CN107235860A - A kind of synthesis technique of the dichlorophenyl isocyanate of diuron intermediate 3,4 - Google Patents
A kind of synthesis technique of the dichlorophenyl isocyanate of diuron intermediate 3,4 Download PDFInfo
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- CN107235860A CN107235860A CN201710566924.1A CN201710566924A CN107235860A CN 107235860 A CN107235860 A CN 107235860A CN 201710566924 A CN201710566924 A CN 201710566924A CN 107235860 A CN107235860 A CN 107235860A
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- phosgene
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- toluene
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- diuron
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of synthesis technique of the dichlorophenyl isocyanate of diuron intermediate 3,4, its step is as follows：1) 3,4 dichloroanilines and toluene are added in dehydrating kettle, 3.4 dichloroaniline toluene liquid are obtained；2) when the moisture in the temperature described in ascending step 1 in dehydrating kettle, kettle to be drained off is less than less than 0.5%, described in step 13,4 dichloroaniline toluene liquid are put into measuring tank, phosgene toluene liquid are added dropwise, while being passed through phosgene；3) after after the liquid completion of dropwise addition of phosgene toluene described in step 2, continue to be passed through phosgene, obtain just 3,4 dichlorophenyl isocyanates of system；4) it will just make 3,4 dichlorophenyl isocyanates described in step 3 to put into hot light kettle, while raising the temperature of hot light kettle until after 110 DEG C, being filtered, obtaining 3,4 dichlorophenyl isocyanates.The present invention is simple to operate, and 3 produced, 4 dichlorophenyl isocyanates have high-purity.
Description
Technical field
The present invention relates to diuron synthesis technique field, more particularly to a kind of diuron intermediate 3,4- dichlorophenyl isocyanides
The synthesis technique of acid esters.
Background technology
3,4- dichlorophenyl isocyanates, Chinese nickname isocyanic acid -3,4- Dichlorfop etc., commonly use used as pesticides and medicine
Intermediate, while being also the important intermediate such as synthetic herbicide linuron, telvar, diuron.
In the prior art, 3,4- dichlorophenyl isocyanates are as the intermediate for synthesizing diuron, usually to its side of preparation
Method is less demanding, so as to cause the quality of diuron prepared not high.
The content of the invention
The problem of purpose of the present invention exists aiming at above-mentioned prior art is simple there is provided a kind of technique, improves product
The diuron intermediate 3 of quality, the synthesis technique of 4- dichlorophenyl isocyanates.
The technical solution adopted in the present invention is：A kind of diuron intermediate 3, the synthesis work of 4- dichlorophenyl isocyanates
Skill, its step is as follows：
1) it is 3,4-DCA by weight to be added in dehydrating kettle：Toluene=1.5-2.0:The 3 of 0.9-1.2 proportionings,
4- dichloroanilines and toluene, obtain 3,4-DCA toluene liquid；
2) when the moisture in the temperature described in ascending step 1 in dehydrating kettle, kettle to be drained off is less than 0.5%, by step 1
Described in 3,4-DCA toluene liquid input measuring tank, phosgene first of the 0.2-0.6 parts by weight temperature below 20 DEG C is added dropwise
Benzene liquid, while being passed through the phosgene of 1.3-1.6 parts by weight；
3) after after the liquid completion of dropwise addition of phosgene toluene described in step 2, continuing to be passed through the phosgene of 0.5-0.9 parts by weight, obtain
Just make 3,4- dichlorophenyl isocyanates；
4) it will just make 3,4- dichlorophenyl isocyanates described in step 3 to put into hot light kettle, while raising hot light kettle
Temperature is until after 110 DEG C, being filtered, obtaining 3,4- dichlorophenyl isocyanates.
Further, the weight ratio of 3,4-DCA and toluene is 3,4-DCA in the step 1：Toluene=
1.72:1.13。
Further, when the moisture in the step 2 in dehydrating kettle is 0.2%-0.5%, by 3,4- bis- described in step 1
In chlorobenzene carbaryl liquid input measuring tank.
Further, the phosgene toluene liquid of 0.43 10-20 DEG C of parts by weight temperature is added dropwise in the step 2, is passed through simultaneously
The weight concentration of 1.426 parts by weight is 70% phosgene.
Further, continue to be passed through 0.759 weight after after the liquid completion of dropwise addition of phosgene toluene described in step 2 in the step 3
The weight concentration for measuring part is 60% phosgene, obtains just system 3,4- dichlorophenyl isocyanates.
Further, being filtered into the step 4 is filtered with composite filtering film.
Further, the preparation method of the composite filtering film is as follows：
1) carborundum of 2 parts by weight is calcined at 700-900 DEG C, is subsequently placed into the hydrogen peroxide solution of 4 parts by weight
Middle immersion 1-2h, rinses standby after taking-up；
2) the inorganic nano dispersant that 3.5 parts by weight concentration are 0.8g/L is added into the carborundum after flushing, is then added
Enter the sodium carboxymethylcellulose of 1.2 parts by weight, stirred at a temperature of 50-60 DEG C, obtain mixed liquor；
3) adhesive of 2.5 parts by weight is added in every liter of 15g ratio into obtained mixed liquor, is coated with after stirring
In on basement membrane.
Further, the phosgene is to be warming up to 100-115 after mixing acephatemet, solid phosgene with inert organic solvents
DEG C gained.
Further, the percentage in the phosgene shared by acephatemet, solid phosgene and inert organic solvents three is first
Amine phosphorus 0.22%, solid phosgene 10.23%, inert organic solvents 3.65%.
The diuron intermediate 3 that the present invention is provided, the beneficial effect of the synthesis technique of 4- dichlorophenyl isocyanates is：This
Invention is simple to operate, is handled with acephatemet and inert organic solvents after solid phosgene, makes the purity and liveness of phosgene more preferable, and
Just system 3,4- dichlorophenyl isocyanates are filtered using composite filtering film, make 3, the 4- dichlorophenyl isocyanates produced
With high-purity, so that the diuron made from 3, the 4- dichlorophenyl isocyanates has high-quality.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention
It is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to
Limit the present invention.
Embodiment 1
3,4-DCA and toluene are pressed 1.72:1.13 weight is than in input dehydrating kettle, obtaining 3,4-DCA first
Benzene liquid, when the moisture then raised in the temperature in the dehydrating kettle, kettle to be drained off is 0.2%-0.5%, by 3, the 4- bis-
In chlorobenzene carbaryl liquid input measuring tank, the phosgene toluene liquid of 0.43 10-20 DEG C of parts by weight temperature is then added dropwise, is passed through simultaneously
The weight concentration of 1.426 parts by weight is 70% phosgene, after after the phosgene toluene liquid completion of dropwise addition, continues to be passed through 0.759 weight
The weight concentration for measuring part is 60% phosgene, obtains just system 3,4- dichlorophenyl isocyanates, then by just system 3, the 4- bis-
Chlorophenyl isocyanate is put into hot light kettle, while raising the temperature of hot light kettle until after 110 DEG C, being carried out with composite filtering film
After filter, 3,4- dichlorophenyl isocyanates are obtained.
Further, the preparation method of the composite filtering film is：The carborundum of 2 parts by weight is entered at 800 DEG C first
Soaked in row roasting, the hydrogen peroxide solution for being subsequently placed into 4 parts by weight and rinse standby after 1h, taking-up；Then to the carbonization after flushing
The inorganic nano dispersant that 3.5 parts by weight concentration are 0.8g/L is added in silicon, the carboxymethyl cellulose of 1.2 parts by weight is subsequently added into
Sodium, stirs at a temperature of 55 DEG C, obtains mixed liquor；In every liter of 15g ratio addition 2.5 in the mixed liquor most obtained backward
The adhesive of parts by weight, is coated on basement membrane after stirring.
Further, the phosgene is is warming up to 110 DEG C of institutes after mixing acephatemet, solid phosgene with inert organic solvents
Obtain, and the percentage shared by three is acephatemet 0.22%, solid phosgene 10.23%, inert organic solvents 3.65%.
The present invention it is simple to operate, 3, the 4- dichlorophenyl isocyanates produced have high-purity so that by this 3,4-
Diuron has high-quality made from dichlorophenyl isocyanate.
Embodiment 2
3,4-DCA and toluene are pressed 1.5:0.9 weight is than in input dehydrating kettle, obtaining 3,4-DCA toluene
Liquid, when the moisture then raised in the temperature in the dehydrating kettle, kettle to be drained off is 0.2%-0.5%, by 3, the 4- dichloros
In aniline toluene liquid input measuring tank, the phosgene toluene liquid of 0.2 10-20 DEG C of parts by weight temperature is then added dropwise, while being passed through 1.3 weights
The weight concentration for measuring part is 70% phosgene, after after the phosgene toluene liquid completion of dropwise addition, continues to be passed through the weight of 0.5 parts by weight
Concentration is 60% phosgene, obtains just system 3,4- dichlorophenyl isocyanates, then by just system 3, the 4- dichlorophenyl isocyanides
Acid esters is put into hot light kettle, while raising the temperature of hot light kettle until after 110 DEG C, after being filtered with composite filtering film, obtaining
3,4- dichlorophenyl isocyanates.
Further, the preparation method of the composite filtering film is：The carborundum of 2 parts by weight is entered at 700 DEG C first
Soaked in row roasting, the hydrogen peroxide solution for being subsequently placed into 4 parts by weight and rinse standby after 1h, taking-up；Then to the carbonization after flushing
The inorganic nano dispersant that 3.5 parts by weight concentration are 0.8g/L is added in silicon, the carboxymethyl cellulose of 1.2 parts by weight is subsequently added into
Sodium, stirs at a temperature of 50 DEG C, obtains mixed liquor；In every liter of 15g ratio addition 2.5 in the mixed liquor most obtained backward
The adhesive of parts by weight, is coated on basement membrane after stirring.
Further, the phosgene is is warming up to 100 DEG C of institutes after mixing acephatemet, solid phosgene with inert organic solvents
Obtain, and the percentage shared by three is acephatemet 0.22%, solid phosgene 10.23%, inert organic solvents 3.65%.
The present invention it is simple to operate, 3, the 4- dichlorophenyl isocyanates produced have high-purity so that by this 3,4-
Diuron has high-quality made from dichlorophenyl isocyanate.
Embodiment 3
3,4-DCA and toluene are pressed 2.0:1.2 weight is than in input dehydrating kettle, obtaining 3,4-DCA toluene
Liquid, when the moisture then raised in the temperature in the dehydrating kettle, kettle to be drained off is 0.2%-0.5%, by 3, the 4- dichloros
In aniline toluene liquid input measuring tank, the phosgene toluene liquid of 0.6 10-20 DEG C of parts by weight temperature is then added dropwise, while being passed through 1.6 weights
The weight concentration for measuring part is 70% phosgene, after after the phosgene toluene liquid completion of dropwise addition, continues to be passed through the weight of 0.9 parts by weight
Concentration is 60% phosgene, obtains just 3.4 dichloro phenylisocyanates of system, then throws 3.4 dichloro phenylisocyanates of the just system
Enter in hot light kettle, while raising the temperature of hot light kettle until after 110 DEG C, after being filtered with composite filtering film, obtaining 3,4- bis-
Chlorophenyl isocyanate.
Further, the preparation method of the composite filtering film is：The carborundum of 2 parts by weight is entered at 900 DEG C first
Soaked in row roasting, the hydrogen peroxide solution for being subsequently placed into 4 parts by weight and rinse standby after 2h, taking-up；Then to the carbonization after flushing
The inorganic nano dispersant that 3.5 parts by weight concentration are 0.8g/L is added in silicon, the carboxymethyl cellulose of 1.2 parts by weight is subsequently added into
Sodium, stirs at a temperature of 60 DEG C, obtains mixed liquor；In every liter of 15g ratio addition 2.5 in the mixed liquor most obtained backward
The adhesive of parts by weight, is coated on basement membrane after stirring.
Further, the phosgene is is warming up to 115 DEG C of institutes after mixing acephatemet, solid phosgene with inert organic solvents
Obtain, and the percentage shared by three is acephatemet 0.22%, solid phosgene 10.23%, inert organic solvents 3.65%.
The present invention it is simple to operate, 3, the 4- dichlorophenyl isocyanates produced have high-purity so that by this 3,4-
Diuron has high-quality made from dichlorophenyl isocyanate.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
Any modifications, equivalent substitutions and improvements made within refreshing and principle etc., should be included in the scope of the protection.
Claims (9)
1. a kind of diuron intermediate 3, the synthesis technique of 4- dichlorophenyl isocyanates, it is characterised in that its step is as follows：
1) it is 3,4-DCA by weight to be added in dehydrating kettle：Toluene=1.5-2.0:3, the 4- bis- of 0.9-1.2 proportionings
Chloroaniline and toluene, obtain 3,4-DCA toluene liquid；
2) when the moisture in the temperature described in ascending step 1 in dehydrating kettle, kettle to be drained off is less than 0.5%, by institute in step 1
State in 3,4-DCA toluene liquid input measuring tank, phosgene toluene liquid of the 0.2-0.6 parts by weight temperature below 20 DEG C be added dropwise,
The phosgene of 1.3-1.6 parts by weight is passed through simultaneously；
3) after after the liquid completion of dropwise addition of phosgene toluene described in step 2, continuing to be passed through the phosgene of 0.5-0.9 parts by weight, obtain just making
3,4- dichlorophenyl isocyanates；
4) it will just make 3,4- dichlorophenyl isocyanates described in step 3 to put into hot light kettle, while raising the temperature of hot light kettle
Until after 110 DEG C, being filtered, obtaining 3,4- dichlorophenyl isocyanates.
2. diuron intermediate 3 according to claim 1, the synthesis technique of 4- dichlorophenyl isocyanates, its feature exists
In the weight ratio of 3,4-DCA and toluene is 3,4-DCA in the step 1：Toluene=1.72:1.13.
3. diuron intermediate 3 according to claim 1, the synthesis technique of 4- dichlorophenyl isocyanates, its feature exists
In when the moisture in the step 2 in dehydrating kettle is 0.2%-0.5%, by the throwing of the liquid of 3,4-DCA toluene described in step 1
Enter in measuring tank.
4. diuron intermediate 3 according to claim 1, the synthesis technique of 4- dichlorophenyl isocyanates, its feature exists
In the phosgene toluene liquid of 0.43 10-20 DEG C of parts by weight temperature being added dropwise in the step 2, while being passed through the weight of 1.426 parts by weight
Concentration is 70% phosgene.
5. diuron intermediate 3 according to claim 1, the synthesis technique of 4- dichlorophenyl isocyanates, its feature exists
In after after the liquid completion of dropwise addition of phosgene toluene described in step 2, continuing to be passed through the weight concentration of 0.759 parts by weight in the step 3
For 60% phosgene, just system 3,4- dichlorophenyl isocyanates are obtained.
6. diuron intermediate 3 according to claim 1, the synthesis technique of 4- dichlorophenyl isocyanates, its feature exists
In being filtered into the step 4 is filtered with composite filtering film.
7. diuron intermediate 3 according to claim 6, the synthesis technique of 4- dichlorophenyl isocyanates, its feature exists
In the preparation method of the composite filtering film is as follows：
1) carborundum of 2 parts by weight is calcined at 700-900 DEG C, is subsequently placed into the hydrogen peroxide solution of 4 parts by weight and soaks
1-2h is steeped, rinses standby after taking-up；
2) the inorganic nano dispersant that 3.5 parts by weight concentration are 0.8g/L is added into the carborundum after flushing, 1.2 are subsequently added into
The sodium carboxymethylcellulose of parts by weight, stirs at a temperature of 50-60 DEG C, obtains mixed liquor；
3) adhesive of 2.5 parts by weight is added in every liter of 15g ratio into obtained mixed liquor, base is coated on after stirring
On film.
8. diuron intermediate 3 according to claim 1, the synthesis technique of 4- dichlorophenyl isocyanates, its feature exists
In the phosgene is to be warming up to 100-115 DEG C of gained after mixing acephatemet, solid phosgene with inert organic solvents.
9. diuron intermediate 3 according to claim 8, the synthesis technique of 4- dichlorophenyl isocyanates, its feature exists
In the percentage in the phosgene shared by acephatemet, solid phosgene and inert organic solvents three is acephatemet 0.22%, solid
Phosgene 10.23%, inert organic solvents 3.65%.
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| CN201710566924.1A CN107235860B (en) | 2017-07-12 | 2017-07-12 | A kind of diuron intermediate 3, the synthesis technology of 4- dichlorophenyl isocyanate |
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| CN201710566924.1A CN107235860B (en) | 2017-07-12 | 2017-07-12 | A kind of diuron intermediate 3, the synthesis technology of 4- dichlorophenyl isocyanate |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449397A (en) * | 1966-04-06 | 1969-06-10 | Du Pont | Preparation of dichlorophenyl isocyanate |
| CN101709041A (en) * | 2009-11-13 | 2010-05-19 | 安徽广信集团铜陵化工有限公司 | Process for producing diuron |
| CN103739520A (en) * | 2013-12-26 | 2014-04-23 | 安徽广信农化股份有限公司 | Refining method of 3,4-dichlorobenzene isocyanate |
| CN104356028A (en) * | 2014-09-29 | 2015-02-18 | 湖南海利常德农药化工有限公司 | Method for continuously preparing 3,4-dichlorophenyl isocyanate |
| CN106422813A (en) * | 2016-09-20 | 2017-02-22 | 芜湖成德龙过滤设备有限公司 | Ceramic filter membrane and preparation method thereof |
-
2017
- 2017-07-12 CN CN201710566924.1A patent/CN107235860B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449397A (en) * | 1966-04-06 | 1969-06-10 | Du Pont | Preparation of dichlorophenyl isocyanate |
| CN101709041A (en) * | 2009-11-13 | 2010-05-19 | 安徽广信集团铜陵化工有限公司 | Process for producing diuron |
| CN103739520A (en) * | 2013-12-26 | 2014-04-23 | 安徽广信农化股份有限公司 | Refining method of 3,4-dichlorobenzene isocyanate |
| CN104356028A (en) * | 2014-09-29 | 2015-02-18 | 湖南海利常德农药化工有限公司 | Method for continuously preparing 3,4-dichlorophenyl isocyanate |
| CN106422813A (en) * | 2016-09-20 | 2017-02-22 | 芜湖成德龙过滤设备有限公司 | Ceramic filter membrane and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 王传方: "复合碳化硅精细过滤膜制备、微结构及性能的研究", 《中国优秀硕士学位论文 工程科技I辑》 * |
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