• Title/Summary/Keyword: Acidic Ionic Liquid

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Highly Chemo- and Regioselective Reaction of Hydroxybenzenes in Acidic Ionic Liquid

  • Guo, Hui;Zhuang, Yu Wei;Cao, Jian;Zhang, Guo Bao
    • Bulletin of the Korean Chemical Society
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    • v.34 no.9
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    • pp.2594-2596
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    • 2013
  • Highly chemo- and regioselective reaction of hydroxybenzenes with ${\alpha},{\beta}$-unsaturated compounds in acidic ionic liquid l-butyl-3-methylimidazolium hydrogen sulphate ([BMIM]HSO4) was reported for the first time. A series of oxa-Michael adducts and Friedel-Crafts alkylated products were synthesized with good yields. The acidic ionic liquid could be easily recycled for at least 5 times with only minor loss in activity.

The Analytical Study on Synthesis and Optimization of Purification of Ionic Liquid, 1-ethyl-3-methylimidazolium Tetrafluoroborate (이온성 액체 1-ethyl-3-methylimidazolium Tetrafluoroborate의 정제 최적화 조건에 따른 특성 변화 분석 연구)

  • Yang, Kyung-Chul;Chun, Kyung-Soo
    • Journal of the Korean Ceramic Society
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    • v.50 no.2
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    • pp.103-107
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    • 2013
  • In this study, the ionic liquid 1-ethyl-3-methylimidazolium tetraflouroborate (EMI-BF4) was synthesized and purified using the liquid/liquid fractional distillation method to apply a supercapacitor. EMI-BF4 was extracted with dichloromethane from the liquid/liquid extraction method in acidic, neutral, and alkali conditions for removal of impurity, and then the electrical capacities of the purified ionic liquids were measured and compared. The electrical capacities of ionic liquids under acidic condition showed higher value than those of neutral or alkali conditions. As the ratio of ionic liquid to solvent became higher, the electrical capacity value was increased.

Preparation, Characterization and First Application of Aerosil Silica Supported Acidic Ionic Liquid as a Reusable Heterogeneous Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

  • Yassaghi, Ghazaleh;Davoodnia, Abolghasem;Allameh, Sadegh;Zare-Bidaki, Atefeh;Tavakoli-Hoseini, Niloofar
    • Bulletin of the Korean Chemical Society
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    • v.33 no.8
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    • pp.2724-2730
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    • 2012
  • A new heterogeneous acidic catalyst was successfully prepared by impregnation of silica (Aerosil 300) by an acidic ionic liquid, named 1-(4-sulfonic acid)butylpyridinium hydrogen sulfate [$PYC_4SO_3H$][$HSO_4$], and characterized using FT-IR spectroscopy, the $N_2$ adsorption/desorption analysis (BET), thermal analysis (TG/DTG), and X-ray diffraction (XRD) techniques. The amount of loaded acidic ionic liquid on Aerosil 300 support was determined by acid-base titration. This new solid acidic supported heterogeneous catalyst exhibits excellent activity in the synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation reaction of 2-aminobenzamide with aromatic aldehydes under solvent-free conditions and the desired products were obtained in very short reaction times with high yields. This catalyst has the advantages of an easy catalyst separation from the reaction medium and lower problems of corrosion. Recycling of the catalyst and avoidance of using harmful organic solvent are other advantages of this simple procedure.

Polymer Support Immobilized Acidic Ionic Liquid: Preparation and Its Application as Catalyst in the Synthesis of Hantzsch 1,4-Dihydropyridines

  • Jahanbin, Bentolhoda;Davoodnia, Abolghasem;Behmadi, Hossein;Tavakoli-Hoseini, Niloofar
    • Bulletin of the Korean Chemical Society
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    • v.33 no.7
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    • pp.2140-2144
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    • 2012
  • A polymer support immobilized acidic ionic liquid was prepared by copolymerization of 3-vinyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate with styrene in the presence of benzoyl peroxide and its primary application as a solid acidic heterogeneous catalyst to the synthesis of Hantzsch 1,4-dihydropyridines through a one-pot three-component reaction of aromatic aldehydes, ethyl acetoacetate and ammonium acetate was investigated. The results showed that this heterogeneous catalyst has high catalytic activity and the desired products were obtained in good to high yields. Moreover, the catalyst was found to be reusable and a considerable catalytic activity still could be achieved after third run.

Preparation of Novel Ionic Liquids and Their Applications in Brominating Reaction (새로운 이온용액의 제조 및 브롬화반응 응용)

  • Li, Hua;Liu, Juan;Zhu, Jiang;Wang, Hongkai
    • Journal of the Korean Chemical Society
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    • v.55 no.4
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    • pp.685-690
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    • 2011
  • Novel acidic ionic liquids, 1-(${\omega}$-sulfonicacid)propyl-3-methylimidazolium bromide ([$HSO_3$pmim]Br)and 1-(${\omega}$-sulfonicacid)butyl-3-methylimidazolium bromide ([$HSO_3$bmim]Br), were prepared and used as brominating agents, catalysts and solvents in the synthesis of 1,7-dibromoheptane, respectively. 1,7-dibromoheptan with a yield of 95% was obtained at $100^{\circ}C$ for 2 h by simple phase separation. The acidic ionic liquid [$HSO_3$pmim]Br was recycled for 5 times and the yield of 1,7-dibromoheptane did not decrease remarkably, which indicates that catalysts still maintain good selectivity and activity after recycling. The structure of the acidic ionic liquid [$HSO_3$pmim]Br was characterized with IR, and it was found that [$HSO_3$pmim]Br had stronger acidity than other ionic liquid.

Reusable and Efficient Polystryrene-supported Acidic Ionic Liquid Catalyst for Mononitration of Aromatic Compounds

  • Li, Li Xia;Ling, Qi Long;Liu, Zu Liang;Xing, Xiao Dong;Zhu, Xiao Qin;Meng, Xiao
    • Bulletin of the Korean Chemical Society
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    • v.33 no.10
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    • pp.3373-3377
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    • 2012
  • A series of polystyrene-supported 1-(propyl-3-sulfonate)-3-methyl-imidazolium hydrosulfate acidic ionic liquid (PS-$[SO_3H-PMIM][HSO_4]$) catalysts were prepared and tested for mononitration of simple aromatics compounds with nitric acid. It was found that the reactivity of the catalysts increased with increasing $[SO_3H-PMIM][HSO_4]$ content. The para-selectivity was not only related to the $[SO_3H-PMIM][HSO_4]$ content but also the substituent groups in aromatics. A reaction mechanism of nitration over this new catalyst was proposed. The catalytic activity of this catalyst decreased slightly after fifth runs in the synthesis of nitrotoluene.

Synthesis of Biodiesel from Soybean Oil Using Lewis Acidic Ionic Liquids Containing Metal Chloride Salts (금속염화물을 첨가한 루이스산 이온성 액체 촉매를 이용한 대두유로부터 바이오디젤 합성)

  • Choi, Jae Hyung;Park, Yong Beom;Lee, Suk Hee;Cheon, Jae Kee;Choi, Jae Wook;Woo, Hee Chul
    • Korean Chemical Engineering Research
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    • v.48 no.5
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    • pp.643-648
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    • 2010
  • Production of biodiesel from soybean oil catalyzed by Lewis acidic ionic liquids(ILs) containing metal chloride salts was investigated in this study. Metal chloride salts, such as $SnCl_2$, $ZnCl_2$, $AlCl_3$, $FeCl_3$ and CuCl, were screened for oil transesterification in the range of 363-423 K. Among these metal chlorides, tin chloride showed particularly high catalytic property for the oil transesterification. Similarly, among these Lewis acidic ionic liquid catalysts, $[Me_3NC_2H_4OH]Cl-2SnCl_2$ resulted in a high fatty acid methyl esters(FAMEs) content of 91.1% under the following reaction conditions: 403 K, 14 h, and a molar ratio of 1:12:0.9 (oil:methanol:catalyst). Unlike the pure tin chloride catalysts, Lewis acidic ILs containing tin chloride $[Me_3NC_2H_4OH]Cl-2SnCl_2$ catalyst could be recycled up to five times without any significant loss of activity by separating from the FAMEs with simple decantation. The Lewis acidity and high moisture-stability of this catalyst appeared to be responsible for the excellent catalytic performance. The effects of reaction time and the molar ratio of methanol/catalyst to oil on the FAMEs production were also studied in this work.

Solvent Extraction of Tb(III) from Hydrochloric Acid Solution with Cyanex 272, Its Mixture and Ionic Liquid (염산용액에서 Cyanex 272 및 혼합용매와 이온성 액체에 의한 Tb(III)의 용매추출)

  • Oh, Chang Geun;Lee, Man Seung
    • Korean Journal of Metals and Materials
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    • v.56 no.12
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    • pp.870-877
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    • 2018
  • Cyanex 272 shows the highest separation factor for the rare earth elements from hydrochloric acid solution among the organophosporus acidic extractants, D2EHPA and PC 88A. Solvent extraction of Tb(III) from weak hydrochloric acid solution with an initial pH 3 to 6 was compared with Cyanex 272, its mixture with Alamine 336, and ionic liquid with Aliquat 336. The solvent extraction reaction of Tb(III) using Cyanex 272 was the same as that of light rare earth elements. Synergism was observed for the extraction of Tb(III) by the mixture with Alamine 336 when the initial concentration ratio of Cyanex 272 to Alamine 336 was higher than 5. Use of the ionic liquid led to a great increase in the extraction percentage of Tb(III) from the same initial extraction conditions. While the equilibrium pH of the mixture was always lower than the initial pH, under some conditions extraction with the ionic liquid resulted in a higher equilibrium pH than the initial pH. The loading capacity of the mixture and the ionic liquid was the same and 2.6 times larger than that using Cyanex 272 alone. Ionic liquid was recommended as a suitable extractant for the extraction of Tb(III) from hydrochloric acid solution based on the ease of handling and higher extraction percentage.

A DABCO Derived Ionic Liquid Based on Tetrafluoroborate Anion: Preparation, Characterization and Evaluation of its Catalytic Activity in the Synthesis of 14-Aryl-14H-dibenzo[a, j]xanthenes

  • Atefeh, Zare-Bidaki;Davoodnia, Abolghasem
    • Bulletin of the Korean Chemical Society
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    • v.33 no.4
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    • pp.1154-1158
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    • 2012
  • A room-temperature ionic liquid (RTIL) derived from 1,4-diazabicyclo[2.2.2]octane (DABCO) consisting of tetrafluoroborate anion, 1-butyl-4-(4-sulfonylbutyl)-1,4-diazoniabicyclo[2.2.2]octane hydrogen sulfate tetrafluoroborate ($[C_4DABCOC_4SO_3H][BF_4][HSO_4]$) was synthesized and catalytically evaluated in the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes by cyclocondensation reaction of ${\beta}$-naphthol and aryl aldehydes. This novel RTIL with an acidic $SO_3H$ group showed high catalytic activity with good to excellent yields of the desired products in short reaction times. Moreover, the catalyst could be recovered and reused at least three times with only slight reduction in its catalytic activity.

1-Butyl-3-Methyl Imidazolium Hydrogen Sulphate Promoted One-Pot Three-Component Synthesis of Amidoalkyl Naphthols

  • Sapkal, Suryakant B.;Shelke, Kiran F.;Madje, Balaji R.;Shingate, Bapurao B.;Shingare, Murlidhar S.
    • Bulletin of the Korean Chemical Society
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    • v.30 no.12
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    • pp.2887-2889
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    • 2009
  • An efficient and easy method for one-pot three-component synthesis of amidoalkyl naphthols by the condensation of aromatic/heteroaromatic/aliphatic aldehydes, 2-naphthol and amides or urea under thermal condition at $60^{\circ}C$ in the presence of acidic ionic liquid 1-butyl-3-methylimidazolium hydrogen sulphate ([bmim]$HSO_4$) has been described.