ES2469340A1 - Procedure for the manufacture of ionic liquids with the chloride structure of 1, w-bis- (3-methylimidazolium-1-yl) -alkane (w = 1,2,3,4,5,6 ) - Google Patents
Procedure for the manufacture of ionic liquids with the chloride structure of 1, w-bis- (3-methylimidazolium-1-yl) -alkane (w = 1,2,3,4,5,6 ) Download PDFInfo
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- ES2469340A1 ES2469340A1 ES201201280A ES201201280A ES2469340A1 ES 2469340 A1 ES2469340 A1 ES 2469340A1 ES 201201280 A ES201201280 A ES 201201280A ES 201201280 A ES201201280 A ES 201201280A ES 2469340 A1 ES2469340 A1 ES 2469340A1
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- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- -1 3-methylimidazolium-1-yl Chemical group 0.000 title claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000006228 supernatant Substances 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims abstract description 7
- 150000004693 imidazolium salts Chemical class 0.000 claims abstract description 7
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims abstract description 5
- 238000010908 decantation Methods 0.000 claims abstract description 4
- 239000002274 desiccant Substances 0.000 claims abstract description 4
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 24
- 238000005481 NMR spectroscopy Methods 0.000 claims description 19
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- JOKJNVOUNJXTOL-UHFFFAOYSA-L 1-methyl-3-[6-(3-methylimidazol-3-ium-1-yl)hexyl]imidazol-1-ium;dichloride Chemical compound [Cl-].[Cl-].C1=[N+](C)C=CN1CCCCCCN1C=[N+](C)C=C1 JOKJNVOUNJXTOL-UHFFFAOYSA-L 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- DPBNFNGLQSXFFZ-UHFFFAOYSA-L 1-methyl-3-[4-(3-methylimidazol-3-ium-1-yl)butyl]imidazol-1-ium;dichloride Chemical compound [Cl-].[Cl-].C1=[N+](C)C=CN1CCCCN1C=[N+](C)C=C1 DPBNFNGLQSXFFZ-UHFFFAOYSA-L 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- QADKPXXGGLHNBS-UHFFFAOYSA-N 1-methyl-3-[6-(3-methylimidazol-3-ium-1-yl)hexyl]imidazol-1-ium Chemical compound CN1C=C[N+](CCCCCC[N+]2=CN(C)C=C2)=C1 QADKPXXGGLHNBS-UHFFFAOYSA-N 0.000 description 2
- OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
- NWZIAPXEXQLMKE-UHFFFAOYSA-L 1-methyl-3-[(3-methylimidazol-3-ium-1-yl)methyl]imidazol-1-ium;dichloride Chemical compound [Cl-].[Cl-].C1=[N+](C)C=CN1CN1C=[N+](C)C=C1 NWZIAPXEXQLMKE-UHFFFAOYSA-L 0.000 description 1
- BZBABMLZUMYLPE-UHFFFAOYSA-N 1-methyl-3-[2-(3-methylimidazol-3-ium-1-yl)ethyl]imidazol-1-ium Chemical compound CN1C=C[N+](CC[N+]2=CN(C)C=C2)=C1 BZBABMLZUMYLPE-UHFFFAOYSA-N 0.000 description 1
- QUIMPROQYPPTNJ-UHFFFAOYSA-N 1-methyl-3-[5-(3-methylimidazol-3-ium-1-yl)pentyl]imidazol-1-ium Chemical compound C1=[N+](C)C=CN1CCCCCN1C=[N+](C)C=C1 QUIMPROQYPPTNJ-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Procedimiento para la fabricación de líquidos iónicos con la estructura de cloruro de 1,ω-bis-(3-metilimidazolio-1-il)-alcano (ω=1,2,3,4,5,6). La presente invención hace referencia a un procedimiento para la fabricación de líquidos iónicos dicatiónicos derivados del imidazolio que comprende las fases de: (i) añadir una cantidad efectiva de metilimidazol sobre una disolución de 1, ω-dicloroalcano en acetona para síntesis, (ii) refluir la mezcla obtenida en la fase (i), durante ocho días para ω= 2, durante tres días para ω= 3, 4 y 5 y durante un día para ω= 6 con tubo desecante de sílica azul cerrado, (iii) enfriar la mezcla obtenida en la fase (ii) a -10°C y separar la sal de imidazolio por decantación de la acetona sobrenadante, (iv) añadir acetona para síntesis a la sal de imidazolio obtenida en la fase (iii), refluir la mezcla durante aproximadamente 10 minutos, enfriar la mezcla a -10°C y decantar la acetona sobrenadante, (v) disolver el producto obtenido en la fase (iv) en etanol y saturar la mezcla por adición de acetona y hexano, (vi) enfriar la mezcla obtenida en la fase (v) a -10°C, decantar la acetona sobrenadante y desecar la mezcla durante aproximadamente dos horas, obteniendo el compuesto final.Procedure for the manufacture of ionic liquids with the chloride structure of 1,ω-bis-(3-methylimidazolium-1-yl)-alkane (ω=1,2,3,4,5,6). The present invention refers to a process for the manufacture of dicationic ionic liquids derived from imidazolium which comprises the phases of: (i) adding an effective amount of methylimidazole to a solution of 1, ω-dichloroalkane in acetone for synthesis, (ii) reflux the mixture obtained in phase (i), for eight days for ω= 2, for three days for ω= 3, 4 and 5 and for one day for ω= 6 with a closed blue silica desiccant tube, (iii) cool the mixture obtained in phase (ii) at -10°C and separate the imidazolium salt by decantation from the supernatant acetone, (iv) add acetone for synthesis to the imidazolium salt obtained in phase (iii), reflux the mixture for approximately 10 minutes, cool the mixture to -10°C and decant the supernatant acetone, (v) dissolve the product obtained in phase (iv) in ethanol and saturate the mixture by adding acetone and hexane, (vi) cool the mixture obtained in phase (v) at -10°C, decant the supernatant acetone and Dry the mixture for approximately two hours, obtaining the final compound.
Description
, Procedimiento para la fabricaci�n de liquidos i�nicos con la estructura de cloruro de 1,Cll-Bis-(3-metilimidazolio-l-il)-alcanos (co=l,2,3,4,5,6) La presente invenci�n se refiere a un procedimiento para obtener l�quidos i�nicos dicati�nicos derivados del imidazolio. 5 Antecedentes de la invenci�n Actualmente, algunos de los l�quidos i�nicos presentes en el mercado son derivados del imidazolio monocati�nicos. El documento de patente US 20120071661 Al hace referencia a diferentes procedimientos para fabricar l�quidos i�nicos derivados del imidazolio, pero todos ellos son 10 monocati�nicos. El procedimiento propuesto permite obtener l�quidos i�nicos dicati�nicos derivados del imidazolio, que presentan bajas presiones de vapor lo que disminuye las caracter�sticas t�xicas e inflamables de disolventes convencionales. Sumario de la invenci�n 15 La presente invenci�n hace referencia a un procedimiento para la fabricaci�n de l�quidos i�nicos dicati�nicos derivados del imidazolio que comprende las siguientes fases: (i) a�adir una cantidad efectiva de metilimidazol sobre una disoluci�n de 1,00-dicloroalcano en acetona para s�ntesis, (H) El reflujo de la mezcla obtenida en la fase (i), durante ocho d�as para 0>=2, durante tres 20 d�as para 0>= 3,4 Y 5 Y durante un d�a para 0>=6 con tubo desecante de s�lica azul cerrado, (iii) El enfriamiento de la mezcla obtenida en la fase (H) hasta los -10�C y se separaci�n de la sal de imidazolio por decantaci�n de la acetona sobrenadante, (iv) La adici�n de acetona para s�ntesis a la sal de imidazolio obtenida en la fase (iii), con reflujo de la mezcla durante aproximadamente 10 minutos; se enfr�a la mezcla a -10�C y se 25 decanta la acetona sobrenadante, (v) Se disuelve el producto obtenido en la fase (iv) en etanol y se satura la mezcla por adici�n de acetona y hexano, (vi) Se enfr�a la mezcla obtenida en la fase (v) hasta -10�C, se decanta la acetona sobrenadante y se deseca la mezcla durante aproximadamente dos horas, obteniendo el 30 compuesto final, Siendo las proporciones son las siguientes: -Metilimidazol entre un 3,75% y un 3,93% l,ro-Dicloroalcano entre un 2,04% y un 3,54% -Acetona para s�ntesis entre un 54,81 % Y un 57,47% 5 S�lica azul entre un 29,69% y un 31,13% -Etanol entre un 3,65% y un 3,83% -Hexano entre un 1,60% Y un 4,57% Es tambi�n caracter�stica de la invenci�n el componente principal, cloruro de l,ro-Bis-(3-10 metilimidazolio-l-il)-alcano, obtenido de acuerdo con el procedimiento antes mencionado, cuya f�rmula molecular es: donde ro= 1,2,3,4,5 y 6. As� mismo, resulta caracter�stico de la invenci�n el que el compuesto obtenido, de acuerdo 15 con el procedimiento mencionado, es seleccionado del grupo consistente en: Cloruro del 1,1-bis-(3-metilimidazolio-l-il)-metano (ro=1).-lH-NMR, 5 (DMSO-D6): 9.85 (2H, s), 8.24 (2H, s), 7.73 (2H, s), 6.91 (2H, s), 3.78 (6H, s). 13C_NMR, 5 (DMSO-D6): 139.10, 124.97, 122.84,58.38,36.93. Punto de fusi�n: 51-52 oC. Cloruro del 1,2-bis-(3-metilimidazolio-l-il)-etano (ro=2).-lH-NMR, 5 (DMSO-D6): 9.40 20 (2H, s), 7.81 (4H, br s), 4.82 (4H, s), 3.89 (6H, s). 13C_NMR, 5 (DMSO-D6): 137.60, 124.14, 122.66,48.61,36.46. L�quido a temperatura ambiente. 25 Cloruro dell,3-bis-(3-metilimidazolio-l-il)-propano (00=3).-lH-NMR, 5 (DMSO-D6): 9.68 (2H, s), 8.03 (2H, s), 7.88 (2H, s), 4.35 (4H, s), 3.92 (6H, s), 2.49 (2H, br s). 13C-NMR,5 (DMSO-D6): 137.34, 123.87, 122.41,45.81,36.05,29.77. Punto de fusi�n: 61-62 oC. -~----~---~-~~~---- Cloruro del 1,4-bis-(3-metilimidazolio-l-il)-butano �(1)=4).-lH-NMR, o (DMSO-D6): 9.61 (2H, s), 7.97 (2H, s), 7.83 (2H, s), 4.29 (4H, s), 3.86 (6H, s), 1.77 (4H, s). 13C-NMR, o (DMSO-D6): 137.03, 123.81, 122.51 (x2), 47.95, 36.05, 26.20. Punto de fusi�n: 68-69 oC. Cloruro del 1,5-bis-(3-metilimidazolio-l-il)-pentano �(1)=5).-lH-NMR, o (DMSO-D6): 9.65 5 (2H, s), 7.98 (2H, s), 7.84 (2H, s), 4.22 (4H, s), 3.88 (6H, s), 1.81 (4H, s), 1.16 (2H, s). 13C_ NMR, o (DMSO-D6): 137.02, 123.73, 122.53,48.37,35.96,28.71,21.93. Punto de fusi�n: 72-73 oC. Cloruro del 1,6-Bis-(3-metilimidazolio-l-il)-hexano �(1)=6).-IH-NMR, o (DMSO-D6): 9.55 (2H, s), 7.91 (2H, s), 7.79 (2H, s), 4.l9 (4H, t, J= 6.8 Hz), 3.96 (3H, s), 3.94 (3H, s), 1.76 10 (4H, s), 1.23 (4H, s). 13C-NMR, o (DMSO-D6): 136.76, 123.76, 122.52,48.70,35.96,29.28, 24.89. Punto de fusi�n: 112-113 oC. Descripci�n detallada de una realizaci�n preferida de la invenci�n Aunque la invenci�n se describe en t�rminos de una realizaci�n espec�fica preferida, es evidente para los expertos en esta t�cnica que se pueden hacer diversas modificaciones, 15 redisposiciones y reemplazos. El alcance de la invenci�n est� definido por las reivindicaciones adjuntas a la misma. El procedimiento de obtenci�n del cloruro del 1,6-bis-(3-metilimidazolio-l-il)-hexano �(1)=6) se inicia a�adiendo 1,64 g (0,02 moles) de metilimidazol, gota a gota, sobre una disoluci�n de 1,55 g (0,01 moles) de 1,6-diclorohexano en 20 mI de acetona para s�ntesis. 20 Posteriormente, la mezcla obtenida se refluja durante un d�a con tubo desecante de s�lica azul cerrado por un globo instalado en lo alto del refrigerante. La soluci�n obtenida se enfr�a hasta temperatura ambiente y el matraz que la contiene se retira del aparato de reflujo, se cubre herm�ticamente y se enfr�a hasta -10�C, condiciones en las que se separa la sal de imidazolio �(1)=6) por decantaci�n de la acetona sobrenadante. 25 Al producto que se obtiene se le a�aden 10 mI de acetona para s�ntesis y se somete a reflujo de nuevo otros 10 minutos. Se retira del aparato de reflujo, se cubre herm�ticamente y se vuelve a enfriar hasta los -10�C, decant�ndose la acetona sobrenadante. El residuo que se obtiene se disuelve en 2 mI de etanol absoluto y se lleva a saturaci�n por adici�n de 0,5 mI de acetona y 3 mI de hexano. Por �ltimo, se cubre herm�ticamente, se 30 enfr�a hata -10�C, se decanta y se deseca durante aproximadamente ocho horas en estufa de vacio a 40 oC y 3 mm Hg, obteni�ndose finalmente cloruro del 1,6-bis-(3-metilimidazolio-l-il)-hexano �(1)=6). , Procedure for the manufacture of ionic liquids with the chloride structure of 1, Cll-Bis- (3-methylimidazolium-l-yl) -alkanes (co = l, 2,3,4,5,6) The present invention relates to a process for obtaining ionic dicatinic liquids derived from imidazolium. BACKGROUND OF THE INVENTION Currently, some of the ionic liquids present in the market are monocatiinic imidazolium derivatives. The patent document US 20120071661 Al refers to different processes for manufacturing ionic liquids derived from imidazolium, but they are all monocathinic. The proposed procedure allows to obtain unique dicatinic liquids derived from imidazolium, which have low vapor pressures, which decreases the toxic and flammable characteristics of conventional solvents. SUMMARY OF THE INVENTION The present invention relates to a process for the manufacture of ionic dicatinic liquids derived from imidazolium which comprises the following steps: (i) adding an effective amount of methylimidazole on a solution of 1,00-dichloroalkane in acetone for synthesis, (H) The reflux of the mixture obtained in step (i), for eight days for 0> = 2, for three days. days for 0> = 3,4 and 5 Y during a day for 0> = 6 with closed blue silica desiccant tube, (iii) Cooling of the mixture obtained in phase (H) to the -10�C and separation of the imidazolium salt by decantation of the acetone supernatant, (iv) The addition of acetone for synthesis to the imidazolium salt obtained in step (iii), with refluxing the mixture for approximately 10 minutes; the mixture is cooled to -10 ° C and the acetone supernatant is decanted, (v) The product obtained in phase (iv) is dissolved in ethanol and the mixture is saturated by the addition of acetone and hexane, ( vi) The mixture obtained in phase (v) is cooled to -10 ° C, the acetone supernatant is decanted and the mixture is dried for approximately two hours, obtaining the final compound, The proportions being as follows: -Methylimidazole between 3.75% and 3.93% l, ro-Dichloroalkane between 2.04% and 3.54% -Acetone for synthesis between 54.81% And 57.47% 5 Blue silver between 29.69% and 31.13% -ethanol between 3.65% and 3.83% -Hexano between 1.60% and 4.57% It is also a feature of the invention the main component, l-ro-Bis- (3-10 methylimidazolium-l-yl) -alkane chloride, obtained according to the aforementioned process, whose f� Molecular formula is: where ro = 1,2,3,4,5 and 6. Also, it is characteristic of the invention that the compound obtained, according to the aforementioned procedure, is selected from the group consisting of: 1,1-bis- (3-methylimidazolium-1-yl) -methane chloride (ro = 1) .- lH-NMR, 5 (DMSO-D6): 9.85 (2H, s), 8.24 (2H , s), 7.73 (2H, s), 6.91 (2H, s), 3.78 (6H, s). 13C_NMR, 5 (DMSO-D6): 139.10, 124.97, 122.84.58.38,36.93. Melting point: 51-52 oC. Chloride of 1,2-bis- (3-methylimidazolium-1-yl) -ethane (ro = 2) .- lH-NMR, 5 (DMSO-D6): 9.40 20 (2H, s), 7.81 (4H, br s), 4.82 (4H, s), 3.89 (6H, s). 13C_NMR, 5 (DMSO-D6): 137.60, 124.14, 122.66.48.61.36.46. Liquid at room temperature. 25 Chloride dell, 3-bis- (3-methylimidazolium-1-yl) -propane (00 = 3) .- lH-NMR, 5 (DMSO-D6): 9.68 (2H, s), 8.03 (2H, s) , 7.88 (2H, s), 4.35 (4H, s), 3.92 (6H, s), 2.49 (2H, br s). 13C-NMR, 5 (DMSO-D6): 137.34, 123.87, 122.41.45.81.36.05.29.77. Melting point: 61-62 oC. - ~ ---- ~ --- ~ - ~~~ ---- 1,4-Bis- (3-methylimidazolium-1-yl) -butane Cl (1) = 4) .- lH-NMR chloride, or (DMSO-D6): 9.61 (2H, s), 7.97 (2H, s), 7.83 (2H, s), 4.29 (4H, s), 3.86 (6H, s), 1.77 (4H, s). 13C-NMR, or (DMSO-D6): 137.03, 123.81, 122.51 (x2), 47.95, 36.05, 26.20. Melting point: 68-69 oC. Chloride of 1,5-bis- (3-methylimidazolium-1-yl) -pentane � (1) = 5) .- lH-NMR, or (DMSO-D6): 9.65 5 (2H, s), 7.98 (2H , s), 7.84 (2H, s), 4.22 (4H, s), 3.88 (6H, s), 1.81 (4H, s), 1.16 (2H, s). 13C_ NMR, or (DMSO-D6): 137.02, 123.73, 122.53.48.37.35.96.28.71.21.93. Melting point: 72-73 oC. 1,6-Bis- (3-methylimidazolium-1-yl) -hexane chloride (1) = 6) .- IH-NMR, or (DMSO-D6): 9.55 (2H, s), 7.91 (2H, s), 7.79 (2H, s), 4.19 (4H, t, J = 6.8 Hz), 3.96 (3H, s), 3.94 (3H, s), 1.76 10 (4H, s), 1.23 (4H, s). 13C-NMR, or (DMSO-D6): 136.76, 123.76, 122.52.48.70.35.96.29.28, 24.89. Melting point: 112-113 oC. DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT OF THE INVENTION Although the invention is described in terms of a preferred specific embodiment, it is obvious to those skilled in the art that it can be done various modifications, 15 redispositions and replacements. The scope of the invention is defined by the claims appended thereto. The procedure for obtaining 1,6-bis- (3-methylimidazolium-1-yl) -hexane � (1) = 6) chloride is initiated by adding 1.64 g (0.02 mole) of methylimidazole , drop by drop, over a solution of 1.55 g (0.01 mole) of 1,6-dichlorohexane in 20 ml of acetone for synthesis. Subsequently, the obtained mixture is refluxed for one day with a blue silica desiccant tube closed by a balloon installed on top of the refrigerant. The solution obtained is cooled to room temperature and the flask containing it is removed from the reflux apparatus, is hermetically covered and cooled to -10 ° C, conditions in which the salt is separated from the water. imidazolium � (1) = 6) by decantation of the acetone supernatant. 25 To the obtained product, 10 ml of acetone are added for synthesis and refluxed again for another 10 minutes. It is removed from the reflux apparatus, covered tightly and cooled again to -10 ° C, decanting the acetone supernatant. The resulting residue is dissolved in 2 ml of absolute ethanol and brought to saturation by the addition of 0.5 ml of acetone and 3 ml of hexane. Finally, it is hermetically covered, cooled to -10 ° C, decanted and dried for approximately eight hours in a vacuum oven at 40 oC and 3 mm Hg, finally obtaining chloride from the 1, 6-bis- (3-methylimidazolium-1-yl) -hexane � (1) = 6).
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| Application Number | Priority Date | Filing Date | Title |
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| ES201201280A ES2469340A1 (en) | 2012-12-17 | 2012-12-17 | Procedure for the manufacture of ionic liquids with the chloride structure of 1, w-bis- (3-methylimidazolium-1-yl) -alkane (w = 1,2,3,4,5,6 ) |
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| Application Number | Priority Date | Filing Date | Title |
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| ES201201280A ES2469340A1 (en) | 2012-12-17 | 2012-12-17 | Procedure for the manufacture of ionic liquids with the chloride structure of 1, w-bis- (3-methylimidazolium-1-yl) -alkane (w = 1,2,3,4,5,6 ) |
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| ES201201280A Pending ES2469340A1 (en) | 2012-12-17 | 2012-12-17 | Procedure for the manufacture of ionic liquids with the chloride structure of 1, w-bis- (3-methylimidazolium-1-yl) -alkane (w = 1,2,3,4,5,6 ) |
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| Country | Link |
|---|---|
| ES (1) | ES2469340A1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009103062A1 (en) * | 2008-02-15 | 2009-08-20 | Sigma-Aldrich Co. | Anion detection by esi-ms using imidazolium-based dicationic liquid salts |
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2012
- 2012-12-17 ES ES201201280A patent/ES2469340A1/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009103062A1 (en) * | 2008-02-15 | 2009-08-20 | Sigma-Aldrich Co. | Anion detection by esi-ms using imidazolium-based dicationic liquid salts |
Non-Patent Citations (2)
| Title |
|---|
| A Jadhav et al, Chemical Engineering Journal 08-2012, vol 200-202, páginas 264-274. "Short oligo ethylene functionalized imidazolium dicationic ionic liquids: Synthesis, properties and catalytic activity in azidation", * |
| J Remsburg et al, Journal of American Society for Mass Spectrometry (Elsevier) 2008, vol 19, págs 261-269. "Evaluation of dicationic reagents for their use in detection of anions via gas phase ion association", página 263 compuestos 6 y 7 * |
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