New Calix[4]arene Appended Amberlite XAD-4 Resin with Versatile

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New Calix[4]arene Appended Amberlite XAD‑4 Resin with Versatile Perchlorate Removal Efficiency Shahabuddin Memon,* Asif Ali Bhatti, and Najma Memon National Center of Excellence in Analytical Chemistry, University of Sindh, Jamshoro 76080, Pakistan ABSTRACT: Perchlorate removal from an aqueous environment was carried out by newly synthesized 25,27-bis-(N,N-dimethyl-2aminoethyl)carbonylmethoxy-26,28-dihydroxycalix[4]arene appended Amberlite XAD-4 resin (Resin-5). Different parameters such as pH, dosage, concentration, interference, equilibrium isotherms, kinetics, and thermodynamics were explored. Experimental data were treated using equilibrium models such as Freundlich, Langmuir, and the Dubinin−Radushkevich (D−R) model, with determination of each characteristic parameter of isotherm. The adsorption mechanism was investigated by Reichenberg (R−B) and Morris-Webster equations, and it is concluded that the adsorption process is endothermic and spontaneous in nature at higher temperature. The kinetic adsorption experiments show that the adsorption process follows pseudo-second-order kinetics. The results show that newly synthesized resin has capability to efficiently remove perchlorate from aqueous media.

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INTRODUCTION Perchlorate salts, due to their much lower costs, have been frequently used in solid propellants of rockets/missiles, air bags, explosives, and batteries.1−4 However, nowadays perchlorate is attracting increasing attention as an extremely persistent inorganic contaminant in drinking, ground, and surface water.5−7 Lasting acquaintance to perceptible perchlorate can cause substantial health hazards such as declined production of thyroid hormones to humans that results in retardation of physical and mental growths. It is also recognized as an endocrine-disruptor chemical that leads to cancer.8−10 An official reference dose of 0.0000291 mg·kg−1h−1 for perchlorate has been set by Environment Protection Agency (EPA) corresponding to a drinking water equivalent level of 24.5 μg· L−1 in 2005.11 Thus, perchlorate removal has always been a big task for the traditional drinking water treatment process because of the high solubility, kinetically inert nature, and difficult removal of the material. Several developed technologies have been used for perchlorate removal comprising solid phase extraction, biological treatment, ion exchange chemical/ catalytic reduction, and membrane filtration.12−16 Of these technologies, solid phase extraction by reason of its inexpensive, high treatment efficiency, easy design, and operation has attained considerable attention. Many kinds of synthetic and natural adsorbent materials have been used recently for perchlorate removal from aqueous media, for example granular activated carbon amended with cationic surfactants,17 magnetic permanently confined micelle arrays (Mag-PCMAs),18 wheat straw,19 cross-linked quaternary chitosan,20 and raw and oxidized carbon nanotubes,21 but the adsorption capability of these was not so operative. Therefore, there is a dire call for new materials and methods for © XXXX American Chemical Society

perchlorate pollution treatment. In this regard, the supramolecular chemistry has provided a much improved solution in the form of macrocyclic host compounds such as calixarenes.22−25 The calixarenes have been proven as an excellent class of building blocks for the synthesis of ionophores with almost unlimited derivatization possibilities.26 To improve the ionophoric ability of calixarenes toward the target species, various groups are incorporated at their lower/upper rim and then appended within a polymeric backbone to increase their extraction efficiency, thermal stability, and reusability.27 The aim of the current study was focused on the synthesis and evaluation of perchlorate adsorption efficiency of new material, that is, 25,27-bis-(N,N-dimethyl-2-aminoethyl)carbonylmethoxy-26,28-dihydroxycalix[4]arene appended Amberlite XAD-4 resin (Resin-5). Besides this, the impact of amount and the effect of solution pH and interfering ions on the adsorption capacity of the resin-5 has also been studied.

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EXPERIMENTAL SECTION Analytical grade reagents procured from Merck (Darmstadt, Germany) were used for the preparation of all kinds of the solutions. A stock standard solution 1 mol·kg−1 was prepared using KClO4. Calibration standards were prepared by diluting stock solution. The pH of the solution was adjusted by mixing an appropriate amount of 0.1 mol·kg−1 (HCl/KOH). A pH meter (781-pH/Ion Meter, Metrohm, Herisau Switzerland) with glass electrode and internal reference electrode was used Received: June 11, 2013 Accepted: September 8, 2013

A

dx.doi.org/10.1021/je400554q | J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

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Scheme 1. Schematic Route for Synthesis of Calix[4]arene Derivative (d)

Scheme 2. Schematic Rout for Synthesis of Calix[4]arene Based Modified Amberlite XAD-4 Resin (Resin-5)

HNO3, and washed with deionized water before use. All aqueous solutions were prepared with deionized water. Synthesis. The compounds a, b, c and d were synthesized by previously reported methods.28−30 New resin-5 was synthesized according to a developed method.31 The FT-IR spectroscopy was used to confirm the immobilization of the resin.

for pH measurements. Janke & Kunikel automatic shaker model KS 501 D, Singapore, was used at ambient temperature (25 ± 2) °C. Perchlorate analysis was done on 93 Series Perchlorate Sensing Module ThermoOrian. Amberlite XAD-4 (surface area of 825 m2·g, pore diameter 14.4 nm, and bead size 20.50 mesh) was obtained from Fluka, Germany. All glassware were carefully washed and soaked overnight in 3 mol·kg−1 of B



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Figure 1. TGA curve of resin-5.

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Characterization. The synthesized resin-5 was characterized through TGA/DTA and FT-IR spectroscopy. Calix[4]arene derivative (d) was appended on Amberlite XAD-4 through diazotization and confirmed by FTIR spectra that shows additional bands at 1704 cm−1, 1504 cm−1, and 1443 cm−1, which can be attributed to the CO, C−O, and NN stretching, respectively. The stability of a resin can be justified by its temperature dependence, and it was examined by the TGA analyses. Two key steps on thermal degradation curves are observed as shown in Figure 1. The first step ranging from 30 °C to 150 °C is allotted to the loss of physically adsorbed water. Another step ranging from 250 °C to 450 °C is recognized due to the combustion of resin-5 that shows wide room for temperature working conditions. Adsorption Procedure. Perchlorate adsorption was carried out using a batch equilibration technique at ambient temperature. A 10 mL sample solution containing perchlorate (1·10−4 mol·kg−1) was taken in a 25 mL Erlenmeyer flask, and resin-5 (0.1 g) was added. The mixture was equilibrated for 60 min. After filtration, the concentration of perchlorate was examined by a perchlorate selective electrode using a perchlorate analysis method. As a minimum 10 concentration points including the blank and calibration, were run in duplicate. The percent adsorption of perchlorate was calculated as follows: % Adsorption =

C i − Cf 100 Ci

RESULTS AND DISCUSSION Effect of Adsorbent Dosage and Concentration. Adsorbent dosage is a significant factor because this establishes

(1) Figure 2. (a) Effect of adsorbent dosage (10 mL of perchlorate with concentration 1·10−4 mol·kg−1, 60 min contact time). (b) Effect of concentration on adsorption capacity (0.1 g adsorbent, 10 mL of perchlorate with, 60 min contact time).

where Ci (mol·kg−1) and Cf (mol·kg−1) are the first and last concentrations of solution before and after the adsorption of the perchlorate, respectively. The adsorption capacity was calculated as follows: qe =

(C i − Ce)V m

the capability of an adsorbent for a given initial concentration of the adsorbate at the effective environments.32 The effect of the amount of adsorbent on the extraction of perchlorate is shown in Figure 2a. It was perceived that as the amount of resin-5 increases, the adsorption of perchlorate (1·10−4 mol· kg−1) increases due to more surface area available for adsorption. Maximum adsorption (94.42%) was achieved at

(2)

where qe mmol·g−1 is the adsorption capacity, Ci (mol·kg−1) and Ce (mol·kg−1) are the initial and equilibrium concentration, respectively, V is the volume (mL) of solution, and m the mass (g) of adsorbent. C



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Figure 6. D−R isotherm (concn 1.90·10−5 mol·kg−1 to 1.0·10−4 mol· kg−1, 0.1 g adsorbent per 10 mL of adsorbate with 60 min shaking time at 25 °C).

Figure 3. Effect of pH on the percent adsorption (10 mL of perchlorate with concentration of 1·10−4 mol·kg−1, 60 min contact time). Schematic representation shows the proposed adsorption mechanism at different pH values.

pH Effect on Perchlorate Adsorption. The effect of pH (2.5−7.5) on perchlorate adsorption by resin-5 is shown in Figure 3. The pH trend can be justified by the proposed mechanism (Figure 3) for interaction of perchlorate with resin-5. At lower pH (2.5−3.5) there is little or no interactions due to Cl− inhibition that competes with negatively charged perchlorate as shown in model-I. In model-II, the presence of protonated nitrogen at moderate pH increases adsorption of perchlorate, and as the pH goes up to neutral level, adsorption decreased due to a decrease in protonated binding sites. The increased adsorption of perchlorate at moderate pH could also be caused by the endorsed electrostatic interfaces between the negatively charged perchlorate and the positively charged ammonium ions on resin-5. Adsorption Isotherms. The adsorption isotherms can be applied to predict the adsorbate behavior that has not been experimentally investigated. Langmuir, D−R, and Freundlich models were fitted to experimental data to examine the quantity of the perchlorate adsorbed per unit amount of the adsorbent. The initial concentration of adsorbate is in the range of 1.90· 10−5 mol·kg−1 to 1.0·10−4 mol·kg−1, with 0.1 g adsorbent per 10 mL of adsorbate with 60 min shaking time at 298 K. These nonlinear isotherm models can be recast as linear equations.33−35 The Langmuir isotherm (eq 3) is based on the assumption of monolayer surface coverage, equivalent adsorption sites, and independent adsorption sites.

Figure 4. Langmuir isotherm (concn 1.90·10−5 mol·kg−1 to 1.0·10−4 mol·kg−1, 0.1 g adsorbent per 10 mL of adsorbate with 60 min shaking time at 25 °C).

Figure 5. Freundlich isotherm (concn 1.90·10−5 mol·kg−1 to 1.0·10−4 mol·kg−1, 0.1 g adsorbent per 10 mL of adsorbate with 60 min shaking time at 25 °C).

Ce C 1 = + e Cads Qb Q

(3) −1

From the linear plot of Ce/Cads versus Ce (mol·kg ), values of Q (mol g−1) and b (kg mol−1) were calculated (Figure 4). The separation factor RL = 1+ (1/bCi) is an essential characteristic of the Langmuir isotherm and describes the type of isotherm. The RL values found between 0.97 and 0.82 show favorability (0 < RL < 1) of the isotherm.36 The Freundlich isotherm (eq 4) is useful to identify adsorption phenomena with the heterogeneous sorbent

0.1 g of the resin-5 and adsorption remained almost constant up to 0.15 g. There is no significant change in percent adsorption after 0.1 g at that concentration. Keeping in view above results further study was processed at 0.1 g of adsorbent. Keeping the amount of adsorbent constant and effect of adsorbate with different concentration has been performed (Figure 2b). The maximum adsorption was found at 11.35 mmol·g−1.

Table 1. Langmuir, Freundlich and D−R Isotherm Parameters for Adsorption of Perchlorate on to Resin-5a Q/mmol·g−1

b·104 /kg·mol−1

R2

A/kg mol−1

1/n

R2

Xm /mmol·g−1

E/kJ·mol−1

R2

138.64

1258.74

0.994

0.654

0.425

0.960

0.761

12.90

0.977

a

Notation: Q, Langmuir isotherm monolayer adsorption saturation capacity; b, enthalpy of sorption; A, Freundlich isotherm multilayer adsorption capacity; Xm, D−R isotherm maximum adsorption capacity; E, mean free energy; R2, regression coefficient. D



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Table 2. Pseudo-first-order and Pseudo-second-order Kinetic Parameters for Adsorption of Perchlorate on Resin-5a T

K1/min−1

qe/mmol·g−1

R2

K2/g·mol−1·min−1

qe/mmol·g−1

R2

293 303 313

0.0741 0.0968 0.0994

0.0514 0.0626 0.0614

0.934 0.978 0.979

162.08 47.529 43.971

0.0494 0.0838 0.0879

0.990 0.999 0.994

a

Notation: k1 and k2 are the adsorption rate constants; qe, amount of adsorbent adsorbed at equilibrium, T is the working temperature; R2 is the regression coefficient.

Figure 7. Reichenberg (R−B) plot at different temperatures for the sorption of perchlorate on Resin-5.

Figure 10. Arrhenius plot for the adsorption of perchlorate on resin-5.

Figure 11. Effect of temperature on adsorption of perchlorate ion on resin-5.

Figure 8. Morris−Weber plot at different temperature for the adsorption of perchlorate ion on resin-5.

Table 3. Thermodynamic Parameters for Adsorption of Perchlorate on Resin-5a ΔG/kJ·mol−1 ΔH/kJ·mol 0.0206

−1

−1

−1

ΔS/kJ·mol ·K 0.0871

293 K

303 K

313 K

−5.02 ln Kc =2.06

−5.35 ln Kc= 2.13

−6.78 ln Kc= 2.61

a Notation: ΔH, change in enthalpy; ΔS, change in entropy; and ΔG, change in free energy.

Figure 9. Adsorption of perchlorate on to resin-5 as a function of time at different temperatures.

media. Assumption of this isotherm suggests that the adsorption sites are distributed exponentially pertaining to the heat of adsorption.37 1 ln Cads = ln A + ln Ce (4) n

Figure 12. Effect of coexisting anions on perchlorate adsorption efficiency of resin-5.

where A and 1/n are the Freundlich constants, obtained from the slope and intercept of the plot of ln Cads versus ln Ce, indicating the adsorption capacity and adsorption intensity, respectively (Figure 5). The value of 1/n < 1 (Table 1),

indicating that perchlorate is favorably adsorbed by resin-5 at low concentration. A greater value of A also suggests that there is greater perchlorate uptake by the newly synthesized resin. E



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Table 4. Comparison of Resin-5 with Other Synthesized Materiala

oxidized carbon nanotubes (CNTs) GAC-CTAC quaternary amine modified reed MIEX resin Fe-GAC calcined Zn/Al layered double hydroxides resin-5 a

E=

pH

qe/mmol· g−1

4.0 2.5 10.5 7.0 3.0 -

0.068 0.36 3.25 0.96 0.16 5.49

21 43 44 4 45 46

1.5

11.35

present study

(6)

The values of E determine the adsorption mechanism, whether it is physical adsorption (0−8) kJ·mol−1 or chemical ion exchange (8−16) kJ·mol−1. Herein, the extent of E is between 8 kJ·mol−1 and 16 kJ·mol−1, which reveals that the adsorption process follows chemical ion exchange.39 Table 1 shows the value of R2 is greater in Langmuir than in Freundlich and D−R, specifying that the adsorption process favors the Langmuir isotherm; that is, the adsorbate/ion is chemically adsorbed. Adsorption Kinetics. The batch experiment plays a key role in the design and evolution for the presentation of adsorption kinetics, and can be determined by following these main steps:40 internal diffusion (diffusion of molecules inside the pores), external diffusion (diffusion of molecules from the bulk phase toward the interface space), surface diffusion (diffusion of molecules in the surface phase), and adsorption/ desorption elementary processes. To evaluate the adsorption efficiency of sorbents, the experimental data are subjected to different kinetics equations such as Lagergren, pseudo-secondorder rate expression, and Morris−Weber and Reichenberg.41,42 Lagergren/pseudo-first-order and pseudo-second-order kinetic eqs 7 and 8 are as follows:

ref

Notation: qe, adsorption capacity.

The Dubinin−Radushkevich, (D−R) isotherm (eq 5, Figure 6) is broader than the Langmuir isotherm as its deviances are not based on ideal assumptions such as equipotential of adsorption positions, lack of steric hindrances between adsorbed and entering units, or surface homogeneity on the microscopic level.38 ln Cads = ln X m − βε 2

1 −2β

(5) −1

where ε = RT ln(1 + 1/Ce), Cads (mol·g ) is the amount of adsorbate adsorbed per unit mass of the adsorbent and Ce (mol kg−1) is the amount of perchlorate in liquid phase at equilibrium. Xm and β are D−R isotherm constants and can be used to get information regarding mean free energy E (kJ· mol−1) of adsorption.

ln(qe − qt) = ln qe − k1t

(7)

Scheme 3. Regeneration Profile of Resin-5 with 0.3 mol·kg−1 HCl

F


Journal of Chemical & Engineering Data ⎛ ⎞ t t ⎟ ⎛⎜ 1 ⎞⎟ = ⎜⎜ +⎜ ⎟ 2⎟ qt ⎝ k 2qe ⎠ ⎝ qe ⎠

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mol−1·K−1) is the gas law constant, and T is the absolute temperature. The value of Ea (55.4 kJ·mol−1) calculated from the plot of ln k1 versus T−1 (Figure 10). The value of the activation energy is in the range of (40−800) kJ·mol−1 which suggests that the adsorption is chemical in nature. The van’t Hoff equation (eq 12) was used for numerical values of ΔH (kJ·mol−1), ΔS (kJ·mol·K−1), and ΔG (kJ·mol−1) by plotting ln kc versus T−1 (Figure 11).

(8)

−1

where qt (mol·g ) is the amount of adsorbent adsorbed at time t, qe (mol·g−1) is the amount of adsorbent adsorbed at equilibrium and k1 (min−1) and k2 (g·mol−1·min−1) are the adsorption rate constants. The qe and k1 and k2 were obtained from the slope and intercept of linear plots between ln (qe − qt) versus t and (t/qt) versus t. Table 2 shows the values calculated from these plots. The regression coefficient (R2) values suggest that experimental data better follows pseudo-second-order kinetics than pseudo-first-order kinetics. Reichenberg equation (eq 9) was used to test the adsorption process, whether adsorption is film diffusion or intraparticle. Q=1−

6e−Bt π2

ln kc =

ΔG = −RT ln kc

Rearranging the above equation in linear form we get Bt = −0.4977 − ln(1 − Q )

where Q = qt/qm, Bt = π2Di/r2, qt and qm are adsorbed concentration at time t and the maximum adsorption capacity, and Di is the effective diffusion coefficient of the sorbate species inside the sorbate particle. Di increases with increasing temperature because at higher temperature particle diameter increases, and as the size of effective binding sites increases, more adsorbate will adsorb on the resin. From the linear plot of Bt versus time t (Figure 7) the intercept values achieved are above the origin, −0.078, −0.0394, and −0.2055, respectively, which means that the intraparticle diffusion is a rate controlling step with a small friction of adsorption that occurs through film diffusion. The Morris−Weber equation was also used to explore the kinetic adsorption process. (10)

where qt is the adsorbed concentration at time t, and Rd is intraparticle diffusion rate constant. The linear plot of qt versus √t (Figure 8) shows that intraparticle diffusion occurs and the line does not pass through the origin, which means the intraparticle diffusion is not the only rate limiting parameter controlling the process. The value of Rd from the slope was calculated as 0.0088 mmol·g−1·min−1/2 (293 K), 0.010 mmol· g−1·min −1/2 (303 K) and 0.0125 mmol·g−1·min −1/2 (313 K) with R2 values 0.987, 0.947, and 0.987, respectively. The value of Rd increases with increasing temperature because more collisions will occur at higher temperature between adsobate/ ion. Thermodynamics of Adsorption. The adsorption of perchlorate on to resin-5 was analyzed at different temperatures. It is noticed that as temperature increases the adsorption capacity value increases (Figure 9). The obtained values from the plot are 0.117 (293 K), 0.1513 (303 K), and 0.1784 mmol· g−1 (313 K), respectively. The temperature effect was analyzed by using the Arrhenius equation at optimized conditions, ln k1 = ln Ao +

Ea RT

(12) (13)

The evaluated thermodynamic parameters, change in enthalpy ΔH (kJ·mol−1), change in entropy ΔS (kJ·mol−1· K−1), and change in free energy ΔG (kJ·mol−1) are listed in Table 3. The negative value of ΔG shows the possibility of the adsorption process, and the decrease in ΔG values with an increase in temperature specifies the spontaneity of the process at higher temperature. The positive value of ΔH confirms the endothermic process, and ΔS reveals that there is good affinity of perchlorate toward resin-5. Interference Effect. A study has evaluated the effect of interference on the adsorption efficiency of resin-5 of selected anions such as fluoride, chloride, bromide and oxyanions such as, nitrite, nitrate, sulfate, and phosphate in varying concentration ratios with respect to perchlorate (Figure 12) by keeping other parameters constant. The experimental results show that there is no major effect of these ions except sulfate and nitrite for the removal of perchlorate by resin-5. Reusability of Resin. The regeneration of resin-5 is possible with the use of different concentrations of HCl, since at particularly low pH, chloride contends with perchlorate for the available adsorption sites onto the resin-5. Thus, the complete desorption of perchlorate under extreme acidic environments can be clarified by the fact that the resin-5 contains calix[4]arene derivatives with amino binding sites and hence possesses the capability of forming hydrogen bonds with anions. The proposed perchlorate adsorption/desorption mechanism by resin-5 is shown in Scheme 3.

(9)

qt = R d t

−ΔH ΔS + RT R

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CONCLUSION It could be concluded that calix[4]arene based Amberlite XAD4 resin (Resin-5) is an efficient adsorbent material for the removal of perchlorate from aqueous media. The isotherm models, and kinetic and thermodynamic studies further confirm the experimental results. The maximum adsorption of perchlorate could be achieved at pH 4.5. Hopefully, this study will find its applicability in various disciplines such as analytical, environmental, and industrial fields.

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AUTHOR INFORMATION

Corresponding Author

*Tel.: +92 (22) 9213430. Fax: +92 (22) 9213431. E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS We are highly thankful to the National Centre of Excellence in Analytical Chemistry, University of Sindh, Jamshoro (Project No. NCEAC/246/2010) for financial support.

(11)

where Ao (1/min) is the “frequency factor” and independent of temperature, Ea (kJ·mol−1) is the activation energy, R (8.314 J· G



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