Methods for measuring vaporization enthalpies of ionic liquids

doi:10.11949/0438-1157.20191240

Abstract

Abstract:

Due to their characteristics, such as low vapor pressure, low volatilization, strong electrical conductivity, stable chemical properties, recyclability and so on, ionic liquids (ILs) can replace organic solvents as a new environmentally friendly solvent, can be used as a catalyst to catalyze chemical reactions, can participate in electrochemical reactions as electrolyte solutions, can make new batteries and so on. It is generally believed that ILs are not volatile and their vaporization enthalpies cannot be measured. However, in recent years, the related research results of ILs have been reviewed, and it has been found that researchers have successively proposed many methods for obtaining vaporization enthalpies of ILs. We will systematically introduce these methods, expounding their principles, and laying a solid foundation for future research.

Key words: measurement, vaporization, ionic liquids, enthalpy, thermodynamics

摘要：

离子液体具有蒸气压低、不易挥发、导电能力强、化学性质稳定、可循环利用等特点，具有以下作用：能够替代有机溶剂作为绿色环保的新型溶剂；可以作为催化剂催化化学反应；可以作为电解质溶液参与电化学反应，制作新型电池；可以作为吸附气体的吸附剂等。过去人们认为离子液体不挥发，也不能测量它们的汽化焓，回顾了近年来离子液体的相关研究成果，发现陆续有研究者提出测量离子液体汽化焓的方法，鉴于目前缺少相关总结工作，将系统性地介绍这些方法并阐述其原理，为今后的离子液体研究提供指导。

关键词: 测量, 汽化, 离子液体, 焓, 热力学

CLC Number:

O 64

Sijie SONG,Jia YAO,Haoran LI. Methods for measuring vaporization enthalpies of ionic liquids[J]. CIESC Journal, 2020, 71(1): 26-33.

宋思婕,姚加,李浩然. 离子液体汽化焓的测量方法[J]. 化工学报, 2020, 71(1): 26-33.

Figures/Tables 1

References 73

1	Welton T. Room-temperature ionic liquids. solvents for synthesis and catalysis[J]. Chemical Reviews, 1999, 99(8): 2071-2084.
2	Galiński M, Lewandowski A, Stępniak I. Ionic liquids as electrolytes[J]. Electrochimica Acta, 2006, 51(26): 5567-5580.
3	Hallett J P, Welton T. Room-temperature ionic liquids: solvents for synthesis and catalysis[J]. Chemical Reviews, 2011, 111(5): 3508-3576.
4	Zhang P F, Gong Y T, Lv Y Q, et al. Ionic liquids with metal chelate anions[J]. Chemical Communications, 2012, 48(17): 2334-2336.
5	Itoh T, Han S, Matsushita Y, et al. Enhanced enantioselectivity and remarkable acceleration on the lipase-catalyzed transesterification using novel ionic liquids[J]. Green Chemistry, 2004, 6(9): 437-439.
6	Di J, Xia J X, Yin S, et al. One-pot solvothermal synthesis of Cu-modified BiOCl via a Cu-containing ionic liquid and its visible-light photocatalytic properties[J]. RSC Advances, 2014, 4(27): 14281-14290.
7	Huang C P, Liu Z C, Xu C M, et al. Effects of additives on the properties of chloroaluminate ionic liquids catalyst for alkylation of isobutane and butane[J]. Applied Catalysis A: General, 2004, 277(1/2): 41-43.
8	Yin S, Di J, Li M, Sun Y L, et al. Ionic liquid-assisted synthesis and improved photocatalytic activity of p-n junction g-C₃N₄/BiOCl[J]. Journal of Materials Science, 2016, 51(10): 4769-4777.
9	Chiappe C, Pieraccini D. Ionic liquids: solvent properties and organic reactivity[J]. Journal of Physical Organic Chemistry, 2005, 18(4): 275-297.
10	Park J W, Yamauchi K, Takashima E, et al. Solvent effect of room temperature ionic liquids on electrochemical reactions in lithium-sulfur batteries[J]. The Journal of Physical Chemistry C, 2013, 117(9): 4431-4440.
11	Khachatryan K S, Smirnova S V, Torocheshnikova I I, et al. Solvent extraction and extraction–voltammetric determination of phenols using room temperature ionic liquid[J]. Analytical and Bioanalytical Chemistry, 2005, 381(2): 464-470.
12	Parajó J J, Macário I P E, Gaetano Y D, et al. Glycine-betaine-derived ionic liquids: synthesis, characterization and ecotoxicological evaluation[J]. Ecotoxicology and Environmental Safety, 2019, 184: 109580.
13	Wang H Z, Lu Q M, Ye C F, et al. Friction and wear behaviors of ionic liquid of alkylimidazolium hexafluorophosphates as lubricants for steel/steel contact[J]. Wear, 2004, 256(1/2): 44-48.
14	Qu J, Truhan J J, Dai S, et al. Ionic liquids with ammonium cations as lubricants or additives[J]. Tribology Letters, 2006, 22(3): 207-214.
15	Jiménez A E, Bermúdez M D, Carrión F J, et al. Room temperature ionic liquids as lubricant additives in steel–aluminium contacts: influence of sliding velocity, normal load and temperature[J]. Wear, 2006, 261(3/4): 347-359.
16	Armand M, Endres F, Douglas R M, et al. Ionic-liquid materials for the electrochemical challenges of the future[J]. Nature Materials, 2009, 8(8): 621-629.
17	Lewandowski A, Swiderska-Mocek A. Ionic liquids as electrolytes for Li-ion batteries—an overview of electrochemical studies[J]. Journal of Power Sources, 2009, 194(1): 601-609.
18	Zakeeruddin S M, Gratzel M. Solvent-free ionic liquid electrolytes for mesoscopic dye-sensitized solar cells[J]. Advanced Functional Materials, 2009, 19(14): 2187-2202.
19	Kim T Y, Lee H W, Stoller M, et al. High-performance supercapacitors based on poly(ionic liquid)-modified graphene electrodes[J]. ACS Nano, 2011, 5(1): 436-442.
20	Zhang Y Q, Zhang S J, Lu X M, et al. Dual amino-functionalised phosphonium ionic liquids for CO₂ capture[J]. Chemistry-A European Journal, 2009, 15(12): 3003-3011.
21	Hice S A, Clark K D, Anderson J L, et al. Capture, concentration, and detection of salmonella in foods using magnetic ionic liquids and recombinase polymerase amplification[J]. Analytical Chemistry, 2019, 91(1): 1113-1120.
22	Palomar J, Lemus J, Gilarranz M A, et al. Adsorption of ionic liquids from aqueous effluents by activated carbon[J]. Carbon, 2009, 47(7): 1846-1856.
23	Bates E D, Mayton R D, Ntai I, et al. CO₂ capture by a task-specific ionic liquid[J]. Journal of the American Chemical Society, 2002, 124(6): 926-927.
24	MacDowell N, Florin N, Buchard A, et al. An overview of CO₂ capture technologies[J]. Energy & Environmental Science, 2010, 3(11): 1645-1669.
25	Yu C H, Huang C H, Tan C S. A review of CO₂ capture by absorption and adsorption[J]. Aerosol and Air Quality Research, 2012, 12(5): 745-769.
26	Zhang Q H, Zhang S G, Deng Y Q. Recent advances in ionic liquid catalysis[J]. Green Chemistry, 2011, 13(10): 2619.
27	Giernoth R. Task-specific ionic liquids[J]. Angewandte Chemie-International Edition, 2010, 49(16): 2834-2839.
28	Walden P. Ueber die molekulargrösse und elektrische leitfähigkeit einiger geschmolzenen salze[J]. Bulletin de l'Académie Impériale des Sciences de St.-Pétersbourg, 1914, 8(6): 405-422.
29	Hurley F H, Weir T P. Electrodeposition of metals from fused quaternary ammonium salts[J]. Journal of the Electrochemical Society, 1951, 98(5): 203-206.
30	Gale R J, Gilbert B, Osteryoung R A. Raman spectra of molten aluminum chloride: 1-butylpyridinium chloride systems at ambient temperatures[J]. Inorganic Chemistry, 1978, 17(10): 2728-2729.
31	Olivier-Bourbigou H, Magna L, Morvan D. Ionic liquids and catalysis: recent progress from knowledge to applications[J]. Applied Catalysis A: General, 2010, 373(1/2):1-56.
32	Earle M J, Esperança J M S S, Gilea M A, et al. The distillation and volatility of ionic liquids[J]. Nature, 2006, 439(7078): 831-834.
33	Seddon K R. Room-temperature ionic liquids—neoteric solvents for clean catalysis[J]. Kinetics and Catalysis, 1996, 37(5): 693-697.
34	Seddon K R. In molten salt forum[C]//Proceedings of 5th International Conference on Molten Salt Chemistry and Technology. Zürich: Trans Tech Publications, 1998: 52-62.
35	Paulechka Y U, Kabo G J, Blokhin A V, et al. Thermodynamic properties of 1-butyl-3-methylimidazolium hexafluorophosphate in the ideal gas state[J]. Journal of Chemical & Engineering Data, 2003, 48(3): 457-462.
36	Rebelo L P N, Lopes J N C, Esperança J M S S, et al. On the critical temperature, normal boiling point, and vapor pressure of ionic liquids[J]. The Journal of Physical Chemistry B, 2005, 109(13): 6040-6043.
37	Paulechka Y U, Zaitsau D H, Kabo G J, et al. Vapor pressure and thermal stability of ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide[J]. Thermochimica Acta, 2005, 439: 158-160.
38	Ipser H. Vapor pressure methods: a source of experimental thermodynamic data[J]. Berichte der Bunsengesellschaft für physikalische Chemie, 1998, 102(9): 1217-1224.
39	Zaitsau D H, Verevkin S P, Paulechka Y U, et al. Comprehensive study of vapor pressures and enthalpies of vaporization of cyclohexyl esters[J]. Journal of Chemical & Engineering Data, 2003, 48(6): 1393.
40	Zaitsau D H, Kabo G J, Strechan A A, et al. Experimental vapor pressures of 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides and a correlation scheme for estimation of vaporization enthalpies of ionic liquids[J]. The Journal of Physical Chemistry A, 2006, 110(22): 7303-7306.
41	Adedeji F A, Lalage D, Brown S, et al. Thermochemistry of arene chromium tricarbonyls and the strenghts of arene-chromium bonds[J]. Journal of Organometallic Chemistry, 1975, 97(2): 221-228.
42	Santos L M N B F, Schröder B, Fernandes O O P, et al. Measurement of enthalpies of sublimation by drop method in a calvet type calorimeter: design and test of a new system[J]. Thermochimica Acta, 2004, 415: 15-20.
43	Santos L M N B F, Lopes J N C, Coutinho J A P, et al. Ionic liquids: first direct determination of their cohesive energy[J]. Journal of the American Chemical Society, 2007, 129(1): 284-285.
44	Armstrong J P, Hurst C, Jones R G, et al. Vapourisation of ionic liquids[J]. Physical Chemistry Chemical Physics, 2007, 9(8): 982-990.
45	Deyko A, Lovelock K R J, Corfield J A, et al. Measuring and predicting ∆_vapH₂₉₈ values of ionic liquids[J]. Physical Chemistry Chemical Physics, 2009, 11(38): 8544-8555.
46	Lovelock K R J, Deyko A, Licence P, et al. Vaporisation of an ionic liquid near room temperature[J]. Physical Chemistry Chemical Physics, 2010, 12(31): 8893-8901.
47	Chatterjee K, Dollimore D, Alexander K S. Calculation of vapor pressure curves for hydroxybenzoic acid derivatives using thermogravimetry[J]. Thermochimica Acta, 2002, 392/393: 107-117.
48	Luo H M, Baker G A, Dai S. Isothermogravimetric determination of the enthalpies of vaporization of 1-alkyl-3-methylimidazolium ionic liquids[J]. The Journal of Physical Chemistry B, 2008, 112(33): 10077-10081.
49	Chatterjee K, Hazra A, Dollimore D, et al. Estimating vapor pressure curves by thermogravimetry: a rapid and convenient method for characterization of pharmaceuticals[J]. European Journal of Pharmaceutics and Biopharmaceutics, 2002, 54(2): 171-180.
50	Dai S, Toth L M, Cul G D D, et al. Ultraviolet-visible absorption spectrum of C₆₀ vapor and determination of the C₆₀ vaporization enthalpy[J]. Journal of Chemical Physics, 1994, 101(5): 4470-4471.
51	Dai S. Correct regression formula used in determination of vaporization enthalpy of pure liquids by UV-visible spectroscopy[J]. Journal of Chemical Education, 1996, 73(2): 122.
52	Verevkin S P, Ralys R V, Zaitsau D H, et al. Express thermo-gravimetric method for the vaporization enthalpies appraisal for very low volatile molecular and ionic compounds[J]. Thermochim. Acta, 2012, 538: 55-62.
53	Wang C M, Luo H M, Li H R, et al. Direct UV-spectroscopic measurement of selected ionic-liquid vapors[J]. Physical Chemistry Chemical Physics, 2010, 12(26): 7246-7250.
54	Verevkin S P, Zaitsau D H, EmeÌlyanenko V N, et al. A new method for the determination of vaporization enthalpies of ionic liquids at low temperatures[J]. The Journal of Physical Chemistry B, 2011, 115(44): 12889-12895.
55	Grate J W. Acoustic wave microsensor arrays for vapor sensing[J]. Chemical Reviews, 2000, 100(7): 2627-2748.
56	Sauerbrey G Z. Verwendung von schwingquarzen zur wägung dünner schichten und zur mikrowägung[J]. Zeitschrift für Physik, 1959, 155(2): 206-222.
57	Bruckenstein S, Shay M. Experimental aspects of use of the quartz crystal microbalance in solution[J]. Electrochimica Acta, 1985, 30(10): 1295-1300.
58	Kanasawa K K, Gordon J G. Frequency of a quartz microbalance in contact with liquid[J]. Analytical Chemistry, 1985, 57(8): 1770-1771.
59	Klavetter E A, Martin S J, Wessendorf K O. Monitoring jet fuel thermal stability using a quartz crystal microbalance[J]. Energy Fuels, 1993, 7(5): 582-588.
60	Tsionsky V, Daikhin L, Urbakh M, et al. Behavior of quartz cystal microbalance in nonadsorbed gases at high pressures[J]. Langmuir, 1995, 11(2): 674-678.
61	Mecea V M. Fundamentals of mass measurements[J]. Journal of Thermal Analysis and Calorimetry, 2006, 86(1): 9-16.
62	Johannsmann D. Viscoelastic, mechanical, and dielectric measurements on complex samples with the quartz crystal microbalance[J]. Physical Chemistry Chemical Physics, 2008, 10(31): 4516-4534.
63	Liang C, Yuan C Y, Warmack R J, et al. Ionic liquids: a new class of sensing materials for detection of organic vapors based on the use of a quartz crystal microbalance[J]. Analytical Chemistry, 2002, 74(9): 2172-2176.
64	Ma H, He J, Zhu Z, et al. A quartz crystal microbalance-based molecular ruler for biopolymers[J]. Chemical Communications, 2010, 46(6): 949-951.
65	Verevkin S P, Ralys R V, Emel yanenko V N, et al. Thermochemistry of the pyridinium- and pyrrolidinium-based ionic liquids[J]. Journal of Thermal Analysis and Calorimetry, 2013, 112(1): 353-358.
66	Verevkin S P, Emelyanenko V N, Zaitsau D Z, et al. Ionic liquids: differential scanning calorimetry as a new indirect method for determination of vaporization enthalpies[J]. The Journal of Physical Chemistry B, 2012, 116(14): 4276-4285.
67	Paulechka Y U. Heat capacity of room-temperature ionic liquids: a critical review[J]. Journal of Physical and Chemical Reference Data, 2010, 39(3): 33108-33123.
68	Tong J, Liu Q S, Zhang P, et al. Surface tension and density of 1-methyl-3-hexylimidazolium chloroindium[J]. Journal of Chemical and Engineering Data, 2007, 52(4): 1497-1500.
69	Tong J, Liu Q S, Kong Y X, et al. Physicochemical properties of an ionic liquid [C₂mim][B(CN)₄][J]. Journal of Chemical and Engineering Data, 2010, 55(9): 3693-696.
70	Wei H D, Wang Y T, Yao J, et al. Empirical study of physicochemical and spectral properties of Cu^II-containing chelate-based ionic liquids[J]. Physical Chemistry Chemical Physics, 2018, 20(6): 4109-4117.
71	Verevkin S P. Predicting enthalpy of vaporization of ionic liquids: a simple rule for a complex property[J]. Angewandte Chemie-International Edition, 2008, 47(27): 5071-5074.
72	Zaitsau D H, Fumino K, Emel yanenko V N, et al. Structure–property relationships in ionic liquids: a study of the anion dependence in vaporization enthalpies of imidazolium-based ionic liquids[J]. ChemPhysChem, 2012, 13(7): 1868-1876.
73	Slattery J M, Daguenet C, Dyson P J, et al. How to predict the physical properties of ionic liquids: a volume-based approach schubert[J]. Angewandte Chemie-International Edition, 2007, 119(28): 5480-5484.

ILs	T/K	?_vapH_T^①/(kJ·mol^-1)	?_vapH₂₉₈^②/( kJ·mol^-1)	方法	Ref.
[C₂min][Tf₂N]	463.0	118.8±1.3	135.3±1.3	Knudsen	[40]
	577.8	110.4±2.4	136±6	VVDM	[43]
	430.0	118±2	134±2	MS	[44]
	495.5	120.6±2.1		TGA	[48]
	573.0	111.7±1.7		UV	[53]
	378.2	118.6±1.0	126.6±1.0	QCM	[54]
				DSC	[65]
			136.1	surface tension	[40]
[C₄mim][Tf₂N]	477.6	118.3±1.7	136.2±1.7	Knudsen	[40]
	577.0	128.4±3.0	155±6	VVDM	[43]
	440.0	117±3	134±3	MS	[44]
	495.5	118.5±0.4		TGA	[48]
	553.0	114.1±1.6		UV	[53]
				QCM	[54]
				DSC	[65]
			134.6	surface tension	[40]

ILs	T/K	?_vapH_T^①/(kJ·mol^-1)	?_vapH₂₉₈^②/( kJ·mol^-1)	方法	Ref.
[C₂min][Tf₂N]	463.0	118.8±1.3	135.3±1.3	Knudsen	[40]
	577.8	110.4±2.4	136±6	VVDM	[43]
	430.0	118±2	134±2	MS	[44]
	495.5	120.6±2.1		TGA	[48]
	573.0	111.7±1.7		UV	[53]
	378.2	118.6±1.0	126.6±1.0	QCM	[54]
				DSC	[65]
			136.1	surface tension	[40]
[C₄mim][Tf₂N]	477.6	118.3±1.7	136.2±1.7	Knudsen	[40]
	577.0	128.4±3.0	155±6	VVDM	[43]
	440.0	117±3	134±3	MS	[44]
	495.5	118.5±0.4		TGA	[48]
	553.0	114.1±1.6		UV	[53]
				QCM	[54]
				DSC	[65]
			134.6	surface tension	[40]

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