Structure of 6220-15-1
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CAS No. : | 6220-15-1 |
Formula : | C11H18ClN |
M.W : | 199.72 |
SMILES Code : | CCCCCC[N+]1=CC=CC=C1.[Cl-] |
MDL No. : | MFCD03093294 |
InChI Key : | JEOSMYVMLZTQOH-UHFFFAOYSA-M |
Pubchem ID : | 2734172 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | at 85℃; for 24h; | Pyridine (0.4 mol) and 1-chlorobutane (or 1-chlorohexane or 1-chlorooctane) (0.4 mol) were placed into a 250 cm3 round bottom flask equipped with an electric heat-jacket and vigorously stirred using a magnetic stirrer for 24 h; at 75 C ([C4-py]Cl) or 85 C ([C6-py]Cl and [C8-py]Cl). [C4-py]Cl and [C6-py]Cl, obtained in the form of the white solids directly after synthesis, were washed in Schlenk apparatus with diethyl ether (4 × 50 cm3) and hexane (4 × 50 cm3) and dried by nitrogen stream. [C8-py]Cl obtained in the form of a transparent yellow, dense, and viscous liquid was cooled to room temperature and extracted by turns with diethyl ether (4 × 50 cm3) and hexane (4 × 50 cm3) and dried by nitrogen stream. Yields: 77% for [C4-py]Cl, 39% for [C6-py]Cl, and 52% for [C8-py]Cl. |
In toluene; at 106℃; for 22h; | In 4-necked flask of 300ml, 15.8 g (0.200mol) of pyridine, 26.5 g (0.220mol) of 1-chlorohexane, and 50.0g of toluene were added and stirred for 22 hours under reflux (approximately 106C). After they were reacted in this way, a reaction solution was cooled (air-cooled) to 70C or below. Then, 50.5g 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 (organic layer), 50.0g 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 N-n-hexyl pyridinium chloride (hereinafter, referred to as [HPy]Cl) being a cation portion of an ionic liquid was contained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20℃; for 1h; | In 4-necked flask of 300ml, 15.8 g (0.200mol) of pyridine, 26.5 g (0.220mol) of 1-chlorohexane, and 50.0g of toluene were added and stirred for 22 hours under reflux (approximately 106C). After they were reacted in this way, a reaction solution was cooled (air-cooled) to 70C or below. Then, 50.5g 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 (organic layer), 50.0g 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 N-n-hexyl pyridinium chloride (hereinafter, referred to as [HPy]Cl) being a cation portion of an ionic liquid was contained.(Anion-Exchange Reaction) After the separation, 126.8g of the solution containing [HPy]Cl (corresponding to 0.200mol of [HPy]Cl) was transferred to a 300ml egg-plant-shaped flask, and mixed with 63.2g (0.220mol) of lithium bis (trifluoromethanesulfonyl) imide. A resultant mixture was stirred for 1 hour 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 200ml and evaporated under reduced pressure at 60C under 20mmHg for 1 hour, so as to distill off a solvent. In this way, a light yellow solution containing N-n-hexyl pyridinium bis (trifluoromethanesulfonyl) imide ([HPy]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 3 hours, and then further evaporated under reduced pressure at 60C under 1mmHg to 2mmHg for 1 hour. In this way, 93.4g of a concentrated solution containing the target [HPy]NTf2 was obtained. The concentrated solution had water content of 0.0069% (69ppm).(Water Removing Step and Purifying Step) Then, 93.4g 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, [HPy]NTf2 was obtained as a light yellow liquid.(Water Content Analysis of [HPy]NTf2) Water content of [HPy]NTf2 was measured by the Karl Fishcer test. Water content after the addition of MOA was 0.0000% (0ppm). Water content after methanol, methyl acetate and the unreacted MOA was evaporated off was 0.0000% (0ppm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | 12.14 g (28.5 mmol) of (C2F5)3PF2 are slowly added at 0 C. to 30 ml of a one molar LiAlH4/THF solution (30 mmol), and the mixture is stirred for 30 minutes. The solution is hydrolysed using water at 0 C., giving a colourless precipitate (aluminium hydroxide), and 5.67 g (28.5 mmol) of N-hexylpyrridinium chloride, dissolved in 10 ml of water, are added. After stirring for 30 minutes, the precipitate is filtered off. The emulsion obtained is dried in vacuo. The cloudy, viscous residue is extracted three times with water and again dried in vacuo, leaving a colourless liquid. Yield (based on N-hexylpyrridinium chloride): 9.98 g (59%) Analytical data of [HPy][P(C2F5)3F2H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃;Inert atmosphere; | To the obtained 1-alkylpyridinium chlorides, the equimolar amount of aluminium chloride was added stepwise carefully under a nitrogen atmosphere at room temperature. The mixtures were magnetically stirred and the transparent, slightly brownish chloroaluminate ionic liquids were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.07 g | With hydrogen fluoride; In water; at 60 - 100℃; for 3h; | (1) Take a purity of 99% by mass 10g of N- hexyl pyridinium chloride was added 25mL of distilled water were dissolved, was added 50mL of 40% concentration hydrofluoric acid, sealed and heated to 60oC with stirring;(2) the raw material at least sufficient reaction 3h, then heated to 100oC, evaporate excess product hydrogen chloride gas and hydrogen fluoride gas, tail gas absorption using calcium oxide, not to get dehydrated N- hexyl pyridinium fluoride ionic liquids;(3) was added to N- hexyl pyridinium fluoride ionic liquid was diluted with distilled water, the volume of pyridine N- butylammonium fluoride ionic liquids are not dehydrated and distilled water is less than 1:50, the dilution was added AgNO3 solution, if the precipitate production, continue to add 20mL hydrofluoric acid, repeating (1) and (2) step until no precipitate was produced, purified non-dehydrated N- hexyl pyridinium fluoride ionic liquids;(4) non-purified dehydrated N- hexyl pyridinium fluoride at 120oC ionic liquid was dried under high vacuum at least 48h, in addition to the depth of water, in addition to hydrogen fluoride, to give a viscous liquid, viscous liquid of detecting, through the viscous distilled water was added to the liquid, viscous liquid with distilled water volume ratio of less than 1:50 high vacuum, sealed and heated to 60oC, with hydrogen detector dilution residual amount of hydrogen fluoride, if the reading is greater than> 0.1ppm, continue at 120oC In addition to hydrogen fluoride was dried until the testHydrogen fluoride concentration <0.1ppm; if detected hydrogen fluoride concentration <0.1ppm, the resulting liquid is N- hexyl pyridinium fluoride ionic liquids, weighing 9.07g. |
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