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Adsorption of Volatile Organic Compounds on Zeolite L Ana C. Fernandes and Joaõ Pires* Department of Chemistry and Biochemistry, Faculty of Science, University of Lisbon, 1749-016 Lisbon, Portugal S Supporting Information *

ABSTRACT: The adsorption properties of commercial zeolite L for various types of probe molecules selected from different families of volatile organic compounds were studied. The probe molecules had various sizes and polarities and included hexane isomers (n-hexane and cyclohexane), aromatic molecules (benzene and toluene), oxygenated molecules (ethanol, acetone, and methyl ethyl ketone), and a chlorinated molecule (trichloroethane). The adsorption isotherms were determined at two temperatures and modeled by the Dubinin−Astakhov (DA) and Tóth equations. The DA equation was applicable for a broader range of experimental conditions.

until reaching high temperatures,21 even if in some cases they can present lower adsorption capacities than, for instance, carbonaceous-based materials.20 In the present work, we study the adsorption properties of commercial zeolite L for various types of probe molecules selected from different families of VOCs, such as hexane isomers (n-hexane and cyclohexane), aromatic molecules (benzene and toluene), oxygenated molecules (ethanol, acetone, and methyl ethyl ketone), and a chlorinated molecule (trichloroethane). The adsorption isotherms were determined at two temperatures and modeled by the Dubinin−Astakhov (DA) and Tóth equations.25−27

1. INTRODUCTION Zeolites are microporous materials (pore width less than 2 nm1). Considering their composition, zeolites are mostly aluminosilicates, but the definition also includes aluminophosphates and some types of silicas.2 These solids have been known for a long time, and their unique properties, based on a variety of topologies,3 means the commercial relevance of these materials has been demonstrated for a wide range of applications in areas spanning from catalysis and selective adsorption to energy and medicine.2,4−6 In recent years, attention has been given to a relatively restricted number of zeolites regarding aspects of structural modification and new synthesis methodologies for changing the porosity and tuning crystal size and shape.6,7 This is the case for zeolite L.8−12 This zeolite has a one-dimensional pore structure of approximately 0.71 nm aperture, leading to cavities of approximately 0.48 × 1.24 × 1.07 nm.3,12 Zeolite L (LTL) is commercially used as a catalyst in hydrocarbon cyclization and aromatization, and potential applications include adsorption, photonic devices, and drug delivery.4 It is fair to say that, among all of the effective or potential applications of zeolite L, its adsorption properties are involved, if not totally, at least to a certain extent. Nevertheless, the number of adsorption studies in zeolite L, particularly related to the adsorption of volatile organic compounds (VOCs), is restricted.10,13−15 VOCs are among the most common air pollutants emitted from chemical, petrochemical, and related industries16 and are defined as all organic compounds (except methane) with a vapor pressure equal to or higher than 0.01 kPa at 293 K.17 The consequences for the environment and human health of VOC emissions are well known.16,18,19 Among the methodologies to reduce the VOC content in ambient air, adsorption is one of the least expensive methods with a removal efficiency higher than 90%.16 Studies of adsorption of VOCs in zeolitic materials other than zeolite L, and also in other adsorbent types such as carbonaceous-based materials, have been presented previously18,20−24 Important in this context of the adsorption of VOCs, which are frequently flammable substances, is the fact that zeolitic structures are stable © XXXX American Chemical Society

2. MATERIALS AND METHODS Zeolite L was the ZEOcat L from Zeochem with a molar SiO2/ AI2O3 ratio of 5.9 and a crystal size between 1 and 2 μm. The sample is highly crystalline, as denoted by the X-ray diffractogram in Figure S1, and microporous, as shown by the nitrogen adsorption isotherm at 77 K in Figure S2. The specific surface area of this zeolite (BET method) is 322 m2 g−1, and the microporous volume is 0.136 cm3 g−1. The X-ray diffractogram was obtained in a PW 1710 diffractometer with automatic data acquisition (APD Phillips (v.35B) software) and Cu Kα (λ = 1.5406 Å) radiation. The nitrogen adsorption isotherm at 77 K was determined in an automatic apparatus (Micromeritics, mod. ASAP 2010, pressure reading sensitivity of 0.001 kPa). Prior to adsorption, the zeolite was outgassed at 523 K with a vacuum better than 0.001 kPa for 3 h. The adsorptions of the hydrocarbon vapors of acetone (BDH, 99.5%), ethanol (Carlo Erba, 99.9%), benzene (BDH, 95%), toluene (Aldrich, 99.8%), n-hexane (nC6; Merck, 99.0%), cyclohexane (cycloC6; Sigma-Aldrich, 99.7%), methyl ethyl ketone (MEK; BDH, 99.5%), and 1,1,1-trichloroethane (TCA; Received: July 12, 2016 Accepted: September 29, 2016

A

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Aldrich, 99%) were studied using a microbalance (C.I. Electronics), which allowed a precision of 10 μg. The pressure readings were made with a pressure transducer (Pfeiffer Vacuum CMR 262). Prior to the measurements, the samples were outgassed for 3 h at 300 K under high vacuum. The lowest sensitivity of the pressure sensor was 0.0001 kPa (0.1 Pa), but to ensure high quality data, only pressure readings higher than 0.01 kPa (that is, 100 times higher the lowest sensor sensitivity) were recorded. The adsorption temperature was maintained by a thermostatic water bath (Grant Instrument GD-120) at 298 and 308 ± 0.1 K. The hydrocarbons were purified by conducting freezing-vacuum-thawing cycles. The reproducibility in the determination of the amounts adsorbed was better than 5%.

3. RESULTS AND DISCUSSION The adsorption isotherms are plotted at 298 and 308 K for the VOCs TCA (Figure 1), cycloC6 (Figure 2), ethanol (Figure 3), Figure 3. Adsorption isotherms of ethanol in zeolite L at the indicated temperatures. Dotted and broken lines are fittings to Toth and DA equations, respectively.

MEK (Figure 4), nC6 (Figure 5), benzene (Figure 6), toluene (Figure 7), and acetone (Figure 8), and the data are presented in

Figure 1. Adsorption isotherms of TCA in zeolite L. Dotted and broken lines are fittings to Toth (298 K) and DA (298 and 308 K) equations, respectively.

Figure 4. Adsorption isotherms of MEK in zeolite L. Dotted and broken lines are fittings to Toth (308 K) and DA (298 and 308 K) equations, respectively.

Tables 1−8, respectively. As expected, in agreement with the microporous structure of zeolite L, the isotherms are of type I according to the IUPAC classification.1 The steep adsorption at low pressures, characteristic of type I isotherms, indicates that zeolite L could be a material suitable to adsorb/remove even very low vapor concentrations of VOCs. Analyses of the VOC adsorption isotherms were made by the Dubinin−Astakhov (DA) and Tóth equations.25−27 The DA equation has been extensively applied to the adsorption of vapors in microporous materials.22,27,28 Additionally, the Tóth equation, although originally proposed for monolayer adsorption, is believed to give a more extensive range of fit than the Langmuir or Freundlich isotherm equations when applied to type I isotherms for microporous adsorbents.26,29,30 The Tóth equation also has the advantage over the Sips equation in that it appears to

Figure 2. Adsorption isotherms of cycloC6 in zeolite L at the indicated temperatures. Dotted and broken lines are fittings to Toth and DA equations, respectively.

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Figure 5. Adsorption isotherms of nC6 in zeolite L at the indicated temperatures. Dotted and broken lines are fittings to Toth and DA equations, respectively.

Figure 7. Adsorption isotherms of toluene in zeolite L at the indicated temperatures. Dotted and broken lines are fittings to Toth and DA equations, respectively.

Figure 6. Adsorption isotherm of benzene in zeolite L. Dotted and broken lines are fittings to Toth (298 K) and DA (298 and 308 K) equations, respectively.

Figure 8. Adsorption isotherms of acetone in zeolite L. Dotted and broken lines are fittings to Toth (308 K) and DA (298 and 308 K) equations, respectively.

satisfy the thermodynamic limits.29,30 The DA equation had an empirical nature when proposed, however, some authors consider that the DA equation can have a theoretical justification.31 This equation has the form

related to the heterogeneity of the adsorption system.26 When t = 1, eq 2 reduces to the Langmuir equation, that is, to a system with homogeneous adsorption sites. Fittings of the data to eqs 1 and 2 were made using the OriginPro (version 8) software using the nonlinear curve fit methodology and are shown in Figures 1−8 for the respective organic vapors, and the fitting parameters are collected in Tables 9 (DA) and 10 (Tóth). The quality of the fits can be evaluated by the average percent deviations, Δq1, and the degree of dispersion, Δq2

⎛ A ⎞n q = qmexp −⎜ ⎟ ⎝E⎠

(1)

where q is the amount adsorbed at temperature T and relative pressure p/p0, qm is the limiting adsorption in the micropores, A is the adsorption potential (A = RT ln(P0/P)), and n and E are temperature invariant parameters. The Tóth equation has the form q = q0 ×

bP (1 + (bP)t )1/ t

Δq1 (%) =

(2)

Δq2 (%) =

0

where P is the pressure, q is the amount adsorbed, and q is the maximum adsorbed amount. In eq 2, the parameters b and t are specific for adsorbate−adsorbent pairs with the latter being

k

100 k



100 k



n=1 k n=1

|nexp − ncalc| nexp

(3)

(nexp − ncalc)2 nexp

(4)

where k is the total number of experimental values. C

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Table 1. Adsorption Isotherm Data of TCA 298 K

308 K

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

0.031 0.063 0.096 0.135 0.168 0.203 0.267

0.150 0.550 0.732 0.774 0.796 0.812 0.835

0.397 0.633 1.031 2.733 5.030 9.067

0.857 0.892 0.918 0.967 0.991 1.008

0.035 0.069 0.120 0.223 0.329 0.545

0.687 0.733 0.762 0.780 0.797 0.811

0.795 1.191 1.852 3.129 5.662

0.827 0.852 0.885 0.938 0.986

Table 2. Adsorption Isotherm Data of CycloC6 298 K

308 K

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

0.044 0.080 0.116 0.157 0.207 0.252

0.584 0.642 0.674 0.715 0.751 0.770

0.397 0.651 1.189 2.746 5.000

0.802 0.830 0.860 0.913 0.928

0.035 0.064 0.103 0.132 0.171 0.200 0.267

0.633 0.678 0.705 0.721 0.735 0.743 0.757

0.423 0.813 1.475 2.997 6.061 9.113

0.776 0.807 0.833 0.859 0.883 0.896

Table 3. Adsorption Isotherm Data of Ethanol 298 K

308 K

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

0.123 0.427 0.673 1.084

1.911 2.061 2.095 2.132

1.773 3.079 4.827 5.949

2.166 2.205 2.256 2.267

0.208 0.302 0.655 1.080

1.694 1.759 1.843 1.877

1.737 3.079 4.832 6.227

1.910 1.944 1.983 2.014

Table 4. Adsorption Isotherm Data of MEK 298 K

308 K

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

0.208 0.655 1.290 2.390 4.147

1.485 1.541 1.562 1.599 1.618

5.690 6.973 8.512 10.274

1.636 1.661 1.680 1.701

0.208 0.342 0.905 1.500 2.166

1.245 1.286 1.334 1.356 1.375

3.499 5.265 7.881 10.546

1.392 1.421 1.410 1.419

Table 5. Adsorption Isotherm Data of nC6 298 K −1

308 K −1

−1

P (kPa)

q (mol kg )

P (kPa)

q (mol kg )

P (kPa)

q (mol kg )

P (kPa)

q (mol kg−1)

0.199 0.333 0.391 0.588 1.303

0.759 0.796 0.808 0.814 0.839

2.037 2.412 3.964 5.784 14.759

0.848 0.855 0.862 0.869 0.875

0.194 0.324 0.405 0.646 1.268

0.748 0.794 0.818 0.820 0.841

2.560 4.322 6.186 8.923 12.912

0.863 0.876 0.888 0.899 0.913

Table 6. Adsorption Isotherm Data of Benzene 298.15 K

308.15 K

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

0.094 0.196 0.382 0.544 1.171

0.434 1.089 1.112 1.122 1.140

2.012 3.304 5.002 7.065

1.154 1.166 1.171 1.178

0.135 0.268 0.501 0.931 1.585

1.058 1.070 1.089 1.101 1.119

2.364 3.275 4.628 6.666 8.497

1.129 1.140 1.146 1.143 1.165

D

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Table 7. Adsorption Isotherm Data of Toluene 298.15 K

308.15 K

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

P (kPa)

q (mol kg−1)

0.092 0.250 0.501 0.824

1.035 1.064 1.084 1.094

1.265 1.766 2.189

1.101 1.109 1.116

0.074 0.155 0.277 0.493 0.548

0.970 0.997 1.032 1.050 1.052

1.229 1.711 2.242 2.460

1.066 1.074 1.080 1.092

Table 8. Adsorption Isotherm Data of Acetone 298.15 K −1

308.15 K −1

−1

P (kPa)

q (mol kg )

P (kPa)

q (mol kg )

P (kPa)

q (mol kg )

P (kPa)

q (mol kg−1)

0.073 0.211 0.797 2.133

1.546 1.581 1.625 1.664

3.945 6.555 10.475

1.697 1.721 1.746

0.053 0.099 0.239 0.528

0.555 1.357 1.553 1.590

1.949 3.961 6.726 10.664

1.640 1.675 1.700 1.724

Table 9. DA Equation Parameters for the Studied Vapors TCA cycloC6 ethanol MEK nC6 benzene toluene acetone

T (K)

qm (mol kg−1)

E (kJ mol−1)

n

Δq1 (%)

Δq2 (%)

r2a

298 308 298 308 298 308 298 308 298 308 298 308 298 308 298 308

0.937 1.379 0.932 0.900 2.271 2.022 1.733 1.426 0.872 0.910 1.150 1.179 1.121 1.090 1.852 1.654

14.894 43.645 18.622 30.478 39.240 31.972 21.185 35.195 26.032 33.388 12.179 10.252 60.699 34.172 20.595 16.207

7.917 0.405 2.276 1.721 1.332 1.626 0.621 1.812 2.484 1.840 17.276 1.057 1.346 1.938 0.653 15.907

6.746 0.738 0.780 0.412 0.406 0.323 0.270 0.334 0.446 0.883 1.423 0.296 0.109 0.399 0.088 2.516

0.319 0.006 0.007 0.002 0.004 0.004 0.002 0.003 0.002 0.011 0.035 0.002 0.000 0.002 0.000 0.139

0.952 0.992 0.994 0.998 0.989 0.984 0.986 0.992 0.980 0.954 0.989 0.978 0.995 0.979 0.999 0.976

a 2

r , regression coefficient.

Table 10. Tóth Equation Parameters for the Studied Vapors

TCA cycloC6 ethanol MEK nC6 benzene toluene acetone

T (K)

q0 (mol kg−1)

b (kPa)

t

Δq1 (%)

Δq2 (%)

r2a

298 n. a. 298 308 298 308 n. a. 308 298 308 298 n. a. 298 308 n. a. 308

0.945 n. a. 1.011 1.026 2.617 2.194 n. a. 1.492 0.884 0.954 1.148 n. a. 1.221 1.136 n. a. 1.646

10.091 n. a. 522.317 318346.166 6.988 × 106 20093.037 n. a. 13859.057 267.033 6111.340 4.539 n. a. 1.025 × 109 32240.958 n. a. 7.584

1.938 n. a. 0.422 0.231 0.201 0.303 n. a. 0.345 0.600 0.352 178.855 n. a. 0.188 0.363 n. a. 86.221

14.265 n. a. 0.813 0.225 0.326 0.459 n. a. 0.331 0.351 0.829 10.992 n. a. 0.096 0.401 n. a. 11.145

2.382 n. a. 0.006 0.001 0.003 0.005 n. a. 0.003 0.002 0.009 2.03 n. a. 0 0.002 n. a. 2.739

0.879 n. a. 0.995 0.999 0.993 0.988 n. a. 0.984 0.987 0.962 0.657 n. a. 0.997 0.980 n. a. 0.774

a 2

r , regression coefficient.

From the results in Figures 1−8 and the values in Tables 9 and 10, it can be seen that, in general, the DA equation is more widely

applicable to the studied VOCs than the Tóth equation. It was possible to fit the DA equation to all vapors with low average E

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(7) Serrano, D. P.; Escola, J. M.; Pizarro, P. Synthesis strategies in the search for hierarchical zeolites. Chem. Soc. Rev. 2013, 42, 4004−4035. (8) Meeprasert, J.; Jungsuttiwong, S.; Namuangruk, S. Location and acidity of Bronsted acid sites in isomorphously substituted LTL zeolite: A periodic density functional study. Microporous Mesoporous Mater. 2013, 175, 99−106. (9) Gomez, A. G.; de Silveira, G.; Doan, H.; Cheng, C.-H. A facile method to tune zeolite L crystals with low aspect ratio. Chem. Commun. 2011, 47, 5876−5878. (10) Saepurahman; Singaravel, G. P.; Hashaikeh, R. Fabrication of electrospun LTL zeolite fibers and their application for dye removal. J. Mater. Sci. 2016, 51, 1133−1141. (11) Lupulescu, A. I.; Kumar, M.; Rimer, J. D. A Facile Strategy To Design Zeolite L Crystals with Tunable Morphology and Surface Architecture. J. Am. Chem. Soc. 2013, 135, 6608−6617. (12) Wang, Y.; Lv, T.; Ma, Y.; Tian, F.; Shi, L.; Liu, X.; Meng, C. Synthesis and characterization of zeolite L prepared from hydrothermal conversion of magadiite. Microporous Mesoporous Mater. 2016, 228, 86− 93. (13) Hansenne, C.; Jousse, F.; Leherte, L.; Vercauteren, D. P. Dynamics of benzene in zeolite KL. J. Mol. Catal. A: Chem. 2001, 166, 147−165. (14) Su, B. L.; Norberg, V.; Hansenne, C.; De Mallmann, A. Toward a better understanding on the adsorption behavior of aromatics in 12R window zeolites. Adsorption 2000, 6, 61−71. (15) Wang, H. Y.; Turner, E. A.; Huang, Y. N. Investigations of the adsorption of n-pentane in several representative zeolites. J. Phys. Chem. B 2006, 110, 8240−8249. (16) Khan, F. I.; Ghoshal, A. K. Removal of Volatile Organic Compounds from polluted air. J. Loss Prev. Process Ind. 2000, 13, 527− 545. (17) Pires, J.; Carvalho, A.; Veloso, P.; de Carvalho, M. B. Preparation of dealuminated faujasites for adsorption of volatile organic compunds. J. Mater. Chem. 2002, 12, 3100−3104. (18) Canet, X.; Gilles, F.; Su, B. L.; de Weireld, G.; Frere, M. Adsorption of Alkanes and aromatic compounds on various faujasites in the henry domain. 1. Compensating cation effect on Zeolites Y. J. Chem. Eng. Data 2007, 52, 2117−2126. (19) de Gennaro, G.; Farella, G.; Marzocca, A.; Mazzone, A.; Tutino, M. Indoor and Outdoor Monitoring of Volatile Organic Compounds in School Buildings: Indicators Based on Health Risk Assessment to Single out Critical Issues. Int. J. Environ. Res. Public Health 2013, 10, 6273− 6291. (20) Benkhedda, J.; Jaubert, J.-N.; Barth, D. Experimental and Modeled Results Describing the Adsorption of Toluene onto Activated Carbon. J. Chem. Eng. Data 2000, 45, 650−653. (21) Brihi, T. E.; Jaubert, J.-N.; Barth, D. Determining Volatile Organic Compounds’ Adsorption Isotherms on Dealuminated Y Zeolite and Correlation with Different Models. J. Chem. Eng. Data 2002, 47, 1553− 1557. (22) Pires, J.; Pinto, M.; Carvalho, A.; de Carvalho, M. B. Adsorption of acetone, methyl ethyl ketone, 1,1,1-trichloroethane, and trichloroethylene in granular activated carbons. J. Chem. Eng. Data 2003, 48, 416−420. (23) Wu, J.; Zhang, L.; Long, C.; Zhang, Q. Adsorption Characteristics of Pentane, Hexane, and Heptane: Comparison of Hydrophobic Hypercrosslinked Polymeric Adsorbent with Activated Carbon. J. Chem. Eng. Data 2012, 57, 3426−3433. (24) Clausse, B.; Garrot, B.; Cornier, C.; Paulin, C.; Simonot-Grange, M. H.; Boutros, F. Adsorption of chlorinated volatile organic compounds on hydrophobic faujasite: correlation between the thermodynamic and kinetic properties and the prediction of air cleaning. Microporous Mesoporous Mater. 1998, 25, 169−177. (25) Rouquerol, F.; Rouquerol, J.; Sing, K. Adsorption by Powders and Porous Solids; Academic Press: London, UK, 1999. (26) Do, D. D. Adsorption Analysis: Equilibria and Kinetics; Imperial College Press: London, UK, 1998. (27) Stoeckli, F. Recent Developments in Dubinin’s Theory. Carbon 1998, 36, 363−368.

deviation values, in fact, lower than 1% except for three VOCs at three temperatures (TCA, benzene, and acetone) and in these, only one case was higher than 5%, which are results that compare very favorable with the literature.28,32 In the case of the Tóth equation, not only were the average deviations high (14.3% for the highest value), but for various systems (Table 10), the fitting was also not acceptable due to unreliable high values of the b parameter. The maximum adsorbed amounts estimated from the DA equation at the lowest temperature, when expressed in percentage of mass, vary from 8% (cycloC6) to 12.5% (TCA). These values are lower than those found for other zeolites, namely, faujasite-type zeolites,24,33 but nevertheless, the values are in line with the respective total microporous volume, which is less in the case of zeolite L (0.136 cm3 g−1 as already mentioned in the Materials and Methods).

4. CONCLUSIONS The adsorption of a series of volatile organic compounds of various sizes and polarities, such as 1,1,1-trichloroethane, cyclohexane, ethanol, acetone, methylethylketone, n-hexane, benzene, toluene, and acetone in zeolite L at temperatures near ambient temperature showed that this zeolite can adsorb between 8 and 12.5% in weight and, most importantly, that the adsorption occurs mainly at low pressure, a property that has relevance for air cleaning or sensing applications. The adsorption isotherms can be adequately described by the Dubinin− Astakhov equation, which except in one case gave average deviation values of less than 3%.



ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.6b00624. X-ray diffractogram of the studied zeolite L and nitrogen adsorption isotherm at 77 K (PDF)



AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected] Tel.: +351 217 500 903. Funding

The authors thank the Foundation for Science and Technology (FCT) for funding CQB UID/MULTI/00612/2013. Notes

The authors declare no competing financial interest.



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