CN106588669A - Method for continuously preparing nitroanisole by utilizing micro-channel reaction system - Google Patents
Method for continuously preparing nitroanisole by utilizing micro-channel reaction system Download PDFInfo
- Publication number
- CN106588669A CN106588669A CN201710023473.7A CN201710023473A CN106588669A CN 106588669 A CN106588669 A CN 106588669A CN 201710023473 A CN201710023473 A CN 201710023473A CN 106588669 A CN106588669 A CN 106588669A
- Authority
- CN
- China
- Prior art keywords
- reaction
- nitro
- chlorobenzene
- reaction system
- nitroanisole
- 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.)
- Granted
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 34
- BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 title claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 28
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 238000010924 continuous production Methods 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- -1 polytetrafluoroethylene Polymers 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 abstract description 6
- 238000009776 industrial production Methods 0.000 abstract description 5
- 230000004907 flux Effects 0.000 abstract description 3
- 238000005086 pumping Methods 0.000 abstract description 2
- 238000005194 fractionation Methods 0.000 abstract 1
- 239000011259 mixed solution Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000006198 methoxylation reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- PDIKQPGNGBZFRQ-UHFFFAOYSA-N 4-n-(4-methoxyphenyl)benzene-1,4-diamine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC(OC)=CC=C1NC1=CC=C(N)C=C1.C1=CC(OC)=CC=C1NC1=CC=C(N)C=C1 PDIKQPGNGBZFRQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010054949 Metaplasia Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Abstract
The invention discloses a method for continuously preparing nitroanisole by utilizing a micro-channel reaction system. The method comprises the following steps of dissolving a methanol solution of sodium methylate and nitrochlorobenzene solid in methanol; pumping a mixed solution into the micro-channel reaction system; performing a reaction at 100-140 DEG C; and cooling and collecting a mixture obtained after the reaction is ended, and performing fractionation to remove a solvent, thereby obtaining nitroanisole. The method is high in reaction time conversion rate, high in flux, stable in product quality and suitable for industrial production.
Description
Technical field
The invention belongs to the field of chemical synthesis, and in particular to one kind utilizes microchannel reaction system continuous production of nitrobenzol first
The method of ether.
Background technology
Nitroanisole, can be used to produce the dyestuffs such as Fast Blue VB salt, purplish red color base GP, azoic coupling component AS, be to be situated between into pigment, dyestuff
With the important intermediate of medicine, as important organic intermediate, in recent years since due to industry such as China's weaving, dyestuff, pharmacy
Development, and the increase of domestic and international market demand, so as to there is huge market prospects.
The production of domestic paranitroanisole is mainly catalyzed methoxylation, nitrophenol catalysis methoxyl group nitro-chlorobenzene
Change, the nitrification of methyl phenyl ethers anisole, the etherificate of nitro-chlorobenzene, phase transfer catalysis process etc..At present most common method is nitro-chlorobenzene catalysis
The etherificate of methoxylation and nitro-chlorobenzene.
At present, domestic industry metaplasia produce Nitroanisole method be with nitro-chlorobenzene, methyl alcohol and NaOH as raw material,
10～13h methoxylations are carried out under the pressure of 0.3MPa, then Jing vacuum distillations obtain paranitroanisole.Reaction need to be in pressure
Carry out in power kettle, the time is long, accessory substance is more, methanol usage is big, conversion ratio and yield are low, the problems such as environmental pollution.
Except in a kettle. without catalyst methoxylation method in addition to, Yu Shanxin and Wen Ruiming et al. have invented a kind of simple conjunction
Cheng Fa.When not using catalyst, methyl alcohol and NaOH reaction are raw first into sodium methoxide, and sodium methoxide is generated again with nitro-chlorobenzene reaction
Nitroanisole.This method mild condition, it is simple to operate, but in the case of without catalyst, usual reaction rate is slow, takes
It is long, and accessory substance nitrophenol is more, and environmental pollution is more serious.Yu Shanxin et al. is provided without catalyst and is closed with simplified method
Into and the heating response in the water-bath of (65 scholar 2) DEG C, research finds, it is longer to react the product melting range obtained after certain hour, face
Color is deeper, illustrates that reaction is incomplete, and has accessory substance to generate.Replaced finding that accessory substance is few after NaOH with KOH, the product for obtaining
Comparison is pure.But course of reaction is complicated, yield is not significantly lifted, and is not widely popularized the features such as poor continuity.
The Chinese patent CN105503610A of Sinopec Group discloses a kind of using heart-shaped micro- logical
The method that road reactor produces Nitroanisole.The method advantage can be continuous sample introduction, shorten the reaction time, but the method
In have numerous shortcomings, such as, it is impossible to be directly realized by amplification technique production, stopping state cannot solve, and heart-shaped microchannel plate should nothing
Method is cleaned, and microchannel material is expensive, and production cost is high, and wastewater flow rate is more etc., and the method pertains only to the synthesis of ortho-nitroanisole.
The Chinese patent CN104557557A of Sinopec Group is disclosed between one kind nitro-chlorobenzene
The method that position oil prepares Nitroanisole.Do not adopt water as solvent in the method, successfully solve wastewater problem.But should
Using meta oil in method, the reaction of design is HTHP, improves industrial cost and safety issue.
The Chinese patent CN205653373U of Hubei east Co., Ltd, the China of Zhejiang Co., Ltd of Run Tu research institutes is specially
Sharp CN105399634A, the Chinese patent CN103396318A of Zhejiang Dibang Chemical Co., Ltd. had also been disclosed once and closed
Into the method for Nitroanisole, but a large amount of waste water discharges are all there are, operating procedure is numerous and diverse, and security is uncontrollable, and equipment takes up an area
Area is excessive, and industry expands difficult, the problems such as industrial production high cost.
The yield and conversion ratio of product is all between 65～75% in above prior art.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of new micro passage reaction continuous production of nitrobenzol methyl ether
Method, to solve the waste water of prior art presence, severe reaction conditions, microchannel material, reaction efficiency, industry are amplified and are set
The problems such as standby investment.
To solve the above problems, the technical solution used in the present invention is as follows：
A kind of method of microchannel reaction system continuous production of nitrobenzol methyl ether, comprises the steps：
(1) methanol solution of sodium methoxide and nitro-chlorobenzene solid dissolving are formed in methyl alcohol homogeneous phase solution；
(2) homogeneous phase solution obtained in step (1) is pumped in the reaction system of microchannel, is reacted at 100～140 DEG C,
The mixture cooling that reaction is obtained after terminating is collected aftercut and removes solvent, obtains Nitroanisole.Preferably, it is described anti-
The temperature answered is 120～130 DEG C.
The nitro-chlorobenzene is 1 with the mol ratio of the sodium methoxide:0.8～2, preferably 1:1.2～1.5；It is described anti-
The time answered is 0.5～30min, preferably 25～30min；The flow velocity of the reaction is 0.06～2mL/min, preferably
0.08～0.6mL/min.
The sodium methoxide is obtained by the way that NaOH is dissolved in methyl alcohol, at normal temperatures, NaOH is dissolved in into first
In alcohol, the NaOH is 1 with the preferred mol ratio of methyl alcohol:10, obtain the sodium methoxide of 2.47mol/L.
The size internal diameter of the micro passage reaction is 0.5～5mm, and length is 0.5～40m.
Described micro passage reaction is pore passage structure, and the material in the duct is polytetrafluoroethylene (PTFE), the number in the duct
Measure as 5～30, duct quantity is decreased or increased as needed, it is possible to achieve the increase of reacting dose, be embodied directly in microchannel
In reactor synthesizing nitryl methyl phenyl ethers anisole reaction from laboratory lab scale toward pilot scale and the direct transition of industrialized big examination.
The reaction system also controls the pressure in reaction system using one-way back pressure valve, can improve reaction process
In security while reaction yield is brought up to into 95% by 85% in conventional microreactor.The nitro-chlorobenzene is selected from
Any one or two kinds of in ortho position or contraposition nitro-chlorobenzene.
Due to suitable concentration system in reaction system of the present invention, it is not necessary to additionally add water or other solvents.It is of the invention anti-
Process is answered not use any catalyst.
Compared with prior art, using the system that need not additionally add water in (1) present invention, solvent can be straight in product
Connect to steam again and recycled；(2) it is related to system without solid insoluble in the present invention, without microchannel blockage problem, is easy to directly
It is amplified to industrial production.(3) the micro passage reaction material adopted in the present invention is readily transported and drops significantly for polytetrafluoroethylene (PTFE)
Low production cost；(4) present invention is without using catalyst, and it is long to overcome reaction time in prior art, and production cost is high, energy consumption
Height, the shortcomings of danger coefficient is high；(5) reaction time shortens in the present invention, and the conversion ratio of reaction is improved, high flux, the matter of product
Amount is stable, and continuity height is conducive to continuous uninterrupted amplification production, simple to operate, safe, can effectively overcome traditional anti-
Answer the shortcoming of kettle；(6) it is related to the production of ortho position and contraposition Nitroanisole in the present invention, industrially solves equipment investment and ask
Topic；(7) involved reaction is flat top response in the present invention, it is adaptable to industrial production；(8) product yield of the invention be 88～
96%, yield reaches as high as 95%.
Beneficial effect：Reaction time high conversion rate of the invention, flux is high, and product quality is stable, it is adaptable to industrial production.
Description of the drawings
Fig. 1 reaction process schematic diagrams of the present invention, wherein 1 be injector, 2 be micro passage reaction, 3 be one-way back pressure valve, 4
For sample receiver.
Specific embodiment
According to following embodiments, the present invention may be better understood.However, as it will be easily appreciated by one skilled in the art that real
Apply the content described by example and be merely to illustrate the present invention, and should not also without limitation on sheet described in detail in claims
Invention.
It is prepared by the methanol solution of sodium methoxide：Under normal temperature, NaOH is dissolved in methyl alcohol, NaOH and Methanol Molar
Than for 1:10, obtain the methanol solution of the sodium methoxide of 2.47mol/L.
The microreactor that the present invention is used is made by oneself by 3D printer, and coil pipe internal diameter is 0.5mm, and length is 0.5m, duct
Quantity be 8.
Embodiment 1
0.5514g paranitrochlorobenzenes (3.5mmol, 1.0equiv) are weighed, is measured on 1.7ml (4.2mmol, 1.2equiv)
The methanol solution of the sodium methoxide of configuration is stated, is dissolved with the methyl alcohol of 33.3ml, be loaded in until completely dissolved in syringe.Reactant liquor
In pumping into the reactor that coil pipe internal diameter is 0.5mm, the flow velocity of microreactor is 0.6mol/min, and reaction controlling is stopped at 105 DEG C
Time 4min.Reaction process (petroleum ether is detected by TLC：Ethyl acetate=50:1 launches).Water washing, point liquid, water mutually uses second
Acetoacetic ester is extracted three times, merges organic phase, uses saturated common salt water washing, anhydrous sodium sulfate drying, Jing analyses after concentration to turn
Rate is 89%, yield 75%
The reactions steps of embodiment 2～11 and comparative example D1～D4 are consistent with embodiment 1, different parameter and obtain
Conversion ratio and yield be shown in Table 1.Wherein S1 is paranitrochlorobenzene, and S2 is 2- nitro-chlorobenzenes, and T is the reaction time, and M is nitro-chlorobenzene
With the mol ratio of the sodium methoxide, V is the flow velocity of reaction, and solvent is water in the reaction of subscript b, in the reaction of subscript c, microchannel
Without counterbalance valve in reaction system.
By result in comparative example D1～D3 understand solvent be water when, reaction yield is substantially reduced；It is micro- from comparative example D4
Substantially reduce without counterbalance valve reaction yield in pathway reaction system.
The method that table 1 utilizes microchannel reaction system continuous production of nitrobenzol methyl ether
Claims (8)
1. a kind of method of utilization microchannel reaction system continuous production of nitrobenzol methyl ether, it is characterised in that comprise the steps：
(1) methanol solution of sodium methoxide and nitro-chlorobenzene solid dissolving are formed in methyl alcohol homogeneous phase solution；
(2) homogeneous phase solution obtained in step (1) is pumped in the reaction system of microchannel, is reacted at 100～140 DEG C, reaction
The mixture cooling obtained after end is collected aftercut and removes solvent, obtains Nitroanisole.
2. method according to claim 1, it is characterised in that the nitro-chlorobenzene is 1 with the mol ratio of the sodium methoxide:
0.8～2, the time of the reaction is 0.5～30min, and the flow velocity of the reaction is 0.06～2mL/min.
3. method according to claim 1, it is characterised in that the methanol solution of the sodium methoxide is by molten by NaOH
Solution is obtained in methyl alcohol.
4. method according to claim 1, it is characterised in that the microchannel reaction system includes being gone here and there successively by pipeline
Injector, micro passage reaction, one-way back pressure valve and sample receiver that connection connects.
5. method according to claim 4, it is characterised in that should by the microchannel plate by the one-way back pressure valve
The back pressure of system is controlled in 7～15bar.
6. method according to claim 4, it is characterised in that described micro passage reaction is pore passage structure, the hole
The material in road is polytetrafluoroethylene (PTFE), and the quantity in the duct is 5～30.
7. method according to claim 4, it is characterised in that the size internal diameter of the micro passage reaction is 0.5～
5mm, length is 0.5～40m.
8. method according to claim 1, it is characterised in that the nitro-chlorobenzene is in ortho position or contraposition nitro-chlorobenzene
Any one or two kinds of.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710023473.7A CN106588669B (en) | 2017-01-13 | 2017-01-13 | A method of utilizing microchannel reaction system continuous production of nitrobenzol methyl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710023473.7A CN106588669B (en) | 2017-01-13 | 2017-01-13 | A method of utilizing microchannel reaction system continuous production of nitrobenzol methyl ether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106588669A true CN106588669A (en) | 2017-04-26 |
| CN106588669B CN106588669B (en) | 2018-09-11 |
Family
ID=58584683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710023473.7A Active CN106588669B (en) | 2017-01-13 | 2017-01-13 | A method of utilizing microchannel reaction system continuous production of nitrobenzol methyl ether |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106588669B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003052A (en) * | 2019-05-17 | 2019-07-12 | 常州工程职业技术学院 | A method of using micro passage reaction synthesizing o-hydroxy formonitrile HCN |
| CN115175888A (en) * | 2019-12-19 | 2022-10-11 | 联邦科学和工业研究组织 | Preparation of haloalkoxyethanes |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1437355A1 (en) * | 2003-01-07 | 2004-07-14 | Bayer Chemicals AG | Copper carbene complexes and the use thereof |
| WO2008136770A1 (en) * | 2007-05-02 | 2008-11-13 | Agency For Science, Technology And Research | Poly-n-heterocyclic carbene transition metal complexes and n-heterocyclic carbene transition metal complexes for carbon-sulfur and carbon-oxygen coupling reactions |
| CN102276483A (en) * | 2011-06-30 | 2011-12-14 | 辽宁世星药化有限公司 | Production method of oamino pheylmethyl ether |
| CN105399634A (en) * | 2015-11-23 | 2016-03-16 | 浙江闰土研究院有限公司 | Clean production method of paranitroanisole |
| CN105503610A (en) * | 2014-09-23 | 2016-04-20 | 中国石油化工股份有限公司 | Method for preparing o-nitro anisole by using micro-channel reaction apparatus |
| CN106279664A (en) * | 2016-08-22 | 2017-01-04 | 江苏擎宇化工科技有限公司 | A kind of method using micro passage reaction to produce alcoxylates |
-
2017
- 2017-01-13 CN CN201710023473.7A patent/CN106588669B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1437355A1 (en) * | 2003-01-07 | 2004-07-14 | Bayer Chemicals AG | Copper carbene complexes and the use thereof |
| WO2008136770A1 (en) * | 2007-05-02 | 2008-11-13 | Agency For Science, Technology And Research | Poly-n-heterocyclic carbene transition metal complexes and n-heterocyclic carbene transition metal complexes for carbon-sulfur and carbon-oxygen coupling reactions |
| CN102276483A (en) * | 2011-06-30 | 2011-12-14 | 辽宁世星药化有限公司 | Production method of oamino pheylmethyl ether |
| CN105503610A (en) * | 2014-09-23 | 2016-04-20 | 中国石油化工股份有限公司 | Method for preparing o-nitro anisole by using micro-channel reaction apparatus |
| CN105399634A (en) * | 2015-11-23 | 2016-03-16 | 浙江闰土研究院有限公司 | Clean production method of paranitroanisole |
| CN106279664A (en) * | 2016-08-22 | 2017-01-04 | 江苏擎宇化工科技有限公司 | A kind of method using micro passage reaction to produce alcoxylates |
Non-Patent Citations (1)
| Title |
|---|
| 何伟: "微反应器在合成化学中的应用", 《应用化学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003052A (en) * | 2019-05-17 | 2019-07-12 | 常州工程职业技术学院 | A method of using micro passage reaction synthesizing o-hydroxy formonitrile HCN |
| CN115175888A (en) * | 2019-12-19 | 2022-10-11 | 联邦科学和工业研究组织 | Preparation of haloalkoxyethanes |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106588669B (en) | 2018-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2017036418A1 (en) | Smart industrial micro-channel flow reactor | |
| CN101450300A (en) | Continuous current micro-reactor and preparation method and use thereof | |
| CN102584513A (en) | Method for preparing ketal by catalysis of ionic liquid and dehydration of acid-resistant molecular sieve membrane | |
| CN102976945A (en) | Method for synthetizing ethyl chrysanthemumate compound by microreactor | |
| US9624176B2 (en) | Method for preparing caprolactam by using a microreactor under lewis acid catalysis | |
| CN106588669B (en) | A method of utilizing microchannel reaction system continuous production of nitrobenzol methyl ether | |
| CN209237970U (en) | Reactor for phenol hydroxylation preparing benzenediol | |
| CN104876807A (en) | Synthesis process of hydroxybenzene ether (III) | |
| CN103274906B (en) | A kind of ionic liquid-catalyzed lignin of microwave-assisted guanidine orients the method being converted into diphenol compounds | |
| CN105017118A (en) | Method for preparing 2-methylaziridine by using microchannel reactor | |
| CN109879746A (en) | The method of 2,3,4,5 tetra fluoro benzoic acid is continuously synthesized with micro passage reaction | |
| CN105399624A (en) | Method for preparing acetic ester by adopting acid-resistant molecular sieve membrane reactor | |
| CN109020811A (en) | The method for preparing propionic ester using microreactor | |
| CN203890273U (en) | Pilot test reaction device suitable for preparing higher methyl acrylate | |
| CN109956852A (en) | The method of energy-efficient preparing benzenediol from hydroxylating phenol | |
| CN109721485A (en) | A kind of method that oxycellulose prepares formic acid and acetic acid | |
| CN101676252A (en) | Method for preparing acetal by using glyoxal | |
| CN109621858B (en) | Method for synthesizing and separating biodiesel by utilizing catalyst wall-supported microreactor and micro-separator with interface property difference | |
| CN105503610A (en) | Method for preparing o-nitro anisole by using micro-channel reaction apparatus | |
| CN210085325U (en) | Reaction unit for preparing 3- (N, N-diallyl) amino-4-methoxyacetanilide | |
| CN110283071B (en) | System and method for synthesizing ethyl methyl oxalate based on microchannel reactor | |
| CN107033030A (en) | A kind of production technology of continuous aniline-acetonitrile | |
| CN202912930U (en) | Strengthened mixing reaction device for continuously preparing biodiesel | |
| CN204702683U (en) | The device of adjacent Aminophenethyl alcohol is synthesized in the serialization of a kind of microreactor method | |
| CN102838569B (en) | Method for synthesizing peach aldehyde by using microreactor device |
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 |