CN101187032A - P-aminoanisole electrochemical synthesis method - Google Patents
P-aminoanisole electrochemical synthesis method Download PDFInfo
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- CN101187032A CN101187032A CNA2007100461811A CN200710046181A CN101187032A CN 101187032 A CN101187032 A CN 101187032A CN A2007100461811 A CNA2007100461811 A CN A2007100461811A CN 200710046181 A CN200710046181 A CN 200710046181A CN 101187032 A CN101187032 A CN 101187032A
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- nitromethoxybenzene
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Abstract
Provided is an electrochemical synthetic method of aminoanisole, belonging to the technical field of electrochemistry. The method needs to be accomplished in a two-chamber electrolysis bath which is separated by employing a cation-exchange membrane, a copper sheet is taken as a negative electrode, a ruthenium net is taken as a positive electrode, a saturated calomel electrode is taken as a reference electrode, the negative electrode and the reference electrode are installed inside a cathode chamber of the electrolysis bath, and the positive electrode is installed inside an anode chamber of the electrolysis bath. Methanol is taken as solvent, sulphuric acid is taken as supporting electrolyte, paranitroanisole is taken as electrolytic reaction substrate, the solvent and the solution of supporting electrolyte are injected into the cathode chamber and the anode chamber, and the electrolytic reaction substrate is injected into the cathode chamber. The electrolyzation is performed within a condition of normal temperature and pressure and a condition that the negative electrode is added with a certain constant voltage relative to the reference electrode, and the constant voltage is between -0.4 to -0.6 V. After the electrolyzation is finished, the electrolyte is post-processed to obtain the product of paraphenetidine with the production ratio between 24.5-63.3%. The method has the advantages of simple requirement, mild reaction conditions, easy preparation of the electrodes, low price, small pollution in the process of reaction and the like, and is a greening production line.
Description
Technical field
The present invention relates to a kind of electrochemical method for synthesizing of Para-Anisidine, belong to electrochemical technical field.
Background technology
Para-Anisidine has another name called P-nethoxyaniline, popular name P-anisidine, molecular formula C
7H
9NO, white crystals, 57.2 ℃ of fusing points, 243 ℃ of boiling points, relative density 1.071, refractive index 1.5559 (57 ℃) is soluble in ethanol, methyl alcohol, benzene, ether and chloroform, is insoluble in water.Para-Anisidine is mainly used in dyestuffs industries, produces glacial dye, dispersed dye, vat dyes, cationic dyestuff, color base and azoic coupling component etc., aspect medicine industry, is used to produce Quinacrime, uncle's quinoline, INDOMETHACIN etc.
Existing production Para-Anisidine method mainly is the method for organic synthesis, include 1, the oil of mirbane method, under 75～125 ℃, 0.6～1.5MPa, with the noble metal is catalyzer, sulfuric acid, methyl alcohol or methyl-sulphoxide are solvent, make Para-Anisidine by oil of mirbane, and this method uses precious metal to make catalyzer, with high costs, and reaction conditions is relatively harsher.2, p-Nitromethoxybenzene reduction method is a raw material with the p-Nitrophenyl chloride, carries out methoxylation through methyl alcohol, alkali lye, through reduction, makes Para-Anisidine again.P-Nitromethoxybenzene reduction force method comprises: sodium sulphite reduction method, hydrazine hydrate reduction method and hydrogenating reduction method.The operation steps of sodium sulphite reduction method is: the configuration percentage concentration is 22～23% sodium sulfide solutions earlier, be heated to 95 ℃, add p-Nitromethoxybenzene, be heated to 100 ℃ under stirring, p-Nitromethoxybenzene is emulsification in sodium sulfide solution, and reduction process continues a few hours, then sedimentation, dump lower floor's waste lye, make rough Para-Anisidine, hot wash is left standstill, filtered while hot, distill under the condition of 5.33～6.0kPa and about 150 ℃, collect two portions distillate, first part steams under 145 ℃, the water that contains volume, second section are the product Para-Anisidine.The operation steps of hydrazine hydrate reduction method is: adding percentage concentration in ferric sulfate aqueous solution is 15% aqueous sodium hydroxide solution, make the pH=4.0 of reaction solution, 20～25 ℃ are stirred 15min down, the precipitation stasis of blood slurry of washing gained, adding percentage concentration is 15% aqueous sodium hydroxide solution, and the pH=8.5 of conditioned reaction liquid stirs, washing, filter, make alkali formula ironic hydroxide, 80～90 ℃ of following dry 24h, make catalyzer, the p-Nitromethoxybenzene of 15.3g and the catalyzer adding of 1g are had reflux condensing tube, temperature is taken into account in the 200ml four-hole boiling flask of dropping funnel, adds 50ml methyl alcohol again, and 60 ℃ are stirred 10min down, p-Nitromethoxybenzene is dissolving fully in solvent, then, under agitation, the concentration that drips 9.4g to reaction soln is 80% hydrazine hydrate, 60 ℃ are reacted 5h down, the filtered while hot resultant of reaction is removed catalyzer, and filtrate is removed most of methyl alcohol, cooling, Para-Anisidine is just separated out from filtrate.The operation steps of hydrogenating reduction method is: with the gac that contains 5% iridium and 0.99% boron is catalyzer, is solvent with ethanol, under the condition of 20 ℃ and 0.10Mpa, and the p-Nitromethoxybenzene hydrogenation, the reaction times is 18h, makes Para-Anisidine.The p-Nitromethoxybenzene reduction method is made catalyzer with sodium sulphite, hydrazine hydrate etc., and the generation of a large amount of alkali lye, sulfur-containing waste water etc. is arranged, and environment is caused serious pollution; Or the expensive noble metal catalyst of use, severe reaction conditions.
The prior synthesizing method of Para-Anisidine or use the comparatively expensive noble metal catalyst of price, or reaction process can produce a large amount of wastes, or reaction conditions requires harshly, and therefore, traditional production method has not had too big development prospect.
Summary of the invention
The electrochemical method for synthesizing that the purpose of this invention is to provide a kind of Para-Anisidine.This method has that equipment requirements is simple, reaction conditions is gentle, electrode is easy to preparation, low price, reaction process pollute advantages such as little, does not have the defective of prior art, is a kind of production route of green.
Technical scheme of the present invention is that described method comprises equipment preparation, electrolytic solution preparation, electrolytic process and four steps of aftertreatment: need to implement in the two chamber-type electrolyzer of separating with cationic exchange membrane, copper sheet is made negative electrode, the ruthenium net is made anode, saturated calomel electrode is made reference electrode, pack into the anolyte compartment of electrolyzer of pack into the cathode compartment of electrolyzer of negative electrode and reference electrode, anode; Methyl alcohol is made solvent, and sulfuric acid is made supporting electrolyte, and p-Nitromethoxybenzene is made the electrolytic reaction substrate, with the solution injection cathode compartment and the anolyte compartment of solvent and supporting electrolyte, the electrolytic reaction substrate is injected cathode compartment; Electrolytic process carries out under normal temperature and pressure and negative electrode are added with condition with respect to a constant voltage of reference electrode, this constant voltage between-0.4～-0.6V between; After electrolysis finished, electrolytic solution made the product Para-Anisidine through aftertreatment.
Now describe technical scheme of the present invention in detail.A kind of electrochemical method for synthesizing of Para-Anisidine is characterized in that, the concrete operations step:
The first step equipment is prepared
Described method needs to implement in the two chamber-type electrolyzer of separating with cationic exchange membrane, electrolyzer has two Room: cathode compartment and anolyte compartment, separate with cationic exchange membrane between two Room, copper sheet is made negative electrode, the ruthenium net is made anode, saturated calomel electrode is made reference electrode, with negative electrode and the reference electrode cathode compartment of packing into, with the anode anolyte compartment of packing into;
The preparation of the second one-step electrolysis liquid
Electrolytic solution divides catholyte and anolyte, the preparation catholyte, compound concentration is 0.5mol/L～2.5mol/L sulphuric acid soln, get methyl alcohol-sulphuric acid soln that methyl alcohol 20ml～22.5ml and above-mentioned sulphuric acid soln 10ml～7.5ml are mixed into 30ml, p-Nitromethoxybenzene is added methyl alcohol-sulphuric acid soln, add-on is 0.01～0.12mol/L, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.01～0.12mol, make catholyte, inject cathode compartment, by preparing methyl alcohol-sulphuric acid soln that the identical method of catholyte makes 30ml,, inject the anolyte compartment as anolyte;
The 3rd one-step electrolysis process
Electrolytic process carries out under normal temperature and pressure and negative electrode are added with condition with respect to a constant voltage of reference electrode, this constant voltage between-0.4～-0.6V between, the energising amount is every mol p-Nitromethoxybenzene 3～9F;
The 4th step aftertreatment
The catholyte that underpressure distillation was handled through the 3rd step is removed methyl alcohol and portion water, adds sodium bicarbonate, regulate pH value to 7～8 of catholyte, the toluene extraction, washing toluene extraction phase is removed inorganic salt wherein, dried over mgso, remove by filter sal epsom, toluene is removed in underpressure distillation, make the product Para-Anisidine, productive rate is between 13.8～63.3%.
Compare with background technology, the invention has the advantages that:
1, cleaning is finished redox reaction with the gain and loss of electronics, need not additional oxidizer and reductive agent.
2, organic synthesis carries out at normal temperatures and pressures, the reaction conditions gentleness.
3, reaction control easily, scale effect is little, and is particularly favourable to the production of fine chemical product.
Embodiment
Now further specify technical scheme of the present invention by embodiment.All embodiment operate according to the concrete operations step of described synthetic method fully.Each embodiment is only enumerated the gordian technique data of each step.
Embodiment one
In second step, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.3063g, close 0.00201mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.067mol, make catholyte, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.4V that the energising amount is 1164c, is equivalent to every mol p-Nitromethoxybenzene 6F; In the 4th step, yield is 40.7%.
Embodiment two
In second step, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.3063g, close 0.00201mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.067mol, make catholyte, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.5V that the energising amount is 1164c, is equivalent to every mol p-Nitromethoxybenzene 6F; In the 4th step, yield is 13.8%.
Embodiment three
In second step, the sulphuric acid soln of getting 22.5ml methyl alcohol and 7.5ml 2.0mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.3063g, close 0.00201mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.067mol, make catholyte, the sulphuric acid soln of getting 22.5ml methyl alcohol and 7.5ml 2.0mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.5V that the energising amount is 1164c, is equivalent to every mol p-Nitromethoxybenzene 6F; In the 4th step, yield is 63.3%.
Embodiment four
In second step, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 2.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.3063g, close 0.00201mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.067mol, make catholyte, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 2.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.5V that the energising amount is 1164c, is equivalent to every mol p-Nitromethoxybenzene 6F; In the 4th step, yield is 24.5%.
Embodiment five
In second step, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.3063g, close 0.00201mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.067mol, make catholyte, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.6V that the energising amount is 1164c, is equivalent to every mol p-Nitromethoxybenzene 6F; In the 4th step, yield is 45.0%.
Embodiment six
In second step, the sulphuric acid soln of getting 22.5ml methyl alcohol and 7.5ml 2.0mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.3063g, close 0.00201mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.067mol, make catholyte, the sulphuric acid soln of getting 22.5ml methyl alcohol and 7.5ml 2.0mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.5V that the energising amount is 582c, is equivalent to every mol p-Nitromethoxybenzene 3F; In the 4th step, yield is 28.3%.
Embodiment seven
In second step, the sulphuric acid soln of getting 22.5ml methyl alcohol and 7.5ml 2.0mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.3063g, close 0.00201mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.067mol, make catholyte, the sulphuric acid soln of getting 22.5ml methyl alcohol and 7.5ml 2.0mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.5V that the energising amount is 1746c, is equivalent to every mol p-Nitromethoxybenzene 9F; In the 4th step, yield is 48.7%.
Embodiment eight
In second step, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.5360g, close 0.00351mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.117mol, make catholyte, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.5V that the energising amount is 2032c, is equivalent to every mol p-Nitromethoxybenzene 6F; In the 4th step, yield is 39.2%.
Embodiment nine
In second step, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.0766g, close 0.00051mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.017mol, make catholyte, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.5V that the energising amount is 295c, is equivalent to every mol p-Nitromethoxybenzene 6F; In the 4th step, yield is 33.5%.
Embodiment ten
In second step, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, add p-Nitromethoxybenzene 0.3829g, close 0.00249mol, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.083mol, make catholyte, the sulphuric acid soln of getting 20ml methyl alcohol and 10ml 1.5mol/L is mixed into methyl alcohol-sulphuric acid soln of 30ml, as anolyte; In the 3rd step, constant voltage is-0.5V that the energising amount is 1442c, is equivalent to every mol p-Nitromethoxybenzene 6F; In the 4th step, yield is 42.6%.
Claims (1)
1. the electrochemical method for synthesizing of a Para-Anisidine is characterized in that, the concrete operations step:
The first step equipment is prepared
Described method needs to implement in the two chamber-type electrolyzer of separating with cationic exchange membrane, electrolyzer has two Room: cathode compartment and anolyte compartment, separate with cationic exchange membrane between two Room, copper sheet is made negative electrode, the ruthenium net is made anode, saturated calomel electrode is made reference electrode, with negative electrode and the reference electrode cathode compartment of packing into, with the anode anolyte compartment of packing into;
The preparation of the second one-step electrolysis liquid
Electrolytic solution divides catholyte and anolyte, the preparation catholyte, compound concentration is 0.5mol/L～2.5mol/L sulphuric acid soln, get methyl alcohol-sulphuric acid soln that methyl alcohol 20ml～22.5ml and above-mentioned sulphuric acid soln 10ml～7.5ml are mixed into 30ml, p-Nitromethoxybenzene is added methyl alcohol-sulphuric acid soln, add-on is 0.01～0.12mol/L, it is the p-Nitromethoxybenzene that every liter of methyl alcohol-sulphuric acid soln adds 0.01～0.12mol, make catholyte, inject cathode compartment, by preparing methyl alcohol-sulphuric acid soln that the identical method of catholyte makes 30ml,, inject the anolyte compartment as anolyte;
The 3rd one-step electrolysis process
Electrolytic process carries out under normal temperature and pressure and negative electrode are added with condition with respect to a constant voltage of reference electrode, this constant voltage between-0.4～-0.6V between, the energising amount is every mol p-Nitromethoxybenzene 3～9F;
The 4th step aftertreatment
The catholyte that underpressure distillation was handled through the 3rd step is removed methyl alcohol and portion water, adds sodium bicarbonate, regulate pH value to 7～8 of catholyte, the toluene extraction, washing toluene extraction phase is removed inorganic salt wherein, dried over mgso, remove by filter sal epsom, toluene is removed in underpressure distillation, make the product Para-Anisidine, productive rate is between 13.8～63.3%.
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- 2007-09-20 CN CNA2007100461811A patent/CN101187032A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102021567B (en) * | 2009-09-23 | 2012-10-03 | 沈阳大陆激光技术有限公司 | Nickel base alloy powder for manufacturing anticorrosive coating of boiler tube |
| CN102757402A (en) * | 2011-04-26 | 2012-10-31 | 北京化工大学 | Synthesizing method of 1,3,4-oxadiazole organic electroluminescent material |
| WO2020237793A1 (en) * | 2019-05-29 | 2020-12-03 | 武汉华星光电半导体显示技术有限公司 | Light-emitting layer dopant of organic light-emitting diode and preparation method therefor, and electroluminescent device |
| CN110656347A (en) * | 2019-10-24 | 2020-01-07 | 浙江大学 | Electroreduction preparation method of olanzapine intermediate |
| CN110656347B (en) * | 2019-10-24 | 2020-10-02 | 浙江大学 | Electroreduction preparation method of olanzapine intermediate |
| CN110747489A (en) * | 2019-11-07 | 2020-02-04 | 湖南大学 | Electroreduction preparation method of intermediate of anticancer drug gefitinib and analogue thereof |
| CN110747489B (en) * | 2019-11-07 | 2021-05-07 | 湖南大学 | Electroreduction preparation method of intermediate of anticancer drug gefitinib and analogue thereof |
| CN112593255A (en) * | 2020-12-10 | 2021-04-02 | 华东理工大学 | Electrochemical preparation method of p-aminophenyl-beta-hydroxyethyl sulfone |
| CN112593255B (en) * | 2020-12-10 | 2023-10-10 | 华东理工大学 | Electrochemical preparation method of p-aminophenyl-beta-hydroxyethyl sulfone |
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