the white-rot fungus Pleurotusostreatus. Water Research. 36 : 4735-4744.
- Francis FitzGibbon, Dalel Singh, Geoff McMullan and Roger Marchant. 1998. The effect of phenolic acids and molasses spentwash concentration on distillery waste water remediation by fungi. Process Biochemistry. 33 (8) : 799-803.
- Gabriele Pinto, AntoninoPollio, LucioPrevitera and Fabio Temussi. 2002. Biodegradation of phenols by microalgae. Biotechnology Letters. 24 : 2047-2051.
- Gabriela Vazquez-Rodriguez, Cherif Ben Yousseef and Julio Waissman-Vilanova. 2006. Two-step modeling of the biodegradation of phenol by an acclimated activated sludge. Chemical Engineering Journal.117: 245-252.
- Garcia Garcia, I., Bonilla Venceslada, J.L., Jimenez Pena, P.R. and Ramos Gomez, E. 1997. Biodegradation of phenol compounds in Vinasse using Aspergillusterreus and Geotrichumcandidum. Water Research. 31 (8) : 2005-2011.
- Garcia, I.G., Pena, P.R.J., Veneceslada, J.K.B., Santoz, A.A.M. and Gomez, E.R. 2000. Removal of phenol compound from olive mill wastewater using Phanerochaetechryososporium, Aspergillusniger, Aspergillusterreus and Geotrichumcandidum. Process Biochemistry. 35 : 751-758.
- Gardener, W., Cooke, E.I. and Cooke, R.W.I. 1978. Handbook of Chemical Synonyms and Trade Names. Boca Raton, FL: CRC Press.
- Gehomg Wei, Jianfu Yu, Yuhua Zhu, Weimin Chen and Li Wang. 2007. Chracterization of phenol degradation by Rhizobium sp., CCNWTB 701 isolated from Astragaluschrysopteru in mining tailing region. Journal of Hazardous Materials. 1-7
- Girolami, V., Vianello, A., Stuparon, A., Ragazzi, E. and Veronese, I. 1981. Ovipositional deterrents in Dacusoleae. Entom. Exp. Appl. 29: 178-185.
- Gonzalez,D.M., Moreno, E., Sarmiento, J.Q. and Ramos- Cormenzana, A. 1990. Stuides on antibacterial activity of waste waters from olive mills (Alpechin): Inhibitory activity of phenolic and fatty acids. Chemo sp. 20 : 423-432.
- Gonzalez, G., Herrera, M.G., Garcia, M.T. and Pena, M. 2001a. Biodegradation of phenol in a continuous process: Comparative study of stirred tank and fluidized -bed bioreactors. Bioresearch Technology. 76 : 245-251.
- Guiraud, P., Steiman, R., Ait-Laydi, L. and Seigle-Muranid, F. 1999. Degradation of phenolic and chloroaromatic compounds by Corprinus sp. Chemosphere. 38 (12) : 2775-2789.
- GurusamyAnnadurai, Lai Yi Ling and Jiunn – Fwu Lee. 2007. Statistical optimization of medium components and growth conditions by response surface methodology to enhance phenol degradation by Pseudomonas putida.
- Ha,S.R., Vinitnantharat, S. and Ozaki,H. 2000. Biodegradation by mixed microrganisms of granular activated carbon loaded with a mixture of phenols. Biotechnology Letters. 22 : 1093-1096.
- Harris, G. And Ricketts, R.W. 1962. Metaboilsm of phenolic compounds by yeasts. Nat. 195 : 473-474. Hashimoto, K. 1973. Oxidation of phenols by yeast. II. Oxidation of cresol by Candida tropicalis. Gen. Appl. Micorbiol. 19 : 171-187.
- Heilbuth, N.M., Linardi, V.R. and Santos, V.L. 2003. Phenol biodegradation by free and immobilized cells of Acinetobacterjohnsonii. M.Sc. thesis, Instituto De CienciasBiologicas/Pos-Graduacao. Enn. Eco-1 Eco-1 24 CHANDANA LAKSHMI AND SRIDEVI A REVIEW ON BIODEGRADATION OF PHENOL FROM INDUSTRIAL EFFLUENTS 25 Microbiologia.
- Henderson, M.E.K. 1961. The metabolism of aromatic compounds related to lignin by some Hyphomycetes and yeast-like fungi of soil. Gen. Micorbiol. 26 : 155-165.
- Hickman, G.T. and Novak, J.T. 1989. Relationship between subsurface biodegradation rates and microbial density. Environ. Sci. Technol. 23 (5) : 524-532.
- Hinteregger, C., Leitner,R., Loidl,M., Ferschl, A. and Streichsvier, F. 1992. Degradation of phenol and phenolic compounds by Pseudomonas putida EKII. Applied Microbiology Biotechnology. 37 : 252-259.
- Hintereggerr, C. and Streichsbier, F. 1997. Halomonas sp. A moderately halophilic strain for biotreatment of saline phenolic wastewater. Biotechnology Letters. 19 : 1099-1102.
- Howard, P.H. 1989. Handbook of Environmental Fate and Exposure Data for Organic Chemicals. Chelesa, Michigan, Lewis Publishers. 1 : 468-476.
- Hughes, S.M. and Cooper, D.G. 1996. Biodegradation of phenol using the self - cycling fermentation (SCF) process. Biotechnology Bioengineering. 51 : 112-119.
- Hutchinson, D.H. and Robinson, C.W. 1988. Kinetics of the simultaneous batch degradation of p-cresol and phenol by Pseudomonas putida. Appl. Microbiol. Biotechnol. 29 : 599-604.
- JolantaBohdziewicz, 1998. Biodegradation of phenol by enzymes from Pseudomonas sp. immobilized onto ultrafiltration membranes. 33 (8) : 811-818.
- Kanekar, P.P., Sarnaik, S.S. and Kelkar, A.S. 1999. Bioremediation of phenol by alkaline bacteria isolated from alkaline lake of Lonar, India. Applied Micorbiology. 85 :128S-133S.
- Kang, M.H. and Park, J.M. 1997. Sequential degradation of phenol and cyanide by a commensal interaction between two microorganisms. Chemical Technology Biotechnology. 69 : 226-230.
- Kar, S., Swaminathan, T. and Baradarajan, A. 1996. Studies on biodegradation of a mixture of toxic and non toxic pollutant using Anthrobacter species. Bioprocess Engineering. 15 (4) : 195-199.
- Karlsson, A., Ejlertsson, J., Nezirevic. D. and Svenson, B.H. 1999. Degradation of phenol under meso- and thermophilic anaerobic conditions. Anaer. 5 :25-35.
- Katayama-Hirayama, K., Tobita, S. and Hirayama, K. 1994. Biodegradation of phenol and monochlorophenols by yeast Rodotorulaglutinis. Water science Technology. 30 : 59-66.
- Kavitha, G.V. and ShaikKhasimBeebi. 2003. Biodegradation of phenol in packed-bed reactor using peat media. Asian Journal of Microbiology, Biotechnology and Environmental Science. 5 (2) : 157-159.
- Kim, J.H., Oh, K.K., Lee, S.T., Kim, S.W. and Hong, S.I. 2002. Biodegradation of phenol and chlorophenol with defined mixed culture in shake-flasks and a packed bed reactor. Process Biochemistry. 37 : 1367- 1373.
- Kiyohara, H., Hatta, T., Ogawa, Y., Kakuda, T., Tokoyama, H. and Takizawa, N. 1992. Isolation of Pseudomonas picketti strains that degrade 2,4,6- trichloro-phenol and their dechlorination of chlorophenols. Appl. Environ. Microbiol. 58 : 1276-1283.
- Klein, J., Hackel, U. and Wagner, F. 1979. Phenol degradation by Candida tropicalis whole cells entrapped in polymeric ionic networks. ACS Symp. Ser. 106 : 101-118.
- Knoll, G. and Winter, J. 1987. Anaerobic degradation of phenol in sewage sludge: benzoate formation from phenol and carbondioxide in the presence of hydrogen. Appl. Microbiol. Biotechnol. 25 (4) : 384-391.
- Ko-ichiOshiman, YuziTsutsumi, Tomoaki Nishida and Yoshinobu Matsumura. 2007. Isolation and characterization of a novel bacterium Sphingomonasbisphenolicum strain AO1, that degrades bisphenol A. Biodegradation. 18 : 247-255.
- Komarkova, E., Paca, J., Klapkova, E., Stiborova, M., Soccol, C.R. and Sobotka, M. 2003. Physiological changes of Candida tropicalis population degrading phenol in fed batch reactor. Braz. Arch. Biol. Technology. 46 (4) : 537-543.
- Kotturi,G., Robinson, C.W. and Inniss, W.E. 1991. Phenol degradation by psychotrophic strain of Pseudomonas putida. Applied Microbiology Biotechnology. 34 : 539-543.
- Kowalska, M., Bodzek, M. and Bohdziewicz, J. 1998. Biodegradation of phenols and cyanides using membranes with immobilized microorganisms. Process Biochemistry. 33 (2) : 189-197.
- Krug, M. and Straube, G. 1986. Degradation of phenolic compounds by the yeast Candida tropicalis HP-15. II. Some properties of the first two enzymes of the degradation pathway. Basic Microbiology. 26 (5) : 271-281.
- Krug, M., Ziegler, H. and Straube,G. 1985. Degradation of phenolic compounds by the yeast Candida tropicalis HP-15. I. Physiology and growth and substrate utilization. Basic Microbiology. 25 (2) : 103-110.
- Kumaran, P. 1980. Microbial degradation of phenol in phenol- bearing industrial wastes. Ph.D. thesis, Nagpur. Kumaran, P. and Parachuri, Y.L. 1997. Kinetics of phenol biotransformation. Wat. Res. 31 : 11-22.
- Lappin, H.M., Greaves, M.P. and Slatter, J.H. 1985. Degradation of the herbicide [2-(2-Methyl-4-Chlorophenoxy) Propionic Acid by a synergistic microbial community. Appl. Environ. Micorbiol. 49 : 429-433.
- Leonard, D. and Lindely, N.D. 1999. Growth of Ralstonieutropha on inhibitory concentrations of phenol- diminished growth can be attributed to hydrophobic perturbation of phenol hydroxylase activity. Enzyme Microbiology Technology. 25 : 271-277.
- Letouneau, L., Bisaillon, J.G., Lepine, F. and Beaudet, R. 1995. Spore-forming bacteria that carboxylate phenol to benzoate acid under anaerobic conditions. Can. Micorbiology. 41 : 266-272.
- Lide, D.R. 1993. CRC Handbook of Chemistry and Physics. Boca Raton, FL:CRC Press.
- Livingston, H. and Chase, H.A. 1990. Development of a phenol degrading fluidized-bed bioreactor for constant biomass holdup. Chem. Eng. 45 : 1335-1347.
- Loh, K.C. and Liu, J. 2001. External loop inversed fluidized bed airlift bioreactor (EIFBAB) for treating high strength phenolic wastewater. Chemical Engineering Science. 56 : 6171-6176.
- Lovley.D.R. and Lonergan, D.J. 1990. Anaerobic oxidation of toluene, phenol and p-cresol by the dissimilatory iron-reducing organism GS-15. Applied Microbiology Biotechnology. 56 (6) : 1858.
- Mahadevaswamy, M., Mishra, I.M., Prasad, B. and Mall, I.D. 2004. Kinetics and biodegradation of phenol. In: Ujang, Z. and Henze. M. (Eds.). Environmental Biotechnology: Advancement in Water and Wastewater application in the tropics. Water Environment Management. Ser. 85-92.
- Manahan, S.E. 1994. Environmental Chemistry. Boca Raton. FL:CRC Press. Masuda, M., Sakurai, A. and Sakakibara, M. 2001. Effect of enzyme impurities on phenol removal by the method of polymerization nad precipitation catalyzed by Coprinuscinereus peroxidase. Applied Microbiology Biotechnology. 57 : 494-499.
- Mendoca, E., Martins, A. and Anselmo, A.M. 2004. Biodegradation of natural phenolic compounds as single and mixed substrates by Fusariumflocciferum. Electro. Biotechnol. 7 (1) : 30-37.
- Mette M. Broholm, Erik Arvin. 2000. Biodegradation of phenols in a standstone aquifer under aerobic conditions and mixed nitrate and iron reducing conditions. Journal of Contaminant Hydrology. 44 : 239-273.
- Monterio, A.A.M., Boaventura, R.A.R. and Rodriguez, A.E. 2000. Phenol degradation by Pseudomonas putida DSM 548 in a batch reactor. Biochemical Engineering. 6 : 45-49.
- Motzkus, C., Welge, G. and Lamprecht, I. 1993. Calorimetric investigations of phenol degradation by Pseudomonas putida. Thermochem. Acta. 229 : 181-192.
- Moustafa EI-Sayed, A.E.S. 2003. Biological degradation of substrate mixtures composed of phenol, benzoate and acetate by Burkholderiacepacia G4. Ph.D. thesis, Biochemical Engineering Journal. Div. Braunschweig, Germany.
- Mutzel,A., Reinschied, U.M., Autranikian, G. and Muller, R. 1996. Isolation and characterization of a thermophilic Bacillus strain, that degrade phenol and cresol as sole carbon source at 70ºC. Applied and Environmental Microbiology. 46 : 593-596.
- Nakamura, Y. and Sawada, T. 2000. Biodegradation of phenol in the presence of heavy metals. Chemical Technology Biotechnology. 75 : 135-142.
- Neujahr, H.Y. and Gaal, A. 1973. Phenol hydroxylase from yeast. Purification and properties of the enzyme from Trichosporoncutaneum. Eur. Biochemistry. 35 : 386-400.
- Neujahr, H.Y. and varga, J.M. 1970. Degradation of phenols by intake cells and cell-free preparations of Trichosporoncutaneum. Eur. Biochem. 13 : 37-44.
- Neujahr, H.Y., Lindsjo, S. and Varga, J.M. 1974. Oxidation of phenol by cells and cell-free enzymes from Candida tropicalis. Antonie van Leeuwenhoek. 40: 209-216.
- Nurk, A., Kasak, I., and Kivissar, M. 1991. Sequence of the gene (PhEA) encoding phenol monooxygenase from Pseudomonas sp. Est 1001-expression in Escherichia coli and Pseudomonas putida. Gene. 102: 13-18.
- Oliver J. Hao, Michael H. Kim, Eric A. Seagren and Hyunook Kim. 2002. Kinetics of phenol and chlorophenol utilization by Acinetobacter species. Chemosphere. 46 : 797-807.
- Onsyko, K.A., Robison, C.W. and Budman, H.M. 2002. Improved modeling of the unsteady-state behavior of an immobilized–cell, fluidized-bed Bioreactor for phenol biodegradation. Chemical Engineering. 80 : 239-252.
- Orupold K., Tenno, T. and Henrysson, T. 2000. Biological lagooning of phenols-containing oil shale ash heaps leachate. Water Research. 34 (18) : 4389-4396.
- OzlemTepe and Arzu Y. Dursun. 2007. Combined effects of external mass transfer and biodegradation rates on removal of phenol by immobilized Ralstoniaeutropha in a packed bed reactor. Online.
- Pai, S.L., Hsu, Y.L., Chong, N.M., Sheu, C.S. and Chen, C.H. 1995. Continuous degradation of phenol by Rhodococcus sp. immobilized on granular activated carbon and in calcium alginate. Bioresearch Technology. 51: 37-42.
- Parales, R.E., Bruce, N.C., Schmid, A. and Wackett, L.P. 2002. Biodegradation biotransformation, and biocatalysis (B3). Appl. Environ. Microbiol. 68 (10) : 2699-4709.
- Pekari, K., Vaintalo, S., Heikkila,P., Palotie, A., Luotamo, M. and Riihimaki, V. 1992. Biological monitoring of occupational exposure to low levels of benzene. Scand. Work Environ. Health. 18: 317-322.
- Peyton, B.M., Wilson, T. and Yonge, D.R. 2002. Kinetics of phenol degradation in high salt solutions. Water Research. 36: 4811-4820.
- Piakong Bin Mohd. Tuah. 2006. The response of phenol biodegradation by Candida tropicalis RETL-Cr1 using Batch and Fed-batch fermentation techniques. Ph.D. thesis. UniversitiTeknologi Malaysia. Pieper, D.H. and Reineke, W. 2000. Engineering bacteria for bioremediation. Curr. Opin. Biotechnol. 11 (3): 262-270.
- Prieto, M.B., Hidalgo, A. Serra, J.L. and Llama, M.J. 2002. Degradation of phenol by Rodococcuserythropolis UPV-1 immobilized on biolight in a packed –bed reactor. Biotechnology. 97 : 1-11.
- Puhakka, J.A., Herwig, R.P., Koro, P.M., Wolfe, G.V. and Ferguson, J.F. 1995. Biodegradation of chlorophenols Eco-1 Eco-1 26 CHANDANA LAKSHMI AND SRIDEVI A REVIEW ON BIODEGRADATION OF PHENOL FROM INDUSTRIAL EFFLUENTS 27 by mixed and pure cultures from a fluidized bed reactor. Appl. Microbiol. Biotechnol. 42 : 951-957.
- Reardon, K.F., Mosteller, D.C. and Rogers, J.D. 2000. Biodegradation kinetics of benzene, toluene and phenol in single and mixed substrate for Pseudomonas putida F1. Biotechnology Bioengineering. 69 : 385-400.
- Rittmann, B.E. and Saez, P.B. 1993. Modeling biological processes involved in degradation of hazardous organic substrates In: Levin, M.A. and Gealt, M.A. (eds.) Biotreatment of Industrial and Hazardous Waste. McGraw Hill, Inc. New York. 113-119.
- Rogers, J.B. and Reardon, K.F. 2000. Modeling substrate interactions during the biodegradation of mixture of toluene and phenol by Burkholderia species JS 150. Biotechnology Bioengineering. 70 : 428-435.
- Ruiz-Ordaz, N., Juarez Ramirez, J.C., Castonon-Gonzalez, H., Lara-Rodriguez, A.R., Christiani-Urbina, E. nadGalindez-Mayer, J. 2000. Aerobic bioprocesses and bioreactors used for phenol degradation by free and immobilized cells. In: Pandalai, S.G. (ed.) Recent Research Developments in Biotechnol. and Bioeng. Res. Signpost. Triv. India. 83-94.
- Ruiz-Ordaz,N., Ruiz-Lagunez, J.C., Castanon-Gonzalez, J.H., Hernandez Manzano, E., Christiani –Urbina, E. and Galindez-Mayer, J. 2001. Phenol biodegradation using repeated batch culture of Candida tropicalis in a multistage bubble column. RevistaLatinoamericana de Microbiologia. 43 : 19-25.
- Safia Ahmed, M., AfzalJaved, ShaziaTanvir and Abdul Hameed. 2001. Isolation and characterization of a Pseudomonas strain that degrades 4-acetamidophenol and 4-aminophenol. Biodegradation. 12: 303-309.
- Salmeron-Alcocer, A., Ruiz-Ordaz, N., Juarez-Ramirez, C. and Galindez-Mayer, J. 2007. Continuous biodegradation of single and mixed chlorophenols by a mixed microbial culture constituted by Burkholderia sp., Microbacteriumphyllosphaerae& Candida tropicalis. Biochemical Engineering Journal. 1-11.
- Santiago Esplugas, Jaime Gimenez, Sandra Contreras, Esther Pascual and Miguel Rodriguez. 2002. Comparison of different advanced oxidation processes for phenol degradation. Water Research. 36 : 1034-1042.
- Santos V.L., and Valter R. Linardi. 2004. Biodegradation of phenol by a filamentous fungi isolated from industrial effluents-identification and degradation potential. Process Biochemistry. 39 (8) : 1001-1006.
- Seetharam, G.B. and Saville, B.A. 2003. Degradation of phenol using tyrosinase immobilized on siliceous supports. Wat. Res. 37 : 436-440.
- Seker, S., Beyenal, H., Salih, B. and Tanyolac, A. 1997. Multi-substrate growth kinetics of Pseudomonas putida for phenol removal. Applied Microbiology Biotechnology.47 : 610-614.
- Semple, K.T. and Cain, R.B. 1995. Metabolism of phenols by Ochoromonasdanica. FEMS Microbiology Letters. 133 : 253-257.
- Sheeja, R.Y. and Murugesan, T. 2002. Mass Transfer studies on the biodegradation of phenol in up-flow packed bed reactors. Hazardous Materials. B89 : 287-301.
- Shimp, R.J. and Pfaender, F.K. 1987. Effect of adaptation to phenol on biodegradation of monosubstituted phenols by aquatic microbial communities. Appl. Envrion. Micorbiol. 53 (7) : 1496-1499.
- Shimizu, T., Uno,T. Dan, Y., Nei, N. and Ichikawa, K. 1973. Continuous treatment of wastewater containing phenol by Candida tropicalis. Fermentation Technology. 51 : 804-812. Shindo, T., Ueda, H., Suzuki, E., and Nishimura, H.A. 1995. Catechol-2, 3-dioxygenase gene as a reporter. Biosci. Biotechnol. Biochem. 59 : 314-315.
- Shingler, V. 1996. Molecular and regulatory checkpoints in phenol degradation by Pseudomonas sp. CP600. In: Nakazawa, T., Furukawa, K., Haas, D. and Silver, S. (eds.) Molecular Biology of Pseudomonads. Am. Soc. Micorbiol. Washington, D.C. 153-164.
- Shinoda, T., Sakai, Y., Ue, M., Hiraishi, A. and Kato, N. 2000. Isolation and characterization of a new denitrifying spirillium capable of anaerobic degradation of phenol. Applied and Environmental Microbiology. 66 (4) : 1286-1291.
- Soda, S., Ike, M. and Fujita, M. 1998. Effects of inoculation of a genetically engineered bacterium on performance and indigenous bacteria of a sequencing batch activated sludge process treating phenol. Fermentation Bioengineering. 86 (1) : 90-96.
- Spain, J.C. and Gibson, D.T. 1988. Oxidation of substituted phenols by Pseudomonas putida F1 and Pseudomonas sp. Strain JS6. Applied Environmental Microbiology. 1399-1404.
- Stephenson, T. 1990. Substrate inhibition of phenol oxidation by a strain of Candida tropicalis. Biotechnology Letters. 12 : 843-846.
- Tarik Abu Hamed, EmineBayarktar, TanjuMehmetogiu and UlkuMehmetoglu. 2003. Substrate interactions during the biodegradation of benzene, toluene and phenol mixtures. Process Biochemistry. 39 : 27-35.
- Tibbles, B.J. and Baecker, A.A.W. 1989a. Effects and fate of phenol in simulated landfill sites. Microb. Ecol. 17 (2) : 210-206.
- Tibbles, B.J. and Baecker, A.A.W. 1989b. Effect of pH and inoculum size on phenol degradation by bacteria isolated from landfill waste. Environmental Pollution. 59 (3) : 227-239.
- Tscheh, A. and Fuchs, G. 1987. Anaerobic degradation of phenol by pure cultures of newly isolated denitrifying Pseudomonads. Arch. Microbiol. 148 (3) : 213-217.
- Tsuey-Ping Chung, Pei-Chen Wu, Ruey-Shin Juang, 2005. Use of microporous hallow fibres for improved biodegradation of high-strength phenol solutions. Journal of Membrane Science. 258 : 55-63.
- Tziotzios, G., Economou, Ch.N., Lyberatos, G. and Vayenas, D.V. 2007. Effect of the specific surface area and operating mode on biological phenol removal using packed-bed reactors. Desalination. 211 : 128-137.
- UsamaBeshay, Desouky, Abd-EI-Haleem, Hassan Moawad and SaharZaki. 2002. Phenol biodegradation by free and immobilized Acinetobacter. Biotechnology Letters. 24 : 1295-1297.
- VenuVinod, A. and Venkat Reddy, G. 2005. Simulation of biodegradation process of phenolic wastewater at higher concentrations in a fluidized-bed reactor. Online.
- Vijaygopal, V. and Viruthagiri, T. 2005. Batch kinetic studies in phenol biodegradation and comparison. Indian Journal of Biotechnology. 4 : 565-567.
- Wang, S.J. and Loh, K.C. 1999. Modeling the role of metabolic intermediates in kinetics of phenol biodegradation. Enzyme. Microbiology Technology. 25 : 177-184.
- Watanabe, K., Hino, S. and Takahashi, N. 1996a. Effects of exogenous phenol degrading bacteria performance on ecosystem of activated sludge. Fermentation Bioengineering. 82 (3) : 291-298.
- WeijianCai, Jiwu Li and Zhen Zhang. 2007. The characteristics and mechanisms of phenol biodegradation by Fusarium species. Online.
- Whiteley, A.S., Wiles, S., Lilley, A.K., Phillip, J. and Bailey, M.J. 2001. Ecological and physiological analyses of Pseudomonads species within a phenol remediation system. Microbiol. Met. 44 : 79-88.
- Wiggins, B.A. and Alexander, M. 1988. Role of chemical concentration and second carbon sources in acclimation of microbial communities for biodegradation. Appl. Environ. Microbiol. 54 (11) : 2803-2807.
- World Health Organization (WHO), 1994. Phenol, Environmental health criteria- EHC 161, WHO, Geneva. Yan Jiang , Jianping Wen, XiaoqiangJia, QianggeleCaiyan and Zongding Hu. 2007. mutation of Candida tropicalis by irradiation with a He-Ne laser to increase its ability to degrade phenol. Applied Microbiology Biotechnology. 73 (1) : 226-231.
- Yan, J., Jianping, W., Hongmei, L., Suliang, Y. and Zongding, H. 2005. The biodegradation of phenol at high initial concentration by yeasts Candida tropicalis. Biochemical Engineering. 24 (3) : 243-247.
- Yap, L.F., Lee, Y.K. and Poh, C.L. 1999. Mechanism for phenol tolerance in phenol degrading Comamonastestosteroni strain. Applied Microbiology Biotechnology. 5 (6) : 833-840.
- Yoong, E. and Edgehill, R. 1993. Inhibitory substrate biodegradation using acclimated municipal activated sludge. Proc. 15th Fed. Conv. AWWA. Gold Coast, Queensland 18-23 April 1993, 635-639.
- Yoong, E.T., Staib, C.I. and Lant, P.A. 2004. Kinetics coefficients of high strength phenolic wastewater biodegradation. In: Ujang, Z. and Henze, M. Young, L.Y. and Rivera, M.D. 1985. Methanogenic degradation of 4 phenolic compounds. Wat. Res. 19 (10) : 1325-