There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type
HazMat fee for 500 gram (Estimated)
Excepted Quantity
USD 0.00
Limited Quantity
USD 15-60
Inaccessible (Haz class 6.1), Domestic
USD 80+
Inaccessible (Haz class 6.1), International
USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic
USD 100+
Accessible (Haz class 3, 4, 5 or 8), International
USD 200+
Structure of 174899-83-3 * Storage: {[proInfo.prStorage]}
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6758 - 6762
2
[ 369-57-3 ]
[ 174899-83-3 ]
[ 37595-74-7 ]
Reference:
[1] Chemical Communications, 2006, # 8, p. 897 - 899
[2] Chemical Communications, 2006, # 8, p. 897 - 899
3
[ 4316-42-1 ]
[ 77-78-1 ]
[ 174899-83-3 ]
Yield
Reaction Conditions
Operation in experiment
98%
Stage #1: for 0.25 h; Stage #2: With bis(trifluoromethane)sulfonimide lithium In water
In einen 5 I Reaktionsgefaess werden 620,5 g (5 mol) 1-Butylimidazol vorgelegt und 630,5g (5 mol) Dimethylsulfat portionsweise zugegeben. Der Ansatz wird danach 15 Minuten nachgeruehrt. Dazu gibt man eine Mischung von 1435,3g (5 mol) Lithium-bis-trifluormethansulfonimid in 2 Liter Wasser. Sofort bildet sich das Produkt als eine zweite fluessige Phase. Nach einer Phasentrennung wird das Produkt bei 60°C am HV getrocknet. Man erhaelt 1-Butyl-3-methylimidazolium-bis(trifluormethylsulfon)imid in 98 percentiger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 g des Produktes in ca. 5 ml Wasser geloest und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Silberchlorid-Niederschlags spricht fuer die komplette Abwesenheit von Halogenidionen. 1H-NMR (300 MHz, Aceton-d3):0,95 (3 H, tr, J=9,2 Hz, Hh); 1,33-1,39 (2 H, m, Hg); 1,90-2,00 (2 H, m, Hf); 4,07 (3 H, s, Hb); 4,37 (2 H, tr, J=9,3 Hz, He); 7,71;7,76 (je 1 H, s, Hc,d); 9,02 (1 H, s, Ha) ppm.
Reference:
[1] Patent: US2004/260112, 2004, A1, . Location in patent: Page 5
[2] Chemical Communications, 2018, vol. 54, # 49, p. 6260 - 6263
5
[ 85100-77-2 ]
[ 90076-65-6 ]
[ 174899-83-3 ]
Yield
Reaction Conditions
Operation in experiment
60%
at 20℃; for 24 h;
First 0.02 mol imidazolium bromide salt was added to 50 mL of dichloromethane and mixed. Then 0.02 mol bis(trifluoromethanesulfonyl)imide salt of lithium was added to the stirring solution of imidazolium bromide salt. The mixture was left stirring for about 24 h at room temperature. Then the lithium bromide salt was filtered and the concentrated AgNO3 solution was added to the solution. The resulting solution was washed with pure water so that AgBr was allowed to pass into the water phase. Then dichloromethane was evaporated with a rotary evaporator. The yield was calculated as 60percent.
Reference:
[1] Chemistry - A European Journal, 2010, vol. 16, # 23, p. 6748 - 6751
[2] New Journal of Chemistry, 2010, vol. 34, # 4, p. 723 - 731
[3] Journal of Organic Chemistry, 2012, vol. 77, # 17, p. 7291 - 7298
[4] Analytical Chemistry, 2004, vol. 76, # 10, p. 2773 - 2779
[5] Organic Letters, 2009, vol. 11, # 7, p. 1523 - 1526
[6] Organic and Biomolecular Chemistry, 2016, vol. 14, # 8, p. 2572 - 2580
[7] Organic and Biomolecular Chemistry, 2013, vol. 11, # 15, p. 2534 - 2542
[8] Chemistry Letters, 2016, vol. 45, # 4, p. 385 - 387
[9] Organic and Biomolecular Chemistry, 2017, vol. 15, # 30, p. 6433 - 6440
[10] Angewandte Chemie - International Edition, 2012, vol. 51, # 46, p. 11483 - 11486[11] Angew. Chem., 2012, vol. 124, # 46, p. 11650 - 11654,5
[12] New Journal of Chemistry, 2012, vol. 36, # 4, p. 1043 - 1050
[13] Angewandte Chemie - International Edition, 2017, vol. 56, # 31, p. 9072 - 9076[14] Angew. Chem., 2017, vol. 129, # 31, p. 9200 - 9204,5
[15] Turkish Journal of Chemistry, 2016, vol. 40, # 2, p. 364 - 372
[16] Chemical Communications, 2004, # 5, p. 590 - 591
[17] Journal of Physical Chemistry B, 2004, vol. 108, # 52, p. 20355 - 20365
[18] Angewandte Chemie - International Edition, 2007, vol. 46, # 28, p. 5384 - 5388
[19] Patent: US2006/12293, 2006, A1, . Location in patent: Page/Page column 8-9; 9-10; 10
[20] Tetrahedron, 2010, vol. 66, # 6, p. 1352 - 1356
[21] Asian Journal of Chemistry, 2011, vol. 23, # 10, p. 4355 - 4357
[22] Chemical Communications, 2012, vol. 48, # 91, p. 11220 - 11222
[23] RSC Advances, 2013, vol. 3, # 40, p. 18300 - 18304
[24] Angewandte Chemie - International Edition, 2014, vol. 53, # 8, p. 2099 - 2103[25] Angew. Chem., 2014, vol. 126, # 8, p. 2131 - 2135,5
[26] Journal of Solution Chemistry, 2014, vol. 43, # 2, p. 404 - 420
[27] Journal of Molecular Liquids, 2014, vol. 192, p. 191 - 198
[28] European Journal of Inorganic Chemistry, 2015, vol. 2015, # 26, p. 4354 - 4361
[29] RSC Advances, 2015, vol. 5, # 76, p. 62241 - 62247
[30] RSC Advances, 2015, vol. 5, # 80, p. 64821 - 64831
[31] Chemistry - A European Journal, 2016, vol. 22, # 45, p. 16113 - 16123
[32] New Journal of Chemistry, 2016, vol. 40, # 9, p. 7437 - 7444
[33] Catalysis Today, 2016, vol. 276, p. 112 - 120
[34] Patent: CN105272957, 2016, A, . Location in patent: Paragraph 0037-0038
6
[ 616-47-7 ]
[ 109-65-9 ]
[ 90076-65-6 ]
[ 174899-83-3 ]
Reference:
[1] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1553 - 1557
[2] Journal of Organic Chemistry, 2007, vol. 72, # 20, p. 7790 - 7793
[3] Journal of Solution Chemistry, 2010, vol. 39, # 3, p. 371 - 383
7
[ 4316-42-1 ]
[ 82113-65-3 ]
[ 149-73-5 ]
[ 174899-83-3 ]
Yield
Reaction Conditions
Operation in experiment
95%
for 0.5 h; Schlenk technique; Reflux; Inert atmosphere
1-butyl imidazole 1.28 mmol (0.168 mL) and bis (trifluoromethanesulfonyl) imide 1.28 mmol (360 mg) it was stirred for 30 minutes to put the schlenk tube. Then the reaction was refluxed trimethyl ortho formate 9.1mmol (0.7 mL) under N2 to the residue. Confirming that the protonated imidazole disappears then removed trimethyl ortho formate remaining in vacuo, and ethyl acetate and then dissolved in a small amount of methanol, deprotonate the small amount of the protonated imidazole was passed through a basic alumina It was. After having passed through this solution, putting them in a vacuum and the product was confirmed by NMR. Yield: 95percent
Reference:
[1] Green Chemistry, 2014, vol. 16, # 9, p. 4098 - 4101
[2] Patent: KR2015/79403, 2015, A, . Location in patent: Paragraph 0066-0069
8
[ 65039-05-6 ]
[ 90076-65-6 ]
[ 174899-83-3 ]
Reference:
[1] Physical Chemistry Chemical Physics, 2018, vol. 20, # 16, p. 11437 - 11443
[2] Chemistry of Materials, 2010, vol. 22, # 3, p. 1203 - 1208
9
[ 79917-90-1 ]
[ 90076-65-6 ]
[ 174899-83-3 ]
Reference:
[1] Catalysis Letters, 2010, vol. 134, # 3-4, p. 279 - 287
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 14, p. 2522 - 2529
[3] Green Chemistry, 2013, vol. 15, # 5, p. 1341 - 1347
[4] Journal of Physical Chemistry B, 2003, vol. 107, # 42, p. 11749 - 11756
[5] RSC Advances, 2016, vol. 6, # 93, p. 90273 - 90279
[6] European Journal of Inorganic Chemistry, 2004, # 6, p. 1190 - 1197
[7] ChemSusChem, 2014, vol. 7, # 12, p. 3407 - 3412
[8] Molecules, 2009, vol. 14, # 12, p. 5001 - 5016
[9] Journal of Physical Chemistry B, 2004, vol. 108, # 29, p. 10245 - 10255
[10] Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5316 - 5317
[11] Physical Chemistry Chemical Physics, 2003, vol. 5, # 13, p. 2790 - 2794
[12] Journal of Physical Chemistry B, 2004, vol. 108, # 42, p. 16593 - 16600
[13] Angewandte Chemie - International Edition, 2005, vol. 44, # 37, p. 6033 - 6038
[14] Synthesis, 2006, # 15, p. 2543 - 2550
[15] Chemistry - A European Journal, 2006, vol. 12, # 20, p. 5328 - 5333
[16] Chemical Communications, 2006, # 17, p. 1828 - 1830
[17] Journal of the American Chemical Society, 2008, vol. 130, # 5, p. 1552 - 1553
[18] Angewandte Chemie - International Edition, 2008, vol. 47, # 40, p. 7631 - 7634
[19] Chemistry - A European Journal, 2009, vol. 15, # 17, p. 4458 - 4463
[20] Patent: EP2163545, 2010, A1, . Location in patent: Page/Page column 22; 23
[21] Synthetic Communications, 2010, vol. 40, # 9, p. 1322 - 1332
[22] Chemical Communications, 2012, vol. 48, # 13, p. 1925 - 1927
[23] ChemSusChem, 2011, vol. 4, # 12, p. 1796 - 1804
[24] Macromolecules, 2013, vol. 46, # 23, p. 9464 - 9472
[25] Dalton Transactions, 2014, vol. 43, # 17, p. 6436 - 6445
[26] Dalton Transactions, 2018, vol. 47, # 14, p. 5083 - 5097
[27] Crystal Growth and Design, 2014, vol. 14, # 12, p. 6421 - 6432
[28] Zeitschrift fur Anorganische und Allgemeine Chemie, 2017, vol. 643, # 1, p. 130 - 135
10
[ 90076-65-6 ]
[ 342789-81-5 ]
[ 174899-83-3 ]
Reference:
[1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 243 - 248
In water; at 20℃; for 0.5h;Product distribution / selectivity;
In 4-necked flask of 500ml, 82.1 g (1.000mol) of 1-methylimidazole, 101.8 g (1.100mol) of 1-chlorobutane, and 50.0g of toluene were added and stirred for 15 hours under reflux (approximately 106C). After they were reacted in this way, a reaction solution was cooled (air-cooled) to 70C or below. Then, 100.0g of ultra pure water was added therein, the resultant solution was water-cooled to room temperature. After the cooling, an upper layer (toluene layer) of the solution was separated off from the solution by using a separating funnel. To a lower layer (water layer), 100.0g of toluene was further added. After the resultant solution was stirred for 30 min, an upper layer (toluene layer) was separated off from the solution by using a separating funnel, thereby remaining a water layer in which [BMIm]Cl being a cation portion of an ionic liquid was contained.(Anion-Exchange Reaction) After the separation, 53.8g of the water layer containing [BMIm]Cl (corresponding to 0.200mol of [BMIm]Cl) was transferred to a 300ml conical flask, and mixed with 63.2g (0.220mol) of lithium bis(trifluoromethanesulfonyl)imide and 50.0g of ultra pure water. A resultant mixture was stirred for 30min at room temperature in order to carry out an anion-exchange reaction. After the reaction, an upper layer (water layer) was separated out by using a separating funnel. A lower layer was mixed with 50.0g of ultra pure water and stirred for 30min at room temperature. Then, an upper layer (water layer) was separated out by using a separating funnel. A lower layer containing the cation portion of the ionic liquid was transferred to an egg-plant-shaped flask of 100ml and evaporated under reduced pressure at 60C under 20mmHg for 1 hour, so as to distill off water. In this way, a light yellow solution whose solvent was N-methyl-N'-butyl imidazolium bis(trifluoromethanesulfonyl)imide ([BMIm]NTf2) was obtained.(Salt Removal Step) After 50.0g of acetone was added thereto, the light yellow solution thus obtained was cooled to a temperature in a range of approximately 0 to 5C, and then stirred for 30 min, thereby trying to crystallize out lithium chloride (by-product) and unreacted lithium bis(trifluoromethanesulfonyl)imide. Even though the crystallization yielded no crystals, the resultant solution was filtered with a Buchner funnel having an internal diameter of 55mm, and then washed with 20.0g of acetone. A filtrate obtained from the filtration was then transferred to an egg-plant-shaped flask of 200ml and evaporated under reduced pressure at 60C under 20mmHg for 2 hours, and then further evaporated under reduced pressure at 60C under 1mmHg to 2mmHg for 1 hour. In this way, 73.8g of a concentrated solution containing the target [BMIm]NTf2 was obtained. The concentrated solution had water content of 0.0111% (111ppm).(Water Removing Step and Purifying Step) Then, 73.8g of the concentrated solution thus obtained was mixed with 0.20g (0.00166mol) of methyl orthoacetate (MOA). A resultant mixture was stirred at 80C for 3 hours so as to react MOA with water not distilled off from an ionic liquid. The reaction caused hydrolysis of MOA with the water thereby giving methanol and methyl acetate. The methanol and methyl acetate thus obtained and unreacted MOA were evaporated off under reduced pressure at 60C under 20mmHg for 1 hour. A concentrated liquid thus obtained was further evaporated under reduced pressure at 60C under 1mmHg to 2mmHg for 2 hours. In this way, a target material, [BMIm]NTf2 was obtained as a light yellow liquid.(Water Content Analysis of [BMIm]NTf2) Water content of [BMIm]NTf2 was measured by the Karl Fishcer test. Water content after the addition of MOA was 0.0032% (32ppm). Water content after methanol, methyl acetate and the unreacted MOA was evaporated off was 0.0037% (37ppm).
35 g (0.16 mol) of [C4mim][Br] was diluted with 100 mL of deionized water and 45.7 g (0.16 mol)of Li(Tf2N) was added. After mixing, the reaction mixture was separated into two layers. Thebottom layer was [C4mim] [Tf2N] and the top layer was aqueous LiCl. After decanting the toplayer, 100 mL of fresh deionized water was added and the solution was thoroughly mixed. Thisprocedure was repeated twice. The ionic liquid was dried in vacuo (under 0.1mbar) at 60C for 24hours, producing a colorless liquid (yield: 61.5 g, 87.5%).
60%
In dichloromethane; at 20℃; for 24h;
First 0.02 mol imidazolium bromide salt was added to 50 mL of dichloromethane and mixed. Then 0.02 mol bis(trifluoromethanesulfonyl)imide salt of lithium was added to the stirring solution of imidazolium bromide salt. The mixture was left stirring for about 24 h at room temperature. Then the lithium bromide salt was filtered and the concentrated AgNO3 solution was added to the solution. The resulting solution was washed with pure water so that AgBr was allowed to pass into the water phase. Then dichloromethane was evaporated with a rotary evaporator. The yield was calculated as 60%.
In water; at 20℃; for 3h;Electrochemical reaction;Product distribution / selectivity;
An embodiment of a reversible mirror of the invention was fabricated as follows: two electrodes were prepared using 6×8 cm single-side planar ITO coated glass plates having a sheet resistivity of 7 Omega/square. Each plate was provided with a bus bar by attaching a copper electrical contact approximately 1 cm wide along the entire edge of the 6 cm end of each plate. The electrodes were then washed with water, methanol and acetone, and dried in a stream of warm air to remove any dust or grease. An o-ring (2 cm internal diameter (ID) vycor rubber donut-shaped o-ring, 0.3 cm thick) was used as a gasket to seal one electrode to the other. A silver wire (5 cm long, 0.25 mm diameter, 99.9% metal purity) was inserted through the o-ring by first piercing a hollow needle through the o-ring, placing one end of the silver wire through the hollow needle, and then withdrawing the hollow needle from the o-ring. Approximately 0.4 mm of the silver wire protruded through the o-ring. The o-ring was then placed between the two electrodes with the conducting ITO coating in contact with the o-ring (see FIGS. 1 and 2) with the bus bars at opposite ends of the device. Two spring-loaded clips were used to hold the device together and provide a tight seal. A digital ohmmeter was used to ensure that the three electrodes (working, counter and pseudo-reference electrodes) were in electrical isolation of each other. Butylmethylimidazolium bis(trifluoromethylsulfonyl)imide was synthesized as follows: Butylmethylimidazolium bromide (50 g) was dissolved deionized water (100 mL). Decolorizing charcoal or activated carbon (3 g) was added to the solution, which was boiled for 3 minutes and filtered. The filtrate was added to a solution of lithium bis(trifluoromethylsulfonyl)imide (65.5 g) in 100 mL of deionized water. After stirring at room temperature for 3 hrs, two layers formed. The bottom layer containing butylmethylimidazolium bis(trifluoromethylsulfonyl)imide was separated, washed deionized water (3×50 mL), heated at 100 C. under vacuum (0.1 mbar) for 48 hrs, and then filtered through activated alumina to give anhydrous, highly pure, molten butylmethylimidazolium bis(trifluoromethylsulfonyl)imide. The purity of the molten salt was assayed by cyclic voltammetry, absorbance spectroscopy or fluorescence measurements. A solution of 3-butyl-1-methylimadazolium bis(trifluoromethylsulfonyl)imide containing less than 1 ppm water and 0.035 mol/L of bismuth (III) bis(trifluoromethylsulfonyl)imide was prepared in a helium atmosphere drybox. The solution was introduced into the chamber of the device by inserting two hollow needles through the o-ring (one needle for introducing the solution, the other needle for removing displaced gas). Afterward, the needles were removed and the o-ring was checked for leaks. Wire connectors were attached to the bus bars and to a potentiostat that provided the voltage for electrodeposition. A bismuth mirror was deposited at a potential of -0.65 Volts versus the silver reference electrode. The bismuth mirror was deplated at a potential of +0.1 Volts versus the silver reference electrode. Overall, this reversible mirror device exhibited good optical reflectance in the reflective state and good transparency in the non-mirrored state, and was switched repetitively between these two states without degradation of performance.
In water; at 70℃; for 24h;pH 6.0;
General procedure: The respective halide IL was dissolved in deionized water (pH =6) and after an equimolar amount of LiNTf2 in water had been added dropwise, the reaction mixture was stirred for 1 day at 70 C. Then CH2Cl2 was added and the aqueous phase was removed. The organic phase was washed halide-free with deionized water (AgNO3 test). The solution was filtered over a column filled with neutral Al2O3 and activated charcoal. The organic solvent was removed under reduced pressure and the reaction product finally dried under dynamic vacuum for 1-2 days at 80-90 C.
for 24h;Inert atmosphere;
Ionic liquid [bmim]Br was heated gently at 80C. The lithiumsalt LiTFSI was added to the melt under N2and stirred for 24 h.Adding CH2Cl2, LiBr was precipitated and separated by filtration.The filtrate was evaporated to dryness then the [bmim][TFSI]obtained.
In water; at 20℃; for 24h;
Then, the dried precursor BmimBr (0. 05 mmol, 10.5 g) and equimolar LiN (S02) 2 (CF3) 2 (0. 05 mmol, 13.7 g) were each dissolved in 20 mL H20 and mixed at room temperature 24h, After adding 50mL CH2Cl2, the water was removed and the aqueous phase was removed. After 5 times, CH2C12 was removed and dried at 80 C for 12 h to obtain ionic liquid [Bmim] [Tf2N].
In einen 5 I Reaktionsgefaess werden 620,5 g (5 mol) 1-Butylimidazol vorgelegt und 630,5g (5 mol) Dimethylsulfat portionsweise zugegeben. Der Ansatz wird danach 15 Minuten nachgeruehrt. Dazu gibt man eine Mischung von 1435,3g (5 mol) Lithium-bis-trifluormethansulfonimid in 2 Liter Wasser. Sofort bildet sich das Produkt als eine zweite fluessige Phase. Nach einer Phasentrennung wird das Produkt bei 60C am HV getrocknet. Man erhaelt 1-Butyl-3-methylimidazolium-bis(trifluormethylsulfon)imid in 98 %iger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 g des Produktes in ca. 5 ml Wasser geloest und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Silberchlorid-Niederschlags spricht fuer die komplette Abwesenheit von Halogenidionen. 1H-NMR (300 MHz, Aceton-d3):0,95 (3 H, tr, J=9,2 Hz, Hh); 1,33-1,39 (2 H, m, Hg); 1,90-2,00 (2 H, m, Hf); 4,07 (3 H, s, Hb); 4,37 (2 H, tr, J=9,3 Hz, He); 7,71;7,76 (je 1 H, s, Hc,d); 9,02 (1 H, s, Ha) ppm.
With bis(trifluoromethane)sulfonimide lithium; In water; at 20℃; for 90h;
(BMI+TF2N-) 41.92 g (0.240 mol) of 1-butyl-3-methylimidazolium chloride are dissolved in 300 ml of distilled water. 69.46 g (0.242 mol) of lithium bis(trifluoromethylsulphonyl)amide are added and the mixture is stirred under argon for 90 hours at ambient temperature. A two-phase system is formed. After extraction with 250 ml of dichloromethane, the organic phase is washed with 800 ml of water and then concentrated. The compound exists in the form of a slightly pinkish liquid which is purified by chromatography on a neutral alumina column (eluent: dichloromethane). It is then concentrated, taken up in acetonitrile in the presence of active carbon and filtered. After drying for several hours at 60 C., the compound is obtained in the form of a colourless liquid (81.47 g). Its structure, C10H15N3S2O4F6, was confirmed by NMR analysis.
With bis(trifluoromethane)sulfonimide lithium; In acetone; for 24h;
54 G of 1-BUTYL-3-METHYLIMIDAZOLIUM CHLORIDE WAS ADDED TO 150 ML OF acetone, and 68 G (1. 1 EQ.) of lithium bis (trifluorosulfonyl)imide was added thereto and reacted for 24 hours, followed by filtering the reactant solution to remove SAILS. The resulting filtrate was distilled to remove ACETONE, GIVING AN unpurified 1-BUTYL-3-METHYLIMIC3AZOLIUM bis (TRIFLUOROSULFONLY) IMIDE IONIC LIQUID. To the unpurified 1-BUTYL-3-METHYLIMIDAZOLIUM bis(trifluorosulfonyl)imide ionic liquid was added A mixed solution of ionic water and methyl alcohol (1V/3V) to prepare a product having a concentration of about 50%, followed by transferring to a reflux device of the continuous distillation extraction apparatus. Then, methylene chloride was added to a receiver (3v/w) and refluxed at 39- 40C for about 12 hours. Then, the methylene chloride solution was recovered from the receiver of the continuous distillation extraction apparatus and methylene chloride was distilled to be removed, followed by drying under reduced pressure at 60C for 76 hours to remove water, thereby acquiring a desired ionic liquid, 1-butyl-3-methylimidazolium bis (trifluorosulfonyl) imide ionic liquid. Yield : 100 g (95%), residual chloride ions: 2-20 ppm (before purification: 100 ppm), residual sodium ions: 1 No. 5 ppm (before purification: 30 ppm), water: 200 ppm. To achieve high purity ionic liquids, the obtained 1-butyl-3- methylimidazolium bis (trifluorosulfonyl) imide ionic liquid was repeatedly purified Yield : 99 g (99%), residual chloride ions: 1 No. 5 ppm (before repeated cycles of purification: 2-20 ppm), residual sodium ions > 3 ppm (before repeated cycles of purification : 1 No. 5 ppm), water : 200 ppm.
at 60 - 150℃; under 1500.15 - 7500.75 Torr;Purification / work up;
The liquid effluent arrives though pipe 1 at 1.5 MPa and 55 C. and is composed of 65 molar percent propane, 31 molar percent butanes, 2 molar percent hydrocarbons with at least five carbon atoms, and 2 molar percent methanol. This effluent may come from a stabilization chain of the condensates of a natural gas, the stripping step having been conducted at a low temperature in the presence of methanol to ensure that no hydrates form. According to the example, the ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide (BMIM) (TF2N) is used to recover the methanol. In zone ZA, 8 m3/h (25 kmol/h) of (BMIM) (TF2N) is introduced through pipe 9 to recover 95% of the methanol contained in the liquid effluent arriving at 1500 kmol/h through pipe 1. In this case, zone ZA can be a contactor ensuring efficiency equivalent to 4 theoretical stages. If the ionic liquid is introduced at the rate of 20 m3/h into zone ZA, zone ZA can consist of a cascade of two theoretical stages. For example, simpler technologies such as in-line mixers followed by separating drums can be used. Laboratory tests show perfect separation between the ionic liquid and the linear hydrocarbons having three to ten carbon atoms. The methanol recovery operation is conducted in the evaporator at a pressure of 0.2 MPa to 1 MPa and a temperature of 60 C. to 150 C. in order to favor evaporation of the methanol by heating.
Diazaonium salt 1 (44.8 mg, 0.141 mmol) was dissolved in [BMIM][NTf2] (0.4514 g, 1.076 mmol) and the mixture was heated at 70 C. for 15 h. NMR analysis of the reaction mixture indicated the formation of 34 and 35 and 30 in a 77:8:15 ratio. The mixture was extracted with hexane and the solvent was evaporated to give a pale yellow oil, whose SiO2 column chromatography with hexane/CH2Cl2 (8:2) afforded 35 (colorless crystals; 2.0 mg, 3%) and 34 (colorless oil; 24.3 mg, 36%). 34: (0147) MS (GC, EI): m/z=483 [M+], 464 [M+-F]. IR (ATR): v=1449, 1232, 1219, 1117, 837 cm-1. 1H NMR (500 MHz, CDCl3): delta=7.92 (d, J=8.7 Hz, 2H), 7.54 (t, J=8.7 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): delta=154.7 (C), 134.4 (C), 131.6 (2CH), 127.9 (2CH), 121.7 (q, J=222 Hz, CF3) ppm. 19F NMR (470 MHz, CDCl3): delta=81.3 (quint, J=150 Hz, 1 F), 62.7 (d, J=150 Hz, 4 F), -70.4 (s, 6 F) ppm.
Diazaonium salt 1 (44.8 mg, 0.141 mmol) was dissolved in [BMIM][NTf2] (0.4514 g, 1.076 mmol) and the mixture was heated at 70 C. for 15 h. NMR analysis of the reaction mixture indicated the formation of 34 and 35 and 30 in a 77:8:15 ratio. The mixture was extracted with hexane and the solvent was evaporated to give a pale yellow oil, whose SiO2 column chromatography with hexane/CH2Cl2 (8:2) afforded 35 (colorless crystals; 2.0 mg, 3%) and 34 (colorless oil; 24.3 mg, 36%). 34: (0147) MS (GC, EI): m/z=483 [M+], 464 [M+-F]. IR (ATR): v=1449, 1232, 1219, 1117, 837 cm-1. 1H NMR (500 MHz, CDCl3): delta=7.92 (d, J=8.7 Hz, 2H), 7.54 (t, J=8.7 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): delta=154.7 (C), 134.4 (C), 131.6 (2CH), 127.9 (2CH), 121.7 (q, J=222 Hz, CF3) ppm. 19F NMR (470 MHz, CDCl3): delta=81.3 (quint, J=150 Hz, 1 F), 62.7 (d, J=150 Hz, 4 F), -70.4 (s, 6 F) ppm.
(2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol[ No CAS ]
[ 1184-58-3 ]
[ 174899-83-3 ]
[ 1632137-32-6 ]
Yield
Reaction Conditions
Operation in experiment
95%
In dichloromethane; at -15℃; for 1h;Inert atmosphere;
General procedure: Me2AlCl (1 mmol),biaryl ligand (1 mmol), ionic liquid (1 mmol) and anhydCH2Cl2 (1 mL) were placed in a round-bottom flask under adry, inert atmosphere at -15 C. The contents of the flaskwere stirred for 1 h. After this time, evaporation of thesolvent gave complexes I-IV in high yields (90-99%).
In dichloromethane; at -15℃; for 1h;Inert atmosphere;
General procedure: Me2AlCl (1 mmol),biaryl ligand (1 mmol), ionic liquid (1 mmol) and anhydCH2Cl2 (1 mL) were placed in a round-bottom flask under adry, inert atmosphere at -15 C. The contents of the flaskwere stirred for 1 h. After this time, evaporation of thesolvent gave complexes I-IV in high yields (90-99%).
for 0.5h;Schlenk technique; Reflux; Inert atmosphere;
1-butyl imidazole 1.28 mmol (0.168 mL) and bis (trifluoromethanesulfonyl) imide 1.28 mmol (360 mg) it was stirred for 30 minutes to put the schlenk tube. Then the reaction was refluxed trimethyl ortho formate 9.1mmol (0.7 mL) under N2 to the residue. Confirming that the protonated imidazole disappears then removed trimethyl ortho formate remaining in vacuo, and ethyl acetate and then dissolved in a small amount of methanol, deprotonate the small amount of the protonated imidazole was passed through a basic alumina It was. After having passed through this solution, putting them in a vacuum and the product was confirmed by NMR. Yield: 95%
With N,N,N,N-tetraethylammonium tetrafluoroborate; In N,N-dimethyl-formamide; at 25℃;Inert atmosphere; Electrolysis;
General procedure: Catholyte (0.10molL-1 of ionic liquid 1a-h in 5.0mL of organic solvent) and anolyte (2.0mL same solvent/electrolyte) were separated through a porous glass frit filled with methylcellulose in DMF-Et4N-BF4. The electrolysis was carried out, under N2 atmosphere at 25C, at a constant current (J=15mA·cm-2). After the consumption of 31C, the current was switched off, the anodic compartment removed and the catholyte analyzed by cyclic voltammetry at different time intervals from the end of the electrolysis
In N,N-dimethyl-formamide; at 25℃;Inert atmosphere; Electrolysis;
General procedure: Catholyte (0.10 mol L1 of ionic liquid 1a-h in 5.0 mL of organicsolvent) and anolyte (2.0 mL same solvent/electrolyte) wereseparated through a porous glass fritfilled with methylcellulosein DMF-Et4N-BF4. The electrolysis was carried out, under N2atmosphere at 25 C, at a constant current (J = 15 mA cm2). Afterthe consumption of 31 C, the current was switched off, the anodiccompartment removed and the catholyte analyzed by cyclicvoltammetry at different time intervals from the end of theelectrolysis.
Diazaonium salt 1 (44.8 mg, 0.141 mmol) was dissolved in [BMIM][NTf2] (0.4514 g, 1.076 mmol) and the mixture was heated at 70 C. for 15 h. NMR analysis of the reaction mixture indicated the formation of 34 and 35 and 30 in a 77:8:15 ratio. The mixture was extracted with hexane and the solvent was evaporated to give a pale yellow oil, whose SiO2 column chromatography with hexane/CH2Cl2 (8:2) afforded 35 (colorless crystals; 2.0 mg, 3%) and 34 (colorless oil; 24.3 mg, 36%). 34: (0147) MS (GC, EI): m/z=483 [M+], 464 [M+-F]. IR (ATR): v=1449, 1232, 1219, 1117, 837 cm-1. 1H NMR (500 MHz, CDCl3): delta=7.92 (d, J=8.7 Hz, 2H), 7.54 (t, J=8.7 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): delta=154.7 (C), 134.4 (C), 131.6 (2CH), 127.9 (2CH), 121.7 (q, J=222 Hz, CF3) ppm. 19F NMR (470 MHz, CDCl3): delta=81.3 (quint, J=150 Hz, 1 F), 62.7 (d, J=150 Hz, 4 F), -70.4 (s, 6 F) ppm.
General procedure: The diazonium tetrafluoroborates (10-20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexane-CH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography.
2-(4-methylbenzoyl)benzenediazonium tetrafluoroborate[ No CAS ]
[ 174899-83-3 ]
[ 1705-89-1 ]
C16H11F6NO5S2[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
at 80℃; for 1.5h;
General procedure: The diazonium tetrafluoroborates (10-20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexane-CH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography.
2-(4-chlorobenzoyl)benzenediazonium tetrafluoroborate[ No CAS ]
[ 174899-83-3 ]
[ 7254-06-0 ]
C15H8ClF6NO5S2[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
at 80℃; for 1h;
General procedure: The diazonium tetrafluoroborates (10-20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexane-CH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography.
2-benzylbenzenediazonium tetrafluoroborate[ No CAS ]
[ 174899-83-3 ]
[ 86-73-7 ]
C15H11F6NO4S2[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
at 80℃; for 6h;
General procedure: The diazonium tetrafluoroborates (10-20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexane-CH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography.
General procedure: The diazonium tetrafluoroborates (10-20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexane-CH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography.
2-(4-methoxybenzoyl)benzenediazonium tetrafluoroborate[ No CAS ]
[ 174899-83-3 ]
[ 15144-82-8 ]
C16H11F6NO6S2[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
at 80℃; for 2h;
General procedure: The diazonium tetrafluoroborates (10-20 mg) were dissolved in ionic liquids (0.4 mL). The solution was heated using the conditions shown in Table 1. The ionic liquids were extracted with hexane. After removal of the solvent, the residues were analyzed by NMR, and the product distributions are summarized in Table 1. Compounds 2a,22 2b,23 2c,24 2d,23 2e,22 3a,25 3d,26 3e,27 and 3f27 were identified by comparing their NMR spectra with those reported in the literature. The isomers ArOSO(CF3)(NTf) (4a-4f) and ArNTf2 (5a-5f) were attempted to be purified with SiO2 column chromatography using hexane-CH2Cl2 or hexane-ether as an eluent. However, they could not be separated by chromatography.