Semi-clathrate hydrate based carbon dioxide capture and separation techniques

Lijuan Gu , Hailong Lu

Front. Environ. Sci. Eng. ›› 2023, Vol. 17 ›› Issue (12) : 144

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Front. Environ. Sci. Eng. ›› 2023, Vol. 17 ›› Issue (12) : 144 DOI: 10.1007/s11783-023-1744-7
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Semi-clathrate hydrate based carbon dioxide capture and separation techniques

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Abstract

● Structural and thermodynamical properties of semi-clathrate hydrate are summarized.

● Properties of quaternary salts and gas mixture hydrate are summarized.

● Challenges persist in the application of semi-clathrate hydrates for carbon capture and separation.

CO2 is considered as the main contributor to global warming, and hydrate enclathration is an efficient way for carbon capture and separation (CCS). Semi-clathrate hydrate (SCH) is a type of clathrate hydrate capable of encaging CO2 molecules under mild temperature and pressure conditions. SCH has numerous unique advantages, including high thermal stability, selective absorption of gas molecules with proper size and recyclable, making it a promising candidate for CCS. While SCH based CCS technology is in the developing stage and great efforts have to be conducted to improve the performance that is determined by their thermodynamical and structural properties. This review summarizes and compares the thermodynamic and structural properties of SCH and quaternary salt hydrates with gas mixtures to be captured and separated. Based on the description of the physical properties of SCH and hydrate of quaternary salts with gas mixture, the CO2 capture and separation from fuel gas, flue gas and biogas with SCH are reviewed. The review focuses on the use of tetra-n-butyl ammonium halide and tetra-n-butyl phosphonium halide, which are the current application hotspots. This review aims to provide guidance for the future applications of SCH.

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Keywords

Semi-clathrate hydrate / Tetra- n-butyl ammonium halide / Tetra- n-butyl phosphonium halide / Structure / Thermodynamical properties / CO 2 capture and separation

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Lijuan Gu, Hailong Lu. Semi-clathrate hydrate based carbon dioxide capture and separation techniques. Front. Environ. Sci. Eng., 2023, 17(12): 144 DOI:10.1007/s11783-023-1744-7

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References

[1]

Acosta H Y, Bishnoi P R, Clarke M A. (2011). Experimental measurements of the thermodynamic equilibrium conditions of tetra-n-butylammonium bromide semiclathrates formed from synthetic landfill gases. Journal of Chemical & Engineering Data, 56(1): 69–73

[2]

Adisasmito S, Frank R J III, Sloan E D Jr. (1991). Hydrates of carbon dioxide and methane mixtures. Journal of Chemical & Engineering Data, 36(1): 68–71

[3]

Aladko L S, Dyadin Y A. (1996). Clathrate formation in the Bu4NClNH4ClH2O system. Mendeleev Communications, 6(5): 198–200

[4]

AladkoL SDyadin Y ARodionovaT VTerekhovaI S (2003). Effect of size and shape of cations and anions on clathrate formation in the system: halogenides of quaterly ammonium bases and water. Journal of Molecular Liquids, 106(2−3): 229−238

[5]

Arjmandi M, Chapoy A, Tohidi B. (2007). Equilibrium data of hydrogen, methane, nitrogen, carbon dioxide, and natural gas in semi-clathrate hydrates of tetrabutyl ammonium bromide. Journal of Chemical & Engineering Data, 52(6): 2153–2158

[6]

Babu P, Chin W I, Kumar R, Linga P. (2014a). Systematic evaluation of tetra-n-butylammonium bromide (TBAB) for carbon dioxide capture employing the clathrate process. Industrial & Engineering Chemistry Research, 53(12): 4878–4887

[7]

Babu P, Datta S, Kumar R, Linga P. (2014b). Impact of experimental pressure and temperature on semiclathrate hydrate formation for pre-combustion capture of CO2 using tetra-n-butyl ammonium nitrate. Energy, 78: 458–464

[8]

Babu P, Linga P, Kumar R, Englezos P. (2015). A review of the hydrate based gas separation (HBGS) process for carbon dioxide pre-combustion capture. Energy, 85: 261–279

[9]

Babu P, Yao M, Datta S, Kumar R, Linga P. (2014c). Thermodynamic and kinetic verification of tetra-n-butylammonium nitrate (TBANO3) as a promoter for the clathrate process applicable to precombustion carbon dioxide capture. Environmental Science & Technology, 48(6): 3550–3558

[10]

BelandriaVMohammadi A HEslamimaneshARichonDSánchez-Mora M FGalicia-LunaL A (2012). Phase equilibrium measurements for semi-clathrate hydrates of the (CO2+N2+tetra-n-butylammonium bromide) aqueous solution systems: Part 2. Fluid Phase Equilibria, 322–323: 105–112

[11]

Ben-Mansour R, Habib M A, Bamidele O E, Basha M, Qasem N A A, Peedikakkal A, Laoui T, Ali M. (2016). Carbon capture by physical adsorption: materials, experimental investigations and numerical modeling and simulations: a review. Applied Energy, 161: 225–255

[12]

Castellani B, Rossi F, Filipponi M, Nicolini A. (2014). Hydrate-based removal of carbon dioxide and hydrogen sulphide from biogas mixtures: experimental investigation and energy evaluations. Biomass and Bioenergy, 70: 330–338

[13]

Chapoy A, Anderson R, Tohidi B. (2007). Low-pressure molecular hydrogen storage in semi-clathrate hydrates of quaternary ammonium compounds. Journal of the American Chemical Society, 129(4): 746–747

[14]

Chapoy A, Gholinezhad J, Tohidi B. (2010). Experimental clathrate dissociations for the hydrogen+water and hydrogen+tetrabutylammonium bromide+water systems. Journal of Chemical & Engineering Data, 55(11): 5323–5327

[15]

Chazallon B, Ziskind M, Carpentier Y, Focsa C. (2014). CO2 capture using semi-clathrates of quaternary ammonium salt: structure change induced by CO2 and N2 enclathration. Journal of Physical Chemistry B, 118(47): 13440–13452

[16]

Chen Z, Deng S, Wei H, Wang B, Huang J, Yu G. (2013). Activated carbons and amine-modified materials for carbon dioxide capture: a review. Frontiers of Environmental Science & Engineering., 7(3): 326–340

[17]

Darbouret M, Cournil M, Herri J M. (2005). Rheological study of TBAB hydrate slurries as secondary two-phase refrigerants. International Journal of Refrigeration, 28(5): 663–671

[18]

DavidsonD W (1973). Water: A Comprehensive Treatise. New York: Plenum Press

[19]

Davis S J, Lewis N S, Shaner M, Aggarwal S, Arent D, Azevedo I L, Benson S M, Bradley T, Brouwer J, Chiang Y M. . (2018). Net-zero emissions energy systems. Science, 360(6396): eaas9793

[20]

Deschamps J, Dalmazzone D. (2009). Dissociation enthalpies and phase equilibrium for TBAB semi-clathrate hydrates of N2, CO2, N2+CO2 and CH4+CO2. Journal of Thermal Analysis and Calorimetry, 98(1): 113–118

[21]

Deschamps J, Dalmazzone D. (2010). Hydrogen storage in semiclathrate hydrates of tetrabutyl ammonium chloride and tetrabutyl phosphonium bromide. Journal of Chemical & Engineering Data, 55(9): 3395–3399

[22]

Duc N H, Chauvy F, Herri J M. (2007). CO2 capture by hydrate crystallization: a potential solution for gas emission of steelmaking industry. Energy Conversion and Management, 48(4): 1313–1322

[23]

Dyadin Y A, Terekhova I S, Polyanskaya T M, Aladko L S. (1977). Clathrate hydrates of tetrabutylammonium fluoride and oxalate. Journal of Structural Chemistry, 17(4): 566–571

[24]

Dyadin Y A, Udachin K A. (1984). Clathrate formation in water-peralkylonium salts systems. Journal of Inclusion Phenomena, 2(1): 61–72

[25]

Dyadin Y A, Udachin K A. (1987). Clathrate polyhydrates of peralkylonium salts and their analogs. Journal of Structural Chemistry, 28(3): 394–432

[26]

Fan S, Li Q, Nie J, Lang X, Wen Y, Wang Y. (2013). Semiclathrate hydrate phase equilibrium for CO2/CH4 gas mixtures in the presence of tetrabutylammonium halide (bromide, chloride, or fluoride). Journal of Chemical & Engineering Data, 58(11): 3137–3141

[27]

Fan S, Li S, Wang J, Lang X, Wang Y. (2009). Efficient capture of CO2 from simulated flue gas by formation of TBAB or TBAF semiclathrate hydrates. Energy & Fuels, 23(8): 4202–4208

[28]

Fan S, Long X, Lang X, Wang Y, Chen J. (2016). CO2 capture from CH4/CO2 mixture gas with tetra-n-butylammonium bromide semi-clathrate hydrate through a pressure recovery method. Energy & Fuels, 30(10): 8529–8534

[29]

Favre E. (2022). Membrane separation processes and post-combustion carbon capture: state of the art and prospects. Membranes (Basel), 12(9): 884

[30]

Font-Palma C, Cann D, Udemu C. (2021). Review of cryogenic carbon capture innovations and their potential applications. C, 7(3): 730058

[31]

Friedlingstein P, Jones M W, O’Sullivan M, Andrew R M, Bakker D C E, Hauck J, Le Quéré C, Peters G P, Peters W, Pongratz J. . (2022). Global carbon budget 2021. Earth System Science Data, 14(4): 1917–2005

[32]

Gaponenko L A, Solodovnikov S F, Dyadin Y A, Aladko L S, Polyanskaya T M. (1984). Crystallographic study of tetra-n-butylammonium bromide polyhydrates. Journal of Structural Chemistry, 25(1): 157–159

[33]

Gholinezhad J, Chapoy A, Tohidi B. (2011). Separation and capture of carbon dioxide from CO2/H2 syngas mixture using semi-clathrate hydrates. Chemical Engineering Research & Design, 89(9): 1747–1751

[34]

Nakayama H. (1982). Hydrates of organic compounds. VI. Heats of fusion and of solution of quaternary ammonium halide clathrate hydrates. Bulletin of the Chemical Society of Japan, 55(2): 389–393

[35]

Nakayama H. (1983). Hydrates of organic compounds. VII. The effect of anions on the formation of clathrate hydrates of tetrabutyl ammonium salts. Bulletin of the Chemical Society of Japan, 56(3): 877–880

[36]

NakayamaH (1987). Hydrates of organic compounds. XI. Determination of the melting point and hydration numbers of the clathrate-like hydrate of tetrabutyl ammonium chloride by differential scanning calorimetry. Bulletin of the Chemical Society of Japan, 60(3): 839−843

[37]

Hashimoto H, Ozeki H, Yamamoto Y, Muromachi S. (2020). CO2 capture from flue gas based on tetra-n-butylammonium fluoride hydrates at near ambient temperature. ACS Omega, 5(13): 7115–7123

[38]

Hashimoto H, Yamaguchi T, Kinoshita T, Muromachi S. (2017a). Gas separation of flue gas by tetra-n-butylammonium bromide hydrates under moderate pressure conditions. Energy, 129: 292–298

[39]

Hashimoto H, Yamaguchi T, Ozeki H, Muromachi S. (2017b). Structure-driven CO2 selectivity and gas capacity of ionic clathrate hydrates. Scientific Reports, 7(1): 17216

[40]

Hashimoto S, Murayama S, Sugahara T, Sato H, Ohgaki K. (2006). Thermodynamic and Raman spectroscopic studies on H2+tetrahydrofuran+water and H2+tetra-n-butyl ammonium bromide+water mixtures containing gas hydrates. Chemical Engineering Science, 61(24): 7884–7888

[41]

Hashimoto S, Sugahara T, Moritoki M, Sato H, Ohgaki K. (2008). Thermodynamic stability of hydrogen + tetra-n-butyl ammonium bromide mixed gas hydrate in nonstoichiometric aqueous solutions. Chemical Engineering Science, 63(4): 1092–1097

[42]

Herri J M, Bouchemoua A, Kwaterski M, Brântuas P, Galfré A, Bouillot B, Douzet J, Ouabbas Y, Cameirao A. (2014). Enhanced selectivity of the separation of CO2 from N2 during crystallization of semi-clathrates from quaternary ammonium solutions. Oil & Gas Science and Technology, 69(5): 947–968

[43]

Höhne G W H, Cammenga H K, Eysel W, Gmelin E, Hemminger W. (1990). The temperature calibration of scanning calorimeters. Thermochimica Acta, 160(1): 1–12

[44]

Horii S, Ohmura R. (2018). Continuous separation of CO2 from a H2+CO2 gas mixture using clathrate hydrate. Applied Energy, 225: 78–84

[45]

Iarikov D D, Hacarlioglu P, Oyama S T. (2011). Supported room temperature ionic liquid membranes for CO2/CH4 separation. Chemical Engineering Journal, 166(1): 401–406

[46]

Iino K, Sakakibara Y, Suginaka T, Ohmura R. (2014). Phase equilibria for the ionic semiclathrate hydrate formed with tetrabutyl phosphonium chloride plus CO2, CH4, or N2. Journal of Chemical Thermodynamics, 71: 133–136

[47]

Mohammadi A, Pakzad M, Mohammadi A H, Jahangiri A. (2018). Kinetics of (TBAF+CO2) semi-clathrate hydrate formation in the presence and absence of SDS. Petroleum Science, 15(2): 375–384

[48]

Jeffrey G A, McMullan R K. (1967). The clathrate hydrates. Progress in Inorganic Chemistry, 8: 43–108

[49]

Jin Y, Kida M, Nagao J. (2019). Crystal phase conditions of semiclathrate hydrates in nitrogen–tetra-n-butylammonium bromide–water systems below 1 MPa. Journal of Chemical & Engineering Data, 64(6): 2843–2848

[50]

Joshi A, Sangwai J S, Das K, Sami N A. (2013). Experimental investigations on the phase equilibrium of semiclathrate hydrates of carbon dioxide in TBAB with small amount of surfactant. International Journal of Energy and Environmental Engineering, 4(1): 11

[51]

Kamata Y, Yamakoshi Y, Ebinuma T, Oyama H, Shimada W, Narita H. (2005). Hydrogen sulfide separation using tetra-n-butyl ammonium bromide semi-clathrate (TBAB). Energy Fuels, 19(4): 1717–1722

[52]

KárászováM ZachBPetrusová ZČervenkaVBobákMŠyc MIzákP (2020). Post-combustion carbon capture by membrane separation. Separation and Purification Technology, 238: 116448 (Review)

[53]

Kharrat M, Dalmazzone D. (2003). Experimental determination of stability conditions of methane hydrate in aqueous calcium chloride solutions using high pressure differential scanning calorimetry. Journal of Chemical Thermodynamics, 35(9): 1489–1505

[54]

Kida M, Jin Y, Nagao J. (2019). Changes in the 13C NMR spectra of tetra-n-butylammonium chloride by clathrate hydration. Chemical Physics, 522: 233–237

[55]

Kim H, Zheng J, Yin Z, Babu P, Kumar S, Tee J, Linga P. (2023). Semi-clathrate hydrate slurry as a cold energy storage and transport medium: rheological study, energy analysis and enhancement by amino acid. Energy, 264: 126226

[56]

Kim H, Zheng J, Yin Z, Kumar S, Tee J, Seo Y, Linga P. (2022). An electrical resistivity-based method for measuring semi-clathrate hydrate formation kinetics: application for cold storage and transport. Applied Energy, 308: 118397

[57]

Kim S, Ko G, Kim K S, Seo Y. (2020). Phase equilibria of tetra-iso-amylammonium bromide (TiAAB) semiclathrates with CO2, N2, or CO2+N2. Journal of Chemical Thermodynamics, 142: 106024

[58]

Kim S, Seo Y. (2015). Semiclathrate-based CO2 capture from flue gas mixtures: an experimental approach with thermodynamic and Raman spectroscopic analyses. Applied Energy, 154: 987–994

[59]

Kim S M, Lee J D, Lee H J, Lee E K, Kim Y. (2011). Gas hydrate formation method to capture the carbon dioxide for pre-combustion process in IGCC plant. International Journal of Hydrogen Energy, 36(1): 1115–1121

[60]

Klara S M, Srivastava R D. (2002). U.S. DOE integrated collaborative technology development program for CO2 separation and capture. Environment and Progress, 21(4): 247–253

[61]

Kobori T, Muromachi S, Ohmura R. (2015a). Phase equilibrium for ionic semiclathrate hydrates formed in the system of water + tetra-n-butylammonium bromide pressurized with carbon dioxide. Journal of Chemical & Engineering Data, 60(2): 299–303

[62]

Kobori T, Muromachi S, Yamasaki T, Takeya S, Yamamoto Y, Alavi S, Ohmura R. (2015b). Phase behavior and structural characterization of ionic clathrate hydrate formed with tetra-n-butylphosphonium hydroxide: discovery of primitive crystal structure. Crystal Growth & Design, 15(8): 3862–3867

[63]

KomarovV YRodionova T VTerekhovaI SKuratievaN V (2007). The cubic superstructure-I of tetrabutylammonium fluoride (C4H9)4NF·29.7H2O clathrate hydrate. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 59(1-2): 11-15

[64]

Komatsu H, Maruyama K, Yamagiwa K, Tajima H. (2019). Separation processes for carbon dioxide capture with semi-clathrate hydrate slurry based on phase equilibria of CO2+N2+tetra-n-butylammonium bromide+water systems. Chemical Engineering Research & Design, 150: 289–298

[65]

Koyama R, Hotta A, Ohmura R. (2020). Equilibrium temperature and dissociation heat of tetrabutylphosphonium acrylate (TBPAc) ionic semi-clathrate hydrate as a medium for the hydrate-based thermal energy storage system. Journal of Chemical Thermodynamics, 144: 106088

[66]

Lee S, Lee Y, Park S, Kim Y, Lee J D, Seo Y. (2012). Thermodynamic and spectroscopic identification of guest gas enclathration in the double tetra-n-butylammonium fluoride semiclathrates. Journal of Physical Chemistry B, 116(30): 9075–9081

[67]

Lee S, Lee Y, Park S, Seo Y. (2010). Phase Equilibria of semiclathrate hydrate for nitrogen in the presence of tetra-n-butylammonium bromide and fluoride. Journal of Chemical & Engineering Data, 55(12): 5883–5886

[68]

Lee S, Park S, Lee Y, Lee J, Lee H, Seo Y. (2011). Guest gas enclathration in semiclathrates of tetra-n-butylammonium bromide: stability condition and spectroscopic analysis. Langmuir, 27(17): 10597–10603

[69]

Li Q, Fan S, Wang Y, Lang X, Chen J. (2015). CO2 removal from biogas based on hydrate formation with tetra-n-butylammonium bromide solution in the presence of 1-butyl-3-methylimidazolium tetrafluoroborate. Energy & Fuels, 29(5): 3143–3148

[70]

Li S, Fan S, Wang J, Lang X, Liang D. (2009). CO2 capture from binary mixture via forming hydrate with the help of tetra-n-butylammonium bromide. Journal of Natural Gas Chemistry, 18(1): 15–20

[71]

Li S, Fan S, Wang J, Lang X, Wang Y. (2010a). Semiclathrate hydrate phase equilibria for CO2 in the presence of tetra-n-butyl ammonium halide (bromide, chloride, or fluoride). Journal of Chemical & Engineering Data, 55(9): 3212–3215

[72]

Li X S, Xia Z M, Chen Z Y, Wu H J. (2011). 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, 25(3): 1302–1309

[73]

Li X S, Xia Z M, Chen Z Y, Yan K F, Li G, Wu H J. (2010b). Equilibrium hydrate formation conditions for the mixtures of CO2 + H2 + tetrabutyl ammonium bromide. Journal of Chemical & Engineering Data, 55(6): 2180–2184

[74]

Li X S, Xia Z M, Chen Z Y, Yan K F, Li G, Wu H J. (2010c). Gas hydrate formation process for capture of carbon dioxide from fuel gas mixture. Industrial & Engineering Chemistry Research, 49(22): 11614–11619

[75]

Li Z, Zhong D L, Lu Y Y, Yan J, Zou Z L. (2017). Preferential enclathration of CO2 into tetra-n-butylphosphonium bromide semiclathrate hydrate in moderate operating conditions: application for CO2 capture from shale gas. Applied Energy, 199: 370–381

[76]

Li Z, Zhong D L, Zheng W Y, Yan J, Lu Y Y, Yi D T. (2019). Morphology and kinetic investigation of TBAB/TBPB semiclathrate hydrates formed with a CO2+CH4 gas mixture. Journal of Crystal Growth, 511: 79–88

[77]

Lin W, Dalmazzone D, Fürst W, Delahaye A, Fournaison L, Clain P. (2013). Accurate DSC measurement of the phase transition temperature in the TBPB–water system. Journal of Chemical Thermodynamics, 61: 132–137

[78]

LinWDelahayeA FournaisonL (2008). Phase equilibrium and dissociation enthalpy for semi-clathrate hydrate of CO2+TBAB. Fluid Phase Equilibria, 264(1–2): 220–227

[79]

Linga P, Clarke M A. (2017). A review of reactor designs and materials employed for increasing the rate of gas hydrate formation. Energy & Fuels, 31(1): 1–13

[80]

Linga P, Kumar R, Englezos P. (2007a). The clathrate hydrate process for post and pre-combustion capture of carbon dioxide. Journal of Hazardous Materials, 149(3): 625–629

[81]

Linga P, Kumar R, Englezos P. (2007b). Gas hydrate formation from hydrogen/carbon dioxide and nitrogen/carbon dioxide gas mixtures. Chemical Engineering Science, 62(16): 4268–4276

[82]

LipkowskiJKomarov V YRodionovaT VDyadinY AAladkoL S (2002). The structure of tetrabutylammonium bromide hydrate (C4H9)4NBr·21/3H2O. Journal of Supramolecular Chemistry, 2(4–5): 435–439

[83]

Liu F P, Li A R, Qing S L, Luo Z D, Ma Y L. (2022). Formation kinetics, mechanism of CO2 hydrate and its applications. Renewable & Sustainable Energy Reviews, 159: 112221

[84]

Lundgren J O, Olovsson I. (1967). Hydrogen-bond studies. XVI. The crystal structure of chloride trihydrate. Acta Crystallographica, 23(6): 971–976

[85]

Lundgren J O, Olovsson I. (1968). Hydrogen-bond studies. XXX. The crystal structure of hydrogen bromide tetrahydrate, (H7O3)+(H9O4)+2Br·−+H2O. Journal of Chemical Physics, 49(3): 1068–1074

[86]

Ma Z W, Zhang P, Bao H S, Deng S. (2016). Review of fundamental properties of CO2 hydrates and CO2 capture and separation using hydration method. Renewable & Sustainable Energy Reviews, 53: 1273–1302

[87]

MaZ WZhang PWangR ZFuruiSXiG N (2010). Forced flow and convective melting heat transfer of clathrate hydrate slurry in tubes. International Journal of Heat and Mass Transfer, 53(19–20): 3745–3757

[88]

Machida H, Sugahara T, Hirasawa I. (2018). Memory effect in tetra-n-butyl ammonium bromide semiclathrate hydrate reformation: the existence of solution structures after hydrate decomposition. CrystEngComm, 20(24): 3328–3334

[89]

Machida H, Sugahara T, Masunaga H, Hirasawa I. (2020). Calorimetric and small-angle X-ray scattering studies on the memory effect in the tetra-n-butylammonium bromide semiclathrate hydrate system. Journal of Crystal Growth, 533: 125476

[90]

Majumdar A, Maini B, Bishnoi P R, Clarke M A. (2012). Three-phase equilibrium conditions of TiAAB semiclathrates formed from N2, CO2, and their mixtures. Journal of Chemical & Engineering Data, 57(8): 2322–2327

[91]

ManakovARodionova TTerekhovaIKomarovVBurdinA SizikovA (2011). Structural and physico-chemical studies of ionic clathrate hydrates of tetrabutyland tetraisoamylammonium salts. In: Proceedings of the 7th International Conference on Gas Hydrates, Edinburgh, Scotland, United Kingdom, July 17–21

[92]

Mayoufi N, Dalmazzone D, Fürst W, Delahaye A, Fournaison L. (2010). CO2 enclathration in hydrates of peralkyl-(ammonium/phosphonium) salts: stability conditions and dissociation enthalpies. Journal of Chemical & Engineering Data, 55(3): 1271–1275

[93]

Mayoufi N, Dalmazzone D, Delahaye A, Clain P, Fournaison L, Fürst W. (2011). Experimental data on phase behavior of simple tetrabutylphosphonium bromide (TBPB) and mixed CO2+TBPB semiclathrate hydrates. Journal of Chemical & Engineering Data, 56(6): 2987–2993

[94]

McMullan R, Jeffrey G A. (1959). Hydrates of the tetra n-butyl and tetra i-amyl quaternary ammonium salts. Journal of Chemical Physics, 31(5): 1231–1234

[95]

McMullan R K, Bonamico M, Jeffrey G A. (1963). Polyhedral clathrate hydrates. V. Structure of the tetra-n-butyl ammonium fluoride hydrate. Journal of Chemical Physics, 39(12): 3295–3310

[96]

Mehta A P, Makogon T Y, Burruss R C, Wendlandt R F, Sloan E D. (1996). A composite phase diagram of structure H hydrates using Schreinemakers’ geometric approach. Fluid Phase Equilibria, 121(1–2): 141–165

[97]

Meysel P, Oellrich L, Raj Bishnoi P, Clarke M A. (2011). Experimental investigation of incipient equilibrium conditions for the formation of semi-clathrate hydrates from quaternary mixtures of (CO2+N2+TBAB+H2O). Journal of Chemical Thermodynamics, 43(10): 1475–1479

[98]

MiwaYMatsumura KTakeyaKTaniA (2018). THz-TDS Study on Tetrabutylammonium Bromide Hydrate, 43rd International Conference on Infrared, Millimeter, and Terahertz Waves (IRMMW-THz), Nagoya, Japan, September 9–14

[99]

Miyamoto T, Koyama R, Kurokawa N, Hotta A, Alavi S, Ohmura R. (2020). Thermophysical property measurements of tetrabutylphosphonium oxalate (TBPOx) ionic semiclathrate hydrate as a media for the thermal energy storage system. Frontiers in Chemistry, 8: 547

[100]

Mohammadi A, Manteghian M, Mohammadi A H. (2013a). Dissociation data of semiclathrate hydrates for the systems of tetra-n-butylammonium fluoride (TBAF)+methane+water, TBAF+carbon dioxide+water, and TBAF+nitrogen+water. Journal of Chemical & Engineering Data, 58(12): 3545–3550

[101]

Mohammadi A H, Eslamimanesh A, Belandria V, Richon D. (2011). Phase equilibria of semiclathrate hydrates of CO2, N2, CH4, or H2+tetra-n-butylammonium bromide aqueous solution. Journal of Chemical & Engineering Data, 56(10): 3855–3865

[102]

Mohammadi A H, Eslamimanesh A, Belandria V, Richon D, Naidoo P, Ramjugernath D. (2012). Phase equilibrium measurements for semi-clathrate hydrates of the (CO2+N2+tetra-n-butylammonium bromide) aqueous solution system. Journal of Chemical Thermodynamics, 46: 57–61

[103]

Mohammadi A H, Eslamimanesh A, Richon D. (2013b). Semi-clathrate hydrate phase equilibrium measurements for the CO2+H2/CH4+tetra-n-butylammonium bromide aqueous solution system. Chemical Engineering Science, 94: 284–290

[104]

Momeni K, Jomekian A, Bazooyar B. (2020). Semi-clathrate hydrate phase equilibria of carbon dioxide in presence of tetra-n-butyl-ammonium chloride (TBAC): experimental measurements and thermodynamic modeling. Fluid Phase Equilibria, 508: 112445

[105]

Muromachi S. (2020). Phase equilibrium data for semiclathrate hydrates formed with tetra-n-butylammonium (bromide or chloride) and tetra-n-butylphosphonium (bromide or chloride) under hydrogen+carbon dioxide pressure. Fluid Phase Equilibria, 506: 112389

[106]

Muromachi S. (2021). CO2 capture properties of semiclathrate hydrates formed with tetra-n-butylammonium and tetra-n-butylphosphonium salts from H2+CO2 mixed gas. Energy, 223: 120015

[107]

Muromachi S, Hashimoto H, Maekawa T, Takeya S, Yamamoto Y. (2016a). Phase equilibrium and characterization of ionic clathrate hydrates formed with tetra-n-butylammonium bromide and nitrogen gas. Fluid Phase Equilibria, 413: 249–253

[108]

Muromachi S, Kida M, Takeya S, Yamamoto Y, Ohmura R. (2015). Characterization of the ionic clathrate hydrate of tetra-n-butylammonium acrylate. Canadian Journal of Chemistry, 93(9): 954–959

[109]

Muromachi S, Takeya S. (2017). Gas-containing semiclathrate hydrate formation by tetra-n-butylammonium carboxylates: acrylate and butyrate. Fluid Phase Equilibria, 441: 59–63

[110]

Muromachi S, Takeya S. (2018). Design of thermophysical properties of semiclathrate hydrates formed by tetra-n-butylammonium hydroxybutyrate. Industrial & Engineering Chemistry Research, 57(8): 3059–3064

[111]

Muromachi S, Takeya S. (2019). Thermodynamic properties and crystallographic characterization of semiclathrate hydrates formed with tetra-n-butylammonium glycolate. ACS Omega, 4(4): 7317–7322

[112]

Muromachi S, Takeya S, Alavi S, Ripmeester J A. (2022). Structural CO2 capture preference of semiclathrate hydrate formed with tetra-n-butylammonium chloride. CrystEngComm, 24(24): 4366–4371

[113]

Muromachi S, Takeya S, Yamamoto Y, Ohmura R. (2014a). Characterization of tetra-n-butylphosphonium bromide semiclathrate hydrate by crystal structure analysis. CrystEngComm, 16(10): 2056–2060

[114]

Muromachi S, Udachin K A, Alavi S, Ohmura R, Ripmeester J A. (2016b). Selective occupancy of methane by cage symmetry in TBAB ionic clathrate hydrate. Chemical Communications (Cambridge), 52(32): 5621–5624

[115]

Muromachi S, Udachin K A, Shin K, Alavi S, Moudrakovski I L, Ohmura R, Ripmeester J A. (2014b). Guest-induced symmetry lowering of an ionic clathrate material for carbon capture. Chemical Communications (Cambridge), 50(78): 11476–11479

[116]

Oshima M, Jin Y, Kida M, Nagao J. (2020). Thermodynamic and crystallographic properties depending on hydration numbers in tetra-n-butylammonium chloride semiclathrate hydrates. Journal of Chemical Thermodynamics, 142: 106004

[117]

Oshima M, Kida M, Nagao J. (2018). Hydration numbers and thermal properties of tetra-n-butylammonium bromide semiclathrate hydrates determined by ion chromatography and differential scanning calorimetry. Journal of Chemical Thermodynamics, 123: 32–37

[118]

Oshima M, Shimada W, Hashimoto S, Tani A, Ohgaki K. (2010). Memory effect on semi-clathrate hydrate formation: a case study of tetragonal tetra-n-butyl ammonium bromide hydrate. Chemical Engineering Science, 65(20): 5442–5446

[119]

OyamaHEbinuma TShimadaWTakeyaSNagao JUchidaTNaritaH (2003). An experimental study of gas-hydrate formation by measuring viscosity and infrared spectra. Canadian Journal of Physics, 81(1–2): 485–492

[120]

OyamaHShimada WEbinumaTKamataYTakeyaS UchidaTNagao JNaritaH (2005). Phase diagram, latent heat, and specific heat of TBAB semiclathrate hydrate crystals. Fluid Phase Equilibria, 234(1–2): 131–135

[121]

Park S, Lee S, Lee Y, Seo Y. (2013). CO2 capture from simulated fuel gas mixtures using semiclathrate hydrates formed by quaternary ammonium salts. Environmental Science & Technology, 47(13): 7571–7577

[122]

Rakkappan S R, Sivan S, Praveen B, Naarendharan M, Sai Sudhir P. (2021). Thermal property, charging and discharging characteristics study on tetra-n-butyl ammonium bromide semi-clathrate hydrates for air-conditioning cold storage and secondary refrigerant applications. Journal of Chemical Thermodynamics, 153: 106275

[123]

Rodionova T, Komarov V, Villevald G, Aladko L, Karpova T, Manakov A. (2010). Calorimetric and structural studies of tetrabutylammonium chloride ionic clathrate hydrates. Journal of Physical Chemistry B, 114(36): 11838–11846

[124]

Rodionova T V, Komarov V Y, Villevald G V, Karpova T D, Kuratieva N V, Manakov A Y. (2013). Calorimetric and structural studies of tetrabutylammonium bromide ionic clathrate hydrates. Journal of Physical Chemistry B, 117(36): 10677–10685

[125]

RodionovaT VManakovA YSteninY G VillevaldG VKarpovaT D (2008). The heats of fusion of tetrabutylammonium fluoride ionic clathrate hydrates. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 61(1–2): 107–111

[126]

Rodionova T V, Terekhova I S, Manakov A Y. (2022). Ionic clathrate hydrates of tetraalkylammonium/phosphonium salts: structures, properties, some applications, and perspectives. Energy & Fuels, 36(18): 10458–10477

[127]

Rodriguez C T, Le Q D, Focsa C, Pirim C, Chazallon B. (2020). Influence of crystallization parameters on guest selectivity and structures in a CO2-based separation process using TBAB semi-clathrate hydrates. Chemical Engineering Journal, 382: 122867

[128]

Sakamoto H, Sato K, Shiraiwa K, Takeya S, Nakajima M, Ohmura R. (2011). Synthesis, characterization and thermal-property measurements of ionic semi-clathrate hydrates formed with tetrabutylphosphonium chloride and tetrabutylammonium acrylate. RSC Advances, 1(2): 315–322

[129]

Sakamoto J, Hashimoto S, Tsuda T, Sugahara T, Inoue Y, Ohgaki K. (2008). Thermodynamic and Raman spectroscopic studies on hydrogen+tetra-n-butyl ammonium fluoride semi-clathrate hydrates. Chemical Engineering Science, 63(24): 5789–5794

[130]

Sales Silva L P, Dalmazzone D, Stambouli M, Lesort A L, Arpentinier P, Trueba A, Fürst W. (2016). Phase equilibria of semi-clathrate hydrates of tetra-n-butyl phosphonium bromide at atmospheric pressure and in presence of CH4 and CO2+CH4. Fluid Phase Equilibria, 413: 28–35

[131]

Sánchez-Mora M F, Galicia-Luna L A, Pimentel-Rodas A, Mohammadi A H. (2019). Experimental Determination of gas hydrates dissociation conditions in CO2/N2+ethanol/1-propanol/TBAB/TBAF+water systems. Journal of Chemical & Engineering Data, 64(2): 763–770

[132]

Sato K, Tokutomi H, Ohmura R. (2013). Phase equilibrium of ionic semiclathrate hydrates formed with tetrabutylammonium bromide and tetrabutylammonium chloride. Fluid Phase Equilibria, 337: 115–118

[133]

Shimada J, Shimada M, Sugahara T, Tsunashima K. (2019). Phase equilibrium relations of tetra-n-butylphosphonium propionate and butyrate semiclathrate hydrates. Fluid Phase Equilibria, 485: 61–66

[134]

Shimada J, Shimada M, Sugahara T, Tsunashima K, Tani A, Tsuchida Y, Matsumiya M. (2018). Phase equilibrium relations of semiclathrate hydrates based on tetra-n-butylphosphonium formate, acetate, and lactate. Journal of Chemical & Engineering Data, 63(9): 3615–3620

[135]

ShimadaWEbinuma TOyamaHKamataYNaritaH (2005a). Free-growth forms and growth kinetics of tetra-n-butyl ammonium bromide semi-clathrate hydrate crystals. Journal of Crystal Growth, 274(1–2): 246–250

[136]

Shimada W, Ebinuma T, Oyama H, Kamata Y, Takeya S, Uchida T, Nagao J, Narita H. (2003). Separation of gas molecule using tetra-n-butyl ammonium bromide semi-clathrate hydrate crystals. Japanese Journal of Applied Physics, 42(2A): L129–131

[137]

Shimada W, Shiro M, Kondo H, Takeya S, Oyama H, Ebinuma T, Narita H. (2005b). Tetra-n-butylammonium bromide-water (1/38). Acta Crystallographica. Section C, Crystal Structure Communications, 61(2): o65–o66

[138]

Stoporev A, Mendgaziev R, Artemova M, Semenov A, Novikov A, Kiiamov A, Emelianov D, Rodionova T, Fakhrullin R, Shchukin D. (2020). Ionic clathrate hydrates loaded into a cryogel–halloysite clay composite for cold storage. Applied Clay Science, 191: 105618

[139]

Stoporev A S, Kiiamov A G, Varfolomeev M A, Rodionova T V, Manakov A Y. (2021). Metastable ionic cubic structure I clathrate hydrate formed with tetra-n-butylammonium bromide. Mendeleev Communications, 31(1): 17–19

[140]

Sugahara T, Machida H. (2017). Dissociation and nucleation of tetra-n-butyl ammonium bromide semi-clathrate hydrates at high pressures. Journal of Chemical & Engineering Data, 62(9): 2721–2725

[141]

Suginaka T, Sakamoto H, Iino K, Sakakibara Y, Ohmura R. (2013). Phase equilibrium for ionic semiclathrate hydrate formed with CO2, CH4, or N2 plus tetrabutylphosphonium bromide. Fluid Phase Equilibria, 344: 108–111

[142]

Suginaka T, Sakamoto H, Iino K, Takeya S, Nakajima M, Ohmura R. (2012). Thermodynamic properties of ionic semiclathrate hydrate formed with tetrabutylphosphonium bromide. Fluid Phase Equilibria, 317: 25–28

[143]

Sun Q, Guo X, Liu A, Liu B, Huo Y, Chen G. (2011a). Experimental study on the separation of CH4 and N2 via hydrate formation in TBAB solution. Industrial & Engineering Chemistry Research, 50(4): 2284–2288

[144]

Sun Z G, Jiang C M, Xie N L. (2008). Hydrate equilibrium conditions for tetra-n-butyl ammonium bromide. Journal of Chemical & Engineering Data, 53(10): 2375–2377

[145]

Sun Z G, Liu C G, Zhou B, Xu L Z. (2011b). Phase equilibrium and latent heat of tetra-n-butylammonium chloride semi-clathrate hydrate. Journal of Chemical & Engineering Data, 56(8): 3416–3418

[146]

Tang J, Zeng D, Wang C, Chen Y, He L, Cai N. (2013). Study on the influence of SDS and THF on hydrate-based gas separation performance. Chemical Engineering Research & Design, 91(9): 1777–1782

[147]

Tohidi B, Burgass R, Danesh A, Todd A. (1994). Experimental study on the causes of disagreements in methane hydrate dissociation data. Annals of the New York Academy of Sciences, 715(1): 532–534

[148]

Tohidi B, Burgass R W, Danesh A, Østergaard K K, Todd A C. (2000). Improving the accuracy of gas hydrate dissociation point measurements. Annals of the New York Academy of Sciences, 912(1): 924–931

[149]

Trueba A T, Radović I R, Zevenbergen J F, Peters C J, Kroon M C. (2013). Kinetic measurements and in situ Raman spectroscopy study of the formation of TBAF semi-hydrates with hydrogen and carbon dioxide. International Journal of Hydrogen Energy, 38(18): 7326–7334

[150]

UdachinK ALipkowski J (2002). Water-fluorine chains in (n-Bu)4NF·5.5H2O hydrate. Journal of Supramolecular Chemistry, 2(4-5): 449–451

[151]

Veluswamy H P, Chin W I, Linga P. (2014). Clathrate hydrates for hydrogen storage: the impact of tetrahydrofuran, tetra-n-butylammonium bromide and cyclopentane as promoters on the macroscopic kinetics. International Journal of Hydrogen Energy, 39(28): 16234–16243

[152]

Wang F, Fu S, Guo G, Jia Z Z, Luo S J, Guo R B. (2016). Experimental study on hydrate-based CO2 removal from CH4/CO2 mixture. Energy, 104: 76–84

[153]

Wang X, Dennis M. (2015). An experimental study on the formation behavior of single and binary hydrates of TBAB, TBAF and TBPB for cold storage air conditioning applications. Chemical Engineering Science, 137: 938–946

[154]

Wang X, Song C. (2020). Carbon capture from flue gas and the atmosphere: a perspective. Frontiers in Energy Research, 8: 560849

[155]

Wang X, Zhang F, Lipiński W. (2020a). Research progress and challenges in hydrate-based carbon dioxide capture applications. Applied Energy, 269: 114928

[156]

Wang Y, Zhong D L, Li Z, Li J B. (2020b). Application of tetra-n-butylammonium bromide semi-clathrate hydrate for CO2 capture from unconventional natural gases. Energy, 197: 117209

[157]

Wilberforce T, Baroutaji A, Soudan B, Al-Alami A H, Olabi A G. (2019). Outlook of carbon capture technology and challenges. Science of the Total Environment, 657: 56–72

[158]

Xia Z M, Chen Z Y, Li X S, Zhang Y, Yan K F, Lv Q N, Xu C G, Cai J. (2012). Thermodynamic equilibrium conditions for simulated landfill gas hydrate formation in aqueous solutions of additives. Journal of Chemical & Engineering Data, 57(11): 3290–3295

[159]

Xia Z M, Li X S, Chen Z Y, Li G, Yan K F, Xu C G, Lv Q N, Cai J. (2016). Hydrate-based CO2 capture and CH4 purification from simulated biogas with synergic additives based on gas solvent. Applied Energy, 162: 1153–1159

[160]

Xie F M, Li X Y, Zhong D L, Englezos P, Lu G X. (2021). A Calorimetric study on the phase behavior of tetra-n-butyl phosphonium bromide+CO2 semiclathrate hydrate and evaluation of CO2 consumption—impact of a surfactant. Journal of Chemical & Engineering Data, 66(11): 4228–4235

[161]

Xu C G, Zhang S H, Cai J, Chen Z Y, Li X S. (2013). CO2 (carbon dioxide) separation from CO2–H2 (hydrogen) gas mixtures by gas hydrates in TBAB (tetra-n-butyl ammonium bromide) solution and Raman spectroscopic analysis. Energy, 59: 719–725

[162]

Yamauchi Y, Arai Y, Yamasaki T, Endo F, Hotta A, Ohmura R. (2017a). Phase equilibrium temperature and dissociation heat of ionic semiclathrate hydrate formed with tetrabutylammonium butyrate. Fluid Phase Equilibria, 441: 54–58

[163]

Yamauchi Y, Yamasaki T, Endo F, Hotta A, Ohmura R. (2017b). Thermodynamic properties of ionic semiclathrate hydrate formed with tetrabutylammonium propionate. Chemical Engineering & Technology, 40(10): 1810–1816

[164]

Yan J, Lu Y Y, Zhong D L, Qing S L. (2019). Insights into the phase behaviour of tetra-n-butyl ammonium bromide semi-clathrates formed with CO2, (CO2+CH4) using high-pressure DSC. Journal of Chemical Thermodynamics, 137: 101–107

[165]

Yang H, Huang X, Hu J L, Thompson R, Roger J F. (2022). Achievements, challenges and global implications of China’s carbon neutral pledge. Frontiers of Environmental Science & Engineering, 16(8): 111

[166]

Ye N, Zhang P. (2012). Equilibrium data and morphology of tetra-n-butyl ammonium bromide semiclathrate hydrate with carbon dioxide. Journal of Chemical & Engineering Data, 57(5): 1557–1562

[167]

Ye N, Zhang P. (2014a). Phase equilibrium and morphology characteristics of hydrates formed by tetra-n-butyl ammonium chloride and tetra-n-butylphosphonium chloride with and without CO2. Fluid Phase Equilibria, 361: 208–214

[168]

Ye N, Zhang P. (2014b). Phase equilibrium conditions and carbon dioxide separation efficiency of tetra-n-butylphosphonium bromide hydrate. Journal of Chemical & Engineering Data, 59(9): 2920–2926

[169]

Yue G, Liu A, Sun Q, Li X, Lan W, Yang L, Guo X. (2018). The combination of 1-octyl-3-methylimidazolium tetrafluorborate with TBAB or THF on CO2 hydrate formation and CH4 separation from biogas. Chinese Journal of Chemical Engineering, 26(12): 2495–2502

[170]

Zang X, Liang D. (2017). Phase equilibrium data for semiclathrate hydrate of synthesized binary CO2/CH4 gas mixture in tetra-n-butylammonium bromide aqueous solution. Journal of Chemical & Engineering Data, 62(2): 851–856

[171]

Zhang P, Ye N, Zhu H, Xiao X. (2013). Hydrate equilibrium conditions of tetra-n-butylphosphonium bromide+carbon dioxide and the crystal morphologies. Journal of Chemical & Engineering Data, 58(6): 1781–1786

[172]

Zheng J, Bhatnagar K, Khurana M, Zhang P, Zhang B Y, Linga P. (2018). Semiclathrate based CO2 capture from fuel gas mixture at ambient temperature: effect of concentrations of tetra-n-butylammonium fluoride (TBAF) and kinetic additives. Applied Energy, 217: 377–389

[173]

Zheng J, Zhang P, Linga P. (2017). Semiclathrate hydrate process for pre-combustion capture of CO2 at near ambient temperatures. Applied Energy, 194: 267–278

[174]

Zhong D, Englezos P. (2012). Methane separation from coal mine methane gas by tetra-n-butylammonium bromide semiclathrate hydrate formation. Energy & Fuels, 26(4): 2098–2106

[175]

Zhong D L, Wang W C, Zou Z L, Lu Y Y, Yan J, Ding K. (2018). Investigation on methane recovery from low-concentration coal mine gas by tetra-n-butyl ammonium chloride semiclathrate hydrate formation. Applied Energy, 227: 686–693

[176]

Zhou X, Liang D. (2019). Enhanced performance on CO2 adsorption and release induced by structural transition that occurred in TBAB·26H2O hydrates. Chemical Engineering Journal, 378(12): 122128

[177]

Zhuang Q, Clements B, Dai J, Carrigan L. (2016). Ten years of research on phase separation absorbents for carbon capture: achievements and next steps. International Journal of Greenhouse Gas Control, 52: 449–460

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