CN110642671B - System and method for continuously preparing Grignard reagent to synthesize phenethyl alcohol - Google Patents
System and method for continuously preparing Grignard reagent to synthesize phenethyl alcohol Download PDFInfo
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- C07C29/68—Preparation of metal alcoholates
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B49/00—Grignard reactions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/02—Magnesium compounds
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Abstract
The invention relates to a system and a method for continuously preparing Grignard reagent and synthesizing phenethyl alcohol, wherein the system comprises a tower reactor for continuously preparing Grignard reagent by reacting chlorobenzene compound solution with magnesium, the tower reactor is divided into a plurality of reaction areas along the height direction by partition plates, each divided area is internally provided with a plurality of layers of stirring paddles, and the system also comprises a Grignard reaction kettle, a falling film scraper evaporator, an enamel reaction kettle, a continuous delayer, an extractor and a rectifying tower; the magnesium and chlorobenzene flow in a tower reactor in a counter-current manner, the reaction is completed in the flowing process, unreacted magnesium mud is removed through settling separation to obtain Grignard reagent reaction liquid, and the Grignard reagent reaction liquid is mixed with an ethylene oxide solution for reaction to obtain the substituted phenethyl alcohol. Compared with the prior art, the method has the advantages of stable raw material adding speed, stable heat generated by reaction, capability of avoiding the risk of reaction out of control due to large instant heat release, greatly improved safety, avoidance of back mixing, greatly improved selectivity and suitability for industrial production.
Description
Technical Field
The invention belongs to the field of flavors and fragrances, and relates to a method for continuously preparing a Grignard reagent synthesized phenethyl alcohol.
Background
Phenethyl alcohol, also known as 2-phenethyl alcohol, has a molecular formula: c 8 H 10 O, the molecular structural formula of which is shown in formula (I):
the phenethyl alcohol is one of the most important spices in aromatics, has elegant and delicate rose fragrance, has mild and sweet fragrance, is mainly used for preparing rose, caramel, honey and other fruity food essences as well as various wine essences and tobacco essences, is also an indispensable substance in rose and other plant flavors, and can be specially used for spices such as soap and the like due to the stability to alkali.
At present, the literature for synthesizing the phenethyl alcohol is more (CN1465557A, US2125490A and US2483323A), the benzene-ethylene oxide method utilizes Friedel-Crafts reaction to synthesize the phenethyl alcohol, the investment of the method is small, the equipment requirement is low, but side reactions are more, the selectivity is poor, a large amount of benzene-containing acidic wastewater is produced, and the yield is generally 40-65%; the benzene-ethylene oxide method has high yield of synthesizing phenethyl alcohol by utilizing Grignard reagents, but has low production efficiency of batch reaction and low safety.
The reaction equation is as follows:
disclosure of Invention
The present invention is directed to overcoming the above-mentioned drawbacks of the prior art and providing a system and a method for continuously preparing grignard reagent synthesized phenylethanol.
The purpose of the invention can be realized by the following technical scheme:
the invention provides a system for continuously preparing Grignard reagent and synthesizing phenethyl alcohol, which comprises a tower reactor for continuously preparing Grignard reagent by reacting chlorobenzene compound solution with magnesium, wherein the tower reactor is divided into a plurality of reaction areas by partition plates along the height direction, and a plurality of layers of stirring paddles are arranged in each divided area.
The partition plates in the invention have the function of separating reaction liquid on two sides of the partition plates so as to reduce the back mixing of materials between the partition plates; the stirring paddle is used for enabling the reaction liquid in each divided area to achieve a complete mixing effect.
As a preferred technical scheme of the invention, the chlorobenzene compound solution enters the tower reactor from the bottom of the tower, magnesium (preferably magnesium powder) enters the tower reactor from the top of the tower, the chlorobenzene compound solution and the magnesium are in countercurrent contact in the tower reactor, and the Grignard reaction solution flows out from the top of the tower.
As a preferable technical scheme of the invention, a cooling coil is arranged in each reaction area of the tower reactor, and a cooling jacket is arranged outside each reaction area of the tower reactor.
As a preferred technical scheme of the invention, the top of the tower reactor is provided with a reflux cooler.
As the preferred technical scheme of the invention, the system also comprises a lattice reaction kettle, a falling film scraper evaporator, an enamel reaction kettle, a continuous layering device, an extractor and a rectifying tower;
the lattice reaction kettle is used for the continuous inflow of an ethylene oxide solution and a lattice reaction liquid flowing out of the tower reactor and the reaction under the cooling condition,
the falling film scraper evaporator is used for continuously concentrating reaction liquid flowing out of the grid type reaction kettle and continuously recovering a solvent,
the enamel reaction kettle is used for continuous inflow of a hydrochloric acid solution and a concentrated reaction solution of the lattice reaction kettle, and neutralization under the conditions of cooling and stirring,
the continuous delayer is used for continuously flowing the effluent liquid of the enamel reaction kettle and delaminating the organic phase and the water phase in the effluent liquid of the enamel reaction kettle,
the extractor is used for the continuous inflow of the water phase and the continuous extraction of the reaction product in the water phase through the continuous inflow of toluene,
the rectifying tower is used for continuously flowing in an organic phase and an extraction liquid and obtaining a reaction product through rectification.
The invention also provides a method for continuously preparing the Grignard reagent to synthesize the phenethyl alcohol, and the method comprises the step of continuously preparing the Grignard reagent in the tower reactor by using the chlorobenzene compound solution and magnesium.
As a preferable technical scheme of the invention, the method also comprises the step of continuously reacting the Grignard reagent with an ethylene oxide solution to prepare the phenethyl alcohol magnesium salt, and the phenethyl alcohol magnesium salt is neutralized, layered and rectified to obtain the phenethyl alcohol.
The invention is the preferable technical proposal;
before continuously preparing the Grignard reagent, preparing a Grignard reagent solution with the volume of 60-90% of that of the tower reactor as a bottom material, and keeping enough magnesium for reaction for 1-5 hours in the tower reactor (so as to maintain the excess of magnesium in the continuous reaction process);
the continuous preparation of the grignard reagent was carried out under reflux conditions.
As a preferable technical scheme of the invention, the chlorobenzene compound solution is 10-30 wt% of tetrahydrofuran solution of chlorobenzene compound, the chlorobenzene compound solution and magnesium quantitatively and continuously enter a tower reactor, and the ratio of the benzene compound solution to the magnesium is controlled to enable the magnesium to be excessive by 0-1% (according to a molar ratio, and according to the actual magnesium excessive condition in the reaction).
As a preferred technical scheme of the invention:
the ethylene oxide solution is tetrahydrofuran solution of ethylene oxide, the molar ratio of the ethylene oxide to the chlorobenzene compound is controlled to be 1:1 +/-0.05 in the continuous reaction process of the Grignard reagent and the ethylene oxide solution (the actual operation proportion is adjusted according to the detection result during the operation), and the tetrahydrofuran is directly recovered after the Grignard reaction is finished;
after the tetrahydrofuran is recovered, continuously neutralizing with 10% hydrochloric acid until the pH value is 3-6.
Compared with the prior art, the invention has the following beneficial effects:
(1) the raw material magnesium (preferably magnesium powder) is fed from the top of the column reactor, the chlorobenzene compound solution (preferably tetrahydrofuran solution of chlorobenzene compound) is fed from the bottom of the column reactor, the two raw materials flow in counter-current in the column reactor, and the chlorobenzene compound rises from the bottom to the top to finish the reaction. Short reaction time and high selectivity.
(2) A large number of cooling coils are additionally arranged in the tower reactor, a jacket is arranged on the outer surface of the tower reactor for cooling, a total reflux cooler is arranged at the top of the reaction tower, and a reflux cooler with the cooling area reaching more than 20 times of the volume of the reactor is preferably selected to ensure that the heat generated by the reaction is transferred immediately.
(3) The reaction process is continuously carried out, the adding speed of raw materials is stable, the heat generated by the reaction is stable, and the risk of reaction out of control due to large instant heat release can be avoided.
(4) The partition plate plays a role in relatively separating materials among different areas; the stirring paddle has a mixing function, so that materials in the area can be subjected to a full-mixing kettle reaction effect. The separation plate and the stirring paddle interact with each other, so that the reactor can achieve the effect of multistage kettle type series connection, and the stage number can be designed according to the requirement, thereby theoretically avoiding the influence of back mixing factors.
(5) The invention realizes the continuous synthesis of the phenethyl alcohol.
Drawings
FIG. 1 is a schematic diagram of a system for continuously preparing Grignard reagent synthesized phenethyl alcohol according to the present invention.
In the figure, 1 is a tower reactor, 11 is a partition plate, 12 is a reaction area, 13 is a stirring paddle, 14 is a cooling coil, 15 is a cooling jacket, 16 is a reflux cooler, 2 is a grid reaction kettle, 3 is a falling film scraper evaporator, 4 is an enamel reaction kettle, 5 is a continuous delayer, 6 is an extractor, and 7 is a rectifying tower.
Detailed Description
A method for continuously preparing Grignard reagent to synthesize phenethyl alcohol comprises the steps of continuously preparing Grignard reagent from chlorobenzene compound solution and magnesium; the prepared Grignard reagent and an ethylene oxide solution are continuously reacted to prepare a phenethyl alcohol magnesium salt, and the phenethyl alcohol is obtained by neutralizing, layering, rectifying and other steps of the magnesium salt.
The above method is carried out in a system for continuously preparing a grignard reagent to synthesize the phenethyl alcohol (see fig. 1): continuously preparing the Grignard reagent in a tower reactor 1, preparing the phenethyl alcohol magnesium salt in a Grignard reaction kettle 2, directly recovering the solvent by using a falling film scraper evaporator 3 after the Grignard reaction is finished, neutralizing the magnesium salt in an enamel reaction kettle 4, layering in a continuous layering device 5, extracting the layered water phase in an extractor 6, and rectifying in a rectifying tower 7.
Preferably, the tower reactor is divided into a plurality of reaction zones 12 in the height direction by partition plates 11 (mesh plates may be used), and a plurality of layers of stirring paddles 13 are arranged in each partition zone 12. A cooling coil 14 is arranged in each reaction zone 12 of the tower reactor 1, and a cooling jacket 15 is arranged outside each reaction zone 12 of the tower reactor 1. The top of the tower reactor 1 is provided with a reflux cooler 16. The chlorobenzene compound solution enters the tower reactor 1 from the bottom of the tower, the magnesium enters the tower reactor 1 from the top of the tower, the chlorobenzene compound solution and the magnesium are in countercurrent contact in the tower reactor 1, and the Grignard reaction solution flows out from the top of the tower. Before the grignard reagent is continuously prepared, grignard reagent solution with the volume of 60-90% of that of the tower reactor 1 is prepared as a base material (by a batch method), and enough magnesium for 1-5 hours of reaction is kept in the tower reactor 1 to maintain the excess of magnesium in the continuous reaction process. The chlorobenzene compound solution is tetrahydrofuran solution of 10-30 wt% chlorobenzene compound, the chlorobenzene compound solution and magnesium quantitatively and continuously enter the tower reactor 1, and the ratio of the benzene compound solution to the magnesium is controlled so that the magnesium is excessive by 0-1% (in terms of molar ratio). The continuous preparation of the grignard reagent was carried out under reflux conditions.
Preferably, the lattice reaction kettle 2 is used for continuously flowing the ethylene oxide solution and the lattice reaction liquid flowing out of the tower reactor 1 and reacting under a cooling condition; the falling film scraper evaporator 3 is used for continuously concentrating the reaction liquid flowing out of the lattice type reaction kettle 2 and continuously recovering the solvent; the enamel reaction kettle 4 is used for continuously flowing in a hydrochloric acid solution and a concentrated reaction solution of the lattice reaction kettle, and neutralizing under the conditions of cooling and stirring; the continuous delayer 5 is used for continuously flowing the effluent liquid of the enamel reaction kettle and delaminating the organic phase and the water phase in the effluent liquid of the enamel reaction kettle; the extractor 6 is used for continuously flowing in the water phase and continuously extracting the reaction product in the water phase through continuously flowing in toluene; the rectifying tower 7 is used for continuously flowing in an organic phase and an extract liquor and obtaining a reaction product by rectification. The ethylene oxide solution is tetrahydrofuran solution of ethylene oxide, the molar ratio of the ethylene oxide to the chlorobenzene compound is controlled to be 1:1 +/-0.05 in the continuous reaction process of the Grignard reagent and the ethylene oxide solution, and the tetrahydrofuran is directly recovered after the Grignard reaction is finished; after the tetrahydrofuran is recovered, continuously neutralizing with 10% hydrochloric acid until the pH value is 3-6.
The invention is described in detail below with reference to the figures and specific embodiments.
Example 1
The diameter of the tower reactor 1 is 600mm, the height of the reaction section is 8 meters, and the height of the settling separation section is 1 meter and the diameter is 900 mm; the volume of the reaction section is 2.2 cubic meters, and the volume of the settling section is 0.63 cubic meter. The top of the settling section is provided with a tubular full-reflux condenser with the area of 10 square and a magnesium powder continuous feeder. Each 2 m of the reaction sections are one section (one reaction area), the sections are connected by flanges, a partition plate is arranged, each section is provided with an outer jacket, and a cooling coil is arranged in each section; the stirring space is 500mm, the three-blade paddle type is adopted, the length of the paddle is 200mm, and three layers of stirring paddles are arranged between the partition plates.
The reacted Grignard reagent in an amount of 90% by volume of the column was fed in advance to the column, 280 kg/h (0.5 Kmol/h) of a chlorobenzene tetrahydrofuran solution (20% by mass) was continuously fed from the bottom of the Grignard reaction column, and 12.3 kg/h (0.506 Kmol/h) of magnesium powder was continuously fed from the top of the column. The stirring speed was controlled at 60 rpm, and the reaction was continued under cooling with a jacket and a cooling coil under slight reflux. The Grignard reaction solution flowing out of the tower top was sampled and added with ice diluted hydrochloric acid, and the GC analysis content was 99.5%. The Grignard reaction solution overflowed from the column reactor was introduced into a 500-liter Grignard reaction vessel, and 148 kg/h (0.505 Kmol/h) of a mixed solution of ethylene oxide and tetrahydrofuran (15% by mass) was pumped into the vessel and reacted under cooling.
After the reaction is finished, the reaction liquid flows through a falling film scraper evaporator to continuously recover tetrahydrofuran. And (3) allowing the concentrated reaction solution to flow into a 500-liter enamel reaction kettle with an upper overflow port, cooling, and continuously neutralizing with a 10% hydrochloric acid solution under stirring to reach a pH value of 3-5. The reaction liquid overflowed from the enamel kettle enters a continuous layering device, and an upper organic phase is collected. The water phase is continuously extracted by toluene of 50L/h, and the pure product of the phenethyl alcohol is obtained by merging organic phases and recovering the solvent and then rectifying. The purity of the product reaches more than 99.9 percent, and the quality of the product meets the quality requirement of food-grade additives. 57.5 kg/h of product can be obtained per hour according to time, and the yield reaches 94.2%.
Example 2
560 kg/h (0.5 Kmol/h) of chlorobenzene tetrahydrofuran solution (10% by mass) was continuously fed from the bottom of a 600mm column reactor, and 12.0 kg/h (0.5 Kmol/h) of magnesium powder was continuously fed from the top of the column. The stirring speed was controlled at 60 rpm, and the reaction was continued under cooling with a jacket and a cooling coil under slight reflux. The Grignard reaction solution overflowed from the Grignard reaction column was poured into a 500 liter Grignard reaction vessel (GC analysis content: 98.9%), and 146 kg/h (0.501 Kmol/h) of a mixture of ethylene oxide and tetrahydrofuran (15% by mass) was pumped into the vessel and reacted under cooling.
After the reaction is finished, the reaction liquid flow passes through a falling film scraper evaporator to continuously recover tetrahydrofuran. And (3) allowing the concentrated reaction solution to flow into a 500-liter enamel reaction kettle with an upper overflow port, cooling, and continuously neutralizing with a 10% hydrochloric acid solution under stirring until the pH value is 4-6. The reaction liquid overflowed from the enamel reaction kettle enters a continuous layering device, and an upper organic phase is collected. The water phase is continuously extracted by toluene of 50L/h, and the pure product of the phenethyl alcohol is obtained by merging organic phases and recovering the solvent and then rectifying. The purity of the product reaches more than 99.9 percent, and the quality of the product meets the quality requirement of food-grade additives. 55.5 kg/h of the product can be obtained per hour according to the time, and the yield reaches 91.0 percent.
Example 3
1 kg/h (0.5 Kmol/h) of chlorobenzene tetrahydrofuran solution (30 mass ratio concentration) is continuously injected from the bottom of a 600mm tower reactor, and 12.2 kg/h (0.502 Kmol/h) of magnesium powder is continuously added from the tower top. The stirring speed was controlled at 60 rpm, and the reaction was continued under cooling with a jacket and a cooling coil under slight reflux. The Grignard reaction solution overflowed from the Grignard reaction column was introduced into a 500-liter Grignard reaction vessel, and 154 kg/hr (0.525 Kmol/hr) of a mixed solution of ethylene oxide and tetrahydrofuran (15% by mass) was pumped into the vessel and reacted under cooling.
After the reaction is finished, the reaction liquid flows through a falling film scraper evaporator to continuously recover tetrahydrofuran. The concentrated reaction solution flows into a 500L enamel reaction kettle provided with an upper overflow port, is cooled and is continuously neutralized by 10 percent hydrochloric acid solution under the stirring condition, and the pH value is 4-6. The reaction liquid overflowed from the enamel reaction kettle enters a continuous layering device, and an upper organic phase is collected. The water phase is continuously extracted by toluene of 50 liters/hour, and the organic phase is merged and rectified after the solvent is recovered to obtain the pure phenethyl alcohol. The purity of the product reaches more than 99.9 percent, and the quality of the product meets the quality requirement of food-grade additives. 56.7 kg/h of product can be obtained per hour according to time, and the yield reaches 93.1%.
The embodiments described above are intended to facilitate the understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (6)
1. A system for continuously preparing and synthesizing phenethyl alcohol is characterized by comprising a tower reactor for continuously preparing Grignard reagent by reacting chlorobenzene compound solution with magnesium, wherein the tower reactor is divided into a plurality of reaction areas along the height direction by partition plates, and each divided area is internally provided with a plurality of layers of stirring paddles;
the chlorobenzene compound solution enters a tower reactor from the bottom of the tower, the magnesium enters the tower reactor from the top of the tower, the chlorobenzene compound solution and the magnesium are in countercurrent contact in the tower reactor, and the Grignard reaction solution flows out from the top of the tower;
a cooling coil is arranged in each reaction area of the tower reactor, and a cooling jacket is arranged outside each reaction area of the tower reactor;
a reflux cooler is arranged at the top of the tower reactor;
the system also comprises a lattice reaction kettle, a falling film scraper evaporator, an enamel reaction kettle, a continuous delayer, an extractor and a rectifying tower;
the lattice reaction kettle is used for the continuous inflow of an ethylene oxide solution and a lattice reaction liquid flowing out of the tower reactor and the reaction under the cooling condition,
the falling film scraper evaporator is used for continuously concentrating reaction liquid flowing out of the grignard reaction kettle and continuously recovering a solvent,
the enamel reaction kettle is used for continuous inflow of a hydrochloric acid solution and a concentrated reaction solution of the lattice reaction kettle, and neutralization under the conditions of cooling and stirring,
the continuous delayer is used for continuously flowing the effluent liquid of the enamel reaction kettle and delaminating the organic phase and the water phase in the effluent liquid of the enamel reaction kettle,
the extractor is used for the continuous inflow of the water phase and the continuous extraction of the reaction product in the water phase through the continuous inflow of toluene,
the rectifying tower is used for continuously flowing in an organic phase and an extraction liquid and obtaining a reaction product through rectification.
2. A method for continuously preparing a grignard reagent-synthesized phenethyl alcohol, which comprises the step of continuously preparing the grignard reagent in a column reactor with a chlorobenzene compound solution and magnesium by using the system of claim 1.
3. The method for continuously preparing the Grignard reagent for synthesizing the phenethyl alcohol according to claim 2, further comprising continuously reacting the Grignard reagent with an ethylene oxide solution to prepare the magnesium phenethyl alcohol salt, wherein the magnesium phenethyl alcohol salt is neutralized, layered and rectified to obtain the phenethyl alcohol.
4. The method for continuously preparing the Grignard reagent for synthesizing the phenethyl alcohol according to claim 3, wherein;
before continuously preparing the lattice reagent, preparing a lattice reagent solution with the volume of 60-90% of that of the tower reactor as a bottom material, and keeping enough magnesium for reaction for 1-5 hours in the tower reactor;
the continuous preparation of the grignard reagent was carried out under reflux conditions.
5. The method for continuously preparing the Grignard reagent synthesized phenethyl alcohol according to claim 3, wherein the chlorobenzene compound solution is 10-30 wt% of a tetrahydrofuran solution of a chlorobenzene compound, the chlorobenzene compound solution and magnesium are quantitatively and continuously fed into the tower reactor, and the ratio of the benzene compound solution to the magnesium is controlled so that the magnesium is excessive by 0-1%.
6. The method for continuously preparing the Grignard reagent for synthesizing the phenethyl alcohol according to claim 5, wherein:
the ethylene oxide solution is tetrahydrofuran solution of ethylene oxide, the molar ratio of the ethylene oxide to the chlorobenzene compound is controlled to be 1:1 +/-0.05 in the continuous reaction process of the Grignard reagent and the ethylene oxide solution, and the tetrahydrofuran is directly recovered after the Grignard reaction is finished;
after the tetrahydrofuran is recovered, continuously neutralizing with 10% hydrochloric acid until the pH value is 3-6.
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| CN105080437A (en) * | 2015-09-14 | 2015-11-25 | 浙江华亿工程设计有限公司 | Tower type continuous production device for preparing Grignard reagents |
| CN106588958A (en) * | 2015-10-14 | 2017-04-26 | 上虞新和成生物化工有限公司 | Production system and method for continuously preparing alkynol di-Grignard reagent |
| CN106631686A (en) * | 2016-11-07 | 2017-05-10 | 上海应用技术大学 | Preparation method of beta-phenethyl alcohol |
| CN107814687A (en) * | 2017-11-27 | 2018-03-20 | 湖北朗昕生化药业有限公司 | A kind of synthetic method to chlorophenethylol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105080437A (en) * | 2015-09-14 | 2015-11-25 | 浙江华亿工程设计有限公司 | Tower type continuous production device for preparing Grignard reagents |
| CN106588958A (en) * | 2015-10-14 | 2017-04-26 | 上虞新和成生物化工有限公司 | Production system and method for continuously preparing alkynol di-Grignard reagent |
| CN106631686A (en) * | 2016-11-07 | 2017-05-10 | 上海应用技术大学 | Preparation method of beta-phenethyl alcohol |
| CN107814687A (en) * | 2017-11-27 | 2018-03-20 | 湖北朗昕生化药业有限公司 | A kind of synthetic method to chlorophenethylol |
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