Inhibitory effects of novel green inhibitors on gas hydrate formation

doi:10.1016/j.cjche.2019.02.016

Abstract

Abstract: Natural gas hydrates easily form in pipelines, causing potential safety issues during oil and gas production and transportation. Injecting gas hydrate inhibitors is one of the most effective methods for preventing gas hydrate formation or aggregation. However, some thermodynamic hydrate inhibitors are toxic and harmful to the environment, whereas degradation of kinetic inhibitors is difficult. Therefore, environmentally friendly and easily biodegradable novel green inhibitors have been proposed and investigated. This paper provides a short but systematic review of the inhibitory performance of amino acids, antifreeze proteins, and ionic liquids. For different hydrate formation systems, the influences of the inhibitor type, structure, and concentration on the inhibitory effects are summarized. The mechanism of green inhibitors as kinetic inhibitors is also discussed. The

Key words: Gas hydrate, Inhibition, Green inhibitors, Kinetic inhibitors, Thermodynamic inhibitors

摘要： Natural gas hydrates easily form in pipelines, causing potential safety issues during oil and gas production and transportation. Injecting gas hydrate inhibitors is one of the most effective methods for preventing gas hydrate formation or aggregation. However, some thermodynamic hydrate inhibitors are toxic and harmful to the environment, whereas degradation of kinetic inhibitors is difficult. Therefore, environmentally friendly and easily biodegradable novel green inhibitors have been proposed and investigated. This paper provides a short but systematic review of the inhibitory performance of amino acids, antifreeze proteins, and ionic liquids. For different hydrate formation systems, the influences of the inhibitor type, structure, and concentration on the inhibitory effects are summarized. The mechanism of green inhibitors as kinetic inhibitors is also discussed. The

关键词: Gas hydrate, Inhibition, Green inhibitors, Kinetic inhibitors, Thermodynamic inhibitors

Cuiping Tang, Deqing Liang. Inhibitory effects of novel green inhibitors on gas hydrate formation[J]. Chinese Journal of Chemical Engineering, 2019, 27(9): 2107-2117.

Cuiping Tang, Deqing Liang. Inhibitory effects of novel green inhibitors on gas hydrate formation[J]. 中国化学工程学报, 2019, 27(9): 2107-2117.

References

[1] E.G. Hammerschmidt, Formation of gas hydrates in natural gas transmission lines, Ind. Eng. Chem. 26(8) (1934) 851-855.
[2] E.D. Sloan, C.A. Koh, Clathrate Hydrates of Natural Gases, Taylor & Francis, New York, 2008.
[3] R. Sassen, S.T. Sweet, D.A. DeFreitas, A.V. Milkov, Exclusion of 2-methylbutane (isopentane) during crystallization of structure II gas hydrate in sea-floor sediment, Gulf of Mexico, Org. Geochem. 31(2000) 1257-1262.
[4] H. Ohno, T.A. Strobel, S.F. Dec, E.D. Sloan, C.A. Koh, Raman studies of methaneethane hydrate metastability, J. Phys. Chem. A 113(2009) 1711-1716.
[5] Y.J. Xu, M.L. Yang, X.X. Yang, Chitosan as green kinetic inhibitors for gas hydrate formation, J. Nat. Gas Chem. 19(2010) 431-435.
[6] S. Mokhatab, R.J. Wilkens, K.J. Leontaritis, A review of strategies for solving gashydrate problems in subsea pipelines, Energ. Source Part A 29(2007) 39-45.
[7] M. Wu, S.M. Wang, H.B. Liu, A study on inhibitors for the prevention of hydrate formation in gas transmission pipeline, J. Nat. Gas Chem. 16(2007) 81-85.
[8] M.A. Kelland, History of the development of low dosage hydrates inhibitors, Energ Fuel, 20(3)(2006)825-847.
[9] M.A. Kelland, T.M. Svartaas, L.A. Dybvik, Control of Gas Hydrate Formation by Surfactants and Polymers, Proceedings of the SPE International Symposium, New Orleans, United States of America, 1994.
[10] K.L. Yan, C.Y. Sun, J. Chen, L.T. Chen, D.J. Shen, B. Liu, M.L. Jia, M. Niu, Y.N. Lv, N. Li, Z.Y. Song, S.S. Niu, G.J. Chen, Flow characteristics and rheological properties of natural gas hydrate slurry in the presence of anti-agglomerant in a flow loop apparatus, Chem. Eng. Sci. 106(2014) 99-108.
[11] H.B. Qin, C.Y. Sun, Z.F. Sun, B. Liu, G.J. Chen, Relationship between the interfacial tension and inhibition performance of hydrate inhibitors, Chem. Eng. Sci. 143(2016) 182-189.
[12] J.P. Lederhos, J.P. Long, A. Sum, R.L. Christiansen, E.D. Sloan, Effective kinetic inhibitors for natural gas hydrates, Chem. Eng. Sci. 51(1996) 1221-1229.
[13] P.C. Chua, M.A. Kelland, Poly(N-vinyl azacyclooctanone):a more powerful structure II kinetic hydrate inhibitor than poly(N-vinyl caprolactam), Energ Fuel 26(7) (2012) 4481-4485.
[14] X.L.A. Ding, N. Maeda, S. Wang, K.A. Kozielski, P.G. Hartley, Synthesis of effective kinetic inhibitors for natural gas hydrates, Energ Fuel 26(2) (2012) 1037-1043.
[15] H.B. Qin, Z.F. Sun, X.Q. Wang, J.L. Yang, C.Y. Sun, B. Liu, L.Y. Yang, G.J. Chen, Synthesis and evaluation of two new kinetic hydrate inhibitors, Energ Fuel 29(2015) 7135-7141.
[16] T.J. Carver, M.G.B. Drew, P.M. Rodger, Inhibition of crystal growth in methane hydrate, J. Chem. Soc. 91(1995) 3449-3460.
[17] R. Larsen, C.A. Knight, E.D. Sloan, Clathrate hydrate growth and inhibition, Fluid Phase Equilibr 150-151(1998) 353-360.
[18] H.E. King, J.L. Hutter, M.Y. Lin, T. Sun, Polymer conformations of gas hydrate kinetic inhibitors:a small-angle neutron scattering study, J. Chem. Phys. 112(2000) 2523-2532.
[19] N. Daraboina, J.A. Ripmeester, V.K. Walker, P. Englezos, Natural gas hydrate formation and decomposition in the presence of kinetic inhibitors. 2. Stirred reactor experiments, Energ Fuel 25(2011) 4384-4391.
[20] M.A. Kelland, T.M. Svartaas, J. Øvsthus, T. Namba, A new class of kinetic hydrate inhibitor, Ann. N. Y. Acad. Sci. 912(2009) 281-293.
[21] Y.H. Wang, Y.J. Chen, L. Bao, X.M. Lang, S.S. Fan, Molecular dynamics simulation of CH₄ hydrate deposition in the presence of poly (2-ehtyle-2-oxazoline), Acta Phys. Sin. 28(2012) 1683-1690.
[22] T.J. Carver, M.G.B. Drew, P.M. Rodger, Molecular dynamics calculations of Nmethylpyrrolidone in liquid water, Phys. Chem. Chem. Phys. 1(1999) 1807-1816.
[23] M. Varma-Nair, C.A. Costello, K.S. Colle, H.E. King, Thermal analysis of polymer-water interactions and their relation to gas hydrate inhibition, J. Appl. Polym. Sci. 103(2007) 2642-2653.
[24] X. Zhao, Z. Qiu, W. Huang, Characterization of kinetics of hydrate formation in the presence of kinetic hydrate inhibitors during deepwater drilling, J. Nat. Gas Sci. Eng. 22(2015) 270-278.
[25] L.D. Villano, M.A. Kelland, G.M. Miyake, E.Y.-X. Chen, Effect of polymer tacticity on the performance of poly(N,N-dialkylacrylamide)s as kinetic hydrate inhibitors, Energ Fuel 24(2010) 2554-2562.
[26] H. Roostaa, A. Dashtia, S.H. Mazloumi, F. Varaminian, The dual effect of amino acids on the nucleation and growth rate of gas hydrate in ethane+water, methane+ propane+water and methane+THF+water systems, Fuel 212(2018) 151-161.
[27] J.H. Sa, G.H. Kwak, B.R. Lee, D.H. Park, K. Han, K.H. Lee, Hydrophobic amino acids as a new class of kinetic inhibitors for gas hydrate formation, Sci. Rep. 3(2013) 2428.
[28] J.H. Sa, G.H. Kwak, K. Han, D. Ahn, K.H. Lee, Gas hydrate inhibition by perturbation of liquid water structure, Sci. Rep. 5(2015) 11526.
[29] Mitra Maddah, Mina Maddah, K. Peyvandi, Molecular dynamics simulation of methane hydrate formation in presence and absence of amino acid inhibitors, J. Mol. Liq. 269(2018) 721-732.
[30] H. Roosta, A. Dashti, S.H. Mazloumi, F. Varaminian, Inhibition properties of new amino acids for prevention of hydrate formation in carbon dioxide-water system:Experimental and modeling investigations, J. Mol. Liq. 215(2016) 656-663.
[31] P. Naeiji, A. Arjomandi, F. Varaminian, Amino acids as kinetic inhibitors for tetrahydrofuran hydrate formation:Experimental study and kinetic modeling, J. Nat. Gas Sci. Eng. 21(2014) 64-70.
[32] J.H. Sa, G.H. Kwak, K. Han, D. Ahn, S.G. Cho, J.D. Lee, K.H. Lee, Inhibition of methane and natural gas hydrate formation by altering the structure of water with amino acids, Sci. Rep. 6(2016) 31582.
[33] S.A. Rad, K.R. Khodaverdiloo, M. Karamoddin, F. Varaminian, K. Peyvandi, Kinetic study of amino acids inhibition potential of Glycine and L-leucine on the ethane hydrate formation, J. Nat. Gas Sci. Eng. 26(2015) 819-826.
[34] J.H. Sa, G.H. Kwak, B.R. Lee, D. Ahn, K.H. Lee, Abnormal incorporation of amino acids into the gas hydrate crystal lattice, Phys. Chem. Chem. Phys:PCCP 16(2014) 26730-26734.
[35] J.H. Sa, B.R. Lee, D.H. Park, K. Han, H.D. Chun, K.H. Lee, Amino acids as natural inhibitors for hydrate formation in CO₂ sequestration, Environ. Sci. Technol. 45(2011) 5885-5891.
[36] T. Park, D. Kyung, W. Lee, Effect of organic matter on Co₂ hydrate phase equilibrium in phyllosilicate suspensions, Environ. Sci. Technol. 48(2014) 6597-6603.
[37] C.B. Bavoh, B. Partoon, B. Lal, G. Gonfa, S.F. Khor, A.M. Sharif, Inhibition effect of amino acids on carbon dioxide hydrate, Chem. Eng. Sci. 171(2017) 331-339.
[38] C.B. Bavoh, M.S. Khan, B. Lal, N.I.B.A. Ghaniri, K.M. Sabil, New methane hydrate phase boundary data in the presence of aqueous amino acids, Fluid Phase Equilibr. 478(2018) 129-133.
[39] C.B. Bavoh, B. Partoon, B. Lal, L.K. Keong, Methane hydrate-liquid-vapourequilibrium phase condition measurements in the presence of natural amino acids, J. Nat. Gas. Sci. Eng. 37(2017) 425-434.
[40] G. Bhattacharjee, N. Choudhary, A. Kumar, S. Chakrabarty, R. Kumar, Effect of the amino acid L-histidine on methane hydrate growth kinetics, J. Nat. Gas. Sci. Eng. 35(2016) 1453-1462.
[41] H.P. Veluswamy, P.Y. Lee, K. Premasinghe, P. Linga, Effect of biofriendly amino acids on the kinetics of methane hydrate formation and dissociation, Ind. Eng. Chem. Res. 56(2017) 6145-6154.
[42] V.K. Walker, H. Zeng, H. Ohno, N. Daraboina, H. Sharifi, S.A. Bagherzadeh, S. Alavi, P. Englezoset, Antifreezeproteinsas gashydrate inhibitors, Can. J. Chem. 93(2015) 1-11.
[43] H.A. Zhou, C.I. Ferreira, Effect of type-III Anti-Freeze Proteins (AFPs) on CO₂ hydrate formation rate, Chem. Eng. Sci. 167(2017) 42-53.
[44] H. Zeng, L.D. Wilson, V.K. Walker, J.A. Ripmeester, Effect of antifreeze proteins on the nucleaton, growth, and the memory effect during tetrahydrofuran clathrate hydrate formation, J. Am. Chem. Soc. 128(9) (2006) 2844-2850.
[45] H. Zeng, L.D. Wilson, V.K. Walker, J.A. Ripmeester, The inhibition of tetrahydrofuran clathrate-hydrate formation with antifreeze protein, Can. J. Phys. 81(1-2) (2003) 17-24.
[46] H. Zeng, A. Brown, H. Wathen, J.A. Ripmeester, V.K. Walker, Antifreeze Proteins, Adsorption to Ice, Silica and Gas Hydrates; Proceedings of the 5th International Conference on Gas Hydrates, Trondheim, Norway, 2005.
[47] R. Gordienko, H. Ohno, V.K. Singh, Z. Jia, J.A. Ripmeester, V.K. Walker, Towards a green hydrate inhibitor:imaging antifreeze proteins on clathrates, Plos One 5(2) (2010), e8953..
[48] H. Zeng, I.L. Moudrakovski, J.A. Ripmeester, V.K. Walker, Effect of antifreeze protein on nucleation, growth and memory of gas hydrates, AIChE J. 52(9) (2006) 3304-3309.
[49] S. Al-Adel, J.A.G. Dick, R. El-Ghafari, P. Servio, The effect of biological and polymeric inhibitors on methane gas hydrate growth kinetics, Fluid Phase Equilib 267(1) (2008) 92-98.
[50] C.M. Perfeldt, P.C. Chua, N. Daraboina, D. Friis, E. Kristiansen, H. Ramløv, J.M. Woodley, M.A. Kelland, N. von Solms, Inhibition of gas hydrate nucleation and growth:efficacy of an antifreeze protein from the longhorn beetle rhagium mordax, Energ Fuel 28(2014) 3666-3672.
[51] L. Jensen, H. Ramlov, K. Thomsen, N. von Solms, Inhibition of methane hydrate formation by ice-structuring proteins, Ind. Eng. Chem. Res. 49(4) (2010) 1486-1492.
[52] L.U. Udegbunam, J.R. DuQuesnay, L. Osorio, V.K. Walker, J.G. Beltran, Phase equilibria, kinetics and morphology of methane hydrate inhibited by antifreeze proteins:application of a novel 3-in-1 method, J. Chem. Thermodynamics 117(2018) 155-163.
[53] H. Bruusgaard, L.D. Lessard, P. Servio, Morphology study of structure i methane hydrate formation and decomposition of water droplets in the presence of biological and polymeric kinetic inhibitors, Cryst. Growth Des. 9(7) (2009) 3014-3023.
[54] N. Daraboina, I. Moudrakovski, J.A. Ripmeester, V.K. Walker, P. Englezos, Assessing the performance of commercial and biological gas hydrate inhibitors using nuclear magnetic resonance microscopy and a stirred autoclave, Fuel 105(2013) 630-635.
[55] H. Ohno, R. Susilo, R. Gordienko, J. Ripmeester, V.K. Walker, Interaction of antifreeze proteins with hydrocarbon hydrates, Chem. Eur. J. 16(2010) 10409-10417.
[56] H. Sharifi, V.K. Walker, J.A. Ripmeester, P. Englezos, Insights into the behaviour of biological clathrate hydrate inhibitors in aqueous saline solutions, Cryst. Growth Des. 14(2014) 2923-2930.
[57] H. Sharifi, V.K. Walker, J. Ripmeester, P. Englezos, Inhibition activity of antifreeze proteins with natural gas hydrates in saline and the light crude oil mimic, heptane, Energ Fuel 28(2014) 3712-3717.
[58] L. Jensen, K. Thomsen, N. von Solms, Inhibition of structure I and II gas hydrates using synthetic and biological kinetic inhibitors, Energ Fuel 25(2011) 17-23.
[59] D.R. Nutt, J.C. Smith, Dual function of the hydration layer around an antifreeze protein revealed by atomistic molecular dynamics simulations, J. Am. Chem. Soc. 130(2008) 13066-13073.
[60] T. Sun, P.L. Davies, V.K. Walker, Structural basis for the inhibition of gas hydrates by a-helical antifreeze proteins, Biophys. J. 109(8) (2015) 1698-1705.
[61] S.A. Bagherzadeh, S. Alavi, J.A. Ripmeester, P. Englezos, Why ice-binding type I antifreeze protein acts as a gas hydrate crystal inhibitor, Phys. Chem. Chem. Phys 17(2015) 9984-9990.
[62] R.D. Rogers, K.R. Seddon, Ionic liquids-Solvents of the future? Science 302(2003) 792-793.
[63] M. Tariq, D. Rooney, E. Othman, S. Aparicio, M. Atilhan, M. Khraisheh, Gas hydrate inhibition:A review of the role of ionic liquids, Ind. Eng. Chem. Res. 53(2014) 17855-17868.
[64] O. Nashed, D. Dadebayev, M.S. Khan, C.B. Bavoh, B. Lal, A.M. Shariff, Experimental and modelling studies on thermodynamic methane hydrate inhibition in the presence of ionic liquids, J. Mol. Liq. 249(2018) 886-891.
[65] B. Partoon, N.M.S. Wong, K.M. Sabil, K. Nasrifar, M.R. Ahmad, A study on thermodynamics effect of[EMIM]-Cl and[OHC₂MIM]-Cl on methane hydrate equilibrium line, Fluid Phase Equilib. 337(2013) 26-31.
[66] C.K. Chu, S.T. Lin, Y.P. Chen, P.C. Chen, L.J. Chen, Chain length effect of ionic liquid 1-alkyl-3-methylimidazolium chloride on the phase equilibrium of methane hydrate, Fluid Phase Equilib. 413(2016) 57-64.
[67] C. Xiao, N. Wibisono, H. Adidharma, Dialkylimidazolium halide ionic liquids as dual function inhibitors for methane hydrate, Chem. Eng. Sci. 65(2010) 3080-3087.
[68] Z. Long, X. Zhou, X. Shen, D. Li, D. Liang, Phase equilibria and dissociation enthalpies of methane hydrate in imidazolium ionic liquid aqueous solutions, Ind. Eng. Chem. Res. 54(2015) 11701-11708.
[69] A.R. Richard, H. Adidharma, The performance of ionic liquids and their mixtures in inhibiting methane hydrate formation, Chem. Eng. Sci. 87(2013) 270-276.
[70] Z. Long, Y. He, X. Zhou, D. Li, D. Liang, Phase behavior of methane hydrate in the presence of imidazolium ionic liquids and their mixtures, Fluid Phase Equilibr. 439(2017) 1-8.
[71] C.K. Chu, P.C. Chen, Y.P. Chen, S.T. Lin, L.J. Chen, Inhibition effect of 1-ethyl-3-methylimidazolium chloride on methane hydrate equilibrium, J. Chem. Thermodyn. 91(2015) 141-145.
[72] X.S. Li, Y.J. Liu, Z.Y. Zeng, Z.Y. Chen, G. Li, H.J. Wu, Equilibrium hydrate formation conditions for the mixtures of methane + ionic liquids + water, J. Chem. Eng. Data 56(2011) 119-123.
[73] K.M. Sabil, O. Nashed, B. Lal, L. Ismail, A. Japper-Jaafar, Experimental investigation on the dissociation conditions of methane hydrate in the presence of imidazolium-based ionic liquid, J. Chem. Thermodynamics 84(2015) 7-13.
[74] P. Gupta, S. Sakthivel, J.S. Sangwai, Effect of aromatic/aliphatic based ionic liquids on the phase behavior of methane hydrates:Experiments and modeling, J. Chem. Thermodynamics 117(2018) 9-20.
[75] L. Keshavarz, J. Javanmardi, A. Eslamimanesh, A.H. Mohammadi, Experimental measurement and modeling of methane hydrate dissociation conditions in the presence of aqueous solutions of ionic liquid, Fluid Phase Equilib. 354(2013) 312-318.
[76] W. Lee, J.Y. Shin, K.S. Kim, S.P. Kang, Kinetic promotion and inhibition of methane hydrate formation by morpholinium ionic liquids with chloride and tetrafluoroborate anions, Energ. Fuel 30(2016) 3879-3885.
[77] W. Lee, J.Y. Shin, J.H. Cha, K.S. Kim, S.P. Kang, Inhibition effect of ionic liquids and their mixtures with poly(N-vinylcaprolactam) on methane hydrate formation, J. Ind. Eng. Chem. 38(2016) 211-216.
[78] N.A. Mohamed, M. Tariqa, M. Atilhan, M. Khraisheh, D. Rooney, G. Garcia, S. Aparicio, Investigation of the performance of biocompatible gas hydrate inhibitors via combined experimental and DFT methods, J. Chem. Thermodynamics 111(2017) 7-19.
[79] M. Zare, A. Haghtalab, A.N. Ahmadi, K. Nazari, Experiment and thermodynamic modeling of methane hydrate equilibria in the presence of aqueous imidazoliumbased ionic liquid solutions using electrolyte cubic square well equation of state, Fluid Phase Equilibr. 341(2013) 61-69.
[80] K. Nazari, A.N. Ahmadi, M.R. Moradi, V. Sahraei, V. Taghikhani, C.A. Ghobti, Thermodynamic study of methane hydrate formation in the presence of[BMIM] [BF₄] and[BMIM] [MS] ionic liquids, Proceedings of the 7th International Conference on Gas Hydrates, EScotland, U.K., 2011
[81] K. Nazari, M.R. Moradi, A.N. Ahmadi, Kinetic modeling of methane hydrate formation in the presence of low-dosage water-soluble ionic liquids, Chem. Eng. Technol. 36(2013) 1915-1923.
[82] K. Tumba, P. Reddy, P. Naidoo, D. Ramjugernath, Phase equilibria of methane and carbon dioxide clathrate hydrates in the presence of aqueous solutions of tributylmethylphosphonium methylsulfate ionic liquid, J. Chem. Eng. Data 56(2011) 3620-3629.
[83] C. Xiao, H. Adidharma, Dual function inhibitors for methane hydrate, Chem. Eng. Sci. 64(2009) 1522-1527.
[84] K.S. Kim, S.P. Kang, Investigation of Pyrrolidinium- and Morpholinium-Based Ionic Liquids into Kinetic Hydrate Inhibitors on Structure I Methane Hydrate, Proceedings of the 7th International Conference on Gas Hydrates, Scotland, U.K. 2011.
[85] K.S. Kim, J.W. Kang, S.P. Kang, Tuning ionic liquids for hydrate inhibition, Chem. Commun. 47(2011) 6341-6343.
[86] J.H. Cha, C. Ha, S. Han, Y.K. Hong, S.P. Kang, J.W. Kang, K.S. Kim, Experimental measurement of phase equilibrium of hydrate in water + ionic liquid + CH₄ system, J. Chem. Eng. Data 61(2016) 543-548.
[87] Z. Long, X. Zhou, D. Liang, D. Li, Experimental study of methane hydrate equilibria in[EMIM]-NO₃ aqueous solutions, J. Chem. Eng. Data 60(2015) 2728-2732.
[88] T. Altamash, M. Khraisheh, M.F. Qureshi, M.A. Saad, S. Aparicio, M. Atilhan, Costeffective alkylammonium formate-based protic ionic liquids for methane hydrate inhibition, J. Nat. Gas. Sci. Eng. 58(2018) 59-68.
[89] M. Tariq, E. Connor, J. Thompson, M. Khraisheh, M. Atilhan, D. Rooney, Doubly dual nature of ammonium-based ionic liquids for methane hydrates probed by rockingrig assembly, RSC Adv. 6(2016) 23827-23836.
[90] M.S. Khan, B. Partoon, C.B. Bavoh, B. Lal, N.B. Mellon, Influence of tetramethylammonium hydroxide on methane and carbon dioxide gas hydrate phase equilibrium conditions, Fluid Phase Equilib. 440(2017) 1-8.
[91] Q. Chen, Y. Yu, P. Zeng, W. Yang, Q. Liang, X. Peng, Y. Liu, Y. Hu, Effect of 1-butyl-3-methylimidazolium tetrafluoroborate on the formation rate of CO₂ hydrate, J. Nat. Gas Chem. 17(2008) 264-267.
[92] M.S. Khan, C.B. Bavoh, B. Partoon, B. Lal, M.A. Bustam, A.M. Shariff, Thermodynamic effect of ammonium based ionic liquids on CO₂ hydrates phase boundary, J. Mol. Liq. 238(2017) 533-539.
[93] B.S. Shin, E.S. Kim, S.K. Kwak, J.S. Lim, K.S. Kim, J.W. Kang, Thermodynamic inhibition effects of ionic liquids on the formation of condensed carbon dioxide hydrate, Fluid Phase Equilibr. 382(2014) 270-278.
[94] T. Makino, Y. Matsumoto, T. Sugahara, K. Ohgaki, H. Masuda, Effect of Ionic Liquid on Hydrate Formation Rate in Carbon Dioxide Hydrates, Proceedings of the 7th International Conference on Gas Hydrates, Scotland, U.K. 2011.
[95] J.H. Cha, C. Ha, S.P. Kang, J.W. Kang, K.S. Kim, Thermodynamic inhibition of CO₂ hydrate in the presence of morpholinium and piperidinium ionic liquids, Fluid Phase Equilibr. 413(2016) 75-79.
[96] M. Tariq, M. Atilhan, M. Khraisheh, E. Othman, M. Castier, G. García, S. Aparicio, B. Tohidi, Experimental and DFT approach on the determination of natural gas hydrate equilibrium with the use of excess N₂ and choline chloride ionic liquid as an inhibitor, Energ Fuel 30(2016) 2821-2832.
[97] M.S. Khan, C.B. Bavoh, B. Partoon, O. Nashed, B. Lal, N.B. Mellon, Impacts of ammonium based ionic liquids alkyl chain on thermodynamic hydrate inhibition for carbon dioxide rich binary gas, J. Mol. Liq. 261(2018) 283-290.
[98] M. Zare, A. Haghtalab, A.N. Ahmadi, K. Nazari, A. Mehdizadeh, Effect of imidazolium based ionic liquids and ethylene glycol monoethyl ether solutions on the kinetic of methane hydrate formation, J. Mol. Liq. 204(2015) 236-242.
[99] A. Rasoolzadeh, J. Javanmardi, A. Eslamimanesh, A.H. Mohammadi, Experimental study and modeling of methane hydrate formation induction time in the presence of ionic liquids, J. Mol. Liq. 221(2016) 149-155.
[100] S.P. Kang, E.S. Kim, J.Y. Shin, H.T. Kim, J.W. Kang, J.H. Cha, K.S. Kim, Unusual synergy effect on methane hydrate inhibition when ionic liquid meets polymer, RSC Adv. 3(2013) 19920-19923.
[101] O.Nashed,K.M. Sabil, L. Ismail, A. Japper-Jaafar, B.Lal, Mean induction time and isothermal kinetic analysis of methane hydrate formation in water and imidazolium based ionic liquid solutions, J. Chem. Thermodynamics 117(2018) 147-154.
[102] L.D. Villano, M.A. Kelland, An investigation into the kinetic hydrate inhibitor properties of two imidazolium-based ionic liquids on structure II gas hydrate, Chem. Eng. Sci. 65(2010) 5366-5372.
[103] W. Lee, J.Y. Shin, K.S. Kim, S.P. Kang, Synergetic effect of ionic liquids on the kinetic inhibition performance of poly(N-vinylcaprolactam) for natural gas hydrate formation, Energ Fuel 30(2016) 9162-9169.
[104] X.D. Shen, L.L. Shi, Z. Long, X.B. Zhou, D.Q. Liang, Experimental study on the kinetic effect of N-butyl-N-methylpyrrolidinium bromide on CO₂ hydrate, J. Mol. Liq. 223(2016) 672-677.
[105] K.C. Lee, J. Azuraien, Ionic liquid as low dosage hydrate inhibitor for flow assurance in pipeline, Asian J. Sci. Res. 6(2013) 374-380.
[106] M.E.H. Nasrollah, B. Abareshi, C. Ghotbi, V. Taghikhani, A.H. Jalili, Investigation of Six Imidazolium-Based Ionic Liquids as Thermo-Kinetic Inhibitors for Methane Hydrate by Molecular Dynamics Simulation, Proceedings of the 2nd National Iranian Conference on Gas Hydrate, Iran 2013.
[107] M.F. Qureshi, M. Atilhan, T. Altamash, M. Tariq, M. Khraisheh, S. Aparicio, B. Tohidi, Gas hydrate prevention and flow assurance by using mixtures of ionic liquids and synergent compounds:combined kinetics and thermodynamic approach, Energ Fuel 30(2016) 3541-3548.
[108] S.P. Kang, T. Jung, J.W. Lee, Macroscopic and spectroscopic identifications of the synergetic inhibition of anionic liquid on hydrate formations, Chem. Eng. Sci. 143(2016) 270-275.
[109] W. Lee, K.S. Kim, S.P. Kang, J.N. Kim, Synergetic performance of the mixture of poly (N-vinylcaprolactam) and a pyrrolidinium-based ionic liquid for kinetic hydrate inhibition in the presence of the mineral oil phase, Energ Fuel 32(2018) 4932-4941.
[110] T. Kitajima, N. Ohtsubo, S. Hashimoto, T. Makino, D. Kodama, K. Ohgaki, Study on prompt methane hydrate formation derived by addition of ionic liquid, American Chemical Science Journal 2(3) (2012) 100-110.
[111] J.D. Lee, H.J. Wu, P. Englezos, Cationic starches as gas hydrate kinetic inhibitors, Chem. Eng. Sci. 62(2007) 6548-6555.
[112] M.R. Talaghat, Enhancement of the performance of modified starch as a kinetic hydrate inhibitor in the presence of polyoxides for simple gas hydrate formation in a flow mini-loop apparatus, J. Nat. Gas Sci. Eng. 18(2014) 7-12.
[113] S.R. Xu, S.S. Fan, S.T. Fang, X.M. Lang, Y.H. Wang, J. Chen, Pectin as an extraordinary natural kinetic hydrate inhibitor, Sci. Rep. 6(2016) 23220.
[114] T. Saikia, V. Mahto, Experimental investigations of clathrate hydrate inhibition in water based drilling fluid using green inhibitor, J. Petrol. Sci. Eng. 147(2016) 647-653.