CN101475514A - Process for synthesizing ryzalin by trichloromethyl carbonate method - Google Patents
Process for synthesizing ryzalin by trichloromethyl carbonate method Download PDFInfo
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- CN101475514A CN101475514A CNA2008101811215A CN200810181121A CN101475514A CN 101475514 A CN101475514 A CN 101475514A CN A2008101811215 A CNA2008101811215 A CN A2008101811215A CN 200810181121 A CN200810181121 A CN 200810181121A CN 101475514 A CN101475514 A CN 101475514A
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- Prior art keywords
- dinitrobenzene
- oryzalin
- technology
- dipropyl amido
- trichloromethyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 title abstract description 4
- LAYPMCGIWDGYKX-UHFFFAOYSA-N trichloromethyl hydrogen carbonate Chemical compound OC(=O)OC(Cl)(Cl)Cl LAYPMCGIWDGYKX-UHFFFAOYSA-N 0.000 title description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 32
- -1 trichloromethyl carbonic ether Chemical compound 0.000 claims abstract description 31
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 16
- 239000005587 Oryzalin Substances 0.000 claims abstract description 15
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 239000012442 inert solvent Substances 0.000 claims abstract description 11
- 229940077388 benzenesulfonate Drugs 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 229960001701 chloroform Drugs 0.000 claims description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical group [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 238000003786 synthesis reaction Methods 0.000 claims 5
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 1
- LCMAKIYHNGTOIR-UHFFFAOYSA-N OC(OC(Cl)(Cl)Cl)=O.Cl Chemical compound OC(OC(Cl)(Cl)Cl)=O.Cl LCMAKIYHNGTOIR-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 15
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract description 14
- 238000005516 engineering process Methods 0.000 abstract description 8
- 239000002351 wastewater Substances 0.000 abstract description 4
- 230000002363 herbicidal effect Effects 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 238000007098 aminolysis reaction Methods 0.000 abstract 2
- 238000005660 chlorination reaction Methods 0.000 abstract 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001514 detection method Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GKJROTAYDAJLGD-UHFFFAOYSA-N carbonyl dichloride;hydrochloride Chemical compound Cl.ClC(Cl)=O GKJROTAYDAJLGD-UHFFFAOYSA-N 0.000 description 1
- 238000013005 condensation curing Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to technology for synthesizing oryzalin by a trichloromethyl carbonic ether method, which relates to technology for synthesizing herbicide, namely the oryzalin. The technology is to take 3,5-binitro-4-di-n-propylamine benzene sulfonate as a raw material, use trichloromethyl carbonic ether to perform acyl chlorination in an inert solvent, and perform aminolysis to obtain crude oryzalin medicines. The innovation of the technology is to adopt the trichloromethyl carbonic ether instead of commonly used phosphorus oxychloride as an acyl chlorination agent, adopt dichloroethane to replace toluene, and finally use an ammonia liquid for direct aminolysis. The technology has the characteristics of cheap and easily obtained raw materials, safe, simple and convenient operation, high process yield, good product quality and small wastewater amount.
Description
Technical field:
The present invention relates to a kind of synthetic method of pesticide herbicide, specifically is to adopt 3, and 5-dinitrobenzene-4-dipropyl amido benzene sulfonate prepares the production technique of oryzalin, belongs to the pesticide chemical field.
Background technology:
Oryzalin (Oryzalin) is commonly called as oryzalin, chemical name 3, and 5-dinitrobenzene-4-dipropyl benzsulfamide is the principal item of dinitroaniline herbicide.The oryzalin industrial process has two, and one is to be starting raw material with the o-chloronitrobenzene, through chlorosulphonation, two nitrated, ammonia is separated, amination prepares; Because of the raw material costliness, the chlorsulfonic acid consumption causes cost higher greatly, and acid waste water waste gas is more, and equipment corrosion is serious.Another is starting raw material with the chlorobenzene, through oversulfonate, nitrated, saltout, amination, chloride, ammonia separate preparation; Though step is many, raw material is relatively inexpensive, and quantity of three wastes is less, production cost is lower.In the second production method, acyl chloride reaction is difficulty relatively, is the key of whole production technology, the chloride of originally industrial employing chlorsulfonic acid, and process recovery ratio is low, poor product quality, wastewater flow rate is big.German patent DE 3012800 has been reported a kind of excessive phosphorus oxychloride backflow of adopting, and reaction finishes the method that unreacted phosphorus oxychloride is deviate from the back redistillation, process recovery ratio height, good product quality; But the steaming of excessive phosphorus oxychloride removes waywardly in this patented method, if steam indivisiblely, when adding water washing, remaining phosphorus oxychloride is then acutely decomposed, and emits a large amount of heats and acid mist, causes material to splash, even causes towards the material accident; Remove excessively if steam, then can cause leftover materials condensation cure in the still, bonding still wall, stir the motionless electrical fault that causes.Since nineteen ninety, domestic production producer improves this, adopts toluene as solvent, 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonate and phosphorus oxychloride are reacted than 1:1.1～1.3 by amount of substance, steam phosphorus oxychloride after the reaction again, directly washing can overcome original shortcoming then.But because of intermediate 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonyl chloride is not high in the solubleness of toluene, often forms viscous pastes; And also hydrolysis easily of benzene sulfonyl chloride, yield is reduced, impurity increases.Therefore, the yield after the improvement has only about 90%, and the former medicine purity of finished product oryzalin has only 95%～96%.In addition, when ammonolysis reaction, use ammoniacal liquor can produce a large amount of orange factory effluents, seriously polluted.
Summary of the invention:
The objective of the invention is to overcome the shortcoming that exists in the existing production technique, provide easy and simple to handle a, safety and stability, wastewater flow rate few, and higher, the former medicine quality of process recovery ratio new production process preferably.
The method of synthetic ammonia nitralin of the present invention is characterized in that: earlier trichloromethyl carbonate (be commonly called as solid phosgene, be called for short BTC) and the inert solvent that measures dropped into reactor, the abundant stirring makes it to dissolve fully, gets solid phosgene solution.With 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonate and catalyzer drop into reactor again, add the inert solvent of metering, drip solid phosgene solution then while stirring; Drip Bi Jixu and stir insulation for some time, make chloride complete.Be warming up to backflow then, remove unreacted solid light.Be cooled to normal temperature at last, add the clear water of metering, controlled temperature feeds liquefied ammonia to neutral.Last suction filtration and thorough drying obtain the former medicine of oryzalin.
By oryzalin production technique of the present invention, the former medicine content of the oryzalin of gained is greater than 98%, with 3, and 5-dinitrobenzene-4-dipropyl amido benzene sulfonate meter, yield is greater than 92%.
Principle of the present invention is as follows.
The weight ratio of solid phosgene and inert solvent is 1:5～10 in the toluene solution of solid phosgene of the present invention.Described inert solvent is methylene dichloride, trichloromethane, ethylene dichloride or vinyl trichloride, the preferred the most honest and the cleanest ethylene dichloride of price.Described 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonate is sodium salt, sylvite, ammonium salt, is preferably sodium salt.Described catalyzer is tertiary amine, pyridine, methane amide, N, dinethylformamide (DMF) or N, and N-diethylformamide (DEF) is preferably DMF.
The amount of substance ratio of reactant of the present invention is: 3, and 5-dinitrobenzene-4-dipropyl amido benzene sulfonate/catalyzer/solid phosgene/liquefied ammonia=1/0.05～0.50/0.32～0.60/2.1～2.5.Described inert solvent weight is 1～5 times of total weight of material, and preferred optimum quantity is 3 times.The clear water that ammonia is separated adding is 0.5～3.5 times of total weight of material, is preferably 0.5 times.The chloride soaking time of indication is 1～5 hour, is preferably 2 hours.It is 0.5～3.0 hour that the BTC time is removed in the backflow of indication, is preferably 1 hour.
The present invention is a kind of production method of weedicide oryzalin, its innovative technology is the ammoniacal liquor that adopts the solid phosgene chloride, replaces lower concentration with alkyl chloride replacement toluene, with industrial liquefied ammonia, compare with domestic and international original production process, reaction conditions milder, process operation are safer, process recovery ratio improves, quality product is better, factory effluent still less, be fit to suitability for industrialized production.
Embodiment:
Embodiment 1
In the 250ml there-necked flask of electronic stirring was housed, the solid phosgene 12g of input 99.5% threw ethylene dichloride 60ml again, started and stirred, and fully stirred to make it to dissolve fully, got solid phosgene solution, was transferred in the dropping funnel then.In addition in the 500ml there-necked flask of electronic stirring, reflux condensing tube, thermometer is housed, drop into exsiccant 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt 36.9g (folding 100%), ethylene dichloride 100ml, start and stir 10min, make material dissolution, add the about 1.0g of DMF again, controlled temperature drips solid phosgene solution about 15 ℃.Drip to finish and under this temperature, continue stirring reaction 2h, then heat temperature raising backflow 1h.Be cooled to then below 10 ℃, add water 100ml, stir and feed liquefied ammonia down.Logical ammonia speed of control and water coolant make temperature of charge be no more than 50 ℃, are pH=8～9 until material acidity.Stop logical ammonia, insulation reaction 2h surveys material PH=8, branch vibration layer.Heating under vacuum removes ethylene dichloride to doing, and adds water 100ml, suction filtration behind the stirring 10min, and filter cake toasts 24h in 100 ℃ of baking ovens, get the dry thing 33.2g of orange.Pulverizing the back is 98.3% with the HPLC detection level, with 3, and 5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt meter, yield 94.32%.
Embodiment 2
Change inert solvent ethylene dichloride among the embodiment 1 into methylene dichloride, consumption is identical; All the other raw materials, operational condition are constant.Then obtain the dry powder 32.1g of orange, HPLC detection level 98.15%, with 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt meter, yield 91.06%.
Embodiment 3
Change inert solvent ethylene dichloride among the embodiment 1 into trichloromethane, consumption is identical; All the other raw materials, operational condition are constant.Then get the dry thing 31.8g of orange, HPLC detection level 98.24%, with 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt meter, yield 90.09%.
Embodiment 4
Change inert solvent ethylene dichloride among the embodiment 1 into vinyl trichloride, consumption is identical; All the other raw materials, operational condition are constant.Then get the dry powder 31.6g of orange, HPLC detection level 96.24%, with 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt meter, yield 87.89%.
Embodiment 5
Change catalyzer DMF among the embodiment 1 into DEF, consumption is identical; All the other are constant, then obtain the dry powder 32.7g of orange, HPLC detection level 98.43%, and with 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt meter, yield 93.02%.
Embodiment 6
With among the embodiment 13,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt 36.9g (folding 100%) changes 3 into, 5-dinitrobenzene-4-dipropyl amido Phenylsulfonic acid potassium 38.5g (folding 100%); All the other raw materials, operational condition are constant.Then obtain the dry powder 33.9g of orange, HPLC detection level 98.74%, with 3,5-dinitrobenzene-4-dipropyl amido Phenylsulfonic acid potassium meter, yield 92.81%.
Embodiment 7
With among the embodiment 13,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt 36.9g (folding 100%) changes 3 into, 5-dinitrobenzene-4-dipropyl amido ammonium benzene sulfonate 36.4g (folding 100%); All the other raw materials, operational condition are constant.Then obtain the dry powder 31.5g of orange, HPLC detection level 98.07%, with 3,5-dinitrobenzene-4-dipropyl amido ammonium benzene sulfonate meter, yield 89.28%.
Embodiment 8
In the 1000L enamel still, throwing ethylene dichloride 500L starts and stirs, and adds solid phosgene 125kg in batches, makes its dissolving fully, gets solid phosgene solution, is transferred to scale tank.
In 3000L enamel chuck still, drop into exsiccant 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt 385kg (content 96%), ethylene dichloride 990L (1158kg) starts and stirs, and adds DMF catalyzer 10kg again, open chilled brine and make temperature, drip solid phosgene solution below 10 ℃.The control rate of addition keeps temperature of reaction below 20 ℃.Drip Bi Jixu stirring reaction 4h, then open steam heating temperature rising reflux 1h.Be cooled to below 10 ℃, add water 1000L, begin to feed liquefied ammonia.Logical ammonia speed of control and water coolant make temperature of charge be no more than 50 ℃, and behind about 2h, drain has ammonia to emerge.Stop logical ammonia, continue insulation reaction 2h, survey material PH=9; Stop to stir, leave standstill 1h, tell lower floor's organic layer to still kettle, heating under vacuum removes ethylene dichloride to doing, and adds water 1000L, feeds the pressurized air press filtration after stirring 30min, and control pressure is at 0.4～0.5MPa, and filter cake is with 80 ℃ of dried blowing more than the 1h of warm air after the press filtration.Discharging then, transfer to moisture eliminator be dried to moisture below 0.2, crushing screening, orange powder 326kg.HPLC detection level 98.35%, with 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt meter, yield 92.66%.
Embodiment 9
Change catalyzer DMF10kg among the embodiment 1 into triethylamine 14kg, all the other are constant, then obtain the dry powder 320kg of orange, HPLC detection level 98.66%, and with 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonic acid sodium salt meter, yield 91.25%.
Claims (4)
1, a kind of synthesis technique of weedicide oryzalin is characterized by: in inert solvent, and through catalyst, raw material 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonate is by the trichloromethyl carbonate chloride.Obtain 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonyl chloride intermediate.In the presence of less water, intermediate 3,5-dinitrobenzene-4-dipropyl amido benzene sulfonyl chloride is separated at lesser temps ammonia, obtains 3,5-dinitrobenzene-4-dipropyl amido benzsulfamide, i.e. former medicine of oryzalin.
2, synthesis technique according to claim 1 is characterized in that described raw material 3, and 5-dinitrobenzene-4-dipropyl amido benzene sulfonate is that sodium salt is sylvite or ammonium salt, is preferably sodium salt.Described catalyzer is triethylamine or methane amide or N, dinethylformamide or N, and N-diethylformamide or pyridine are preferably N, dinethylformamide.
3, synthesis technique according to claim 1 is characterized in that described inert solvent is ethylene dichloride or trichloromethane or methylene dichloride or trichloroethane, is preferably ethylene dichloride; Its consumption is 3～5 times of material gross weight.
4, synthesis technique according to claim 1 is characterized in that proportioning raw materials is that amount of substance is than being 1:0.05～0.50:0.32～0.60:2.1～2.5 in the described synthesis technique.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351751A (en) * | 2011-08-12 | 2012-02-15 | 温州大学 | Method for chemically synthesizing 2-chloro-5-nitro-benzenesulfonyl chloride |
| CN103351385A (en) * | 2013-06-28 | 2013-10-16 | 浙江燎原药业有限公司 | Preparation method for rivaroxaban intermediate |
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2008
- 2008-11-25 CN CN2008101811215A patent/CN101475514B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351751A (en) * | 2011-08-12 | 2012-02-15 | 温州大学 | Method for chemically synthesizing 2-chloro-5-nitro-benzenesulfonyl chloride |
| CN103351385A (en) * | 2013-06-28 | 2013-10-16 | 浙江燎原药业有限公司 | Preparation method for rivaroxaban intermediate |
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| Publication number | Publication date |
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| CN101475514B (en) | 2012-06-13 |
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