CN111018810B - Device and method for continuously producing alpha-acetyl-gamma-butyrolactone - Google Patents
Device and method for continuously producing alpha-acetyl-gamma-butyrolactone Download PDFInfo
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- CN111018810B CN111018810B CN201911289323.6A CN201911289323A CN111018810B CN 111018810 B CN111018810 B CN 111018810B CN 201911289323 A CN201911289323 A CN 201911289323A CN 111018810 B CN111018810 B CN 111018810B
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
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Abstract
The invention relates to a method for continuously producing alpha-acetyl-gamma-butyrolactone, which comprises the following steps: continuously adding gamma-butyrolactone, acetic ester and liquid metal sodium into a condensation reactor for condensation reaction, continuously transferring the condensation reaction liquid into a neutralization reactor after the condensation reaction is finished, cooling, and adding phosphoric acid for neutralization; transferring the neutralized solution into a phase separator by a pump, standing for phase separation, removing a water phase, transferring an oil phase into a distillation system, and distilling under normal pressure and reduced pressure to obtain the alpha-acetyl-gamma-butyrolactone. The continuous production method is adopted, so that the sealing and automation are realized, benzene substances are not required to be added as reaction solvents or extracting agents, the reaction yield is improved, and the product quality is more stable.
Description
Technical Field
The invention relates to a production method of a medical intermediate, a pesticide intermediate and a chemical raw material, relates to a device and a method for continuously producing alpha-acetyl-gamma-butyrolactone, in particular to a continuous production method of alpha-acetyl-gamma-butyrolactone, and belongs to the technical field of chemical production and preparation.
Background
The alpha-acetyl-gamma-butyrolactone is an important drug intermediate and an organic chemical raw material, is an important intermediate for preparing vitamins and chlorophyll, and is also a medical intermediate for synthesizing antipsychotic drugs risperidone, anticonvulsants, sedative hypnotics, chloromethylthiazole, Yanxintong, chloroquine and other drugs. The current methods for preparing α -acetyl- γ -butyrolactone mainly have two routes, one is a process using ethylene oxide and ethyl acetoacetate as starting materials, and the other is a process using γ -butyrolactone and acetic acid acetate as starting materials.
Among them, Chinese patent application documents (publication No. CN 1357545A), U.S. Pat. No. US 2443827, British patent GB 740993 and Japanese patent JP 4212662, etc. disclose similar processes for the synthesis of α -acetyl- γ -butyrolactone starting from ethylene oxide and ethyl acetoacetate. However, the yield of the process route is only about 70% at most, the cost is high, the ethylene oxide serving as a reaction raw material belongs to a first-class flammable and explosive chemical, and serious potential safety hazards exist in the processes of storage, transportation and reaction.
For example, Chinese patent application documents (publication No. CN 101230054A) and (publication No. CN 1548427A) disclose that gamma-butyrolactone and acetate are used as starting materials, benzene compounds are used as a reaction solvent, sodium metal or sodium alkoxide is used as a reaction catalyst, the raw materials and the catalyst are subjected to batch reaction in a reaction kettle, after the reaction is finished, acid is used for neutralization, an extracting agent is used for extraction, and an extract is rectified to obtain a final product. However, the process has the problems of over violent reaction, slow heat dissipation of a reaction kettle, difficult temperature control and the like, and accidents such as material flushing, combustion and the like are easy to occur in the production process, and a large amount of benzene solvents and waste acid generated by acidification in the production process can cause serious pollution to the environment.
As another example, Chinese patent application (publication No. CN 102030729A) discloses a method for synthesizing alpha-acetyl-gamma-butyrolactone without using benzene as a reaction solvent, wherein metallic sodium is added into the system at one time, and the acylation reaction rate is controlled by controlling the specific surface area of the metallic sodium. However, metallic sodium is liable to be agglomerated after being charged at one time, and the operation is difficult, and the reaction time required increases.
While the Chinese patent application (publication No. CN 101768141A) adopts a method of adding a metallic sodium catalyst into a reaction system by times or continuously, which can effectively avoid potential safety hazards such as material flushing, combustion and the like caused by difficulty in controlling the reaction speed, toluene is used as an extracting agent, so that the toxicity is high, the separation is difficult, and the product quality is influenced by the residue of the toluene.
Chinese patent application document (publication number: CN 102229586A) reports that the contact area of a metallic sodium catalyst and reaction raw materials can be effectively increased by preparing metallic sodium into sodium sand, so that the catalytic efficiency of the metallic sodium is improved. However, molten metal sodium is rapidly cooled to 50-60 ℃ and is easy to agglomerate, so that the method is difficult to implement in industrial production, and meanwhile, a chlorine-containing solvent is used, so that the method has great pollution to the environment.
In addition, Chinese patent application (publication No. CN 101092407A) discloses that alpha-acetyl-gamma-butyrolactone is synthesized by carrying out an acylation reaction on ethyl acetate and gamma-butyrolactone through gas-phase catalysis of a fluorine-alkali solid-phase catalyst, although the potential safety hazard is solved, the cost is overhigh due to higher energy consumption, and certain potential hazard exists on product and environment pollution by adopting solid alkali fluoride as the catalyst, and the solid alkali fluoride is not put into practical production and life at present.
Disclosure of Invention
The invention provides a device and a method for continuously producing alpha-acetyl-gamma-butyrolactone, aiming at solving the problems of low safety, poor reaction stability, large product quality fluctuation, low production efficiency and the like in the prior intermittent technology.
In order to solve the technical problem, the invention is solved by the following technical scheme: an apparatus for continuously producing alpha-acetyl-gamma-butyrolactone, comprising:
the condensation reactor is used for carrying out condensation reaction on materials;
a neutralization reactor for adjusting the pH value and converting the sodium salt obtained by condensation into alpha-acetyl-gamma-butyrolactone;
the phase separator is used for standing and separating an organic phase and a water phase;
an atmospheric distillation system for continuous distillation to remove light components from the organic phase;
a vacuum rectification system for continuous rectification,
the condensation reactor, the neutralization reactor, the phase separator, the atmospheric distillation system and the vacuum distillation system are communicated in sequence.
In the above apparatus for continuously producing α -acetyl- γ -butyrolactone, the condensation reactor comprises a microchannel reactor, a tank reactor, a loop reactor, and a series connection of the tank reactor and the tubular reactor.
In the above continuous production apparatus for α -acetyl- γ -butyrolactone, a power pump for providing kinetic energy for circulation is further provided between the neutralization reactor and the phase separator.
The invention also provides a method for continuously producing the alpha-acetyl-gamma-butyrolactone, which comprises the following steps:
(1) simultaneously and continuously adding gamma-butyrolactone, acetate and liquid metal sodium into a condensation reactor for condensation reaction;
(2) after the condensation reaction is finished, continuously transferring the condensation reaction liquid into a neutralization reactor, cooling, and adding phosphoric acid for neutralization;
(3) transferring the neutralized solution into a phase separator by a pump, standing for phase separation, removing a water phase, transferring an oil phase into a distillation system, and distilling under normal pressure and reduced pressure to obtain the alpha-acetyl-gamma-butyrolactone.
The invention adopts gamma-butyrolactone, acetic ester and liquid metal sodium to continuously enter a condensation reactor for continuous condensation reaction, continuously discharges reaction liquid to enter a neutralization reactor, and then continuously neutralizes by phosphoric acid, phase-splits, distills under normal pressure and rectifies under reduced pressure to obtain the product. The reaction process is controlled by adjusting the flow of gamma-butyrolactone, acetic ester and liquid metal sodium, a continuous production method and a production system are adopted, so that the reaction process is more stable and safer, the reaction control adopts automatic control, the serious potential safety hazards that the traditional intermittent production reaction is too violent, the material is easy to flush and the like are avoided, meanwhile, the continuous production method is adopted, the sealing and the automation are easier to realize, and the reaction yield and the product quality are more stable. In addition, in the prior art, the metal sodium is basically directly added when the alpha-acetyl-gamma-butyrolactone is prepared, the liquid metal sodium in a molten state is added into a system, the rate of the condensation reaction is controlled by controlling the liquid metal sodium in the molten state, and at the rate, the instability of the condensation reaction caused by the aggregation of one-time addition of the metal sodium can be prevented, the potential safety hazards of over-violent condensation reaction and easiness in material flushing in the traditional method are avoided, and the time of the condensation reaction is reduced.
In the method for continuously producing the alpha-acetyl-gamma-butyrolactone, the molar mass ratio of the gamma-butyrolactone to the acetate is 1: 1.5-5.0. Preferably, the molar mass ratio of the gamma-butyrolactone to the acetate is 1: 2.0-4.0.
Preferably, the acetate is one or more of methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate and sec-butyl acetate.
In the above method for continuously producing α -acetyl- γ -butyrolactone, the molar mass ratio of γ -butyrolactone to liquid metal sodium is 1: 0.8-1.5. Preferably, the molar mass ratio of the gamma-butyrolactone to the liquid metal sodium is 1: 1.0-1.3.
In the method for continuously producing the alpha-acetyl-gamma-butyrolactone, the condensation reaction temperature is 60-100 ℃. Preferably, the condensation reaction is carried out at a temperature of 75 to 90 ℃.
In the above-mentioned method for continuously producing α -acetyl- γ -butyrolactone, the residence time of the condensation reaction is 1 to 16 hours. Preferably, the residence time of the condensation reaction is 8 to 10 hours. The retention time after the condensation reaction is the reflux of the system, and the yield of the finally obtained alpha-acetyl-gamma-butyrolactone is maximized.
In the method for continuously producing the alpha-acetyl-gamma-butyrolactone, the pressure of the condensation reaction is 0-2.0 MPa. Preferably, the pressure of the reaction is 0 to 0.5 MPa.
In the method for continuously producing the alpha-acetyl-gamma-butyrolactone, the temperature of the neutralization reaction is 40-60 ℃, the mass concentration of phosphoric acid used in the neutralization reaction is 40-60%, and the molar ratio of the phosphoric acid used in the neutralization reaction to the gamma-butyrolactone is 0.4-1.2: 1. Preferably, the molar ratio of the phosphoric acid to the gamma-butyrolactone is 0.7-0.9: 1.
In the method for continuously producing the alpha-acetyl-gamma-butyrolactone, the temperature of the reduced pressure rectification is 120-150 ℃, and the absolute pressure is 1-50 kPa. Preferably, the temperature of the vacuum distillation is 130 ℃, and the absolute pressure of the vacuum distillation is 5-10 kPa.
Due to the adoption of the technical scheme, the invention has the remarkable technical effects that:
(1) the invention controls the reaction process by adjusting the flow of gamma-butyrolactone, acetic ester and liquid metal sodium, adopts a continuous production method, makes the reaction process more stable and safer, adopts automatic control for reaction control, avoids serious potential safety hazards such as over violent reaction, easy material flushing and the like of the traditional intermittent production, and simultaneously adopts the continuous production method, thereby being easier to realize sealing and automation, and having more stable reaction yield and product quality.
(2) The method does not need to adopt benzene substances as a reaction solvent or an extracting agent to extract the water phase, has relatively simple operation, eliminates a pollution source from the source, is green and environment-friendly, greatly reduces the production cost, improves the comprehensive economic benefit, and avoids the problems of environmental pollution, difficult separation and the like caused by the use of benzene substances as solvents in the traditional process.
(3) The method adds the metal sodium in the molten state, can better control the dripping speed, further better control the rate of condensation reaction, prevent the instability of the condensation reaction caused by the aggregation of one-time addition of the metal sodium, avoid the potential safety hazard that the condensation reaction is too violent and the material is easy to wash in the traditional batch method, simultaneously reduce the time of the condensation reaction, complete the condensation reaction along with the dripping completion of the liquid metal sodium in the molten state, accelerate the progress of the condensation reaction, and facilitate the maximization of the yield of the alpha-acetyl-gamma-butyrolactone through the subsequent heat preservation.
Detailed Description
The present invention will be described in further detail with reference to examples.
As shown in fig. 1, the production system for continuously producing α -acetyl- γ -butyrolactone according to the present invention comprises:
the condensation reactor is used for carrying out condensation reaction on materials;
a neutralization reactor for adjusting the pH value and converting the sodium salt obtained by condensation into alpha-acetyl-gamma-butyrolactone;
the phase separator is used for standing and separating an organic phase and a water phase;
an atmospheric distillation system for continuous distillation to remove light components from the organic phase;
a vacuum rectification system for continuous rectification,
the condensation reactor, the neutralization reactor, the phase separator, the atmospheric distillation system and the vacuum distillation system are communicated in sequence.
Further, the condensation reactor comprises a microchannel reactor, a kettle reactor, a loop reactor and a series connection of the kettle reactor and a tubular reactor.
Further, a power pump for providing circulation kinetic energy is arranged between the neutralization reactor and the phase separator.
Examples 1 to 29
Gamma-butyrolactone, ethyl acetate and liquid sodium metal are continuously added into a tubular reactor according to the molar ratios respectively described in examples 1-29 of table 1 to simultaneously carry out condensation reaction as described in examples 1-29, hydrogen is continuously generated during the reaction process, the generated alpha-acetyl-gamma-butyrolactone sodium salt solution continuously enters a neutralization reactor through a pipeline, neutralization reaction is continuously carried out with the prepared phosphoric acid aqueous solution with the content of 50%, the molar ratio of the phosphoric acid to the gamma-butyrolactone is 0.8:1, the reacted materials continuously enter a phase separator through a pipeline from the outlet of the neutralization reactor to carry out phase separation, an organic phase and a water phase are separated, the organic phase from the phase separator is continuously distilled by an atmospheric distillation tower to remove light components, the tower bottom materials are continuously pumped into a reduced pressure distillation tower to carry out continuous rectification by a pump, to obtain the alpha-acetyl-gamma-butyrolactone product.
Example 30: this embodiment is the same as embodiment 4 except that: the reactor in the condensation reaction process adopts a micro-channel reactor.
Example 31: this embodiment is the same as embodiment 1 except that: the reactor in the condensation reaction process adopts a kettle type reactor.
Example 32: this embodiment is the same as embodiment 1 except that: the reactor in the condensation reaction process adopts a loop reactor.
Example 33: this embodiment is the same as embodiment 1 except that: in the condensation reaction process, the reactor adopts a kettle type reactor and a tubular reactor which are connected in series.
TABLE 1 raw materials, parameters and results in examples 1-33
In conclusion, the method for producing the alpha-acetyl-gamma-butyrolactone by the invention controls the reaction process by adjusting the flow rates of the gamma-butyrolactone, the acetic ester and the liquid metal sodium, adopts a continuous production method, realizes the sealing and automation, does not need to add benzene substances as a reaction solvent or an extractant, improves the reaction yield and ensures that the product quality is more stable.
The specific embodiments described herein are merely illustrative of the spirit of the invention and do not limit the scope of the invention. Various modifications or additions may be made to the described embodiments or alternatives may be employed by those skilled in the art without departing from the spirit or ambit of the invention as defined in the appended claims.
Claims (2)
1. A method for continuously producing alpha-acetyl-gamma-butyrolactone, which is characterized by comprising the following steps:
(1) simultaneously and continuously adding gamma-butyrolactone, ethyl acetate and liquid metal sodium into a condensation reactor for condensation reaction;
(2) after the condensation reaction is finished, continuously transferring the condensation reaction liquid into a neutralization reactor, cooling, and adding phosphoric acid for neutralization;
(3) transferring the neutralized solution into a phase separator by a pump, standing for phase separation, removing a water phase, transferring an oil phase into a distillation system, and distilling under normal pressure and reduced pressure for rectification to obtain alpha-acetyl-gamma-butyrolactone;
the molar mass ratio of the gamma-butyrolactone, the liquid metal sodium and the ethyl acetate is 1:1.2: 3.0;
the condensation reaction temperature is 85 ℃, the residence time of the condensation reaction is 10 hours, and the pressure of the condensation reaction is 0.5 MPa;
the method utilizes a device for continuously producing alpha-acetyl-gamma-butyrolactone, wherein the device comprises a condensation reactor for carrying out condensation reaction on materials;
a neutralization reactor for adjusting the pH value and converting the sodium salt obtained by condensation into alpha-acetyl-gamma-butyrolactone;
the phase separator is used for standing and separating an organic phase and a water phase;
an atmospheric distillation system for continuous distillation to remove light components from the organic phase;
a vacuum rectification system for continuous rectification,
the condensation reactor, the neutralization reactor, the phase separator, the atmospheric distillation system and the vacuum distillation system are communicated in sequence;
the condensation reactor is a loop reactor.
2. The method for continuously producing α -acetyl- γ -butyrolactone according to claim 1, wherein a power pump for supplying kinetic energy for circulation is further provided between the neutralization reactor and the phase separator.
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