CN107698514A - A kind of preparation method of the methylimidazole bromide of 1 butyl 3 - Google Patents
A kind of preparation method of the methylimidazole bromide of 1 butyl 3 Download PDFInfo
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- CN107698514A CN107698514A CN201711191548.9A CN201711191548A CN107698514A CN 107698514 A CN107698514 A CN 107698514A CN 201711191548 A CN201711191548 A CN 201711191548A CN 107698514 A CN107698514 A CN 107698514A
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- butyl
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- ethyl acetate
- methylimidazoles
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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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- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a kind of preparation method of the methylimidazole bromide of 1 butyl 3, reacted by NBB with N methylimidazoles by heating stirring, then crystalline product is obtained by adding ethyl acetate, centrifuged, eluted by ethyl acetate again, then unnecessary ethyl acetate is removed by vacuum revolving, that is, obtains the methylimidazole bromide of 1 butyl 3.Preparation method of the present invention is reduced the accumulation of N methylimidazoles in unreacting material early stage, is avoided the generation of temperature runaway, add safety coefficient by the control to temperature；The abundant reaction of raw material is also ensure that simultaneously, adds yield；The blowing under the conditions of 45~55 DEG C, it both ensure that product was completely in crystalline state and it also avoid product and can not smoothly have been released by discharging opening because of caking；Operating time is short, high income, substantially increases production efficiency, reduces production cost.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of preparation side of 1- butyl -3- methylimidazole bromides
Method.
Technical background
Ionic liquid is made up of organic cation and organic anion/inorganic anion, it have some unique physics,
Chemical property, such as non-volatility, nonflammable, higher boiling, reusable edible, there is high thermo-chemical stability, chemical stability
And stronger solubility property.
It is white crystal particle under 1- butyl -3- methy limidazolium normal temperature, is a kind of relatively broad ionic liquid of purposes
Body, using extremely wide especially in pharmaceutical intermediate field.The prior synthesizing method of 1- butyl -3- methy limidazoliums is big
Part is solvent reflux extraction, and 1,1, the 1- trichloroethanes that these methods are used in preparation process is respectively provided with to environment and human body
Larger harm, with the fast development of science and technology, the preparation method of 1- butyl -3- methy limidazoliums has also obtained quick hair
Exhibition, have a variety of preparation technologies on 1- butyl -3- methy limidazoliums in this field, but in existing preparation technology
In there are still there is more technical problem not solved preferably；In preparation process, particularly in large batch of industry
There are still have in metaplasia production：Technique short time consumption is grown, and the defects of easily luming, turn yellow in preparation process, reduces production efficiency,
Improve production cost.
The content of the invention
In order to solve the above problems, the invention provides a kind of preparation method of 1- butyl -3- methylimidazole bromides, the party
Method takes short, efficiency high, is not in caking phenomenon in production process, and good product quality.
The present invention is achieved by the following technical solutions
A kind of preparation method of 1- butyl -3- methylimidazole bromides, this method comprise the following steps：
(1) take reaction raw materials NBB to add in reactor, to reaction raw materials heating, be warming up to 55~60 DEG C；
(2) after step (1) the raw material heating stirring, heating is closed, N- methylimidazoles are added dropwise into reactor,；
(3) after step (2) the N- methylimidazoles are added dropwise, temperature control is continued to stir under the conditions of 80~90 DEG C
50~70min, ethyl acetate is added after the completion of stirring, material in reactor is cooled, continues stirring until in reactor
Greenhouse cooling to 45~55 DEG C (having white crystal precipitation), that is, complete reaction；
(4) after the completion of step (3) described reaction, the material in reactor (is discharged by blowing in reactor during blowing
Temperature is 45~55 DEG C), be delivered to centrifuge, elution, centrifugation, obtain white solid；
(5) by the white solid obtained after step (4) elution, centrifugation, vacuum rotates under the conditions of 40~50 DEG C, removes
Remnants ethyl acetate is gone to obtain described 1- butyl -3- methy limidazolium white solid particles.
The preparation method of described 1- butyl -3- methylimidazole bromides, described reactor are with reaction dress with dissection
Put, heated in the heating process described in step (1) using water-bath, hot water is passed through into interlayer；Described pair of reaction of step (3)
When material is cooled in kettle, cooled by being passed through running water into interlayer；Can when adding NBB into reactor
NBB is added in a manner of using and vacuumize.
The preparation method of described 1- butyl -3- methylimidazole bromides, the NBB added in reactor and N- first
The mass ratio of base imidazoles is 1.8~2.0：1.
The preparation method of described 1- butyl -3- methylimidazole bromides, used in step (2) the dropwise addition N- methylimidazoles
Time is 4~5 hours.
The preparation method of described 1- butyl -3- methylimidazole bromides, the addition and step of step (3) described ethyl acetate
Suddenly the ratio between addition of (1) described NBB is (1~1.5) L：2kg.
The preparation method of described 1- butyl -3- methylimidazole bromides, step (4) leacheate used is acetic acid second
Ester, described elution, centrifugation are to be completed simultaneously using the centrifuge that charge door is carried on lid.Use on lid with charging
Mouthful centrifuge, become add ethyl acetate eluted, side centrifugation, washing is more thoroughly and when reducing the operation of whole technique
Between, improve production efficiency.
The preparation method of described 1- butyl -3- methylimidazole bromides, the rotating speed of the centrifuge is 300~500r/
min。
The preparation method of described 1- butyl -3- methylimidazole bromides, the vacuum described in step (5) use during rotating
Vacuum be (- 0.07~-0.095) MPa.
Compared with prior art, the present invention has following positive beneficial effect
Preparation method of the present invention reduces N- methylimidazoles in unreacting material early stage by the control to temperature
Accumulation, avoid the generation of temperature runaway, add safety coefficient；The abundant reaction of raw material is also ensure that simultaneously, adds yield；
Blowing under the conditions of 45~55 DEG C, both ensure that product is completely in crystalline state and it also avoid product can not be by because of caking
Discharging opening is smoothly released；
The preparation method operating time of the present invention is short, high income, substantially increases production efficiency, reduces and be produced into
This；
Preparation technology of the present invention, raw material are directly delivered in centrifuge by conveyance conduit after releasing and centrifuged,
The processing mode carried out simultaneously using elution, centrifugation during centrifugation, shortens processing time, and decrease long time treatment mistake
Influence of the volatile ingredient to human body and environment in journey, reduces the input of manpower and materials in processing procedure, improves production efficiency,
Reduce production cost.
Embodiment
The present invention is described in more details below by embodiment, but is not intended to limit the invention
Protection domain.
Embodiment 1
A kind of preparation method of 1- butyl -3- methylimidazole bromides, this method comprise the following steps：
(1) reaction raw materials NBB 41.7Kg is taken to add in 80L reactors, by being passed through water-bath in the interlayer to reactor
NBB is heated, until being warming up to 55~60 DEG C；
(2) after step (1) the raw material heating stirring, close heating water bath and 22.5Kg is added dropwise into reactor
N- methylimidazoles, it is added dropwise within 4.5 hours；
(3) after step (2) the N- methylimidazoles are added dropwise, temperature control is continued to stir under the conditions of 80~90 DEG C
60min, adds ethyl acetate 25L after the completion of stirring, cooled by being passed through running water into interlayer and continue stirring until
The greenhouse cooling of reactor completes reaction to 45~55 DEG C；Then by reactor discharging opening blowing (temperature of discharging be 45~
55℃)；The material of releasing is delivered to the centrifuge that charge door is carried on lid by material conveying pipe, then passes through centrifuge cup
Charge door on son adds ethyl acetate and the material of releasing is washed, centrifuges that (rotating speed of centrifuge is 400r/ in washing
Min), washing obtains white solid after finishing and (finishing the washing of unreacted raw material)；
(4) by the white solid obtained after step (3) elution, centrifugation, vacuum revolving is (true under the conditions of 40~50 DEG C
Vacuum during sky revolving is -0.09MPa), the ethyl acetate for removing remnants obtains described 1- butyl -3- methyl bromides
Change imidazoles white solid particle.
After testing, the yield of products obtained therefrom is：95.15%；Purity is that 99.94% its water content is 1900ppm；That is the party
Product prepared by method has higher yield and purity, and water content friendship is low, meets the requirements.
Embodiment 2
A kind of preparation method of 1- butyl -3- methylimidazole bromides, this method comprise the following steps：
(1) reaction raw materials NBB 30Kg is taken to add in 80L reactors, by being passed through water-bath pair in the interlayer to reactor
NBB in reactor is heated, until being warming up to 55~60 DEG C；
(2) after step (1) the raw material heating stirring, close heating water bath and 16Kg N- are added dropwise into reactor
Methylimidazole, it is added dropwise within 4 hours；
(3) after step (2) the N- methylimidazoles are added dropwise, temperature control is continued to stir under the conditions of 80~90 DEG C
50min, adds ethyl acetate 16L after the completion of stirring, cooled by being passed through running water into reactor interlayer and continue to stir
Mix until the greenhouse cooling of reactor is to 45~55 DEG C, i.e. completion is reacted；Then by the reactor discharging opening blowing (temperature of discharging
For 45~55 DEG C)；Releasing material by material conveying pipe be delivered on lid with charge door centrifuge, then by from
Charge door on scheming lid adds ethyl acetate and is washed, centrifuged in washing that (rotating speed of centrifuge is to the material of releasing
350r/min), washing obtains white solid after finishing and (finishing the washing of unreacted raw material)；
(4) by the white solid obtained after step (3) elution, centrifugation, vacuum revolving is (true under the conditions of 40~50 DEG C
Vacuum during sky revolving is -0.08MPa), the ethyl acetate for removing remnants obtains described 1- butyl -3- methyl bromides
Change imidazoles white solid particle.
After testing, the yield of products obtained therefrom is 96.23%；Purity is that 99.80% its water content is 1660ppm；That is the party
Product prepared by method has higher yield and purity, and water content friendship is low, meets the requirements.
Embodiment 3
A kind of preparation method of 1- butyl -3- methy limidazoliums, this method comprise the following steps：
(1) reaction raw materials NBB 50Kg is taken to add in 300L reactors, by being passed through water-bath in the interlayer to reactor
NBB in reactor is heated, until being warming up to 55~60 DEG C；
(2) after step (1) the raw material heating stirring, close heating water bath and 27.8Kg is added dropwise into reactor
N- methylimidazoles, it is added dropwise within 5 hours；
(3) after step (2) the N- methylimidazoles are added dropwise, continue to stir 70min, stirring under the conditions of 80~90 DEG C
After the completion of add ethyl acetate 37.5L, cooled by being passed through running water into interlayer and continue stirring until in reactor
Greenhouse cooling to 45~55 DEG C, that is, complete reaction；Then by reactor discharging opening blowing, (temperature during discharging is 45~55
℃)；The material of releasing is delivered to the centrifuge that charge door is carried on lid by material conveying pipe, then passes through centrifuge lid
On charge door add ethyl acetate the material of releasing washed, centrifuges that (rotating speed of centrifuge is 500r/ in washing
Min), washing obtains white solid after finishing and (finishing the washing of unreacted raw material)；
(4) by the white solid obtained after step (3) elution, centrifugation, vacuum revolving is (true under the conditions of 40~50 DEG C
Vacuum during sky revolving is -0.095MPa), the ethyl acetate for removing remnants obtains described 1- butyl -3- methyl
Limidazolium white solid particle.
After testing, the yield of products obtained therefrom is 93.16；Purity is that 99.06% its water content is 1200ppm；That is this method
The product of preparation has higher yield and purity, and water content is low, meets the requirements.
Claims (9)
1. a kind of preparation method of 1- butyl -3- methylimidazole bromides, it is characterised in that this method comprises the following steps：
(1) take reaction raw materials NBB to add in reactor, to reaction raw materials heating, be warming up to 55~60 DEG C；
(2) after step (1) the raw material heating stirring, close heating and N- methylimidazoles are added dropwise into reactor；
(3) after step (2) the N- methylimidazoles are added dropwise, continue 50~70min of stirring under the conditions of 80~90 DEG C, stir
After the completion of add ethyl acetate, the material in reactor is cooled, continue stirring until reactor in greenhouse cooling extremely
45~55 DEG C, that is, complete reaction；
(4) after the completion of step (3) described reaction, by the material in reactor by reactor drain hole blowing, be delivered to centrifuge,
Elution, centrifugation, obtain white solid；
(5) by step (4) is described eluted using ethyl acetate after white solid under the conditions of 40~50 DEG C vacuum rotate, remove
Remnants ethyl acetate is gone to obtain described 1- butyl -3- methy limidazolium white solid particles.
2. the preparation method of 1- butyl -3- methylimidazole bromides according to claim 1, it is characterised in that the addition
The mass ratio of NBB and N- methylimidazoles in reactor is 1.8~2.0：1.
3. the preparation method of 1- butyl -3- methylimidazole bromides according to claim 1, it is characterised in that step (1) institute
It is heating water bath to state to the mode of reaction raw materials heating.
4. the preparation method of 1- butyl -3- methylimidazole bromides according to claim 1, it is characterised in that step (2) institute
State N- methylimidazoles and the time used is added dropwise as 4~5 hours.
5. the preparation method of 1- butyl -3- methylimidazole bromides according to claim 1, it is characterised in that step (3) institute
It is (1~1.5) L to state the ratio between the addition of ethyl acetate and the addition of step (1) described NBB：2kg.
6. the preparation method of 1- butyl -3- methylimidazole bromides according to claim 1, it is characterised in that step (3) institute
The medium used during cooling is stated as running water.
7. the preparation method of 1- butyl -3- methylimidazole bromides according to claim 1, it is characterised in that step (4) institute
The leacheate used is stated as ethyl acetate；Described elution, centrifugation are to be eluted using the centrifuge side that charge door is carried on lid
Side is heated, and elution is completed simultaneously with centrifugation.
8. the preparation method of the 1- butyl -3- methylimidazole bromides according to claim 1 or 7, it is characterised in that it is described from
The rotating speed of scheming is 300~500r/min.
9. the preparation method of 1- butyl -3- methy limidazoliums according to claim 1, it is characterised in that step (4) institute
It is 45~55 DEG C to state the temperature to be discharged during blowing.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711191548.9A CN107698514A (en) | 2017-11-24 | 2017-11-24 | A kind of preparation method of the methylimidazole bromide of 1 butyl 3 |
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| CN201711191548.9A CN107698514A (en) | 2017-11-24 | 2017-11-24 | A kind of preparation method of the methylimidazole bromide of 1 butyl 3 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010668A (en) * | 2022-06-07 | 2022-09-06 | 林州市科能材料科技有限公司 | Preparation method of 1-ethyl-3-methylimidazole chloride salt |
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|---|---|---|---|---|
| CN102086041A (en) * | 2010-12-08 | 2011-06-08 | 华东理工大学 | Refining and comprehensive utilization method of waste sodium chloride generated in potash fertilizer production |
| CN102351796A (en) * | 2011-08-23 | 2012-02-15 | 林州市科能材料科技有限公司 | Production process of imidazole ionic liquid |
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2017
- 2017-11-24 CN CN201711191548.9A patent/CN107698514A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102086041A (en) * | 2010-12-08 | 2011-06-08 | 华东理工大学 | Refining and comprehensive utilization method of waste sodium chloride generated in potash fertilizer production |
| CN102351796A (en) * | 2011-08-23 | 2012-02-15 | 林州市科能材料科技有限公司 | Production process of imidazole ionic liquid |
Non-Patent Citations (1)
| Title |
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| 万恒等: "咪唑类离子液体制备工艺的优化", 《安徽化工》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010668A (en) * | 2022-06-07 | 2022-09-06 | 林州市科能材料科技有限公司 | Preparation method of 1-ethyl-3-methylimidazole chloride salt |
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