Промоторы образования гидрата углекислого газа на основе производных лимонной и аминокислот

Синтезированы и исследованы новые амиды некоторых аминокислот и лимонной кислоты, которые улучшают кинетику образования гидрата углекислого газа. Эти соединения могут стать потенциальными эффективными промоторами гидратообразования при низких концентрациях. Показано, что добавление в раствор амида лимонной кислоты и норлейцина (CTR+Nle) способствует увеличению конверсии воды в гидрат и существенному снижению времени индукции. Так, для раствора с концентрацией 0.05 масс. % конверсия увеличилась до 57 ± 3 %, что на 21 и 3.1 % больше по сравнению с конверсией в системах без добавок и с добавлением раствора додецилсульфата натрия (SDS) соответственно. Время индукции в присутствии CTR+Nle снижается до 35 мин, что в 8.1 раза меньше, чем в отсутствии добавок, и в 5.8 раза меньше, чем в случае применения раствора триптофана, который является известным промотором образования гидратов углекислого газа.

1. Aminu M.D., Nabavi S.A., Rochelle C.A., Manovic V. A review of developments in carbon dioxide storage // Appl. Energy. 2017. V. 208. P. 1389–1419. https://doi.org/10.1016/j.apenergy.2017.09.015.

2. Li L., Fan S., Chen Q., Yang G., Zhao J., Wei N., Wen Y. Experimental and modeling phase equilibria of gas hydrate systems for post-combustion CO2 capture // J. Taiwan Inst. Chem. Eng. 2019. V. 96. P. 35–44. https://doi.org/10.1016/j.jtice.2018.11.007.

3. Babu P., Kumar R., Linga P. Pre-combustion capture of carbon dioxide in a fixed bed reactor using the clathrate hydrate process // Energy. 2013. V. 50. P. 364–373. https://doi.org/10.1016/j.energy.2012.10.046.

4. House K.Z., Schrag D.P., Harvey C.F., Lackner K.S. Permanent carbon dioxide storage in deep-sea sediments // Proc. Natl. Acad. Sci. USA. 2006. V. 103, No 33. P. 12291–12295. https://doi.org/10.1073/pnas.0605318103.

5. Qureshi M.F., Atilhan M., Altamash T., Aparicio S., Aminnaji M., Tohidi B. Highpressure gas hydrate autoclave hydraulic experiments and scale-up modeling on the effect of stirring RPM effect // J. Nat. Gas Sci. Eng. 2017. V. 38. P. 50–58. https://doi.org/10.1016/j.jngse.2016.12.023.

6. Chirkova Y.F., Varfolomeev M.A., Mirzakimov U.Zh., Gainullin S.E., Semenov M.E., Stoporev A.S., Pavelyev R.S. Influence of kinetic promoters with different surface-active properties on methane and natural gas hydrate formation in porous media // Fuel. 2024. V. 369. Art. 131727. https://doi.org/10.1016/j.fuel.2024.131727.

7. Partoon B., Sabil K.M., Lau K.K., Lal B., Nasrifar K. Production of gas hydrate in a semi-batch spray reactor process as a means for separation of carbon dioxide from methane // Chem. Eng. Res. Des. 2018. V. 138. P. 168–175. https://doi.org/10.1016/j.cherd.2018.08.024.

8. Khlebnikov V.N., Antonov S.V., Mishin A.S., Liang M., Khamidullina I.V., Zobov P.M., Likhacheva N.V., Gushchin P.A. Major factors influencing the generation of natural gas hydrate in porous media // Nat. Gas Ind. B. 2017. V. 4, No 6. P. 442–448. https://doi.org/10.1016/j.ngib.2017.09.006.

9. Stoporev A., Kadyrov R., Adamova T., Statsenko E., Nguyen T.H., Yarakhmedov M., Semenov A., Manakov A. Three-dimensional-printed polymeric cores for methane hydrate enhanced growth // Polymers. 2023. V. 15, No 10. Art. 2312. https://doi.org/10.3390/polym15102312.

10. Adeyemo A., Kumar R., Linga P., Ripmeester J., Englezos P. Capture of carbon dioxide from flue or fuel gas mixtures by clathrate crystallization in a silica gel column // Int. J. Greenhouse Gas Control. 2010. V. 4, No 3. P. 478–485. https://doi.org/10.1016/j.ijggc.2009.11.011.

11. Seo Y., Kang S.‑P. Enhancing CO2 separation for pre-combustion capture with hydrate formation in silica gel pore structure // Chem. Eng. J. 2010. V. 161, Nos 1–2. P. 308–312. https://doi.org/10.1016/j.cej.2010.04.032.

12. ZareNezhad B., Montazeri V., Rahimi M. Experimental and theoretical investigations regarding the effect of chromium oxide nanoparticles on the CO2 gas capture through gas hydrate process in petroleum industry // Pet. Sci. Technol. 2019. V. 37, No 8. P. 869–875. https://doi.org/10.1080/10916466.2018.1517166.

13. Li A., Luo D., Jiang L., Wang J., Zhou Y. Experimental study on CO2 hydrate formation in the presence of TiO2, SiO2, MWNTs nanoparticles // Sep. Sci. Technol. 2019. V. 54, No 15. P. 2498–2506. https://doi.org/10.1080/01496395.2018.1548481.

14. Nesterov A.N., Reshetnikov A.M. New combination of thermodynamic and kinetic promoters to enhance carbon dioxide hydrate formation under static conditions // Chem. Eng. J. 2019. V. 378. Art. 122165. https://doi.org/10.1016/j.cej.2019.122165.

15. Hassan M.H.A., Sher F., Zarren G., Suleiman N., Tahir A.A., Snape C.E. Kinetic and thermodynamic evaluation of effective combined promoters for CO2 hydrate formation // J. Nat. Gas Sci. Eng. 2020. V. 78. Art. 103313. https://doi.org/10.1016/j.jngse.2020.103313.

16. Daraboina N., von Solms N. The combined effect of thermodynamic promoters tetrahydrofuran and cyclopentane on the kinetics of flue gas hydrate formation // J. Chem. Eng. Data. 2015. V. 60, No 2. P. 247–251. https://doi.org/10.1021/je500529w.

17. Li S., Fan S., Wang J., Lang X., Wang Y. Clathrate hydrate capture of CO2 from simulated flue gas with cyclopentane/water emulsion // Chin. J. Chem. Eng. 2010. V. 18, No 2. P. 202–206. https://doi.org/10.1016/S1004-9541(08)60343-2.

18. Zhong D.‑L., Wang W.‑C., Lu Y.‑Y., Yan J. Using tetra-n-butyl ammonium chloride semiclathrate hydrate for methane separation from low-concentration coal mine gas // Energy Procedia. 2017. V. 105. P. 4854–4858. https://doi.org/10.1016/j.egypro.2017.03.961.

19. Kumar A., Veluswamy H.P., Kumar R., Linga P. Kinetic promotion of mixed methane– THF hydrate by additives: Opportune to energy storage // Energy Procedia. 2019. V. 158. P. 5287–5292. https://doi.org/10.1016/j.egypro.2019.01.647.

20. Veluswamy H.P., Premasinghe K.P., Linga P. CO2 hydrates – effect of additives and operating conditions on the morphology and hydrate growth // Energy Procedia. 2017. V. 105. P. 5048–5054. https://doi.org/10.1016/j.egypro.2017.03.1019.

21. Torré J.‑P., Ricaurte M., Dicharry C., Broseta D. CO2 enclathration in the presence of water–soluble hydrate promoters: Hydrate phase equilibria and kinetic studies in quiescent conditions // Chem. Eng. Sci. 2012. V. 82. P. 1–13. https://doi.org/10.1016/j.ces.2012.07.025.

22. Phan A., Schlösser H., Striolo A. Molecular mechanisms by which tetrahydrofuran affects CO2 hydrate growth: Implications for carbon storage // Chem. Eng. J. 2021. V. 418. Art. 129423. https://doi.org/10.1016/j.cej.2021.129423.

23. Majid A.A.A., Worley J., Koh C.A. Thermodynamic and kinetic promoters for gas hydrate technological applications // Energy Fuels. 2021. V. 35, No 23. P. 19288–19301. https://doi.org/10.1021/acs.energyfuels.1c02786.

24. Mech D., Gupta P., Sangwai J.S. Kinetics of methane hydrate formation in an aqueous solution of thermodynamic promoters (THF and TBAB) with and without kinetic promoter (SDS) // J. Nat. Gas Sci. Eng. 2016. V. 35, Pt. B. P. 1519–1534. https://doi.org/10.1016/j.jngse.2016.06.013.

25. Partoon B., Javanmardi J. Effect of mixed thermodynamic and kinetic hydrate promoters on methane hydrate phase boundary and formation kinetics // J. Chem. Eng. Data. 2013. V. 58, No 3. P. 501–509. https://doi.org/10.1021/je301153t.

26. Pahlavanzadeh H., Hassan H., Pourranjbar M. Hydrate dissociation conditions of CH4 in the presence of TBANO3 and cyclopentane promoter mixture: Thermodynamic modeling and experimental measurement // J. Chem. Eng. Data. 2020. V. 65, No 4. P. 1927– 1935. https://doi.org/10.1021/acs.jced.9b01108.

27. Yao Y., Guan J., Tang P., Jiao H., Lin C., Wang J., Lu Z., Min H., Gao H. Assessment of toxicity of tetrahydrofuran on the microbial community in activated sludge // Bioresour. Technol. 2010. V. 101, No 14. P. 5213–5221. https://doi.org/10.1016/j.biortech.2010.02.051.

28. Hermida S.A.S., Possari E.P.M., Souza D.B., de Arruda Campos I.P., Gomes O.F., Di Mascio P., Medeiros M.H.G., Loureiro A.P.M. 2ꞌ-Deoxyguanosine, 2ꞌ-deoxycytidine, and 2ꞌ-deoxyadenosine adducts resulting from the reaction of tetrahydrofuran with DNA bases // Chem. Res. Toxicol. 2006. V. 19, No 7. P. 927–936. https://doi.org/10.1021/tx060033d.

29. Liu X., Li Y., Chen G.‑J., Chen D.‑Y., Sun B., Yin Z. Coupling amino acid with THF for the synergistic promotion of CO2 hydrate micro kinetics: Implication for hydrate-based CO2 sequestration // ACS Sustainable Chem. Eng. 2023. V. 11, No 15. P. 6057–6069. https://doi.org/10.1021/acssuschemeng.3c00593.

30. Kim S., Lee S.H., Kang Y.T. Characteristics of CO2 hydrate formation/dissociation in H2O + THF aqueous solution and estimation of CO2 emission reduction by district cooling application // Energy. 2017. V. 120. P. 362–373. https://doi.org/10.1016/j.energy.2016.11.086.

31. Delahaye A., Fournaison L., Marinhas S., Chatti I., Petitet J.‑P., Dalmazzone D., Fürst W. Effect of THF on equilibrium pressure and dissociation enthalpy of CO2 hydrates applied to secondary refrigeration // Ind. Eng. Chem. Res. 2006. V. 45, No 1. P. 391–397. https://doi.org/10.1021/ie050356p.

32. Sun Q., Kang Y.T. Experimental correlation for the formation rate of CO2 hydrate with THF (tetrahydrofuran) for cooling application // Energy. 2015. V. 91. P. 712–719. https://doi.org/10.1016/j.energy.2015.08.089.

33. Liu X., Ren J., Chen D., Yin Z. Comparison of SDS and L-methionine in promoting CO2 hydrate kinetics: Implication for hydrate-based CO2 storage // Chem. Eng. J. 2022. V. 438. Art. 135504. https://doi.org/10.1016/j.cej.2022.135504.

34. Molokitina N.S., Nesterov A.N., Podenko L.S., Reshetnikov A.M. Carbon dioxide hydrate formation with SDS: Further insights into mechanism of gas hydrate growth in the presence of surfactant // Fuel. 2019. V. 235. P. 1400–1411. https://doi.org/10.1016/j.fuel.2018.08.126.

35. Deng X.‑Y., Yang Y., Zhong D.‑L., Li X.‑Y., Ge B.‑B., Yan J. New insights into the kinetics and morphology of CO2 hydrate formation in the presence of sodium dodecyl sulfate // Energy Fuels. 2021. V. 35, No 17. P. 13877–13888. https://doi.org/10.1021/acs.energyfuels.1c01494.

36. Dashti H., Yew L.Z., Lou X. Recent advances in gas hydrate-based CO2 capture // J. Nat. Gas Sci. Eng. 2015. V. 23. P. 195–207. https://doi.org/10.1016/j.jngse.2015.01.033.

37. Zhong Y., Rogers R.E. Surfactant effects on gas hydrate formation // Chem. Eng. Sci. 2000. V. 55, No 19. P. 4175–4187. https://doi.org/10.1016/S0009-2509(00)00072-5.

38. Farhadian A., Heydari A., Maddah M., Hosseini M.S., Sadeh E., Peyvandi K., Varaminian F. Renewable biosurfactants for energy-efficient storage of methane: An experimental and computational investigation // Chem. Eng. J. 2022. V. 427. Art. 131723. https://doi.org/10.1016/j.cej.2021.131723.

39. He Y., Sun M.‑T., Chen C., Zhang G.‑D., Chao K., Lin Y., Wang F. Surfactant-based promotion to gas hydrate formation for energy storage // J. Mater. Chem. A. 2019. V. 7, No 38. P. 21634–21661. https://doi.org/10.1039/C9TA07071K.

40. Mohammadi A., Babakhanpour N., Javidani A.M., Ahmadi G. Corn’s dextrin, a novel environmentally friendly promoter of methane hydrate formation // J. Mol. Liq. 2021. V. 336. Art. 116855. https://doi.org/10.1016/j.molliq.2021.116855.

41. Veluswamy H.P., Bhattacharjee G., Liao J., Linga P. Macroscopic kinetic investigations on mixed natural gas hydrate formation for gas storage application // Energy Fuels. 2020. V. 34, No 12. P. 15257–15269. https://doi.org/10.1021/acs.energyfuels.0c01862.

42. Khandelwal H., Qureshi M.F., Zheng J., Venkataraman P., Barckholtz T.A., Mhadeshwar A.B., Linga P. Effect of L-tryptophan in promoting the kinetics of carbon dioxide hydrate formation // Energy Fuels. 2021. V. 35, No 1. P. 649–658. https://doi.org/10.1021/acs.energyfuels.0c03709.

43. Bhavya T., Sai Kiran B., Prasad P.S.R. The role of stirring and amino acid mixtures to surpass the sluggishness of CO2 hydrates // Energy Fuels. 2021. V. 35, No 17. P. 13937–13944. https://doi.org/10.1021/acs.energyfuels.1c01830.

44. Bhattacharjee G., Linga P. Amino acids as kinetic promoters for gas hydrate applications: A mini review // Energy Fuels. 2021. V. 35, No 9. P. 7553–7571. https://doi.org/10.1021/acs.energyfuels.1c00502.

45. Sai Kiran B., Bhavya T., Prasad P.S.R. Collective impact of amino acids on clathrate hydrates of the CO2 + CH4 gas mixture // Energy Fuels. 2022. V. 36, No 18. P. 10618–10626. https://doi.org/10.1021/acs.energyfuels.2c01329.

46. Pandey J.S., Daas Y.J., Karcz A.P., von Solms N. Methane hydrate formation behavior in the presence of selected amino acids // J. Phys.: Conf. Ser. 2020. V. 1580, No 1. Art. 012003. https://doi.org/10.1088/1742-6596/1580/1/012003.

47. Li Y., Yin Z., Lu H., Xu C., Liu X., Huang H., Chen D., Linga P. Evaluation of amino acid L-leucine as a kinetic promoter for CO2 sequestration as hydrate: A kinetic and morphological study // J. Environ. Chem. Eng. 2023. V. 11, No 6. Art. 111363. https://doi.org/10.1016/j.jece.2023.111363.

48. Srivastava S., Kollemparembil A.M., Zettel V., Claßen T., Gatternig B., Delgado A., Hitzmann B. Experimental investigation of CO2 uptake in CO2 hydrates formation with amino acids as kinetic promoters and its dissociation at high temperature // Sci. Rep. 2022. V. 12, No 1. Art. 8359. https://doi.org/10.1038/s41598-022-12538-1.

49. Prasad P.S.R., Sai Kiran B. Are the amino acids thermodynamic inhibitors or kinetic promoters for carbon dioxide hydrates? // J. Nat. Gas Sci. Eng. 2018. V. 52. P. 461–466. https://doi.org/10.1016/j.jngse.2018.02.001.

50. Pandey J.S., Daas Y.J., von Solms N. Screening of amino acids and surfactant as hydrate promoter for CO2 capture from flue gas // Processes. 2020. V. 8, No 1. Art. 124. https://doi.org/10.3390/pr8010124.

51. Farhadian A., Varfolomeev M., Abdelhay Z., Emelianov D., Delaunay A., Dalmazzone D., Accelerated methane hydrate formation by ethylene diamine tetraacetamide as an efficient promoter for methane storage without foam formation // Ind. Eng. Chem. Res. 2019. V. 58, No 19. P. 7752–7760. https://doi.org/10.1021/acs.iecr.9b00803.

52. Pavelyev R.S., Gainullin S.E., Semenov M.E., Zaripova Y.F., Yarkovoi V.V., Luneva A.I., Farhadian A., Varfolomeev M.A. Dual promotion-inhibition effects of novel ethylenediaminetetraacetic acid bisamides on methane hydrate formation for gas storage and flow assurance applications // Energy Fuels. 2022. V. 36, No 1. P. 290–297. https://doi.org/10.1021/acs.energyfuels.1c03381.

53. Gainullin S.E., Farhadian A., Kazakova P.Y., Semenov M.E., Chirkova Y.F., Heydari A., Pavelyev R.S., Varfolomeev M.A. Novel amino acid derivatives for efficient methane solidification storage via clathrate hydrates without foam formation // Energy Fuels. 2023. V. 37, No 4. P. 3208–3217. https://doi.org/10.1021/acs.energyfuels.2c03923.

54. Gainullin S.E., Kazakova P.Y., Pavelyev R.S., Chirkova Y.F., Semenov M.E., Varfolomeev M.A. Comparison of the promoting activity of amides of ethylenediaminetetraacetic acid and some amino acids in the nucleation and growth of hydrates of methane and carbon dioxide // Chem. Technol. Fuels Oils. 2023. V. 59, No 4. P. 726–731. https://doi.org/10.1007/s10553-023-01576-8.

55. Ballard A.L., Sloan E.D., Jr. The next generation of hydrate prediction: An overview // J. Supramol. Chem. 2002. V. 2, Nos 4–5. P. 385–392. https://doi.org/10.1016/S1472-7862(03)00063-7.

56. Малышев В.Л., Моисеева Е.Ф., Калиновский Ю.В. Расчет коэффициента сверхсжимаемости основных компонент природного газа методом молекулярной динамики // Известия Томского политехнического университета. Инжиниринг георесурсов. 2019. Т. 330, № 11. С. 121–129. https://doi.org/10.18799/24131830/2019/11/2356.