CN107033005B - Nitration method of aromatic compound - Google Patents
Nitration method of aromatic compound Download PDFInfo
- Publication number
- CN107033005B CN107033005B CN201510412001.1A CN201510412001A CN107033005B CN 107033005 B CN107033005 B CN 107033005B CN 201510412001 A CN201510412001 A CN 201510412001A CN 107033005 B CN107033005 B CN 107033005B
- Authority
- CN
- China
- Prior art keywords
- acid
- hypergravity
- reactor
- nitration
- aromatic compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
The invention discloses a nitration method of aromatic compounds, in particular to a nitration method of aromatic compounds in a hypergravity reactor, which comprises the following steps: inputting aromatic compounds and mixed acid into a supergravity reactor, mixing and carrying out nitration reaction to generate nitration products. The method has the characteristics of high production efficiency, low energy consumption and the like, and is an environment-friendly, safe, efficient and low-cost aromatic compound nitration method.
Description
Technical Field
The invention relates to a nitration method of aromatic compounds, in particular to a nitration method of aromatic compounds by adopting a supergravity reactor, belonging to the technical field of organic synthesis.
Background
The product of nitrated aromatic nitro compound is an important organic reaction intermediate, and can be extensively used in the fields of medicine, pesticide, dye, perfume, explosive and organic synthetic reagent, etc., and the deep-processed product of its derivative possesses higher added value, so that it can create a certain economic benefit and good social benefit for development and application of aromatic nitro compound. For example, nitro group can be converted into other substituent groups, especially into amino compounds, which are monomers of some dyes, drugs and polymers, and can also activate nucleophilic reaction by utilizing strong electron withdrawing property of nitro group, and endow organic matters with new functions by utilizing strong polarity of nitro group, for example, deepen color of dye, make physiological drug property of drugs significantly changed, and the like.
Most of reactors used for nitration reaction at present are multi-kettle series stirred tank reactors, and the kettle reactors have the defects of uneven mixing, more byproducts, complex flow and the like. In addition, most nitration reactions are violent in reaction and large in heat release, common kettle type nitration equipment is poor in heat dissipation, a large amount of materials are accumulated in nitration reactor equipment, and most organic matters are flammable and explosive, so that huge potential safety hazards exist.
Disclosure of Invention
The invention aims to provide a nitration reaction method with the advantages of low energy consumption, safety, high efficiency and the like, so as to overcome the defects in the prior art.
In order to achieve the purpose, the invention adopts the following technical scheme:
a process for the nitration of an aromatic compound comprising: the aromatic compound and mixed acid are fed into a supergravity reactor, mixed and subjected to nitration reaction to generate a mixture containing nitration products.
As one of the more preferable embodiments, the nitration method further comprises: and (3) after the mixture containing the nitration product is subjected to heat exchange by a heat exchanger, inputting the mixture into a delayer to obtain a crude product and waste acid.
As one of the more preferable embodiments, the nitration method further comprises: and (3) treating the separated waste acid by a waste acid recoverer, mixing the waste acid with nitric acid to form mixed acid again, and circularly inputting the mixed acid into the supergravity reactor.
Further, the aromatic compound and the mixed acid enter the liquid distributor from the liquid inlet of the hypergravity reactor, then are sprayed on the inner edge of the rotor, move outwards from the inner edge of the rotor under the action of strong centrifugal force, are mixed and have nitration reaction, and the generated mixture containing nitration products leaves the hypergravity reactor from the liquid outlet.
Further, the high-gravity reactor comprises any one of a rotary packed bed, a baffling type, a spiral channel, a stator-rotor and a rotary disc high-gravity rotating device. For example, the hypergravity reactor may preferably be a rotating packed bed.
Further, in the nitration reaction process, the hypergravity level of the hypergravity reactor is preferably 2g to 800g, particularly preferably 3g to 600g, and further may preferably be 5g to 400 g.
Further, the aromatic compound may be selected from any one of benzene, alkane substituted benzene and non-alkane substituted benzene.
Further, the alkane-substituted benzene may be at least selected from any one of toluene, ethylbenzene, cumene, and xylene, but is not limited thereto.
Further, the non-alkane substituted benzene is at least selected from any one of chlorobenzene, bromobenzene, anisole, benzyl toluene, nitrobenzene and methyl benzoate.
Further, the mixed acid comprises: HNO3About 3wt% to 50wt% (preferably 3wt% to 15 wt%), H2SO4About 40wt% to 70wt% (preferably 60 wt% to 70 wt%), the remainder comprising water.
Further, the molar ratio of the nitric acid to the aromatic compound contained in the mixed acid is close to 1: 1. where "close" is to be understood as a deviation within ± 10%.
Further, the temperature of the nitration reaction is 50-150 ℃, preferably 90-140 ℃.
Furthermore, the invention relates to a stratifier is mainly used for oil-water separation of a mixture containing nitration products, wherein a crude product layer is positioned at the upper layer of the stratifier due to lower density, and dilute sulfuric acid (known as waste acid) is positioned at the lower layer of the stratifier due to higher density mainly under the well-known action of gravity. The crude product is subjected to subsequent treatment processes of washing, rectification (or distillation) purification and the like to obtain a final nitration product. Further, the general structure of the described delayer can be found in numerous published documents, such as: research on separation characteristics of gravity type oil-water separators (proceedings of Petroleum 2006, 27: 112-.
Furthermore, the waste acid recoverer is mainly used for carrying out concentration, purification and other treatments on waste acid so as to remove organic matters and part of water in the waste acid and enable the concentration and the purity of the waste acid to meet the requirements required by reaction. In addition, inevitably, a certain amount of loss is generated in the recycling process of the sulfuric acid, and when the loss amount reaches a certain degree along with the increase of the recycling times of the mixed acid, the concentrated sulfuric acid can be added into the mixed acid for supplement as required. When the waste acid is treated in the waste acid recoverer, modes such as evaporation or flash evaporation can be adopted, and the waste acid recovery device can be used in one of modes such as a thin film evaporator, a rotary evaporator and a flash tank.
In the present invention, the aforementioned "supergravity" refers to a force to which a substance is subjected in an environment much larger than the acceleration of gravity of the earth. Under the supergravity environment which is larger than the earth gravity field, especially hundreds to thousands of times, different materials flow and contact in a porous medium or a pore channel, the liquid phase materials are torn into films, threads and drops by strong shearing force, a huge and fast updated phase interface is generated, the inter-phase mass transfer rate is improved by 1 to 3 orders of magnitude compared with that in the traditional tower, and the micro-molecular mixing and mass transfer process is highly strengthened.
Because the micro mixing of materials can be quickly realized in the hypergravity reactor, on one hand, the reaction time can be obviously shortened, and the yield can be improved, compared with a kettle type reactor, the reaction time can be shortened to less than one minute from more than ten minutes, and the yield can be improved by about 1-3%; on the other hand, the side reaction can be reduced, compared with other methods, the content of the by-products of polynitro substances in the obtained product can be reduced by about 90 percent to the maximum extent, thereby greatly improving the production efficiency and the product quality.
The structure and operation principle of the aforementioned supergravity reactor can be found in the following technical documents and literature: supergravity technology and its application-new generation reaction and separation technology (written by Chenjian mountain, etc., published by chemical industry Press, published time 2009-01-01, ISBN: 9787502538422), CN1116125A, CN1116125A, CN1059105A, etc.
Because of the structural characteristics of the hypergravity reactor, the generated mixture containing the nitration product quickly leaves the hypergravity reactor through the hypergravity liquid outlet pipe, so that the materials in the reactor are rarely accumulated, and the potential safety hazards of explosion, combustion and the like caused by the large amount of reaction materials stored in the reactor are greatly reduced.
Compared with the prior art, the invention has at least the following beneficial effects:
(1) the method of the invention adopts the nitrification reaction in the high-gravity rotating bed reactor, can realize the rapid micro-mixing between the aromatic compound and the nitrating agent, not only can avoid the side reaction caused by overhigh local concentration, but also can accelerate the nitrification reaction and improve the production efficiency, therefore, the method of the invention is an efficient and low-energy-consumption nitrification method.
(2) In the method, the accumulation amount of materials in the reactor is very small, and the potential safety hazards of easy combustion or explosion and the like of the traditional nitration process can be obviously improved, so the method is a safe nitration method.
Drawings
FIG. 1 is a flow diagram of a nitration process in an exemplary embodiment of the invention.
Detailed Description
As described above, in view of the deficiencies in the prior art, the inventors of the present invention have made extensive studies and extensive practices to propose a technical solution of the present invention. As described in detail below.
Referring to FIG. 1, in a more typical preferred embodiment of the present invention, a process for the nitration of an aromatic compound may comprise the steps of: inputting aromatic compound and mixed acid into a supergravity reactor (1), mixing and carrying out nitration reaction to generate a mixture containing a nitration product, carrying out heat exchange on the mixture and the aromatic compound through a heat exchanger (2), then feeding the mixture into a delayer (3) to obtain a crude product and waste acid, treating the waste acid through a waste acid recoverer (4), mixing the waste acid and nitric acid to obtain the mixed acid, and circularly feeding the mixed acid into the supergravity reactor (1).
The technical solution of the present invention is described in more detail with reference to several embodiments.
Example 1 a hypergravity rotating packed bed was used as the core reactor device, setting the hypergravity level to 2-5 g. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting benzene and the mixed acid into a hypergravity reactor 1, efficiently mixing materials in the hypergravity reactor and carrying out nitration reaction, enabling the reacted materials to enter a heat exchanger 2, carrying out heat exchange and then entering a delayer 3, carrying out layering, carrying out subsequent purification treatment on an upper-layer crude product to obtain a final product, enabling waste acid obtained by layering to enter a waste acid recoverer 4, carrying out concentration on the waste acid and then mixing the waste acid with the nitric acid to obtain the mixed acid, recycling the mixed acid, and simultaneously inputting the mixed acid and the benzene into the hypergravity reactor 1. The reaction-related conditions are shown in Table 1, and the yield is 99% by analysis.
Example 2 a hypergravity level to 800g was set using a hypergravity rotating packed bed as core reactor device. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting methylbenzene and the mixed acid into a supergravity reactor 1, efficiently mixing materials in the supergravity reactor and carrying out nitration reaction, enabling the reacted materials to enter a heat exchanger 2, carrying out heat exchange and then entering a delayer 3, carrying out layering, carrying out subsequent purification treatment on an upper-layer crude product to obtain a final product, enabling waste acid obtained by layering to enter a waste acid recoverer 4, carrying out concentration on the waste acid and then mixing the waste acid with the nitric acid to obtain the mixed acid, recycling the mixed acid, and simultaneously inputting the mixed acid and the methylbenzene into the supergravity reactor 1. The reaction-related conditions are shown in Table 1, and the yield is 99.2% by analysis and detection.
Example 3 a baffled hypergravity reactor was used as the core reactor unit, setting the hypergravity level to 150 g. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting chlorobenzene and the mixed acid into a hypergravity reactor 1, efficiently mixing materials in the hypergravity reactor and carrying out nitration reaction, enabling the reacted materials to enter a heat exchanger 2, carrying out heat exchange and then entering a delayer 3, layering, carrying out subsequent purification treatment on an upper-layer crude product to obtain a final product, enabling waste acid obtained by layering to enter a waste acid recoverer 4, concentrating the waste acid and mixing the waste acid with the nitric acid to obtain the mixed acid, recycling the mixed acid, and simultaneously inputting the mixed acid and the chlorobenzene into the hypergravity reactor 1. The reaction-related conditions are shown in Table 1, and the yield is 98.5% by analysis and detection.
Example 4 a hypergravity level to 500g was set using a hypergravity rotating packed bed as core reactor device. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting methylbenzene and the mixed acid into a supergravity reactor 1, efficiently mixing materials in the supergravity reactor and carrying out nitration reaction, enabling the reacted materials to enter a heat exchanger 2, carrying out heat exchange and then entering a delayer 3, carrying out layering, carrying out subsequent purification treatment on an upper-layer crude product to obtain a final product, enabling waste acid obtained by layering to enter a waste acid recoverer 4, carrying out concentration on the waste acid and then mixing the waste acid with the nitric acid to obtain the mixed acid, recycling the mixed acid, and simultaneously inputting the mixed acid and the methylbenzene into the supergravity reactor 1. The reaction-related conditions are shown in Table 1, and the yield is 99.5% by analysis and detection.
Example 5a hypergravity rotating packed bed was used as the core reactor device, setting the hypergravity level to 600-650 g. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting ethylbenzene and the mixed acid into a hypergravity reactor 1, efficiently mixing materials in the hypergravity reactor and carrying out nitration reaction, enabling the reacted materials to enter a heat exchanger 2, carrying out heat exchange and then entering a delayer 3, layering, carrying out subsequent purification treatment on an upper-layer crude product to obtain a final product, enabling waste acid obtained by layering to enter a waste acid recoverer 4, concentrating the waste acid and mixing the waste acid with the nitric acid to obtain the mixed acid, recycling the mixed acid, and simultaneously inputting the mixed acid and the ethylbenzene into the hypergravity reactor 1. The reaction-related conditions are shown in Table 1, and the yield is 99.2% by analysis and detection.
Example 6 a core reactor set was prepared using a stator-rotor hypergravity spinning apparatus set to a hypergravity level of 400 g. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting dimethylbenzene and the mixed acid into a hypergravity reactor 1, efficiently mixing materials in the hypergravity reactor and carrying out nitration reaction, enabling the reacted materials to enter a heat exchanger 2, carrying out heat exchange and then entering a delayer 3, carrying out layering, carrying out subsequent purification treatment on an upper-layer crude product to obtain a final product, enabling waste acid obtained by layering to enter a waste acid recoverer 4, concentrating the waste acid, mixing the waste acid with the nitric acid to obtain the mixed acid, recycling the mixed acid, and simultaneously inputting the mixed acid and the dimethylbenzene into the hypergravity reactor 1. The reaction-related conditions are shown in Table 1, and the yield is 98.2% by analysis and detection.
Example 7 a hypergravity level to 200g was set using a hypergravity rotating packed bed as core reactor device. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting nitrotoluene and the mixed acid into a supergravity reactor 1, efficiently mixing materials in the supergravity reactor and carrying out nitration reaction, enabling the reacted materials to enter a heat exchanger 2, carrying out heat exchange and then entering a delayer 3, carrying out layering, carrying out subsequent purification treatment on an upper-layer crude product to obtain a final product, enabling waste acid obtained by layering to enter a waste acid recoverer 4, concentrating the waste acid, mixing the concentrated waste acid with the nitric acid to obtain the mixed acid, recycling the mixed acid, and simultaneously inputting the mixed acid and the nitrotoluene into the supergravity reactor 1. The reaction-related conditions are shown in Table 1, and the yield is 97.1% by analysis and detection.
Example 8 a hypergravity level to 300g was set using a hypergravity rotating packed bed as core reactor device. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting the methyl benzoate and the mixed acid into a supergravity reactor 1, efficiently mixing the materials in the supergravity reactor and carrying out nitration reaction, enabling the reacted materials to enter a heat exchanger 2, carrying out heat exchange, then entering a delayer 3, layering, carrying out subsequent purification treatment on an upper-layer crude product to obtain a final product, enabling waste acid obtained by layering to enter a waste acid recoverer 4, concentrating the waste acid, mixing the concentrated waste acid with the nitric acid to obtain the mixed acid, recycling the mixed acid, and simultaneously inputting the mixed acid and the methyl benzoate into the supergravity reactor 1. The reaction-related conditions are shown in Table 1, and the yield is 98.2% by analysis and detection.
Comparative example 1 a stirred tank reactor was used as the core reactor apparatus. Mixing a certain amount of sulfuric acid, nitric acid and water to obtain mixed acid, simultaneously inputting benzene and the mixed acid into a stirring reaction kettle, and reacting while stirring. The reaction-related conditions are shown in Table 1, and the yield is 96.5% by analysis and detection.
Comparative example 2 a three-pot tandem stirred tank reactor was used as the core reactor apparatus. Taking a certain amount of sulfuric acid, nitric acid and water to mix into mixed acid, simultaneously inputting toluene and the mixed acid into a first stirring reaction kettle, reacting while stirring, and continuously reacting the mixed material sequentially through a second stirring reaction kettle and a third stirring reaction kettle. The reaction-related conditions are shown in Table 1, and the yield is 97.6% by analysis and detection.
TABLE 1 reaction conditions adopted in examples 1 to 8 and comparative examples 1 to 2
It should be noted that the above is only a specific application example of the present invention, and the protection scope of the present invention is not limited in any way. All the technical solutions formed by equivalent transformation or equivalent replacement fall within the protection scope of the present invention.
Claims (4)
1. A method for nitrating an aromatic compound, comprising:
inputting an aromatic compound and mixed acid into a hypergravity reactor (1), mixing and carrying out nitration reaction to generate a mixture containing a nitration product, wherein the hypergravity level of the hypergravity reactor is 2 g-800 g in the nitration reaction process, the nitration reaction temperature is 50-150 ℃, the aromatic compound is selected from any one of benzene, toluene, ethylbenzene, cumene, xylene, chlorobenzene, bromobenzene, anisole, benzyl toluene, nitrobenzene and methyl benzoate, and the mixed acid contains water and 3wt% -50 wt% of HNO3And 40wt% to 70wt% H2SO4HNO contained in the mixed acid3The molar ratio to the aromatic compound is 1: 1, the hypergravity reactor is selected from any one of a rotating packed bed, a baffling type, a stator-rotor and a rotating disc hypergravity rotating device;
after the mixture containing the nitration product is subjected to heat exchange by a heat exchanger (2), the mixture is input into a delayer (3) to obtain a crude product and waste acid;
and (3) treating the separated waste acid by a waste acid recoverer (4), mixing the waste acid with nitric acid to form mixed acid again, and circularly inputting the mixed acid into the super-gravity reactor (1).
2. The method for nitrating an aromatic compound according to claim 1, wherein the hypergravity level of the hypergravity reactor is 3g to 600g during the nitration reaction.
3. The method for nitrating an aromatic compound according to claim 2, wherein the hypergravity level of the hypergravity reactor is 5g to 400g during the nitration reaction.
4. The method for nitrating an aromatic compound according to any one of claims 1 to 3, wherein the temperature of the nitration reaction is 90 ℃ to 140 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510412001.1A CN107033005B (en) | 2015-07-14 | 2015-07-14 | Nitration method of aromatic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510412001.1A CN107033005B (en) | 2015-07-14 | 2015-07-14 | Nitration method of aromatic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107033005A CN107033005A (en) | 2017-08-11 |
| CN107033005B true CN107033005B (en) | 2020-08-11 |
Family
ID=59532759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510412001.1A Active CN107033005B (en) | 2015-07-14 | 2015-07-14 | Nitration method of aromatic compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107033005B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109796343A (en) * | 2018-12-28 | 2019-05-24 | 阜宁县安勤化学有限公司 | A kind of ethyl benzene mixed acid nitrification Waste Sulfuric Acid circulation utilization method |
| CN114105831B (en) * | 2021-11-30 | 2024-01-26 | 浙江大井化工有限公司 | Method and apparatus for continuous production of 6-nitro-1, 2, 4-acid oxygen |
| CN114149326A (en) * | 2021-12-14 | 2022-03-08 | 江苏亚邦染料股份有限公司 | Method for preparing 1-nitroanthraquinone by using supergravity nitration reactor |
| CN115583894B (en) * | 2022-10-09 | 2024-02-27 | 浙江迪邦化工有限公司 | Method and device for continuously producing 2-nitro-4-methoxy acetanilide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276470A (en) * | 2010-06-08 | 2011-12-14 | 中国石油化工集团公司 | Method for nitrifying aromatic hydrocarbon compound by continuous countercurrent |
| CN202860157U (en) * | 2012-10-23 | 2013-04-10 | 神华集团有限责任公司 | Composite packing type counterflow rotating packed bed device |
| CN103044261A (en) * | 2013-01-18 | 2013-04-17 | 徐德良 | Safe production method of nitro-compound |
-
2015
- 2015-07-14 CN CN201510412001.1A patent/CN107033005B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276470A (en) * | 2010-06-08 | 2011-12-14 | 中国石油化工集团公司 | Method for nitrifying aromatic hydrocarbon compound by continuous countercurrent |
| CN202860157U (en) * | 2012-10-23 | 2013-04-10 | 神华集团有限责任公司 | Composite packing type counterflow rotating packed bed device |
| CN103044261A (en) * | 2013-01-18 | 2013-04-17 | 徐德良 | Safe production method of nitro-compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107033005A (en) | 2017-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107033005B (en) | Nitration method of aromatic compound | |
| CN108840310B (en) | Device and process for producing hydrogen chloride by deep analysis from dilute hydrochloric acid | |
| CN102464521B (en) | Method for synthesizing cyclic carbonate ester in micro reactor system | |
| CN102838489B (en) | Clean production method and device of dinitrotoluene | |
| CN105330549A (en) | Method for preparing isooctyl nitrate in micro-channel reactor | |
| CN102285641A (en) | Recycling process of waste hydrochloric acid | |
| CN108997127B (en) | Production process for synthesizing 1, 3-di- (2-chloro-4-trifluoromethylphenoxy) -4-nitrobenzene | |
| CN107311868A (en) | A kind of method for preparing p-tert-butyl benzoic acid methyl esters | |
| CN104874196B (en) | A kind of method processing sodium and ammonium acetate salt-diazonium Organic substance-methanol-water mixed solution | |
| CN104829408B (en) | A kind of ethyl acetate and the separation method of hexamethylene | |
| WO2024001054A1 (en) | Production method for nitrobenzene | |
| CN115043732A (en) | Preparation method of 2, 4-dinitrochlorobenzene | |
| CN103772185A (en) | Device and method for removing moisture and heteroacids in acetic acid | |
| CN104418752B (en) | Method for synthesizing single nitro-o-xylene employing catalytic nitration in micro-reactor | |
| CN103304442A (en) | Process for synthesizing diacetylmonoxime ethyl ether by continuous reactions in microtube | |
| CN114105754B (en) | Organic sodium salt treatment process and device in toluene oxidation process | |
| CN113620835B (en) | Method for separating aldoxime and cyclohexanone | |
| CN103073497B (en) | Method and device for preparing caprolactam through cyclohexanone oxime rearrangement reaction | |
| CN112979472B (en) | Method for continuously producing dinitrobenzene | |
| CN214514479U (en) | Micro-channel reactor system for nitration reaction | |
| CN108721942A (en) | A kind of continuous flow upstream extraction of liquid phase mixture washes reaction process and application | |
| CN100361958C (en) | Method for extracting nitrocresols from waste water produced in the manufacture of mononitrotoluene and use of said extract | |
| CN106316755A (en) | Method for treating waste sulfuric acid through extraction separation coupled ammonium chloride reaction | |
| CN211998830U (en) | Continuous sodium azide aqueous phase safety production device | |
| CN109053391B (en) | Micro-reaction system and method for synthesizing 4-bromo-3-methylanisole by two-phase method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |