CN114736122A - Reaction circulation rectification process method for producing ethyl methyl carbonate and diethyl ester - Google Patents
Reaction circulation rectification process method for producing ethyl methyl carbonate and diethyl ester Download PDFInfo
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- CN114736122A CN114736122A CN202210559587.4A CN202210559587A CN114736122A CN 114736122 A CN114736122 A CN 114736122A CN 202210559587 A CN202210559587 A CN 202210559587A CN 114736122 A CN114736122 A CN 114736122A
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- carbonate
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- ethyl methyl
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 34
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 3
- 239000007791 liquid phase Substances 0.000 claims abstract description 37
- 239000012071 phase Substances 0.000 claims abstract description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims abstract description 28
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000007788 liquid Substances 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 230000000737 periodic effect Effects 0.000 claims abstract description 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
- 150000002148 esters Chemical group 0.000 claims abstract description 4
- 230000003068 static effect Effects 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000011949 solid catalyst Substances 0.000 claims description 7
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 5
- 238000011068 loading method Methods 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000557 Nafion® Polymers 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 238000005265 energy consumption Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000000066 reactive distillation Methods 0.000 description 3
- 230000004907 flux Effects 0.000 description 2
- 238000000819 phase cycle Methods 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
The invention discloses a reaction circulating rectification process method for producing ethyl methyl carbonate and diethyl carbonate. In the gas phase operation stage, liquid is static on a tower tray, steam flows to a condenser from a reboiler, gas-liquid two phases are subjected to mass transfer on the tower tray and perform ester exchange reaction in a liquid phase of the tower tray; during the liquid phase operation phase, the vapor stops and the liquid moves between the trays; the cyclic operation of the gas phase and the liquid phase is realized by a tower internal part which is provided with a valve and a gate chamber positioned below the tower tray; during the gas phase operation phase, the valve on the tray is closed; in the liquid phase operation stage, a valve is opened, liquid flows to a lower lock chamber from a tray, the periodic feeding of raw materials dimethyl carbonate and ethanol is completed, an azeotrope of dimethyl carbonate and methanol is extracted from the top of a reaction rectifying tower, and ethyl methyl carbonate and diethyl carbonate are extracted from the bottom of the tower.
Description
Technical Field
The invention relates to reaction and rectification process enhancement, relates to a production method of ethyl methyl carbonate and diethyl carbonate serving as lithium battery electrolyte solvents, and particularly relates to a reaction cyclic rectification process method for producing ethyl methyl carbonate and diethyl carbonate.
Background
The reactive distillation is used as an important means for strengthening the process, is applied to systems such as esterification, hydrolysis, ester exchange, disproportionation and the like, can obviously increase the yield of a target product in the process with limited balance and reduce the energy consumption and equipment investment in the reaction and separation processes. However, due to the space limitation of the tray space, the loading capacity of the catalyst is limited, so that the reaction residence time is not easy to control, and especially the single-pass conversion rate of the reaction rectification process of the system with reaction rate control is restricted. The gas-liquid cross flow contact in the tower plate generates two-phase mass transfer and heat transfer, the loading of the catalyst obviously increases the flow resistance of the liquid phase, and the treatment capacity and the mass transfer efficiency of the conventional reaction rectifying tower are obviously reduced due to the limitation of the fluid mechanical properties of the tower plate such as entrainment of gas-phase mist and the like, thereby influencing the energy consumption of the process.
Ester exchange between ethanol and dimethyl carbonate is generally adopted for producing ethyl methyl carbonate and diethyl carbonate, but in the heterogeneous catalysis process, due to the limitation of reaction rate, a longer reaction residence time is required, so that a pre-reactor is required before raw materials enter a reaction rectifying tower to achieve the conversion rate target of the process, and in the reaction rectifying tower, due to the limitation of tower plate residence time, the conversion rate of the raw materials dimethyl carbonate is limited, so that the difficulty of subsequent separation and purification of ethyl methyl carbonate and diethyl carbonate is increased. And the flux of the reactive distillation column is limited due to the direct loading of solid catalysts such as the alkali metal oxide MgO/HZSM-5 on the trays.
Disclosure of Invention
Aiming at the problems of large liquid phase flow resistance, limited reaction residence time, low conversion rate per pass of raw materials and separation efficiency of a column plate, high process energy consumption and the like in the process of the existing reaction rectifying tower, the invention aims to provide a reaction circulation rectifying process method for producing ethyl methyl carbonate and diethyl carbonate.
In order to achieve the purpose, the technical scheme provided by the invention is as follows: the invention discloses a reaction circulation rectification process method for producing ethyl methyl carbonate and diethyl carbonate, which divides the operation process of reaction rectification into gas phase and liquid phase periodic operation, wherein in the gas phase operation stage, the liquid phase is static on a tower tray and generates mass and heat transfer between the gas phase and the liquid phase, the esterification reaction is carried out in the liquid phase on the tower tray of the reaction rectification section, and the gas phase is provided by a reboiler and flows to a condenser; in the liquid phase operation stage, the steam flowing in the tower stops, a valve on the tower plate is opened to flow to a lock chamber below the tower plate, and the feeding of raw materials dimethyl carbonate and ethanol, azeotropic mixtures of dimethyl carbonate and methanol, which are products at the top of the tower, and the extraction of methyl ethyl carbonate and diethyl carbonate, which are products at the bottom of the tower, are finished; at the beginning of the next gas phase operation period, the gate chamber is opened to enable the liquid to flow to the next layer of tower plate period to realize the mass and heat transfer and reaction process of the gas-liquid phase.
The invention is technically characterized in that: the invention divides the reaction rectification process into gas phase and liquid phase cycle operation by utilizing the tower plate with a valve and a lower lock chamber, thereby realizing the production of the methyl ethyl carbonate and the diethyl carbonate.
In the invention, the preferable pressure of the reaction circulating rectifying tower is 50-150Kpa, and the periodic operation time ratio of the gas phase to the liquid phase is preferably 2: 1-10: 1.
In the invention, the solid catalyst filled in the tower plate in the reactive distillation tower section is preferably alkali metal oxide MgO/HZSM-5, strong acid type ion exchange resin Lewatit K1221, Nafion SAC-13, modified K coated by polyethylene glycol2CO3。
In the invention, the reaction circulation rectification common rectification section tower plate is preferably 3-30, the reaction rectification section tower plate is preferably 4-30, the common stripping section tower plate is preferably 4-30, and the reflux ratio of the reaction rectification tower is preferably 1: 1-10: 1.
The mol ratio of dimethyl carbonate to ethanol in the feed is preferably 0.5: 1-1: 2, the one-way conversion rate of dimethyl carbonate in a reaction circulating rectifying tower is 50-90%, the yield of ethyl methyl carbonate is 35-60%, the yield of diethyl carbonate is 5-20%, the selectivity of ethyl methyl carbonate in the reaction circulating rectifying tower is 70-95%, and the selectivity of diethyl carbonate in the reaction circulating rectifying tower is 10-30%.
The invention has the beneficial effects that:
1. the invention adopts reaction circulation rectification to realize the serial reaction of dimethyl carbonate and ethanol, and the one-way conversion rate of the dimethyl carbonate is obviously improved.
2. The invention adopts a circulating operation mode to avoid the reduction of mass transfer efficiency caused by entrainment of gas-phase entrainment on the tower plate and obviously improve the flux of the reaction rectification process.
3. The loading of the catalyst for the reaction cyclic rectification on the reaction rectification tower plate can be flexibly adjusted, and the reaction residence time of the liquid phase can be flexibly adjusted so as to improve the conversion rate of dimethyl carbonate and the yield of target products, namely ethyl methyl carbonate and diethyl carbonate.
4. The gas-liquid phase independent period operation in the reaction circulation rectification process of the invention ensures that the distribution of the liquid phase on the tower plate tends to be uniform, and the flow resistance caused by the filling of the catalyst on the tower plate is obviously reduced.
5. In the reaction circulation rectification process, the energy consumption is obviously reduced compared with the conventional reaction rectification process due to the improvement of the reaction and separation efficiency under the circulation operation mode.
Drawings
FIG. 1 is a schematic diagram of the gas and liquid phase cycle operation of the reactive cycle rectification. Wherein VFP is a gas phase operation stage and LFP is a liquid phase operation stage; NVFP is the next gas phase operation period; CRS is a common rectifying section, RDS is a reaction rectifying section, CSS is a common stripping section, R101 is a reboiler of a reaction circulation rectifying tower, C101 is a condenser of the reaction circulation rectifying tower, MT is a tower plate with a switch valve and a lock chamber, and MRT is a reaction rectifying tower plate with a switch valve and a lock chamber and filled with a solid catalyst.
Detailed Description
The present invention will be described in more detail by the following embodiments with reference to the attached drawings, but the present invention is not limited by the scope of the claims of the present application.
The invention relates to a reaction circulating rectification process method for producing ethyl methyl carbonate and diethyl carbonate, which has the specific implementation mode that:
the reaction circulation rectification is divided into a periodic gas phase and liquid phase operation stage, in the gas phase operation stage, a liquid phase is static on a tower plate and performs mass and heat transfer with an ascending gas phase to perform liquid phase esterification reaction; in the liquid phase operation stage, liquid on the tower plate enters a lock chamber below the tower plate through opening of a valve on the tower plate, and the feeding of dimethyl carbonate and ethanol as raw materials, the azeotrope of dimethyl carbonate and methanol as a tower top product and the extraction of ethyl methyl carbonate and diethyl carbonate as a tower bottom product are completed; at the beginning of the next gas phase operation period, the gate chamber is opened to enable the liquid to flow to the next layer of tower plate period to realize the mass and heat transfer and reaction process of the gas-liquid phase.
The rectifying tower plate and the reactive rectifying tower plate used in the reactive circulating rectifying tower are realized by adopting tower plates which are provided with valves and lower lock chambers, wherein the reactive rectifying tower plate is filled with a solid catalyst.
Example 1
The feeding molar ratio of dimethyl carbonate to ethanol in the raw materials is set to be 1: 1, the number of the reaction circulating rectification public rectification section tower plates is 15, the number of the reaction rectification section tower plates is 20, the number of the public stripping section tower plates is 30, the operation pressure is 101.325Kpa, the gas phase period operation time is 35s, the liquid phase period operation time is 5s, the catalyst filled on the reaction rectification section tower plates is alkali metal oxide MgO/HZSM-5, the filling amount of the solid catalyst on the reaction rectification tower plates is 30Kg, the period circulating feeding amount is 0.4kmol/cycle, and the vapor amount in the gas phase operation stage is 1 kmol/min.
After the dimethyl carbonate and the ethanol raw materials are subjected to the process, the single-pass conversion rate of the dimethyl carbonate is 65%, the single-pass yield of the ethyl methyl carbonate is 54.2%, the single-pass yield of the diethyl carbonate is 10.8%, the single-pass conversion rate of the ethanol is 100%, the selectivity of the ethyl methyl carbonate is 83.4%, the selectivity of the diethyl carbonate is 16.6%, the periodic extraction amount at the top of the tower is 0.27kmol/cycle, the periodic extraction amount at the bottom of the tower is 0.13kmol/cycle, the energy consumption is reduced by 20.5% compared with that in the traditional reaction rectification process, and the single-pass conversion rate of the dimethyl carbonate is improved by 43.4%.
Example 2
The feeding molar ratio of dimethyl carbonate to ethanol in the raw materials is set to be 1.2: 1, the number of the reaction circulating rectification common rectification section tower plates is 15, the number of the reaction rectification section tower plates is 25, the number of the common stripping section tower plates is 30, the operation pressure is 101.325Kpa, the gas phase period operation time is 40s, the liquid phase period operation time is 5s, the catalyst filled on the reaction rectification section tower plates is alkali metal oxide MgO/HZSM-5, the filling amount of the solid catalyst on the reaction rectification tower plates is 35Kg, the period circulating feeding amount is 0.44kmol/cycle, and the vapor amount in the gas phase operation stage is 1.2 kmol/min.
After the dimethyl carbonate and the ethanol raw materials are subjected to the process, the single-pass conversion rate of the dimethyl carbonate is 62%, the single-pass yield of the ethyl methyl carbonate is 50.2%, the single-pass yield of the diethyl carbonate is 11.8%, the single-pass conversion rate of the ethanol is 100%, the selectivity of the ethyl methyl carbonate is 81.0%, the selectivity of the diethyl carbonate is 19.0%, the periodic extraction amount at the top of the tower is 0.2912kmol/cycle, the periodic extraction amount at the bottom of the tower is 0.1488kmol/cycle, the energy consumption is reduced by 22.4% compared with that in the traditional reaction rectification process, and the single-pass conversion rate of the dimethyl carbonate is improved by 40.8%.
Claims (7)
1. A reaction circulation rectification process method for producing ethyl methyl carbonate and diethyl ester is characterized in that the reaction rectification process for producing ethyl methyl carbonate and diethyl carbonate is divided into an independent gas phase operation stage and a liquid phase operation stage, in the gas phase operation stage, liquid is static on a tower tray, steam flows to a condenser from a reboiler in a tower, and gas-liquid two phases generate mass and heat transfer on a tower plate and perform ester exchange chemical reaction in the liquid phase of the tower plate; during the liquid phase operation phase, the flow of vapor is stopped and liquid moves between trays; the cyclic operation of the gas phase and the liquid phase is realized by a tower internal part which is provided with a valve and a gate chamber positioned below the tower tray; the rules for the periodic operation are: in the gas phase operation stage, the valve on the tray is closed, and the liquid phase is kept unchanged on the tray; in the liquid phase operation stage, a valve is opened, liquid flows to a lower lock chamber from a tray, the periodic feeding of raw materials dimethyl carbonate and ethanol is completed, an azeotrope of dimethyl carbonate and methanol is extracted from the top of a reaction rectifying tower, and reaction products of ethyl methyl carbonate and diethyl carbonate are extracted from a tower kettle; at the beginning of another vapor flow cycle, the chamber opens liquid to the tray below.
2. The reactive cyclic rectification process for producing ethyl methyl carbonate and diethyl carbonate as claimed in claim 1, wherein the operation mode of the reactive rectification process is divided into a gas phase operation stage and a liquid phase operation stage, and the operation time, the gas phase period operation gas quantity, the tray liquid holdup and the catalyst loading of the gas phase and liquid phase operation stages are adjusted according to the feed flow.
3. The reactive recycling rectification process for producing ethyl methyl carbonate and diethyl carbonate as claimed in claim 1, wherein the reactive rectification column is divided into a common rectification section, a reactive rectification section and a common stripping section, wherein dimethyl carbonate is periodically fed between the common rectification section and the reactive rectification section, and ethanol is periodically fed between the reactive rectification section and the common stripping section.
4. The reactive cyclic rectification process for producing ethyl methyl carbonate and diethyl carbonate as claimed in claim 1, wherein the cyclic operation of the gas-liquid phase is performed by column internals comprising trays, switching valves, and a gate chamber below the trays, the gate chamber being provided to prevent the liquid phases of adjacent trays from mixing.
5. The cyclic rectification process for preparing ethyl methyl carbonate and diethyl carbonate as claimed in claim 1, wherein the catalyst filled on the tower plate of the reaction rectification section is solid catalyst selected from alkali metal oxide MgO/HZSM-5, strong acid ion exchange resin Lewatit K1221 and Nafion SAC-13, and modified K coated with polyethylene glycol is used2CO3。
6. The reaction circulating rectification process method for producing the ethyl methyl carbonate and the diethyl carbonate according to claim 1, which is characterized in that the number of the reaction circulating rectification common rectification section tower plates is 10-20, the number of the reaction rectification section tower plates is 15-35, the number of the common stripping section tower plates is 20-40, the molar ratio of dimethyl carbonate to ethanol in feeding is 2: 1-0.5: 1, and the operating pressure is 50-150 Kpa.
7. The reaction circulation rectification process method for producing the ethyl methyl carbonate and the diethyl carbonate according to claim 1, characterized in that the time ratio of gas phase operation to liquid phase operation is preferably 3: 1-12: 1, and the ratio of the product ethyl methyl carbonate to the diethyl carbonate is preferably 3: 1-6: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210559587.4A CN114736122B (en) | 2022-05-23 | 2022-05-23 | Reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl ester |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210559587.4A CN114736122B (en) | 2022-05-23 | 2022-05-23 | Reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl ester |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040044239A1 (en) * | 2000-07-24 | 2004-03-04 | Hironori Haga | Method for producing polycarbonate |
| DE102004031207A1 (en) * | 2004-06-28 | 2006-01-19 | Basf Ag | Preparation of (meth)acrylic acid ester, comprises preparing a reaction mixture by catalytic gas phase partial oxidation, absorbing mixture, desorbing the absorbent and esterifying (where water is not reversed into the rectification unit) |
| CN109369400A (en) * | 2018-10-15 | 2019-02-22 | 沈阳化工大学 | A kind of solid base catalyst is directly catalyzed the production technology of high-purity diethyl carbonate |
| CN215886875U (en) * | 2021-07-26 | 2022-02-22 | 华东理工大学 | Reaction separation device for efficiently and continuously preparing ethyl methyl carbonate |
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2022
- 2022-05-23 CN CN202210559587.4A patent/CN114736122B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040044239A1 (en) * | 2000-07-24 | 2004-03-04 | Hironori Haga | Method for producing polycarbonate |
| DE102004031207A1 (en) * | 2004-06-28 | 2006-01-19 | Basf Ag | Preparation of (meth)acrylic acid ester, comprises preparing a reaction mixture by catalytic gas phase partial oxidation, absorbing mixture, desorbing the absorbent and esterifying (where water is not reversed into the rectification unit) |
| CN109369400A (en) * | 2018-10-15 | 2019-02-22 | 沈阳化工大学 | A kind of solid base catalyst is directly catalyzed the production technology of high-purity diethyl carbonate |
| CN215886875U (en) * | 2021-07-26 | 2022-02-22 | 华东理工大学 | Reaction separation device for efficiently and continuously preparing ethyl methyl carbonate |
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