Adsorption Removal of Various Nitrophenols in Aqueous Solution by

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Adsorption Removal of Various Nitrophenols in Aqueous Solution by Aminopropyl-Modified Mesoporous MCM-48 Xingxing Gu,*,† Han Kang,† Hui Li,† Xuecheng Liu,† Fan Dong,† Min Fu,† and Jianrong Chen*,‡ †

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Chongqing Key Laboratory of Catalysis and New Environmental Materials, College of Environment and Resources, Chongqing Technology and Business University, Chongqing 400067, China ‡ College of Geography and Environmental Sciences, Zhejiang Normal University, Jinhua, Zhejing 321004, China ABSTRACT: The adsorption of o-nitrophenol, m-nitrophenol, and p-nitrophenol in aqueous solution by aminopropyl-modified MCM-48 (NH2-MCM-48) was studied. Investigations were focused on the factors such as the effect of pH, dosage of sorbent, initial concentrations of nitrophenols, temperature, and adsorption time on the adsorption of nitrophenols. It is very exciting to see that NH2-MCM48 exhibits superior adsorption capacity for these three kinds of nitrophenols. Such remarkable adsorption affinity is attributed to the hydrogen bonding between nitrophenols and the amino groups in NH2-MCM-48. The Freundlich and Langmuir adsorption isotherm models were applied to fit the experimental equilibrium adsorption data, and the corresponding results show that the equilibrium data fit well into the Langmuir adsorption isotherm. Kinetic studies show that the pseudo-second-order kinetic model fit the adsorption experimental data better than the pseudo-first-order kinetic model. According to the calculated thermodynamic parameters, it is noticeable that the adsorption of o-nitrophenol, m-nitrophenol, and p-nitrophenol by NH2MCM-48 adsorbents was spontaneous and exothermic in nature. Additionally, cycle rate experiments demonstrate that NH2MCM-48 is an effective and reusable sorbent for the nitrophenols in aqueous solutions.

1. INTRODUCTION Phenolic compounds are one kind of pollutant that causes an unpleasant taste and odor in drinking water. These compounds in water mainly comes from the effluents discharged from steel mills, oil refineries, petrochemical plants, resin manufacturing, pharmaceutical industries, dye industries, and so on.1−3 The U.S. Environmental Protection Agency (EPA) has identified 1777 National Priorities List (NPL) sites, and nitrophenols are located at 14 of these sites.4,5 The U.S. EPA regulations also call for lowering the phenol content in wastewater to o-nitrophenol > m-nitrophenol at pH 6.5, which owes to the strengths of their own acid−base properties and spatial steric hindrance.41 On the basis of these findings, all subsequent experiments were carried out under the optimum pH conditions for the three nitrophenols. The adsorbent dose is an important parameter in adsorption studies. It determines the adsorption capacity of the adsorbent at a given initial concentration of the target solution. The effect of adsorbent dose on the removal percentage of the nitrophenols was shown in Figure 6. It was clearly observed that the removal percentage increased rapidly with the increase

Figure 2. XRD patterns of (a) MCM-48 and (b) NH2-MCM-48.

Figure 2a, the four diffraction peaks at around 2θ = 2.63, 3.03, 4.80, and 5.02° are indexed to the Ia3d cubic structure of MCM-48, corresponding to lattice planes of (211), (220), (420), and (332), respectively,.33,38 In Figure 2b, the diffraction peaks for lattice planes of (220), (420), and (332) disappeared, but the diffraction peak for lattice plane (211) remained, demonstrating that NH2-MCM-48 maintains a parallel channel-like porous structure like that of MCM-48. The disappearance of diffraction peaks is mainly attributed to part of the amino group being successfully incorporated into the mesoporous frame.32 The FTIR spectra of the MCM-48 and NH2-MCM-48 materials are presented in Figure 3. A broad absorption band at

Figure 3. FTIR spectra of (a) MCM-48 and (b) NH2-MCM-48.

3430 cm−1 is usually assigned to Si(OH), Si(OH)2 or −Si(OH)3 groups of the pore surface.32,33 The peak at around 1637 cm−1 is mainly from the bending vibration of adsorbed water.32,39 The band at 1070 cm−1 is attributed to the Si−O− Si asymmetric stretching vibration, while the band at around 790 cm−1 is attributed to the Si−O−Si symmetric stretching vibration.32 The peak at 450 cm−1 can be ascribed to the bending vibration of Si−O−Si.32,39 The peaks at 2848 and 2923 cm−1 in Figure 3b are attributed to C−H bending and stretching vibrations.32,39 The band at 1560 cm−1 in Figure 3b is attributed to the N−H bending vibration.32 C

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Figure 4. (a) Nitrogen adsorption/desorption isotherms of MCM-48 and NH2-MCM-48. (b) TG thermograms of MCM-48 and NH2-MCM-48.

in adsorbent dose at the beginning. After the adsorbent dose approached the critical dose (at around 25 mg), the removal percentage reached an almost constant value. The adsorption rate is one of the most important factors in the adsorption process. As seen from Figure 7a, the contact time curve shows that nitrophenol removal was very quick in the first 20 min and adsorption equilibrium reached around 45 min with an initial concentration of 25 mg/L. The fast adsorption occurred because the sorption occurred at the surface rather than in the mesopores. The tendencies of adsorption capacities and rates were also investigated using the pseudo-first-order and pseudo-secondorder kinetic models. The pseudo-first-order kinetic model is expressed as the following equation,21,22,25,33

Table 1. Structural Properties of MCM-48 and NH2-MCM48 samples

BET surface area (m2 g−1)

total pore volume (cm3 g−1)

average pore diameter (nm)

MCM-48 NH2-MCM-48

1072 297

1.08 0.08

2.71 1.86

ln(qe − qt ) = ln qe − k1t

(3)

−1

where k1 (min ) is the pseudo-first-order rate constant and qe (mg/g) and qt (mg/g) are the amounts of nitrophenols adsorbed per unit mass of adsorbent at equilibrium and time t, respectively. The pseudo-second-order kinetic model can be described in the following form,21,22,25,33 t 1 1 = + t 2 qt qe k 2qe

Figure 5. Effect of solution pH on the removal of nitrophenols by NH2-MCM-48 (concentration of nitrophenol, 25 mg/L; temperature, 20 ± 1 °C; contact time, 45 min).

(4)

where k2 is the rate constant of pseudo-second-order adsorption (g/(mg·min)) and qe (mg/g) and qt (mg/g) are the amounts of nitrophenols adsorbed per unit mass of the adsorbent at equilibrium and time t, respectively. Figure 7b−d shows that the pseudo-second-order model curves were linear at different initial concentrations when the temperature was set at 293.15 K. The parameters of the pseudo-first-order and pseudosecond-order models were summarized in Table 2. They reveal that the pseudo-second-order model better described the adsorption process due to the higher R2 (>0.999). In addition, good agreement with this kinetic adsorption model was confirmed by the fact that the experimental data, qe,exp, are closer to the calculated values, qe,cal. The values of the rate constants were found to decrease at all of the studied concentrations, likely implying that the adsorption of nitrophenols on NH2-MCM-48 obeys a physisorption process.22 The rate-controlling step may involve hydrogen bonding and electron donor−acceptor interactions.22 The adsorption isotherm describes the relationship between the nitrophenol amount (qe) adsorbed by the unit mass of adsorbent and the nitrophenol concentration (Ce) in the solution at a constant temperature. Figure 8 shows the

Figure 6. Effect of adsorbent dose for the removal of nitrophenols (concentration of nitrophenol, 25 mg/L; temperature, 20 ± 1 °C; contact time, 45 min).

D

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Figure 7. (a) Effect of contact time for the removal of nitrophenols. Pseudo-second-order kinetic adsorption of (b) o-nitrophenols, (c) mnitrophenols, and (d) p-nitrophenols on NH2-MCM-48. (T = 293.15 K; adsorbent amount, 25 mg; and oscillation rate, 220 rpm/min).

Table 2. Kinetic Adsorption Parameters of Nitrophenols under Different Initial Concentrations pseudo-first-order kinetics −1

pseudo-second-order kinetics

adsorbates

C0 (mg/L)

qe,exp (mg/g)

k1 (min )

qe,cal (mg/g)

R

k2 (min g/mg)

qe,cal (mg/g)

R2

o-nitrophenol

25 50 80 25 50 80 25 50 80

14.85 24.75 35.49 15.26 26.43 38.49 17.09 30.14 43.20

0.0366 0.0954 0.0438 0.1497 0.0766 0.0596 0.0583 0.0353 0.0261

1.64 8.47 4.07 5.09 6.22 7.99 2.35 3.42 6.45

0.9793 0.9499 0.9104 0.9672 0.9767 0.9352 0.9882 0.9828 0.9841

0.0041 0.0014 0.0008 0.0040 0.0014 0.0007 0.0027 0.0011 0.0005

15.24 26.43 36.55 16.12 27.08 39.31 19.26 30.44 43.49

0.9999 0.9998 0.9997 0.9998 0.9996 0.9999 0.9998 0.9999 0.9996

m-nitrophenol

p-nitrophenol

where C0 is the highest initial concentration of adsorbate (mol/L) and b (L/mol) is the Langmuir adsorption constant. Parameter RL indicates the nature of the shape of the isotherm accordingly: RL > 1, unfavorable adsorption 0 < RL < 1, favorable adsorption RL = 0, irreversible adsorption RL = 1, linear adsorption As presented in Table 3, all nitrophenol separation factors are between 0 and 1, implying that the adsorption of nitrophenols on NH2-MCM-48 is favorable.21,29,33 The Freundlich isotherm is an empirical equation assuming that the adsorption process takes place on heterogeneous surfaces and the adsorption capacity is related to the concentration of nitrophenol at equilibrium.21,33 A linear form of the Freundlich equation is generally expressed as follows

adsorption isotherm curves for the three nitrophenols. To determine the parameters associated with o-nitrophenol, pnitrophenol, and m-nitrophenol adsorption, the experimental data were analyzed using the Langmuir and Freundlich adsorption isotherm models, respectively. The Langmuir isotherm assumes monolayer adsorption on a surface with a finite number of identical sites. The linear form of the Langmuir model is given by the following equation21,33 Ce 1 1 Ce + = qe qm qmb

(5)

where qe and qm are the equilibrium adsorption amount and the maximum monolayer adsorption capacity (mg/g), respectively, Ce is the equilibrium concentration of nitrophenol (mg/L), and b is the Langmuir adsorption constant (L/mg). The Langmuir constants were calculated and are presented in Table 3. The essential characteristics of the Langmuir isotherm can be expressed in terms of a dimensionless constant separation factor RL that is given by eq 621,29,33 1 RL = 1 + bC0

2

ln qe =

1 ln Ce + ln KF n

(7)

where KF (mg/g (L/mg)1/n) is roughly an indicator of the adsorption capacity and 1/n is the adsorption intensity. The values of KF, n, and the linear regression correlation (R2) for

(6) E

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Figure 8. Adsorption isotherms of (a) o-nitrophenol, (b) m-nitrophenol, and (c) p-nitrophenol on NH2-MCM-48 (adsorbent, 25 mg; contact time, 45 min; oscillation rate, 220 rpm/min).

Table 3. Langmuir Isotherm Parameters for the Removal of Nitrophenols at Different Temperatures

Table 4. Freundlich Isothem Parameters for the Removal of Nitrophenols at Different Temperatures

temperature (K)

temperature (K)

targets

parameters

293.15

303.15

313.15

targets

parameters

293.15

303.15

313.15

o-nitrophenol

qm (mg/g) b (L/mg) R2 RL qm (mg/g) b (L/mg) R2 RL qm (mg/g) b (L/mg) R2 RL

72.99 0.043 0.984 0.48 102.04 0.024 0.994 0.63 107.53 0.031 0.992 0.56

70.92 0.035 0.976 0.53 95.23 0.021 0.993 0.65 97.24 0.030 0.992 0.57

64.94 0.034 0.972 0.54 92.59 0.017 0.995 0.70 93.91 0.028 0.996 0.58

o-nitrophenol

n KF (mg/g (L/mg)1/n) R2 n KF (mg/g (L/mg)1/n) R2 n KF (mg/g (L/mg)1/n) R2

2.78 10.77 0.951 1.94 6.54 0.976 2.06 8.50 0.975

2.72 9.54 0.953 1.91 5.61 0.974 2.20 8.53 0.981

2.84 9.27 0.941 1.75 4.05 0.970 2.07 6.99 0.969

m-nitrophenol

p-nitrophenol

m-nitrophenol

p-nitrophenol

To investigate thermodynamic parameters such as the adsorption equilibrium constant (KL), Gibbs energy (ΔG0), enthalpy change (ΔH0), and entropy change (ΔS0), the adsorption of three nitrophenols on NH2-MCM-48 was measured at 293.15, 303.15, and 313.15 K, respectively. The distribution coefficient (KL), Gibbs energy (ΔG0), enthalpy change (ΔH0), and entropy change (ΔS0) are calculated using the following equations:7,33 q KL = e Ce (8)

the Freundlich equation are given in Table 4. It can be observed that all of the n values in Table 4 are greater than 1, once again indicating the favorable adsorption of nitrophenols.21,33 In addtion, on the basis of the linear correlation coefficient R2 presented in Tables 3 and 4, it reveals that the Langmuir adsorption isotherm model can better fit the adsorption data in this study. The monolayer adsorption capacities qm for different types of adsorbents used in the removal of nitrophenols are compared in Table 5. As shown in Table 5, the maximum adsortion capacities of nitrophenols on NH2-MCM-48 are higher than those of many other reported adsorbents, and the equilibrium time is very short, suggestting that aminopropylmodified MCM-48 is an effective adsorbent for removing monosubstituted nitrophenols.

ΔG 0 = −RT ln KL

(9)

ΔS0 ΔH0 − (10) R RT The relationship between ln KL and T is given in Figure 9, and the estimated adsorption thermodynamic parameters are given in Table 6. ln KL =

F

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Table 5. Comparison of the Maxium Adsorption Capacity of Nitro-Substituted Phenols on Different Adsorbents adsorbates

adsorbents

capacity (mg/g)

o-nitrophenol

NH2-MCM-48 NH2-MCM-48 flay ash organically modified diatomaceous earth dye-affinity microbeads hyacinth-activated carbon cross-linked starch polymers NH2-MCM-48 NH2-MCM-48 flay ash organically modified diatomaceous earth clinoptilolite NH2-MCM-48 NH2-MCM-48 flay ash organically modified diatomaceous earth dye-affinity microbeads amino-MIL-53(Al) samla coal rice husk rice husk char petroleum coke coke breeze graphene NiAl-layered double hydroxide cross-linked starch polymers bagasse fly ash pyrolyzed oil shale ZnCl2-pyrolyzed oil shale KOH-pyrolyzed oil shale β-cyclodextrin-grafted on silica gel amino silane-modified palm oil fuel ash dimethyloctylamine-modified MCM-41 dodecylamine-modified MCM-41 hexadecylamine-modified MCM-41 dimethyloctylamine-modified MCM-48 dodecylamine-modified MCM-48 hexadecylamine-modified MCM-48

72.99 70.92 6.44 6.035 15.50 47.62 6.226 102.04 95.23 8.06 8.139 60 107.53 97.24 7.80 20.486 15.65 297.85 51.54 15.31 39.21 11.061 4.64 15.50 77.10 8.532 8.3 4.895 6.026 0.895 41.5 1000 201 222 247 189 210 241

m-nitrophenol

p-nitrophenol

equilibrium time (min) 45 45 150 ∼20 180 60 45 45 150 180 45 45 150 ∼20 ∼250 ∼1800 ∼1800 ∼1800 ∼1800 ∼1800 5 100 60 1440 1440 1440 1440 ∼0.1 180 ∼350 ∼350 ∼350 ∼370 ∼370 ∼370

temperature (K)

references

293.15 303.15 303 298.15 293.15 301.15 303 293.15 303.15 303 298.15 298.15 293.15 303.15 303 298.15 293.15 298.15 room temperature room temperature room temperature room temperature room temperature 298 303 303 303.15 298.15 298.15 298.15 303 303 room temperature room temperature room temperature room temperature room temperature room temperature

this this 4 5 6 21 42 this this 4 5 16 this this 4 5 6 15 17 17 17 17 17 26 29 42 43 44 44 44 45 46 47 47 47 47 47 47

work work

work work

work work

As presented in Table 6, the adsorption is spontaneous with the negative value of ΔG0.7,33 The negative value of ΔG0 of all three nitrophenols indicates the spontaneous nature of the adsorption process, while negative ΔH0 indicates that the adsorption process is exothermic in nature,33 which is consistent with the case in which the adsorption capacities of nitrophenols decreased with the increase in temperature. Reusability is a key factor for an effective absorbent. Adsorbents with excellent reusability can reduce the adsorbent cost greatly, which was very important for industrial applications. In this study, the solvent elution was adopted and the nitrophenol-loaded NH2-MCM-48 was regenerated with a 0.1 mol/L HCl solution. As shown in Figure 10, it can be found, under three cycles of desorption−adsorption, that asprepared NH2-MCM-48 maintains a high adsorption capacity for the nitrophenols, and the recycle rate of NH2-MCM-48 could still reach as high as around 80% for all three kinds of nitrophenols, suggesting good reusability of NH2-MCM-48.

Figure 9. Plot of ln KL vs 1/T for the adsorption of nitrophenols on NH2-MCM-48.

G

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Table 6. Thermodynamic Parameters for the Adsorption of Nitrophenols on NH2-MCM-48 ΔG0 (kJ mol−1) adsorbate

293.15 K

303.15 K

313.15 K

ΔS0 (J mol−1 K−1)

ΔH0 (kJ mol−1)

o-nitrophenol m-nitrophenol p-nitrophenol

−2.71 −1.48 −2.45

−2.44 −1.06 −2.14

−2.28 −0.60 −1.90

−21.94 −43.74 −27.54

−9.13 −14.30 −10.51

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ACKNOWLEDGMENTS This work was supported by the National Natural Science Foundation of China (nos. 51478070 and 21777011), the Youth Project of Science and Technology Research Program of Chongqing Education Commission, and the Start-up Foundation of High-Level Talents in Chongqing Technology and Business University (no. 1856008).

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(1) Á lvarez-Torrellas, S.; Martin-Martinez, M.; Gomes, H. T.; Ovejero, G.; García, J. Enhancement of p-Nitrophenol Adsorption Capacity Through N2-Thermal-Based Treatment of Activated Carbons. Appl. Surf. Sci. 2017, 414, 424−434. (2) Ahmaruzzaman, M. Adsorption of Phenolic Compounds on Low-Cost Adsorbents: A Review. Adv. Colloid Interface Sci. 2008, 143, 48−67. (3) Lin, S. H.; Juang, R. S. Adsorption of Phenol and Its Derivatives from Water Using Synthetic Resins and Low-Cost Natural Adsorbents: A Review. J. Environ. Manage. 2009, 90, 1336−1349. (4) Singh, B. K.; Nayak, P. S. Sorption Equilibrium Studies of Toxic Nitro-substituted Phenols on Fly Ash. Adsorpt. Sci. Technol. 2004, 22, 295−309. (5) Al Bakain, R. Z.; Abu-Zurayk, R. A.; Hamadneh, I.; Khalili, F. I.; Al-Dujaili, A. H. A Study on Removal Characteristics of o-, m-, and pNitrophenol from Aqueous Solutions by Organically Modified Diatomaceous Earth. Desalin. Water Treat. 2015, 56, 826−838. (6) Denizli, A.; Ö kan, G.; Uçar, M. Dye-Affinity Microbeads for Removal of Phenols and Nitrophenols from Aquatic Systems. J. Appl. Polym. Sci. 2002, 83, 2411−2418. (7) Chen, J.; Sun, X.; Lin, L.; Dong, X.; He, Y. Adsorption Removal of o-Nitrophenol and p -Nitrophenol from Wastewater by Metal− Organic Framework Cr-BDC. Chin. J. Chem. Eng. 2017, 25, 775−781. (8) Liu, B.; Yang, F.; Zou, Y.; Peng, Y. Adsorption of Phenol and pNitrophenol from Aqueous Solutions on Metal−Organic Frameworks: Effect of Hydrogen Bonding. J. Chem. Eng. Data 2014, 59, 1476−1482. (9) Dinesh, B.; Saraswathi, R. Electrochemical Synthesis of Nanostructured Copper-Curcumin Complex and Its Electrocatalytic Application Towards Reduction of 4-Nitrophenol. Sens. Actuators, B 2017, 253, 502−512. (10) Verma, S.; Dutta, R. K. Enhanced ROS Generation by ZnOAmmonia Modified Graphene Oxide Nanocomposites for Photocatalytic Degradation of Trypan Blue Dye and 4-Nitrophenol. J. Environ. Chem. Eng. 2017, 5, 4776−4787. (11) Yuan, S.; Tian, M.; Cui, Y.; Lin, L.; Lu, X. Treatment of Nitrophenols by Cathode Reduction and Electro-Fenton Methods. J. Hazard. Mater. 2006, 137, 573−580. (12) Bo, L. L.; Zhang, Y. B.; Quan, X.; Zhao, B. Microwave Assisted Catalytic Oxidation of p-Nitrophenol in Aqueous Solution Using Carbon-Supported Copper Catalyst. J. Hazard. Mater. 2008, 153, 1201−1206. (13) Hidalgo, A. M.; León, G.; Gómez, M.; Murcia, M. D.; Gómez, E.; Giner, C. Behaviour of RO90 Membrane on the Removal of 4Nitrophenol and 4-Nitroaniline by Low Pressure Reverse Osmosis. J. Water Process Eng. 2015, 7, 169−175. (14) Kristanti, R. A.; Kanbe, M.; Toyama, T.; Tanaka, Y.; Tang, Y.; Wu, X.; Mori, K. Accelerated Biodegradation of Nitrophenols in the Rhizosphere of Spirodela Polyrrhiza. J. Environ. Sci. 2012, 24, 800− 807.

Figure 10. Adsorption−desorption cycles. Initial concentration of onitrophenol, m-nitrophenol, and p-nitrophenol, 50 mg/L; adsorbent dosage, 25 mg; contact time, 45 min; and oscillation rate, 220 rpm/ min.

4. CONCLUSIONS NH2-MCM-48 was successfully synthesized on the basis of a co-condensation method through grafting amino groups onto the MCM-48 skeleton. It was used as an effective adsorbent in removing monosubstituted nitrophenols. The studies have shown that the aminopropyl-modified MCM-48 had a high adsorption capacity for these three kinds of nitrophenols. It was found that the adsorption capacities of the nitrophenols decreased with the temperature increase. The removal efficiency for the nitrophenols increased first and then decreased with the solution pH increasing, and the maximum amount of adsorption capacity appeared under neutral conditions. In addition, the experimental results showed that adsorption isotherms and kinetics data were better fit to the Langmuir isotherm model and the pseudo-second-order kinetic model, respectively. The thermodynamic investigations demonstrated that the adsorption process was exothermic and spontaneous in nature.

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REFERENCES

AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected]. *E-mail: [email protected]. ORCID

Xingxing Gu: 0000-0002-5145-7751 Fan Dong: 0000-0003-2890-9964 Notes

The authors declare no competing financial interest. H

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DOI: 10.1021/acs.jced.8b00477 J. Chem. Eng. Data XXXX, XXX, XXX−XXX