CN102675208A - 1-(3-chloro-2-hydroxypropyl)-3-methylimidazol ionic liquid and preparation method thereof - Google Patents
1-(3-chloro-2-hydroxypropyl)-3-methylimidazol ionic liquid and preparation method thereof Download PDFInfo
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- CN102675208A CN102675208A CN2012101066929A CN201210106692A CN102675208A CN 102675208 A CN102675208 A CN 102675208A CN 2012101066929 A CN2012101066929 A CN 2012101066929A CN 201210106692 A CN201210106692 A CN 201210106692A CN 102675208 A CN102675208 A CN 102675208A
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- epoxy chloropropane
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Abstract
The invention provides a 1-(3-chloro-2-hydroxypropyl)-3-methylimidazol ionic liquid and a preparation method of the ionic liquid. The preparation method of the ionic liquid particularly comprises the steps of: adding concentrated hydrochloric acid to a three-neck flask, dropwise adding N-methylimidazol, reacting for 1h while controlling the reaction temperature not more than 30 DEG C and adjusting the pH value with N-methylimidazol; adding ethanol as solvent, measuring epoxy chloropropane in a dropping funnel, heating and stirring the flask, slowly dropwise adding epoxy chloropropane when the solution temperature is raised to 30-80 DEG C, continuing reacting for 1-4h, distilling under reduced pressure to remove epoxy chloropropane, ethanol and water, and cooling to room temperature; extracting to remove N-methylimidazol with ethyl ether as an extractant; and then drying to finally obtain the ionic liquid. The ionic liquid has the characteristics of simple and quick synthesis method; the product has stronger solubility property to cellulose; the production cost is lower; and the ionic liquid can be recovered and regenerated, so that a green chemical principle is sufficiently embodied.
Description
Technical field
The present invention relates to chemical field, specifically is a kind of novel ionic liquid and preparation method thereof.
Technical background
The ionic liquid General Definition is the liquid system of being made up of organic cation and inorganic anion; They have wide stable electrochemical window, do not have vp, a good solvability basically; Good electrical conductivity, good thermostability and chemicalstability; Generally can the recirculation utilization, be considered to replace in a lot of fields the green solvent of volatile chemical solvents.
And along with the rapid exhaustion in Nonrenewable resources (like oil, Sweet natural gas, colliery etc.); The development and utilization of natural polymer receives people's attention; But because the higher percent crystallinity of natural cellulose and intermolecular and molecular memory are at a large amount of hydrogen bonds; Make its undissolved characteristics in most of solvents, this becomes the biggest obstacle of Mierocrystalline cellulose in application and development.Developing low-cost, eco-friendly cellosolve remain the development trend in this field, and ionic liquid is that a frontier has been opened up in the development research of cellosolve system as eco-friendly green solvent.
Summary of the invention
The invention provides a kind of 1-(3-chloro-2-hydroxypropyl)-3-Methylimidazole ionic liquid, and this preparation method of ionic liquid is provided.
1-provided by the invention (3-chloro-2-hydroxypropyl)-3-Methylimidazole ionic liquid is characterized in that structural formula is following:
The above-mentioned preparation method of ionic liquid of the present invention; It is characterized in that; The concentrated hydrochloric acid that in the there-necked flask that whisking appliance, tap funnel and TM are housed, adds 6-10 mass parts 36% (mass concentration) drips the N-Methylimidazole of 6-10 mass parts while stirring, and control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization); Behind the reaction 1h, use the N-Methylimidazole to regulate the pH value and be 6-7.Add 10-17 mass parts ethanol and make solvent, the epoxy chloropropane of measuring the 5-12 mass parts assembles instrument in tap funnel; Heat with oil bath; Utilize constant temperature blender with magnetic force that flask is heated and stirring, when solution temperature rises to 30-80 ℃, slowly drip epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation after continuing to react 1-4h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry in 80 ℃ vacuum drying oven then, obtain faint yellow viscous liquid at last, promptly be 1-(3-chloro-2-hydroxypropyl)-3-Methylimidazole ionic liquid.
Said room temperature is 20-35 ℃.
1-of the present invention (3-chloro-2-hydroxypropyl)-3-Methylimidazole ionic liquid have compound method simply, characteristics fast; Than chlorination 1-butyl-3-methylimidazole salt; Product is stronger to cellulosic solubility property; Production cost is lower, and ionic liquid can be realized reclaiming, demonstrates fully the Green Chemistry principle.
Embodiment
Embodiment 1
Adding 9 gram mass concentration are 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed; Drip the N-Methylimidazole of 9 grams while stirring; Control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization), and after reaction finished, using the N-Methylimidazole to regulate the pH value was 6.5.The ethanol that adds 20mL is made solvent, and the epoxy chloropropane of measuring 10 grams assembles instrument in tap funnel, with the oil bath heating, utilizes the constant temperature blender with magnetic force heating and stirs, and when solution temperature rises to 35 ℃, slowly drips epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation behind the accumulative total reaction times 3h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry 48h in 80 ℃ vacuum drying oven obtains faint yellow viscous liquid at last then, and calculated yield is 84.6%.
Embodiment 2
Adding 9 gram mass concentration are 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed; Drip the N-Methylimidazole of 9 grams while stirring; Control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization), and after reaction finished, using the N-Methylimidazole to regulate the pH value was 7.The ethanol that adds 20mL is made solvent, and the epoxy chloropropane of measuring 10 grams assembles instrument in tap funnel, with the oil bath heating, utilizes the constant temperature blender with magnetic force heating and stirs, and when solution temperature rises to 40 ℃, slowly drips epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation behind the accumulative total reaction times 3h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry 48h in 80 ℃ vacuum drying oven obtains faint yellow viscous liquid at last then, and calculated yield is 87.3%.
Embodiment 3
Adding 9 gram mass concentration are 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed; Drip 9 gram N-Methylimidazoles while stirring; Control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization), and after reaction finished, using the N-Methylimidazole to regulate the pH value was 7.The ethanol that adds 20mL is made solvent, and the epoxy chloropropane of measuring 10 grams assembles instrument in tap funnel, with the oil bath heating, utilizes the constant temperature blender with magnetic force heating and stirs, and when solution temperature rises to 60 ℃, slowly drips epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation behind the accumulative total reaction times 3h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry 48h in 80 ℃ vacuum drying oven obtains faint yellow viscous liquid at last then, and calculated yield is 86.9%.
Embodiment 4
Adding 9 gram mass concentration are 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed; Drip the N-Methylimidazole of 9 grams while stirring; Control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization), and after reaction finished, using the N-Methylimidazole to regulate the pH value was 7.The ethanol that adds 20mL is made solvent, and the epoxy chloropropane of measuring 10 grams assembles instrument in tap funnel, with the oil bath heating, utilizes the constant temperature blender with magnetic force heating and stirs, and when solution temperature rises to 80 ℃, slowly drips epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation behind the accumulative total reaction times 3h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry 48h in 80 ℃ vacuum drying oven obtains faint yellow viscous liquid at last then, and calculated yield is 86.4%.
Embodiment 5
Adding 9 gram mass concentration are 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed; Drip the N-Methylimidazole of 9 grams while stirring; Control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization), and after reaction finished, using the N-Methylimidazole to regulate the pH value was 6.The ethanol that adds 20mL is made solvent, and the epoxy chloropropane of measuring 10 grams assembles instrument in tap funnel, with the oil bath heating, utilizes the constant temperature blender with magnetic force heating and stirs, and when solution temperature rises to 40 ℃, slowly drips epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation behind the accumulative total reaction times 1h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry 48h in 80 ℃ vacuum drying oven obtains faint yellow viscous liquid at last then, and calculated yield is 83.4%.
Embodiment 6
Adding 9 gram mass concentration are 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed; Drip the N-Methylimidazole of 9 grams while stirring; Control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization), and after reaction finished, using the N-Methylimidazole to regulate the pH value was 7.The ethanol that adds 20mL is made solvent, and the epoxy chloropropane of measuring 10 grams assembles instrument in tap funnel, with the oil bath heating, utilizes the constant temperature blender with magnetic force heating and stirs, and when solution temperature rises to 45 ℃, slowly drips epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation behind the accumulative total reaction times 2h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry 48h in 80 ℃ vacuum drying oven obtains faint yellow viscous liquid at last then, and calculated yield is 83.9%.
Embodiment 7
Adding 9 gram mass concentration are 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed; Drip the N-Methylimidazole of 9 grams while stirring; Control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization), and after reaction finished, using the N-Methylimidazole to regulate the pH value was 7.The ethanol that adds 20mL is made solvent, and the epoxy chloropropane of measuring 10 grams assembles instrument in tap funnel, with the oil bath heating, utilizes the constant temperature blender with magnetic force heating and stirs, and when solution temperature rises to 50 ℃, slowly drips epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation behind the accumulative total reaction times 3h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry 48h in 80 ℃ vacuum drying oven obtains faint yellow viscous liquid at last then, and calculated yield is 88.5%.
Embodiment 8
Adding 9 gram mass concentration are 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed; Drip the N-Methylimidazole of 9 grams while stirring; Control reaction temperature is no more than 30 ℃ (preventing the hydrochloric acid volatilization), and after reaction finished, using the N-Methylimidazole to regulate the pH value was 6.The ethanol that adds 20mL is made solvent, and the epoxy chloropropane of measuring 10 grams assembles instrument in tap funnel, with the oil bath heating, utilizes the constant temperature blender with magnetic force heating and stirs, and when solution temperature rises to 48 ℃, slowly drips epoxy chloropropane.Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation behind the accumulative total reaction times 4h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, the remaining N-Methylimidazole of possibility is removed in extraction; Dry 48h in 80 ℃ vacuum drying oven obtains faint yellow viscous liquid at last then, and calculated yield is 85.1%.
Claims (3)
1.1-(3-chloro-2-hydroxypropyl)-3-Methylimidazole ionic liquid is characterized in that structural formula is following:
2. the said 1-of claim 1 (3-chloro-2-hydroxypropyl)-3-Methylimidazole preparation method of ionic liquid; It is characterized in that; Adding 6-10 mass parts mass concentration is 36% concentrated hydrochloric acid in the there-necked flask that whisking appliance, tap funnel and TM are housed, and drips the N-Methylimidazole of 6-10 mass parts while stirring, and control reaction temperature is no more than 30 ℃; Behind the reaction 1h, use the N-Methylimidazole to regulate the pH value and be 6-7; Add 10-17 mass parts ethanol and make solvent, the epoxy chloropropane of measuring the 5-12 mass parts assembles instrument in tap funnel; Heat with oil bath; Utilize constant temperature blender with magnetic force that flask is heated and stirring, when solution temperature rises to 30-80 ℃, slowly drip epoxy chloropropane; Dropwise, epoxy chloropropane, ethanol and water are removed in underpressure distillation after continuing to react 1-4h, are cooled to room temperature; As extraction agent, impose violent stirring with ether, remaining N-Methylimidazole is removed in extraction; Dry in 80 ℃ vacuum drying oven then, obtain faint yellow viscous liquid at last, promptly be 1-(3-chloro-2-hydroxypropyl)-3-Methylimidazole ionic liquid.
3. the said preparation method of claim 2 is characterized in that, said room temperature is 20-35 ℃.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110407820A (en) * | 2019-08-16 | 2019-11-05 | 韩山师范学院 | A kind of hydroxide 1- (2,3- glycidyl) -3- methyl piperidine functional ionic liquids, preparation method and purposes |
| CN110860311A (en) * | 2018-08-27 | 2020-03-06 | 东北林业大学 | Sulfonated cellulose-based ionic liquid catalyst and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798286A (en) * | 2009-12-25 | 2010-08-11 | 青岛科技大学 | 1-(3-chlorine-2-hydroxyl-propyl)-3-alkyl imidazole ionic liquid and preparation method thereof |
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- 2012-04-05 CN CN2012101066929A patent/CN102675208A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798286A (en) * | 2009-12-25 | 2010-08-11 | 青岛科技大学 | 1-(3-chlorine-2-hydroxyl-propyl)-3-alkyl imidazole ionic liquid and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| 《Ultrasonics Sonochemistry》 20080304 Sanhu Zhao et al. An atom-efficient and practical synthesis of new pyridinium ionic liquids and application in Morita-Baylis-Hillman reaction 955-959 1-3 第15卷, * |
| CHUNMING CHEN ET AL.: "Preparation of Cellulosic Ion Exchange Fiber Using an Ionic Liquid as Reaction Reagent and Medium", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
| CHUNMING CHEN: "A functionalised ionic liquid: 1-(3-chloro-2-hydroxypropyl)-3-methyl imidazolium chloride", 《PHYSICS AND CHEMISTRY OF LIQUIDS》 * |
| SANHU ZHAO ET AL.: "An atom-efficient and practical synthesis of new pyridinium ionic liquids and application in Morita–Baylis–Hillman reaction", 《ULTRASONICS SONOCHEMISTRY》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110860311A (en) * | 2018-08-27 | 2020-03-06 | 东北林业大学 | Sulfonated cellulose-based ionic liquid catalyst and preparation method thereof |
| CN110407820A (en) * | 2019-08-16 | 2019-11-05 | 韩山师范学院 | A kind of hydroxide 1- (2,3- glycidyl) -3- methyl piperidine functional ionic liquids, preparation method and purposes |
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Application publication date: 20120919 |