CN112661633A - Method for continuously preparing antioxidant 1010 - Google Patents
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Abstract
本发明公开了一种连续制备抗氧剂1010的方法，所述方法包括：首先在配料釜中把固相反应物季戊四醇溶解在另一种液相反应物β‑（3,5‑二叔丁基‑4‑羟基苯基）丙酸甲酯中，然后依次通过一级反应釜、二级反应釜和保护反应釜，三个反应釜在相同压力下温度逐渐升高并最终在保护反应釜内完成全部反应，反应结束后的出产品可采用常规洗涤、结晶和干燥等过程获得最终产品。本发明制备方法采用多级串联搅拌釜式连续反应装置，可以灵活反应操作条件，有效克服了目前间歇生产装置操作周期长、反应不完全、副产物含量多且劳动强度大的缺点，提高了产品收率。
The invention discloses a method for continuously preparing antioxidant 1010. The method comprises: first dissolving solid-phase reactant pentaerythritol in another liquid-phase reactant β-(3,5-di-tert-butylene) in a batching kettle (base-4-hydroxyphenyl) methyl propionate, then successively pass through the primary reactor, the secondary reactor and the protection reactor, and the temperature of the three reactors gradually increases under the same pressure and finally in the protection reactor After completing the whole reaction, the product after the reaction can be obtained by conventional washing, crystallization and drying processes to obtain the final product. The preparation method of the invention adopts a multi-stage series-connected stirred tank type continuous reaction device, which can flexibly react the operating conditions, effectively overcomes the shortcomings of the current batch production device such as long operation period, incomplete reaction, high content of by-products and high labor intensity, and improves the product quality. yield.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing antioxidant 1010 by adopting a continuous stirred tank type reaction and completing the reaction through multistage series connection.
Background
The chemical name of the antioxidant 1010 is: the final product of the tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester is white crystalline powder, has stable chemical properties, and can be widely applied to the industries of general plastics, engineering plastics, synthetic rubber, fiber, hot melt adhesive, resin, oil products, ink, paint and the like. At present, the preparation process is intermittent operation, and the beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate (hereinafter referred to as 3,5 methyl ester) and pentaerythritol are subjected to ester exchange reaction under the action of a catalyst to generate the beta-methyl propionate.
The transesterification reaction for generating the antioxidant 1010 needs to be carried out under the action of a catalyst, common catalysts comprise sodium methoxide, potassium tert-butoxide and dibutyltin oxide, and a byproduct methanol can be generated when 3,5 methyl ester reacts with pentaerythritol to generate the antioxidant 1010. In the ester exchange reaction process, the theoretical molar ratio of the pentaerythritol to the 3,5 methyl ester is 1:4, because the pentaerythritol has four symmetrical hydroxyl groups, in the reaction process, the four hydroxyl groups of the pentaerythritol react in sequence, and only the four hydroxyl groups need to be subjected to ester exchange with the 3,5 methyl ester to generate the final target product. After the reaction of three hydroxyl groups of pentaerythritol is completed, the transesterification reaction of the last hydroxyl group of the intermediate product 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid group formed is limited due to the large three-dimensional structure, so that the reaction residence time must be increased to ensure that the reaction is complete as much as possible, and the period of the batch operation process is longer.
In the existing method for preparing the antioxidant 1010, a batch kettle method is adopted to prepare the antioxidant. For example, in patent CN 102485833A: in an atmospheric reaction kettle, 3,5 methyl ester, pentaerythritol and a catalyst are mixed according to the weight ratio of 600: 70: 5, reacting for 7-9 hours under a vacuum condition, and crystallizing, throwing materials and drying reactants to obtain a finished product. In patent CN 102329232A: the invention discloses a synthetic method of an antioxidant, which comprises the steps of sequentially adding 3,5 methyl ester, pentaerythritol, a catalyst and magnesium silicate into a reaction kettle, charging nitrogen into the kettle, heating after 0.5 hour, starting stirring after the materials are completely melted, controlling the reaction temperature to be 155-200 ℃, keeping the nitrogen flow rate in the reaction process so as to take out the generated methanol to enter a condenser, condensing and recycling, stopping the reaction after reacting for one hour to obtain a crude product of the antioxidant, washing, crystallizing and drying to obtain the antioxidant. In patent CN 109896952 a: the invention provides a synthetic method of an antioxidant 1010, comprising the steps of feeding a kettle, filling nitrogen, heating after 0.5 hour, starting stirring after the materials are completely melted, controlling the reaction temperature, keeping the nitrogen flow rate in the reaction process to take generated methanol out to enter a condenser, condensing and recovering, stopping the reaction after 10 hours of reaction to obtain a crude product of the antioxidant 1010, washing and crystallizing, and drying to obtain the antioxidant 1010.
Therefore, at present, the production of the antioxidant adopts an intermittent kettle method, firstly reaction materials of pentaerythritol, 3,5 methyl ester and a catalyst are put into a reaction kettle, then the reaction kettle is heated and stirred to dissolve the pentaerythritol, then the reaction is carried out by vacuumizing without further heating, and the generated methanol enters a condenser for condensation and recovery under the reaction condition because the reaction is carried out intermittently, wherein the mode of firstly cooling and then heating leads to energy waste and production efficiency reduction.
Even so, it was found in both practical production and literature studies that a part of the triester could not further react with 3,5 methyl ester to 1010 but existed as a by-product in the reaction liquid. Therefore, the existing intermittent production device has the defects of long operation period, incomplete reaction, high byproduct content and high labor intensity.
Disclosure of Invention
The invention provides a method for continuously preparing an antioxidant 1010, which is used for solving the technical problems that the conventional antioxidant production adopts an intermittent kettle method, energy waste and production efficiency reduction are caused by a mode of firstly cooling and then heating, and the intermittent production device has the defects of long operation period, incomplete reaction, high byproduct content and high labor intensity.
Aiming at the above problems of the batch reaction, analysis finds that the ester exchange reaction of hydroxyl and 3,5 methyl ester is a balanced reaction, and the increase of the concentration of reactants and the reduction of the concentration of products are both beneficial to the reaction towards the direction of target products, so that the molar ratio of 3,5 methyl ester is generally improved in the production process, and the by-product methanol is taken away by adopting a vacuum and high-temperature method in the reaction process, thereby promoting the reaction to be carried out towards the positive direction. Therefore, the present invention provides a method for continuously preparing antioxidant 1010 based on the above theoretical analysis, comprising the following steps:
a material preparation step, namely adding granular pentaerythritol into a material preparation kettle, and filling nitrogen for protection; adding beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate (hereinafter referred to as 3,5 methyl ester), heating and stirring to fully dissolve the pentaerythritol and mix the pentaerythritol with the beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate to obtain a reaction solution;
continuously preparing an antioxidant, namely feeding the reaction liquid in the batching kettle into a first-stage reaction kettle by using a feeding pump, adding a catalyst, feeding the reaction liquid in the first-stage reaction kettle into a second-stage reaction kettle, feeding the reaction liquid in the second-stage reaction kettle into a protective reaction kettle, and generating a crude product with the antioxidant 1010 in the protective reaction kettle;
and purifying the antioxidant, namely purifying the crude product in the protection reaction kettle to obtain the antioxidant 1010.
Further, the mass ratio of 3,5 methyl ester to pentaerythritol put into the batching kettle is (8.6-15) to 1; the temperature of the batching kettle is between 80 and 150 ℃, and the pressure is between 0.01 and 0.2 MPa.
Further, the temperature of the primary reaction kettle is controlled between 150 ℃ and 200 ℃; the pressure is between 0.0005 and 0.005 MPa; the retention time of the reaction liquid in the first-stage reaction kettle and the second-stage reaction kettle is between 0.5 and 2.0 hours.
Further, the temperature of the secondary reaction kettle is controlled between 170 ℃ and 210 ℃; the pressure is between 0.0005 and 0.005 MPa; the residence time of the reaction liquid in the secondary reaction kettle is between 0.5 and 2.0 hours.
Further, the temperature of the protective reaction kettle is between 170 ℃ and 210 ℃; the pressure is between 0.0005 and 0.005 MPa; the residence time of the reaction liquid in the reaction kettle is between 0.5 and 2.0 hours.
Further, in the step of purifying the antioxidant, the crude product in the protective reaction kettle is purified through washing, crystallization and drying to obtain the antioxidant 1010.
Further, before the step of dosing, the method further comprises:
a production line is set, and the batching kettle, the feeding pump, the primary reaction kettle, the secondary reaction kettle and the protective reaction kettle are sequentially connected to form a production line for continuously preparing the antioxidant 1010; the batching kettle, the first-stage reaction kettle, the second-stage reaction kettle and the protective reaction kettle are all provided with a jacket heating device and a stirring device, and gas-phase discharge holes of the first-stage reaction kettle, the second-stage reaction kettle or the protective reaction kettle are communicated with a condensing device.
Further, in the step of setting the production line, the jacket heating device is heated by steam or heat conducting oil, and the condensing device is cooled by warm water.
Further, in the step of arranging the production line, the condensing device is provided with at least one stage of condenser; wherein the condenser is communicated with a vacuum system and is used for condensing and recovering the intermediate product; and a return pipe is also arranged between the condenser directly connected with the first-stage reaction kettle and the second-stage reaction kettle and the first-stage reaction kettle and the second-stage reaction kettle.
Further, in the step of setting the production line, the temperature of the condenser is between 60 and 120 ℃.
The invention has the beneficial effects that the method for continuously preparing the antioxidant 1010 is provided, and comprises the following steps: firstly, a solid-phase reactant pentaerythritol is dissolved in another liquid-phase reactant methyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate in a batching kettle, and then the solid-phase reactant pentaerythritol is sequentially passed through a first-stage reaction kettle, a second-stage reaction kettle and a protective reaction kettle, wherein the three reaction kettles are gradually heated under the same pressure, and finally the whole reaction is completed in the protective reaction kettle. The three reaction kettles control the reaction temperature through steam or heat conducting oil, and control the retention time through liquid level adjustment or discharging the height of each U-shaped bend. The final product can be obtained by the processes of conventional washing, crystallization, drying and the like of the product after the reaction is finished. By adopting the multistage serial stirred tank type continuous reaction device, the invention can flexibly react and operate conditions, effectively overcomes the defects of energy waste, low production efficiency, long operation period, incomplete reaction, high byproduct content and high labor intensity in the conventional intermittent production method, and improves the product yield.
Drawings
The technical solution and other advantages of the present application will become apparent from the detailed description of the embodiments of the present application with reference to the accompanying drawings.
FIG. 1 is a flow chart of a process for the continuous preparation of antioxidant 1010 according to the present invention;
FIG. 2 is a schematic view of the structure of the production line in the step of setting the production line according to the present invention.
The drawings are identified below:
the preparation method comprises the steps of mixing a material mixing kettle 1,
a feeding pump (2) is arranged on the feeding device,
a first-stage reaction kettle 3 is arranged,
a second-stage reaction kettle 4 is arranged,
the reaction kettle 5 is protected, and the reaction kettle is protected,
the condensation device (6) is arranged in the air-conditioning system,
the vacuum system (7) is provided with a vacuum system,
the stirring device (8) is arranged on the inner wall of the container,
in the production line 10, the production line is,
a first-stage condenser (61) for condensing the refrigerant,
a secondary condenser 62.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application. It is to be understood that the embodiments described are only a few embodiments of the present application and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
In the embodiment of the invention, aiming at the problems of energy waste, low production efficiency, long operation period, incomplete reaction, high byproduct content and high labor intensity caused by the production method of the intermittent reaction, analysis shows that the transesterification reaction of hydroxyl and 3,5 methyl ester is a balanced reaction, the increase of the concentration of reactants and the reduction of the concentration of products are both beneficial to the reaction towards the direction of a target product, so that the molar ratio of 3,5 methyl ester is generally improved in the production process, and the byproduct methanol is taken away by adopting a vacuum and high-temperature method in the reaction process, thereby promoting the reaction to be carried out towards the positive direction. Therefore, as shown in fig. 1 and fig. 2, the present invention proposes a method for continuously preparing antioxidant 1010 based on the above theoretical analysis, and the specific content includes steps S1-S4.
S1, a production line step is set, wherein a batching kettle 1, a feeding pump 2, a primary reaction kettle 3, a secondary reaction kettle 4 and a protective reaction kettle 5 are sequentially connected to form a production line 10 for continuously preparing the antioxidant 1010; wherein, batching kettle 1, first order reation kettle 3, second order reation kettle 4 and protection reation kettle 5 all have jacket heating device (not shown) and agitating unit 8, and the gaseous phase discharge gate intercommunication condensing equipment 6 of first order reation kettle 3, second order reation kettle 4 or protection reation kettle 5. Wherein, the jacket heating device adopts steam or heat conducting oil for heating, and the condensing device 6 adopts warm water for cooling. Wherein, the condensing device 6 is provided with at least one stage of condenser; wherein the condenser is communicated with a vacuum system and is used for condensing and recovering an intermediate product; a return pipe is also arranged between the condenser directly connected with the first-stage reaction kettle 3 and the second-stage reaction kettle 4 and the first-stage reaction kettle 3 and the second-stage reaction kettle 4. Wherein the temperature of the condenser is between 60 and 120 ℃.
In this embodiment, the condensing device 6 is provided with a first-stage condenser 61 and a second-stage condenser 62, and the first-stage condenser 61 is communicated with the second-stage condenser 62 and both communicated with the vacuum system 7. Wherein the first-stage condenser 61 is provided with a return pipe which is communicated with the first-stage reaction kettle 3 and the second-stage reaction kettle 4 and is used for recovering the cooling liquid. The liquid outlet of the secondary condenser 62 is used for recovering intermediate products such as methanol and the like.
S2, a material mixing step, namely adding granular pentaerythritol into a material mixing kettle 1, and filling nitrogen for protection; then adding beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate (hereinafter referred to as 3,5 methyl ester), heating and stirring to fully dissolve pentaerythritol and mixing with the beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) methyl propionate to obtain a reaction solution. More specifically, firstly, granular pentaerythritol is added into a batching kettle 1 and nitrogen is filled for protection. 3,5 methyl ester with a specified weight ratio is added by a pump and is pumped into a proportioning kettle, and the weight ratio of 1, 3,5 methyl ester to pentaerythritol is (8.6-15) to 1, preferably 9-12: 1. After 3,5 methyl esters are put in, the temperature is raised by using jacket steam or heat conducting oil, stirring is started, the temperature of the batching kettle 1 is between 80 and 150 ℃, preferably between 120 and 140 ℃, the pressure is between 0.01 and 0.2MPa, and preferably the normal pressure is selected. The pentaerythritol is completely dissolved in the batching kettle 1 as much as possible, the gas phase generated in the dissolving process is condensed by a condenser 61, the condensate returns to the batching kettle 1, and the non-condensable gas is continuously sent to a secondary condenser 62 for condensation.
S3, continuously preparing an antioxidant, namely, conveying the reaction liquid in the batching kettle 1 into a first-stage reaction kettle 3 by using a feed pump 2, simultaneously adding a catalyst, conveying the reaction liquid in the first-stage reaction kettle 3 into a second-stage reaction kettle 4, conveying the reaction liquid in the second-stage reaction kettle 4 into a protection reaction kettle 5, and generating a crude product with the antioxidant 1010 in the protection reaction kettle 5.
More specifically, the dissolved reaction solution is fed into a first-stage reaction kettle 3 by a feed pump 2, and simultaneously, a catalyst is added. The catalyst is organic tin catalyst, and the dosage of the organic tin catalyst is 0.4-0.8% of the weight of 3,5 methyl ester. The catalyst can be dissolved in the batching kettle 1 in advance, can also be dissolved by utilizing methanol and then sent into the first-stage reaction kettle 3, or is mixed with reaction materials before entering the reaction kettle through a pipeline mixer. The temperature of the first-stage reaction kettle 3 is controlled between 150 ℃ and 200 ℃, preferably between 160 ℃ and 180 ℃; the pressure is between 0.0005 and 0.005MPa, preferably between 0.0008 and 0.002; the liquid phase residence time of the reaction kettle is between 0.5 and 2.0 hours, preferably between 0.8 and 1.2 hours. The first-stage reaction kettle 3 finishes most reactions, by-product methanol generated by the reactions is sent to a condenser 61 for condensation by a vapor phase pipe, reactants carried in methanol vapor are condensed by the first-stage condenser 61, the temperature of the first-stage condenser 61 is between 60 and 120 ℃, preferably between 80 and 100 ℃, methanol which cannot be condensed is sent to a second-stage condenser 62 for continuous condensation, the second-stage condenser 62 uses circulating water for condensation to condense vapor phase materials to about 40 ℃, the condensed methanol is recovered, and noncondensable gas is sent to a vacuum device.
The feed liquid of the first-stage reaction kettle 3 is fed into the second-stage reaction kettle 4 through gravity flow or a pump. The temperature of the secondary reaction kettle 4 is between 170 ℃ and 210 ℃, preferably between 190 ℃ and 210 ℃; the pressure is the same as the pressure of the first-stage reaction kettle 3; the liquid phase retention time of the reaction kettle is between 0.5 and 2.0 hours; preferably between 0.5 and 1.0 hour. The same reaction kettle 3 is the same, and is also provided with a first-stage condenser 61 and a second-stage condenser 62 to recover reaction materials and a byproduct methanol, and the operation method is the same as that of the first-stage reaction kettle 3.
The materials are basically completely reacted in the second-stage reaction kettle 4, and a protective reaction kettle 5 is additionally arranged behind the second-stage reaction kettle 4 to avoid the occurrence of complete reaction in a small amount of accidental situations. The material in the second-stage reaction kettle 4 is fed into the protective reaction kettle 5 through gravity flow or a pump. The temperature of the protective reaction kettle 5 is between 170 ℃ and 210 ℃, preferably between 190 ℃ and 210 ℃; the pressure is the same as the pressure of the first-stage reaction kettle 4 and the second-stage reaction kettle 4; the liquid phase retention time of the reaction kettle is between 0.5 and 2.0 hours; preferably between 0.5 and 1.0 hour. The protective reaction kettle 5 is also provided with a first-stage condenser 61 and a second-stage condenser 62 to recover reaction materials and by-product methanol generated by a small amount of reaction in the protective reaction kettle 5, and the operation method is the same as that of the first-stage reaction kettle 3. Meanwhile, the reaction kettle 5 can be protected and can be used as a reaction material heat exchange tank.
The jackets of the batching kettle, the first-stage reaction kettle 3, the second-stage reaction kettle 4 and the protective reaction kettle 5 can be heated by heating media such as steam, heat conducting oil and the like, the first-stage condenser 61 can be cooled by warm water, and the second-stage condenser 62 is cooled by circulating water.
S4, purifying the antioxidant, namely purifying the crude product in the protective reaction kettle 5 to obtain the antioxidant 1010. In particular, the crude product in the protective reaction kettle 5 can be subjected to conventional washing, crystallization, drying and other processes to obtain the product antioxidant 1010.
The specific embodiments of the present application are as follows:
20kg of pentaerythritol is put into a batching kettle, 220kg of 3,5 methyl ester is added after nitrogen sealing, steam in a jacket of the batching kettle is opened to start heating, and the batching kettle is opened to stir. After half an hour, the temperature is raised to 100 ℃, and the batching is finished after the temperature is kept at 100 ℃ for half an hour. The warm water of the first-stage condenser 61 and the circulating water of the second-stage condenser 62 of the first-stage reaction kettle 3, the second-stage reaction kettle 4 and the protective reaction kettle 5 are started, and the vacuum is started to control the pressure of the reaction system to be 1 kPa. Feeding to the first-stage reaction kettle 3, making the materials flow into the second-stage reaction kettle 4 by using potential difference gravity after reaching a certain liquid level, and feeding the second-stage reaction kettle 4 into the protective reaction kettle 5 by using gravity. The liquid levels of the first-stage reaction kettle 3 and the second-stage reaction kettle 4 are controlled by a U-shaped bend of the discharge pipe. Controlling the temperature of the first-stage reaction kettle 3 to be 185 ℃ and the retention time to be 1.5 h; the temperature of the secondary reaction kettle 4 is 200 ℃, and the retention time is 1.0 h; the temperature of the protective reaction kettle 5 is 200 ℃, and the retention time is 0.5 h. The reaction is stopped after 10 hours, and samples are taken from the protective reaction kettle 5 for analysis, wherein the product concentration is 95.50 percent, the intermediate product 3 ester concentration is 0.56 percent, and the excessive reactant 3,5 methyl ester concentration is 3.94 percent; after washing, crystallization and drying, the final product has the analysis concentration of 1010.42 percent, the concentration of 3-ester of the intermediate product is 0.32 percent, and the concentration of excessive 3, 5-methyl ester of the reactant is 1.26 percent, which shows that the reaction is relatively thorough and meets the requirements of industrial indexes.
The invention has the beneficial effects that the invention discloses a method for continuously preparing antioxidant 1010, which comprises the following steps: firstly, a solid-phase reactant pentaerythritol is dissolved in another liquid-phase reactant methyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate in a batching kettle, and then the solid-phase reactant pentaerythritol is sequentially passed through a first-stage reaction kettle, a second-stage reaction kettle and a protective reaction kettle, wherein the three reaction kettles are gradually heated under the same pressure, and finally the whole reaction is completed in the protective reaction kettle. The three reaction kettles control the reaction temperature through steam or heat conducting oil, and control the retention time through liquid level adjustment or discharging the height of each U-shaped bend. The final product can be obtained by the processes of conventional washing, crystallization, drying and the like of the product after the reaction is finished. The preparation method adopts a multistage series stirred tank type continuous reaction device, can flexibly react and operate conditions, effectively overcomes the defects of long operation period, incomplete reaction, high byproduct content and high labor intensity of the conventional intermittent production device, and improves the product yield.
The above detailed description is provided for a method for continuously preparing antioxidant 1010 provided in the examples of the present application, and the principle and the embodiments of the present application are explained in the present application by applying specific examples, and the description of the above examples is only used to help understanding the technical scheme and the core concept of the present application; those of ordinary skill in the art will understand that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; such modifications or substitutions do not depart from the spirit and scope of the present disclosure as defined by the appended claims.
Claims (10)
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| CN114790140A (en) * | 2022-04-01 | 2022-07-26 | 陕西艾科莱特新材料有限公司 | A kind of continuous preparation method of antioxidant 1076 |
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