CN107129445A - A kind of synthetic method of diuron - Google Patents
A kind of synthetic method of diuron Download PDFInfo
- Publication number
- CN107129445A CN107129445A CN201710421976.XA CN201710421976A CN107129445A CN 107129445 A CN107129445 A CN 107129445A CN 201710421976 A CN201710421976 A CN 201710421976A CN 107129445 A CN107129445 A CN 107129445A
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- China
- Prior art keywords
- diuron
- dimethylamine
- synthetic method
- dcpi
- toluene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides a kind of synthetic method of diuron, and it comprises the following steps：The 3 of pretreatment, 4 dichloro phenyl isocyanate toluene liquid are added drop-wise in dimethylamine toluene solution, temperature is no more than 15 DEG C, are added dropwise that terminal PH is 7 11 or so, 3,4 dichloro phenyl isocyanates and dimethylamine molar ratio is 1:1‑3；Suction filtration is carried out after being added dropwise to complete, gained filter cake is dried in 90~100 DEG C to be used to prepare dimethylamine toluene solution after obtained diuron original drug, gained suction filtration after solvent recovery.Present invention synthesis diuron industrial operation step is reduced, and purity and yield are improved, and post processing is produced without waste water, cost reduction.
Description
Technical field
The invention belongs to synthesize field.It is more particularly related to a kind of synthetic method of diuron.
Background technology
Diuron is used to prevent and kill off the general weeds in noncrop area, and anti-weeds spread again.The product are also used for asparagus, citrus, cotton
Flower, pineapple, sugarcane, the weeding of temperate zone trees and shrub fruit.
Current industrial production method is that 3,4-DCPI toluene liquid is cooled into less than 20 DEG C, it is added dropwise 30%-
(ester amine ratio is 1 to 40% dimethylamine agueous solution:1.05), temperature voluntarily rises to 34 DEG C, and control is no more than 50 DEG C, and terminal PH is added dropwise
About 9 or so, 15 DEG C are reacted 2.5 hours, are then centrifuged for filtering, and recycling design, filter cake washing is dry after 90~100 DEG C in neutrality
It is dry, diuron original drug is made.
Subject matter is：
1. impurity is more than 1% in diuron, related foreign standard is not met；
2. industrial operation step is more, particularly suction filtration Mother liquor will carry out turnout reason, produce waste water.
The content of the invention
It is an object of the invention to solve at least the above, and provide the advantage that at least will be described later.
Find that impurity is mainly derived from the acidity of 3,4-DCPI toluene liquid after analyzing existing synthetic method,
Therefore need to pre-process the solution.In addition, if building-up process, which is avoided that, uses the aqueous solution, will using homogeneous solvent
Associative operation can be avoided, waste water will not be also brought.
In order to realize object of the present invention and further advantage, the present invention provides a kind of side for efficiently synthesizing diuron
Method, the high efficiency method of the diuron synthesis of more particularly to industrial operation step reduction, and mother liquor can apply mechanically recovery for next group
Secondary synthesis.Its synthetic method is shown below：
The technical scheme is that：
A kind of synthetic method of diuron, it comprises the following steps：
By the 3,4-DCPI toluene liquid of pretreatment, it is added drop-wise in dimethylamine toluene solution, temperature is no more than
15 DEG C, it is 7-11 or so that terminal PH, which is added dropwise, and 3,4-DCPI and dimethylamine molar ratio are 1:1-3；
Suction filtration is carried out after being added dropwise to complete, gained filter cake is dried molten after obtained diuron original drug, gained suction filtration in 90~100 DEG C
Agent is used to prepare dimethylamine toluene solution after reclaiming.
Preferably, in the synthetic method of described diuron, 3,4-DCPI and dimethylamine feed intake mole
Than for 1:1.5.
Preferably, in the synthetic method of described diuron, 3,4-DCPI toluene liquid and dimethylamine first
The concentration of benzole soln is 5%-50%.
Preferably, in the synthetic method of described diuron, the mass concentration of 3,4-DCPI toluene liquid
For 20%-30%, the mass concentration of dimethylamine toluene solution is 5%-15%.
Preferably, in the synthetic method of described diuron, the dropwise addition terminal pH is 9-10.
Preferably, in the synthetic method of described diuron, the pretreatment bag of 3,4-DCPI toluene liquid
Include：
Nitrogen is passed through into 3,4-DCPI toluene solution, the temperature for being passed through nitrogen is 15-60 DEG C, is passed through nitrogen
The terminal of gas is less than 0.1% for the acidity of solution.
Preferably, in the synthetic method of described diuron, for preparing dimethylamine after solvent recovery after the suction filtration
Toluene solution, applies mechanically number of times 1-10 times.
Preferably, in the synthetic method of described diuron, for preparing dimethylamine after solvent recovery after the suction filtration
Toluene solution, applies mechanically number of times 1-5 times.
The present invention provides a kind of synthetic method of diuron, and it comprises the following steps：By 3, the 4- dichloro isocyanides of pretreatment
Acid phenenyl ester toluene liquid, is added drop-wise in dimethylamine toluene solution, and temperature is no more than 15 DEG C, and it is 7-11 or so, 3,4- that terminal PH, which is added dropwise,
Dichloro phenyl isocyanate and dimethylamine molar ratio are 1:1-3；Suction filtration is carried out after being added dropwise to complete, gained filter cake is in 90~100
DEG C dry is used to prepare dimethylamine toluene solution after obtained diuron original drug, gained suction filtration after solvent recovery.Present invention synthesis enemy
The grand industrial operation step of grass is reduced, and purity and yield are improved, and post processing is produced without waste water, cost reduction.
Further advantage, target and the feature of the present invention embodies part by following explanation, and part will also be by this
The research and practice of invention and be understood by the person skilled in the art.
Embodiment
With reference to embodiment, the present invention is described in further detail, to make those skilled in the art's reference
Specification word can be implemented according to this.
It should be appreciated that such as " having ", "comprising" and " comprising " term used herein do not allot one or many
The presence or addition of individual other elements or its combination.
Embodiment 1
100g toluene is added in four-hole bottle, 5 DEG C or so are cooled to, 6.5g dimethylamine gas is passed through, the first of dimethylamine is formed
Benzole soln (mass concentration 6.1%).Stirring is opened, by the 3,4-DCPI toluene solution that 100g contents are 25%
(now 3,4-DCPI and dimethylamine molar ratio are 1:1.08) (detection acidity 0.1% is passed through after nitrogen 2h
Below), in being added drop-wise in 30-50min in dimethylamine solution, it is ensured that process temperature is added dropwise between 5-12 DEG C, after completion of dropping,
Continue to stir 30min.Suction filtration (filter cake can be washed once with whole mother liquors) obtains white solid, and quality is 30.5g after 90 DEG C of drying, miscellaneous
Matter content 0.1%, yield 98.3%.Mother liquid recycle once prepares dimethylamine solution, synthesis yield 98.2%, impurity content afterwards
0.11%.
Embodiment 2
300g toluene is added in four-hole bottle, 10 DEG C or so are cooled to, 32.5g dimethylamine gas is passed through, dimethylamine is formed
Toluene solution (mass concentration 9.8%).Stirring is opened, by the 3,4-DCPI toluene solution that 300g contents are 30%
(now 3,4-DCPI and dimethylamine molar ratio are 1:1.5) be passed through after nitrogen 3h (detection acidity 0.1% with
Under), in being added drop-wise in 100min in dimethylamine solution, it is ensured that process temperature is added dropwise between 5-12 DEG C, after completion of dropping, continue
Stir 50min.Suction filtration (filter cake can be washed once with whole mother liquors) obtains white solid, and quality is 109g after 90 DEG C of drying, and impurity contains
Amount 0.1%, yield 97.7%.Dimethylamine solution, synthesis yield 97.7%, impurity content are prepared after mother liquid recycle five times
0.15%.
Embodiment 3
300g toluene is added in four-hole bottle, 0 DEG C or so is cooled to, 48.13g dimethylamine gas is passed through, dimethylamine is formed
Toluene solution (mass concentration 13.83%).Stirring is opened, 500g contents is molten for 20% 3,4-DCPI toluene
(now 3,4-DCPI and dimethylamine molar ratio are 1 to liquid:2) be passed through after nitrogen 4h (detection acidity 0.1% with
Under), in being added drop-wise in 100min in dimethylamine solution, it is ensured that process temperature is added dropwise between 5-15 DEG C, after completion of dropping, continue
Stir 50min.Suction filtration (filter cake can be washed once with whole mother liquors) obtains white solid, and quality is 121g after 90 DEG C of drying, and impurity contains
Amount 0.11%, yield 97.5%.Dimethylamine solution, synthesis yield 98.0%, impurity content are prepared after mother liquid recycle eight times
0.17%.
Although embodiment of the present invention is disclosed as above, it is not restricted in specification and embodiment listed
With it can be applied to various suitable the field of the invention completely, can be easily for those skilled in the art
Other modification is realized, therefore under the universal limited without departing substantially from claim and equivalency range, the present invention is not limited
In specific details.
Claims (8)
1. the synthetic method of diuron, it is characterised in that comprise the following steps：
The 3,4-DCPI toluene liquid of pretreatment is added drop-wise in dimethylamine toluene solution, temperature is no more than 15 DEG C,
It is 7-11 or so that terminal PH, which is added dropwise, and 3,4-DCPI and dimethylamine molar ratio are 1:1-3；
Suction filtration is carried out after being added dropwise to complete, gained filter cake is dried solvent after obtained diuron original drug, gained suction filtration in 90~100 DEG C and returned
It is used to prepare dimethylamine toluene solution after receipts.
2. the synthetic method of diuron as claimed in claim 1, it is characterised in that 3,4-DCPI and dimethylamine
Molar ratio is 1:1.5.
3. the synthetic method of diuron as claimed in claim 1, it is characterised in that 3,4-DCPI toluene liquid and
The mass concentration of dimethylamine toluene solution is 5%-50%.
4. the synthetic method of diuron as claimed in claim 3, it is characterised in that 3,4-DCPI toluene liquid
Mass concentration is 20%-30%, and the mass concentration of dimethylamine toluene solution is 5%-15%.
5. the synthetic method of diuron as claimed in claim 1, it is characterised in that the dropwise addition terminal pH is 9-10.
6. the synthetic method of diuron as claimed in claim 1, it is characterised in that 3,4-DCPI toluene liquid
Pretreatment includes：
Nitrogen is passed through into 3,4-DCPI toluene solution, the temperature for being passed through nitrogen is 15-60 DEG C, is passed through nitrogen
Terminal is less than 0.1% for the acidity of solution.
7. the synthetic method of diuron as claimed in claim 1, it is characterised in that be used to match somebody with somebody after solvent recovery after the suction filtration
Dimethylamine toluene solution processed, applies mechanically number of times 1-10 times.
8. the synthetic method of diuron as claimed in claim 7, it is characterised in that be used to match somebody with somebody after solvent recovery after the suction filtration
Dimethylamine toluene solution processed, applies mechanically number of times 1-5 times.
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| CN201710421976.XA CN107129445A (en) | 2017-06-07 | 2017-06-07 | A kind of synthetic method of diuron |
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| CN201710421976.XA CN107129445A (en) | 2017-06-07 | 2017-06-07 | A kind of synthetic method of diuron |
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3850986A (en) * | 1971-07-20 | 1974-11-26 | Du Pont | Solvent-free process for 3-(halophenyl)-1,1-dialkyl ureas |
| DE3940261A1 (en) * | 1989-12-06 | 1991-06-13 | Agrolinz Agrarchemikalien Muen | Prodn. of di:substd. urea herbicides and fungicides, e.g. fenuron - by reacting amine with N-alkyl- or N,N-di:alkyl-urea in presence of corresp. alkyl- or di:alkylamine |
| 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 |
| CN102746194A (en) * | 2012-07-19 | 2012-10-24 | 江苏扬农化工集团有限公司 | Industrial production method for continuously preparing Dailon |
| CN103539704A (en) * | 2013-11-08 | 2014-01-29 | 江苏安邦电化有限公司 | Method for preparing diuron |
| CN104496855A (en) * | 2015-01-05 | 2015-04-08 | 山东润博生物科技有限公司 | Method for preparing diuron |
| CN105001123A (en) * | 2015-06-29 | 2015-10-28 | 安徽广信农化股份有限公司 | Cold synthesis technology of diuron |
| CN105017087A (en) * | 2015-06-29 | 2015-11-04 | 安徽广信农化股份有限公司 | Pretreatment technology for diuron recovered solvent |
| CN105294503A (en) * | 2015-10-20 | 2016-02-03 | 安徽广信农化股份有限公司 | Technology for purifying diuron |
-
2017
- 2017-06-07 CN CN201710421976.XA patent/CN107129445A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3850986A (en) * | 1971-07-20 | 1974-11-26 | Du Pont | Solvent-free process for 3-(halophenyl)-1,1-dialkyl ureas |
| DE3940261A1 (en) * | 1989-12-06 | 1991-06-13 | Agrolinz Agrarchemikalien Muen | Prodn. of di:substd. urea herbicides and fungicides, e.g. fenuron - by reacting amine with N-alkyl- or N,N-di:alkyl-urea in presence of corresp. alkyl- or di:alkylamine |
| 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 |
| CN102746194A (en) * | 2012-07-19 | 2012-10-24 | 江苏扬农化工集团有限公司 | Industrial production method for continuously preparing Dailon |
| CN103539704A (en) * | 2013-11-08 | 2014-01-29 | 江苏安邦电化有限公司 | Method for preparing diuron |
| CN104496855A (en) * | 2015-01-05 | 2015-04-08 | 山东润博生物科技有限公司 | Method for preparing diuron |
| CN105001123A (en) * | 2015-06-29 | 2015-10-28 | 安徽广信农化股份有限公司 | Cold synthesis technology of diuron |
| CN105017087A (en) * | 2015-06-29 | 2015-11-04 | 安徽广信农化股份有限公司 | Pretreatment technology for diuron recovered solvent |
| CN105294503A (en) * | 2015-10-20 | 2016-02-03 | 安徽广信农化股份有限公司 | Technology for purifying diuron |
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Application publication date: 20170905 |
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