CN102617407A - Method for preparing weedicide diuron - Google Patents
Method for preparing weedicide diuron Download PDFInfo
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- CN102617407A CN102617407A CN2012100564984A CN201210056498A CN102617407A CN 102617407 A CN102617407 A CN 102617407A CN 2012100564984 A CN2012100564984 A CN 2012100564984A CN 201210056498 A CN201210056498 A CN 201210056498A CN 102617407 A CN102617407 A CN 102617407A
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Abstract
The invention provides a method for preparing weedicide diuron. The method is characterized in that aromatic compound solvents are added in a reaction kettle, cooling and phosgene introduction are carried out, less dimethylformamide is added, 3, 4-dichloro phenylamine solution is dripped, and cocatalyst triethylene-diamine is added after the dripping completion; the temperature is raised to 80 to 100 DEG C, and the stirring is carried out under the heat insulation condition; solution consisting of 3, 4-dichloro phenyl isocyanate and the aromatic compound solvents is obtained through the reaction; and partial solvents are removed through evaporation, then, 40-percent dimethylamine is dripped, and dinitramine is prepared. Because the catalyst dimethylformamide and the cocatalyst triethylene-diamine are used in the reaction in the method provided by the invention, so the total yield of the synthesized dinitramine is higher than 91 percent, and the purity of the dinitramine raw medicine is higher than 99 percent. The synthesis process provided by the invention is more reasonable, the cost is low, the quality is high, a better environment-friendly effect is realized, the safety is higher, the international standard is reached, and the method is more suitable for industrialized production.
Description
Technical field
The present invention relates to a kind of preparation method of weedicide, particularly a kind of method for preparing herbicide Dailon.
Background technology
The English general Diuron by name of Diuron Tech, chemistry N-(3, the 4-dichlorophenyl) by name-N ', N '-dimethyl urea, CAS number is 330-54-1.Pure article are white crystalline solid.M.p. 158～159 ℃, vapour pressure 4.13 * 10
-4Pa (50 ℃).Be soluble in hot alcohol; In the time of 27 ℃, solubleness is 5.3% in acetone; Be dissolved in dioxane, ETHYLE ACETATE, ethanol and hot benzene slightly; In the time of 25 ℃ in water solubleness 42mg/L.Stable in the air, be heated to 180～190 ℃ of decomposition, meet strong acid, the easy decomposition of highly basic, non-corrosiveness, nonflammable.Industrial goods m.p.>150 ℃.
Diuron Tech is phenyl ureagroup herbicides, is used to prevent and kill off the general weeds of bare place, also is used for the cotton field selective herbicidal.Inhale conduction and certain action of contace poison in having.Medicament is absorbed back inhibition photosynthesis by root system of plant or blade, causes leaf chlorosis, and blade tip and edge fade, and cause plant nutrition for want of and death.Diuron Tech can select to carry out weeding through the potential difference and the time difference under low dosage.Become steriland herbicide during high dosage.Be mainly used in crops such as cotton, soybean, tomato, tobacco, strawberry, peanut, Chinese sorghum, corn, sugarcane, mulberry field, tea place, grape, orchard, rubber plantation and prevent and kill off annual gramineous weed and some broadleaf weeds; Like non-irrigated barnyard grass, lady's-grass, Herba Setariae Viridis, wild amaranth grass, nutgrass flatsedge, lamb's-quarters, Herba Eleusines Indicae, amaranth, knotweed, nutgrass flatsedge etc., the control of Herba potamogetonis distincti, Herba Marsileae Quadrifoliae, fescue etc. in the paddy rice; Also can be used for preventing and kill off of live cucumber field weed, and can be used for bare place and do total weed control.Before after the cotton field is broadcast, emerging, with 25% Diuron Tech wettable powder, 30～45g/100m2, to water 7.5kg, even spraying soil table, preventive effect is more than 90%; Be used for rice terrace and prevent and kill off Herba potamogetonis distincti with 7.5～15g/100m
2, preventive effect is more than 90%; Fruit tree, tea place are in weeds rudiment peak period, with 25% wettable powder, 30～37.5g/100m
2,, also can behind intertill and clean tillage, carry out the soil spraying and handle water 5.3kg spraying soil table.
The catalyzer that the preparation method of Diuron Tech of the prior art uses is unreasonable, makes its synthesis yield lower, and preparing method's cost is high.
Summary of the invention
Technical problem to be solved by this invention is the deficiency to prior art, and the method for preparing Diuron Tech that a kind of technology is more reasonable, cost is low, yield is high is provided.
Technical problem to be solved by this invention is to realize through following technical scheme.The present invention is a kind of method for preparing herbicide Dailon, is characterized in:
(1) exhaust treatment system being housed, stirring, have in the reaction kettle of prolong, ventpipe, TM, adds an amount of aromatic compound solvent, be cooled to-15～-30 ℃, fed phosgene 0.5 ~ 2.0 hour; Stop cooling, add the appropriate amount of catalysts N; Continue logical phosgene simultaneously, and slowly splash into 3, the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent are formed, along with the carrying out of reaction, temperature natural slowly rises to 20 ℃, and in 20～50 ℃, 0.5 ~ 2.0 hour, dropwises; Drip off the back 20～50 ℃ of following insulated and stirred 0.4～1.0 hour, stop logical phosgene; Add the solution that an amount of promotor triethylene diamine aromatic compound solvent is formed again; Slowly be heated to 90～100 ℃, be incubated 2.0 ~ 4.0 hours; Feed nitrogen, purge and remove remaining phosgene and hydrogen chloride gas, be cooled to 30～60 ℃; Behind the elimination insolubles, vacuum tightness-more than the 0.098MPa, slough in the feed liquid partly solvent, 3, the solution of 4-dichlorophenyl isocyanate and aromatic compound solvent composition;
(2) in reaction kettle, add above-mentioned gained 3, the solution that 4-dichlorophenyl isocyanate and aromatic compound solvent are formed with prolong, TM; Drip 40% dimethylamine agueous solution, 3, the mol ratio of 4-dichlorophenyl isocyanate and n n dimetylaniline is 1.00:1.00 ~ 1.15; 0.5 dropwised in～3.0 hours, temperature rises to 35 ~ 50 ℃ voluntarily, reacts 2 ~ 3 hours; The pH value is 7～8, is cooled to 0 ~ 10 ℃, centrifuging then.Filter cake reclaims solvent with aromatic compound solvent rinsing a small amount of 0 ~ 10 ℃, same as described above once, and the filter cake washing makes Diuron Tech to being neutral back in 90～100 ℃ of dryings; Raw material 3, the mol ratio of 4-dichlorphenamide bulk powder and n n dimetylaniline are 1:1.00 ~ 1.30.
In the method and technology scheme of above-described preparation herbicide Dailon: 3, in the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent are formed, 3, the mass ratio of 4-dichlorphenamide bulk powder and aromatic compound solvent can be selected on demand, is preferably 1:3～11.Described aromatic compound solvent can be for disclosed any applicable to aromatic compound solvent of the present invention in the prior art, preferred chlorobenzene, YLENE or toluene.
Principal reaction equation of the present invention is:
Compared with prior art, because the inventive method has been used two kinds of catalyzer Ns and promotor triethylene diamine in reaction, make the total recovery of synthesizing napropamide more than 91%, and the purity of the former medicine of napropamide is more than 99%.Synthesis technique of the present invention is more reasonable, and it is low to have a cost, and quality is high, and is more friendly, safer to environment, reached international standard, is more suitable in suitability for industrialized production.
Embodiment
Below further describe concrete technical scheme of the present invention,, and do not constitute restriction its right so that those skilled in the art understands the present invention further.
Embodiment 1, a kind of method for preparing herbicide Dailon, and its concrete steps are following:
(1) exhaust treatment system being housed, stirring, have in the reaction kettle of prolong, ventpipe, TM, adds an amount of aromatic compound solvent, be cooled to-15 ℃, fed phosgene 0.5 hour; Stop cooling, add the appropriate amount of catalysts N; Continue logical phosgene simultaneously, and slowly splash into 3, the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent are formed, along with the carrying out of reaction, temperature slowly rises to 20 ℃, and in 20～50 ℃, 0.5 ~ 2.0 hour, dropwises; Drip off the back 20 ℃ of following insulated and stirred 0.4 hour, stop logical phosgene; Add an amount of promotor triethylene diamine aromatics same as described above again and form solution; Slowly be heated to 90 ℃, be incubated 4 hours, insulation is finished, and feeds nitrogen, purges and removes remaining phosgene and hydrogen chloride gas, is cooled to 30 ℃; Behind the elimination insolubles, more than vacuum tightness-0.098MPa, slough in the feed liquid partly solvent, 3, the solution of 4-dichlorophenyl isocyanate and aromatic compound solvent composition;
(2) in reaction kettle, add above-mentioned gained 3, the solution that 4-dichlorophenyl isocyanate and aromatic compound solvent are formed with prolong, TM; Drip 40% dimethylamine agueous solution (mol ratio of dichlorobenzene isocyanic ester and n n dimetylaniline is 1.00:1.00), dropwised in 1.0 hours, temperature rises to 50 ℃ voluntarily; Reacted 2 hours; The pH value is 7～8, is cooled to 0 ~ 10 ℃, centrifuging then.Filter cake reclaims solvent with aromatic compound solvent rinsing a small amount of 0 ~ 10 ℃, same as described above once, and the filter cake washing is neutral back in 90 ℃ of dryings, makes Diuron Tech.
Embodiment 2, a kind of method for preparing herbicide Dailon, and its concrete steps are following:
(1) exhaust treatment system being housed, stirring, have in the reaction kettle of prolong, ventpipe, TM, adds an amount of aromatic compound solvent, be cooled to-30 ℃, fed phosgene 2.0 hours; Stop cooling, add the appropriate amount of catalysts N; Continue logical phosgene simultaneously, and slowly splash into 3, the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent same as described above are formed, along with the carrying out of reaction, temperature slowly rises to 20 ℃, and in 20～50 ℃, 0.5 ~ 2.0 hour, dropwises; Drip off the back 50 ℃ of following insulated and stirred 1.0 hours, stop logical phosgene; Add an amount of promotor triethylene diamine aromatics same as described above again and form solution; Slowly be heated to 100 ℃, be incubated 4.0 hours; Feed nitrogen, purge and remove remaining phosgene and hydrogen chloride gas, be cooled to 60 ℃; Behind the elimination insolubles, more than vacuum tightness-0.098MPa, slough in the feed liquid partly solvent, 3, the solution of 4-dichlorobenzene isocyanic ester and aromatic compound solvent composition;
(2) in reaction kettle, add above-mentioned gained 3, the solution that 4-dichlorophenyl isocyanate and aromatic compound solvent same as described above are formed with prolong, TM; Drip 40% dimethylamine agueous solution (mol ratio of dichlorobenzene isocyanic ester and n n dimetylaniline is 1.00:1.15), dropwised in 3.0 hours, temperature rises to 35 ℃ voluntarily; Reacted 3 hours; The pH value is 7～8, is cooled to 0 ~ 10 ℃, centrifuging then.Filter cake reclaims solvent with aromatic compound solvent rinsing a small amount of 0 ~ 10 ℃, same as described above once, and the filter cake washing is neutral back in 95 ℃ of dryings, makes Diuron Tech.
Embodiment 3, and in embodiment 1 or the 2 described methods that prepare herbicide Dailon: raw material 3, the mass ratio of 4-dichlorphenamide bulk powder and n n dimetylaniline are 1:1.00.
Embodiment 4, and in embodiment 1 or the 2 described methods that prepare herbicide Dailon: raw material 3, the mass ratio of 4-dichlorphenamide bulk powder and n n dimetylaniline are 1:1.15;
Embodiment 5, and in embodiment 1 or the 2 described methods that prepare herbicide Dailon: raw material 3, the mass ratio of 4-dichlorphenamide bulk powder and n n dimetylaniline are 1:1.3.
Embodiment 6, in any one described method for preparing herbicide Dailon of embodiment 1-5: 3, in the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent are formed, 3, the mass ratio of 4-dichlorphenamide bulk powder and aromatic compound solvent is 1:3.
Embodiment 7, in any one described method for preparing herbicide Dailon of embodiment 1-5: 3, in the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent are formed, 3, the mass ratio of 4-dichlorphenamide bulk powder and aromatic compound solvent is 1:8.
Embodiment 8, in any one described method for preparing herbicide Dailon of embodiment 1-5: 3, in the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent are formed, 3, the mass ratio of 4-dichlorphenamide bulk powder and aromatic compound solvent is 1:11.
Embodiment 9, and in any one described method for preparing herbicide Dailon of embodiment 1-8: described aromatic compound solvent is chlorobenzene, YLENE or toluene.
Embodiment 10.The method experiment one for preparing herbicide Dailon.
Exhaust treatment system is being housed, is stirring, have in the 500ml four-hole bottle of prolong, ventpipe, TM, adding the 100.0g chlorobenzene, be cooled to-15～-30 ℃, feeding phosgene 1.0 hours; Remove cryostat, add a little catalyzer DMF, logical simultaneously phosgene; And slowly splashing into 29.5g3, the solution that 4-dichlorphenamide bulk powder and 300 g chlorobenzenes are formed is along with the carrying out of reaction; Temperature natural rises to 30 ℃; And under 30～50 ℃ of temperature, dropwised in 1.0 ~ 1.5 hours, drip off 50 ℃ of following insulated and stirred 0.5 hour, stop logical light.Add a little promotor triethylene diamine chlorobenzene solution; Slowly be heated to 90～110 ℃, be incubated 3 hours, feed liquid is transparence.After insulation finishes, feed nitrogen, purge and remove remaining phosgene and hydrogen chloride gas, be cooled to 40～50 ℃; Behind a small amount of insolubles of elimination, more than vacuum tightness-0.098MPa, slough the half the chlorobenzene of feed liquid gross weight, computation weigh, detect 3, the content of 4-dichlorophenyl isocyanate is with subsequent use.
In having the 500ml four-hole bottle of prolong, TM, add above-mentioned gained 3, the chlorobenzene solution of 4-dichlorophenyl isocyanate and 80g chlorobenzene stir and drip 40% n n dimetylaniline, 20.3 g down; Dropwised in about 1.5 hours, and be warming up to 50 ℃ naturally, be incubated 2 hours; Then be warming up to 120 ℃, be incubated 7.0 hours, be cooled to 0 ℃ subsequently; Filter, filter cake with a small amount of 0 ~ 10 ℃ chlorobenzene rinsing once, dry must napropamide 39.1g; It is 99.1% that HPLC analyzes content, with 3, and 4-dichlorphenamide bulk powder meter total recovery 92.5%.
Embodiment 11, prepare the method experiment two of herbicide Dailon.
Exhaust treatment system is housed, stirs, have prolong, in the ventpipe, TM 500ml four-hole bottle, adding 80.0g toluene, be cooled to-15～-30 ℃, fed phosgene 1.0 hours; Remove cryostat, add the catalyzer DMF of a little, logical simultaneously phosgene; And slowly splashing into 29.5g3, the solution that 4-dichlorphenamide bulk powder and 250 g toluene are formed is along with the carrying out of reaction; Temperature natural rises to 30 ℃; And under 30～50 ℃ of temperature, dropwised in 1.0 ~ 1.5 hours, drip off 50 ℃ of following insulated and stirred 0.5 hour, stop logical light.Add a little promotor triethylene diamine toluene solution, slowly be heated to 90～100 ℃, be incubated 3 hours, feed liquid is transparence.After insulation finishes, feed nitrogen, purge and remove remaining phosgene and hydrogen chloride gas, be cooled to 40～50 ℃; Behind a small amount of insolubles of elimination, more than vacuum tightness-0.098MPa, slough the half the toluene of feed liquid gross weight, computation weigh, detect 3, the content of 4-dichlorophenyl isocyanate is with subsequent use.
In having prolong, TM 500ml four-hole bottle, add 80g toluene, stir adding n n dimetylaniline 22.3g down, be warming up to backflow; Drip above-mentioned gained 3,4-dichlorophenyl isocyanate toluene solution dropwised in about 1.5 hours, dripped off continued and refluxed 7.0 hours; Then be cooled to 0 ℃, filter, filter cake with a small amount of 0 ~ 10 ℃ toluene rinsing once, dry must napropamide 38.7g; It is 99.5% that HPLC analyzes content, with 3, and 4-dichlorphenamide bulk powder meter total recovery 91.8%.
Embodiment 12, prepare the method experiment three of herbicide Dailon.
Exhaust treatment system is housed, stirs, have prolong, in the ventpipe, TM 500ml four-hole bottle, adding 80.0g YLENE, be cooled to-15～-30 ℃; Fed phosgene 1.0 hours, and removed cryostat, add a little and (can be 3; 4-dichlorphenamide bulk powder quality 1～5%) catalyzer DMF (being N), logical simultaneously phosgene, and slowly splash into 29.5g3; The solution that 4-dichlorphenamide bulk powder and 250 g YLENE are formed, along with the carrying out of reaction, temperature natural rises to 30 ℃; And under 30～50 ℃ of temperature, dropwised in about 1 hour, drip off 50 ℃ of following insulated and stirred 0.5 hour, stop logical light.Add a little promotor triethylene diamine xylene solution, slowly be heated to 90～100 ℃, be incubated 3 hours, feed liquid is transparence.After insulation finishes, feed nitrogen, purge and remove remaining phosgene and hydrogen chloride gas; Be cooled to 40～50 ℃, behind a small amount of insolubles of elimination, more than vacuum tightness-0.098MPa, slough the half the YLENE of feed liquid gross weight; Computation weigh, detection 3,4-dichlorophenyl isocyanate content is with subsequent use.
In having the 500ml four-hole bottle of prolong, TM, add 80g YLENE, stir adding n n dimetylaniline 23.3g down; Be warming up to 120 ℃, drip above-mentioned gained 3,4-dichlorophenyl isocyanate xylene solution; Dropwised in about 1.5 hours, and dripped off continued and about 120～130 ℃, be incubated 7.0 hours, then be cooled to 0 ℃; Filter, filter cake with a small amount of 0 ~ 10 ℃ YLENE rinsing once, dry must napropamide 38.9g; It is 99.2% that HPLC analyzes content, with 3, and 4-dichlorphenamide bulk powder meter total recovery 92.0%.
Among the embodiment 10-12, the midbody of napropamide and check analysis method are following.
(1) midbody---3,4-dichlorobenzene isocyanic ester.
Analytical procedure: GC marker method.
Instrument model: GC-9790, chromatographic column: SE-54, the column compartment temperature: 150 ℃, temperature of vaporization chamber: 250 ℃, sensing chamber's temperature: 250 ℃, press before the post: 0.04MPa, internal standard substance; Dimethyl phthalate.Sample is with the chlorobenzene dissolving that is preheated to 30 ℃.
(2) finished product---napropamide is quantitative.
Analytical procedure: HPLC external standard method.
Wavelength 254nm, flow velocity 1.0ml/min, moving phase: methyl alcohol: water=80:20; Take by weighing 0.05 gram sample in the 50ml volumetric flask, dissolve appearance, add 10ml DMF in volumetric flask with methyl alcohol; Add to 50ml with methyl alcohol; Ultrasonic oscillation 5 minutes pipettes in 2 ml appearance liquid to the 25 ml volumetric flasks, adds to 25 ml with moving phase.
Claims (3)
1. a method for preparing herbicide Dailon is characterized in that, its concrete steps are following:
(1) exhaust treatment system being housed, stirring, have in the reaction kettle of prolong, ventpipe, TM, adds the solvent of an amount of aromatics, be cooled to-15～-30 ℃, fed phosgene 0.5 ~ 2.0 hour; Stop cooling, add the appropriate amount of catalysts N; Continue logical phosgene simultaneously, and slowly splash into 3, the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent are formed, along with the carrying out of reaction, temperature slowly rises to 20 ℃, and in 20～50 ℃, 0.5 ~ 2.0 hour, dropwises; Drip off the back 20～50 ℃ of following insulated and stirred 0.4～1.0 hour, stop logical phosgene; Slowly be heated to 90～100 ℃, add the solution that an amount of promotor triethylene diamine and aromatic compound solvent same as described above are formed again; Be incubated 2.0 ~ 4.0 hours; Feed nitrogen, purge and remove remaining phosgene and hydrogen chloride gas, be cooled to 30～60 ℃; Behind the elimination insolubles, more than vacuum tightness-0.098MPa, slough in the feed liquid partly solvent, 3, the solution of 4-dichlorophenyl isocyanate and aromatic compound solvent composition;
(2) in reaction kettle with prolong, TM, stir the above-mentioned gained 3 of adding down, the solution that 4-dichlorophenyl isocyanate and aromatic compound solvent are formed drips 40% dimethylamine agueous solution; 3, the mol ratio of 4-dichlorophenyl isocyanate and n n dimetylaniline is that 1.00:1.00 ~ 1.15,0.5～3.0 hour dropwise; Temperature rises to 35 ~ 50 ℃ voluntarily, reacts 2 ~ 3 hours, and the pH value is 7～8; Be cooled to 0 ~ 10 ℃, centrifuging then, filter cake is with aromatic compound solvent rinsing a small amount of 0 ~ 10 ℃, same as described above once; Reclaim solvent, the filter cake washing makes Diuron Tech to being neutral back in 90～100 ℃ of dryings; Raw material 3, the mol ratio of 4-dichlorphenamide bulk powder and n n dimetylaniline are 1:1.0～1.3.
2. the method for preparing herbicide Dailon according to claim 1 is characterized in that: 3, and in the solution that 4-dichlorphenamide bulk powder and aromatic compound solvent are formed, 3, the mass ratio of 4-dichlorphenamide bulk powder and aromatic compound solvent is 1:3～11.
3. the method for preparing herbicide Dailon according to claim 1 and 2 is characterized in that: described aromatic compound solvent is chlorobenzene, YLENE or toluene.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103351385A (en) * | 2013-06-28 | 2013-10-16 | 浙江燎原药业有限公司 | Preparation method for rivaroxaban intermediate |
| 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 |
| CN105294504A (en) * | 2015-10-20 | 2016-02-03 | 安徽广信农化股份有限公司 | Method for synthesizing diuron |
| 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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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103351385A (en) * | 2013-06-28 | 2013-10-16 | 浙江燎原药业有限公司 | Preparation method for rivaroxaban intermediate |
| 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 |
| CN105294504A (en) * | 2015-10-20 | 2016-02-03 | 安徽广信农化股份有限公司 | Method for synthesizing diuron |
| CN105294503A (en) * | 2015-10-20 | 2016-02-03 | 安徽广信农化股份有限公司 | Technology for purifying diuron |
| CN105294503B (en) * | 2015-10-20 | 2017-09-12 | 安徽广信农化股份有限公司 | A kind of purifying technique of diuron |
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