CN113735797A - Extractant for extractive distillation purification of dimethyl oxalate, preparation method thereof and purification method of dimethyl oxalate - Google Patents
Extractant for extractive distillation purification of dimethyl oxalate, preparation method thereof and purification method of dimethyl oxalate Download PDFInfo
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- CN113735797A CN113735797A CN202111183619.7A CN202111183619A CN113735797A CN 113735797 A CN113735797 A CN 113735797A CN 202111183619 A CN202111183619 A CN 202111183619A CN 113735797 A CN113735797 A CN 113735797A
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- dimethyl oxalate
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- methylpiperidine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/037—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
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Abstract
The invention relates to the technical field of dimethyl oxalate separation and purification, and particularly discloses an extracting agent for extracting, rectifying and purifying dimethyl oxalate, a preparation method thereof and a purification method of dimethyl oxalate. The extractant is N-decyl-N-methylpiperidine bromide, and the N-decyl-N-methylpiperidine bromide and the dimethyl oxalate crude product are simultaneously added into an extraction rectifying tower for rectification, so that a dimethyl oxalate product with the purity of more than 99.9 percent can be obtained. According to the invention, N-decyl-N-methylpiperidine bromide is used as an extracting agent to perform extractive distillation with the dimethyl oxalate crude product, so that the dimethyl oxalate in a tower kettle of a dimethyl oxalate rectifying tower in the process of preparing the ethylene glycol from coal can be fully recovered, the recovery rate of the dimethyl oxalate can reach more than 95%, the addition amount of the extracting agent is small, the extracting agent can be recycled by simple reduced pressure flash evaporation, the purity of the recovered extracting agent can reach more than 99.9%, the recovery rate of the extracting agent can reach more than 95%, and the market competitiveness of enterprises can be effectively improved.
Description
Technical Field
The invention relates to the technical field of dimethyl oxalate separation and purification, in particular to an extracting agent for extracting, rectifying and purifying dimethyl oxalate, a preparation method thereof and a purification method of dimethyl oxalate.
Background
Dimethyl oxalate of formula C4H6O4The product is an important intermediate product, can be hydrolyzed to prepare oxalic acid, can also be hydrogenated to prepare glycol, and has important application in the chemical industry. At present, the main production process of dimethyl oxalate is to prepare dimethyl oxalate by coupling reaction of carbon monoxide and methyl nitrite in the presence of palladium catalyst. In recent years, the development of the coal chemical industry is rapid, so that a process route for preparing dimethyl oxalate from CO and methyl nitrite is also widely concerned as an intermediate step for preparing ethylene glycol from coal.
In the existing process for preparing ethylene glycol from coal, after the synthesis reaction of dimethyl oxalate is finished, the dimethyl oxalate needs to be purified through the processes of an alcohol washing tower, an alcohol recovery tower and a rectifying tower. After the rectifying tower has distilled out the dimethyl oxalate product with higher purity, the tower bottom is mainly a mixture of the residual dimethyl oxalate and reaction byproducts, and the content of the dimethyl oxalate in the residue of the tower bottom is still higher. Moreover, because the boiling point of the reaction by-product is close to that of dimethyl oxalate, the reaction by-product cannot be removed by a conventional rectification method, so that the residue at the bottom of the tower is generally treated as hazardous waste at present, which not only causes the resource waste of dimethyl oxalate, but also increases the treatment cost of the hazardous waste, and causes the poor economic efficiency and environmental protection of the whole process. Therefore, it is necessary to develop a method for purifying dimethyl oxalate to realize the purification and recycling of dimethyl oxalate in the residue of the dimethyl oxalate rectifying tower.
Disclosure of Invention
In view of the above, the invention provides an extractant for extractive distillation and purification of dimethyl oxalate, a preparation method thereof and a purification method of dimethyl oxalate, and the invention selects specific ionic liquid and dimethyl oxalate to be added into a distillation tower for extractive distillation at the same time, thereby realizing the separation of reaction byproducts with high content and complex components in residues at the bottom of the distillation tower and dimethyl oxalate and obtaining a dimethyl oxalate product with the purity of more than 99.9 percent.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
in a first aspect, the invention provides an extractant for extractive distillation purification of dimethyl oxalate, which comprises N-decyl-N-methylpiperidine bromide, and the structural formula is as follows:
the dimethyl oxalate refers to a dimethyl oxalate crude product with the purity of more than 60%, in particular to a dimethyl oxalate crude product with the purity of 60-80% obtained from a tower kettle after purification and separation in a dimethyl oxalate rectifying tower in a coal-to-ethylene glycol process.
Compared with the prior art, the invention selects the N-decyl-N-methylpiperidine bromide as the extractant for extracting, rectifying and purifying the dimethyl oxalate, has good solubility to the dimethyl oxalate, can effectively change the relative volatility of the dimethyl oxalate and impurities with high content and complex components contained in the dimethyl oxalate, improves the separation effect of the dimethyl oxalate and various impurities, has good thermal stability and chemical stability and extremely low vapor pressure, can greatly reduce the problems of product purity reduction and the like caused by the volatilization of the extractant even in a high vacuum system, simultaneously avoids the environmental pollution problem caused by the volatilization of the extractant, and is beneficial to the recycling of the extractant.
In a second aspect, the invention also provides a preparation method of the extracting agent for extractive distillation and purification of dimethyl oxalate, which comprises the following steps:
uniformly mixing 1-methylpiperidine, bromodecane and ethyl acetate, reacting at 65-75 ℃ for 24-48 h, cooling, washing and drying to obtain the extractant.
Preferably, the molar ratio of the 1-methylpiperidine to the bromodecane to the ethyl acetate is 1:1 to 1.1.
The N-decyl-N-methylpiperidine bromide provided by the invention has the advantages of simple preparation process, mild reaction conditions and easily obtained raw materials, and is suitable for large-scale industrial production and application.
In a third aspect, the invention provides a method for purifying dimethyl oxalate, which comprises the following steps: adding the extractant for extracting, rectifying and purifying the dimethyl oxalate and the crude dimethyl oxalate into a rectifying tower for extracting and rectifying to obtain a dimethyl oxalate product.
Preferably, the method for purifying dimethyl oxalate specifically comprises the following steps:
introducing the preheated crude dimethyl oxalate into a rectifying tower from the middle-lower part of the rectifying tower, simultaneously introducing the preheated extractant into the rectifying tower from the upper part of the rectifying tower, performing extractive rectification to fractionate a dimethyl oxalate product from the top of the rectifying tower, introducing tower kettle materials into a solvent recovery tank for reduced pressure flash evaporation, extracting the extractant from the bottom of the solvent recovery tank, refluxing the extractant from the upper part of the rectifying tower through a pipeline into the rectifying tower for recycling, and obtaining a dimethyl oxalate byproduct from the top of the solvent recovery tank.
According to the method for purifying the dimethyl oxalate, the specific ionic liquid and the dimethyl oxalate crude product are selected for extractive distillation, the relative volatility of various byproducts with high content and complex components in the dimethyl oxalate crude product and the dimethyl oxalate is effectively changed, the separation effect of the dimethyl oxalate and impurities is effectively improved, the dimethyl oxalate product with the purity of more than 99.9 percent can be obtained at the top of the tower after the extractive distillation of the rectifying tower, and the recovery rate of the dimethyl oxalate can reach more than 95 percent. And the material flow at the bottom of the rectifying tower is subjected to reduced pressure flash evaporation through the solvent recovery tank, so that the ionic liquid extractant can be effectively recovered, the purity of the recovered ionic liquid extractant is more than 99.9%, the requirement of recycling can be met, the recovery rate of the ionic liquid extractant is more than 95%, and the method has high industrial popularization and application values.
Preferably, the mass flow ratio of the extracting agent to the crude dimethyl oxalate is 0.5-0.7: 1.
Preferably, the flow rate of the extracting agent is 50Kg/h-105Kg/h, and the flow rate of the crude dimethyl oxalate is 100Kg/h-150 Kg/h.
The optimized flow ratio of the extracting agent to the dimethyl oxalate crude product is favorable for improving the extraction efficiency on the premise of ensuring the recovery rate of the dimethyl oxalate.
Preferably, the top temperature of the rectifying tower is 85-95 ℃, the bottom temperature of the rectifying tower is 90-110 ℃, the tower pressure is 0.05-0.1 atm, and the reflux ratio is 0.5-3.0.
Preferably, the number of the trays of the rectifying tower is 20-30, the extracting agent is introduced from the 1 st-3 rd trays, and the crude dimethyl oxalate is introduced from the 10 th-17 th trays.
The number of the tower plates refers to the positions of the tower plates from top to bottom.
Preferably, the preheating temperature of the extracting agent and the preheating temperature of the crude dimethyl oxalate are both 60-80 ℃.
The optimized extraction and rectification conditions are favorable for improving the extraction efficiency, improving the separation effect of the dimethyl oxalate and impurities and improving the recovery rate and the purity of the dimethyl oxalate.
Preferably, the temperature of the decompression flash evaporation of the solvent recovery tank is 110-130 ℃, and the pressure is 0.1-0.3 atm.
Illustratively, the bottom of the rectifying tower is provided with a reboiler, preferably a kettle reboiler.
The N-decyl-N-methylpiperidine bromide ionic liquid extractant provided by the invention has good solubility on a dimethyl oxalate crude product, can effectively improve the separation effect of dimethyl oxalate and various impurities, is easy to separate from the impurities, is convenient to recycle, can effectively improve the rectification separation efficiency on the premise of ensuring the separation effect, can obtain a dimethyl oxalate product with the purity of more than 99.9% only by simple extractive rectification, realizes full recovery of the dimethyl oxalate in a rectifying tower kettle, has the recovery rate of more than 95%, and has the advantages of simple process, low extractant dosage, higher economic benefit and environmental protection benefit and wide application prospect.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In order to better illustrate the invention, the following examples are given by way of further illustration.
The crude dimethyl oxalate used in the following examples and comparative examples is the crude dimethyl oxalate with purity of 60-80% obtained from the bottom of a rectifying tower after purification and separation by a dimethyl oxalate rectifying tower in the process of preparing ethylene glycol from coal.
Example 1
The embodiment of the invention provides an extractant for extracting, rectifying and purifying dimethyl oxalate, which is N-decyl-N-methylpiperidine bromide and has the following structural formula:
the preparation method of the extracting agent comprises the following steps:
weighing 1-methylpiperidine and bromodecane according to a molar ratio of 1:1.01, adding the 1-methylpiperidine and the bromodecane into a three-neck flask provided with a reflux condenser tube and a mechanical stirring paddle, uniformly mixing and stirring, adding ethyl acetate with the same molar amount as the 1-methylpiperidine, reacting at the constant temperature of 70 ℃ in a water bath for 36 hours, stopping heating, cooling to room temperature, centrifugally washing the obtained light yellow crude product with ethyl acetate for 2-3 times, and then placing the product in a vacuum drying oven for drying at the temperature of 80 ℃ for 9 hours to obtain white solid powder, namely N-decyl-N-methylpiperidine bromide.
Example 2
The embodiment of the invention provides a method for purifying dimethyl oxalate, which comprises the following steps:
the extractive distillation tower has 20 theoretical plates, N-decyl-N-methylpiperidine bromide is preheated to 60 ℃, the N-decyl-N-methylpiperidine bromide is added from the 2 nd plate of the extractive distillation tower at the flow rate of 50kg/h, and the dimethyl oxalate crude product (with the content of 70%) preheated to 60 ℃ is added from the 11 th plate at the flow rate of 100kg/h, the tower top temperature of the extractive distillation tower is 85 ℃, the tower bottom temperature is 92 ℃, the tower pressure is 0.05atm, and the tower top reflux ratio is 0.5. The extraction amount at the top of the extractive distillation tower is 69kg/h, a dimethyl oxalate product with the content of 99.98 percent is obtained at the top of the extractive distillation tower, and a mixture of N-decyl-N-methyl piperidine bromide and a dimethyl oxalate byproduct is obtained at the bottom of the extractive distillation tower.
Introducing the materials in the bottom of the extraction and rectification tower into a solvent recovery tank for decompression and flash evaporation, wherein the flash evaporation temperature is 120 ℃, the flash evaporation pressure is 0.2atm, the N-decyl-N-methylpiperidine bromide with the mass fraction of 99.93% is obtained at the bottom of the solvent recovery tank, the extracted flow at the bottom of the solvent recovery tank is 49kg/h, and the extracted extractant flows back from the upper part of the rectification tower through a pipeline and enters the rectification tower.
Example 3
The embodiment of the invention provides a method for purifying dimethyl oxalate, which comprises the following steps:
the extractive distillation tower has 30 theoretical plates, N-decyl-N-methylpiperidine bromide is preheated to 70 ℃, added from the 3 rd plate of the extractive distillation tower at the flow rate of 60kg/h, and simultaneously, a crude dimethyl oxalate (with the content of 60%) preheated to 80 ℃ is added from the 17 th plate at the flow rate of 100kg/h, the tower top temperature of the extractive distillation tower is 91 ℃, the tower bottom temperature is 101 ℃, the tower pressure is 0.1atm, and the tower top reflux ratio is 1.0. The extraction amount at the top of the extraction and rectification tower is 59kg/h, a dimethyl oxalate product with the content of 99.94 percent is obtained at the top of the extraction and rectification tower, and a mixture of N-decyl-N-methyl piperidine bromide and a dimethyl oxalate byproduct is obtained at the bottom of the extraction and rectification tower.
Introducing the materials in the bottom of the extraction and rectification tower into a solvent recovery tank for decompression and flash evaporation, wherein the flash evaporation temperature is 110 ℃, the flash evaporation pressure is 0.1atm, the N-decyl-N-methylpiperidine bromide with the mass fraction of 99.91% is obtained at the bottom of the solvent recovery tank, the extracted flow at the bottom of the solvent recovery tank is 58kg/h, and the extracted extractant flows back into the rectification tower from the upper part of the rectification tower through a pipeline.
Example 4
The embodiment of the invention provides a method for purifying dimethyl oxalate, which comprises the following steps:
the extractive distillation tower has 25 theoretical plates, N-decyl-N-methylpiperidine bromide is preheated to 60 ℃, the N-decyl-N-methylpiperidine bromide is added from the 3 rd plate of the extractive distillation tower, the flow rate is 105kg/h, meanwhile, the dimethyl oxalate crude product (the content is 80%) preheated to 60 ℃ is added from the 15 th plate, the flow rate is 150kg/h, the tower top temperature of the extractive distillation tower is 95 ℃, the tower bottom temperature is 110 ℃, the tower pressure is 0.1atm, and the tower top reflux ratio is 3.0. The extraction amount at the top of the extractive distillation tower is 116kg/h, a dimethyl oxalate product with the content of 99.96 percent is obtained at the top of the extractive distillation tower, and a mixture of N-decyl-N-methyl piperidine bromide and a dimethyl oxalate byproduct is obtained at the bottom of the extractive distillation tower.
Introducing the materials at the bottom of the extraction and rectification tower into a solvent recovery tank for decompression and flash evaporation, wherein the flash evaporation temperature is 130 ℃, the flash evaporation pressure is 0.3atm, the N-decyl-N-methylpiperidine bromide with the mass fraction of 99.94% is obtained at the bottom of the solvent recovery tank, the extracted flow at the bottom of the solvent recovery tank is 102kg/h, and the extracted extractant flows back from the upper part of the rectification tower through a pipeline and enters the rectification tower.
When the raw material ratio, the reaction temperature and the reaction time in the process of preparing the N-decyl-N-methylpiperidine bromide in the above example 1 are replaced by other parameters defined by the present invention, the prepared N-decyl-N-methylpiperidine bromide ionic liquid can achieve the technical effects basically equivalent to those of the corresponding examples when applied to the examples 2 to 4.
Comparative example 1
This comparative example provides a process for the purification of dimethyl oxalate, which comprises exactly the same purification steps as in example 2, except that the N-decyl-N-methylpiperidine bromide salt is replaced with 1-ethyl-3-methylimidazolidinium salt ionic liquid, and the remaining process steps and parameters are the same as in example 2, and thus, the details thereof are omitted.
The extraction amount at the top of the extraction and rectification tower is 67kg/h, and dimethyl oxalate with the content of 91.85 percent is obtained at the top of the tower.
In conclusion, the embodiment of the invention adopts the specific N-decyl-N-methylpiperidine bromine salt as the extracting agent to perform extractive distillation with the dimethyl oxalate crude product, can realize the full recovery of the dimethyl oxalate in the tower kettle of the dimethyl oxalate rectifying tower in the coal glycol preparation process, and obtain the dimethyl oxalate product with the purity of more than 99.9%, wherein the recovery rate of the dimethyl oxalate can reach more than 95%, the addition amount of the extracting agent is small, the extracting agent can be recycled by simple reduced pressure flash evaporation, the purity of the recovered extracting agent can reach more than 99.9%, and the recovery rate of the extracting agent can reach more than 95%, so that the market competitiveness of enterprises can be effectively improved, and the application prospect is wide.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents or improvements made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (10)
1. An extractant for extracting, rectifying and purifying dimethyl oxalate is characterized in that the extractant comprises N-decyl-N-methylpiperidine bromide.
2. A method for preparing the extractant of claim 1, comprising the steps of:
uniformly mixing 1-methylpiperidine, bromodecane and ethyl acetate, reacting at 65-75 ℃ for 24-48 h, cooling, washing and drying to obtain the extractant.
3. The method for preparing the extractant according to claim 2, wherein the molar ratio of the 1-methylpiperidine, the bromodecane, and the ethyl acetate is 1:1 to 1.1.
4. A method for purifying dimethyl oxalate is characterized in that the extractant in claim 1 and a crude product of dimethyl oxalate are added into a rectifying tower for extractive rectification to obtain a dimethyl oxalate product.
5. The method for purifying dimethyl oxalate as claimed in claim 4, comprising the steps of:
introducing the preheated crude dimethyl oxalate into a rectifying tower from the middle lower part of the rectifying tower, simultaneously introducing the preheated extractant into the rectifying tower from the upper part of the rectifying tower, performing extractive rectification to fractionate a dimethyl oxalate product from the top of the tower, introducing tower kettle materials into a solvent recovery tank for reduced pressure flash evaporation, and collecting the extractant from the bottom of the solvent recovery tank.
6. The method of claim 5, wherein the mass flow ratio of the extractant to the crude dimethyl oxalate is 0.5-0.7: 1.
7. The method for purifying dimethyl oxalate as claimed in claim 6, wherein the flow rate of the extractant is 50Kg/h to 105Kg/h, and the flow rate of the crude dimethyl oxalate is 100Kg/h to 150 Kg/h.
8. The method for purifying dimethyl oxalate recited in claim 5, wherein the top temperature of the rectifying tower is 85 ℃ to 95 ℃, the bottom temperature of the rectifying tower is 90 ℃ to 110 ℃, the tower pressure is 0.05atm to 0.1atm, and the reflux ratio is 0.5 to 3.0; and/or
The temperature of the decompression flash evaporation of the solvent recovery tank is 110-130 ℃, and the pressure is 0.1-0.3 atm.
9. The method for purifying dimethyl oxalate as claimed in claim 5, wherein the number of the plates of the rectifying tower is 20 to 30, the extractant is introduced from the 1 st to 3 rd plates, and the crude dimethyl oxalate is introduced from the 10 th to 17 th plates.
10. The method of claim 5, wherein the pre-heating temperature of the extractant and the crude dimethyl oxalate are both 60 ℃ to 80 ℃.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62294603A (en) * | 1986-06-13 | 1987-12-22 | Ss Pharmaceut Co Ltd | Plant growth regulator |
| CN107987104A (en) * | 2017-12-13 | 2018-05-04 | 浙江省农业科学院 | Gyphosate herbicice ionic liquid and its preparation and application |
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- 2021-10-11 CN CN202111183619.7A patent/CN113735797B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62294603A (en) * | 1986-06-13 | 1987-12-22 | Ss Pharmaceut Co Ltd | Plant growth regulator |
| CN107987104A (en) * | 2017-12-13 | 2018-05-04 | 浙江省农业科学院 | Gyphosate herbicice ionic liquid and its preparation and application |
Non-Patent Citations (6)
| Title |
|---|
| ANACKER,E.W.等: "Dependence of micelle aggregation number on polar head structure.II.Light scattering by aqueous solutions of decyldiethylammonium bromide and related heterocyclic surfactants" * |
| BARTOSZ MARKIEWICZ等: "Ionic liquids with a theophyllinate anion" * |
| JACOBS等: "The Role of polar head structure in dye solubilization by cationic surfactants" * |
| KATHLEEN LAVA等: "Piperidinium, Piperazinium and Morpholinium Ionic Liquid Crystals" * |
| LACKO, I.等: "Organic ammonium salts. I. The synthesis and antimicrobial effectiveness of 1,1-dialkylpiperidinium bromides" * |
| MARCUS K. DYMOND等: "Cationic Type I Amphiphiles As Modulators of Membrane Curvature Elastic Stress in Vivo" * |
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