Article pubs.acs.org/jced
Investigation of Extraction of Phenol from Wastewater Using N,N‑Didodecyl-1-dodecanamine (Tridodecylamine) in Benzene Dipaloy Datta*,† and Hasan Uslu‡ †
Department of Chemical Engineering, Thapar University, Patiala, 147004, India Engineering and Architecture Faculty, Chemical Engineering Department, Beykent University, Ayazağa, Iṡ tanbul, 34433, Turkey
‡
ABSTRACT: Tridodecylamine (TDDA) is used as an extractant in benzene for the separation of phenol from the aqueous streams generated from industrial effluents. The effects of aqueous solution pH (at five different pH values, 3 to 11) and concentration of TDDA (at three different compositions, 100 w = 5 to 100 w = 20) in the organic phase are investigated on the distribution coefficient (D). Results show that the neutral phenol molecule is effectively extracted by TDDA into the organic phase by H-bonding. A maximum value of D (5.027, 83.41 %E) is observed at equilibrium pH of 5 and at highest concentration of TDDA (100 w = 20). A mathematical expression for equilibrium D is proposed based on the mass action law, and the apparent equilibrium constants (K) and the stoichiometric coefficient (n) are estimated from the regression of the experimental data. The K and n are found to be 10.17 and 0.60, respectively, at pH of 5. The D values are also predicted and show a good agreement with R2 > 0.99 and SD < 0.0141.
1. INTRODUCTION Phenolic compounds are considered to be environmental pollutants because of their toxicity and carcinogenic effect. They are found in the industrial effluent streams of petroleum refineries, coal mining and gasification, pharmaceutical production, steel and iron manufacturing, tanning and finishing of leather, sebacic acid manufacturing, resin production, pulp and paper industries, wood product industries, and paint and antiseptics.1−4 Their concentrations in such effluents vary from 100 ppm to several percentages. Among phenolic compounds, phenol is harmful and toxic to human health even at very low concentrations. The use of phenol contaminated water by a human can cause severe pain and damage of the capillaries ultimately causing death.5 Chlorine in drinking water converts phenol to chlorophenol which has a medicinal taste that is quite pronounced and objectionable. Bisphenol A, an endocrine disrupting chemical, has been known to be an estrogenic compound since the mid 1930s.6 It acts as a hormone in living human and animal bodies and may prove hazardous to human health and the ecosystem.7 In September 2010, Canada became the first country to declare bisphenol A as a toxic substance.8 The other important polluting phenolic compound is p-nitrophenol, which is known to be persistent, bioaccumulative, and highly toxic. p-Nitrophenol aids in converting hemoglobin to methamoglobin, that is, oxidation of iron(II) to iron(III) reducing the oxygen transport capacity of hemoglobin in the body.9 Aminophenols are key components in industrial effluent from printing and dyeing mills, which are not biodegradable and have serious toxic and contaminative effects.10 Phenols are produced in very large quantities for use as solvents and starting materials for chemical synthesis. Phenolic compounds are some of the major hazardous compounds in industrial wastewater because of their poor biodegradability, © 2014 American Chemical Society
high toxicity, and ecological aspects. For instance, phenols are released into water from industrial effluent discharges such as petroleum refinery wastewater.11 It has also been detected in groundwater as a result of leaching through the soil after a spill of phenol from landfill sites. Typical wastewaters from oil refineries contain phenol in concentrations ranging from 500 ppm to 1500 ppm, and those from coking plants in concentrations ranging from 200 ppm to 1200 ppm. The presence of phenol in drinking water and irrigation water represents a serious health hazard to humans, animals, plants, and microorganisms. Because of the high toxicity of phenols, they are subjected to specific regulations. The Environmental Protection Agency (EPA) calls for lowering phenol content in potable and mineral waters to 0.5 ppb, while the limits for wastewater discharge are 0.5 ppm for surface waters and 1 ppm for the sewage system.11 According to the Health and Safety Guide No 88, phenol is toxic and has a carcinogenic effect. Therefore, release of phenol to the environment may cause concern for the health of human and aquatic lives. The concentrations of phenol in industrial effluents are normally in a range of 2.8 ppm to 6800 ppm which is much higher than the median lethal dose (LD50) for aquatic lives. This gives an adverse effect and disrupts the aquatic ecosystem balance. The Department of Environment, Malaysia, has set a maximum phenol discharge concentration of 1 ppm. Thus, there is an urgent need to find an effective method for the treatment of wastewater containing phenol. Several methods have been developed to remove phenol from wastewater, including microbial degradation, chemical oxidation, photocatalytic Received: August 13, 2014 Accepted: October 21, 2014 Published: November 3, 2014 3858
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Table 1. Physical Characteristics of Chemicals Used in the Study chemical
molar mass (g/mol)
molecular formula
suppliers
CAS No.
purity (% GC)
phenol benzene tridodecylamine
94.11 78.11 521.99
C6H5OH C6H6 C36H75N
Merck, India CDH, India Sigma-Aldrich, India
108-95-2 71-43-2 102-87-4
98.0 99.8 95.0
the reactive extraction of phenol is studied. This study is a complementary study for the above-mentioned literature.
degradation, ultrasonic degradation, enzymatic polymerization, membrane separation, solvent extraction, adsorption, and steam-distillation.12−24 In India, the desirable limit of phenolic compounds in the drinking water as phenol is 0.001 ppm, the limit in the effluents of land water is 1 ppm, and the limit in the sewer discharge is 5 ppm.25 The phenolic compounds are also used in the production of many chemicals such as dyes, adhesives, germicides, and chemical intermediates26 and thus are considered as valuable chemicals. Therefore, the recovery of these compounds is important and results in achieving two main objectives: (i) prevention of environmental pollution, and (ii) obtaining valuable phenolic compounds.27 The destructive methods include biological treatments,28 incineration, ozonization in the presence of UV radiation, oxidation with wet air,29 and electrochemical oxidation.30 Alternately, the recovery methods include liquid−liquid extraction,31 adsorption,32 extraction with membrane,33 and supported liquid membrane.1,34 Phenol removal and recovery by liquid−liquid extraction, which started to be used during the Second World War,35 is economically feasible with respect to other techniques when phenolic effluents are highly concentrated (>1000 ppm) and/or released at high flow rates.36 Reactive extraction has a high capacity and high selectivity to separate polar organic solutes from dilute aqueous solutions. It has received increasing attention because of its simple methodology and low cost. Cui et al.10 investigated separation of o-aminophenol from wastewater. Tri-n-butyl phosphate (TBP) was used as the extraction agent for the removal of o-aminophenol (OAP) in active solvents and inactive solvents. The effects of aqueous solution pH, solvents, concentration of TBP, and the initial OAP concentration on distribution coefficient (D) were investigated. The active solvents used were octan-1-ol and chloroform and inactive solvents used were carbon tetrachloride and kerosene. The trend in D value in the case of different solvents was observed to be octane-1-ol > chloroform > carbon tetrachloride = kerosene. The value of dissociation constant increased as the concentration of extractant, TBP, increased. The value of D decreased as the initial concentration of OAP increased. Chang et al.21 investigated reactive extractions of o-, m-, and p-aminophenol (OAP, MAP, and PAP) using the trialkylphosphine oxide/kerosene (TRPO/kerosene) system. The organic phases used were pure kerosene and TRPO in kerosene with concentrations of (0.2338, 0.4676, 0.7014, and 1.169) mol·kg−1. The D value was found to increase with an increase in pH for all organic phase compositions. The equilibrium aqueous phase pH and the concentrations of TRPO in the organic phase were found to be important factors and affected significantly the values of D for the extraction of OAP, MAP, and PAP using the TRPO/kerosene extraction system. Infrared spectra results suggested that pHeq had no influence on the complexes’ structures, and TRPO mainly reacted with neutral aminophenol through forming a hydrogen bond between its PO and aminophenol OH. In this study, the reactive extraction of phenol by amine extractant, tridodecylamine (TDDA) from aqueous solution is investigated. The effect of pH and extractant concentration on
2. MATERIALS AND METHODS 2.1. Chemicals. The properties of the chemicals [tridodecylamine (TDDA), benzene, phenol, sulfuric acid, and sodium hydroxide] used in this study are presented in Table 1. TDDA was used as the medium to extract phenol from the aqueous solution with benzene as the diluting agent. Further, the pH of the solution was maintained by appropriately mixing sodium hydroxide (1 N) or sulfuric acid (0.5 N) solutions. 2.2. Experimental Procedure. The extraction equilibrium experiments were carried out at constant temperature (298 ± 1 K). The pH is adjusted using 0.5 N H2SO4 and 1 N NaOH with the help of a pH meter (±0.1). Now, a 20 mL sample of 100 ppm solution of phenol in water was prepared. The organic phase of TDDA was prepared with 100 w = 5 TDDA and 100 w = 95 benzene (an organic solvent). A 20 mL aliquot of this sample was mixed with the phenolic solution (20 mL) and left to attain equilibrium, and then the phases were separated. The time considered for shaking and settling were 6 and 2 h, respectively, using a shaking machine (HS 250, Remi Laboratories, India). The equilibrium experiments were also carried out with 100 w = 10 TDDA + 100 w = 90 benzene, and 100 w = 20 TDDA + 100 w = 80 benzene. The above samples were used to perform experiments using different sets of pH at 3, 5, 7, 9, and 11. The aqueous phase was analyzed for residual phenol concentration at equilibrium by using a UV−vis spectrophotometer (Evolution 201, Thermo Fisher Scientific, India) at 270 nm. The results were found to be reproducible within the error limit of ± 5 %. 3. RESULTS AND DISCUSSION The equilibrium experiments were performed in batch mode at 298 ± 1 K. The results obtained, that is, the measured values of aqueous and organic phase concentrations of phenol, were utilized to calculate the distribution coefficient (D) and degree of extraction (%E) and expressed by eqs 1, and 2, respectively. The distribution coefficient of phenol (HA) by TDDA between extract and water phase can be obtained from the ratio of total concentration of phenol in the organic phase (C̅ HA) to the aqueous phase (CHA) at equilibrium, eq 1. D=
C̅ HA C HA
(1)
The degree of extraction (%E) at equilibrium is found from the expression as shown in eq 2. %E =
D 100 1+D
(2)
Phenol has a Lewis acid group (−OH) and its pKa value is 9.95. Table 2 presents the equilibrium data for the extraction of phenol with change in initial TDDA concentration (100 w = 5 to 100 w = 20) in the organic phase, and pH (3 to 11) of the aqueous solution. As seen from Table 2, TDDA concentration 3859
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Table 2. Equilibrium Data of Reactive Extraction of Phenol (100 ppm) Using TDDA at Temperature T = 298 ± 1 K CHA
C̅ HA
100 w
pH
ppm
ppm
KD
%
Z
5
3 5 7 9 11 3 5 7 9 11 3 5 7 9 11
32.24 31.42 31.63 34.20 61.16 23.16 22.62 23.03 28.11 58.99 17.13 16.59 16.99 23.77 56.75
67.76 68.58 68.37 65.79 38.84 76.84 77.38 76.97 71.89 41.01 82.87 83.41 83.00 76.23 43.25
2.102 2.182 2.162 1.924 0.635 3.317 3.421 3.343 2.558 0.695 4.836 5.027 4.883 3.207 0.762
67.76 68.58 68.37 65.79 38.84 76.84 77.38 76.97 71.89 41.01 82.87 83.41 83.00 76.23 43.25
0.0091 0.0092 0.0092 0.0089 0.0052 0.0052 0.0052 0.0052 0.0048 0.0028 0.0028 0.0028 0.0028 0.0026 0.0015
[TDDA]0
10
20
E
Figure 1. Degree of extraction (% E) for the reactive extraction of phenol (100 ppm) with TDDA dissolved in benzene at temperature T = 298 ± 1 K. Symbols: ■, 100 w = 5; ○, 100 w = 10; ∗, 100 w = 20.
the nondissociated part of the phenol present in the aqueous phase) and n molecules of TDDA to form (1, n) complexes in the organic phase, eq 3.20
has one of the strong effects on the equilibrium distribution of phenol. The value of D increases from 2.102 (67.76 %E) to 3.317 (82.87 %E) at pH = 3 as TDDA concentration increases from 100 w = 5 to 100 w = 10 in benzene. Similar kinds of results were also observed at other pH values. Phenol was extracted into the organic phase more effectively at higher TDDA concentrations, which likely results from the extraction equilibrium moving toward the direction of forming an extraction complex. The value of D increases more obviously when TDDA concentration increases from 100 w = 5 to 100 w = 20 (1.58 times) than from 100 w = 5 to 100 w = 10 (2.3 times) at pH = 3. In the extraction system, the reacting and dissolving capacity of the extraction complex increases with an increase in the TDDA concentration as the higher value of TDDA concentration helps the extraction complex dissolve easily in the extraction system. The maximum removal of phenol was observed to be 83.41 % with TDDA (100 w = 20 at pH = 5. The amine extractant, TDDA is a Lewis alkali and can receive a proton. As such it can react with neutral form of phenol to produce the complex that is extracted into the organic phase. The anionic form of phenol would dominate at pH > pKa and therefore it is essential to understand the effect of pH on the extraction mechanism. Since the pH of an aqueous solution of phenol affects the molar fraction of neutral phenol, the distribution coefficient greatly depends on equilibrium pH. The variation of degree of extraction with pH at different TDDA concentration is shown in Figure 1 at 100 ppm phenol concentration and at 298 ± 1 K temperature. The values of D have an increasing trend up to pH = 5 and then decrease. The value of D is relatively constant from pH of 3 to 9 with a maximum occurring at pH from 5 to 7, and after that it sharply decreases. It happens because the anionic form of phenol appears at high pH which reacts little with TDDA, so the D value decreases with an increase in solution pH. The equilibrium of reactive extraction for a polar dilute solution of organic solutes could be described by the mass action law in which the equilibrium phenomena can be modeled by considering the formation of various stoichiometric complexes of phenol with the TDDA. In the reactive, the equilibrium reactions taking place in the system can be written as by a set of equations of one phenol molecule (HA represents
KE
HA + nTDDA ↔ (TDDA)n (HA)
(3)
where n is the solvation number of TDDA. As the phenol− TDDA complex is formed, it is rapidly extracted into the organic phase, and the corresponding equilibrium complexation constant is defined by applying the law of mass action as eq 4: [(HA)·(TDDA)n ]
K=
[HA]·[(TDDA)]n
(4)
The expression for the distribution coefficient, as shown in eq 1, can be represented as, [(HA)·(TDDA)n ] [HA] + [A−]
D=
(5)
The dissociation reaction of phenol at equilibrium in the aqueous phase is shown as Ka
HA ↔ ↔ H+ + A−
(6)
The dissociation constant (Ka) of phenol in water is given by eq 7. Ka =
[H+][A−] [HA]
(7)
From eq 7, the concentration of dissociated part of phenol can be expressed in terms of undissociated phenol concentration ([HA]), pKa, and pH of aqueous solution as [A−] = [HA](1 + 10 pK a − pH)
(8)
Now, substituting the values of [(HA)·(TDDA)n ] and [A−] from eq 4 and eq 8, respectively, in eq 5, eq 9 is obtained.
D=
K ·[TDDA]n (1 + 10 pH − pK a)
(9)
The free extractant concentration, [TDDA]in the organic phase at equilibrium is represented as, [TDDA] = [TDDA]0 − [(HA)(TDDA)n ] 3860
(10)
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Table 3. Values of Equilibrium Parameters for the Extraction of Phenol (100 ppm) using TDDA (100 w = (5, 10, and 20)) at Different Values of pH (± 0.1) and at temperature T = 298 ± 1 K
The value of [TDDA]from eq 10 is substituted in eq 9 which results in eq 11. D=
K ·([TDDA]0 − [(HA)(TDDA)n ])n (1 + 10 pH − pK a)
(11)
pH
Now, for the estimation of equilibrium constant (K) and the number of extractant molecules per phenol molecule (n), the theoretical study based on mass action law is carried out. If it is assumed that the initial concentration of extractant, that is, [TDDA]0 is far higher than that of the phenol-extractant formed ⌊(HA)(TDDA)n ⌋ i.e. [TDDA]0 ≫ ⌊(HA)(TDDA)n ⌋ then eq 11 for the distribution coefficient D can be written as
D=
n
log(K)
3 5 7 9 11
0.9912 1.00736 0.98755 0.7410 1.03469
± ± ± ± ±
0.0277 0.0226 0.0199 0.0206 0.00045
0.60105 0.60191 0.58773 0.36858 0.13133
± ± ± ± ±
0.0331 0.0269 0.0237 0.0245 0.00055
R2
SD
0.997 0.998 0.998 0.996 0.999
0.0141 0.0115 0.0101 0.0104 0.0002
K ·([TDDA]0 )n (1 + 10 pH − pK a)
(12)
This assumption is not valid at higher concentrations of phenol due to an increased concentration of extractant in the complex. Equation 12 can be linearized in the form as shown in eq 13 to find the equilibrium parameters such as n and K. log[D·(1 + 10 pH − pK a)] = log K + n • log[TDDA]0 (13) pH−pKa
The plot of log[D·(1 + 10 )] or (log W) against log[TDDA]0 would provide a straight line with the intercept, log K and slope, n. This graphical representation is used to estimate the values of K and n. The above equation depicts that the distribution coefficient of phenol depends on the free extractant concentration in the organic phase. Figure 2 shows a
Figure 3. Model predicted (eq 12) versus experimental values of distribution coefficient of phenol (100 ppm) with TDDA (100 w = (5, 10, and 20)) dissolved in benzene at temperature T = 298 ± 1 K. Symbols: +, 3 pH; △, 5 pH; ●, 7 pH; ○, 9 pH; ∗,11 pH.
4. CONCLUSION In this study, the reactive extraction of phenol is carried out using TDDA as an aminic extractant dissolved in benzene. The equilibrium study is conducted to investigate the effect of amine composition and pH on the distribution coefficient, D. It is mainly observed that with an increase in the initial TDDA concentration the extraction efficiency increases, and pH of aqueous solution has an important role to play in the extraction process. The highest range of D appears when the pH is between 5 and 7 at all TDDA concentrations. The maximum recovery of phenol (D = (5.027, 83.41) %E) is observed at equilibrium pH of 5 and at highest concentration of TDDA (100 w = 20). The stoichiometric coefficient, n (= 0.60) confirms the formation of the 1:1 and 2:1 type of phenol− TDDA complex in the extract phase. The values of D at equilibrium are also predicted showing a good agreement with the experimental values of D with a maximum error of 2.6%.
Figure 2. Determination of K and n for the reactive extraction of phenol (100 ppm) using TDDA (100 w = (5, 10, and 20)) dissolved in benzene at different pH and at temperature T = 298 ± 1 K. Symbols: +, 3 pH; △, 5 pH; ●, 7 pH; ○, 9 pH; ∗,11 pH; , linear fit lines.
■
plot of log W vs log[TDDA]0 , and the results are presented in Table 3 for different TDDA concentration and different pH. Good results have been obtained with R2 > 0.99 and SD < 0.0141. The highest value of K (1.007) for the phenol−TDDA complexation is obtained at pH = 5. A value of n = 0.60 is estimated which shows 1:1 and 2:1 stoichiometric association of the phenol−TDDA complex in the organic phase. These equilibrium parameters are used to predict the values of D and are shown in Figure 3. It is observed that the experimental values of D show a good agreement with model predicted values with a maximum error of 2.6%.
AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. Notes
The authors declare no competing financial interest.
■
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