Introduction
Ionic liquids are low-temperature molten salts composed of organic cations and inorganic anions or organic anions. In recent years [1], as the concept of green chemistry has gradually entered people’s vision [2], ionic liquids have begun to attract the attention and competition of scientists from various countries [3], which will play an important role in promoting the future development of humanity [4]. Ionic liquids have excellent physical and chemical properties, such as good thermal stability [5], wide electrochemical window [6], high conductivity, good solubility, good acid-base stability, low vapor pressure, nonvolatile, etc. [7]. At the same time, the synthesis process is simple and easy to recycle and has a broad application space [8]. By controlling the composition of anions and cations of ionic liquids, the density, viscosity [9], surface tension [10], acidity [11], coordination ability [12], and polarity of ionic liquids can be changed [13]. Therefore, they are...
References
Zhao D, Min W, Yuan K, Min E (2002) Ionic liquids: applications in catalysis. Catal Today 74(1):157–189
Valkenberg MH, Decastro C, Hölderich WF (2000) Immobilisation of chloroaluminate ionic liquids on silica materials. Green Chem 14:139–144
Earle MJ, Seddon KR (2010) Ionic liquids: green solvents for the future. Pure Appl Chem 2000(72):1391–1398
Fukumoto K, Yoshizawa M, Ohno H (2005) Room temperature ionic liquids from 20 natural amino acids. J Am Chem Soc 127(8):2398–2399
Laali KK (2003) Ionic liquids in synthesis. Synthesis 11:1752–1752
Lau RM, Rantwijk FV, Seddon KR, Sheldon RA (2010) Lipase-catalyzed reactions in ionic liquids. Org Lett 2:4189–4196
Hapiot P, Lagrost C (2008) Electrochemical reactivity in room-temperature ionic liquids. Chem Rev 108:2238–2264
Gordon CM (2010) New developments in catalysis using ionic liquids. Appl Catal A Gen 222(1):101–117
Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 2001:2399–2407
Aparicio S, Atilhan M (2013) On the properties of CO2 and flue gas at the piperazinium-based ionic liquids interface: a molecular dynamics study. J Phys Chem C 117:15061–15074
Babiker OE, Shuhaimi M, Mutalib MIA (2014) Molecular simulation for piperazinium based ILs: effects of alkyl chain, concentration and anions on henry’s constants. Appl Mech Mater 625:448–453
Cha JH, Ha C, Kang SP, Kang JW, Kim KS (2016) Thermodynamic inhibition of CO2 hydrate in the presence of morpholinium and piperidinium ionic liquids. Fluid Phase Equilib 413:75–79
Cha JH, Kim KS, Lee H (2009) Size-selective Pd nanoparticles stabilized by dialkylmorpholinium ionic liquids. Korean J Chem Eng 26:760–764
Chaban VV, Prezhdo OV (2015) Are fluorination and chlorination of morpholinium-based ionic liquids favorable? J Phys Chem B 119:9920–9924
Hayyan M, Mjalli FS, Hashim MA, Alnashef IM (2012) Generation of superoxide ion in pyridinium, morpholinium, ammonium, and sulfonium-based ionic liquids and the application in the destruction of toxic chlorinated phenols. Ind Eng Chem Res 51:10546–10556
Ibrahim MH, Hayyan M, Hashim MA, Hayyan A, Hadj-Kali MK (2016) Physicochemical properties of piperidinium, ammonium, pyrrolidinium and morpholinium cations based ionic liquids paired with bis(trifluoromethylsulfonyl)imide anion. Fluid Phase Equilib 427:18–26
Kamboj R, Bharmoria P, Chauhan V, Singh S, Kumar A, Mithu VS, Kang TS (2014) Micellization behavior of morpholinium-based amide-functionalized ionic liquids in aqueous media. Langmuir 30:9920–9930
Kim HT, Hong YK, Kang JW, Lee YW, Kim KS (2012) Thermal and electrochemical stability of morpholinium ionic liquids. Korean Chem Eng Res 50:702–707
Dhakal P, Weise AR, Fritsch MC, O’Dell CM, Paluch AS (2020) Expanding the solubility parameter method MOSCED to pyridinium-, quinolinium-, pyrrolidinium-, piperidinium-, bicyclic-, morpholinium-, ammonium-, phosphonium-, and sulfonium-based ionic liquids. ACS Omega 5:3863–3877
Królikowska M, Zawadzki M (2017) Transport properties and thermodynamic characterization of aqueous solutions of morpholinium-based ionic liquids. J Mol Liq 251:358–368
Lee W, Shin JY, Kim KS, Kang SP (2016) Kinetic promotion and inhibition of methane hydrate formation by morpholinium ionic liquids with chloride and tetrafluoroborate anions. Energy Fuel 30:3879–3885
Marcinkowski U, Kloskowski A, Warmińska D (2018) Solvation of ionic liquids based on N-methyl-N- alkylmorpholinium cations in N,N -dimethylformamide and N,N-dimethylacetamide-volumetric and compressibility studies. J Chem Thermodyn 119:92–101
Marcinkowski U, Olszewska T, Kloskowski A, Warmińska D (2014) Apparent molar volumes and expansivities of ionicliquids based on N-alkyl-N-methylmorpholinium cations in acetonitrile. J Chem Eng Data 59:718–725
Marcinkowski U, Szepiński E, Kloskowski A, NamieaNik J, Warmińska D (2017) Solvation of ionic liquids based on N-alkyl-N-methylmorpholinium cations in N,N-dimethylformamide and dimethyl sulfoxide-A volumetric and acoustic study. J Chem Thermodyn 104:91–101
Park BH, Hyeon SE, Cha JH, Hong YK, Kang JW, Kim KS (2016) Copper nanoparticles stabilized by morpholinium ionic liquids. J Nanosci Nanotechnol 16:11005–11008
Pezeshki M, Ghatee MH (2018) Properties investigation of protic morpholinium-based ionic liquids by classical molecular dynamics simulation and quantum chemical calculations. J Mol Liq 272:554–564
Salchner R, Laus G, Haslinger S (2019) One-pot sequential synthesis of 2-amino-4, 6-diaryl pyrimidines involving SO3H− functionalized piperazinium-based dicationic ionic liquids as homogeneous catalysts. ChemistrySelect 4:8751–8756
Ma C, Shukla SK, Samikannu R, Mikkola JP, Ji X (2020) CO2 separation by a series of aqueous morpholinium-based ionic liquids with acetate anions. ACS Sustain Chem Eng 8:415–426
Salchner R, Laus G, Haslinger S, Kahlenberg V, Wurst K, Braun DE, Vergeiner S, Kopacka H, Schottenberger H, Puckowski A, Markiewicz M, Stolte S, Nerdinger S (2015) Structural and ecotoxicological profile of N-alkoxymorpholinium-based ionic liquids. Heterocycles 90:1018–1037
Kahani S, Shafiei M, Abdolmaleki A, Karimi K (2017) Enhancement of ethanol production by novel morpholinium ionic liquids. J Clean Prod 168:952–962
Goossens K, Lava K, Bielawski CW, Binnemans K (2016) Ionic liquid crystals: versatile materials. Chem Rev 116:4643–4807
Yoshida T, Kawai A, Khara DC, Samanta A (2015) Temporal behavior of the singlet molecular oxygen emission in imidazolium and morpholinium ionic liquids and its implications. J Phys Chem B 119:6696–6702
Yu J, Zhang S, Dai Y, Lu X, Lei Q, Fang W (2016) Antimicrobial activity and cytotoxicity of piperazinium- and guanidinium-based ionic liquids. J Hazard Mater 307:73–81
Yuan Y, Wang TY, Kun W, Li L, Dai Y (2012) Convenient synthesis and application of novel bi-SO3H-functionalized ionic liquids based on piperazinium. Chin Chem Lett 23:1031–1034
Yue C (2010) Aromatic compounds Mannich reaction using economical acidic ionic liquids based on morpholinium salts as dual solvent-catalysts. Synth Commun 40:3640–3647
Marciniak A (2012) Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate. J Chem Thermodyn 49:137–145
Cha JH, Kim KS, Choi S, Yeon SH, Lee H, Lee CS, Shim JJ (2007) Size-controlled electrochemical synthesis of palladium nanoparticles using morpholinium ionic liquid. Korean J Chem Eng 24:1089–1094
Khalafi-Nezhad A, Panahi F (2014) Size-controlled synthesis of palladium nanoparticles on a silica–cyclodextrin substrate: a novel palladium catalyst system for the Heck reaction in water. ACS Sustain Chem Eng 2:1177–1186
Khalafi-Nezhad A, Panahi F (2011) Immobilized palladium nanoparticles on a silica–starch substrate (PNP–SSS): as an efficient heterogeneous catalyst for heck and copper-free Sonogashira reactions in water. Green Chem 13:2408–2415
Yeon SH, Kim KS, Choi S, Cha JH, Lee H, Oh J, Lee BB (2006) Poly(vinylidenefluoride)-hexafluoropropylene gel electrolytes based on N-(2-hydroxyethyl)-N-methyl morpholinium ionic liquids. Korean J Chem Eng 23:940–947
Yu W, Peng H, Zhang H, Zhou X (2009) Synthesis and mesophase behaviour of morpholinium ionic liquid crystals. Chin J Chem 27:1471–1475
Yeon SH, Kim KS, Choi S, Lee H, Kim HS, Kim H (2005) Physical and electrochemical properties of 1-(2-hydroxyethyl)-3-methyl imidazolium and N-(2-hydroxyethyl)-N-methyl morpholinium ionic liquids. Electrochim Acta 50:5399–5407
Ster D, Baumeister U, Chao JL, Tschierskea C, Israel G (2007) Synthesis and mesophase behaviour of ionic liquid crystals. J Mater Chem 17:3393–3400
Pezeshki M, Ghatee MH (2018) Properties investigation of protic morpholinium-based ionic liquids by molecular dynamics simulation and quantum chemical calculations. J Mol Liq 272:554–564
Cheng X, Su F, Huang R, Gao H, Prehm M, Tschierske C (2012) Effect of central linkages on mesophase behavior of imidazolium-based rod-like ionic liquid crystals. Soft Matter 8:2274–2285
Batra D, Seifert S, Firestone MA (2007) The effect of cation structure on the mesophase architecture of self-assembled and polymerized imidazolium-based ionic liquids. Macromol Chem Phys 208:1416–1427
Choi S, Kim KS, Lee H, Oh JS, Lee BB (2005) Synthesis and ionic conductivities of lithium-doped morpholinium salt. Korean J Chem Eng 22:281–284
Kim KS, Park SY, Yeon SH, Lee H (2005) N-Butyl-N-methylmorpholinium bis(trifluoromethanesulfonyl) imide–PVdF(HFP) gel electrolytes. Electrochim Acta 50:5673–5678
GarcÃa G, Atilhan M, Aparicio S (2015) Theoretical study on the solvation of C60 fullerene by ionic liquids II: DFT analysis of the interaction mechanism. J Phys Chem B 119:10616–10629
Lu X, Yue L, Hu M, Cao Q, Xu L, Guo Y, Hu S, Fang W (2014) Piperazinium-based ionic liquids with lactate anion for extractive desulfurization of fuels. Energy Fuel 28:1774–1780
Wang Y, Zhou J, Liu K, Dai L (2013) Novel bi-SO3H-functionalized ionic liquids based on piperazinium: highly efficient and recyclable catalysts for the synthesis of β-acetamido ketones. J Mol Catal A Chem 366:195–201
Ullah Z, Bustam MA, Man Z, Muhammad N, Khan AS (2015) Synthesis, characterization and the effect of temperature on different physicochemical properties of protic ionic liquids. RSC Adv 5:71449–71461
Habibi D, Shamsian A (2014) An efficient and recyclable bifunctional acid-base ionic liquid for synthesis of 1H-indazolo[1,2-b]phthalazinetriones. Res Chem Intermed 41:6245–6255
Gavaskar D, Suresh BAR, Raghunathan R, Dharani M, Balasubramanian S (2014) Ionic liquid accelerated multicomponent sequential assembly of ferrocene grafted spiro-heterocycles. J Organomet Chem 768:128–135
Lu X, Cao Q, Wu X, Xie H, Lei Q, Fang W (2014) Conformational isomerism influence on the properties of piperazinium bis(trifluoromethylsulfonyl)imide. J Phys Chem B 118:9085–9095
Yu J, Zhang S, Dai Y, Lu X, Lei Q, Fang W (2016) Antimicrobial activity and cytotoxicity of piperazinium- andguanidinium-based ionic liquids. J Hazard Mater 307:73–81
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Section Editor information
Rights and permissions
Copyright information
© 2021 Springer Nature Singapore Pte Ltd.
About this entry
Cite this entry
Li, J.R., Hu, Y.L. (2021). Morpholinium Ionic Liquids and Piperazinium Ionic Liquids. In: Zhang, S. (eds) Encyclopedia of Ionic Liquids. Springer, Singapore. https://doi.org/10.1007/978-981-10-6739-6_120-1
Download citation
DOI: https://doi.org/10.1007/978-981-10-6739-6_120-1
Received:
Accepted:
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-10-6739-6
Online ISBN: 978-981-10-6739-6
eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics