CN104744187A - Method for preparing alkene compound in microchannel reactor through aldehyde compound - Google Patents
Method for preparing alkene compound in microchannel reactor through aldehyde compound Download PDFInfo
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- CN104744187A CN104744187A CN201410111094.XA CN201410111094A CN104744187A CN 104744187 A CN104744187 A CN 104744187A CN 201410111094 A CN201410111094 A CN 201410111094A CN 104744187 A CN104744187 A CN 104744187A
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- microchannel reactor
- aldehyde
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- QRMPKOFEUHIBNM-UHFFFAOYSA-N CC1CCC(C)CC1 Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- ROSFUFIOLRQOON-UHFFFAOYSA-N CC1OC(C)OC1 Chemical compound CC1OC(C)OC1 ROSFUFIOLRQOON-UHFFFAOYSA-N 0.000 description 1
- 0 Cc(c(F)cc(*C**)c1)c1F Chemical compound Cc(c(F)cc(*C**)c1)c1F 0.000 description 1
- WJAVYWPXOXAOBS-UHFFFAOYSA-N Cc1cc(F)c(C)cc1 Chemical compound Cc1cc(F)c(C)cc1 WJAVYWPXOXAOBS-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Cc1ccc(C)cc1 Chemical compound Cc1ccc(C)cc1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a method for preparing an alkene compound in a microchannel reactor through an aldehyde compound. The method comprises the following steps: (1) respectively introducing tetrahydrofuran solution of the aldehyde compound and a wittig reagent into the microchannel reactor through a metering pump, and preheating; controlling the flow rate of the tetrahydrofuran solution and the wittig reagent, and synchronously entering the microchannel reactor respectively through the metering pump; (2) reacting the mixture in the microchannel reactor; and (3) obtaining a product. The method belongs to the technical field of organic synthesis application, and refers to a technological process of synthesizing alkene compound within short reaction time of scores of seconds to minutes by taking aldehyde compound as raw materials in the microchannel reactor. The alkene compound is obtained by introducing the materials into the alkene compoun through the metering pump, and then preheating, mixing and reacting as well as performing aftertreatment, and the method has the characteristics of being simple and safe to operate, high in yield, capable of accurately controlling the temperature, and reducing the side reaction, and the like, and the environment pollution of the technology is greatly decreased.
Description
Technical field
The present invention relates to the method utilizing micro passage reaction by prepared from aldehyde compounds vinyl compound, belong to organic synthesis applied technical field, be one be raw material with aldehyde compound in micro passage reaction, the technique of synthesis vinyl compound.
Background technology
Along with the development of the technology such as TN-LCD, STN-LCD and TF-LCD, the application of lcd technology in the production and life of people is more and more extensive.Response speed is improved in one of main development direction of current lcd technology, realizes the quick response of dynamic image, as liquid crystal display devices such as 3G mobile, computer and LCD TV.In order to improve corresponding speed, the viscosity reducing mixed liquid crystal becomes the Main way of liquid crystal material development.
Trans-4-substituted cyclohexyl olefin hydrocarbon liquid crystal compound has the excellent performance such as low viscosity, good mutual solubility and good photochemical stability, there is the viscosity reducing mixed liquid crystal, solve the mutual solubility problem of mixed liquid crystal system, quick response can be realized, improve the low-temperature stability of mixed liquid crystal, they have become the main component of high-grade TN-LCD, STN-LCD and TFT-LCD liquid crystal material.
The compound of the trans-4-substituted cyclohexyl olefin hydrocarbon liquid crystal compound of current widespread use mainly having structure:
Its synthetic route is as follows:
Normally in conventional reactor, prepare wittig reagent, rear temperature control drips the tetrahydrofuran solution of aldehyde, drips off rear stirring 0.5 ~ 8h.
The shortcoming of this production method is: because needs drip, there will be the uncontrolled situation of local temperature, cause by product to generate, and reacts completely to ensure simultaneously, and wittig reagent needs are excessive under normal circumstances, the waste of this raw material just caused.
Utilize micro passage reaction prepare vinyl compound synthesis technique once by, be a breakthrough of common process.Micro passage reaction generally refers to the small-sized reactive system manufactured through micro Process and precision processing technology.It comprises mixing tank, interchanger, reactor, controller etc. required for chemical unit, but the size of its pipeline is far smaller than conventional tube reactor, and microminiaturized structure makes it have some new characteristics.
Micro-reacting tcchnology is the emerging technology grown up the nineties in 20th century, replaces traditional reactor to have great advantage.Have excellent mass-and heat-transfer efficiency, online reacting weight is few, improves the security of dangerous chemical reaction, has great security for oxidation, the easily thermopositive reaction such as nitrated; Easy amplification, the R&D cycle is short, the achievement in research for lab scale directly can amplify production, does not have scale effect, has so namely saved the cost of research needed for iodine and time; Successive reaction instead of rhythmic reaction, and the condition of reaction is easy to control, and the reaction more for more complicated chemical reaction, by product has very large advantage, improves transformation efficiency and the selectivity of reaction.
Summary of the invention
The object of the present invention is to provide a kind of method utilizing micro passage reaction to carry out prepared from aldehyde compounds vinyl compound, the method can higher than under the reactor operating condition of normal temperature, rely on fluid kinetic energy own to complete mass-and heat-transfer, without the need to mechanical agitation process, to continue reaction process without the need to reaction channel outward and just can obtain productive rate higher than conventional reactor.Compared with the prior art comparatively, this technique has reaction conditions and accurately controls, reduce the discharge of organic liquid waste, continuous print mode is produced, and transformation efficiency is very high within the extremely short time, and decrease the formation of by product, in reaction process, avoid the fluctuation of temperature and concentration, without temperature runaway and superheating phenomenon, reaction process safety.
The application provides a kind of micro passage reaction that utilizes by the method for prepared from aldehyde compounds vinyl compound, it is characterized in that, comprises the following steps:
(1) tetrahydrofuran solution of aldehyde compound and wittig reagent passed in micro passage reaction respectively by volume pump and carry out preheating, design temperature is-10 ~ 60 DEG C; The flow velocity of the tetrahydrofuran solution and wittig reagent that control described aldehyde compound is 0.01 ~ 60L/min, and the velocity ratio of the tetrahydrofuran solution of described aldehyde compound and described wittig reagent is 1:1 ~ 1:10, synchronously enter in described micro passage reaction via respective volume pump and mix, mixing temperature is-10 ~ 60 DEG C;
(2) mixture of step (1) reacts in micro passage reaction, and in described micro passage reaction, reaction time is 10 ~ 300s, and temperature of reaction is-10 ~ 70 DEG C;
(3) product is obtained in described micro passage reaction outlet.
In some embodiments, described in step (1), flow velocity is 0.02-40L/min.
In some embodiments, in step (2), reaction process reaction time in micro passage reaction is 20 ~ 100s, and temperature of reaction is-5 ~ 60 DEG C.
In some embodiments, described aldehyde compound is the compound of following formula I:
Wherein,
R
1represent that H, F, carbonatoms be the alkyl of 1-7 or carbonatoms are the thiazolinyl of 2-7;
with
identical or different, represent independently of one another
or
M and n is identical or different, represents 0 or 1 independently of one another.
In some embodiments, described vinyl compound is the compound of following formula II:
Wherein,
R
2expression H, carbonatoms are the alkyl of 1-3.
The present invention has following advantage compared with prior art:
1. this reaction process is continuous flowing reaction, and the reaction times shortens to several seconds to several minutes, improves productive rate, significantly improves reaction efficiency and production efficiency.
2. raw material mixes splendid in microchannel, and temperature accurately controls, and without the need to convention stir process, thus simplify reactor structure, reduce power consumption.
3. in utilized conversion unit micro passage reaction, mass transfer enhancement type passage can strengthen mass transfer, heat transfer property, keeps temperature of reaction constant, avoids temperature runaway phenomenon, reduce the generation of by product.
4., in micro passage reaction, omnidistance from charging, preheating, mixing and reaction process is Continuous Flow reaction, and avoid the leakage needing in Conventional batch reaction to occur in additional configuration device and transfer, Environmental Safety, production efficiency is high.
Accompanying drawing explanation
Fig. 1 is that the present invention prepares vinyl compound reaction process schema.
Embodiment
The foregoing describe the present invention, the illustrative explanation of following examples implementation result of the present invention, can not be interpreted as limiting the scope of the invention.
The following example system carries out in microreactor according to the requirement of the inventive method.In following examples, the methyltriphenylphosphonium bromide used, ethyltriphenylphosphonium bromide and remaining compound monomer and related reagent all can be buied from market.
With reference to the process flow sheet of the present invention in Fig. 1, the mixture that aldehyde compound and solvents tetrahydrofurane are mixed with and the wittig reagent prepared in convention stir formula reactor are carried by volume pump A, B simultaneously respectively, first through heat exchange module, after through mixing module, react in reaction module after mixing in micro passage reaction, it is thermal oil that heat changes medium.After reaction for some time, product flows out from the outlet of reactor, after heat exchange module cooling, carries out aftertreatment.
Embodiment 1
(1) in a container, take a1236g, add tetrahydrofuran (THF) and dissolve, determine that final volume is 500mL.
(2) in 2L glass reactor, 358g methyltriphenylphosphonium bromide and appropriate tetrahydrofuran (THF) is added; nitrogen protection, adds potassium tert.-butoxide 109.8g in 0 ~ 5 DEG C under stirring, reinforced complete stirring 0.5h; final volume is 500mL, and namely nitrogen protection has prepared wittig reagent.
(3) squeeze in micro passage reaction by two Sets of Measurement pumps respectively, flow velocity is 0.02mL/min, preheating is carried out through warm-up block, then enter mixing module to react, in mixing module after the raw reaction of hybrid concurrency, continue into a series of reaction module, after having reacted, product flows out from the outlet of reactor, then through overcooling aftertreatment.The reaction time of reaction process in micro passage reaction is 90s, and temperature of reaction is 15 DEG C.
(4) by cooled reaction solution separatory, organic phase anhydrous sodium sulfate drying 0.5h, steam solvent, remaining solid Petroleum ether extraction, filter, filtrate is through silica column purification (sherwood oil is elutriant), steam solvent, obtain final product b1225.7g, utilize gas chromatographic analysis purity to be 99.5%, mp:31.1 ~ 32.5 DEG C; MS(EI): m/z234 (M+).
Embodiment 2
(1) in a container, take a1236kg, add tetrahydrofuran (THF) and dissolve, determine that final volume is 500L.
(2) in 1000L tank reactor, 372kg ethyltriphenylphosphonium bromide and appropriate tetrahydrofuran (THF) is added; nitrogen protection, adds potassium tert.-butoxide 110kg in 0 ~ 5 DEG C under stirring, reinforced complete stirring 0.5h; final volume is 500L, and namely nitrogen protection has prepared wittig reagent.
(3) squeeze in micro passage reaction by two Sets of Measurement pumps respectively, flow velocity is 30L/min and carries out preheating through warm-up block, then enter mixing module to react, in mixing module after the raw reaction of hybrid concurrency, continue into a series of reaction module, after having reacted, product flows out from the outlet of reactor, then through overcooling aftertreatment.The reaction time of reaction process in micro passage reaction is 60s, and temperature of reaction is-5 DEG C.
(4) by cooled reaction solution separatory, organic phase anhydrous sodium sulfate drying 0.5h, steam solvent, remaining solid Petroleum ether extraction, filter, filtrate is through silica column purification (sherwood oil is elutriant), steam solvent, obtain final product b2237.3kg, utilize gas chromatographic analysis purity to be 99.3%, mp:41.3 ~ 43.5 DEG C; MS(EI): m/z248 (M+).
Embodiment 3
(1) in a container, take a3306g, add tetrahydrofuran (THF) and dissolve, determine that final volume is 500mL.
(2) in 2L glass reactor, 358g methyltriphenylphosphonium bromide and appropriate tetrahydrofuran (THF) is added; nitrogen protection, adds potassium tert.-butoxide 109.8g in 0 ~ 5 DEG C under stirring, reinforced complete stirring 0.5h; final volume is 500mL, and namely nitrogen protection has prepared wittig reagent.
(3) squeeze in micro passage reaction by two Sets of Measurement pumps respectively, flow velocity is 0.04mL/min and carries out preheating through warm-up block, then enter mixing module to react, in mixing module after the raw reaction of hybrid concurrency, continue into a series of reaction module, after having reacted, product flows out from the outlet of reactor, then through overcooling aftertreatment.The reaction time of reaction process in micro passage reaction is 45s, and temperature of reaction is 55 DEG C.
(4) by cooled reaction solution separatory, organic phase anhydrous sodium sulfate drying 0.5h, steam solvent, remaining solid Petroleum ether extraction, filter, filtrate is through silica column purification (sherwood oil is elutriant), steam solvent, obtain final product b3300.6g, utilize gas chromatographic analysis purity to be 99.1%, mp:43.6 ~ 45.5 DEG C; MS(EI): m/z304 (M+).
Embodiment 4
(1) in a container, take a4284g, add tetrahydrofuran (THF) and dissolve, determine that final volume is 500mL.
(2) in 2L glass reactor, 358g methyltriphenylphosphonium bromide and appropriate tetrahydrofuran (THF) is added; nitrogen protection, adds potassium tert.-butoxide 109.8g in 0 ~ 5 DEG C under stirring, reinforced complete stirring 0.5h; final volume is 500mL, and namely nitrogen protection has prepared wittig reagent.
(3) squeeze in micro passage reaction by two Sets of Measurement pumps respectively, flow velocity is 0.025L/min and carries out preheating through warm-up block, then enter mixing module to react, in mixing module after the raw reaction of hybrid concurrency, continue into a series of reaction module, after having reacted, product flows out from the outlet of reactor, then through overcooling aftertreatment.The reaction time of reaction process in micro passage reaction is 72s, and temperature of reaction is 35 DEG C.
(4) by cooled reaction solution separatory, organic phase anhydrous sodium sulfate drying 0.5h, steam solvent, remaining solid Petroleum ether extraction, filter, filtrate is through silica column purification (sherwood oil is elutriant), steam solvent, obtain final product b4270.1g, utilize gas chromatographic analysis purity to be 99.1%, mp:64.0 ~ 66.5 DEG C; MS(EI): m/z282 (M+).
Embodiment 5
(1) in a container, take a5264g, add tetrahydrofuran (THF) and dissolve, determine that final volume is 500mL.
(2) in 2L glass reactor, 358g methyltriphenylphosphonium bromide and appropriate tetrahydrofuran (THF) is added; nitrogen protection, adds potassium tert.-butoxide 109.8g in 0 ~ 5 DEG C under stirring, reinforced complete stirring 0.5h; final volume is 500mL, and namely nitrogen protection has prepared wittig reagent.
(3) squeeze in micro passage reaction by two Sets of Measurement pumps respectively, flow velocity is 0.02L/min and carries out preheating through warm-up block, then enter mixing module to react, in mixing module after the raw reaction of hybrid concurrency, continue into a series of reaction module, after having reacted, product flows out from the outlet of reactor, then through overcooling aftertreatment.The reaction time of reaction process in micro passage reaction is 90s, and temperature of reaction is 45 DEG C.
(4) by cooled reaction solution separatory, organic phase anhydrous sodium sulfate drying 0.5h, steam solvent, remaining solid Petroleum ether extraction, filter, filtrate is through silica column purification (sherwood oil is elutriant), steam solvent, obtain final product b5251.7g, utilize gas chromatographic analysis purity to be 98.9%, mp:50.1 ~ 52.5 DEG C; MS(EI): m/z262 (M+).
Embodiment 6
(1) in a container, take a6266g, add tetrahydrofuran (THF) and dissolve, determine that final volume is 300mL.
(2) in 2L glass reactor, 358g methyltriphenylphosphonium bromide and appropriate tetrahydrofuran (THF) is added; nitrogen protection, adds potassium tert.-butoxide 109.8g in 0 ~ 5 DEG C under stirring, reinforced complete stirring 0.5h; final volume is 1500mL, and namely nitrogen protection has prepared wittig reagent.
(3) squeeze in micro passage reaction by two Sets of Measurement pumps respectively, flow velocity is respectively 0.02L/min and 0.1L/min, preheating is carried out through warm-up block, then enter mixing module to react, in mixing module after the raw reaction of hybrid concurrency, continue into a series of reaction module, after having reacted, product flows out from the outlet of reactor, then through overcooling aftertreatment.The reaction time of reaction process in micro passage reaction is 105s, and temperature of reaction is 0 DEG C.
(4) by cooled reaction solution separatory, organic phase anhydrous sodium sulfate drying 0.5h, steam solvent, remaining solid Petroleum ether extraction, filter, filtrate is through silica column purification (sherwood oil is elutriant), steam solvent, obtain final product b6255.7g, utilize gas chromatographic analysis purity to be 98.9%, mp:54.1 ~ 56.5 DEG C; MS(EI): m/z264 (M+).
Claims (7)
1. utilize micro passage reaction by a method for prepared from aldehyde compounds vinyl compound, it is characterized in that, comprise the following steps:
(1) tetrahydrofuran solution of aldehyde compound and wittig reagent passed in micro passage reaction respectively by volume pump and carry out preheating, design temperature is-10 ~ 60 DEG C; The flow velocity of the tetrahydrofuran solution and wittig reagent that control described aldehyde compound is 0.01 ~ 60L/min, and the velocity ratio of the tetrahydrofuran solution of described aldehyde compound and described wittig reagent is 1:1 ~ 1:10, synchronously enter in described micro passage reaction via respective volume pump and mix, mixing temperature is-10 ~ 60 DEG C;
(2) mixture of step (1) reacts in micro passage reaction, and in described micro passage reaction, reaction time is 10 ~ 300s, and temperature of reaction is-10 ~ 70 DEG C;
(3) product is obtained in described micro passage reaction outlet.
2. method according to claim 1, is characterized in that, wherein described in step (1), flow velocity is 0.02-40L/min.
3. method according to claim 1, is characterized in that, wherein in step (2), reaction process reaction time in micro passage reaction is 20 ~ 100s, and temperature of reaction is-5 ~ 60 DEG C.
4. method according to claim 1, is characterized in that, wherein said aldehyde compound is the compound of following formula I:
Wherein,
R
1represent that H, F, carbonatoms be the alkyl of 1-7 or carbonatoms are the thiazolinyl of 2-7;
with
identical or different, represent independently of one another
or
M and n is identical or different, represents 0 or 1 independently of one another.
5. method according to claim 4, is characterized in that, described vinyl compound is the compound of following formula II:
Wherein,
R
2expression H, carbonatoms are the alkyl of 1-3.
6. method according to claim 4, is characterized in that, the compound of described formula I is selected from following compound:
7. method according to claim 5, is characterized in that, the compound of described formula II is selected from following compound:
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106631694A (en) * | 2016-11-22 | 2017-05-10 | 李晖 | Preparation method of 2,2,3,3-tetrafluoropropanol |
| CN106673957A (en) * | 2016-11-22 | 2017-05-17 | 李晖 | Preparation method of 2,2,3,4,4,4-hexafluoro-1-butyl alcohol |
| CN108559526A (en) * | 2018-06-06 | 2018-09-21 | 江苏创拓新材料有限公司 | The preparation method of high-purity liquid crystal monomer containing double bond |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106631694A (en) * | 2016-11-22 | 2017-05-10 | 李晖 | Preparation method of 2,2,3,3-tetrafluoropropanol |
| CN106673957A (en) * | 2016-11-22 | 2017-05-17 | 李晖 | Preparation method of 2,2,3,4,4,4-hexafluoro-1-butyl alcohol |
| CN106631694B (en) * | 2016-11-22 | 2019-08-09 | 李晖 | A kind of preparation method of 2,2,3,3- tetrafluoropropanol |
| CN106673957B (en) * | 2016-11-22 | 2019-08-09 | 李晖 | A kind of preparation method of 2,2,3,4,4,4- hexafluoro-n-butyl alcohol |
| CN108559526A (en) * | 2018-06-06 | 2018-09-21 | 江苏创拓新材料有限公司 | The preparation method of high-purity liquid crystal monomer containing double bond |
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