Syntheses and Properties of Novel Boron-Containing Ionic Liquids 1-Alkyl-3-methylimidazolium Benzyoltrifluoroborates

doi:10.11944/j.issn.1000-0518.2019.10.190163

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (10): 1186-1193.DOI: 10.11944/j.issn.1000-0518.2019.10.190163

• Full Papers • Previous Articles Next Articles

Syntheses and Properties of Novel Boron-Containing Ionic Liquids 1-Alkyl-3-methylimidazolium Benzyoltrifluoroborates

GUO Yijiang,CHEN Qingde(),SHEN Xinghai()

Beijing National Laboratory for Molecular Sciences,Fundamental Science on Radiochemistry and Radiation Chemistry Laboratory, Center for Applied Physics and Technology,College of Chemistry and Molecular Engineering,Peking University,Beijing 100871,China

Received:2019-06-04 Accepted:2019-08-29 Published:2019-10-01 Online:2019-09-29
Contact: CHEN Qingde,SHEN Xinghai
Supported by:
Supported by the National Natural Science Foundation of China(No.U1830202, No.U1507203)

Abstract

Abstract:

Three novel boron-containing ionic liquids(ILs), 1-alkyl-3-methylimidazolium benzyoltrifluoroborates([C_nmim][BTB], n=4, 6, 8), were successfully synthesized and some of their physico-chemical properties were characterized by nuclear magnetic resonance(NMR), differential scanning calorimeter(DSC), and thermogravimetric analysis(TGA). It was found that their decomposition temperatures were around 200 ℃. With the increase of the length of carbon chain on the imidazolium ring, the melting temperature, viscosity and hydrophobicity gradually increased. [C₄mim][BTB] was hydrophilic, while [C₆mim][BTB] and [C₈mim][BTB] were hydrophobic. In particular, the later two were more stable when they mixed with water for a long time. In other words, the shortcoming of tetrafluoroborate ILs(i.e., strong hydrophilicity, especially the easy hydrolysis of $BF^{-}_{4}$) was overcome to great extent. Thus, it is hopeful for the two ILs to be used in the field of spent fuel reprocessing, which will effectively impove the critical safety.

Key words: boron-containing ionic liquid(s), benzyoltrifluoroborate, hydrophobicity, stability

GUO Yijiang, CHEN Qingde, SHEN Xinghai. Syntheses and Properties of Novel Boron-Containing Ionic Liquids 1-Alkyl-3-methylimidazolium Benzyoltrifluoroborates[J]. Chinese Journal of Applied Chemistry, 2019, 36(10): 1186-1193.

References

[1]	Han X,Armstrong D W.Ionic Liquids in Separations[J]. Acc Chem Res,2007,40(11):1079-1086.
[2]	LIU Haiwang,YANG Tao,CHEN Qingde,et al. Extraction Behaviors of Ionic Liquid Systems and Application Perspectives in Reprocessing of Spent Nuclear Fuel[J]. J Nucl Radiochem,2015,37(5):287-309(in Chinese). 刘海望,杨涛,陈庆德,等. 离子液体体系的萃取行为及其在乏燃料后处理中的应用前景[J]. 核化学与放射化学,2015,37(5):287-309.
[3]	Sun X Q,Luo H M,Dai S.Ionic Liquids-Based Extraction:A Promising Strategy for the Advanced Nuclear Fuel Cycle[J]. Chem Rev,2012,112(4):2100-2128.
[4]	Harmon C D,Smith W H,Costa D A.Criticality Calculations for Plutonium Metal at Room Temperature in Ionic Liquid Solutions[J]. Radiat Phys Chem,2001,60(3):157-159.
[5]	Welton T.Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis[J]. Chem Rev,1999,99(99):2071-2083.
[6]	Freire M G,Neves C,Marrucho I M,et al. Hydrolysis of Tetrafluoroborate and Hexafluorophosphate Counter Ions in Imidazolium-Based Ionic Liquids[J]. J Phys Chem A,2010,114(11):3744-3749.
[7]	Zhou Z B,Matsumoto H,Tatsumi K. Low-Viscous, Low-Melting, Hydrophobic Ionic Liquids:1-Alkyl-3-Methylimidazolium Trifluoromethyltrifluoroborate[J]. Chem Lett,2004,33(6):680-681.
[8]	Zhou Z B,Matsumoto H,Tatsumi K.Structure and Properties of New Ionic Liquids Based on Alkyl- and Alkenyltrifluoroborates[J]. ChemPhysChem,2005,6(7):1324-1332.
[9]	Nishi N,Imakura S,Kakiuchi T.Wide Electrochemical Window at the Interface Between Water and a Hydrophobic Room-Temperature Ionic Liquid of Tetrakis[3,5-Bis(Trifluoromethyl)Phenyl]-Borate[J]. Anal Chem,2006,78:2726-2731.
[10]	Zhou Z B,Matsumoto H,Tatsumi K.Cyclic Quaternary Ammonium Ionic Liquids with Perfluoroalkyltrifluoroborates:Synthesis, Characterization, and Properties[J]. Chem Commun,2006,12(8):2196-2201.
[11]	Nishi N,Suzuki A,Kakiuchi T.Hydrophobic Ionic Liquids Composed of Perfluoroalkyltrifluoroborates for Ionic Liquid-Water Two-Phase Systems[J]. Bull Chem Soc Jpn,2009,82(1):86-92.
[12]	Shakourian-Fard M,Jamshidi Z,Bayat A,et al. Structural and Electronic Properties of Alkyl-Trifluoroborate Based Ionic Liquids:A Theoretical Study[J]. J Fluor Chem,2013,153:96-100.
[13]	Iwasaki K,Yoshii K,Tsuda T,et al. Physicochemical Properties of Phenyltrifluoroborate-Based Room Temperature Ionic Liquids[J]. J Mol Liq,2017,246:236-243.
[14]	Prikhod'ko S A,Shabalin A Y,Bardin V V,et al. 1-Alkyl-3-Methylimidazolium 4-Organyloxy-2,3,5,6-Tetrafluorophenyltrifluoroborates as a New Platform for Ionic Liquids with Specific Properties[J]. RSC Adv,2017,7(28):17497-17504.
[15]	Johannes L,Jan A P,Philipp T H,et al. Perfluoroalkyltricyanoborate and Perfluoroalkylcyanofluoroborate Anions-Building Blocks for Low-Viscosity Ionic Liquids[J]. Chem Eur J,2018,23:608-624.
[16]	Kuang D,Wang P,Ito S,et al. Stable Mesoscopic Dye-Sensitized Solar Cells Based on Tetracyanoborate Ionic Liquid Electrolyte[J]. J Am Chem Soc,2006,128(24):7732-7733.
[17]	Pandey G P,Hashmi S A.Ionic Liquid 1-Ethyl-3-Methylimidazolium Tetracyanoborate-Based Gel Polymer Electrolyte for Electrochemical Capacitors[J]. J Mater Chem A,2013,1(10):3372-3378.
[18]	Bischoff L A,Drisch M,Kerpen C,et al. Cyanohydridoborate Anions:Synthesis, Salts, and Low-Viscosity Ionic Liquids[J]. Chem Eur J,2019,25(14):3560-3574.
[19]	Yamashita M,Suzuki Y,Segawa Y,et al. Synthesis, Structure of Borylmagnesium, and Its Reaction with Benzaldehyde to Form Benzoylborane[J]. J Am Chem Soc,2007,129(31):9570-9575.
[20]	Molander G A,Raushel J,Ellis N M.Synthesis of an Acyltrifluoroborate and Its Fusion with Aides to Form Amides[J]. J Org Chem,2010,75(12):4304-4306.
[21]	Curran D P,Solovyev A,Brahmi M M,et al. Synthesis and Reactions of N-Heterocyclic Carbene Boranes[J]. Angew Chem Int Ed,2011,50(44):10294-10317.
[22]	Molander G A,Cavalcanti L N.Metal-Free Chlorodeboronation of Organotrifluoroborates[J]. J Org Chem,2011,76(17):7195-7203.
[23]	Dumas A M,Molander G A,Bode J W.Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water[J]. Angw Chem Int Ed,2012,51(23):5683-5686.
[24]	He Z,Trinchera P,Adachi S,et al. Oxidative Geminal Functionalization of Organoboron Compounds[J]. Angew Chem Int Ed,2012,51(44):11092-11096.
[25]	Eros G,Kushida Y,Bode J W.A Reagent for the One-Step Preparation of Potassium Acyltrifluoroborates(KATs) from Aryl- and Heteroarylhalides[J]. Angew Chem Int Ed,2014,53(29):7604-7607.
[26]	Liu S Z M,Wu D N,Bode J W. One-Step Synthesis of Aliphatic Potassium Acyltrifluoroborates(KATs) from Organocuprates[J]. Org Lett,2018,20(8):2378-2381.
[27]	Lobo Ferreira A I M C,Rodrigues A S M C,Villas M,et al. Crystallization and Glass-Forming Ability of Ionic Liquids:Novel Insights into Their Thermal Behavior[J]. ACS Sustainable Chem Eng,2019,7(3):2989-2997.
[28]	Toh S L I,McFarlane J,Tsouris C,et al. Room-Temperature Ionic Liquids in Liquid-Liquid Extraction:Effects of Solubility in Aqueous Solutions on Surface Properties[J]. Solvent Extr Ion Exch,2006,24(1):33-56.
[29]	Zhou Z B,Matsumoto H,Tatsumi K. Low-Melting, Low-Viscous, Hhydrophobic Ionic Liquids:1-Alkyl(Alkyl Ether)-3-Methylimidazolium Perfluoroalkyltrifluoroborate[J]. Chem Eur J,2004,10(24):6581-6591.
[30]	Froba A P,Kremer H,Leipertz A. Density, Refractive Index, Interfacial Tension, and Viscosity of Ionic Liquids [EMIM][EtSO4], [EMIM][NTf2], [EMIM][N(CN)2], and [OMA][NTf2] in Dependence on Temperature at Atmospheric Pressure[J]. J Phys Chem B,2008,112(39):12420-12430.
[31]	Huddleston J G,Visser A E,Reichert W M,et al. Characterization and Comparison of Hydrophilic and Hydrophobic Room Temperature Ionic Liquids Incorporating the Imidazolium Cation[J]. Green Chem,2001,3(4):156-164.
[32]	ZHENG Qige,LIU Hui,XIA Quan,et al. Density, Dynamic Viscosity and Electrical Conductivity of Two Hydrophobic Phosphonium Ionic Liquids[J]. Acta Phys Chim Sin,2017,33(4):736-744(in Chinese). 郑其格,刘慧,夏泉,等. 两种疏水型膦类离子液体的密度、动力粘度及电导率[J]. 物理化学学报,2017,33(4):736-744.

Syntheses and Properties of Novel Boron-Containing Ionic Liquids 1-Alkyl-3-methylimidazolium Benzyoltrifluoroborates

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Ting WANG, Qi WEI, Qiang FU, Wei LI, Shi-Wei WANG. Review of Perovskite Photovoltaic Cell Encapsulation Material and Technology [J]. Chinese Journal of Applied Chemistry, 2022, 39(9): 1321-1344.
[2]	Chen-Si-Fan JIAO, Shao‑Bo ZHENG, Peng-Jun XU, Wei WANG, Takebe HIROMICHI, Mukai KUSUHIRO, Zhong-Da YU. Method of Evaluating the Foaming Properties of Surfactant Solutions— Real Sphere Bubble Method [J]. Chinese Journal of Applied Chemistry, 2022, 39(7): 1108-1118.
[3]	Xin-Wei DU, Wen-Jie ZHAO, Wei HU, Zhao-Yan SUN, Wan-Li LIU, Tian-Lei REN, Ming-Xing FU. Preparation and Properties of Poly（ether ether ketone）/Carbon Nanotube Modified Polypropylene Janus Composite Separator [J]. Chinese Journal of Applied Chemistry, 2022, 39(12): 1862-1869.
[4]	He LI, Gong LI, Xue GONG, Ming-Bo RUAN, Ce HAN, Ping SONG, Wei-Lin XU. Research on Performance Decay Mechanism of Pt/C Catalyst in Long‑Term ORR Test [J]. Chinese Journal of Applied Chemistry, 2022, 39(10): 1564-1571.
[5]	ZHAO Chang-Li, QIN Ming-Gao, DOU Xiao-Qiu, FENG Chuan-Liang. High Mechanical Stability and Osteogenesis of Chiral Supramolecular Hydrogel Induced by Inorganic Nanoparticles [J]. Chinese Journal of Applied Chemistry, 2022, 39(1): 177-187.
[6]	Ying ZHAO, Yi-Jia SHAO, Luo-Qian LI, Jian-Wei REN, Shi-Jun LIAO. Research Progress on the Degradation Mechanism and Cycle Stability Improvement of Lithium-Rich Cathode Materials [J]. Chinese Journal of Applied Chemistry, 2022, 39(02): 205-222.
[7]	QIAO Zong-Wen, CHEN Tao. Properties of Pyrenesulfonic Type Sulfonated Polysulfone Cation Exchange Membrane with High Performance Long Side Chain [J]. Chinese Journal of Applied Chemistry, 2021, 38(6): 668-674.
[8]	WU Zhen-Jiang, HUO Xiao-Wei, LIU Shou-Jun, YANG Song. Preparation and Application of Resin-Free Color Pastes in Water-Based Pigment Systems [J]. Chinese Journal of Applied Chemistry, 2021, 38(2): 212-219.
[9]	CAO You-Peng, PANG Xuan, XIANG Sheng, WANG Tian-Chang, FENG Li-Dong, BIAN Xin-Chao, LI Gao, CHEN Xue-Si. Solution-Induced Co-crystallization in Poly(lactic acid)/ Substituted Poly(lactic acid) Blends [J]. Chinese Journal of Applied Chemistry, 2021, 38(1): 60-68.
[10]	QIAO Zongwen, ZHAO Benbo. Properties of Sulfonated Polysulfone Proton Exchange Membranes Based on One-Pot Method [J]. Chinese Journal of Applied Chemistry, 2020, 37(6): 658-665.
[11]	AN Lulu, MI Jie. Synthesis of Nickel Cobalt Hydroxide and Its Electrochemical Properties [J]. Chinese Journal of Applied Chemistry, 2020, 37(5): 579-586.
[12]	JI Wanli, ZHONG Shaofeng, YU Xueman. Preparation and Properties of Superhydrophobic and Flame-Retardant Cotton Fabric [J]. Chinese Journal of Applied Chemistry, 2020, 37(3): 301-306.
[13]	WEN Pushan, HE Rui, ZHAO Guanglian, LIANG Xing, LEE Myonghoon. Preparation and Properties of Soluble Polyimides as the Liquid Crystal Alignment Layer [J]. Chinese Journal of Applied Chemistry, 2020, 37(12): 0-0.
[14]	WEN Pushan, HE Rui, ZHAO Guanglian, LIANG Xing, LEE Myonghoon. Preparation and Properties of Soluble Polyimides as the Liquid Crystal Alignment Layer [J]. Chinese Journal of Applied Chemistry, 2020, 37(12): 1403-1410.
[15]	FU Fengyan, CHENG Jingquan, ZHANG Jie, GAO Zhihua. Recent Development in Ionic Exchange Groups-Based Anion Exchange Membrane [J]. Chinese Journal of Applied Chemistry, 2020, 37(10): 1112-1126.