CN111056975A - Method for removing acetone from acetonitrile product - Google Patents
Method for removing acetone from acetonitrile product Download PDFInfo
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- CN111056975A CN111056975A CN201911203010.4A CN201911203010A CN111056975A CN 111056975 A CN111056975 A CN 111056975A CN 201911203010 A CN201911203010 A CN 201911203010A CN 111056975 A CN111056975 A CN 111056975A
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- Prior art keywords
- acetonitrile
- acetone
- dinitrophenylhydrazine
- solution
- removing acetone
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title claims abstract description 233
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 124
- 238000000034 method Methods 0.000 title claims abstract description 36
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000010992 reflux Methods 0.000 claims abstract description 25
- 238000010438 heat treatment Methods 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 13
- 238000005303 weighing Methods 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 5
- 230000003321 amplification Effects 0.000 abstract description 3
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000498 cooling water Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JHISIGSCVMVTET-UHFFFAOYSA-N [P].CN Chemical compound [P].CN JHISIGSCVMVTET-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000003713 acetylimino group Chemical group [H]C([H])([H])C(=O)N=[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of chemical industry, and particularly relates to a method for removing acetone from acetonitrile, which comprises the following steps: (1) the method comprises the steps of taking 98-99% acetonitrile as a raw material, taking about 40-50ppm acetone and 1-8% mass concentration 2, 4-dinitrophenylhydrazine solution, weighing a certain amount of 2, 4-dinitrophenylhydrazine and acetonitrile according to the molar ratio of the acetone to the 2, 4-dinitrophenylhydrazine of 1:1-1:2, mixing, stirring, heating and starting reflux. (2) Controlling the reflux time for 10min-2h to remove all acetone in the obtained acetonitrile product. The process can completely remove trace acetone in the acetonitrile. The process is simple to operate, is suitable for industrial amplification and has practical value.
Description
Technical Field
The invention belongs to the field of chemical industry, and particularly relates to a method for removing acetone from acetonitrile products.
Background
Acetonitrile, english name: acetonitrile, alias: methyl cyanide, molecular formula and molecular weight: C2H3N ═ 41.05; physical and chemical properties: appearance: colorless liquid with pungent odor; melting Point (. degree. C.): -45.7; boiling point (. degree.C., atmospheric pressure): 81-82; flash point (. degree. C.): 6; solubility: is miscible with water and soluble in most organic solvents such as alcohol.
Acetonitrile is a solvent with wide application and excellent performance, and can be mixed and dissolved with water, various inorganic substances and organic substances. Can be used as solvent for synthetic fiber, or used as solvent for extracting fat from animal and vegetable oil in oil industry, or used as excellent reaction solvent, and has special dissolution property and phase transferability, and is favorable for improving reaction yield. The carbon-nitrogen triple bond of acetonitrile is easy to generate nitrile addition reaction, can be used in the field of fine chemical industry, and is an important intermediate for the synthetic reaction of medicines and pesticides. The pure acetonitrile can be used as an organic modifier and a solvent of thin-layer chromatography, paper chromatography, spectrum, liquid chromatography and polarography, in particular to be used as a mobile phase of high performance liquid chromatography, and the analysis precision can reach more than ppb level.
The prior art introduces a method for removing impurities such as hydrocyanic acid, acrylonitrile and the like in ① acetonitrile, the method comprises the steps of adding a strong oxidant for reaction, rectifying and filtering to obtain high-purity acetonitrile, the method for removing water in ② acetonitrile comprises the steps of mixing the water-containing acetonitrile with alkali, separating acetonitrile and a water phase, removing the water phase, distilling the obtained acetonitrile to obtain purified acetonitrile, passing the obtained purified acetonitrile through cation exchange resin to obtain the high-purity acetonitrile, ③ adding a strong acid strong base salt and a hydrocarbon solvent into the waste acetonitrile, oscillating, standing, layering, adding potassium permanganate peroxide, heating, distilling, and finally introducing an adsorbent filled with activated carbon for adsorption to obtain the high-purity acetonitrile.
The documents and patents that employ the above methods are as follows:
1. a method for preparing full brilliant, yellow straight and plum blossom red plum, a mass spectrum level acetonitrile and a device thereof,
[P].CN:102432498A.2011-10-28
2. high-purity acetonitrile
[P].CN:101171233A.2008-4-30
3. Purification method of high-purity organic solvent acetonitrile from Shanghai Shaoxing high-purity solvent Co
[P].CN:201310753989.9.2015-7-1
These documents and patents employ different methods for removing impurities from acetonitrile, but none of the prior art provides a method for removing acetone from acetonitrile.
Disclosure of Invention
The invention aims to provide a method for effectively removing acetone from acetonitrile, which comprises the steps of taking acetonitrile as a raw material, weighing a 2, 4-dinitrophenylhydrazine solution into the acetonitrile according to a molar ratio, starting stirring and heating, and simultaneously carrying out reflux, wherein the obtained acetonitrile product does not contain acetone impurities. The method can completely remove acetone, does not influence the acetonitrile content, has simple process, is suitable for industrial amplification and has great practical value.
The invention adopts the following technical scheme:
a method for removing acetone from acetonitrile products comprises the following steps:
(1) weighing 2, 4-dinitrophenylhydrazine and acetonitrile, and mixing, wherein the acetonitrile contains an organic component of 98-99% and contains 40-50ppm of acetone; the 2, 4-dinitrophenylhydrazine is a 2, 4-dinitrophenylhydrazine solution with the mass concentration of 1% -8%, the materials are fed according to the molar ratio of acetone to 2, 4-dinitrophenylhydrazine of 1:1-1:2, stirred and heated, and the reflux is started;
(2) controlling the reflux time for 10min-2h, and completely removing the acetone in the obtained acetonitrile product.
Further, the reflux time in the step (2) is controlled to be 30 min-60 min.
Further, the 2, 4-dinitrophenylhydrazine solution is acetonitrile solution of 2, 4-dinitrophenylhydrazine.
Further, the rotation speed of the stirring in the step (1) is 100-300 rpm/min.
Further, the heating rate in the step (1) is 5-10 ℃/h.
Further, the mass concentration range of the 2, 4-dinitrophenylhydrazine is 2-6%.
Further, the molar ratio of the acetone to the 2, 4-dinitrophenylhydrazine is 1:1 to 1.15.
Further, the reflux time is 10min-60 min.
In the method for removing acetone from acetonitrile, acetonitrile is firstly added into a reaction kettle, a 2, 4-dinitrophenylhydrazine solution is added according to a proportion, electric stirring is started, the stirring speed is set to be 100-300rpm/min, electric heating of the reaction kettle is started, the temperature rise speed is set to be 5-10 ℃, the solution starts to flow back, the reflux time is controlled to be 10min-2h, and all the acetone in the obtained acetonitrile is removed.
The acetonitrile contains 98-99% of acetonitrile organic components, and contains 40-50ppm of acetone, wherein the acetone is a byproduct in acetonitrile production.
In the invention, acetone and 2, 4-dinitrophenylhydrazine are used for reacting to generate 2, 4-dinitrophenylhydrazone, so that the boiling point difference between the acetone and acetonitrile is improved, and the acetone can be separated by distillation subsequently.
The invention has the beneficial effects that:
the process can completely remove trace acetone in the acetonitrile; the process is simple to operate, is suitable for industrial amplification and has practical value.
Detailed Description
The following provides a specific example of the method for removing acetone from acetonitrile product.
Comparative example 1: a method for removing acetone from acetonitrile products comprises the following steps:
acetonitrile with the content of organic components of 98-99 percent is used as a raw material, acetone is 45ppm, and a 2, 4-dinitrophenylhydrazine solution with the mass concentration of 1 percent is prepared at room temperature, wherein the weight ratio of acetone: weighing a certain amount of 2, 4-dinitrophenylhydrazine solution into acetonitrile, starting stirring and heating, opening cooling water of a return pipe for refluxing, and controlling heating to keep the solution refluxing for 1h, wherein the acetone content is 20 ppm.
Example 2: a method for removing acetone from acetonitrile products comprises the following steps:
acetonitrile with the content of organic components of 98-99 percent is used as a raw material, 40ppm of acetone is used for preparing a 2, 4-dinitrophenylhydrazine solution with the mass concentration of 4 percent at room temperature, and the reaction is carried out according to the molar ratio of acetone: weighing a certain amount of 2, 4-dinitrophenylhydrazine solution into acetonitrile, starting stirring and heating, opening cooling water of a return pipe for refluxing, controlling heating to keep the solution for refluxing for 30min, and detecting no acetone in the product.
Example 3: a method for removing acetone from acetonitrile products comprises the following steps:
acetonitrile with the content of organic components of 98-99 percent is used as a raw material, acetone is 45ppm, and a 2, 4-dinitrophenylhydrazine solution with the mass concentration of 6 percent is prepared at room temperature, wherein the weight ratio of acetone: weighing a certain amount of 2, 4-dinitrophenylhydrazine solution into acetonitrile, starting stirring and heating, opening cooling water of a return pipe for refluxing, controlling heating to keep the solution for refluxing for 45min, and detecting no acetone in the product.
Example 4: a method for removing acetone from acetonitrile products comprises the following steps:
acetonitrile with the content of organic components of 98-99 percent is used as a raw material, 50ppm of acetone is used for preparing a 2, 4-dinitrophenylhydrazine solution with the mass concentration of 4 percent at room temperature, and the reaction is carried out according to the molar ratio of acetone: weighing a certain amount of 2, 4-dinitrophenylhydrazine solution into acetonitrile, starting stirring and heating, opening cooling water of a return pipe for refluxing, controlling heating to keep the solution for refluxing for 60min, and detecting no acetone in the product.
Example 5A method for removing acetone from the product acetonitrile:
acetonitrile with the content of organic components of 98-99 percent is used as a raw material, acetone is 48ppm, and a 2, 4-dinitrophenylhydrazine solution with the mass concentration of 4 percent is prepared at room temperature, wherein the weight ratio of acetone: weighing a certain amount of 2, 4-dinitrophenylhydrazine solution into acetonitrile, starting stirring and heating, opening cooling water of a return pipe for refluxing, controlling heating to keep the solution for refluxing for 45min, and detecting no acetone in the product.
Example 6: industrial scale-up
Putting 3000L (initial acetone 40-50ppm) of acetonitrile which is a raw material and has the organic component content of 98-99% into a 5000L stirring reaction kettle, starting stirring, and adding acetone: adding 10L of 2, 4-dinitrophenylhydrazine solution with the mass concentration of 5% at room temperature, starting heating, opening a cooling water reflux pipe to reflux, controlling the heating to keep the solution to reflux for 0.5h, and detecting no acetone in the product.
The invention analyzes the content of acetone in acetonitrile by gas chromatography, and the detection conditions are as follows: the FID detector and capillary column are adopted, the temperature is raised to 200 ℃ at the speed of 10 ℃/min, the temperature is kept for 20min, N2 is used as carrier gas, and the sample injection amount is 0.2-0.4 mu L.
The present invention has been disclosed in terms of the preferred embodiment, but it is not intended to be limited to the embodiment, and all technical solutions obtained by substituting or converting the equivalent embodiments fall within the scope of the present invention.
Claims (8)
1. A method for removing acetone from acetonitrile products is characterized by comprising the following steps:
(1) weighing 2, 4-dinitrophenylhydrazine and acetonitrile, and mixing, wherein the acetonitrile contains an organic component of 98-99% and contains 40-50ppm of acetone; the 2, 4-dinitrophenylhydrazine is a 2, 4-dinitrophenylhydrazine solution with the mass concentration of 1% -8%, the materials are fed according to the molar ratio of acetone to 2, 4-dinitrophenylhydrazine of 1:1-1:2, stirred and heated, and the reflux is started;
(2) controlling the reflux time for 10min-2h, and completely removing the acetone in the obtained acetonitrile product.
2. The method for removing acetone from acetonitrile as a product according to claim 1, wherein the reflux time in the step (2) is controlled to be 30-60 min.
3. The method for removing acetone from acetonitrile as a product according to claim 1, wherein the solution of 2, 4-dinitrophenylhydrazine is a solution of 2, 4-dinitrophenylhydrazine in acetonitrile.
4. The method for removing acetone from acetonitrile as claimed in claim 1, wherein the stirring speed in step (1) is 100-300 rpm/min.
5. The method for removing acetone from acetonitrile as a product according to claim 1, wherein the heating rate in step (1) is 5-10 ℃/h.
6. The method for removing acetone from acetonitrile as a product according to claim 1, wherein the mass concentration of the 2, 4-dinitrophenylhydrazine is within a range of 2-6%.
7. The method for removing acetone from acetonitrile as a product according to claim 1, wherein the molar ratio of acetone to 2, 4-dinitrophenylhydrazine is 1: 1-1.15.
8. The method for removing acetone from acetonitrile as a product according to claim 1, wherein the refluxing time is 10min to 60 min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911203010.4A CN111056975A (en) | 2019-11-29 | 2019-11-29 | Method for removing acetone from acetonitrile product |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911203010.4A CN111056975A (en) | 2019-11-29 | 2019-11-29 | Method for removing acetone from acetonitrile product |
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| Publication Number | Publication Date |
|---|---|
| CN111056975A true CN111056975A (en) | 2020-04-24 |
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| CN201911203010.4A Pending CN111056975A (en) | 2019-11-29 | 2019-11-29 | Method for removing acetone from acetonitrile product |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1231282A (en) * | 1998-02-23 | 1999-10-13 | 标准石油公司 | Improved purification and recovery of acetonitrile |
| CN102895837A (en) * | 2012-02-13 | 2013-01-30 | 中国人民解放军海军医学研究所 | Composition used for eliminating compounds of aldehydes and ketones |
| CN103163270A (en) * | 2013-03-28 | 2013-06-19 | 中国烟草总公司郑州烟草研究院 | Method for detecting eight volatile carbonyl compounds in cigarette filter tip through liquid chromatography-tandem mass spectrometry |
| CN107935887A (en) * | 2017-12-21 | 2018-04-20 | 上海应用技术大学 | A kind of preparation method of gradient level acetonitrile |
| CN109476619A (en) * | 2016-07-20 | 2019-03-15 | 巴斯夫欧洲公司 | Method for purifying propylene oxide |
-
2019
- 2019-11-29 CN CN201911203010.4A patent/CN111056975A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1231282A (en) * | 1998-02-23 | 1999-10-13 | 标准石油公司 | Improved purification and recovery of acetonitrile |
| CN102895837A (en) * | 2012-02-13 | 2013-01-30 | 中国人民解放军海军医学研究所 | Composition used for eliminating compounds of aldehydes and ketones |
| CN103163270A (en) * | 2013-03-28 | 2013-06-19 | 中国烟草总公司郑州烟草研究院 | Method for detecting eight volatile carbonyl compounds in cigarette filter tip through liquid chromatography-tandem mass spectrometry |
| CN109476619A (en) * | 2016-07-20 | 2019-03-15 | 巴斯夫欧洲公司 | Method for purifying propylene oxide |
| CN107935887A (en) * | 2017-12-21 | 2018-04-20 | 上海应用技术大学 | A kind of preparation method of gradient level acetonitrile |
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Application publication date: 20200424 |