CN113563347A - Purification method of penoxsulam technical - Google Patents
Purification method of penoxsulam technical Download PDFInfo
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- CN113563347A CN113563347A CN202110956310.0A CN202110956310A CN113563347A CN 113563347 A CN113563347 A CN 113563347A CN 202110956310 A CN202110956310 A CN 202110956310A CN 113563347 A CN113563347 A CN 113563347A
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- 239000005592 Penoxsulam Substances 0.000 title claims abstract description 50
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000000746 purification Methods 0.000 title claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 53
- 239000000047 product Substances 0.000 claims abstract description 29
- 238000004537 pulping Methods 0.000 claims abstract description 23
- 238000003756 stirring Methods 0.000 claims abstract description 19
- 239000012065 filter cake Substances 0.000 claims abstract description 18
- 238000001914 filtration Methods 0.000 claims abstract description 18
- 229940079593 drug Drugs 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- -1 1-dichloroethane Chemical compound 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 10
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000002002 slurry Substances 0.000 description 7
- 239000004009 herbicide Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 4
- 241000192043 Echinochloa Species 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 108010000700 Acetolactate synthase Proteins 0.000 description 2
- 241000234646 Cyperaceae Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- DTNQLYAGRKNWMQ-UHFFFAOYSA-N 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)COC1=CC=CC(C(F)(F)F)=C1S(Cl)(=O)=O DTNQLYAGRKNWMQ-UHFFFAOYSA-N 0.000 description 1
- NGBMMSDIZNGAOK-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine-5-sulfonamide Chemical compound NS(=O)(=O)C1=NC=C2NN=NC2=N1 NGBMMSDIZNGAOK-UHFFFAOYSA-N 0.000 description 1
- DBJPBHJHAPAUQU-UHFFFAOYSA-N 5,8-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amine Chemical compound COC1=CN=C(OC)N2N=C(N)N=C12 DBJPBHJHAPAUQU-UHFFFAOYSA-N 0.000 description 1
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 description 1
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 description 1
- 239000005472 Bensulfuron methyl Substances 0.000 description 1
- 241001553700 Euphorbia lathyris Species 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004557 technical material Substances 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Abstract
The invention discloses a purification method of penoxsulam technical, which comprises the following steps: step 1: adding the crude penoxsulam into a solvent, heating to 20-150 ℃ under the stirring condition, and maintaining for 1.0-12 hours; step 2: adding or not adding a solvent, slowly cooling to-10-30 ℃, filtering when the product is completely separated out, and taking a filter cake; and step 3: adding the filter cake into a solvent, stirring and pulping; and 4, step 4: filtering and drying to obtain the purified penoxsulam technical product. According to the invention, through the selection of the penoxsulam purification method, the proportion of main impurities can be reduced, the purity of the original drug is effectively improved, the purity of the penoxsulam original drug purified by the technology is not lower than 98.5%, the content of the impurities is greatly reduced, and the problem of low purity commonly existing in the industry is solved. Meanwhile, the technical scheme of the invention is very easy to operate, has relatively low purification cost and is beneficial to industrial production.
Description
Technical Field
The invention relates to the technical field of pesticide production, and particularly relates to a purification method of penoxsulam technical.
Background
Penoxsulam is a triazolopyrimidine sulfonamide herbicide developed by the Dow Yinong company, USA, and plays a role in weeding by inhibiting acetolactate synthase. The herbicide belongs to a conductive herbicide, is absorbed by stem leaves, buds and root systems, is conducted to meristems through xylem and phloem to inhibit plant growth, so that growing points lose green, terminal buds turn red and are necrotic after treatment for 7-14 days, and plants die after 2-4 weeks; the agent is a strong acetolactate synthase inhibitor, is slow in appearance, and gradually dies after a certain time. The penoxsulam is suitable for direct seeding dry land, direct seeding water land, seedling land and seedling throwing and transplanting cultivation land of rice. Directly sowing the seedlings in the dry land before germination or after irrigation, applying the seedlings directly sown in water in the early stage after seedling planting, and applying the pesticide 5-7 days after seedling planting. The application method can be spraying or soil mixing treatment. Penoxsulam is a broad-spectrum herbicide for paddy fields, can effectively control barnyard grass (including barnyard grass with resistance to propanil, quinclorac and acetyl coenzyme A carboxylase), moleplant seed and annual cyperaceae weeds, and is effective on a plurality of broadleaf weeds. The lasting period is as long as 30-60 days, and the harm of weeds in all seasons can be basically controlled by one-time application. Meanwhile, the herbicide can prevent and kill bensulfuron methyl weeds in rice fields, has residual activity on a plurality of broadleaf and cyperaceae weeds, barnyard grass and the like, and is a variety with the widest weed control spectrum in the current herbicides for the rice fields.
The amine synthesis route of penoxsulam can be divided into a first bridge method and a rear bridge method, and the synthesis route of the rear bridge method is as follows: the method comprises the steps of taking uracil as an initial raw material, preparing an intermediate 2-amino-5, 8-dimethoxy (1, 2, 4) triazolo [1.5-C ] pyrimidine through chlorination, hydrazinization, cyclization and transposition, and reacting the intermediate with 2- (2, 2-difluoroethoxy) -6-trifluoromethylbenzenesulfonyl chloride to obtain a target product, namely penoxsulam. Because the amidation reaction material is not completely dissolved in the solvent and byproducts are generated, the product has a certain amount of impurities and is not easy to remove, so that the purity of the penoxsulam technical product is generally not high and is generally 92-95%, and the related standard cannot be met. In order to overcome the industrial problem, it is necessary to develop a purification method for purifying penoxsulam technical material to remove related impurities.
Disclosure of Invention
The invention aims to provide a method for purifying a penoxsulam technical product with low cost and good effect, so as to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme:
a purification method of penoxsulam technical comprises the following steps:
step 1: adding the crude penoxsulam into a solvent, heating to 20-150 ℃ under the stirring condition, and maintaining for 1.0-12 hours;
step 2: adding or not adding a solvent, slowly cooling to-10-30 ℃, filtering when the product is completely separated out, and taking a filter cake;
and step 3: adding the filter cake into a solvent, stirring and pulping;
and 4, step 4: filtering and drying to obtain the purified penoxsulam technical product.
The temperature is reduced to room temperature or below, the product solubility can be reduced by reducing the temperature, the product yield is improved, but impurities are separated out due to too low temperature, and the product purity is reduced. Different heating temperatures and precipitation temperatures are required according to different solvents. In the step 2, the addition or non-addition of the solvent means that other solvents can be not added, and an alcohol solvent, an ether solvent, a chlorine-containing solvent, an alkane solvent and a benzene ring-containing solvent can be added, so that the product is favorably precipitated. For example, in an alcohol solvent, by adding a proper amount of methyl tert-butyl ether, the solubility of the product is reduced, and the product is more easily precipitated. The pulping process in the step 4 is used for purifying by utilizing the characteristics that the solubility of a substance in a solvent is poor, but the solubility of impurities in the solvent is good, and the pulping process is mainly used for organic synthesis and pharmacy, and is finally used for purifying and purifying products to remove the impurities.
Further, in the step 1 and the step 3, the addition amount of the solvent is 1-100 mol of the solvent added to each mol of the crude penoxsulam drug.
Further, in the step 2, the addition amount of the solvent is 1-50 mol of the solvent added to each mol of the crude penoxsulam drug.
Further, the solvent is one selected from an alcohol solvent, an amide solvent, an ether solvent, an alkane solvent, a chlorine-containing solvent, a benzene ring-containing solvent, acetonitrile and N-methylpyrrolidone.
Further, the alcohol solvent is selected from one of methanol, ethanol, propanol, butanol, isopropanol, isobutanol, tert-butanol, ethylene glycol and propylene glycol.
Further, the amide solvent is selected from one of N, N-dimethylformamide and N, N-dimethylacetamide.
Further, the ether solvent is selected from one of diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1, 4-dioxane, 1, 2-dimethoxyethane and anisole.
Further, the alkane solvent is selected from one of petroleum ether, pentane, n-hexane, cyclohexane, octane and heptane.
Further, the chlorine-containing solvent is selected from one of methyl chloride, dichloromethane, trichloromethane, carbon tetrachloride, 1, 2-dichloroethane, 1-dichloroethane and chlorobenzene.
Further, the benzene-containing solvent is selected from one of benzene, toluene, xylene and phenol.
Compared with the prior art, the invention has the beneficial effects that: according to the invention, through the selection of a new purification method, the proportion of main impurities can be reduced, the purity of the raw pesticide is effectively improved, the purity of the raw pesticide of penoxsulam purified by the technology is not lower than 98.5%, the content of impurities is greatly reduced, and the problem of low purity commonly existing in the industry is solved. Meanwhile, the technical scheme of the invention is very easy to operate, has relatively low purification cost and is beneficial to industrial production.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
(1) Adding 50g of crude penoxsulam into 200mL of 99 wt% toluene, heating to 40 ℃ under stirring, and maintaining for 10 h;
(2) slowly cooling to 10 ℃, filtering when the product is completely separated out, and taking a filter cake;
(3) adding the filter cake into 150mL of trichloromethane, stirring and pulping, wherein the pulping temperature is 15 ℃, and the pulping time is 8 hours, so as to obtain a pulp;
(4) and filtering and drying the slurry to obtain a purified penoxsulam technical product.
Example 2
(1) Adding 50g of crude penoxsulam into 250mL of dimethylbenzene, heating to 150 ℃ under the condition of stirring, and maintaining for 1 h;
(2) adding 50mL of ethylene glycol dimethyl ether, slowly cooling to 10 ℃, filtering when the product is completely separated out, and taking a filter cake;
(3) adding the filter cake into 250mL of ethanol, stirring and pulping, wherein the pulping temperature is 25 ℃, and the pulping time is 3 hours, so as to obtain a pulp;
(4) and filtering and drying the slurry to obtain a purified penoxsulam technical product.
Example 3
(1) Adding 50g of crude penoxsulam into 150mL of tetrahydrofuran with the concentration of 99 wt%, heating to 40 ℃ under the stirring condition, and maintaining for 4 hours;
(2) adding 50mL of petroleum ether, stirring uniformly, slowly cooling to 0 ℃, filtering when the product is completely separated out, and taking a filter cake;
(3) adding the filter cake into 250mL of 1, 1-dichloroethane, stirring and pulping, wherein the pulping temperature is 25 ℃, and the pulping time is 5 hours, so as to obtain a pulp;
(4) and filtering and drying the slurry to obtain a purified penoxsulam technical product.
Example 4
(1) Adding 50g of crude penoxsulam into 200ml of DMF, heating to 45 ℃ under the stirring condition, and maintaining for 2 hours;
(2) slowly cooling to 10 ℃, filtering when the product is completely separated out, and taking a filter cake;
(3) adding the filter cake into 250mL of methanol, stirring and pulping, wherein the pulping temperature is 80 ℃, and the pulping time is 1h to obtain a pulp;
(4) and filtering and drying the slurry to obtain a purified penoxsulam technical product.
Example 5
(1) Adding 50g of crude penoxsulam into 200mL of acetonitrile, heating to 45 ℃ under the condition of stirring, and maintaining for 2 hours;
(2) slowly cooling to 0 ℃, and filtering to obtain a filter cake after the product is completely separated out;
(3) adding the filter cake into 200mL of ethanol, stirring and pulping, wherein the pulping temperature is 80 ℃, and the pulping time is 1h to obtain a pulp;
(4) and filtering and drying the slurry to obtain a purified penoxsulam technical product.
Example 6
(1) Adding 50g of crude penoxsulam into 200mL of ethylene glycol dimethyl ether, heating to 60 ℃ under the stirring condition, and maintaining for 6 hours;
(2) adding 50mL of phenol, slowly cooling to 5 ℃, filtering when the product is completely separated out, and taking a filter cake;
(3) adding the filter cake into 200mL of methylbenzene, stirring and pulping, wherein the pulping temperature is 15 ℃, and the pulping time is 8 hours, so as to obtain a slurry;
(4) and filtering and drying the slurry to obtain a purified penoxsulam technical product.
Comparative example: the comparative example used an unpurified crude penoxsulam.
The purities of the penoxsulam crude drug products purified in examples 1 to 6 and the penoxsulam crude drug of the comparative example were measured, and the results are shown in table 1:
TABLE 1 test results
As can be seen from the table 1, the purity of the penoxsulam technical purified by the technology is not lower than 98.5%, compared with the crude penoxsulam technical, the purity is obviously improved, the content of impurities is greatly reduced, and the problem of low purity commonly existing in the industry is solved.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be able to cover the technical solutions and the inventive concepts of the present invention within the technical scope of the present invention.
Claims (10)
1. A purification method of penoxsulam technical is characterized by comprising the following steps:
step 1: adding the crude penoxsulam into a solvent, heating to 20-150 ℃ under the stirring condition, and maintaining for 1.0-12 hours;
step 2: adding or not adding a solvent, slowly cooling to-10-30 ℃, filtering when the product is completely separated out, and taking a filter cake;
and step 3: adding the filter cake into a solvent, stirring and pulping;
and 4, step 4: filtering and drying to obtain the purified penoxsulam technical product.
2. The method for purifying a penoxsulam original drug according to claim 1, wherein in the step 1 and the step 3, the solvent is added in an amount of 1 to 100 moles per mole of crude penoxsulam original drug.
3. The method for purifying a penoxsulam original drug according to claim 1, wherein in the step 2, the solvent is added in an amount of 1 to 50 moles per mole of crude penoxsulam original drug.
4. The method for purifying a penoxsulam original drug according to claim 1, wherein the solvent is one selected from an alcohol solvent, an amide solvent, an ether solvent, an alkane solvent, a chlorine-containing solvent, a benzene ring-containing solvent, acetonitrile, and N-methylpyrrolidone.
5. The method of claim 4, wherein the alcoholic solvent is selected from the group consisting of methanol, ethanol, propanol, butanol, isopropanol, isobutanol, tert-butanol, ethylene glycol, and propylene glycol.
6. The method for purifying a penoxsulam original drug according to claim 4, wherein the amide solvent is one selected from N, N-dimethylformamide and N, N-dimethylacetamide.
7. The method for purifying penoxsulam as claimed in claim 4, wherein the ether solvent is selected from one of diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1, 4-dioxane, 1, 2-dimethoxyethane and anisole.
8. The method for purifying penoxsulam as claimed in claim 4, wherein the alkane solvent is selected from one of petroleum ether, pentane, n-hexane, cyclohexane, octane and heptane.
9. The method of claim 4, wherein the chlorine-containing solvent is selected from the group consisting of methyl chloride, methylene chloride, chloroform, carbon tetrachloride, 1, 2-dichloroethane, 1-dichloroethane, and chlorobenzene.
10. The method of claim 4, wherein the benzene-containing solvent is selected from the group consisting of benzene, toluene, xylene, and phenol.
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| CN104402890A (en) * | 2014-11-10 | 2015-03-11 | 常州大学 | Preparation method of penoxsulam |
| CN107021966A (en) * | 2017-04-11 | 2017-08-08 | 四川福思达生物技术开发有限责任公司 | The synthetic method of improved penoxsuam |
| CN107602567A (en) * | 2017-09-29 | 2018-01-19 | 湖北犇星农化有限责任公司 | A kind of method for synthesizing penoxsuam |
| CN108017617A (en) * | 2017-12-29 | 2018-05-11 | 绍兴上虞银邦化工有限公司 | A kind of purification process of rimsulfuron active compound |
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| CN104402890A (en) * | 2014-11-10 | 2015-03-11 | 常州大学 | Preparation method of penoxsulam |
| CN107021966A (en) * | 2017-04-11 | 2017-08-08 | 四川福思达生物技术开发有限责任公司 | The synthetic method of improved penoxsuam |
| CN107602567A (en) * | 2017-09-29 | 2018-01-19 | 湖北犇星农化有限责任公司 | A kind of method for synthesizing penoxsuam |
| CN108017617A (en) * | 2017-12-29 | 2018-05-11 | 绍兴上虞银邦化工有限公司 | A kind of purification process of rimsulfuron active compound |
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