CN114230450B - Methyl propionate synthesis process device utilizing coupling hydrogenation reaction rectifying tower - Google Patents

Methyl propionate synthesis process device utilizing coupling hydrogenation reaction rectifying tower Download PDF

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CN114230450B
CN114230450B CN202111538651.2A CN202111538651A CN114230450B CN 114230450 B CN114230450 B CN 114230450B CN 202111538651 A CN202111538651 A CN 202111538651A CN 114230450 B CN114230450 B CN 114230450B
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tank
methyl propionate
outlet
reaction
hydrogenation
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CN114230450A (en
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向家勇
朱怀工
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Jiangsu Huda Chemical Technology Co ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/12Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/08Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/10Process efficiency

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The application discloses a methyl propionate synthesis process device utilizing a coupling hydrogenation reaction rectifying tower, which comprises a carbonylation reaction kettle, a flash evaporation tank, the reaction rectifying tower and a split-phase tank, wherein a subsequent separation procedure of acid and ester is omitted by adopting the baffle reaction rectifying tower, meanwhile, the CO-production of methyl propionate and alcohol, methyl butyrate, ethyl butyrate and other byproducts are realized by taking low-cost methanol and CO as raw materials through a coupling hydrogenation unit and a split-phase liquid separation process, and multistage heat exchange is performed by adopting high-temperature high-pressure gas phase after flash evaporation, so that the energy consumption is reduced fully and the production cost of products is further reduced. Compared with the traditional mode, the conversion rate of 95% of the methyl propionate synthesized by the method is improved to 99.5%, the equipment investment is reduced, the energy consumption is reduced by 60%, and meanwhile, the azeotropic product of the organic acid ester and the alcohol is synthesized by taking the methanol and the CO which are easy to obtain and low in cost as raw materials.

Description

Methyl propionate synthesis process device utilizing coupling hydrogenation reaction rectifying tower
Technical Field
The application belongs to the technical field of chemical production, and particularly relates to a production process device and method of methyl propionate.
Background
At present, the preparation process of methyl propionate is divided into two types: the process of coproducing propionate in the process of synthesizing propionic acid and the process of synthesizing methyl propionate by direct catalytic esterification, or the process of directly purchasing methyl propionate synthesized by propionic acid raw materials, has low economical efficiency. The process of synthesizing propionic acid is divided into two types, as follows:
one is that the propionate can be produced by using the ethylene hydroesterification process, and the propionate can be hydrolyzed to obtain propionic acid;
CH 2 =CH 2 +CO+CH 3 OHC 2 H 5 COOCH 3
the other is that the carbonylation reaction mainly comprises methanol and ethanol to synthesize propionic acid, and then esterification reaction is carried out to obtain methyl propionate;
CO+CH 3 CH 2 OHCH 3 CH 2 COOH
the ethylene productivity distribution in China is uneven, and is mainly distributed in eastern coastal areas, so that the ethylene is inconvenient to transport in long distances, and the transportation mode is that a pipeline is directly conveyed to a downstream factory device. The first way of producing propionic acid and propionate esters solely from ethylene fails to meet the needs of the western inland region for propionic acid and propionate ester products. Meanwhile, the coal chemical industry in China has a large amount of methanol, and the cost is low.
Therefore, many industries are processes for synthesizing propionic acid and propionate esters by ethanol carbonylation. The ethanol resource is excessive, the transportation is convenient, and the alcohol carbonylation process is an effective way for improving the added value of the methanol-ethanol product.
The traditional process is that propionic acid and methanol are added into a reaction kettle to synthesize methyl propionate under the action of a catalyst, then the methyl propionate is separated in a rectifying tower, a mixture of propionic acid and water is obtained in the tower kettle, a mixture of methyl propionate, methanol and water is obtained at the tower top and then is fed into an extraction tower, an extractant (a mixture of polyalcohol and water) is added into the extraction tower to extract the mixture, so that high-purity methyl propionate is obtained, and an extract liquid in the tower kettle is fed into a decompression tower to be treated, so that the extractant prepared by polyalcohol and water can be recycled. And separating the tower bottom product of the rectifying tower in a recovery tower, and recycling the propionic acid.
The process has the advantages of complex reaction flow, high equipment investment, increased raw material investment and energy consumption due to the use of the extractant, and higher production cost of methyl propionate due to the fact that raw material acid, methyl propionate and other products are mixed together and need to be separated.
The prior art CN112851507A also discloses a process for synthesizing methyl methacrylate by ethanol, which takes ethanol and CO as raw materials, synthesizes propionic acid by carbonylation under the action of a catalyst, then synthesizes methyl propionate by catalytic esterification with methanol, and finally obtains MMA by gas-phase aldol condensation with formaldehyde. In the method, ethanol and CO are adopted as raw materials, low-cost methanol cannot be utilized as raw materials, and meanwhile, the methyl propionate-containing product obtained after propionic acid esterification in the method also contains other acids and alcohols, so that the yield of subsequent aldol condensation reaction can be reduced, and especially, the heat energy of high-temperature and high-pressure gas after flash evaporation separation is not fully utilized, so that the cost of MMA products can be increased. Moreover, the presence of by-product water fed into aldol condensation and esterification reactions is detrimental to the forward progress of the reaction, and separation of by-product water is not described in the art, possibly resulting in a decrease in purity of product MMA and an increase in cost.
Disclosure of Invention
The application aims to: aiming at the problems and the defects existing in the prior art, the application aims to provide a baffle type methyl propionate reaction rectifying tower and a process device for coupling hydrogenation, which are used for realizing the synthesis of methyl propionate and alcohol by taking low-cost methanol and CO as raw materials, and obtaining low-cost methyl propionate and alcohol and the CO-production of polyesters such as methyl butyrate through a high-efficiency heat energy recovery technology.
The technical scheme is as follows: in order to solve the technical problems, the application adopts the following technical scheme: a methyl propionate synthesis process device utilizing a coupling hydrogenation reaction rectifying tower comprises a carbonylation reaction kettle, a flash tank, the reaction rectifying tower and a split-phase tank, wherein
The carbonylation reaction kettle is provided with a CO feed inlet and a reducing alcohol inlet, and an outlet of the carbonylation reaction kettle is connected with an inlet of the flash tank;
the top of the flash tank is provided with a gas phase outlet connected with the flash tank, and the bottom of the flash tank is also provided with a liquid phase outlet connected with the carbonylation reaction kettle;
the reaction rectifying tower comprises a tower body, a hydrogenation reactor and a partition plate for dividing the space in the tower body into a reaction area and a collecting area, wherein an organic acid feed inlet and a methanol feed inlet are respectively arranged at the upper part and the bottom of the reaction area of the tower body, a light component extraction outlet and a light component reflux port are arranged at the top of the collecting area of the tower body, and the light component extraction outlet is connected with a light component converging port after being connected with a phase splitting tank through a pipeline;
the middle lower section of the tower body collecting region is also provided with a product collecting outlet; the hydrogenation reactor is arranged at the top end of the tower body and is communicated with the tower body reaction zone, and the hydrogenation reactor is also provided with a hydrogen feed inlet and a reducing alcohol discharge outlet; the organic acid feed inlet is connected with the gas phase outlet of the flash tank through a pipeline;
the reduced alcohol discharge port of the hydrogenation reactor is connected with the inlet of the carbonylation reactor through a pipeline pump.
Preferably, the device further comprises a liquid separating tank and a first cooler, wherein the gas phase outlet of the flash tank is connected with the liquid separating tank through a pipeline, the bottom of the liquid separating tank is provided with a liquid phase outlet and is connected with an organic acid feed inlet of the reaction rectifying tower through a pipeline, the first cooler is arranged at the gas phase outlet of the flash tank, and heat exchange media in the first cooler are materials in the gas phase outlet of the flash tank and the liquid phase outlet of the liquid separating tank respectively.
Preferably, the reducing alcohol discharge port of the hydrogenation reactor is also provided with a bypass connected with the middle and lower sections of the tower body.
Preferably, the device also comprises a condenser arranged at the light component extraction outlet of the reactive distillation column, and the condenser is respectively connected with the split-phase tank inlet and the hydrogenation reactor inlet through pipelines.
Preferably, the hydrogenation reactor adopts a tubular reactor, and catalytic filler is arranged in the tubular reactor.
Preferably, one side of the collecting area of the reaction rectifying tower is also provided with a methyl propionate and methanol collecting outlet, an ethyl propionate collecting outlet and a methyl butyrate collecting outlet.
Preferably, the reaction zone of the reactive distillation column is circularly connected with a knapsack reactor through a pipeline.
Preferably, the flash tank gas phase outlet pipeline is positioned behind the first cooler and is also provided with a second cooler.
Preferably, the top end of the liquid separating tank is also provided with an outlet, and the liquid separating tank is connected with an inlet of the carbonylation reaction kettle through a pipeline pump.
The beneficial effects are that: compared with the prior art, the application has the following advantages: 1. the subsequent separation procedure of acid and ester is omitted through the separation plate; 2. the CO-production of methyl propionate and alcohol, methyl butyrate, ethyl butyrate and other byproducts is realized by using cheap methanol and CO as raw materials through a coupling hydrogenation unit and a split-phase liquid separation process; 3. the high-temperature high-pressure gas phase after flash evaporation is adopted for multi-stage heat exchange, so that the heat energy is fully utilized, the energy consumption is reduced, and the production cost of the product is further reduced. The external knapsack reactor makes the equipment compact and reduces the space occupied by operation. The application also omits an extraction section, reduces the use of solvents, has more environment-friendly flow, and is mainly used as pollutants in the tower top, non-condensable gas and esterification reaction to generate water.
Drawings
FIG. 1 is a schematic diagram of a methyl propionate synthesizing process device using a coupled hydrogenation reaction rectifying tower.
In the figure, a carbonylation reaction vessel 100, a flash tank 200, a reactive distillation column 300, a partition 310, a hydrogenation reactor 320, a split-phase tank 400, a split-phase tank 500, a first cooler 600, a second cooler 700, and a condenser 800 are shown.
Description of the embodiments
The present application is further illustrated in the accompanying drawings and detailed description which are to be understood as being merely illustrative of the application and not limiting of its scope, and various modifications of the application, which are equivalent to those skilled in the art upon reading the application, will fall within the scope of the application as defined in the appended claims.
As shown in FIG. 1, the application discloses a process device for producing methyl propionate by using methanol and CO, which is a process device for producing methyl propionate and methanol azeotrope by using methanol and CO as raw materials, and mainly comprises a carbonylation reaction section, an esterification reaction rectification section and a coupling hydrogenation section.
1. Carbonylation reaction section
The reaction content is as follows:
main reaction-carbonylation reaction: CH (CH) 3 OH+CO→CH 3 COOH
Main reaction-carbonylation reaction: CH (CH) 3 CH 2 OH+CO→CH 3 CH 2 COOH, propanol, butanol and CO are subjected to carbonylation reaction to synthesize corresponding acid.
Side reaction: and (3) transformation reaction: CO+H 2 O→CO 2 +H 2
In the present application, in the carbonylation reactor 100, carbon monoxide and methanol (methanol may be fed in the carbonylation reactor 100 and/or the reactive distillation column 300) are continuously reacted under certain conditions to produce acetic acid, and carbon monoxide and ethanol produced in the hydrogenation section at the top of the reactive distillation column are continuously reacted to produce propionic acid. The carbonylation reactor of the application can carry out the carbonylation reaction of mixed alcohol, and the reflux of the hydrogenation reaction is controlled according to the process requirement, so that the carbonylation reactor can be a mixture of methanol and/or ethanol.
The flow is as follows: the carbonylation reactor 100 has an operating temperature of 150-200 ℃ and an operating pressure of 2.5-3.5 MPa. In reactor 100, carbon monoxide and methanol/ethanol are continuously reacted to form acetic acid and/or propionic acid. The carbonylation reactor can carry out the carbonylation reaction of mixed alcohol, and the reflux of the hydrogenation reaction is controlled according to the process requirement, so that the carbonylation reactor can be a mixture of methanol and/or ethanol. The product containing acetic acid and/or propionic acid obtained by the carbonylation reaction enters a flash tank 200 for flash evaporation. The heavy components in flash tank 200 are returned to carbonylation reactor 100 by a pump. The light component goes to the first cooler 600 to be partially condensed (the condensing medium at the position adopts the liquid phase component at the bottom of the liquid separating tank and can fully utilize the heat of the liquid phase component), the liquid separating tank 500 is cooled to be split in phase, the liquid separating tank is pressurized, the pressure is controlled to be about 1MpaG, after the liquid separating, the bottom liquid phase (mainly acetic acid and propionic acid) is pressed into the reactive distillation section to be subjected to esterification reaction and rectification, and is taken as a cooling medium to cool the light component of the flash tank through the first cooler 600, and when the cooling temperature is less than the requirement, the flash tank can be cooled again through the second cooler 700; the top gas of the liquid separating tank 500 is pressed into the carbonylation reactor 100 by a booster fan (F101); the incompressible light component gas is discharged to a tail gas treatment system for absorption and incineration.
2. Reaction rectifying hydrogenation coupling section
The flow is briefly described: the reaction rectifying tower 300 adopts a design of coupling a partition tower and hydrogenation reaction, namely: a side plate is vertically arranged in the reaction rectifying tower, and the internal space of the reaction rectifying tower is divided into a reaction zone and a product extraction zone; meanwhile, a hydrogenation reactor which is communicated and coupled with the reaction zone is arranged at the top of the tower.
Propionic acid and acetic acid are fed at the upper part of the catalytic rectification reaction side (A), and methanol is fed at the lower bottom of the catalytic rectification side (A). And (3) performing an esterification reaction to mainly generate methyl acetate and methyl propionate. The side line is pumped out by a pump and is pumped back into the tower after further reaction in the knapsack reactor, so that the reaction efficiency and speed are improved, the tower height can be reduced, and the occupied area can be reduced.
Methyl acetate and methyl propionate generated by esterification reaction at the catalytic rectifying side A of the reactive rectifying tower, methyl butyrate and/or ethyl butyrate and other recombination downflows enter a product extraction area at the other side, and a gas phase light component part directly enters a hydrogenation reactor to obtain corresponding reducing alcohol, and enters a cooler and then is partially returned to a carbonylation reaction kettle, and a part of the gas phase light component part is sent to the reactive rectifying tower to continue to react; at the same time, the light component part at the top of the reactive rectifying tower is extracted, condensed by a condenser 800, the condensing temperature is controlled at about 62.5 ℃, the condensate enters a phase-splitting tank 400, the ester phase is totally refluxed, and the water phase automatically flows to the inlet of a water extraction pump. E103 gas phase mainly consists of azeotropes of methyl acetate, methanol and water, gas phase flows back into a hydrogenation reactor 320 at the top of a reaction rectifying tower, methanol, ethanol and the like are generated by reaction, finally, the mixture is condensed by a cooler and then enters a liquid separating tank 500, liquid phase is pumped back into a carbonylation reactor 100 by a pump, and the gas phase is removed from a tail gas treatment system to be absorbed and incinerated.
The reactive distillation process has total reflux of the ester phase at the top of the tower, and the azeotropic product of methyl propionate and methanol, and the products of methyl propionate, methyl butyrate, ethyl butyrate, and the like are extracted from the side line by a pump. The water produced in the catalytic reaction process in the reactive distillation column is also extracted from the side line by a pump.
The application removes the product from the reaction system in time, which can break the original balance, promote the forward reaction, improve the conversion rate of the reactant, and compared with the traditional method, the conversion rate is 95%, and the reaction rectification process can improve the conversion rate to 99.5%. The separation plate reaction rectification and coupling hydrogenation process replaces the functions of a reaction kettle, a rectification tower and a recovery tower in the traditional process, reduces equipment investment, reduces energy consumption by 60 percent, and simultaneously realizes the synthesis of the azeotropic product of the organic acid ester and the alcohol by taking the methanol and the CO which are easy to obtain and low in cost as raw materials.
It is to be understood that these examples are for the purpose of illustrating the application only and are not to be construed as limiting the scope of the application, since modifications to the application, which are various equivalent to those skilled in the art, will fall within the scope of the application as defined in the appended claims after reading the application.

Claims (8)

1. A methyl propionate synthesis process device utilizing a coupling hydrogenation reaction rectifying tower is characterized in that: comprises a carbonylation reaction kettle, a flash evaporation tank, a reaction rectifying tower and a split-phase tank, wherein
The carbonylation reaction kettle is provided with a CO feed inlet and a reducing alcohol inlet, and an outlet of the carbonylation reaction kettle is connected with an inlet of the flash tank;
the top of the flash tank is provided with a gas phase outlet connected with the flash tank, and the bottom of the flash tank is also provided with a liquid phase outlet connected with the carbonylation reaction kettle;
the reaction rectifying tower comprises a tower body, a hydrogenation reactor and a partition plate for dividing the space in the tower body into a reaction area and a collecting area, wherein an organic acid feed inlet and a methanol feed inlet are respectively arranged at the upper part and the bottom of the reaction area of the tower body, a light component extraction outlet and a light component reflux inlet are arranged at the top of the collecting area of the tower body, and the light component extraction outlet is connected with the light component reflux inlet after being connected with the phase separation tank through a pipeline;
the middle lower section of the tower body collecting region is also provided with a product collecting outlet; the hydrogenation reactor is arranged at the top end of the tower body and is communicated with the tower body reaction zone, and the hydrogenation reactor is also provided with a hydrogen feed inlet and a reducing alcohol discharge outlet; the organic acid feed inlet is connected with the gas phase outlet of the flash tank through a pipeline;
the reducing alcohol discharge port of the hydrogenation reactor is connected with the inlet of the carbonylation reactor through a pipeline pump;
the flash distillation tank is characterized by further comprising a liquid separating tank and a first cooler, wherein a gas phase outlet of the flash distillation tank is connected with the liquid separating tank through a pipeline, a liquid phase outlet is arranged at the bottom of the liquid separating tank and is connected with an organic acid feed inlet of the reaction rectifying tower through a pipeline, the first cooler is arranged at the gas phase outlet of the flash distillation tank, and heat exchange media in the first cooler are materials in the gas phase outlet of the flash distillation tank and the liquid phase outlet of the liquid separating tank respectively.
2. The methyl propionate synthesis process apparatus using a coupled hydrogenation reaction rectifying column as claimed in claim 1, wherein: the reduced alcohol discharge port of the hydrogenation reactor is also provided with a bypass connected with the middle and lower sections of the tower body.
3. The methyl propionate synthesis process apparatus using a coupled hydrogenation reaction rectifying column as claimed in claim 1, wherein: the device also comprises a condenser arranged at the light component extraction outlet of the reactive distillation column, and the condenser is respectively connected with the split-phase tank inlet and the hydrogenation reactor inlet through pipelines.
4. The methyl propionate synthesis process apparatus using a coupled hydrogenation reaction rectifying column as claimed in claim 1, wherein: the hydrogenation reactor adopts a tubular reactor, and catalytic filler is arranged in the tubular reactor.
5. The methyl propionate synthesis process apparatus using a coupled hydrogenation reaction rectifying column as claimed in claim 1, wherein: and one side of the collecting area of the reaction rectifying tower is also provided with a methyl propionate and methanol collecting outlet, an ethyl propionate collecting outlet and a methyl butyrate collecting outlet.
6. The methyl propionate synthesis process apparatus using a coupled hydrogenation reaction rectifying column as claimed in claim 1, wherein: the reaction zone of the reactive rectifying tower is circularly connected with a knapsack reactor through a pipeline.
7. The methyl propionate synthesis process apparatus using a coupled hydrogenation reaction rectifying column as claimed in claim 1, wherein: the flash tank gas phase outlet pipeline is positioned behind the first cooler and is also provided with a second cooler.
8. The methyl propionate synthesis process apparatus using a coupled hydrogenation reaction rectifying column as claimed in claim 1, wherein: the top end of the liquid separating tank is also provided with an outlet, and is connected with an inlet of the carbonylation reaction kettle through a pipeline pump.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN203033918U (en) * 2012-12-20 2013-07-03 上海戊正工程技术有限公司 Process system for indirectly producing ethanol by using synthesis gases
CN110613946A (en) * 2019-10-25 2019-12-27 福州大学 Backpack reaction rectification equipment for synthesizing diethyl oxalate and process thereof
CN111298471A (en) * 2020-03-30 2020-06-19 吴嘉 Dividing wall rectifying tower for separating complex multi-component system and rectifying method
CN112851507A (en) * 2021-01-25 2021-05-28 西南化工研究设计院有限公司 Process for synthesizing methyl methacrylate by ethanol

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN203033918U (en) * 2012-12-20 2013-07-03 上海戊正工程技术有限公司 Process system for indirectly producing ethanol by using synthesis gases
CN110613946A (en) * 2019-10-25 2019-12-27 福州大学 Backpack reaction rectification equipment for synthesizing diethyl oxalate and process thereof
CN111298471A (en) * 2020-03-30 2020-06-19 吴嘉 Dividing wall rectifying tower for separating complex multi-component system and rectifying method
CN112851507A (en) * 2021-01-25 2021-05-28 西南化工研究设计院有限公司 Process for synthesizing methyl methacrylate by ethanol

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