CN113999198A - Method for synthesizing ethylene carbonate - Google Patents
Method for synthesizing ethylene carbonate Download PDFInfo
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- CN113999198A CN113999198A CN202111500880.5A CN202111500880A CN113999198A CN 113999198 A CN113999198 A CN 113999198A CN 202111500880 A CN202111500880 A CN 202111500880A CN 113999198 A CN113999198 A CN 113999198A
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- ethylene carbonate
- solution
- stirring
- imidazole
- ethylene glycol
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- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000002194 synthesizing effect Effects 0.000 title claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 90
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000003756 stirring Methods 0.000 claims abstract description 20
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 238000001816 cooling Methods 0.000 claims abstract description 14
- 238000001914 filtration Methods 0.000 claims abstract description 12
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 239000000843 powder Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- 239000012295 chemical reaction liquid Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 230000000717 retained effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000003828 vacuum filtration Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 4
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 238000004821 distillation Methods 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000010865 sewage Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 229960001625 furazolidone Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical class [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
- C07D317/38—Ethylene carbonate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of ethylene carbonate, which relates to the chemical synthesis technology and aims to solve the problem that when ethylene carbonate is prepared from ethylene glycol and N' N-carbonyl diimidazole, the ethylene glycol used in excess and imidazole dissolved in the ethylene glycol are wasted and are discharged randomly to cause safety accidents, and the technical scheme is characterized in that: step 1: filtering the reaction solution; step 2: adding imidazole and stirring; and step 3: filtering to obtain filtrate; and 4, step 4: adding hexamethyldisilazane, stirring and heating for reaction; and 5: heating and refluxing; step 6: cooling; and 7: carrying out reduced pressure distillation; and 8: stirring triphosgene and dichloromethane; and step 9: cooling; step 10: dropping the distillate; step 11: adding ethylene glycol and stirring; step 12: and (5) drying and rectifying. The method can fully recycle imidazole and ethylene glycol generated in the preparation process of the ethylene carbonate, and can be used for preparing the ethylene carbonate again, and the problem of environmental damage caused by random sewage discharge is avoided.
Description
Technical Field
The invention relates to a chemical synthesis technology, in particular to a synthesis method of ethylene carbonate.
Background
Ethylene Carbonate (EC) is an organic solvent with excellent performance and can dissolve various polymers; in addition, the product can be used as an organic intermediate to replace ethylene oxide for a dioxygenation reaction and is a main raw material for producing dimethyl carbonate by a transesterification method; can also be used as raw materials for synthesizing furazolidone, water glass series sizing agent, fiber finishing agent and the like; in addition, the electrolyte is also applied to lithium battery electrolytes. Ethylene carbonate is also useful as a reactive intermediate in the production of lubricating oils and greases.
At present, various raw materials and related equipment are mostly needed for the preparation and synthesis method of the ethylene carbonate, so that the preparation and synthesis cost of the ethylene carbonate is higher, the purity of the prepared and synthesized ethylene carbonate finished product is lower, the economic benefit is correspondingly lower, and the method is not worthy of popularization.
Therefore, the method for synthesizing the ethylene carbonate with the publication number of CN110981847A provides a novel method for synthesizing the ethylene carbonate, and the main technology is as follows: s1, raw material and related equipment preparation: preparing ethylene glycol, N' N-carbonyl diimidazole and a drying agent according to proper components and proportions, and preparing a reaction kettle, filtering equipment, rectifying equipment and other related equipment; s2, raw material and related equipment inspection: materials such as ethylene glycol, N' N-carbonyl diimidazole, drying agent and the like and related equipment which are required to be used are checked, and if the materials with quality not meeting the standard or raw materials with no use effect and the related equipment with invalid functions exist, the materials need to be replaced; s3, preliminary mixing preparation: in an anhydrous atmosphere obtained under the protection of nitrogen, adding prepared ethylene glycol and N' N-carbonyl diimidazole into a reaction kettle according to a certain proportion, adding a drying agent, stirring for 3-10 h, and adjusting the temperature in the reaction kettle to 80-140 ℃; s3, preliminary mixing preparation: in an anhydrous atmosphere obtained under the protection of nitrogen, adding prepared ethylene glycol and N' N-carbonyl diimidazole into a reaction kettle according to a certain proportion, adding a drying agent, stirring for 3-10 h, and adjusting the temperature in the reaction kettle to 80-140 ℃; s5, filtering the materials: filtering the material by prepared filtering equipment to remove part of impurities in the material; s6, rectifying and purifying materials: the rectification and extraction work of the filtered material is completed by the normal pressure rectification technology, and the ethylene carbonate with the purity of 99.9 percent can be obtained.
A large amount of imidazole is generated and dissolved in ethylene glycol in the synthesis process by the method, the ethylene glycol is used excessively, the excessive ethylene glycol and the imidazole dissolved in the ethylene glycol are wasted by rectification and extraction, and the imidazole has certain toxicity, is easy to dissolve in water, and can cause personal safety problems after being discharged without treatment.
Therefore, a new solution is needed to solve this problem.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a method for synthesizing ethylene carbonate, which can fully utilize imidazole generated in the synthesis process of ethylene carbonate, improve the resource utilization rate, improve the purity of ethylene carbonate products and avoid the problem of environmental safety caused by random discharge of solution with imidazole.
The technical purpose of the invention is realized by the following technical scheme: a method for synthesizing ethylene carbonate comprises
Step 1: filtering reaction liquid of ethylene glycol and N' N-carbonyl diimidazole to obtain a solution I;
step 2: adding imidazole powder into the solution I, and stirring until the imidazole powder is retained in the solution I;
and step 3: filtering imidazole powder to obtain filtrate;
and 4, step 4: adding hexamethyldisilazane into the filtrate, stirring, adding a small amount of catalyst, heating, stopping stirring after gas stops appearing, and keeping the temperature to obtain a reaction solution;
and 5: heating the reaction solution, and keeping refluxing for 5h at 105 ℃ to obtain an orange solution;
step 6: cooling the orange solution to below 50 ℃;
and 7: distilling the orange solution under reduced pressure, and collecting excessive hexamethyldisilazane, ethylene glycol and 75-80 deg.C/1.03 kPa fraction;
and 8: triphosgene and dichloromethane are stirred until being dissolved to obtain a solution II;
and step 9: cooling the solution II to below 20 ℃;
step 10: maintaining the temperature below 20 deg.C, adding dropwise the distillate under nitrogen protection, and maintaining for 20-40 min;
step 11: adding the distilled glycol and stirring;
step 12: and drying and rectifying the substances in the step fourteen to obtain the high-purity ethylene carbonate.
By adopting the technical scheme, the method can further process the imidazole and the ethylene glycol left in the reaction liquid after the synthesis of the ethylene carbonate is completed for the first time, so that the residual reaction liquid can be reused to generate the ethylene carbonate, the purity and the yield of the ethylene carbonate are improved, the discharge of imidazole-containing wastewater can be reduced, and the adverse effect of the imidazole on the environment and a water source is avoided.
The invention is further configured to: the first solution in step 2 is maintained at 20-40 deg.C.
By adopting the technical scheme, the solubility of the imidazole in the glycol is optimal between 20 and 40 ℃, so that the imidazole can dissolve a large amount of imidazole.
The invention is further configured to: further comprising a step 4.5, between step 4 and step 5, of absorbing the gas produced in step 4 by means of lye.
Through adopting above-mentioned technical scheme, come to absorb gas through alkali lye to avoid gas to discharge at will, avoid gas to cause the harm to human body.
The invention is further configured to: the mass ratio of triphosgene to dichloromethane is 5-6: 100.
by adopting the technical scheme, the mass ratio of the triphosgene to the dichloromethane is 5-6: when the ratio is between 100, the ratio of the triphosgene and the dichloromethane is optimal, and the triphosgene and the dichloromethane can be fully utilized.
The invention is further configured to: further comprises a step 10.5 which is between the step 10 and the step 11, and the distillate is dripped and then stands for cooling and crystallizing.
The invention is further configured to: the cooling regime in step 10.5 is an ice bath.
The invention is further configured to: also comprises a step 10.5.5 which is between the step 10.5 and the step 11, and after the crystallization is completed, the vacuum filtration and the vacuum drying are carried out.
Through adopting above-mentioned technical scheme, through suction filtration vacuum drying, can dry the material, remove moisture, improve purity.
In conclusion, the invention has the following beneficial effects:
by the method, after the synthesis of the primary ethylene carbonate is completed, imidazole and ethylene glycol left in the reaction liquid are further processed, so that redundant reaction liquid can be reused to generate the ethylene carbonate, the purity and the yield of the ethylene carbonate are improved, the discharge of imidazole-containing wastewater can be reduced, and adverse effects of imidazole on environment and water sources are avoided.
Detailed Description
The present invention will be described in detail with reference to examples.
Example (b):
a method for synthesizing ethylene carbonate comprises
Step 1, filtering reaction liquid of ethylene glycol and N' N-carbonyl diimidazole to obtain a solution I, and removing redundant impurities.
And 2, maintaining the first solution at the temperature of 20-40 ℃, adding imidazole powder into the first solution, stirring until the imidazole powder is retained in the first solution, and ensuring that the imidazole is fully dissolved in the ethylene glycol in the first solution and the saturation of the first solution.
And 3, filtering the imidazole powder to obtain filtrate, and removing redundant imidazole powder to avoid the imidazole powder from being wasted.
And 4, adding hexamethyldisilazane into the filtrate, stirring, adding a small amount of catalyst, heating, stopping stirring after gas stops appearing, keeping the temperature to obtain a reaction solution, reacting in the process, and generating N-trimethylsilylimidazole and ammonia gas from imidazole and hexamethyldisilazane under the action of the catalyst and the heating.
And 4.5, absorbing the gas generated in the step 4 by alkali liquor, for example, reacting sodium hydroxide with ammonia gas for absorption, so as to avoid the ammonia gas from leaking at will, on one hand, avoiding people from absorbing odor, and on the other hand, recovering the ammonia gas which belongs to toxic and harmful gas, so that the health and safety of people can be ensured.
And step 5, heating the reaction solution, and keeping refluxing for 5 hours at 105 ℃ to complete the condensation reaction to obtain an orange solution.
And 6, cooling the orange solution to below 50 ℃.
And 7, carrying out reduced pressure distillation on the orange solution, collecting excessive hexamethyldisilazane, ethylene glycol and 75-80 ℃/1.03kPa of fraction, wherein the fraction is N-trimethylsilylimidazole, the yield is 92%, and the content is 98% through liquid phase detection.
And step 8, stirring and dissolving the triphosgene and the dichloromethane, wherein the mass ratio of the triphosgene to the dichloromethane is 5.94: and (100) stirring to be completely dissolved to obtain a solution II, wherein in the process, N-trimethylsilylimidazole and triphosgene generate trimethylchlorosilane and ethylene carbonate under the action of dichloromethane and at the temperature of 20 ℃.
And 9, cooling the solution to below 20 ℃ in an ice bath mode.
And step 10, maintaining the temperature below 20 ℃, dropwise adding the fraction under the protection of nitrogen, and maintaining for 20-40min, optimally 30 min.
Step 10.5, dropwise adding the distillate, standing, cooling and crystallizing, wherein the cooling mode is ice bath;
and step 10.5.5, after the crystallization is completed, carrying out suction filtration and vacuum drying to obtain a white powdery solid, wherein the yield is 98.3%, and the content is 98.5% through liquid phase detection.
And 11, adding the distilled glycol and stirring.
And 12, drying and rectifying the substances in the fourteenth step to obtain the high-purity ethylene carbonate.
The above description is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above embodiments, and all technical solutions belonging to the idea of the present invention belong to the protection scope of the present invention. It should be noted that modifications and embellishments within the scope of the invention may occur to those skilled in the art without departing from the principle of the invention, and are considered to be within the scope of the invention.
Claims (7)
1. A method for synthesizing ethylene carbonate is characterized in that: comprises that
Step 1: filtering reaction liquid of ethylene glycol and N' N-carbonyl diimidazole to obtain a solution I;
step 2: adding imidazole powder into the solution I, and stirring until the imidazole powder is retained in the solution I;
and step 3: filtering imidazole powder to obtain filtrate;
and 4, step 4: adding hexamethyldisilazane into the filtrate, stirring, adding a small amount of catalyst, heating, stopping stirring after gas stops appearing, and keeping the temperature to obtain a reaction solution;
and 5: heating the reaction solution, and keeping refluxing for 5h at 105 ℃ to obtain an orange solution;
step 6: cooling the orange solution to below 50 ℃;
and 7: distilling the orange solution under reduced pressure, and collecting excessive hexamethyldisilazane, ethylene glycol and 75-80 deg.C/1.03 kPa fraction;
and 8: triphosgene and dichloromethane are stirred until being dissolved to obtain a solution II;
and step 9: cooling the solution II to below 20 ℃;
step 10: maintaining the temperature below 20 deg.C, adding dropwise the distillate under nitrogen protection, and maintaining for 20-40 min;
step 11: adding the distilled glycol and stirring;
step 12: and drying and rectifying the substances in the step fourteen to obtain the high-purity ethylene carbonate.
2. The method for synthesizing ethylene carbonate according to claim 1, wherein: the first solution in step 2 is maintained at 20-40 deg.C.
3. The method for synthesizing ethylene carbonate according to claim 1, wherein: further comprising a step 4.5, between step 4 and step 5, of absorbing the gas produced in step 4 by means of lye.
4. The method for synthesizing ethylene carbonate according to claim 1, wherein: the mass ratio of triphosgene to dichloromethane is 5-6: 100.
5. the method for synthesizing ethylene carbonate according to claim 1, wherein: further comprises a step 10.5 which is between the step 10 and the step 11, and the distillate is dripped and then stands for cooling and crystallizing.
6. The method for synthesizing ethylene carbonate according to claim 5, wherein: the cooling regime in step 10.5 is an ice bath.
7. The method for synthesizing ethylene carbonate according to claim 6, wherein: also comprises a step 10.5.5 which is between the step 10.5 and the step 11, and after the crystallization is completed, the vacuum filtration and the vacuum drying are carried out.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111500880.5A CN113999198A (en) | 2021-12-09 | 2021-12-09 | Method for synthesizing ethylene carbonate |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111500880.5A CN113999198A (en) | 2021-12-09 | 2021-12-09 | Method for synthesizing ethylene carbonate |
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| CN113999198A true CN113999198A (en) | 2022-02-01 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114605372A (en) * | 2022-03-29 | 2022-06-10 | 山东富海石化工程有限公司 | Preparation process for energy-saving co-production of carbonic ester |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232430A (en) * | 2018-08-16 | 2019-01-18 | 浙江胡涂硅科技有限公司 | A kind of preparation method of carbonyl dimidazoles |
| CN110981847A (en) * | 2019-12-20 | 2020-04-10 | 泰兴华盛精细化工有限公司 | Method for synthesizing ethylene carbonate |
-
2021
- 2021-12-09 CN CN202111500880.5A patent/CN113999198A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232430A (en) * | 2018-08-16 | 2019-01-18 | 浙江胡涂硅科技有限公司 | A kind of preparation method of carbonyl dimidazoles |
| CN110981847A (en) * | 2019-12-20 | 2020-04-10 | 泰兴华盛精细化工有限公司 | Method for synthesizing ethylene carbonate |
Non-Patent Citations (1)
| Title |
|---|
| 邱方利: "羰基二咪唑合成工艺的研究", 应用化工 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114605372A (en) * | 2022-03-29 | 2022-06-10 | 山东富海石化工程有限公司 | Preparation process for energy-saving co-production of carbonic ester |
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Application publication date: 20220201 |