CN110256294A - A kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride - Google Patents
A kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride Download PDFInfo
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- CN110256294A CN110256294A CN201910596267.4A CN201910596267A CN110256294A CN 110256294 A CN110256294 A CN 110256294A CN 201910596267 A CN201910596267 A CN 201910596267A CN 110256294 A CN110256294 A CN 110256294A
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- cyano
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
- C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C261/00—Derivatives of cyanic acid
- C07C261/04—Cyanamides
Abstract
The invention discloses a kind of techniques of continuous production N- cyano-ethyl acetimidate hydrochloride, the process of technique is as follows: in ethyl alcohol: acetonitrile: the molar ratio of hydrogen chloride is the ratio hybrid reaction of 1:0.8-2.5:0.8-3.0, isolated N- cyano-ethyl acetimidate hydrochloric acid product salt and containing hydrogen chloride acetonitrile liquid, when ethanol content is lower than 1% or less, acetonitrile solution is set to be back to absorbing reaction device entrance N- cyano-ethyl acetimidate hydrochloride and acetonitrile solution separation by separator.The present invention reduces scale of investment, save the cost, increases production capacity, save labor cost, reduce the advantages such as labor intensity, have preferable prospects for commercial application while promoting combined coefficient.
Description
Technical field
The present invention relates to technical field of chemical synthesis, more particularly to a kind of continuous production N- cyano-ethyleneimine
The technique of acid ethyl ester hydrochloride salt.
Background technique
Imidic acid carbethoxy hydrochloride is the important intermediate for preparing the drugs such as vitamin B1, Acetamiprid, is important foundation
Work raw material is widely used in the industries such as dyestuff, pharmacy, pesticide.
Technique using acetonitrile, ethyl alcohol, hydrogen chloride synthesis imidic acid carbethoxy hydrochloride is the technique generallyd use at present, it
Chemical equation it is as follows:
The problem of above-mentioned technique is primarily present is as follows:
(1), need to be added atent solvent chloroform, carbon tetrachloride, ether, petroleum ether, toluene, nitrobenzene, dioxy in industry
Azacyclohexane, ethylene glycol dimethyl ether, hexane equal solvent.The loss for just needing recycling design using organic solvent, causing solvent, and
Solvent usually affects to environment；
(2) according to the reaction mechanism of above-mentioned synthesis, to make reaction safety, steady progress, production technology is generallyd use at present
The production line of intermittent reaction, 1 set of Production Equipment of 2000 t Capacity Per imidic acid carbethoxy hydrochloride needs 1-5m3Reaction kettle about 30 is (containing catching up with gas
Kettle, drying kettle, at salt oven, crystallization kettle, hydrogen chloride absorption kettle), this does not only take up larger space, while in terms of resource and the energy
It is also a kind of waste.
(3) in entire production technology, need for concentrated hydrochloric acid and the concentrated sulfuric acid to be mixed to prepare dry hydrogen chloride gas participation
Reaction.After reaction, imidic acid ethyl ester salt crystal is separated with acetonitrile by the way of suction filtration, the meeting in decompression
There is a large amount of hydrogen chloride to parse, in order to not influence environment, ability after which needs to be adjusted with liquid alkaline or milk of lime
The requirement for reaching sewage discharge, it is all undesirable in terms of economy and the feature of environmental protection.
(4) by the limitation of drying and processing technique, the drying unit of normal pressure will cause N- cyano-ethanimidic acid second in production
The pyrolysis of ester hydrochloride causes product rotten, purity decline, the final quality for influencing product.
Therefore, overcome the shortcomings of the prior art, a kind of continuous production N- cyano-ethyl acetimidate hydrochloride is provided
Technique the problem of being those skilled in the art's urgent need to resolve.
Summary of the invention
In view of this, the present invention provides a kind of techniques of continuous production N- cyano-ethyl acetimidate hydrochloride.
To achieve the goals above, the present invention adopts the following technical scheme:
A kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride, the process of the technique are as follows:
In ethyl alcohol: acetonitrile: the ratio that the molar ratio of hydrogen chloride is 1:0.8-2.5:0.8-3.0 mixes above-mentioned substance anti-
It answers, isolated N- cyano-ethyl acetimidate hydrochloric acid product salt and containing hydrogen chloride acetonitrile liquid is lower than in ethanol content
When 1% or less, it is back to acetonitrile solution N- cyano-ethyl acetimidate hydrochloride and acetonitrile solution separation by separator
Absorbing reaction device entrance；
Specific step is as follows:
S1: the mode that the hydrogen chloride is ventilated is added in acetonitrile and is carried out instead in hydrogen chloride absorption reactor
It answers, while ethyl alcohol is added；
Substance after S2:S1 reaction, which is entered into salt slaking reaction device, to carry out into salt slaking reaction；
S3: the substance after S2 is reacted separates in the separator, obtains product type one, i.e. N- cyano-ethyleneimine
Acid ethyl ester hydrochloride salt wet product；
S4: the substance after S3 is separated passes through vacuum drying process, obtains product type two, i.e. N- cyano-ethanimidic acid
Ethyl ester dried salted products.
The ethyl alcohol in synthesis material can be replaced with into methanol in above-mentioned steps S1.
Further, for the hydrogen chloride in venting process, ventilation air is -5~10 DEG C, and duration of ventilation is 0.2~5h.
Further, it is -5~10 DEG C that temperature, which is added, in the ethyl alcohol, and the time for adding of ethyl alcohol is 1~30min.
Further, the reaction temperature of the salt-forming reaction is -20~55 DEG C, and the reaction time is 1~40min.
Further, the reaction temperature of the slaking reaction is 25~45 DEG C, and the reaction time is 0.5~3h.
Further, the technological parameter of the step S4 vacuum drying is as follows: vacuum degree be -0.1~
- 0.06MPa, drying temperature are 15-40 DEG C.
The invention also discloses a kind of continuous production devices, and stating continuous production device includes ethyl alcohol measuring tank, acetonitrile
Measuring tank, hydrogen chloride absorption tubular reactor, ethyl alcohol mixing tubular reactor；Slaking reaction kettle, crystallizing tank, separator, are also wrapped
Include acetonitrile circulating pump, ethyl alcohol feed pump, acetonitrile feed pump, hydrogen chloride acetonitrile mixer, ethyl alcohol mixer, crystallization feed pump, from
Scheming feed pump.
Preferably, the measuring tank, surge tank material can be Hastelloy, 904 stainless steels, in polytetrafluoroethylene (PTFE)
The materials such as lining, enamel, glass reinforced plastic.
Further, the hydrogen chloride absorption pipeline reactor and reacting pipe reactor refer to 1-1000 root pipe reaction
Device combination, the hydrogen chloride absorption microchannel or microchannel pipe reactor diameter are 0.1-20mm, length 50-12000mm,
1-10 sections of cooling devices are configured in the hydrogen chloride absorption pipeline reactor.
Preferably, the hydrogen chloride absorption pipeline reactor is 20-500 root canal road combination of reactors, and the hydrogen chloride is inhaled
It receives microchannel or microchannel reactor length is 100-8000mm.
Further, the hydrogen chloride absorption reactor be one of stirred autoclave or tubular reactor, it is described at
Salt reactor is one of stirred autoclave or tubular reactor, and the slaking reaction device is screw stirred autoclave.
Preferably, the hydrogen chloride absorption reactor and salt-forming reactor select tubular reactor.
Further, the separator includes but is not limited to centrifuge.
It can be seen via above technical scheme that compared with prior art, the present disclosure provides a kind of continuous production N-
Cyano-ethyl acetimidate hydrochloride technique.It is toxic organic molten that tetrachloromethane, benzene, toluene etc. is omitted in technique of the invention
Agent, reduce organic solvent separated with product, solvent recovery, effectively improve N- cyano-ethyl acetimidate salt
The combined coefficient of hydrochlorate, meanwhile, reduce the pollution for environment.
The present invention is also obviously improved synthesis N- cyano-ethyl acetimidate hydrochloride conjunction using microchannel reaction process
At efficiency, product selectivity and conversion ratio are improved.
From the aspect of technical process, absorb after the reaction hydrogen chloride acetonitrile can separate after recycle again as reaction
Object is recycled, and is reduced hydrogen chloride parsing, vent gas treatment, is reduced hydrogen chloride usage amount.Carrying out practical life
During productions, scale of investment, save the cost are reduced, increases production capacity, saves labor cost, reduces the advantages such as labor intensity,
With preferable prospects for commercial application.
Detailed description of the invention
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technical description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
The embodiment of invention for those of ordinary skill in the art without creative efforts, can also basis
The attached drawing of offer obtains other attached drawings.
Fig. 1 attached drawing is process flow chart provided by the invention；
Fig. 2 attached drawing is device connection figure provided by the invention.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
As shown in Figs. 1-2, the invention discloses a kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride,
The process of technique is as follows:
In ethyl alcohol: acetonitrile: the ratio that the molar ratio of hydrogen chloride is 1:0.8-2.5:0.8-3.0 mixes above-mentioned substance anti-
It answers, isolated N- cyano-ethyl acetimidate hydrochloric acid product salt and containing hydrogen chloride acetonitrile liquid is lower than in ethanol content
When 1% or less, it is back to acetonitrile solution N- cyano-ethyl acetimidate hydrochloride and acetonitrile solution separation by separator
Absorbing reaction device entrance；
Specific step is as follows:
S1: the mode that the hydrogen chloride is ventilated is added in acetonitrile and is carried out instead in hydrogen chloride absorption reactor
It answers, while ethyl alcohol is added, ventilation air is -5~10 DEG C, and duration of ventilation is 0.2~5h；Hydrogen chloride is described in venting process
It is -5~10 DEG C that temperature, which is added, in ethyl alcohol, the time for adding of ethyl alcohol is 1~
30min；
Substance after S2:S1 reaction, which is entered into salt slaking reaction device, to carry out into salt slaking reaction, salt-forming reaction it is anti-
Answering temperature is -20~55 DEG C, and the reaction time is 1~40min；The reaction temperature of slaking reaction is 25~45 DEG C, and the reaction time is
0.5~3h；
S3: the substance after S2 is reacted separates in the separator, obtains product type one, i.e. N- cyano-ethyleneimine
Acid ethyl ester hydrochloride salt wet product；
S4: the substance after S3 is separated passes through vacuum drying process, obtains product type two, i.e. N- cyano-ethanimidic acid
Ethyl ester dried salted products；The technological parameter of step S4 vacuum drying is as follows: vacuum degree is -0.1~-0.06MPa, and drying temperature is
15-40℃；
Continuous production device includes ethyl alcohol measuring tank -1, acetonitrile measuring tank -2, chlorination including stating continuous production device
Hydrogen absorbs tubular reactor -3, ethyl alcohol mixing tubular reactor -4；Slaking reaction kettle -5, crystallizing tank -6, centrifuge -7, acetonitrile follow
Ring pump -8, ethyl alcohol feed pump -9, acetonitrile feed pump -10, hydrogen chloride acetonitrile mixer -11, ethyl alcohol mixer -12, crystallization charging
Each device in pump -13, -14 continuous production device of centrifuge feed pump is acidproof, anti-chlorine ion material.
Hydrogen chloride absorption pipeline reactor and reacting pipe reactor refer to 1-1000 root canal road combination of reactors, the chlorine
Change hydrogen and absorb microchannel or microchannel pipe reactor diameter for 0.1-20mm, length 50-12000mm, the hydrogen chloride is inhaled
It receives and is configured with 1-10 sections of cooling devices in pipeline reactor.
Hydrogen chloride absorption reactor is one of stirred autoclave or tubular reactor, and the salt-forming reactor is stirring
One of reaction kettle or tubular reactor, the slaking reaction device are screw stirred autoclave.Separator includes but unlimited
In centrifuge.
In order to further prove that each factor has a significant effect for the yield of entire technique in the present invention, produce corresponding
Technical effect, applicant is by having carried out following confirmatory experiment:
Experiment one: influence experiment of the acetonitrile to yield
Experiment condition:
Embodiment 1-4 is ethyl alcohol: hydrogen chloride absorbs 0 DEG C of temperature, soak time 10min under conditions of molar ratio 1:2,
25 DEG C of reaction temperature, reaction time 30min, 45 DEG C of curing temperature, N- cyano-ethanimidic acid second is synthesized under the conditions of curing time 2h
Ester hydrochloride, N- cyano-ethyl acetimidate hydrochloride yield (using ethyl alcohol as standard) are as follows with the variation of acetonitrile molar ratio
Table 1:
Table 1
By the result of experiment one it is found that when the molar ratio of ethyl alcohol and acetonitrile is 1:1.5, N- cyano-ethyl acetimidate
Hydrochloride molar yield yield highest, up to 94.8%.
Experiment two: influence experiment of the hydrogen chloride to yield:
Experiment condition:
Embodiment 5-8 is in ethyl alcohol: acetonitrile absorbs 0 DEG C of temperature, soak time under conditions of molar ratio 1:1.5
25 DEG C of reaction temperature, reaction time 30min, 45 DEG C of curing temperature, it is sub- that N- cyano-second is synthesized under the conditions of curing time 2h by 10min
Amino acid carbethoxy hydrochloride, N- cyano-ethyl acetimidate hydrochloride yield (using ethyl alcohol as standard) is with hydrogen chloride molar ratio
Variation such as the following table 2:
Table 2
By the result of experiment two it is found that when the molar ratio of ethyl alcohol and hydrogen chloride is 1:1.5, N- cyano-ethanimidic acid second
Ester hydrochloride molar yield yield highest, up to 94.8%.
Experiment three: influence experiment of the temperature and time to yield is absorbed:
Experiment condition, in ethyl alcohol: acetonitrile: hydrogen chloride is under conditions of molar ratio 1:1.5:2, and 25 DEG C of reaction temperature, reaction
45 DEG C of curing temperature, N- cyano-ethyl acetimidate hydrochloride, N- cyano-are synthesized under the conditions of curing time 2h by time 30min
The yield (using ethyl alcohol as standard) of ethyl acetimidate hydrochloride is with the variation such as the following table 3 for absorbing temperature and time:
Table 3
By the result of experiment three it is found that being 0 DEG C when absorbing temperature, N- cyano-ethyl acetimidate hydrochloride molar yield
Yield highest, up to 94.8%.
Experiment four: the influence experiment of reaction temperature and time to yield
Experiment condition, in ethyl alcohol: acetonitrile: hydrogen chloride absorbs 0 DEG C of temperature, when absorption under conditions of molar ratio 1:1.5:2
Between 10min, 45 DEG C of curing temperature, N- cyano-ethyl acetimidate hydrochloride, N- cyano-second are synthesized under the conditions of curing time 2h
The yield (using ethyl alcohol as standard) of imidic acid carbethoxy hydrochloride with curing temperature and time variation such as the following table 4:
Table 4
By the result of experiment four it is found that when reaction temperature is 25 DEG C, reaction time 30min, N- cyano-ethanimidic acid second
Ester hydrochloride molar yield yield highest, up to 94.8%.
Experiment five: the influence experiment of curing temperature and time to yield.
Experiment condition, in ethyl alcohol: acetonitrile: hydrogen chloride absorbs 0 DEG C of temperature, when absorption under conditions of molar ratio 1:1.5:2
Between 10min, 25 DEG C of reaction temperature, N- cyano-ethyl acetimidate hydrochloride, N- cyano-are synthesized under the conditions of reaction time 30min
The yield (using ethyl alcohol as standard) of ethyl acetimidate hydrochloride with curing temperature and time variation such as the following table 5:
Table 5
By the result of experiment five it is found that when reaction temperature is 45 DEG C, reaction time 2.5h, N- cyano-ethanimidic acid second
Ester hydrochloride molar yield yield highest, up to 94.9%.
Experiment six: ethyl alcohol influences experiment to the yield of synthesis ethanimidic acid methyl esters:
Experiment condition, in methanol: acetonitrile: hydrogen chloride absorbs 0 DEG C of temperature, when absorption under conditions of molar ratio 1:1.5:2
Between 10min, 25 DEG C of reaction temperature, reaction time 30min, 45 DEG C of curing temperature, synthesize ethanimidic acid under the conditions of curing time 2h
Methyl ester hydrochloride, variation such as the following table 6 of ethanimidic acid methyl ester hydrochloride yield (using methanol as standard):
Table 6
By experiment six it is found that the effect of ethyl alcohol is better than methanol.
Each embodiment in this specification is described in a progressive manner, the highlights of each of the examples are with other
The difference of embodiment, the same or similar parts in each embodiment may refer to each other.For device disclosed in embodiment
For, since it is corresponded to the methods disclosed in the examples, so being described relatively simple, related place is said referring to method part
It is bright.
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention.
Various modifications to these embodiments will be readily apparent to those skilled in the art, as defined herein
General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, of the invention
It is not intended to be limited to the embodiments shown herein, and is to fit to and the principles and novel features disclosed herein phase one
The widest scope of cause.
Claims (10)
1. a kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride, which is characterized in that the process of the technique is such as
Under:
In ethyl alcohol: acetonitrile: the ratio that the molar ratio of hydrogen chloride is 1:0.8-2.5:0.8-3.0 divides above-mentioned substance hybrid reaction
From N- cyano-ethyl acetimidate hydrochloric acid product salt and containing hydrogen chloride acetonitrile liquid is obtained, it is lower than 1% or less in ethanol content
When, so that acetonitrile solution is back to absorption anti-N- cyano-ethyl acetimidate hydrochloride and acetonitrile solution separation by separator
Answer device entrance；
Specific step is as follows:
S1: the mode that the hydrogen chloride is ventilated is added in acetonitrile and is reacted in hydrogen chloride absorption reactor, together
When ethyl alcohol is added；
Substance after S2:S1 reaction, which is entered into salt slaking reaction device, to carry out into salt slaking reaction；
S3: the substance after S2 is reacted separates in the separator, obtains product type one, i.e. N- cyano-ethanimidic acid second
Ester hydrochloride wet product；
S4: the substance after S3 is separated passes through vacuum drying process, obtains product type two, i.e. N- cyano-ethyl acetimidate
Hydrochloric acid dried salted products.
2. a kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride according to claim 1, feature exist
In for the hydrogen chloride in venting process, ventilation air is -5~10 DEG C, and duration of ventilation is 0.2~5h.
3. a kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride according to claim 2, feature exist
In it is -5~10 DEG C that temperature, which is added, in the ethyl alcohol, and the time for adding of ethyl alcohol is 1~30min.
4. a kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride according to claim 3, feature exist
In the reaction temperature of the salt-forming reaction is -20~55 DEG C, and the reaction time is 1~40min.
5. a kind of synthetic method of continuous production N- cyano-ethyl acetimidate hydrochloride according to claim 4, special
Sign is that the reaction temperature of the slaking reaction is 25~45 DEG C, and the reaction time is 0.5~3h.
6. a kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride as claimed in claim 5, feature exist
In: the technological parameter of the step S4 vacuum drying is as follows: vacuum degree is -0.1~-0.06MPa, and drying temperature is 15-40 DEG C.
7. -6 any a kind of company of the technique of continuous production N- cyano-ethyl acetimidate hydrochloride according to claim 1
Continuousization production equipment, which is characterized in that the continuous production device includes ethyl alcohol measuring tank, acetonitrile measuring tank, hydrogen chloride suction
Receive pipeline reactor, ethyl alcohol mixing tubular reactor, slaking reaction kettle, crystallizing tank, separator, in the continuous production device
Each device be acidproof, anti-chlorine ion material.
8. a kind of continuous production device according to claim 7, which is characterized in that the hydrogen chloride absorption pipe reaction
Device and reacting pipe reactor refer to 1-1000 root canal road combination of reactors, the hydrogen chloride absorption microchannel or microchannel reaction
Device pipe diameter is 0.1-20mm, length 50-12000mm, and the hydrogen chloride absorption pipeline reactor is interior to be configured with 1-10 sections
Cooling device.
9. a kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride according to claim 8, feature exist
In the hydrogen chloride absorption reactor is one of stirred autoclave or tubular reactor, and the salt-forming reactor is stirring
One of reaction kettle or tubular reactor, the slaking reaction device are screw stirred autoclave.
10. a kind of technique of continuous production N- cyano-ethyl acetimidate hydrochloride according to claim 9, feature
It is, the separator includes but is not limited to centrifuge.
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Cited By (1)
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| CN112898183A (en) * | 2021-01-25 | 2021-06-04 | 宁夏东吴农化股份有限公司 | Method for synthesizing cyanoethyl ester by base catalysis in microchannel reactor |
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Application publication date: 20190920 |
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