Solubility of Hydrogen Chloride in Three 1-Alkyl-3-methylimidazolium

Oct 23, 2012 - To study the possibility of using ionic liquids (ILs) as a novel solvent for the absorption of hydrogen chloride (HCl) from the industr...
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Solubility of Hydrogen Chloride in Three 1‑Alkyl-3methylimidazolium Chloride Ionic Liquids in the Pressure Range (0 to 100) kPa and Temperature Range (298.15 to 363.15) K Ru-Hao He,†,‡ Bing-Wen Long,‡ Ying-Zhou Lu,‡ Hong Meng,‡ and Chun-Xi Li*,†,‡ †

State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. China College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. China

‡

S Supporting Information *

ABSTRACT: To study the possibility of using ionic liquids (ILs) as a novel solvent for the absorption of hydrogen chloride (HCl) from the industrial tail gases, the solubility of HCl gas in three ILs has been measured at four temperatures, (298.15, 323.15, 348.15, and 363.15) K, in the pressure range of (0 to 100) kPa. The ILs used are 1-butyl-3-methylimidazolium chloride ([Bmim]Cl), 1-hexyl-3-methylimidazolium chloride ([Hmim]Cl), and 1-octyl-3-methylimidazolium chloride ([Omim]Cl). The results indicate that these ILs show high solubility for HCl gas, and the solubility decreases with the increasing length of the alkyl substitutes of the ILs, following the order [Bmim]Cl > [Hmim]Cl > [Omim]Cl. The solubility of HCl in [Bmim]Cl at 298.15 K is about 0.68 mole fraction at ca. 100 kPa partial pressure of HCl, which is much higher than that of 36.5 % HCl aqueous solution. The solubility of different ILs is discussed in detail, and the experimental data (P−T−x) are correlated successfully by an empirical relation.

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INTRODUCTION Hydrogen chloride (HCl) is often produced as a byproduct in many chlorination and dechlorination reactions in pharmaceutical and chemical processes. HCl is irritative, corrosive, and harmful to the environment and human health, and thus its corresponding tail gas is generally treated by water absorption. Besides, it is also an important raw material for the production of many volume chemicals in chemical industry, for example, vinyl chloride monomer, methyl chloride, and other alkyl chlorides, and so forth. In general, batch-wise absorption is used for the treatment of a small amount of such tail gases, and the resulting dilute hydrochloric acid is obtained as a low value byproduct or directly neutralized with limestone or waste alkali solution before discharging, while for the continuous and large amount of such tail gases, a multistage or successive absorption unit is used for producing concentrated hydrochloric acids for sale or as raw material for the production of anhydrous HCl via special rectification. Although the water absorption process is a well-developed technology and widely used, the desorption process for reclaiming anhydrous HCl needs intensive energy and capital cost due to the azeotropic phenomena, volatility of water, and serious corrosiveness. Therefore, it is necessary to develop an alternative way for treating HCl-containing tail gases, especially for efficiently producing high purity anhydrous HCl. To achieve this, the key is to find an appropriate solvent that has negligible volatility and high solubility for HCl gas. In this work, ionic liquids (ILs) are considered as competitive candidates, and their solubility to HCl is investigated. © XXXX American Chemical Society

ILs are molten salts, which are liquid over a wide temperature range including ambient.1 In recent years, ILs have gained great attention in a variety of chemical processes due to their favorable properties,2−6 such as negligible vapor pressures, high thermal stability, and tunable solubility for both polar and nonpolar substances. A promising application of ILs is for gas separation and purification, since the nonvolatility of ILs would not bring any contamination to a gas stream and the dissolved gas can be reclaimed easily by heating under reduced pressure, which makes ILs more competitive than the conventional solvents. As a results, ILs have been studied for the absorption of many industrial gases, such as CO2,7,8 SO2,9 CO,10 H2,11 NH3,12 H2S,13 and so forth. However, no experimental data for the solubility of HCl in ILs are reported. In this work, we have investigated the solubility of HCl in three ILs, namely, [Bmim]Cl, [Hmim]Cl, and [Omim]Cl, at four temperatures (298.15, 323.18, 348.15, and 363.15) K in the pressure range of (0 to 100) kPa. A high solubility of HCl in these ILs has been found. The experimental data in terms of pressure−temperature−composition (P−T−x) have been well correlated by an empirical model, and the Henry’s law constants have been calculated. Received: March 29, 2012 Accepted: October 16, 2012

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EXPERIMENTAL SECTION Chemicals. High-purity hydrogen chloride (purity > 99.99 %) was obtained from Beijing Chemical Works. The ILs [Bmin]Cl, [Hmim]Cl, and [Omim]Cl were prepared and purified in the laboratory according to the method described in the literature.14 The chemicals used for synthesizing these ILs are 1-methylimidazole (≥ 99.5 wt %, Zhejiang Kaile Reagents Company, China), 1-chlorobutane (≥ 98.5 wt %, Tianjin Guangfu Fine Chemical Research Institute, China), 1chlorohexane (≥ 98.0 wt %, Aladdin Chemical Reagent), and 1-chlorooctane (≥ 99.0 wt %, Aladdin Chemical Reagent). The prepared ILs were dried under vacuum at 373.15 K for 24 h before use, and the quantity of water was milli-Q as determined by the Karl Fisher titrator (type CBS-1A). Their purities in mole fraction were better than 99 % as determined by the NMR analysis (see Supporting Information). Apparatus and Solubility Measurement. The experimental setup used in this work for solubility measurements is shown schematically in Figure 1. The apparatus comprises an

vibrating tube densimeter (DMA 4500M, Anton Paar Co. Ltd., Austria), as shown in Table 1. Table 1. Density ρ of [Bmim]Cl, [Hmim]Cl, and [Omim]Cl at Different Temperaturesa ρ/(g·cm−3) ILs

T = 298.15 K

[BMIM]Cl [HMIM]Cl [OMIM]Cl

1.08159 1.04092 1.01235

a

T = 323.15 K T = 348.15 K 1.06728 1.02673 0.99805

T = 363.15 K

1.05335 1.01281 0.98399

1.04506 1.00449 0.97567

Uncertainties are: U(ρ) = 1·10−5 g·cm−3; U(T) = 0.01 K.

The whole system, as shown in Figure 1, is vacuumed using the vacuum pump for 12 h, and the system temperature is adjusted to the desired value. The valves to the vacuum pump (V4) and the equilibrium cell (V3) are closed first, and then HCl gas is charged slowly into the storage tank by opening valves V1 and V2 carefully until a specific absolute pressure. The initial amount of the HCl gas in the storage tank is determined using the PVT relation by pressure measurements.15 In the follow-up absorption experiment, the valve V3 to the equilibrium cell is opened partially to charge the equilibrium cell gradually to a certain extent and then closed. The pressure of the storage tank is read again, whereby the amount of HCl charged to the equilibrium cell can be determined in terms of the pressure drop. As soon as the gas entered into the equilibrium cell, it is absorbed by the ILs, resulting in a decreasing pressure in the equilibrium cell until the absorption equilibrium. Then the pressure of the equilibrium cell is read to determine the amount of HCl gas left in vapor phase. The difference of HCl gas in the equilibrium cell is taken as the amount dissolved.15 The overall uncertainties in the solubility data due to both random and systematic errors have been estimated to be less than 0.003 mole fraction at given T and P. The amount of HCl charged to the equilibrium cell Δn is given as

Figure 1. Experimental apparatus for solubility measurement. 1, vacuum pump; 2, HCl gas container; 3, storage tank; 4, equilibrium cell; 5, magnetic stirrer; 6, water bath; 7, U-shape pressure gauge.

Δn = n1 − n2

HCl gas container, a storage tank, and an equilibrium cell. The pressure of the storage tank is measured using a digital pressure gauge (ZD-100, Beijing Taiweizhida Meters Technology Co. Ltd. China) in the range of (0 to 200) kPa, and the accuracy is within 0.1 kPa. In the cell, a magnetic rotor is used to accelerate the absorption equilibrium. The gas pressure of equilibrium cell is measured by a U-shape pressure gauge, in which mercury is filled as the indicating liquid and the same amount of liquid paraffin is added to both arms of the tube to prevent the loss of mercury and the pollution to the environment. The accuracy of gas pressure is about 0.133 kPa being consistent with 1 mm height of mercury column. The storage tank and equilibrium cell were placed inside a water bath (CH1015, Shanghai Hengping Meters Factory, China), whose accuracy is claimed within ± 0.1 K. The internal volume of the whole system is demarcated accurately in advance with water, and the uncertainty is within ± 0.1 mL. The ILs were dried under vacuum at 373.15 K and 0.1 kPa for 24 h before use. An accurate amount of ILs (about 4 to 8 g) weighed by an electronic balance with uncertainty of ± 0.001 g is added to the equilibrium cell, and the volume of ILs is calculated from the measured mass and density of ILs. The density is determined in separate measurements with the digital

(1)

where n1 and n2 are the moles of HCl in the storage tank before and after charged to the equilibrium cell. The mole of HCl dissolved in the equilibrium cell ng is given as ng = Δn − n E

(2)

E

where n is the mole of HCl gas left in the vapor phase of the equilibrium cell. The mole fraction of HCl in ILs x at given temperature T and pressure P is given as ng x= ng + nL (3) where nL is the amount of ILs in moles.

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RESULTS AND DISCUSSION The reliability of the present experiment is confirmed by the measured solubility data of HCl in 1,2,4-trimethylbenzene in the pressure range of (0 to 103) kPa at (303.15 and 323.15) K. The results are shown in Figure 2 and compared with the literature data.16 The average of percent deviations were 0.045 B

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Cl > [Omim]Cl, although the difference among them is relatively small. It is thus inferred that the solubility of HCl in these ILs decreases with the increasing alkyl length of the cations of 1-alkyl-3-methylimidazolium chlorides. Modeling. As shown in Figure 4, the solubility of HCl in these ILs in terms of mol-HCl/g ILs is much lower than that in water17 but exhibits similar solubility characteristics. It is wellknown that the apparent total solubility of HCl in water can be resolved into two parts, namely, a chemical reactive dissolution part and a physical dissolution part, and the former plays a dominant role for the high solubility of HCl. More specifically, the chemical dissolution herein is associated with the chemical reaction between HCl and water forming H3O+ and Cl− ions until reaching an ionization equilibrium, while the physical part represents the gas dissolution in its molecular form rather than in any of other species. In comparison with the chemical reactive dissolution, the physical one shows stronger pressure dependence and is often represented by the Henry’s law in a narrow pressure range. For representing our experimental solubility of HCl in these ILs, the model proposed by Islam18 is adopted in this work which accounts for both the chemical reactive dissolution and the physical dissolution in one equation and is proved to be effective for most reactive gases. It is given as

Figure 2. Comparison of the measured solubility data of this work on HCl + 1,2,4-trimethylbenzene with the literature at (303.15 and 323.15) K: ■, this work at 303.15 K; ▲, this work at 323.15 K; □, literature at 303.15 K; △, literature at 323.15 K.

% and 0.017 % at (303.15 and 333.15) K, respectively. Obviously, the data of this work agree well with the literature ones in the whole temperature and pressure ranges studied. The experimental solubility data of hydrogen chloride in three ILs at temperatures of (298.15, 323.15, 348.15, and 363.15) K and pressures up to 100 kPa are summarized in Tables 2, 3, and 4, respectively. To show the global influence of temperature and pressure on the solubility of HCl in these ILs, the experimental data for [Bmim]Cl is presented in Figure 3 as a representative. It is seen that the solubility of HCl increases with the increasing pressure of HCl and decreases with increasing temperature, which follows the general gas solubility rule in liquid. At a specified temperature but varying with pressure, the solubility of HCl is observed to first undergo a drastic increase with pressure, reaching a very high level before 20 kPa, and then increases mildly especially in the higher pressure range. This solubility behavior is quite different with that showing in Figure 2 indicating the solubility mechanism of HCl in the ILs is more complicated than that in 1,2,4trimethylbenzene. The solubility of HCl in three ILs in mol-HCl/g ILs at 323.15 K is presented in Figure 4. It is clear that the solubility of HCl in these ILs follows the order of [Bmim]Cl > [Hmim]

x = xe

P + aP b+P

(4)

where x is the total solubility in mole fraction and P is the equilibrated gas pressure. The first term in the right-hand side of eq 4 represents the contribution from the chemical reactive dissolution, which is expressed by the Langmuir equation, and xe is the Langmuir saturated solubility. The second term stands for the contribution from the physical dissolution, which is expressed by the Henry’s law and parameter a relates the Henry’s constant H as

H=

1 a

(5)

The experimental isothermal solubility data were fitted with eq 4 using nonlinear least-squares method. For each isothermal solubility curve, three parameters of a, b, and xe were optimized. The results are listed in Table 5 along with the average absolute relative deviations (AARD) of the correlation. It is shown that

Table 2. Solubility of HCl in [Bmim]Cl at Different Temperatures and Varying Pressuresa T = 298.15 K

a

T = 323.15 K

T = 348.15 K

T = 363.15 K

P/kPa

xHCl

P/kPa

xHCl

P/kPa

xHCl

P/kPa

xHCl

3.44 4.56 6.13 9.44 15.53 23.65 33.21 46.00 61.33 74.93 88.92 100.28

0.346 0.403 0.459 0.515 0.556 0.590 0.617 0.638 0.656 0.670 0.680 0.687

2.67 3.41 4.32 6.19 10.35 19.57 32.08 45.74 57.41 70.85 86.59 98.28 104.71

0.319 0.372 0.423 0.472 0.514 0.553 0.581 0.598 0.613 0.626 0.639 0.648 0.652

3.60 5.33 7.92 12.25 23.54 44.61 69.65 90.84 99.94

0.271 0.339 0.410 0.467 0.515 0.554 0.591 0.608 0.613

7.00 11.00 20.33 36.20 57.93 74.86 88.71 99.99

0.316 0.399 0.467 0.506 0.534 0.549 0.560 0.567

Uncertainties are: U(P) = 0.13 kPa; U(T) = 0.1 K; U(x) = 0.003. C

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Table 3. Solubility of HCl in [Hmim]Cl at Different Temperatures and Varying Pressuresa T = 298.15 K

a

T = 323.15 K

T = 348.15 K

T = 363.15 K

P/kPa

xHCl

P/kPa

xHCl

P/kPa

xHCl

P/kPa

xHCl

3.33 4.53 5.96 8.35 12.53 18.43 26.74 36.72 49.38 64.93 81.60 96.79 108.32

0.276 0.354 0.419 0.475 0.524 0.562 0.594 0.618 0.638 0.655 0.671 0.681 0.688

0.85 1.52 2.53 4.00 6.29 11.05 19.87 31.18 45.89 64.86 82.13 97.79 111.59

0.129 0.199 0.278 0.365 0.427 0.485 0.530 0.562 0.588 0.609 0.624 0.636 0.644

2.21 3.36 5.20 9.20 18.21 37.05 57.69 77.53 93.32 104.31

0.253 0.327 0.393 0.452 0.497 0.539 0.567 0.586 0.598 0.605

3.47 5.23 8.69 15.36 28.33 46.78 66.93 85.46 102.19

0.249 0.326 0.396 0.449 0.489 0.519 0.541 0.557 0.568

Uncertainties are: U(P) = 0.13 kPa; U(T) = 0.1 K; U(x) = 0.003.

Table 4. Solubility of HCl in [Omim]Cl at Different Temperatures and Varying Pressuresa T = 298.15 K

a

T = 323.15 K

T = 348.15 K

T = 363.15 K

P/kPa

xHCl

P/kPa

xHCl

P/kPa

xHCl

P/kPa

xHCl

2.13 3.11 4.37 6.93 12.17 18.85 28.08 40.17 54.13 67.99 81.19 93.28 104.59

0.266 0.355 0.417 0.475 0.529 0.565 0.595 0.620 0.640 0.654 0.665 0.674 0.680

2.29 3.49 5.47 10.00 17.89 29.30 42.88 65.57 80.25 92.23 104.00

0.250 0.332 0.408 0.469 0.515 0.552 0.580 0.599 0.611 0.621 0.629

4.69 7.73 13.47 24.24 38.85 53.56 67.00 81.76 93.06 101.64

0.330 0.391 0.445 0.490 0.524 0.546 0.566 0.579 0.590 0.596

6.51 10.09 15.92 27.02 44.89 61.70 77.73 93.99 105.87

0.254 0.337 0.410 0.463 0.504 0.529 0.546 0.561 0.569

Uncertainties are: U(P) = 0.13 kPa; U(T) = 0.1 K; U(x) = 0.003.

Figure 3. Solubility of HCl in [Bmim]Cl at varying pressure and different temperatures: ■, 298.15 K; □, 323.15 K; ▲, 348.15 K; △, 363.15 K.

Figure 4. Comparison of solubility of HCl in different ILs in molHCl/g-solvent at 323.15 K: ○, [Bmim]Cl; ■, [Hmim]Cl; △, [Omim]Cl; ▲, solubility of HCl in water at 273.15 K.

the solubility data of HCl in the imidazolium ILs ([BMIM]Cl, [HMIM]Cl, and [OMIM]Cl) in a wide pressure and

temperature range can be well-correlated by the proposed model. As an example, Figure 5 shows the apparent total solubility of HCl in [Bmim]Cl and the respective contributions from the D

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Table 5. Regressed Model Parameters and Deviation in AARD% for the Solubility Data and the Calculated Henry’s Constant Ha T/K

a·106/Pa−1

b·10−3/Pa

298.15 323.15 348.15 363.15

0.52 0.42 0.39 0.35

3.00 2.30 3.90 4.41

298.15 323.15 348.15 363.15

0.49 0.39 0.35 0.31

3.36 3.04 2.98 4.13

298.15 323.15 348.15 363.15

0.46 0.33 0.31 0.28

2.71 3.09 4.03 7.02

xe [Bmim]Cl 0.66 0.62 0.60 0.57 [Hmim]Cl 0.65 0.61 0.59 0.56 [Omim]Cl 0.64 0.6 0.58 0.55

H·10−6/Pa

AARD%

1.92 2.38 2.56 2.86

1.29 1.57 1.71 1.27

2.04 2.56 2.86 3.35

1.96 1.59 1.96 1.71

2.17 2.86 3.23 3.57

1.70 1.49 1.85 0.62

Figure 6. Henry’s constants of HCl in three ILs versus temperature: ■, [Bmim]Cl; □, [Hmim]Cl; ▲, [Omim]Cl.

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CONCLUSIONS The solubility of HCl in ILs [Bmim]Cl, [Hmim]Cl, and [Omim]Cl was determined at temperatures of (298.15, 323.15, 348.15, and 363.15) K and pressure ranging from (0 to 100) kPa. The solubility of HCl in these ILs is very high, and the gas solubility decreases with the increase of the alkyl length of the ILs. The dissolution of HCl in these ILs might consist of both chemical and physical part, and the experimental solubility data can be well-correlated with an empirical model which accounts for these two contributions separately. Considering their nonvolatility, high solubility for HCl, and easiness for recycling use, ILs might be used as alternative solvents for the absorption of HCl in practice.

AARD% = (100/n)∑ni=1|xcal/xexp − 1.0|, n is the number of data points.

a

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ASSOCIATED CONTENT

S Supporting Information *

NMR analysis of the ILs. This material is available free of charge via the Internet at http://pubs.acs.org.

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Figure 5. Scheme of the solubility of HCl in [Bmim]Cl at 298.15 K and their contributions: (1) apparent solubility; (2) Henry’s law type physical absorption contribution; (3) Langmuir type chemical absorption contribution.

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Tel./fax: +86 10 64410308. Funding

The authors are grateful for the financial support from National Natural Science Foundation of China (21076005) and Research Fund for the Doctoral Program of Higher Education of China (20090010110001).

chemical reactive dissolution and the physical dissolution at 298.15 K. It is clear that the chemical reactive dissolution takes an overwhelming advantage especially at low pressure. When pressure exceeds 20 kPa, the impact of the physical dissolution increases significantly, and the chemical reactive dissolution is limited by saturation showing a pressure-independent solubility trend. The Langmuir saturated solubilities of the three ILs, as shown in Table 5, are almost the same indicating that the cation’s alkyl on the imidazolium ring does not affect the chemical interactions among the ions and the ILs. On the other hand, the Langmuir saturated solubility is seen to be inversely proportional to temperature. A comparison of the Henry’s law constant at several temperatures (298.15, 323.15, 348.15, and 363.15) K is shown in Figure 6. For each ionic liquid, Henry’s law constant is observed to increase with the rising of temperature and the increasing alkyl length of the cations, indicating that temperature and the geometry of the ILs have a significant effect on the physical absorption of HCl.

Notes

The authors declare no competing financial interest.

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