Abstract
CO2 absorbents were prepared from polyethylene glycol and the polyamidines having N,N′-disubstituted amidine structure in the main chain synthesized through acid-catalyzed melt polycondensation of orthoesters and α,ω-diamines. The homogeneous binary mixtures with the polyamidines captured CO2 much more efficiently under CO2 flow than the one with polyethyleneimine. Furthermore, we investigated the CO2 capture and release by the binary mixtures in terms of effects of the volatility and the structure of polyamidines, temperature, and polyethylene glycol. Taking into consideration the results thus obtained, we conducted CO2 capture/release cycles with the CO2 capture step at 40 °C and with the CO2 releasing step at 80 °C in an alternating manner, thereby demonstrating the repeatability of CO2 capture and release by the binary system of the polyamidine and polyethylene glycol.
References
Falkowski P, Scholes RJ, Boyle E, Canadell J, Canfield D, Elser J, Gruber N, Hibbard K, Högberg P, Linder S, Mackenzie FT, Moore B III, Pedersen T, Rosenthal Y, Seitzinger S, Smetacek V, Steffen W (2000) The global carbon cycle: a test of our knowledge of earth as a system. Science 290:291–296
Rochelle GT (2009) Amine scrubbing for CO2 capture. Science 325:1652–1654
Hunt AJ, Sin EHK, Marriott R, Clark JH (2010) Generation, capture, and utilization of industrial carbon dioxide. ChemSusChem 3:306–322
Jones CW (2011) CO2 capture from dilute gases as a component of modern global carbon management. Annu Rev Chem Biomol Eng 2:31–52
Monastersky R (2013) Global carbon dioxide levels near worrisome milestone. Nature 497:13–14
D’Alessandro DM, Smit B, Long JR (2010) Carbon dioxide capture: prospects for new materials. Angew Chem Int Ed 49:6058–6082
Zhang Z, Yao Z-Z, Xiang S, Chen B (2014) Perspective of microporous metal-organic frameworks for CO2 capture and separation. Energy Environ Sci 7:2868–2899
Lu X, Jin D, Wei S, Wang Z, An C, Guo W (2015) Strategies to enhance CO2 capture and separation based on engineering absorbent materials. J Mater Chem A 3:12118–12132
Sumida K, Rogow DL, Mason JA, McDonald TM, Bloch ED, Herm ZR, Bae T-H, Long JR (2012) Carbon dioxide capture in metal-organic frameworks. Chem Rev 112:724–781
Millward AR, Yaghi OM (2005) Metal-organic frameworks with exceptionally high capacity for storage of carbon dioxide at room temperature. J Am Chem Soc 127:17998–17999
McDonald TM, Lee WR, Mason JA, Wiers BM, Hong CS, Long JR (2012) Capture of carbon dioxide from air and flue gas in the alkylamine-appended metal, äìorganic framework mmen-Mg2(dobpdc). J Am Chem Soc 134:7056–7065
McDonald TM, Mason JA, Kong X, Bloch ED, Gygi D, Dani A, Crocella V, Giordanino F, Odoh SO, Drisdell WS, Vlaisavljevich B, Dzubak AL, Poloni R, Schnell SK, Planas N, Lee K, Pascal T, Wan LF, Prendergast D, Neaton JB, Smit B, Kortright JB, Gagliardi L, Bordiga S, Reimer JA, Long JR (2015) Cooperative insertion of CO2 in diamine-appended metal-organic frameworks. Nature 519:303–308
Tsuda T, Fujiwara T (1992) Polyethyleneimine and macrocyclic polyamine silica gels acting as carbon dioxide absorbents. J Chem Soc Chem Commun 1659–1661
Choi S, Drese JH, Eisenberger PM, Jones CW (2011) Application of amine-tethered solid sorbents for direct CO2 capture from the ambient air. Environ Sci Technol 45:2420–2427
Goeppert A, Czaun M, May RB, Prakash GKS, Olah GA, Narayanan SR (2011) Carbon dioxide capture from the air using a polyamine based regenerable solid adsorbent. J Am Chem Soc 133:20164–20167
Goeppert A, Zhang H, Czaun M, May RB, Prakash GKS, Olah GA, Narayanan SR (2014) Easily regenerable solid adsorbents based on polyamines for carbon dioxide capture from the air. ChemSusChem 7:1386–1397
Goeppert A, Meth S, Prakash GKS, Olah GA (2010) Nanostructured silica as a support for regenerable high-capacity organoamine-based CO2 sorbents. Energy Environ Sci 3:1949–1960
Meth S, Goeppert A, Prakash GKS, Olah GA (2012) Silica nanoparticles as supports for regenerable co2 sorbents. Energy Fuels 26:3082–3090
Al-Azzawi OM, Hofmann CM, Baker GA, Baker SN (2012) Nanosilica-supported polyethoxyamines as low-cost, reversible carbon dioxide sorbents. J Colloid Interface Sci 385:154–159
Zhu J, Baker SN (2014) Lewis base polymers for modifying sorption and regeneration abilities of amine-based carbon dioxide capture materials. ACS Sustainable Chem Eng 2:2666–2674
Harlick PJE, Sayari A (2006) Applications of pore-expanded mesoporous silicas. 3. Triamine silane grafting for enhanced CO2 adsorption. Ind Eng Chem Res 45:3248–3255
Kuwahara Y, Kang D-Y, Copeland JR, Brunelli NA, Didas SA, Bollini P, Sievers C, Kamegawa T, Yamashita H, Jones CW (2012) Dramatic enhancement of CO2 uptake by poly(ethyleneimine) using zirconosilicate supports. J Am Chem Soc 134:10757–10760
Araki S, Kiyohara Y, Tanaka S, Miyake Y (2012) Adsorption of carbon dioxide and nitrogen on zeolite rho prepared by hydrothermal synthesis using 18-crown-6 ether. J Colloid Interface Sci 388:185–190
Lu W, Sculley JP, Yuan D, Krishna R, Wei Z, Zhou H-C (2012) Polyamine-tethered porous polymer networks for carbon dioxide capture from flue gas. Angew Chem Int Ed 51:7480–7484
Nagai D, Suzuki A, Maki Y, Takeno H (2011) Reversible chain association/dissociation via a CO2 responsive crosslinking/decrosslinking system. Chem Comm 47:8856–8858
Nagai D, Suzuki A, Kuribayashi T (2011) Synthesis of hydrogels from polyallylamine with carbon dioxide as gellant: development of reversible co2 absorbent. Macromol Rapid Commun 32:404–410
Han D, Tong X, Boissière O, Zhao Y (2012) General strategy for making CO2-switchable polymers. ACS Macro Lett 1:57–61
Hoshino Y, Imamura K, Yue M, Inoue G, Miura Y (2012) Reversible absorption of CO2 triggered by phase transition of amine-containing micro- and nanogel particles. J Am Chem Soc 134:18177–18180
Morse AJ, Armes SP, Thompson KL, Dupin D, Fielding LA, Mills P, Swart R (2013) Novel pickering emulsifiers based on ph-responsive poly(2-(diethylamino)ethyl methacrylate) latexes. Langmuir 29:5466–5475
Yue M, Hoshino Y, Ohshiro Y, Imamura K, Miura Y (2014) Temperature-responsive microgel films as reversible carbon dioxide absorbents in wet environment. Angew Chem Int Ed 53:2654–2657
Sakaguchi T, Takeda A, Hashimoto T (2011) Highly gas-permeable silanol-functionalized poly(diphenylacetylene)s: synthesis, characterization, and gas permeation property. Macromolecules 44:6810–6817
Sakaguchi T, Katsura F, Iwase A, Hashimoto T (2014) CO2-permselective membranes of crosslinked poly(vinyl ether)s bearing oxyethylene chains. Polymer 55:1459–1466
Sakaguchi T, Tsuzuki T, Masuda T, Hashimoto T (2014) Synthesis, gas permeability, and metal-induced gelation of poly(disubstituted acetylene)s having p, m-dimethoxyphenyl and p, m-dihydroxyphenyl groups. Polymer 55:1977–1983
Sakaguchi T, Shinoda Y, Hashimoto T (2014) Synthesis and gas permeability of nitrated and aminated poly(diphenylacetylene)s. Polymer 55:6680–6685
Bates ED, Mayton RD, Ntai I, Davis JH (2002) CO2 capture by a task-specific ionic liquid. J Am Chem Soc 124:926–927
Wang C-M, Mahurin SM, Luo H-M, Baker GA, Li H-R, Dai S (2010) Reversible and robust co2 capture by equimolar task-specific ionic liquid-superbase mixtures. Green Chem 12:870–874
Wang C, Luo H, Luo X, Li H, Dai S (2010) Equimolar co2 capture by imidazolium-based ionic liquids and superbase systems. Green Chem 12:2019–2023
Endo T, Nagai D, Monma T, Yamaguchi H, Ochiai B (2004) A novel construction of a reversible fixation-release system of carbon dioxide by amidines and their polymers. Macromolecules 37:2007–2009
Ochiai B, Yokota K, Fujii A, Nagai D, Endo T (2008) Reversible trap-release of CO2 by polymers bearing dbu and dbn moieties. Macromolecules 41:1229–1236
Nagai D, Endo T (2009) Synthesis of 1 h-quinazoline-2,4-diones from 2-aminobenzonitriles by fixation of carbon dioxide with amidine moiety supported polymer at atmospheric pressure. J Polym Sci, Part A: Polym Chem 47:653–657
Barkakaty B, Morino K, Sudo A, Endo T (2010) Amidine-mediated delivery of CO2 from gas phase to reaction system for highly efficient synthesis of cyclic carbonates from epoxides. Green Chem 12:42–44
Heldebrant DJ, Jessop PG, Thomas CA, Eckert CA, Liotta CL (2005) The reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with carbon dioxide. J Org Chem 70:5335–5338
Jessop PG, Heldebrant DJ, Li X, Eckert CA, Liotta CL (2005) Green chemistry: reversible nonpolar-to-polar solvent. Nature 436:1102
Liu Y, Jessop PG, Cunningham M, Eckert CA, Liotta CL (2006) Switchable surfactants. Science 313:958–960
Heldebrant DJ, Yonker CR, Jessop PG, Phan L (2008) Organic liquid CO2 capture agents with high gravimetric CO2 capacity. Energy Environ Sci 1:487–493
Su X, Jessop PG, Cunningham MF (2012) Surfactant-free polymerization forming switchable latexes that can be aggregated and redispersed by CO2 removal and then readdition. Macromolecules 45:666–670
Zhang Q, Wang W-J, Lu Y, Li B-G, Zhu S (2011) Reversibly coagulatable and redispersible polystyrene latex prepared by emulsion polymerization of styrene containing switchable amidine. Macromolecules 44:6539–6545
Zhang Q, Yu G, Wang W-J, Yuan H, Li B-G, Zhu S (2012) Preparation of N2/CO2 triggered reversibly coagulatable and redispersible latexes by emulsion polymerization of styrene with a reactive switchable surfactant. Langmuir 28:5940–5946
Heldebrant DJ, Jessop PG (2003) Liquid poly(ethylene glycol) and supercritical carbon dioxide: a benign biphasic solvent system for use and recycling of homogeneous catalysts. J Am Chem Soc 125:5600–5601
Li X, Hou M, Zhang Z, Han B, Yang G, Wang X, Zou L (2008) Absorption of CO2 by ionic liquid/polyethylene glycol mixture and the thermodynamic parameters. Green Chem 10:879–884
Tanthana J, Chuang SSC (2010) In situ infrared study of the role of peg in stabilizing silica-supported amines for CO2 capture. ChemSusChem 3:957–964
Yang Z-Z, He L-N, Zhao Y-N, Li B, Yu B (2011) CO2 capture and activation by superbase/polyethylene glycol and its subsequent conversion. Energy Environ Sci 4:3971–3975
Furusho Y, Endo T (2013) Capture and release of CO2 by polyamidine. J Polym Sci, Part A: Polym Chem 51:3404–3411
Sakuragi M, Aoyagi N, Furusho Y, Endo T (2014) Reversible fixation and release of carbon dioxide by binary system consisting of polyethylene glycol and polystyrene-bearing cyclic amidine pendant group. J Polym Sci, Part A: Polym Chem 52:2025–2031
Jin R-H, Yuan J-J (2009) Biomimetically controlled formation of nanotextured silica/titania films on arbitrary substrates and their tunable surface function. Adv Mater 21:3750–3753
Matsukizono H, Jin R-H (2012) High-temperature-resistant chiral silica generated on chiral crystalline templates at neutral ph and ambient conditions. Angew Chem Int Ed 51:5862–5865
Pirrung FOH, Loen EM, Noordam A (2002) Hyperbranched polymers as a novel class of pigment dispersants. Macromol Symp 187:683–693
Thunemann AF (2002) Polyelectrolyte-surfactant complexes (synthesis, structure and materials aspects). Prog Polym Sci 27:1473–1572
Böhme F, Klinger C, Komber H, Haubler L, Jehnichen D (1998) Synthesis and properties of polyamidines. J Polym Sci, Part A: Polym Chem 36:929–938
Böhme F, Klinger C, Bellmann C (2001) Surface properties of polyamidines. Colloids Surf A 189:21–27
Tenkovtsev AV, Yakimansky AV, Dudkina MM, Lukoshkin VV, Komber H, Häussler L, Böhme F (2001) Ionic complexes of bis(hydroxyarylidene)alkanones with strong polymeric bases as a new class of third-order nonlinear optical chromophores. Macromolecules 34:7100–7107
Sharavanan K, Komber H, Böhme F (2002) Synthesis and properties of aliphatic polyacetamidines. Macromol Chem Phys 203:1852–1858
Xu F, Sun J, Shen Q (2002) Samarium diiodide promoted synthesis of N, N’-disubstituted amidines. Tetrahedron Lett 43:1867–1869
The pKa values reported for N,N′-diethylacetamidine and N,N′-diethylbenzamidine in aqueous solutions are 13.08 and 12.49, respectively (By calculations using Advance Chemistry Development (ACD/Laboratories) Software (v11.02, SciFinder database))
Tanaka Y, Katagiri H, Furusho Y, Yashima E (2005) A modular strategy to artificial double helices. Angew Chem Int Ed 44:3867–3870
Ikeda M, Furusho Y, Okoshi K, Tanahara S, Maeda K, Nishino S, Mori T, Yashima E (2006) A luminescent poly(phenylenevinylene)-amylose composite with supramolecular liquid crystallinity. Angew Chem Int Ed 45:6491–6495
Katagiri H, Tanaka Y, Furusho Y, Yashima E (2007) Multicomponent cylindrical assemblies driven by amidinium-carboxylate salt-bridge formation. Angew Chem Int Ed 46:2435–2439
Nakatani Y, Furusho Y, Yashima E (2010) Amidinium carboxylate salt bridges as a recognition motif for mechanically interlocked molecules: synthesis of an optically active [2]catenane and control of its structure. Angew Chem Int Ed 49:5463–5467
Yamada H, Wu Z-Q, Furusho Y, Yashima E (2012) Thermodynamic and kinetic stabilities of complementary double helices utilizing amidinium, äìcarboxylate salt bridges. J Am Chem Soc 134:9506–9520
Furusho Y, Endo T (2014) Supramolecular polymer gels formed from carboxy-terminated telechelic polybutadiene and polyamidine through amidinium-carboxylate salt bridge. J Polym Sci, Part A: Polym Chem 52:1815–1824
Sakuragi M, Aoyagi N, Furusho Y, Endo T (2016) Supramolecular polymer gels from polystyrene bearing cyclic amidine group and acrylic acid/n-butyl acrylate copolymers. J Polym Sci, Part A: Polym Chem 54:765–770
Furusho Y, Endo T, Higaki K, Kaetsu K, Higaki Y, Kojio K, Takahara A (2016) Supramolecular network polymers formed from polyamidine and carboxy-terminated telechelic poly(n-butyl acrylate) via amidinium-carboxylate salt bridges. J Polym Sci, Part A: Polym Chem 54:2148–2155
Acknowledgments
This work was supported by JSPS KAKENHI Grant Number 26410102 and Asahi Glass Foundation. The authors thank Dr. Yasuhiro Ishida at RIKEN for his help in rheological measurements.
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Furusho, Y., Endo, T. Reversible capture and release of carbon dioxide by binary system of polyamidine and polyethylene glycol. Polym. Bull. 74, 1207–1219 (2017). https://doi.org/10.1007/s00289-016-1772-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-016-1772-6