Phase Equilibria of Double Semiclathrate Hydrates Formed with

Article pubs.acs.org/jced

Phase Equilibria of Double Semiclathrate Hydrates Formed with Tetraamylammonium Bromide Plus CH4, CO2, or N2 Published as part of The Journal of Chemical and Engineering Data special issue “Proceedings of the 19th Symposium on Thermophysical Properties” Lingli Shi†,‡ and Deqing Liang*,† †

Key Laboratory of Gas Hydrate, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China ‡ University of Chinese Academy of Sciences, Beijing 100049, China ABSTRACT: Dissociation data for the semiclathrate hydrates formed with tetraamylammonium bromide (TAAB: C20H44NBr) + CH4, + CO2, or + N2 were measured in the pressure range of (1.33 to 20.37) MPa and temperature range of (279.8 to 291.9) K at (0.050 and 0.100) mass fraction of TAAB. The experimental data were obtained by employing an isochoric pressure-search method. The results showed that at a given pressure, the temperature required to form double TAAB + CH4, + CO2, or + N2 hydrates was higher than that required for the corresponding pure CH4, CO2, or N2 hydrates, and as the TAAB concentration increased, its effect of enlarging the hydrate stability zone was strengthened. However, the experimental dissociation temperatures for double semiclathrate hydrates were lower than those for TAAB hydrates formed without guest gases. In addition, the data for double semiclathrate hydrates formed from TAAB generated in this work were compared with those formed from some other semiclathrate hydrate formers (such as tetrabutylammonium bromide, tetrabutylammonium chloride, and tetrabutylammonium fluoride) reported in literature. SCH, halide anions such as Br− and Cl− together with water molecules, by means of hydrogen bonding, construct the host framework of the cavities, in which the cations (TBA+) are included as the guest.59−62 In other words, SCH formers can both form part of the host framework and occupy cages after breaking part of the cage structure. The small dodecahedral (512) cages are left vacant, which can capture gas molecules of suitable size under moderate conditions.37,63−66 And this kind of SCH formed with guest gas is named as double SCH, for example, TBAB + CH4 double SCH. Therefore, SCH has been considered as a new material for gas storage and separation. Table 1 presents a concise review of some studied SCH systems of SCH former solutions at different concentrations including CH4, CO2, and N2 available in open literature. All SCH formers have stabilized gas hydrates, and the strong-toweak order of their stabilization effects is the same as the highto-low order of their melting temperatures under atmospheric pressure, which is TBAF, TBAC, and TBAB. According to the data reported by Aladko,67 tetraamylammonium bromide (TAAB: C20H44NBr) showed more enhanced thermal stability than TBAF when SCH is formed with water. The melting point of TAAB·38H2O hydrate is 301.45 K, which is higher than

1. INTRODUCTION Clathrate hydrates are one kind of nonstoichiometric crystalline inclusion compounds. They are composed of a lattice of hydrogen-bonded water molecules which traps guest molecules of gases (such as CH4, CO2, or N2) or some volatile liquids (such as tetrahydrofuran, acetone) within polyhedral cavities under appropriate conditions of low temperature and high pressure.1 Clathrate hydrates are found to be stabilized by van der Waals forces between guest molecules and host water molecules. And they have been recognized as an innovative medium for many positive applications, such as gas storage,2,3 gas separation,4,5 energy storage,6−8 water desalination,9 separation of close-boiling point compounds10−13 and so forth. However, the high equilibrium pressures required for the hydrate formation are the primary drawback in the application of these hydrate-based technologies. Extensive experimental investigations on thermodynamic promoters have been made to enlarge hydrates’ thermal stability regions. A group of additives, known as semiclathrate hydrate (SCH) formers, such as tetrabutylammonium bromide (TBAB),14−46 tetrabutylammonium chloride (TBAC),30,42,47−56 and tetrabutylammonium fluoride (TBAF),30,42,46,49,57,58 have been intensively studied within the past few years, because of their ability of allowing hydrate to form at favorable conditions. Actually, SCHs share many of physical and structural properties of ordinary clathrate hydrates. The primary difference is that, in © 2015 American Chemical Society

Received: June 19, 2015 Accepted: July 30, 2015 Published: August 10, 2015 2749

DOI: 10.1021/acs.jced.5b00516 J. Chem. Eng. Data 2015, 60, 2749−2755

Journal of Chemical & Engineering Data

Article

Table 1. Experimental Data in the Open Literature for SCHs Formed with SCH Formers and Various Guest Gases at Different Concentrations SCH former

guest gas

salt mass fraction

T/K range

p/MPa range

number of data

ref

TBAB

CH4 CO2 N2 CH4 CO2 N2 CH4 CO2 N2

0.05 to 0.60 0.0443 to 0.65 0.05 to 0.60 0.05 to 0.45 0.043 to 0.50 0.05 to 0.44 0.02 to 0.45 0.02 to 0.45 0.05 to 0.45

279.72 to 298.15 279.06 to 291.8 280.95 to 294.5 281.3 to 295.2 279.42 to 293.33 278.8 to 292.4 285.1 to 304.7 285.1 to 302.3 290.5 to 303.4

0.235 to 41.369 0.104 to 4.56 0.47 to 25 0.61 to 10.56 0.36 to 4.61 0.61 to 13.57 1.05 to 9.62 0.53 to 4.98 2.05 to 0.24

213 181 74 90 144 53 37 50 28

31 to 39 31, 32, 36, 37, 40 to 45 32, 36, 39, 40, 43, 46 47 to 51 42, 47, 50 to 55 47, 50, 53 57, 58 42, 49, 57, 58 46, 58

TBAC

TBAF

Figure 1. (a) Schematic diagram of the experimental apparatus: DPT, differential pressure transducer; RTD, resistance temperature detector; GC, gas chromatography; V1 to V9, valves. (b) Picture of sapphire variable-volume cell.

ranged from (279.8 to 291.9) K and from (1.33 to 20.37) MPa, respectively.

those of TBAB·38H2O hydrate (285.8 K), TBAC·30H2O hydrate (288.19 K), and TBAF·28.6H2O (300.75 K) hydrate by 15.65 K, 13.26 K, and 0.70 K, respectively. Thus, TAAB is expected to have a better promotion effect on hydrate formation for technological applications. It should be noted that only a few attempts have been made to study the phase equilibrium conditions of TAAB double SCH. Wang et al.68 showed the stability of TAAB + CH4 SCH through the DSC instrument. Majumdar et al.69 measured phase equilibrium conditions of TAAB double SCH formed with pure CO2, pure N2, and (CO2 + N2) mixtures. To our best knowledge, equilibrium data of double TAAB + gas SCH at lower TAAB concentrations are entirely absent. This literature review indicates an imperative need to thoroughly examine TAAB as a SCH former and generate more phase equilibrium data of TAAB + gas double hydrate to design efficient industrial processes, because the investigation on TAAB is still scarce. Therefore, in this work, to provide the stability conditions of the double TAAB SCH, we measured the three-phase equilibria for ternary systems of TAAB + CH4 + H2O, TAAB + CO2 + H2O, and TAAB + N2 + H2O at w = (0.050, and 0.100), where w denotes the mass fraction of TAAB in aqueous solutions. The experiment was conducted by employing an isochoric pressuresearch method, and the experimental temperature and pressure

2. EXPERIMENTAL SECTION 2.1. Experimental Materials. The pure CH4, CO2, and N2 gases used for the present study were supplied by Guangzhou Shiyuan Gases Co. with stated purities of 0.999, 0.99999, and 0.9999, respectively. TAAB with a purity of 0.98 (mass fraction) was purchased from Tokyo Chemical Industry Co. Deionized water made in the laboratory was used to dilute TAAB to the desired TAAB aqueous solution in the experiments. All materials were used without further purification. 2.2. Experimental Apparatus and Procedure. The experimental apparatus for phase equilibria of TAAB + gas double SCH, same as the one in a previous work,53,70−72 was made by Sanchez Technologies Company for accurate measurement of hydrate dissociation temperatures and pressures. The main part of the apparatus is a “full view” sapphire variable-volume cell that can withstand temperatures ranging from (253 to 399) K and pressures up to 40 MPa. A stirrer is installed in the vessel to agitate the test fluid and hydrate crystals. The stirrer was driven both by a DC motor located at the end of the moveable piston and a magnetic coupling mounted outside the cell. The temperature and 2750



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pressure are measured by means of a platinum resistance thermometer (Pt100) and a TF01 400A absolute pressure transducer, whose maximum uncertainties are ± 0.1 K and ± 0.024 MPa, respectively. All of the experimental data are collected through a data acquisition system and saved at 10 s intervals on a computer. A detailed schematic figure of the experimental apparatus and the picture of sapphire cell were shown in Figure 1. The TAAB double SCH dissociation conditions were measured by employing an isochoric pressure search method. At first, the cell was washed with deionized water and the test fluid thrice, respectively. Then the cell was evacuated with the vacuum pump and injected with approximately 20 mL of TAAB aqueous solution. A certain amount of gas (CH4, N2, or CO2) was introduced to the desired pressure. Subsequently, the cell was cooled to form hydrates, which could be detected by a rapid drop in pressure and direct observation. After the solid phases reached equilibrium, the cell was then heated gradually in steps of 0.1 K, and each temperature step was maintained for sufficient time (at least 4 h) to achieve an equilibrium state in the cell. During the experiment, both the temperature and pressure were recorded and plotted. In this way, a pressure− temperature diagram was obtained for each experimental run, from which the hydrate dissociation point was determined by the sharp change of the curve. By adjusting the cell’s volume and the system’s temperature, equilibrium conditions of system with different pressures were determined. Eventually, by repeating the procedure, the equilibrium conditions of TAAB + gas double SCH with different salt mass fractions and guest gases were obtained with uncertainties of temperatures and pressures being ± 0.1 K and ± 0.024 MPa, respectively.

Figure 2. Experimental equilibrium data of TAAB + CH4 double SCHs: ■, pure CH4 hydrate, ref 73 and 74; +, w = 0.050, this work; □, w = 0.100, this work.

3. RESULTS AND DISCUSSION The hydrate dissociation data for TAAB + CH4/CO2/N2 + H2O systems were measured to determine the stability conditions of TAAB + CH4, TAAB + CO2, and TAAB + N2 double SCHs in the presence of TAAB aqueous solutions at w = (0.050, and 0.100). The experimental results are summarized Table 2. Phase Equilibrium Data of SCHs Formed with TAAB Aqueous Solution + CH4, + CO2, or + N2 at Two Different Mass Fractions (w) of TAAB.a system

T/K

p/MPa

System

T/K

p/MPa

TAAB (w = 0.050) + CH4

283.9 285.8 287.3 288.4 289.4 279.8 281.1 281.5 282.3 283.1 283.2

5.61 7.52 9.47 11.55 13.33 1.95 2.41 2.69 3.22 3.89 4.08

TAAB (w = 0.100) + CH4

280.6 281.4 282.5 283.3 284.2

12.25 14.24 16.10 18.14 20.31

TAAB (w = 0.100) + N2

286.6 288.4 289.8 290.9 291.9 280.0 280.8 281.9 283.2 283.7 284.4 284.8 282.7 283.8 284.6 285.4 286.3

5.78 7.73 9.88 11.90 13.98 1.33 1.63 2.00 2.67 3.00 3.53 3.89 12.20 14.17 16.21 18.10 20.37

TAAB (w = 0.050) + CO2

TAAB (w = 0.050) + N2

TAAB (w = 0.100) + CO2

Figure 3. Experimental equilibrium data of TAAB + CO2 double SCHs. ●, pure CO2 hydrate, ref 74 to 76; +, w = 0.050, this work; ○, w = 0.100, this work; ∗, w = 0.1403, ref 69.

in Table 2 and plotted in Figures 2 to 4 with those for pure CH4,73,74 CO2,74−76 and N277−79 hydrates and TAAB + CO2/ N2 double SCHs69 from open literature. As shown in Figure 1, TAAB has a stabilization effect on CH4 hydrate. It shifted the dissociation conditions of CH4 hydrate to the stabilized regions represented by higher temperatures and lower pressures when compared with pure CH4 hydrates. A higher stabilization effect was observed for systems with w = 0.100, which meant that with the salt concentration increased the promotion effect was also strengthened. In addition, the increase of temperature at the same pressure was different for systems with different guest gases. For example, with the addition of TAAB whose mass fraction is 0.050, the equilibrium temperature for CH4 hydrate was increased by 3.4 K at 5.61 MPa. For N2 and CO2 hydrates, the temperatures were increased by about 9.4 K at 14.24 MPa and 3.0 K at 1.95 MPa, respectively. However, when compared with those from ref 69, our obtained data showed that the stabilization effect of TAAB

Uncertainties u are u(w) = ± 0.002, u(T) = ± 0.1 K, u(p) = ± 0.024 MPa. a

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Figure 4. Experimental equilibrium data of TAAB + N2 double SCHs. ▲, pure N2 hydrate, ref 77 to 79; +, w = 0.050, this work; △, w = 0.100, this work; ∗, w = 0.1403, ref 69.

Figure 6. Experimental equilibrium data for double SCH formed with CO2 and various SCH formers at different mass fractions. ⧫, pure CO2 hydrate, ref 74 to 76. (a) w = 0.050: □, TAAB, this work; ○, TBAB, ref 36; △, TBAC, ref 50, 54, and 55; ▽, TBAF, ref 49 and 58,. (b) w = 0.100: ■, TAAB, this work; ●, TBAB, ref 32 and 36; ▲, TBAC, ref 54 and 55; ▼, TBAF, ref 49 and 57.

Figure 5. Experimental equilibrium data for double SCH formed with CH4 and various SCH formers at different mass fractions. ⧫, pure CH4 hydrate, ref 73 and 74. (a) w = 0.050: □, TAAB, this work; ○, TBAB, ref 32, 33 and 35; △, TBAC, ref 48 to 50; ▽, TBAF, ref 58. (b) w = 0.100: ■, TAAB, this work; ●, TBAB, ref 32, 33, and 36; ▲, TBAC, ref 48 and 49; ▼, TBAF, ref 57.

Figure 7. Experimental equilibrium data for double SCH formed with N2 and various SCH formers. ⧫, pure N2 hydrate, ref 77 to 79; □, TAAB (w = 0.050), this work; ■, TAAB (w = 0.100), this work; ○, TBAB (w = 0.050), ref 36 and 46; ●, TBAB (w = 0.100), ref 32 and 36; △, TBAC (w = 0.050), ref 50; ▽, TBAF (w = 0.050), ref 58; ▼, TBAF (w = 0.100), ref 46.

is remarkably weaker in lower salt concentrations than that in higher ones. This might be caused by two factors: (1) special structure of TAAC hydrates which should be studied with structural analysis equipment in the future study, and (2) different preparation processes for tested aqueous solutions.

For further understanding, in Figures 5 to 7, our obtained data were compared with those for TBAB/TBAC/TBAF + 2752



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(7) Li, G.; Liu, D.; Xie, Y. Study on thermal properties of TBAB-THF hydrate mixture for cold storage by DSC. J. Therm. Anal. Calorim. 2010, 102, 819−826. (8) Wang, X.; Dennis, M.; Hou, L. Clathrate hydrate technology for cold storage in air conditioning systems. Renewable Sustainable Energy Rev. 2014, 36, 34−51. (9) Ngema, P. T.; Petticrew, C.; Naidoo, P.; Mohammadi, A. H.; Ramjugernath, D. Experimental measurements and thermodynamic modeling of the dissociation conditions of clathrate hydrates for (refrigerant plus NaCl plus water) systems. J. Chem. Eng. Data 2014, 59, 466−475. (10) Tumba, K.; Naidoo, P.; Mohammadi, A. H.; Richon, D.; Ramjugernath, D. Phase equilibria of clathrate hydrates of ethane plus ethane. J. Chem. Eng. Data 2013, 58, 896−901. (11) Tumba, K.; Hashemi, H.; Naidoo, P.; Mohammadi, A. H.; Ramjugernath, D. Dissociation data and thermodynamic modeling of clathrate hydrates of ethane, ethyne, and propene. J. Chem. Eng. Data 2013, 58, 3259−3264. (12) Tumba, K.; Babaee, S.; Naidoo, P.; Mohammadi, A. H.; Ramjugernath, D. Phase equilibria of clathrate hydrates of ethyne plus propane. J. Chem. Eng. Data 2014, 59, 2914−2919. (13) Tumba, K.; Hashemi, H.; Naidoo, P.; Mohammadi, A. H.; Ramjugernath, D. Phase equilibria of clathrate hydrates of ethyne + propene. J. Chem. Eng. Data 2015, 60, 217−221. (14) Babu, P.; Chin, W. I.; Kumar, R.; Linger, P. Systematic evaluation of tetra-n-butyl ammonium bromide (TBAB) for carbon dioxide capture employing the clathrate process. Ind. Eng. Chem. Res. 2014, 53, 4878−4887. (15) Belandria, V.; Mohammadi, A. H.; Eslamimanesh, A.; Richon, D.; Sanchez-Mora, M. F.; Galicia-Luna, L. A. Phase equilibrium measurements for semi-clathrate hydrates of the (CO2 + N2 + tetra-nbutylammonium bromide) aqueous solution systems: Part 2. Fluid Phase Equilib. 2012, 322−323, 105−112. (16) Belandria, V.; Mohammadi, A. H.; Richon, D. Compositional analysis of the gas phase for the CO2 + N2 + Tetra-n-butylammonium bromide aqueous solution systems under hydrate stability conditions. Chem. Eng. Sci. 2012, 84, 40−47. (17) Gholinezhad, J.; Chapoy, A.; Tohidi, B. Separation and capture of carbon dioxide from CO2/H2 syngas mixture using semi-clathrate hydrates. Chem. Eng. Res. Des. 2011, 89, 1747−1751. (18) Kim, S. M.; Lee, J. D.; Lee, H. J.; Lee, E. K.; Kim, Y. Gas hydrate formation method to capture the carbon dioxide for pre-combustion process in IGCC plant. Int. J. Hydrogen Energy 2011, 36, 1115−1121. (19) Li, S.; Fan, S.; Wang, J.; Lang, X.; Liang, D. CO2 capture from binary mixture via forming hydrate with the help of tetra-n-butyl ammonium bromide. J. Nat. Gas Chem. 2009, 18, 15−20. (20) Li, X. S.; Xia, Z. M.; Chen, Z. Y.; Yan, K. F.; Li, G.; Wu, H. Equilibrium hydrate formation conditions for the mixtures of CO2 + H2 + tetrabutyl ammonium bromide. J. Chem. Eng. Data 2010, 55, 2180−2184. (21) Li, X. S.; Xia, Z. M.; Chen, Z. Y.; Yan, K. F.; Li, G.; Wu, H. Gas hydrate formation process for capture of carbon dioxide from fuel gas mixture. Ind. Eng. Chem. Res. 2010, 49, 11614−11619. (22) Li, X. S.; Xu, C. G.; Chen, Z. Y.; Wu, H. Tetra-n-butyl ammonium bromide semiclathrate hydrate process for postcombustion capture of carbon dioxide in the presence of dodecyl trimethyl ammonium chloride. Energy 2010, 35, 3902−3908. (23) Li, X. S.; Xia, Z. M.; Chen, Z. Y.; Wu, H. Precombustion capture of carbon dioxide and hydrogen with a one-stage hydrate/membrane process in the presence of tetra-n-butylammonium bromide (TBAB). Energy Fuels 2011, 25, 1302−1309. (24) Li, X. S.; Xu, C. G.; Chen, Z. Y.; Cai, J. Synergic effect of cyclopentane and tetra-nbutyl ammonium bromide on hydrate-based carbon dioxide separation from fuel gas mixture by measurements of gas uptake and X-ray diffraction patterns. Int. J. Hydrogen Energy 2012, 37, 720−727. (25) Li, X. S.; Zhan, H.; Xu, C. G.; Zeng, Z. Y.; Lv, Q. N.; Yan, K. F. Effects of tetrabutyl-(ammonium/phosphonium) salts on clathrate

CH4/CO2/N2 + H2O systems at the same salt concentrations. As shown, all SCH formers have stabilized gas hydrates with different degrees. The comparison showed that the stabilization effect of TAAB was the weakest. And the weak-to-strong order was TAAB, TBAC, TBAB, and TBAF. For tetrabutylammonioum halides, the order is the same as the low-to-high order of melting temperatures under atmospheric pressure for systems at w = (0.050, and 0.010). For TAAB, the stabilization effect was different in lower salt concentrations. We supposed that this result might be caused by four factors: (1) the decrease of the activity of TAAB in the liquid phase, (2) weakness of the van der Waals forces between the host and the guest, (3) structural distortion of host framework caused by guest molecules, and (4) partial filling of the vacant cages in the host lattice with “guest” water molecules. This explanation still needs more structural analysis in future study. Nevertheless, TAAB has the ability of stabilizing hydrates of CH4, CO2, and N2. The data generated in this study could be beneficial for gas separation and storage based on SCH hydrates.

4. CONCLUSIONS In this work, phase equilibrium conditions of TAAB + CH4, + CO2, and + N2 double SCHs were determined at w = (0.050, and 0.100). The experiment was carried out by measurements with ensured reliability in the temperature range of (279.8 to 291.9) K and pressure range of (1.33 to 20.37) MPa. The measurement technique was based on the isochoric pressuresearch method. The results showed that TAAB had stabilization effects on CH4, CO2, and N2 hydrates, and with the salt concentration increased, the stabilization effect was also strengthened. This effect could lead to a more efficient process for gas separation and storage using SCHs compared with processes using ordinary clathrate hydrates.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Tel.: +86 20 8705 7669. Fax: +86 20 8705 7669. Funding

This work was supported by the National Natural Science Foundation of China (51376182), CAS Program (KGZD-EW301), and 863 Program (2012AA061403-03). Notes

The authors declare no competing financial interest.

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Phase Equilibria of Double Semiclathrate Hydrates Formed with

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