CN110256295A - The synthetic method of N- cyan ethyl ethylimidoote - Google Patents
The synthetic method of N- cyan ethyl ethylimidoote Download PDFInfo
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- CN110256295A CN110256295A CN201910596272.5A CN201910596272A CN110256295A CN 110256295 A CN110256295 A CN 110256295A CN 201910596272 A CN201910596272 A CN 201910596272A CN 110256295 A CN110256295 A CN 110256295A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C261/00—Derivatives of cyanic acid
- C07C261/04—Cyanamides
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Abstract
The invention discloses a kind of synthetic methods of N- cyan ethyl ethylimidoote, it comprises the following steps that and ethyl acetimidate hydrochloride is added in the reaction kettle with stirring, cyanamide aqueous solution is added under stirring, stirring to ethyl acetimidate hydrochloride is sufficiently dissolved；Alkaline matter is added dropwise and adjusts pH value；React material sufficiently, every 10min sampling is primary during the reaction, and sample is detected by chromatography, determines the conversion ratio of reaction；After standing the water phase and organic phase layering into reactant, N- cyan ethyl ethylimidoote product is can be obtained in vacuum distillation after organic phase is extracted out.The problems such as technical solution of the present invention simple possible, energy conservation and environmental protection solves and reacts complicated in synthesis process, generates pollution, while having saved cost.
Description
Technical field
The present invention relates to technical field of organic synthesis, more particularly to a kind of conjunction of N- cyan ethyl ethylimidoote
At method.
Background technique
Cyanaoethyl methacrylate is called the important doctor that N- cyan ethyl ethylimidoote is synthetic pesticide Acetamiprid and vitamin B1
Medicine, pesticide intermediate, are also important industrial chemicals.
Domestic many documents are all described the synthesis of cyanaoethyl methacrylate, and what is mainly used at present synthesizes the anti-of cyanaoethyl methacrylate
Answer equation as follows:
The reaction process the main problems are as follows:
1, since the price of raw material disodium hydrogen phosphate is higher, cause production cost higher；
2, contain a large amount of sodium dihydrogen phosphate, sodium chloride, ammonium chloride in the by-product generated, this part salt-mixture is listed in
In dangerous waste register, when subsequent processing, is difficult separating-purifying, larger to environmental hazard；
3, the reaction time is 4-12 hours or so in production process, and reaction temperature is at 40 DEG C or more, required energy consumption height, time
It is long；
4, the content of cyanaoethyl methacrylate is 85% or so in product organic layer in above-mentioned reaction process, and purity is lower, and total
For yield in 60-70%, yield is relatively low.
Therefore it provides a kind of yield is high, less energy consumption, the synthetic method of the N- cyan ethyl ethylimidoote of simple process is this
The problem of field technical staff's urgent need to resolve.
Summary of the invention
It is yield, pure in view of this, it is an object of the invention to overcome production cost existing in the prior art, energy consumption high
Low, the problems such as by-product is difficult is spent, a kind of high and low energy consumption of yield and a kind of single N- cyano ethyleneimine of by-product are provided
The synthetic method of acetoacetic ester.
To achieve the goals above, the present invention adopts the following technical scheme:
The synthetic method of N- cyan ethyl ethylimidoote, which is characterized in that the synthesis step is as follows:
S1, mixing: ethyl acetimidate hydrochloride is added in the reaction kettle for having turned on stirring, and control mixing speed exists
150-200r/min prevents ethyl acetimidate hydrochloride overcharge from killing stirring and is unable to operate normally, in stirring shape
Cyanamide aqueous solution is added under state, comes into full contact with solid-liquid two-phase and ethyl acetimidate hydrochloride is completely dissolved and is accelerated instead
It answers, stirring does not stop until reaction terminates；
S2, it adjusts pH value: adjusting pH value to 5-9 in the mixed solution and dripping alkaline matter that S1 is obtained, temperature control exists
Within 25 DEG C；
S3, reaction: react material sufficiently in the state that 20-40 DEG C of room temperature, mixing speed are 300r/min, when reaction
Between be 10-90min；
S4, detection: after above-mentioned reaction starts, sampling once at interval of 10min, and sample is detected by chromatography, is determined
When the conversion ratio of reaction reaches 99%, stop reaction；
S5, separation: stop stirring after the conversion ratio of above-mentioned reaction is stablized, stand water phase and organic phase into reactant
After layering, after organic phase is extracted out vacuum degree be -0.085MPa, temperature be 110 DEG C of vacuum distillations N- cyano second can be obtained
Imidic acid ethyl ester product, remaining water phase are -0.085MPa in vacuum degree through multi-effect evaporator, and temperature is that 80 DEG C of concentration and separation are
Water and ammonium chloride can be obtained.
By using above-mentioned technical proposal, beneficial effects of the present invention are as follows: the reaction kettle that the present invention discloses stirring is main
It is to prevent from killing stirring, cyanamide is added under stirring can make the two contact rapidly, when accelerating reaction, and preventing process here
Between it is too long, prevent cyanamide rotten.Present invention process step is simple, is more convenient to operate.
Further, the molar ratio of ethyl acetimidate hydrochloride and cyanamide is 1:0.8-1.2 in the step S1.
Further, the mass percent concentration of cyanamide aqueous solution is 25-50% in the step S1.
Further, the charge temperature of cyanamide aqueous solution is 0-10 DEG C in the step S1.
Further, in the step S2, alkaline matter is that mass percent concentration is 10-50% sodium hydrate aqueous solution
Or mass percent concentration is 10-25% ammonium hydroxide.
It can be seen via above technical scheme that compared with prior art, it is sub- that the present disclosure provides a kind of N- cyano second
The synthetic method of amino acid ethyl ester, reaction equation are as follows:
It is different from the prior art, raw material only needs cyanamide and ethyl acetimidate hydrochloric acid in this reaction, does not need addition phosphorus
The buffers such as sour disodium hydrogen, sodium dihydrogen phosphate, ammonium phosphate and stabilizer, pair can be made by making catalyst using sodium hydroxide or ammonium hydroxide
Product unification is conducive to the content for improving by-product, reduces the type of by-product, avoid the feelings that by-product can not separate
Condition；
Since cyanogenation temperature can react at normal temperature in the present invention, energy consumption is reduced；Meanwhile when of the invention reaction
Between by original 4-12h it is short be 30min-90min, have apparent variation, substantially reduce production time and labour cost.
N- cyan ethyl ethylimidoote, compared with literature procedure, product content are synthesized using technical solution of the present invention
Height, the content of cyanaoethyl methacrylate is up to 95% or more in obtained organic layer, and total recovery is 80% or more；
Since sodium hydroxide or ammonium hydroxide are only used as catalyst and adjust pH value, dosage is seldom, is only used as catalyst and adds
Enter 0.5-5%, the content for generating side product chlorinated sodium or ammonium chloride is 98-99% or more, can be recycled completely；
It additionally needs, it is emphasized that the present invention is other than above-mentioned technical effect, also significantly reduces production cost, this field
Well known to personnel, the cost of every gram of the disodium hydrogen phosphate used in the prior art is up to hundred yuan, so by changing original system
Standby mode, hence it is evident that reduce product price, can widely be applied to every field.
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.
Attached drawing 1 is the gas phase spectrogram that N- cyan ethyl ethylimidoote crude product is synthesized in the embodiment of the present invention 1, synthesizes crude product cyanogen
The content of base ethyl ester are as follows: 97.2%；
Attached drawing 2 is the gas phase spectrogram that N- cyan ethyl ethylimidoote crude product is synthesized in the embodiment of the present invention 6, synthesizes crude product cyanogen
The content of base ethyl ester are as follows: 91.2%；
Attached drawing 3 is using disodium hydrogen phosphate as catalyst, and reaction temperature is 40 DEG C, other reaction conditions and phase in embodiment 1
With the gas phase spectrogram of prepared N- cyan ethyl ethylimidoote crude product, the content of crude product cyanaoethyl methacrylate is synthesized are as follows: 88.1%, explanation
To the synthesis of cyanaoethyl methacrylate, there is no the content synthesized by the present invention is high after adding catalyst disodium hydrogen phosphate；
Attached drawing 4 is the gas phase spectrogram in the embodiment of the present invention 1 after the distillation of synthesis N- cyan ethyl ethylimidoote, cyanaoethyl methacrylate
Content are as follows: 99.8%.
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.
Embodiment 1:
Ethyl acetimidate hydrochloride 505.1g is added in the reaction kettle with stirring, quality is added under stirring
The cyanamide aqueous solution 544.0g that concentration is 30%, stirring make ethyl acetimidate hydrochloride after completely dissolution in 3 minutes, start to drip
Adding mass percent concentration is 30% sodium hydrate aqueous solution, adjusts the pH value of solution in reaction kettle to 6.5 or so, anti-under room temperature
After answering 60min, organic phase is taken to do gas chromatographic analysis, the content of cyanaoethyl methacrylate are as follows: 97.2%.
System after reaction waits for pouring into that separatory funnel is static makes its layering under room temperature, and lower layer is water phase, and upper layer is organic phase,
The N- cyan ethyl ethylimidoote product of high-purity can be obtained in organic phase after being evaporated under reduced pressure, cyanaoethyl methacrylate in final product
Content are as follows: 99.8%, total recovery: 83%；The remaining water phase of lower layer obtains water and chlorination after multi-effect evaporator is concentrated and separated
Ammonium, water can return to for producing, and ammonium chloride can be used as by-product sale.
Embodiment 2:
Ethyl acetimidate hydrochloride 505.1g is added in the reaction kettle with stirring, quality is added under stirring
The cyanamide aqueous solution 524.1g that concentration is 25%, stirring make ethyl acetimidate hydrochloride after completely dissolution in 3 minutes, start to drip
Adding mass percent concentration is 10% sodium hydrate aqueous solution, adjusts the pH value of solution in reaction kettle to 5 or so, reacts under room temperature
After 10min, organic phase is taken to do gas chromatographic analysis, the content of cyanaoethyl methacrylate are as follows: 86.9%.
System after reaction waits for pouring into that separatory funnel is static makes its layering under room temperature, and lower layer is water phase, and upper layer is organic phase,
The N- cyan ethyl ethylimidoote product of high-purity can be obtained in organic phase after being evaporated under reduced pressure, cyanaoethyl methacrylate in final product
Content are as follows: 99.6%, total recovery: 72%；The remaining water phase of lower layer obtains water and chlorination after multi-effect evaporator is concentrated and separated
Ammonium, water can return to for producing, and ammonium chloride can be used as by-product sale.
Embodiment 3:
Ethyl acetimidate hydrochloride 505.1g is added in the reaction kettle with stirring, quality is added under stirring
The cyanamide aqueous solution 468.2g that concentration is 35%, stirring make ethyl acetimidate hydrochloride after completely dissolution in 3 minutes, start to drip
Adding mass percent concentration is 20% sodium hydrate aqueous solution, adjusts the pH value of solution in reaction kettle to 6 or so, reacts under room temperature
After 30min, organic phase is taken to do gas chromatographic analysis, the content of cyanaoethyl methacrylate are as follows: 93.6%.
System after reaction waits for pouring into that separatory funnel is static makes its layering under room temperature, and lower layer is water phase, and upper layer is organic phase,
The N- cyan ethyl ethylimidoote product of high-purity can be obtained in organic phase after being evaporated under reduced pressure, cyanaoethyl methacrylate in final product
Content are as follows: 99.4%, total recovery: 78%；The remaining water phase of lower layer obtains water and chlorination after multi-effect evaporator is concentrated and separated
Ammonium, water can return to for producing, and ammonium chloride can be used as by-product sale.
Embodiment 4:
Ethyl acetimidate hydrochloride 505.1g is added in the reaction kettle with stirring, quality is added under stirring
The cyanamide aqueous solution 491.4g that concentration is 40%, stirring make ethyl acetimidate hydrochloride after completely dissolution in 3 minutes, start to drip
Adding mass percent concentration is 40% sodium hydrate aqueous solution, adjusts the pH value of solution in reaction kettle to 7 or so, reacts under room temperature
After 50min, organic phase is taken to do gas chromatographic analysis, the content of cyanaoethyl methacrylate are as follows: 95.4%.
System after reaction waits for pouring into that separatory funnel is static makes its layering under room temperature, and lower layer is water phase, and upper layer is organic phase,
The N- cyan ethyl ethylimidoote product of high-purity can be obtained in organic phase after being evaporated under reduced pressure, cyanaoethyl methacrylate in final product
Content are as follows: 99.1%, total recovery: 79%；The remaining water phase of lower layer obtains water and chlorination after multi-effect evaporator is concentrated and separated
Ammonium, water can return to for producing, and ammonium chloride can be used as by-product sale.
Embodiment 5:
Ethyl acetimidate hydrochloride 505.1g is added in the reaction kettle with stirring, quality is added under stirring
The cyanamide aqueous solution 327.6g that concentration is 45%, stirring make ethyl acetimidate hydrochloride after completely dissolution in 3 minutes, start to drip
Adding mass percent concentration is 25% ammonium hydroxide, adjusts the pH value of solution in reaction kettle to 8 or so, after reacting 70min under room temperature, takes
Organic phase does gas chromatographic analysis, the content of cyanaoethyl methacrylate are as follows: 95.4%.
System after reaction waits for pouring into that separatory funnel is static makes its layering under room temperature, and lower layer is water phase, and upper layer is organic phase,
The N- cyan ethyl ethylimidoote product of high-purity can be obtained in organic phase after being evaporated under reduced pressure, cyanaoethyl methacrylate in final product
Content are as follows: 99.4%, total recovery: 81%；The remaining water phase of lower layer obtains water and chlorination after multi-effect evaporator is concentrated and separated
Ammonium, water can return to for producing, and ammonium chloride can be used as by-product sale.
Embodiment 6:
Ethyl acetimidate hydrochloride 505.1g is added in the reaction kettle with stirring, quality is added under stirring
The cyanamide aqueous solution 360.5g that concentration is 50%, stirring make ethyl acetimidate hydrochloride after completely dissolution in 3 minutes, start to drip
Adding mass percent concentration is 10% ammonium hydroxide, adjusts the pH value of solution in reaction kettle to 9 or so, after reacting 90min under room temperature, takes
Organic phase does gas chromatographic analysis, the content of cyanaoethyl methacrylate are as follows: 91.2%.
System after reaction waits for pouring into that separatory funnel is static makes its layering under room temperature, and lower layer is water phase, and upper layer is organic phase,
The N- cyan ethyl ethylimidoote product of high-purity can be obtained in organic phase after being evaporated under reduced pressure, cyanaoethyl methacrylate in final product
Content are as follows: 99.3%, total recovery: 79%；The remaining water phase of lower layer obtains water and chlorination after multi-effect evaporator is concentrated and separated
Ammonium, water can return to for producing, and ammonium chloride can be used as by-product sale.
In order to prove that the present invention achieves preferable technical effect, in the following, will be further analyzed in conjunction with each attached drawing
It is bright.
Attached drawing 1 is the gas phase spectrogram that N- cyan ethyl ethylimidoote crude product is synthesized in the embodiment of the present invention 1, synthesizes crude product cyanogen
The content of base ethyl ester are as follows: 97.2%；
Attached drawing 2 is the gas phase spectrogram that N- cyan ethyl ethylimidoote crude product is synthesized in the embodiment of the present invention 6, synthesizes crude product cyanogen
The content of base ethyl ester are as follows: 91.2%；
Attached drawing 3 is using disodium hydrogen phosphate as catalyst, and reaction temperature is 40 DEG C, other reaction conditions and phase in embodiment 1
With the gas phase spectrogram of prepared N- cyan ethyl ethylimidoote crude product, the content of crude product cyanaoethyl methacrylate is synthesized are as follows: 88.1%, explanation
To the synthesis of cyanaoethyl methacrylate, there is no the content synthesized by the present invention is high after adding catalyst disodium hydrogen phosphate；
Attached drawing 4 is the gas phase spectrogram in the embodiment of the present invention 1 after the distillation of synthesis N- cyan ethyl ethylimidoote, cyanaoethyl methacrylate
Content are as follows: 99.8%.
By for above four attached drawings, it will be evident that finally having synthesized N- cyan ethyl ethylimidoote in the present invention.
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 (5)
- The synthetic method of 1.N- cyan ethyl ethylimidoote, which is characterized in that the synthesis step is as follows:S1, mixing: ethyl acetimidate hydrochloride is added in the reaction kettle for having turned on stirring, controls mixing speed in 150- 200r/min prevents ethyl acetimidate hydrochloride overcharge from killing stirring and is unable to operate normally, under stirring Cyanamide aqueous solution is added, comes into full contact with solid-liquid two-phase and ethyl acetimidate hydrochloride is completely dissolved and accelerates to react, stir It mixes and does not stop until reaction terminates；S2, it adjusts pH value: adjusting pH value to 5-9 in the mixed solution and dripping alkaline matter that S1 is obtained, temperature is controlled at 25 DEG C Within；S3, reaction: in 20-40 DEG C of room temperature, mixing speed to react material sufficiently in the state of 300r/min, the reaction time is 10-90min；S4, detection: it after above-mentioned reaction starts, is sampled once at interval of 10min, sample is passed through into chromatography and is detected, determines reaction Conversion ratio when reaching 99%, stop reaction；S5, separation: stopping stirring after the conversion ratio of above-mentioned reaction is stablized, and the water phase and organic phase stood into reactant is layered Afterwards, after organic phase being extracted out vacuum degree be -0.085MPa, temperature be 110 DEG C of vacuum distillations N- cyano ethyleneimine can be obtained Acetoacetic ester product, remaining water phase are -0.085MPa in vacuum degree through multi-effect evaporator, and temperature is that 80 DEG C of concentration and separation can obtain To water and ammonium chloride.
- 2. the synthetic method of N- cyan ethyl ethylimidoote according to claim 1, which is characterized in that in the step S1 The molar ratio of ethyl acetimidate hydrochloride and cyanamide is 1:0.8-1.2.
- 3. the synthetic method of N- cyan ethyl ethylimidoote according to claim 2, it is characterised in that, in the step S1 The mass percent concentration of cyanamide aqueous solution is 25-50%.
- 4. the synthetic method of N- cyan ethyl ethylimidoote according to claim 3, which is characterized in that in the step S1 The charge temperature of cyanamide aqueous solution is 0-10 DEG C.
- 5. the synthetic method of N- cyan ethyl ethylimidoote according to claim 4, which is characterized in that the step S2 In, alkaline matter is that mass percent concentration is 10-50% sodium hydrate aqueous solution or mass percent concentration is 10-25% ammonia Water.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072519A (en) * | 2019-12-17 | 2020-04-28 | 南通天泽化工有限公司 | Preparation method of cyanoethyl ester |
| 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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| 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 |