Precipitation study of CO₂-loaded glycinate solution with the introduction of ethanol as an antisolvent

Abstract

Focused beam reflectance measurement (FBRM) and ¹³C nuclear magnetic resonance (¹³C NMR) analysis were used to study the precipitation process of CO₂-loaded potassium glycinate (KGLY) solutions at different CO₂ loadings, during the addition of ethanol as an antisolvent at a rate of 10 mL·min⁻¹. The volume ratio of ethanol added to the KGLY solution (3.0 mol·L⁻¹, 340 mL) ranged from 0 to 3.0. Three solid-liquid-liquid phases were formed during the precipitation process. The FBRM results showed that the number of particles formed increased with CO₂ loading and ethanol addition for CO₂-unsaturated KGLY solutions, whilst for CO₂-saturated KGLY solution it first increased then decreased to a stable value with ethanol addition. ¹³C NMR spectroscopic analysis showed that the crystals precipitated from the CO₂-unsaturated KGLY solutions consisted of glycine only, and the quantity crystallised increased with CO₂ loading and ethanol addition. However, a complex mixture containing glycine, carbamate and potassium bicarbonate was precipitated from CO₂-saturated KGLY solution with the maximum precipitation percentages of 94.3%, 31.4% and 89.6%, respectively, at the ethanol volume fractions of 1.6, 2.5 and 2.3.

Key words： crystallization; precipitation; glycinate; FBRM; ¹³C NMR

Acknowledgments

The authors acknowledge the infrastructure support from the Particulate Fluids Processing Centre (PFPC), the Peter Cook Centre (PCC) for Carbon Capture and Storage (CCS).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-019-1882-4 and is accessible for authorized users.

References

1 Yang H, Xu Z, Fan M, Gupta R, Slimane R B, Bland A E, Wright I. Progress in carbon dioxide separation and capture: A review. Acta Scientiae Circumstantiae, 2008, 20(1): 14–27

2 Davison J, Thambimuthu K. An overview of technologies and costs of carbon dioxide capture in power generation. Proceedings of the Institution of Mechanical Engineers. Part A, Journal of Power and Energy, 2009, 223(3): 201–212

3 Jou F Y, Mather A E, Otto F D. The solubility of CO₂ in a 30 mass% monoethanolamine solution. Canadian Journal of Chemical Engineering, 1995, 73(1): 140–147

4 Hook R J. An investigation of some sterically hindered amines as potential carbon dioxide scrubbing compounds. Industrial & Engineering Chemistry Research, 1997, 36(5): 1779–1790

5 Penny D E, Ritter T J. Kinetic study of the reaction between carbon dioxide and primary amines. Journal of the Chemical Society, Faraday Transactions, 1983, 9(9): 2103–2109

6 Rochelle G T. New amines for CO₂ capture. II. Oxidative degradation mechanisms. Current Opinion in Chemical Engineering, 2012, 1(2): 183–190

7 Park D W, Son Y S, Park D W, Oh K J. Absorption of carbon dioxide into aqueous solution of sodium glycinate. Separation Science and Technology, 2008, 43(11-12): 3003–3019

8 Kumar P S, Hogendoorn J A, Versteeg G F, Feron P H M. Kinetics of the reaction of CO₂ with aqueous potassium salt of taurine and glycine. AIChE Journal. American Institute of Chemical Engineers, 2010, 49(1): 203–213

9 Hu G, Smith K H, Liu L, Kentish S E, Stevens G W. Reaction kinetics and mechanism between histidine and carbon dioxide. Chemical Engineering Journal, 2017, 307(1): 56–62

10 Holst J V, Versteeg G F, Brilman D W F, Hogendoorn J A. Kinetic study of CO₂ with various amino acid salts in aqueous solution. Chemical Engineering Science, 2009, 64(1): 59–68

11 Kumar P, Hogendoorn J, Versteeg G, Feron P. Kinetics of the reaction of CO₂ with aqueous potassium salt of taurine and glycine. AIChE Journal. American Institute of Chemical Engineers, 2003, 49(1): 203–213

12 Portugal A F, Sousa J M, Magalhães F D, Mendes A. Solubility of carbon dioxide in aqueous solutions of amino acid salts. Chemical Engineering Science, 2009, 64(9): 1993–2002

13 Hallenbeck A P, Egbebi A, Resnik K P, Hopkinson D, Anna S L, Kitchin J R. Comparative microfluidic screening of amino acid salt solutions for post-combustion CO₂ capture. International Journal of Greenhouse Gas Control, 2015, 43: 189–197

14 Lim J A, Kim D H, Yoon Y, Jeong S K, Park K T, Nam S C. Absorption of CO₂ into aqueous potassium salt solutions of L-alanine and L-proline. Energy & Fuels, 2012, 26(6): 3910–3918

15 Majchrowicz M E, Brilman D W F. Solubility of CO₂ in aqueous potassium L-prolinate solutions-absorber conditions. Chemical Engineering Science, 2012, 72: 35–44

16 Thee H, Nicholas N J, Smith K H, Da Silva G, Kentish S E, Stevens G W. A kinetic study of CO₂ capture with potassium carbonate solutions promoted with various amino acids: Glycine, sarcosine and proline. International Journal of Greenhouse Gas Control, 2014, 20(Suppl C): 212–222

17 Fernandez E S, Heffernan K, Ham L V V D, Linders M J G, Eggink E, Schrama F N H, Brilman D W F, Goetheer E L V, Vlugt T J H. Conceptual design of a novel CO₂ capture process based on precipitating amino acid solvents. Industrial & Engineering Chemistry Research, 2013, 52(34): 12223–12235

18 Perry R J, Wood B R, Genovese S, O’Brien M J, Westendorf T, Meketa M L, Farnum R, Mcdermott J, Sultanova I, Perry T M, et al. CO₂ capture using phase-changing sorbents. Energy & Fuels, 2012, 26(4): 2528–2538

19 Seo S, Simoni L D, Ma M, Desilva M A, Huang Y, Stadtherr M A, Brennecke J F. Phase-change ionic liquids for postcombustion CO₂ capture. Energy & Fuels, 2014, 28(9): 5968–5977

20 Wang L D, An S L, Li Q W, Yu S H, Wu S Y. Phase change behavior and kinetics of CO₂ absorption into DMBA/DEEA solution in a wetted-wall column. Chemical Engineering Journal, 2017, 314: 681–687

21 Kumar P S, Hogendoorn J A, Feron P H M, Versteeg G F. Equilibrium solubility of CO₂ in aqueous potassium taurate solutions: Part 1. Crystallization in carbon dioxide loaded aqueous salt solutions of amino acids. Industrial & Engineering Chemistry Research, 2003, 42(12): 2832–2840

22 Fernandez E S, Goetheer E L V. DECAB: Process development of a phase change absorption process. Energy Procedia, 2011, 4(1): 868–875

23 Aronu U E, Ciftja A F, Kim I, Hartono A. Understanding precipitation in amino acid salt systems at process conditions. Energy Procedia, 2013, 37: 233–240

24 Bian Y Y, Shen S F. CO₂ absorption into a phase change absorbent: Water-lean potassium prolinate/ethanol solution. Chinese Journal of Chemical Engineering, 2018, 26(11): 2318–2326

25 Holmes P E, Naaz M, Poling B E. Ion Concentrations in the CO₂-NH₃-H₂O system from ¹³C NMR spectroscopy. Industrial & Engineering Chemistry Research, 1998, 37(8): 3281–3287

26 Shi H C, Naami A, Idem R, Sema T, Liang Z W, Usubharatana P, Saiwan C, Tontiwachwuthikul P. NMR analysis of amine-CO₂‒H₂O systems with VLE modeling for CO₂ capture processes. Future Medicinal Chemistry, 2013, 10: 10–31

27 Shi H, Sema T, Naami A, Liang Z, Idem R, Tontiwachwuthikul P. 13C NMR spectroscopy of a novel amine species in the DEAB–CO₂–H₂O system: VLE model. Industrial & Engineering Chemistry Research, 2012, 51(25): 8608–8615