CN105503610A - Method for preparing o-nitro anisole by using micro-channel reaction apparatus - Google Patents
Method for preparing o-nitro anisole by using micro-channel reaction apparatus Download PDFInfo
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Abstract
The present invention provides a new method for preparing o-nitro anisole by using a micro-channel reactor, particularly application of a micro-channel reactor with an enhanced mass transfer unit structure to carry out a continuous flow o-nitro chloro benzene etherification reaction. According to the present invention, the mass transfer and the heat transfer can be completed dependent on the kinetic energy of the fluid without the mechanical stirring process under the reactor operation condition higher than the normal temperature, the space time reaction rate of the micro-channel reactor can be substantially improved, the temperature fluctuation and the concentration fluctuation during the reaction process can be avoided, the phenomena such as temperature runaway and overheating do not exist, and the reaction process is safe.
Description
Technical field
The invention belongs to technical field of fine, specifically, relate to a kind of method adopting microchannel reaction unit to prepare o-Nitrophenyl methyl ether.
Background technology
O-Nitrophenyl methyl ether is the important intermediate of synthetic dyestuff, spices and medicine, is the important source material of synthesis Ortho Anisidine.As everyone knows, Ortho Anisidine can manufacture more than 100 kind of fine chemicals such as azoic dyestuff, glacial dye, azoic coupling component, methyl catechol and vanillin food grade,1000.000000ine mesh, synthetic musk etc., the production technique of traditional Ortho Anisidine take ortho-nitrochlorobenzene as raw material, obtains through processes such as etherificate, hydrogenation, separation, rectifying.Domestic and international market demand constantly increases, therefore invent a kind of low cost, less energy-consumption, production Ortho Anisidine that the three wastes are few method extremely urgent especially.
Liaoning Shixing Pharmaceutical & Chemical Co., Ltd. discloses a kind of production method (Chinese patent CN201110181331.6) of Ortho Anisidine, this invention is that raw material and sodium methylate carry out methoxylation with o-Nitrochlorobenzene, obtain o-Nitrophenyl methyl ether, then o-Nitrophenyl methyl ether with methyl alcohol be solvent under catalyst action, hydrogenating reduction obtains Ortho Anisidine; Reactant through dealcoholysis, dehydrogenation, refining obtain finished product o-amino benzoyl ether product.Production process completes through sodium methylate preparation, o-Nitrochlorobenzene etherificate, methyl alcohol and nitre ether fractionation by distillation, o-Nitrophenyl methyl ether hydrogenation, hydride rectifying separation Ortho Anisidine and wastewater treatment operation.The shortcomings such as this technique has process complexity, and flow time is long.
Yangzhou Ming Ruida Chemical Technology Co., Ltd. discloses a kind of nitro-chlorobenzene that mixes in water solvent, reacts the method (Chinese patent CN200910033501.9) of producing anisidine, and mixing nitro-chlorobenzene (comprising o-Nitrochlorobenzene, p-Nitrophenyl chloride and m-nitrochlorobenzene) produces anisidine through steps such as etherificate, hydrogenation, rectifying separation in aqueous.Technological process is that (1) mixing nitro-chlorobenzene and methyl alcohol react: take water as solvent, sodium hydroxide is catalyzer; (2) aqueous phase is isolated; (3) etherificate oil shortening: etherificate oil does not need washing except alkali can be the reduction of solvent direct hydrogenation with water; (4) filtration catalizer; (5) be separated crude product: cooling, separate out organic phase, the organic phase obtained after being separated removing aqueous phase is by rectifying, and can obtain pure Para-Anisidine and Ortho Anisidine, purity all can reach more than 99%.The advantage of the method is that raw materials cost is low, and shortcoming is also that the etherification reaction time is long, and the three wastes are many.
Jiasen Chemical Industry Co., Ltd., Changzhou City discloses two patents about o-Nitrophenyl methyl ether:
(1) Jiasen Chemical Industry Co., Ltd., Changzhou City discloses a kind of method (Chinese patent CN201110328050.9) that mixing nitro-chlorobenzene prepares o-Nitrophenyl methyl ether and p-Nitromethoxybenzene, this technique is with the product of Chlorobenzene Nitration gained, ortho-nitrochlorobenzene, para-nitrochloro-benzene and a nitro chlorobenzene, this mixing nitro chlorobenzene is raw material, in methanol system, add alkali lye and the phase-transfer catalyst of 30%, the obtained o-Nitrophenyl methyl ether of reaction and p-Nitromethoxybenzene product, a nitro chlorobenzene does not participate in reaction.Although the present invention solves rectifying tower facility investment in existing o-Nitrophenyl methyl ether and p-Nitromethoxybenzene production process, energy consumption of rectification is large, the technical problem that cost is high, owing to being non-pressure process, and long reaction time, thus affect life cycle of the product and output thereof.
(2) Jiasen Chemical Industry Co., Ltd., Changzhou City also discloses one chlorobenzene production o-Nitrophenyl methyl ether, the technique (Chinese patent CN200610085488.8) of p-Nitromethoxybenzene and m-nitrochlorobenzene, this technique take chlorobenzene as raw material, chlorobenzene obtains nitro-chlorobenzene mixture through nitration reaction, directly there is etherification reaction in nitro-chlorobenzene mixture, etherification product obtains o-Nitrophenyl methyl ether through separation and purification in etherifying agent, p-Nitromethoxybenzene and m-nitrochlorobenzene product, the feature of this etherification reaction is etherifying agent can be methyl alcohol, and also can be mixture or the compound of acid binding agent and methyl alcohol, acid binding agent can be sodium hydroxide, sodium carbonate, magnesium oxide, calcium oxide, volatile salt, magnesiumcarbonate, calcium carbonate, bicarbonate of ammonia, sodium bicarbonate etc., methyltertiarvbutyl ether reactor can adopt continuous tubular reactor, the continuous stirred tank reactor (CSTR) of multi-floating bodies, batch stirred tank reactor, static mixer, dynamic mixer etc., this invention is raw materials used is mixing nitro-chlorobenzene, although solve rectifying tower facility investment, the problem that energy consumption of rectification is large, the advantage such as short when also not having a reaction bench of the present invention.
Jiangsu Kangheng Chemical Co., Ltd. discloses a kind of preparation method (Chinese patent CN201110283274.2) of anhydrous system o-nitroanisole, this technique take ortho-nitrochlorobenzene as raw material, after being warmed up to back flow reaction by the speed of intensification in 1 hour 30 DEG C after methyl alcohol, alkalization de-acidying agent mix and blend, temperature controls at 40-80 DEG C, after back flow reaction 2-10 hour, filter, after reclaiming methyl alcohol, underpressure distillation obtains o-Nitrophenyl methyl ether.The present invention is directly with ortho-nitrochlorobenzene, methyl alcohol, alkali heating gained, reaction terminates the rear storage tank that is directly pressed into by reaction solution and precipitates, reclaim methyl alcohol (directly applying mechanically) again, rectifying obtains product and unreacted ortho-nitrochlorobenzene (applying mechanically), the utilization ratio of ortho-nitrochlorobenzene can reach more than 98%, the yield of o-Nitrophenyl methyl ether reaches 92%-95%, and substantially increase the utilization ratio of methyl alcohol, decrease processing step, decrease distillation, save energy consumption, also the waste water that traditional technology produces is converted into solid waste.This invention is compared with traditional technology has that technique is short, energy consumption is low, the utilization ratio of ortho-nitrochlorobenzene is high, pollute little advantage, but the advantage such as short when this step of o-Nitrochlorobenzene etherificate does not have a reaction bench of this patent microchannel yet.
Shaoyang City Shenqiang Chemical Co., Ltd. discloses a kind of method (Chinese patent CN200910043800.0) that nitrochlorobenzene meta-position oil prepares m-nitrochlorobenzene, o-Nitrochlorobenzene, p-Nitromethoxybenzene.The nitrochlorobenzene meta-position oil containing m-nitrochlorobenzene 20% ~ 45% produced in existing nitro-chlorobenzene production process is separated into m-nitrochlorobenzene-p-Nitrophenyl chloride mixture and o-Nitrochlorobenzene product by rectificating method, m-nitrochlorobenzene-p-Nitrophenyl chloride mixture changes into m-nitrochlorobenzene-p-Nitromethoxybenzene mixture further by methoxylation, then obtains m-nitrochlorobenzene and p-Nitromethoxybenzene product by rectifying separation, purification.Advantage of the present invention is less energy-consumption, with short production cycle, solves the atmosphere polluting problem of nitrochlorobenzene meta-position oil burning disposal method simultaneously, but what adopt is non-pressure process, reaction bench duration.
In addition, Jiangsu Lidaning Chemical Co., Ltd. discloses the synthetic method (Chinese patent CN201110215108.9) of a kind of o-NP and o-Nitrophenyl methyl ether, and the method comprises: (1) in a kettle. with o-Nitrochlorobenzene, water and sodium hydroxide for raw material carries out Reactive Synthesis o-NP; (2) at reactor with o-Nitrochlorobenzene, methyl alcohol and sodium hydroxide for raw material carries out Reactive Synthesis o-Nitrophenyl methyl ether.In addition, Chinese patent CN200810139122.3 also discloses a kind of preparation method of o-Nitrophenyl methyl ether, under organic solvent and alkaline state, carries out methoxylation, then adopt conventional method to collect o-Nitrophenyl methyl ether from reaction product, the molar yield of finished product can reach more than 90%.
In sum, current existing o-Nitrophenyl methyl ether production method, has plenty of raw materials cost high, has plenty of that the production cycle is long, to have plenty of energy consumption high, has plenty of the three wastes many, there is such or such problem more or less.And by there is not yet in above patent and periodical literature by micro passage reaction to prepare the report of the method for o-Nitrophenyl methyl ether, the present invention adopts the micro passage reaction with mass transfer enhancement modular construction to carry out the preparation of o-Nitrophenyl methyl ether, greatly can improve the mass transfer of ortho-nitrochlorobenzene etherification procedure, rate of heat transfer and speed of reaction.
Summary of the invention
The object of this invention is to provide a kind of novel method adopting micro passage reaction to prepare o-Nitrophenyl methyl ether.The micro passage reaction namely providing a kind of utilization to have mass transfer enhancement modular construction carries out Continuous Flow ortho-nitrochlorobenzene etherification reaction, the method can higher than under the reactor operating condition of normal temperature, the kinetic energy of fluid own is relied on to complete mass-and heat-transfer, without the need to mechanical agitation process, speed of reaction when simultaneously greatly improving micro passage reaction empty, temperature and fluctuation of concentration is avoided in reaction process, without temperature runaway and superheating phenomenon, reaction process safety.
Micro passage reaction generally refers to the small-sized reactive system manufactured through micro Process and precision processing technology.It comprises mixing tank, interchanger, reactor, controller etc. needed for chemical unit, but its line size is far smaller than conventional tube reactor, and microminiaturized structure makes it have some new characteristics.Reactor conventional mostly at present is autoclave mechanically stirred reactor or static mixing tubular type reactor, but all inevitable problem causing local superheating and equipment corrosion because mixing inequality, the transformation efficiency of reaction process is lower.Utilizing micro passage reaction to carry out the synthesising process research of ortho-nitrochlorobenzene etherification reaction, is a breakthrough of conventional etherification technology.Micro passage reaction has some characteristics not available for conventional methyltertiarvbutyl ether reactor: channel size is microminiaturized; Larger specific surface area; Excellent mass-and heat-transfer characteristic; Successive reaction; Pilot scale is not needed directly to amplify; Production is flexible and safety performance is high.Therefore utilize micro passage reaction to carry out etherification reaction and have unrivaled advantage.
The present invention's micro passage reaction used is mass transfer enhancement type micro passage reaction, and this reactive system is formed by polylith module assembled.The material of this module is silicon single crystal, special glass, pottery, the stainless steel scribbling corrosion resistant coating or metal alloy, tetrafluoroethylene etc.Reactive system can be anticorrosion withstand voltage, and it is different and different that voltage endurance capability looks material.In module, Micro Channel Architecture is divided once-through type channel architecture and strengthens mixed type channel architecture two kinds, once-through type channel architecture comprises tubular structure, strengthen mixed type channel architecture and comprise T-type structure, globosity, spherical band baffle arrangement, drops structure, heart-shaped structure, passage hydraulic diameter is 0.5mm ~ 10mm.
For achieving the above object, the technical solution used in the present invention is as follows: adopt microchannel reaction unit to prepare the method for o-Nitrophenyl methyl ether, it is characterized in that utilizing the micro passage reaction with mass transfer enhancement modular construction to carry out Continuous Flow ortho-nitrochlorobenzene etherification reaction.
Further, micro channel reactor system temperature is regulated to be 40 ~ 150 DEG C, the mixing solutions that ortho-nitrochlorobenzene, methyl alcohol, sodium hydroxide and solvent are made into is squeezed into system react, wherein the mass ratio of ortho-nitrochlorobenzene and methyl alcohol is 1:0.2-1, the mass ratio of ortho-nitrochlorobenzene and solvent is 1:0.5-4.0, and the mass ratio of ortho-nitrochlorobenzene and sodium hydroxide is 1:0.01-0.3.
In the present invention, solvent for use is alcohol or the aqueous solution, and through the product gas chromatographic analysis of microchannel reaction, the separation of product can be undertaken by ordinary method and equipment with refining.
Preferably, method feature of the present invention:
A: described etherification reaction micro passage reaction specific surface is 2500m
2/ m
3;
B: employing be multi-module structure, intermodule mode of connection and number of modules can be assembled as required, and module material is special glass, and in module, Micro Channel Architecture is heart-shaped structure;
C: the slurry flow rate of described etherification reaction is 1 ~ 80ml/min;
D: the temperature of reaction of described etherification reaction is 50 ~ 100 DEG C;
E: in described etherification reaction, the mass ratio of ortho-nitrochlorobenzene and methyl alcohol is 1:0.2-0.8, the mass ratio of ortho-nitrochlorobenzene and solvent is 1:0.8-2.0, and the mass ratio of ortho-nitrochlorobenzene and sodium hydroxide is 1:0.05-0.2;
F: the solvent particular methanol in described etherification reaction, water;
When preparing o-Nitrophenyl methyl ether with micro passage reaction, the proportioning of reactant, temperature, pressure, the reaction conditions such as reaction times and flow velocity are easy to be controlled.Reactant reacts in flow process, and by regulating the length of reactant flow velocity and microchannel, can accurately control the reaction times in micro passage reaction, therefore the concrete reaction module needed is determined by reaction time.Can continuously feeding in the preparation process of o-Nitrophenyl methyl ether, change reaction conditions flexibly, mass transfer effect is good.The specific surface area that selected micro passage reaction is larger makes reaction mass fully contact, and substantially increases reaction efficiency, Reaction time shorten, reduces energy consumption.
The present invention utilizes mass transfer enhancement type micro passage reaction to synthesize the technique of o-Nitrophenyl methyl ether compared with conventional reactor, is a very large breakthrough technically, has following advantage:
(1) accurately can control reaction conditions, strong operability, the batch mode of operation of conventional reactor has been broken in the reaction of on-line continuous, can greatly reduce the error that each periodical operation brings.
(2) what this reactor adopted is multi-module structure, intermodule mode of connection and number of modules can be assembled as required, and module material is special glass, and in module, Micro Channel Architecture is heart-shaped structure, the contact of reactant can be made so more abundant, mix more even.
(3) reactive system of multimode meets actual needs by on-off reaction passage, and tens can make reactant mix instantaneously to the microchannel of hundreds of micron, and larger heat interchanging area makes the efficiency of mass transfer and heat transfer greatly improve.
(4) micro passage reaction used in the present invention belongs to strong mass transfer, heat transfer type, and micro passage reaction specific surface area is 2500m
2/ m
3, have very large heat exchanger effectiveness, a large amount of reaction heat energy of releasing instantaneously shift out in time, maintain temperature of reaction in safety range.
(5) this ortho-nitrochlorobenzene etherification technology is continuous flowing reaction, and the reaction times shortens to several seconds to several minutes, improves the productive rate of o-Nitrophenyl methyl ether, therefore significantly improves reaction efficiency and production efficiency.
(6) the conversion unit micro passage reaction internal reinforcing type passage adopted can strengthen mass transfer, heat transfer property, keeps temperature of reaction constant, avoids temperature runaway phenomenon, reduce the generation of by product.
Accompanying drawing explanation
Fig. 1 is the internal structure schematic diagram of micro passage reaction module in the embodiment of the present invention.
Embodiment
Below by embodiment and accompanying drawing in detail the present invention is described in detail, but the invention is not restricted to following embodiment.
What in following examples, micro passage reaction adopted is multi-module structure, and intermodule mode of connection and number of modules can be assembled as required, and module material is special glass, and in module, Micro Channel Architecture is heart-shaped structure (see accompanying drawing 1).
embodiment 1
By ortho-nitrochlorobenzene 500 grams, methyl alcohol 200 grams, 25 grams, sodium hydroxide, 500 grams, water mixes, regulating thermostatic system temperature to temperature of reaction is, after 60 DEG C, with the flow of 20 ml/min, mixture is squeezed into reactive system, after reaction terminates, sampling analysis, ortho-nitrochlorobenzene transformation efficiency is 62%.
embodiment 2
By ortho-nitrochlorobenzene 500 grams, methyl alcohol 200 grams, 25 grams, sodium hydroxide, 500 grams, water mixes, regulating thermostatic system temperature to temperature of reaction is, after 80 DEG C, with the flow of 20 ml/min, mixture is squeezed into reactive system, after reaction terminates, sampling analysis, ortho-nitrochlorobenzene transformation efficiency is 75%.
embodiment 3
By ortho-nitrochlorobenzene 500 grams, methyl alcohol 200 grams, 25 grams, sodium hydroxide, 500 grams, water mixes, regulating thermostatic system temperature to temperature of reaction is, after 100 DEG C, with the flow of 20 ml/min, mixture is squeezed into reactive system, after reaction terminates, sampling analysis, ortho-nitrochlorobenzene transformation efficiency is 85%.
embodiment 4
By ortho-nitrochlorobenzene 500 grams, methyl alcohol 200 grams, 25 grams, sodium hydroxide, 500 grams, water mixes, regulating thermostatic system temperature to temperature of reaction is, after 60 DEG C, with the flow of 10 ml/min, mixture is squeezed into reactive system, after reaction terminates, sampling analysis, ortho-nitrochlorobenzene transformation efficiency is 75%.
embodiment 5
By ortho-nitrochlorobenzene 500 grams, methyl alcohol 200 grams, 25 grams, sodium hydroxide, 500 grams, water mixes, regulating thermostatic system temperature to temperature of reaction is, after 100 DEG C, with the flow of 10 ml/min, mixture is squeezed into reactive system, after reaction terminates, sampling analysis, ortho-nitrochlorobenzene transformation efficiency is 99.5%.
Claims (8)
1. adopt microchannel reaction unit to prepare a method for o-Nitrophenyl methyl ether, it is characterized in that utilizing the micro passage reaction with mass transfer enhancement modular construction to carry out Continuous Flow ortho-nitrochlorobenzene etherification reaction.
2. method according to claim 1, it is characterized in that regulating micro channel reactor system temperature to be 40 ~ 150 DEG C, the mixing solutions that ortho-nitrochlorobenzene, methyl alcohol, sodium hydroxide and solvent are made into is squeezed into system react, wherein the mass ratio of ortho-nitrochlorobenzene and methyl alcohol is 1:0.2-1, the mass ratio of ortho-nitrochlorobenzene and solvent is 1:0.5-4.0, and the mass ratio of ortho-nitrochlorobenzene and sodium hydroxide is 1:0.01-0.3.
3. method according to claim 1, what it is characterized in that described etherification reaction micro passage reaction employing is multi-module structure, intermodule mode of connection and number of modules can be assembled as required, and module material is special glass, and in module, Micro Channel Architecture is heart-shaped structure.
4. the method according to claim 1 or 3, is characterized in that described etherification reaction micro passage reaction specific surface is 2500m
2/ m
3.
5. method according to claim 1, is characterized in that the slurry flow rate of described etherification reaction is 1 ~ 80ml/min.
6. method according to claim 1, is characterized in that the temperature of reaction 50 ~ 100 DEG C of described etherification reaction.
7. method according to claim 1, it is characterized in that the mass ratio of ortho-nitrochlorobenzene and methyl alcohol in described etherification reaction is 1:0.3-0.8, the mass ratio of ortho-nitrochlorobenzene and solvent is 1:0.8-2.0, and the mass ratio of ortho-nitrochlorobenzene and sodium hydroxide is 1:0.05-0.2.
8. method according to claim 1, is characterized in that the solvent in described etherification reaction is methyl alcohol, water.
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Cited By (3)
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| CN106588669A (en) * | 2017-01-13 | 2017-04-26 | 南京工业大学 | Method for continuously preparing nitroanisole by utilizing micro-channel reaction system |
| CN108752161A (en) * | 2018-07-16 | 2018-11-06 | 山东冠森高分子材料科技股份有限公司 | The method of synthesis of alpha-single chloro ortho-xylene in continuous flow micro passage reaction |
| 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 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106588669A (en) * | 2017-01-13 | 2017-04-26 | 南京工业大学 | Method for continuously preparing nitroanisole by utilizing micro-channel reaction system |
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| 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 |
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Application publication date: 20160420 |