CN107793328A - A kind of production method of N, N cyanoethyl benzylaniline - Google Patents
A kind of production method of N, N cyanoethyl benzylaniline Download PDFInfo
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- CN107793328A CN107793328A CN201610768588.4A CN201610768588A CN107793328A CN 107793328 A CN107793328 A CN 107793328A CN 201610768588 A CN201610768588 A CN 201610768588A CN 107793328 A CN107793328 A CN 107793328A
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- cyanoethyl
- benzylaniline
- binding agent
- production method
- acid binding
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Abstract
The invention provides a kind of N, the production method of N cyanoethyl benzylanilines, comprises the following steps：(1) N cyanoethyl anilines, benzyl chloride and phase transfer catalyst A are put into reactor under DCS system control, fed back after heating according to the change of pH in reaction system, automatically control the addition of acid binding agent, the pH for controlling reaction system is 4~9, until reaction terminates, material I is obtained；(2) material I obtained in step (1) is gone in the pre- dilution kettle added with diluted hydrochloric acid aqueous solution, acid binding agent regulation system pH is added after cooling to neutrality, product N, N cyanoethyl benzylaniline is isolated after filtered washing, and collects chlorate mother liquor；(3) chlorate mother liquor condensing crystallizing after activated carbon decolorizing obtains chlorination salt crystal, Water Sproading caused by concentration.This method realizes Automated condtrol using DCS system, and caused mother liquid coming reclaims chlorate by condensing crystallizing and carries out recycling, reduces cost, flow is succinct, suitable for industrially popularization and application.
Description
Technical field
The present invention relates to DYE PRODUCTION technical field, and in particular to the production method of a kind of N, N- cyanoethyl benzylaniline.
Background technology
N, N- cyanoethyl benzylaniline are white powders, 97.2~102.3 DEG C of fusing point.N, N- cyanoethyl benzylaniline are one
Individual important organic intermediate, is widely used in the synthesis of agricultural chemicals, dyestuff etc..China manufacturer it is less, rely primarily on from
The U.S., Japan and other countries import, N, N- cyanoethyls benzylaniline have good prospect and huge economic benefit in China.
Wang Qi (《Dyestuff and dyeing》, the technical study of N- cyanoethyls-Phenhenzamine, 1992 (4):20-21) disclose
One kind prepares N, the method for N- cyanoethyl benzylanilines, including：Added into the 250ml three-necked flasks equipped with reflux condensing tube
40ml water and 74.8g N- cyanoethyl anilines, are warming up to 90~100 DEG C, while instill 67.8g benzyl chlorides and 20% sodium carbonate
Solution.It is added dropwise, is reacted 3 hours at 90~100 DEG C, add glacial acetic acid, stirring, and be slowly cooled to 30 DEG C, now separates out
White solid, filtering, washing obtain finished product.In its method post processing need to add glacial acetic acid so that in mother liquid coming containing sodium acetate,
The many kinds of substance such as sodium chloride, post-processing difficulty is added, in addition, exhaust carbon dioxide can be produced in course of reaction.It is above-mentioned
Sodium carbonate once puts into excess in method, and a part of benzyl chloride and N- cyanoethyl aniline may be lost in reaction.
Publication No. CN1036974A Chinese invention patent document discloses a kind of N, N- cyanoethyl benzylaniline dyestuffs
Manufacture method, be directed to a kind of N, the manufacture method of N- cyanoethyl benzylanilines, including：In non-organic solvent medium,
N- cyanoethyl anilines and benzyl chloride are subjected to melting reaction at 80~130 DEG C, water mashing is added, hydroxide is added after cooling
Sodium, then by filtering, washing, dry and obtain N, N- cyanoethyl benzylanilines, yield is about 85~92%.This method was reacted
Product hydrochloric acid is constantly enriched with journey, and system pH is in highly acid, and so as to cause reaction incomplete, yield is relatively low.
Patent documents above does not refer to the post processing of mother liquid coming caused by the reaction, if directly discharging, salt in mother liquid coming
Divide content high and chlorion is to the toxic effect of bacterium, can have a strong impact on that the purification of the biological treatment system in sewage disposal is imitated
Fruit.
At present, the big production technology of N, N- cyanoethyl benzylaniline is to add a certain amount of bottom water in a kettle, then
Sequentially add N- cyanoethyl anilines, soda ash.After covering people's lid, benzyl chloride, slow more than 20 individual hour of temperature reaction are passed through, then beat
People's lid is opened, is diluted with water, pump treats that centrifuge filters to transfer tank after cooling.Its shortcoming is that the blowing that feeds intake uses manual operation,
React, be diluted in operation in a kettle, production efficiency is relatively low, while thinned water amount is larger.
Therefore, technique can be simplified by finding one kind, reduce cost, reduce wastewater flow rate, at the same mother liquid coming can unification processing,
And realize that the synthesis technique of utilization of wastewater resource turns into the focus of current research.
The content of the invention
It is an object of the invention to provide a kind of N, the clean and effective automatic production method of N- cyanoethyl benzylanilines, with letter
Chemical industry skill, production cost is reduced, reduce wastewater flow rate and realize the recycling of waste water.
The production method of a kind of N, N- cyanoethyl benzylaniline, comprises the following steps：
(1) N- cyanoethyl anilines, benzyl chloride and phase transfer catalyst A are put into reactor under DCS system control, risen
Being fed back after temperature according to the change of pH in reaction system, automatically control the addition of acid binding agent, the pH for controlling reaction system is 4~9,
Until reaction terminates, material I is obtained；
(2) material I obtained in step (1) is gone in the pre- dilution kettle added with diluted hydrochloric acid aqueous solution, added after cooling
Acid binding agent regulation system pH isolates product N, N- cyanoethyl benzylaniline, and collect chlorate to neutrality after filtered washing
Mother liquor；
(3) chlorate mother liquor condensing crystallizing after activated carbon decolorizing obtains chlorination salt crystal, Water Sproading caused by concentration.
The technical program realizes Automated condtrol using DCS system, reduces cost, and caused mother liquid coming passes through condensing crystallizing
Reclaim chlorate and carry out recycling, water caused by concentration is as the thinned water in course of reaction and slurry circulation profit
With realizing the zero-emission of waste water, flow is succinct, suitable for industrially popularization and application.
In step (1), the temperature of the reaction system is 70~120 DEG C.Preferably, the temperature of the reaction system is
80~105 DEG C.In course of reaction, temperature and steam, the cooling sea water regulating valve interlocked control of reaction system, reaction is set to maintain all the time
In required reaction temperature.
In step (1), the soaking time of the reaction is 5~15h.Due to adding phase transfer catalyst A so that raw material N-
Cyanoethyl aniline contacts in water solution system relatively more abundant with benzyl chloride.It is used in particular with the progress of reaction
Acid binding agent amount is more and more, and the aqueous phase of acid binding agent entrainment is more and more, and raw material organic phase N- cyanoethyl anilines in reaction system,
Benzyl chloride is constantly reduced, and in the case where there is phase transfer catalyst A effects, raw material N- cyanoethyl anilines are relative with benzyl chloride intermolecular contacts
Be more prone to without catalyst action so that reaction can comparatively fast carry out, preferably, the soaking time of the reaction be 5~
10h。
The mol ratio of the N- cyanoethyl anilines, benzyl chloride and acid binding agent (meter of folding hundred, as follows) is 1：0.95~1.03：
0.90~1.10.Due to adding phase transfer catalyst in reaction system, be dissolved in N- cyanoethyl anilines in reaction system with
Benzyl chloride mol ratio is about 1:1, simultaneous reactions system is controlled 4~9, it is possible to prevente effectively from the generation of accessory substance, to enter one
Step reduces consumption of raw materials, production cost is reduced, preferably, the mol ratio of the N- cyanoethyl anilines, benzyl chloride and acid binding agent
For 1：0.98~1.02：0.95~1.05.
The acid binding agent is at least one of ammoniacal liquor, liquid caustic soda and carbonate aqueous solution.The acid binding agent can be thrown in batches
Add, to reduce the hydrolysis of benzyl chloride；If from piece alkali, the soda ash of solid-state, or the ammoniacal liquor that concentration is higher, inconvenience adds in batches,
All being added before reaction can cause reaction system pH too strong so that benzyl chloride hydrolyzes.
Preferably, the acid binding agent is ammoniacal liquor.Using ammoniacal liquor as acid binding agent, only introduced in reaction system ammonium root from
Son, avoid introducing new impurity, make waste water unification disposable.
The phase transfer catalyst A is at least one in tetramethyl ammonium chloride, etamon chloride and 4-propyl ammonium chloride
Kind.
The dosage of the phase transfer catalyst A is the 0.3~1.1% of N- cyanoethyl aniline quality.It is preferably, described
Phase transfer catalyst A dosage is the 0.5% of N- cyanoethyl aniline quality.
The measuring tank of the N- cyanoethyl anilines, benzyl chloride and acid binding agent carries Weighing module, wherein, N- cyanoethyl benzene
Stop valve is provided with below amine, the measuring tank of benzyl chloride and acid binding agent and reactor bottom valve, is additionally provided with below the measuring tank of acid binding agent
Regulating valve.
In step (1), reaction system under strongly acidic conditions, hydrochloric acid caused by reaction easily with N- cyanoethyl anilines, N, N- cyanogen
Ethylbenzylaniline forms ammonium salt, so that reaction is difficult to be carried out toward positive reaction direction.And once system alkalescence is too strong, then chlorine
Change benzyl and be easily hydrolyzed into benzylalcohol, therefore reaction system pH controls are 4~9.To cause reaction can be quickly toward positive reaction side
To progress, avoid the loss of raw material again, therefore, reaction system pH as far as possible between faintly acid and alkalescent, preferably,
The pH of described reaction system is 6~8.
In course of reaction, the pH of reaction system and the regulating valve of acid binding agent are interlocked, and acid is tied up by computer Online Monitoring Control
The addition of agent.Computer is according to real-world effectiveness kettle pH change feedback and the setting of computer program, by controlling acid binding agent to adjust
The aperture for saving valve controls the addition of acid binding agent so that reaction system pH is maintained between 4~9.If reaction system pH is low
In the pH lower limits of setting, then acid binding agent regulating valve is automatically turned on, acid binding agent is slowly added dropwise into reactor, acid binding agent charging is adjusted
Saving the aperture of valve can be adjusted according to the degree of closeness of pH display numerical value and setting value, once reach the pH higher limits set
Just acid binding agent regulating valve and Feed Shut-Off valve are automatically turned off simultaneously.
Preferably, the adition process of acid binding agent also can be by setting acid binding agent in DCS control systems in step (1)
Quantity is added to complete.After operation interface presets the addition quantity of acid binding agent, acid binding agent regulating valve and stop valve just simultaneously from
It is dynamic to open, soon automatically turned off after the numerical value that acid binding agent addition reaches setting.
In step (2), the diluted hydrochloric acid aqueous solution in the dilution kettle is prepared by adding hydrochloric acid and bottom water, wherein, hydrochloric acid
Dosage be bottom water quality 10%.
In step (2), it is described dilution kettle in diluted hydrochloric acid aqueous solution accentuation for the mass of material I 58~
68%.
In step (3), before the chlorate mother liquor is decolourized, liquefied ammonia, ammoniacal liquor or piece alkali regulation system pH to 8 need to be used
~10.
In step (3), the dosage of the activated carbon is the 0.1~0.3% of chlorate mother liquor quality, and adsorption time is
2h。
In step (3), Water Sproading caused by concentration is as reaction thinned water or slurry.
Course of reaction carries out Automated condtrol using DCS system.Wherein, raw material N- cyanoethyl anilines, benzyl chloride and acid is tied up
The operation such as the control of the input, reaction temperature of agent and the dilution of product, discharging is all completed by DCS control systems.
Compared with prior art, the present invention has the advantages that：
(1) feed intake, the operation such as blowing is completed by DCS control systems, realize the automation of Workshop Production, simplify
Production technology, production efficiency is improved, reduce cost of labor.
(2) in automated system of the invention, the pH of reaction system and the regulating valve of acid binding agent interlock so that reaction is all the time
It is maintained in the range of the pH of stabilization, rapid reaction can be promoted to carry out, makes the reaction of raw material N- cyanoethyl anilines complete, can have again
Effect avoids the loss of benzyl chloride, can reduce by 2~5% benzyl chloride dosage, reduce production cost, realizes the efficient steady of reaction
Fixed production.
(3) in present invention process, reaction reduces the holding time of reactor, without waiting material with diluting separate operation
Dilute the complete production capacity that just can again feed intake, substantially increase workshop of blowing；At the same time, diluted using dilute hydrochloric acid solution,
The purity of product can improve at least 4%.
(4) present invention adds catalyst A, accelerates reaction process, effectively shortens the single batch materials production time, so as to enter one
Step reduces production cost, improves production efficiency.
(5) caused mother liquid coming reclaims chlorate by condensing crystallizing and carries out recycling, the chlorine purified out in reacting
Salt dissolving crystal can add economic benefit, water is as the thinned water in course of reaction and washing caused by concentration with export trade
With water circulation use, the zero-emission of waste water is realized, reaches clean manufacturing, the purpose of energy-saving and emission-reduction.
Brief description of the drawings
Fig. 1 is the N that the embodiment of the present invention uses, and the reaction unit of the automatic production method of N- cyanoethyl benzylanilines is simple
Figure；
The N that Fig. 2 uses for the embodiment of the present invention, the technological process of the automatic production method of N- cyanoethyl benzylanilines
Figure.
Embodiment
The N, reaction unit figure such as Fig. 1 of the automatic production method of N- cyanoethyl benzylanilines that the embodiment of the present invention uses
It is shown.
The N, process chart such as Fig. 2 of the automatic production method of N- cyanoethyl benzylanilines that the embodiment of the present invention uses
It is shown.
Embodiment 1
(1) in 20m3Input N- cyanoethyl anilines (purity 96.2%) 2660Kg and tetramethyl ammonium chloride in reactor
13.3Kg, 50 DEG C are warming up to, add the benzyl chloride 2310Kg measured, be to slowly warm up to 100 DEG C of insulations, pass through during heating
DCS system operation adds ammoniacal liquor (mass fraction 20%) 1540Kg stage by stage, and reaction system pH is between 5~7 for control.Insulation
After 4 hours, start, using high performance liquid chromatography sampling detection, to control raw material N- cyanoethyl aniline Han Liang≤3%.Soaking time
Reaction in 6 hours can reach terminal.
(2) after qualified after testing, bottom water 4000Kg and concentrated hydrochloric acid 400Kg is added in dilution kettle, stirring is opened, is warming up to 70
After DEG C, reactor bottom valve is opened, a collection of qualified material is released from reactor, crystallisation by cooling, treats that temperature is down to less than 45 DEG C, adds
Enter ammoniacal liquor (mass fraction 20%) 480Kg regulation systems pH to 7.1, pump is filtered to centrifuge, is isolated after washing
N, N- cyanoethyl benzylaniline product (yield 97.8%, purity 97.5%) and ammonium chloride mother liquor water.
(3) ammoniacal liquor is added in ammonium chloride mother liquor water, regulation pH value is 9, after adding activated carbon decolorizing absorption, filters out work
Property charcoal obtain ammonium chloride solution, then obtain ammonia chloride crystal by condensing crystallizing, concentration condensing hot air furnace is used to dilute or wash
Wash.
Embodiment 2
(1) in 20m3Input N- cyanoethyl anilines (purity 96.8%) 2660Kg and etamon chloride in reactor
13.3Kg, 60 DEG C are warming up to, add the benzyl chloride 2350Kg measured, be to slowly warm up to 90 DEG C of insulations, pass through DCS during heating
System operatio adds liquid caustic soda (mass fraction 30%) 2430Kg stage by stage, and reaction system pH is between 6~7 for control.It is small to be incubated 5
Shi Hou, start using high performance liquid chromatography sampling detection, control raw material N- cyanoethyl anilines are containing amount≤3%.Soaking time 6.5
Hour reaction can reach terminal.
(2) after qualified after testing, bottom water 4000Kg and concentrated hydrochloric acid 400Kg is added in dilution kettle, stirring is opened, is warming up to 70
After DEG C, reactor bottom valve is opened, a collection of qualified material is released from reactor, crystallisation by cooling, treats that temperature is down to less than 45 DEG C, adds
Enter liquid caustic soda (mass fraction 30%) 460Kg regulation systems pH to 7.6, pump is filtered to centrifuge, is isolated after washing
N, N- cyanoethyl benzylaniline product (yield 97.2%, purity 96.5%) and sodium chloride mother liquid coming.
(3) piece alkali is added in sodium chloride mother liquid coming, regulation pH value is 10, after adding activated carbon decolorizing absorption, is filtered out
Activated carbon obtains sodium chloride solution, then obtains sodium chloride crystal by condensing crystallizing, and the concentrated mother liquor water isolated collects conduct
Corresponding acid binding agent, concentration condensing hot air furnace are used to dilute or wash.
Embodiment 3
(1) in 20m3Input N- cyanoethyl anilines (purity 96%) 2660Kg and 4-propyl ammonium chloride in reactor
26.6Kg, 55 DEG C are warming up to, add the benzyl chloride 2300Kg measured, be to slowly warm up to 95 DEG C of insulations, pass through DCS during heating
System operatio adds aqueous sodium carbonate (mass fraction 60%) 1660Kg stage by stage, control reaction system pH 7~8 it
Between.After insulation 5 hours, start, using high performance liquid chromatography sampling detection, to control raw material N- cyanoethyl aniline Han Liang≤3%.
Soaking time reaction in 6 hours can reach terminal.
(2) after qualified after testing, bottom water 4000Kg and concentrated hydrochloric acid 400Kg is added in dilution kettle, stirring is opened, is warming up to 70
After DEG C, reactor bottom valve is opened, a collection of qualified material is released from reactor, crystallisation by cooling, treats that temperature is down to less than 45 DEG C, carbon
Acid sodium aqueous solution (mass fraction 60%) 300Kg regulation systems pH to 7.3, pump is filtered to centrifuge, is divided after washing
Separate out N, N- cyanoethyl benzylanilines product (yield 97.1%, purity 96.5%) and sodium chloride mother liquid coming.
(3) piece alkali is added in sodium chloride mother liquid coming, regulation pH value is 10, after adding activated carbon decolorizing absorption, is filtered out
Activated carbon obtains sodium chloride solution, then obtains sodium chloride crystal by condensing crystallizing, and the concentrated mother liquor water isolated collects conduct
Corresponding acid binding agent, concentration condensing hot air furnace are used to dilute or wash.
Comparative example 1
Respectively feed intake same as Example 3, difference is, in step (1), puts into bottom water 2500Kg and N- cyanogen in a kettle
It is disposable to put into soda ash 1100Kg after MEA, phase transfer catalyst A is not added, is started to warm up after putting into benzyl chloride to 105
DEG C insulation.As a result find to need insulation 13h reactions to can be only achieved terminal.
In step (2), it is diluted in kettle is diluted without diluted hydrochloric acid aqueous solution, but bottom water 8000Kg is diluted,
Centrifuged to obtain N, N- cyanoethyls benzylaniline and sodium chloride mother liquid coming, product yield 96.4% after cooling, purity is
93.2%.
Using the feeding mode of comparative example, plus heating and heat preservation reaction time and finishing time, a collection of product is produced
26 hours are at least needed, production efficiency is relatively low.Its yield, purity are also below embodiment 3.
From above-described embodiment and comparative example, can be improved using the inventive method while product purity is improved
The yield of product.Meanwhile by adding phase transfer catalyst A addition and DCS utilization, when effectively shortening single batch reaction
Between, improve production efficiency.And the recycling of mother liquid coming then realizes the purpose of energy-saving and emission-reduction.
Claims (10)
1. the production method of a kind of N, N- cyanoethyl benzylaniline, it is characterised in that comprise the following steps：
(1) N- cyanoethyl anilines, benzyl chloride and phase transfer catalyst A are put into reactor under DCS system control, after heating
Being fed back according to the change of pH in reaction system, automatically control the addition of acid binding agent, the pH for controlling reaction system is 4~9, until
Reaction terminates, and obtains material I；
(2) material I obtained in step (1) is gone in the pre- dilution kettle added with diluted hydrochloric acid aqueous solution, is added after cooling and tie up acid
Agent regulation system pH isolates product N, N- cyanoethyl benzylaniline, and collect chlorate mother liquor to neutrality after filtered washing；
(3) chlorate mother liquor condensing crystallizing after activated carbon decolorizing obtains chlorination salt crystal, Water Sproading caused by concentration.
2. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that described in step (1)
The temperature of reaction system is 70~120 DEG C.
3. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that the insulation of the reaction
Time is 5~10h.
4. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that the acid binding agent is ammonia
At least one of water, liquid caustic soda and carbonate aqueous solution.
5. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that the N- cyanoethyls benzene
The mol ratio of amine, benzyl chloride and acid binding agent is 1：0.95~1.03：0.90~1.10.
6. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that the phase transfer catalysis (PTC)
Agent A is at least one of tetramethyl ammonium chloride, etamon chloride and 4-propyl ammonium chloride.
7. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that the phase transfer catalysis (PTC)
Agent A dosage is the 0.3~1.1% of N- cyanoethyl aniline quality.
8. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that the N- cyanoethyls benzene
The measuring tank of amine, benzyl chloride and acid binding agent carries Weighing module, wherein, the metering of N- cyanoethyl anilines, benzyl chloride and acid binding agent
Stop valve is provided with below groove and reactor bottom valve, regulating valve is additionally provided with below the measuring tank of acid binding agent.
9. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that in course of reaction, instead
The pH of system and the regulating valve of acid binding agent, stop valve interlocked control are answered, passes through the addition of computer Online Monitoring Control acid binding agent.
10. the production method of N as claimed in claim 1, N- cyanoethyl benzylaniline, it is characterised in that course of reaction uses
DCS system carries out Automated condtrol.
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| CN115536548A (en) * | 2022-10-10 | 2022-12-30 | 浙江亿得新材料股份有限公司 | Environment-friendly intermediate synthesis method |
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| CN111056974A (en) * | 2019-12-31 | 2020-04-24 | 烟台安诺其精细化工有限公司 | Preparation method of N-cyanoethyl-N-phenethylaniline |
| CN111205201A (en) * | 2020-01-22 | 2020-05-29 | 浙江迪邦化工有限公司 | Method and system for producing N-cyanoethyl-N-benzylaniline |
| CN111205201B (en) * | 2020-01-22 | 2022-09-20 | 浙江迪邦化工有限公司 | Method and system for producing N-cyanoethyl-N-benzylaniline |
| CN115536548A (en) * | 2022-10-10 | 2022-12-30 | 浙江亿得新材料股份有限公司 | Environment-friendly intermediate synthesis method |
| CN115536548B (en) * | 2022-10-10 | 2023-09-12 | 浙江亿得新材料股份有限公司 | Environment-friendly synthesis method of intermediate |
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