CN109970599A - A kind of method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine - Google Patents
A kind of method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine Download PDFInfo
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- CN109970599A CN109970599A CN201711452455.7A CN201711452455A CN109970599A CN 109970599 A CN109970599 A CN 109970599A CN 201711452455 A CN201711452455 A CN 201711452455A CN 109970599 A CN109970599 A CN 109970599A
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- Prior art keywords
- methyl
- formalin
- ethylphenyl
- azomethine
- ethyl aniline
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- 238000000034 method Methods 0.000 title claims abstract description 16
- -1 2- methyl -6- ethylphenyl Chemical group 0.000 title claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 14
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 title claims abstract description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000002466 imines Chemical class 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000018044 dehydration Effects 0.000 claims abstract description 13
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 239000000284 extract Substances 0.000 claims abstract description 5
- 238000000605 extraction Methods 0.000 claims abstract description 5
- 230000002411 adverse Effects 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of methods of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine, it is characterized in that, 2- methyl -6- ethyl aniline, formalin and catalyst of triethylamine are reacted by flow reactor, obtain thick imines, last vacuum dehydration obtains imines；Wherein, the 2- methyl -6- ethyl aniline and the reaction molar ratio of formalin are 1:1.1~1:2.0；The formalin concentration is 10%-60%；Reaction temperature is 50 DEG C -90 DEG C；The reactor can be extraction is tower, extracts box or multi-floating bodies formula etc.；- 100 DEG C of vacuum dehydration temperature 60 C；Dewatering vacuum is -80Kpa--101Kpa.Using 2- methyl -6- ethyl aniline and formalin, the successive reaction under closed environment produces N-2- methyl -6- ethylphenyl azomethine to the present invention, compared with prior art, not only reduces labor intensity, security risk, but also improve yield, effectively reduces cost.
Description
Technical field
It is more particularly to a kind of the present invention relates to synthesis N-2- methyl -6- ethylphenyl azomethine technical field
The method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine.
Background technique
The synthesis of N-2- methyl -6- ethylphenyl azomethine (hereinafter referred to as: imines) at present is using 2- methyl -6- ethyl
Aniline and the paraformaldehyde intermittent reaction in reaction kettle, large labor intensity, security risk is high, and yield is low, at high cost.
Therefore, how a kind of not only reduction labor intensity, security risk, but also high income, continuous conjunction at low cost are provided
The problem of method at Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine is 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 not only reduction labor intensity, security risk, but also high income, it is at low cost
Continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine method.
To achieve the above object, the invention provides the following technical scheme:
A kind of method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine, which is characterized in that 2- first
Base -6- ethyl aniline, formalin and catalyst of triethylamine are reacted by flow reactor, obtain thick imines, last vacuum
Dehydration obtains imines；Wherein, the 2- methyl -6- ethyl aniline and the reaction molar ratio of formalin are 1:1.1~1:
2.0；The formalin concentration is 10%-60%；Reaction temperature is 50 DEG C -90 DEG C；The reactor can be extraction it is tower,
Extract box or multi-floating bodies formula etc.；- 100 DEG C of vacuum dehydration temperature 60 C；Dewatering vacuum is -80Kpa--101Kpa.
Preferably, in a kind of above-mentioned method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine
In, the 2- methyl -6- ethyl aniline fair current or the separation of adverse current hybrid reaction in the reactor.
It can be seen via above technical scheme that compared with prior art, the present disclosure provides a kind of continuous synthesis Acetochlors
The method of intermediate N 2- methyl -6- ethylphenyl azomethine, which is characterized in that 2- methyl -6- ethyl aniline, formalin
It is reacted with catalyst of triethylamine by flow reactor, obtains thick imines, last vacuum dehydration obtains imines；Wherein, the 2-
Methyl -6- ethyl aniline and the reaction molar ratio of formalin are 1:1.1~1:2.0；The formalin concentration is
10%-60%；Reaction temperature is 50 DEG C -90 DEG C；The reactor can be extraction is tower, extracts box or multi-floating bodies formula etc.；
- 100 DEG C of vacuum dehydration temperature 60 C；Dewatering vacuum is -80Kpa--101Kpa.The present invention utilizes 2- methyl -6- ethyl aniline
Successive reaction produces N-2- methyl -6- ethylphenyl azomethine under closed environment with formalin, compared with prior art,
Labor intensity, security risk are not only reduced, but also improves yield, effectively reduces cost.
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 flow diagram of 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.
Labor intensity, security risk, but also high income, company at low cost are not only reduced the embodiment of the invention discloses a kind of
The method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine.
Attached drawing 1 is please referred to, for a kind of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl disclosed by the invention
The method of azomethine, specifically includes:
2- methyl -6- ethyl aniline, formalin and catalyst of triethylamine are reacted by flow reactor, obtain thick imines,
Last vacuum dehydration obtains imines；Wherein, 2- methyl -6- ethyl aniline and the reaction molar ratio of formalin be 1:1.1~
1:2.0；Formalin concentration is 10%-60%；Reaction temperature is 50 DEG C -90 DEG C；Reactor, which can be, extracts tower, extraction box
Formula or multi-floating bodies formula etc.；- 100 DEG C of vacuum dehydration temperature 60 C；Dewatering vacuum is -80Kpa--101Kpa；The chemistry of reaction
Equation is as follows:
Using 2- methyl -6- ethyl aniline and formalin, the successive reaction under closed environment produces N-2- methyl-to the present invention
6- ethylphenyl azomethine not only reduces labor intensity, security risk, but also improve yield, effectively drops compared with prior art
Low cost.
In order to further optimize the above technical scheme, fair current or adverse current mix 2- methyl -6- ethyl aniline in the reactor
Reaction Separation.
In order to further optimize the above technical scheme, specific embodiment 1 are as follows:
First 37% formalin is constantly pumped into tower reactor with the rate of 7.5ml/min, when liquid level reaches half,
2- methyl -6- the ethyl aniline that 1% triethylamine is added constantly is pumped into tower reactor with the rate of 10ml/min, control tower
65 DEG C of temperature opens thick imines after oil mutually reaches tower top and receives the thick imines of valve reception, and obtained thick imines is in 80 DEG C, -920Kpa
Lower vacuum dehydration obtains imines, content 98.3%, yield 97.5%.
In order to further optimize the above technical scheme, specific embodiment 2 are as follows:
First 37% formalin is constantly pumped into tower reactor with the rate of 8.5ml/min, when liquid level reaches half,
2- methyl -6- the ethyl aniline that 1% triethylamine is added constantly is pumped into tower reactor with the rate of 10ml/min, control tower
65 DEG C of temperature opens thick imines after oil mutually reaches tower top and receives the thick imines of valve reception, and obtained thick imines is in 80 DEG C, -920Kpa
Lower vacuum dehydration obtains imines, content 98.5%, yield 98%.
In order to further optimize the above technical scheme, specific embodiment 3 are as follows:
First 37% formalin is constantly pumped into tower reactor with the rate of 9.5ml/min, when liquid level reaches half,
2- methyl -6- the ethyl aniline that 1% triethylamine is added constantly is pumped into tower reactor with the rate of 10ml/min, control tower
65 DEG C of temperature opens thick imines after oil mutually reaches tower top and receives the thick imines of valve reception, and obtained thick imines is in 80 DEG C, -920Kpa
Lower vacuum dehydration obtains imines, content 99.2%, yield 98.5%.
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 (2)
1. a kind of method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine, which is characterized in that 2- first
Base -6- ethyl aniline, formalin and catalyst of triethylamine are reacted by flow reactor, obtain thick imines, last vacuum
Dehydration obtains imines；Wherein, the 2- methyl -6- ethyl aniline and the reaction molar ratio of formalin are 1:1.1~1:
2.0；The formalin concentration is 10%-60%；Reaction temperature is 50 DEG C -90 DEG C；The reactor can be extraction it is tower,
Extract box or multi-floating bodies formula etc.；- 100 DEG C of vacuum dehydration temperature 60 C；Dewatering vacuum is -80Kpa--101Kpa.
2. a kind of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine according to claim 1
Method, which is characterized in that the 2- methyl -6- ethyl aniline fair current or the separation of adverse current hybrid reaction in the reactor.
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| CN201711452455.7A CN109970599A (en) | 2017-12-28 | 2017-12-28 | A kind of method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine |
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| CN201711452455.7A CN109970599A (en) | 2017-12-28 | 2017-12-28 | A kind of method of continuous synthesis Acetochlor intermediate N 2- methyl -6- ethylphenyl azomethine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031519A (en) * | 2021-12-08 | 2022-02-11 | 浙江工业大学 | Method for synthesizing N-aryl imine |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031519A (en) * | 2021-12-08 | 2022-02-11 | 浙江工业大学 | Method for synthesizing N-aryl imine |
| CN114031519B (en) * | 2021-12-08 | 2024-04-26 | 浙江工业大学 | Method for synthesizing N-aryl imine |
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Effective date of registration: 20210111 Address after: 256600 south side of xinyongxin Road, Binbei office, Bincheng District, Binzhou City, Shandong Province Applicant after: Shoujian Technology Co.,Ltd. Address before: 256600 south side of xinyongxin Road, Binbei office, Bincheng District, Binzhou City, Shandong Province Applicant before: SHANDONG QIAOCHANG CHEMICAL Co.,Ltd. |
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