CN114736122B - Reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl ester - Google Patents
Reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl ester Download PDFInfo
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- CN114736122B CN114736122B CN202210559587.4A CN202210559587A CN114736122B CN 114736122 B CN114736122 B CN 114736122B CN 202210559587 A CN202210559587 A CN 202210559587A CN 114736122 B CN114736122 B CN 114736122B
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- methyl ethyl
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 35
- 230000008569 process Effects 0.000 title claims abstract description 35
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 2
- 239000007791 liquid phase Substances 0.000 claims abstract description 43
- 239000012071 phase Substances 0.000 claims abstract description 39
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 230000000737 periodic effect Effects 0.000 claims abstract description 19
- 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
- 239000011949 solid catalyst Substances 0.000 claims abstract description 10
- 230000003068 static effect Effects 0.000 claims abstract description 4
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 8
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 5
- 238000011068 loading method Methods 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 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
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 description 8
- 238000005265 energy consumption Methods 0.000 description 6
- 238000000066 reactive distillation Methods 0.000 description 6
- 238000011049 filling Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 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 description 1
- 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
- 230000008859 change 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
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The application discloses a reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl carbonate, wherein a solid catalyst is filled on a column plate of a reaction rectification section, and the reaction rectification process for producing the methyl ethyl carbonate and the diethyl carbonate is divided into an independent gas phase stage and a liquid phase stage. In the gas phase operation stage, liquid is static on a tray, steam flows from a reboiler to a condenser, gas-liquid two phases transfer mass and heat on a tray and perform transesterification in the tray liquid phase; during the liquid phase operation phase, the vapor stops and the liquid moves between trays; the periodic operation of the gas phase and the liquid phase is realized by a tower internal member provided with a valve and a gate chamber positioned below the 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 from a tray to a gate chamber below, periodic feeding of raw materials of dimethyl carbonate and ethanol is completed, an azeotrope of the dimethyl carbonate and the methanol is extracted from the top of a reaction rectifying tower, and methyl ethyl carbonate and diethyl carbonate are extracted from the bottom of the tower.
Description
Technical Field
The application relates to reinforcement of reaction and rectification processes, relates to a production method of methyl ethyl carbonate and diethyl carbonate serving as electrolyte of a lithium battery, and in particular relates to a reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl carbonate.
Background
The reactive distillation is used as an important means for strengthening the process, is applied to esterification, hydrolysis, transesterification, disproportionation reaction and other systems, can obviously increase the yield of target products for the process with limited balance, and reduces the energy consumption and equipment investment in the reaction and separation process. However, due to space limitation of tray space, the loading capacity of the catalyst is limited, so that the reaction residence time is not easy to control, and particularly, the single pass conversion rate of the reactive rectification process of a system with the reaction rate control can be limited. 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 processing capacity and the mass transfer efficiency of the conventional reaction rectifying tower are obviously reduced due to the limitation of the hydrodynamic property of the tower plate such as gas phase entrainment and the like, thereby influencing the process energy consumption.
The transesterification between ethanol and dimethyl carbonate is usually adopted for producing methyl ethyl carbonate and diethyl carbonate, but in the heterogeneous catalysis process, a longer reaction residence time is required due to the limitation of the reaction rate, so that the conversion rate of the process is aimed by passing through a pre-reactor before the raw material enters a reaction rectifying tower, and the conversion rate of the raw material dimethyl carbonate is limited in the reaction rectifying tower due to the limitation of the residence time of a tower plate, so that the difficulty of separating and purifying the subsequent methyl ethyl carbonate and diethyl carbonate is increased. And the flux of the reactive distillation column is limited due to the direct packing of the solid catalyst such as the alkali oxide MgO/HZSM-5 on the trays.
Disclosure of Invention
Aiming at the problems of high liquid phase flow resistance, limited reaction residence time, low single-pass conversion rate of raw materials, low separation efficiency of tower plates, high process energy consumption and the like in the conventional reaction rectifying tower process, the application aims to provide a reaction circulation rectifying process method for producing methyl ethyl carbonate and diethyl carbonate, which can flexibly change the filling amount of a catalyst, increase the conversion rate and the yield of a target product by precisely controlling the residence time of liquid phase reaction, ensure that the liquid phase is distributed more uniformly on the tower plates through independent operation of gas and liquid phases, reduce the flow resistance of the liquid phase on the tower plates and remarkably increase the flux and the separation performance of the process.
In order to achieve the above purpose, the technical scheme provided by the application is as follows: the application discloses a reaction circulation rectification process method for producing methyl ethyl 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 tray, mass and heat transfer between the gas phase and the liquid phase occur, the esterification reaction is carried out in the liquid phase on a tray of a reaction rectification section, and the gas phase is provided by a reboiler and flows to a condenser; in the liquid phase operation stage, steam flowing in the tower is stopped, a valve on a tower plate opens a sluice chamber below the tower plate, and feeding of raw materials of dimethyl carbonate and ethanol, extraction of an azeotrope of a tower top product of dimethyl carbonate and methanol and extraction of a tower bottom product of methyl ethyl carbonate and diethyl carbonate are completed; and when the next gas phase operation period starts, the sluice chamber opens the liquid flow to the next layer of tower plate period to realize the mass transfer heat transfer and reaction process of the gas phase and the liquid phase.
The application is technically characterized in that: the application divides the reactive distillation operation process into gas phase and liquid phase periodic operation by utilizing the tower plate with the valve and the lower lock chamber, thereby realizing the production of the process of methyl ethyl carbonate and diethyl carbonate.
In the present application, the preferable pressure of the reaction circulation rectifying column is 50 to 150Kpa, and the ratio of the gas phase to the liquid phase cycle operation time is preferably 2:1 to 10:1.
In the application, the solid catalyst filled in the tower plate in the reaction rectifying tower section is preferably alkali metal oxide MgO/HZSM-5, and the strong acid ion exchange resin Lewatit K1221 and Nafion SAC-13 adopts polyethylene glycol coated modified K 2 CO 3 。
In the application, the common rectifying section tower plate of the reaction circulation rectification is preferably 3-30, the common rectifying section tower plate of the reaction rectification is preferably 4-30, the common stripping section tower plate is preferably 4-30, and the reflux ratio of the reaction rectifying tower is preferably 1:1-10:1.
In the application, the molar ratio of the dimethyl carbonate to the ethanol in the feed is preferably 0.5:1-1:2, the single pass conversion rate of the dimethyl carbonate in the reaction cycle rectifying tower is 50-90%, the yield of the methyl ethyl carbonate is 35-60%, the yield of the diethyl carbonate is 5-20%, the selectivity of the methyl ethyl carbonate in the reaction cycle rectifying tower is 70-95%, and the selectivity of the diethyl carbonate in the reaction cycle rectifying tower is 10-30%.
The application has the beneficial effects that:
1. the application adopts the reaction circulation rectification to realize the continuous reaction of the dimethyl carbonate and the ethanol, and the single pass conversion rate of the dimethyl carbonate is obviously improved.
2. The application adopts a circulating operation mode, avoids the reduction of mass transfer efficiency caused by entrainment of gas phase on the tower plate, and obviously improves the flux of the reactive distillation process.
3. The loading of the catalyst for reaction circulation rectification on the reaction rectification column 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 the dimethyl carbonate and the yield of target products of the methyl ethyl carbonate and the diethyl carbonate.
4. The gas-liquid phase independent periodic operation in the reaction circulation rectification process leads the liquid phase distribution on the tower plate to be uniform, and obviously reduces the flow resistance caused by the filling of the catalyst on the tower plate.
5. Compared with the conventional reaction rectification process, the energy consumption of the reaction circulation rectification process is obviously reduced due to the improvement of the reaction and separation efficiency in the circulation operation mode.
Drawings
FIG. 1 is a schematic diagram of the periodic operation of the vapor and liquid phases of a reactive cycle distillation. Wherein VFP is a gas phase operation stage and LFP is a liquid phase operation stage; NVFP is the next gas phase operation cycle; CRS is public rectifying section, RDS is reactive rectifying section, CSS is public extracting section, R101 is reactive circulation rectifying tower reboiler, C101 is reactive circulation rectifying tower condenser, MT is tower plate with switch valve and gate chamber, MRT is reactive rectifying tower plate with switch valve and gate chamber and filled with solid catalyst.
Detailed Description
The application is further described in detail below with reference to the drawings by way of specific examples, which are not intended to limit the scope of the claims.
The application relates to a reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl carbonate, which comprises the following specific embodiments:
the reaction circulation refined fraction is a periodic gas phase and liquid phase operation stage, in the gas phase operation stage, the liquid phase is static on a tower plate, and the liquid phase performs mass transfer and heat transfer with the ascending gas phase and performs liquid phase esterification reaction; in the liquid phase operation stage, liquid on the tower plate enters a sluice chamber below the tower plate through opening a valve on the tower plate, and feeding of raw materials of dimethyl carbonate and ethanol, extraction of an azeotrope of a tower top product of dimethyl carbonate and methanol and extraction of a tower bottom product of methyl ethyl carbonate and diethyl carbonate are completed; and when the next gas phase operation period starts, the sluice chamber opens the liquid flow to the next layer of tower plate period to realize the mass transfer heat transfer and reaction process of the gas phase and the liquid phase.
The rectification column plate and the reaction rectification column plate adopted in the reaction circulation rectification column are realized by column plates provided with valves and a lower lock chamber, wherein the reaction rectification column plate is filled with solid catalyst.
Example 1
In the application, the feeding mole ratio of the dimethyl carbonate to the ethanol in the raw materials is set to be 1:1, the number of the column plates of a common rectifying section of the reaction and circulation rectifying is set to be 15, the number of the column plates of the reaction and rectifying section is set to be 20, the number of the column plates of the common stripping section is set to be 30, the operating pressure is 101.325Kpa, the gas-phase periodic operation time is 35s, the liquid-phase periodic operation time is 5s, the catalyst filled on the column plates of the reaction and rectifying section is alkali metal oxide MgO/HZSM-5, the filling amount of the solid catalyst on the column plates of the reaction and rectifying section is 30Kg, the periodic feeding amount of the solid catalyst is 0.4kmol/cycle, and the steam amount of the gas-phase operation stage is 1kmol/min.
After the raw materials of dimethyl carbonate and ethanol are subjected to the flow, 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 of the tower top is 0.27kmol/cycle, the periodic extraction amount of the tower bottom is 0.13kmol/cycle, compared with the traditional reactive distillation process, the energy consumption is reduced by 20.5%, and the single pass conversion rate of the dimethyl carbonate is improved by 43.4%.
Example 2
In the application, the feeding mole ratio of the dimethyl carbonate to the ethanol in the raw materials is set to be 1.2:1, the number of the trays of a common rectifying section of the reaction circulation rectifying is 15, the number of the trays of the reaction rectifying section is 25, the number of the trays of the common stripping section is 30, the operating pressure is 101.325Kpa, the gas-phase periodic operation time is 40s, the liquid-phase periodic operation time is 5s, the catalyst filled on the trays of the reaction rectifying section is alkali metal oxide MgO/HZSM-5, the filling amount of the solid catalyst on the trays of the reaction rectifying section is 35Kg, the cyclic feeding amount is 0.44kmol/cycle, and the steam amount in the gas-phase operation stage is 1.2kmol/min.
After the raw materials of dimethyl carbonate and ethanol are subjected to the flow, 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 rate of the tower top is 0.2912kmol/cycle, the periodic extraction rate of the tower bottom is 0.1488kmol/cycle, compared with the traditional reactive distillation process, the energy consumption is reduced by 22.4%, 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 methyl ethyl carbonate and diethyl carbonate is characterized in that a reaction circulation rectification tower consists of a public rectification section, a reaction rectification section and a public stripping section, wherein a tower plate of the reaction rectification section is filled with a catalyst, the reaction circulation rectification divides the reaction rectification process for producing the methyl ethyl carbonate and the diethyl carbonate 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 plate, steam flows from a reboiler to a condenser in the tower, and gas-liquid two phases undergo mass transfer and heat transfer on the tower plate and undergo transesterification chemical reaction in the tower plate liquid phase; during the liquid phase operation phase, the flowing vapor stops and the liquid moves between trays; the periodic operation of the gas phase and the liquid phase is realized by a tower internal member provided with a valve and a gate chamber positioned below the tray; the rules of periodic operation are: in the gas phase operation stage, a 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 from a tray to a gate chamber below, periodic feeding of raw materials of dimethyl carbonate and ethanol is completed, an azeotrope of the dimethyl carbonate and the methanol is extracted from the top of a reaction rectifying tower, and reaction products of methyl ethyl carbonate and diethyl carbonate are extracted from the bottom of the tower; at the beginning of another vapor flow cycle, the lock chamber opens the liquid flow to the tray below.
2. The reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl carbonate according to claim 1, wherein the operation mode of the reaction rectification process is divided into a gas phase operation stage and a liquid phase operation stage which are independent, and the operation time of the gas phase operation stage and the liquid phase operation stage, the gas phase period operation gas amount, the tray liquid holdup and the catalyst loading amount are adjusted according to the feeding flow rate.
3. The reaction circulation distillation process method for producing methyl ethyl carbonate and diethyl carbonate according to claim 1, wherein the reaction circulation distillation tower is divided into a public distillation section, a reaction distillation section and a public stripping section, dimethyl carbonate is periodically fed between the public distillation section and the reaction distillation section, and ethanol is periodically fed between the reaction distillation section and the public stripping section.
4. The process for the cyclic rectification of reaction for the production of ethylmethyl carbonate and diethylcarbonate according to claim 1, wherein the cyclic operation of the gas and liquid phases is carried out by means of column internals consisting of trays, on-off valves, and sluice chambers below the trays, the sluice chambers being provided in order to prevent mixing of the liquid phases of adjacent trays.
5. The process for producing ethylmethyl carbonate and diethyl carbonate according to claim 1, wherein the catalyst is filled on the column plate of the reaction rectifying section as a solid catalyst, the solid catalyst is an alkali metal oxide MgO/HZSM-5, and the strong acid ion exchange resins Lewatit K1221 and Nafion SAC-13 are modified K coated with polyethylene glycol 2 CO 3 。
6. The reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl carbonate according to claim 1, wherein the number of plates of a common rectification section of the reaction circulation rectification is 10-20, the number of plates of the reaction rectification section is 15-35, the number of plates of a common stripping section is 20-40, the molar ratio of dimethyl carbonate to ethanol in the feed is 2:1-0.5:1, and the operating pressure is 50-150 Kpa.
7. The reaction circulation rectification process method for producing methyl ethyl carbonate and diethyl carbonate according to claim 1, wherein the time ratio of gas phase to liquid phase operation is 3:1-12:1, and the ratio of methyl ethyl carbonate to diethyl carbonate is 3:1-6:1.
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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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| 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040044239A1 (en) * | 2000-07-24 | 2004-03-04 | Hironori Haga | Method for producing polycarbonate |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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