CN115260110A - Green and efficient synthesis method of tebuconazole - Google Patents
Green and efficient synthesis method of tebuconazole Download PDFInfo
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- CN115260110A CN115260110A CN202210971325.9A CN202210971325A CN115260110A CN 115260110 A CN115260110 A CN 115260110A CN 202210971325 A CN202210971325 A CN 202210971325A CN 115260110 A CN115260110 A CN 115260110A
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- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 239000005839 Tebuconazole Substances 0.000 title claims abstract description 65
- 238000001308 synthesis method Methods 0.000 title claims abstract description 20
- 239000002608 ionic liquid Substances 0.000 claims abstract description 47
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000001816 cooling Methods 0.000 claims abstract description 13
- 238000004321 preservation Methods 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
- QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012071 phase Substances 0.000 claims description 37
- 239000007787 solid Substances 0.000 claims description 18
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 15
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 5
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 9
- 239000003513 alkali Substances 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000013341 scale-up Methods 0.000 abstract description 2
- KYCQOKLOSUBEJK-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;bromide Chemical compound [Br-].CCCCN1C=C[N+](C)=C1 KYCQOKLOSUBEJK-UHFFFAOYSA-M 0.000 description 5
- HBCNUSPKBMKRLV-UHFFFAOYSA-N 3-benzyl-1-methyl-1,2-dihydroimidazol-1-ium;chloride Chemical compound [Cl-].C1=CN(C)C[NH+]1CC1=CC=CC=C1 HBCNUSPKBMKRLV-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000721047 Danaus plexippus Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241000228453 Pyrenophora Species 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- -1 inorganic base potassium hydroxide Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- CAADOIDIOZIPES-UHFFFAOYSA-N pentalane Chemical compound C12C3C4C3CC1C4C1C2C1 CAADOIDIOZIPES-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Abstract
The invention discloses a green and efficient synthesis method of tebuconazole, which comprises the following steps: step one, preparing raw materials; step two, reacting raw materials; step three, standing and phase splitting; step four, cooling; step five, obtaining a tebuconazole finished product; in the first step, the ionic liquid is selected from any one or more of the following combinations: imidazole ionic liquid, pyridine ionic liquid, pyrrolidine ionic liquid, morpholine ionic liquid and piperidine ionic liquid; in the second step, the weight of the ionic liquid is 0.1-2 times of that of the pentone oxygen; in the second step, the heat preservation temperature is 80-110 ℃, and the heat preservation time is 1-5h; compared with the existing tebuconazole preparation method, the reaction conditions are simpler, the tebuconazole with high yield and high purity can be directly synthesized without other solvents and alkali, and additional alkali catalysts and phase transfer catalysts are not needed, so that the method is greener in process, reduces the environmental protection pressure, and is suitable for industrial scale-up production.
Description
Technical Field
The invention relates to the technical field of bactericides, in particular to a green and efficient synthesis method of tebuconazole.
Background
Tebuconazole is a high-efficiency, broad-spectrum and low-toxicity triazole bactericide developed by German Bayer company in 1986, is widely applied globally, and has the functions of protection, treatment, eradication and the like. Tebuconazole is mainly used as a seed treatment agent and foliar spray to prevent and treat various fungal diseases of crops such as wheat, rice, peanut, vegetables, banana, apple and the like, and can effectively prevent and treat diseases caused by ustilago, puccinia, pyrenophora, septoria and the like, such as powdery mildew, root rot, smut, various rust diseases and the like of cereal crops. Tebuconazole has great economic and social benefits, and the development, production and optimization of the synthesis process thereof are very necessary.
The synthesis method reported in the literature at present uses pentosan oxygen and 1,2, 4-triazole as raw materials to synthesize tebuconazole, and the synthesis process of tebuconazole as a novel bactericide (Anhui agricultural science, 2007, 35 (1), 144-192), which is reported by Huang Xinhui et al, discloses a synthesis method of tebuconazole, which adopts cyclohexanol as a solvent, and heats to 150 ℃ and preserves the temperature for 20 hours, wherein the yield of tebuconazole is 53.8%; also, as reported by Ganren monarch, "synthesis of tebuconazole and control effect thereof on wheat sharp eyespot" (Master thesis of Chinese agriculture university, 2002), in the research thesis, n-butanol is adopted as solvent, potassium hydroxide is adopted as catalyst, the temperature is kept at 133 ℃ for 4 hours, and the yield of tebuconazole is 79%; as reported in Zhang et al, research on the Synthesis of Tebuconazole as a fungicide (pesticide science and management, 2004, 25 (5), 23-25), CO was slowly introduced under the conditions of a certain solvent, a certain catalyst and potassium carbonate 2 Gas is subjected to reflux reaction, and the yield of tebuconazole is about 83 percent; in the synthesis methods, inorganic base and solvent are added, so that the yield and the content of tebuconazole are low, and further optimization and improvement are needed; as reported in chinese patent CN109705048, in a solvent of diethylene glycol monomethyl ether, pentylene oxide and 1,2, 4-triazole are heated and reacted in an inorganic base potassium hydroxide with heat preservation, and the tebuconazole is obtained by post-treatment with a yield of about 91% -92%; the yield is greatly improved, a solvent and inorganic base are added in the process, but the raw material cost and the process have a large improvement space in environmental protection; therefore, it is urgently required to seekAn economic, environment-friendly and efficient tebuconazole synthesis method with green process.
Disclosure of Invention
The invention aims to provide a green and efficient synthesis method of tebuconazole, which solves the problems in the background art.
In order to achieve the purpose, the invention provides the following technical scheme: a green high-efficiency synthesis method of tebuconazole comprises the following steps: step one, preparing raw materials; step two, reacting raw materials; step three, standing and phase splitting; step four, cooling; step five, obtaining a tebuconazole finished product;
wherein in the first step, a proper amount of 1,2, 4-triazole, ionic liquid and pentoxy are prepared;
in the second step, 1,2, 4-triazole and ionic liquid are added into a reaction bottle, the mixture is heated to a certain temperature, pentylene oxide is dripped, and the reaction is carried out under heat preservation after the addition;
in the third step, after the reaction in the second step is finished, standing and phase splitting are carried out to obtain an ionic liquid phase and a tebuconazole phase;
in the fourth step, the ionic liquid phase obtained after the phase separation in the third step is recycled and reused, and the tebuconazole phase is cooled to room temperature to obtain a solid;
in the fifth step, the solid obtained by cooling in the fourth step is pulped by methanol water with a certain proportion, and the finished product of the tebuconazole is obtained by filtering and drying the solid, wherein the methanol water can be used for the next batch.
Preferably, in the first step, the ionic liquid is selected from any one or more of the following combinations: imidazole ionic liquid, pyridine ionic liquid, pyrrolidine ionic liquid, morpholine ionic liquid and piperidine ionic liquid.
Preferably, in the second step, the weight of the ionic liquid is 0.1-2 times of the weight of the pentalane oxygen.
Preferably, in the second step, the heat preservation temperature is 80-110 ℃, and the heat preservation time is 1-5h.
Preferably, in the fifth step, the proportion of methanol to water is 30-60%.
Preferably, in the fifth step, the yield of the finished tebuconazole is 93.0-93.3%, and the purity is 98.0-98.3%.
Compared with the prior art, the invention has the beneficial effects that: compared with the existing tebuconazole preparation method, the reaction conditions are simpler, the tebuconazole with high yield and high purity can be directly synthesized without other solvents and alkali, and additional alkali catalysts and phase transfer catalysts are not needed, so that the method is greener in process, reduces the environmental protection pressure, and is suitable for industrial scale-up production.
Drawings
FIG. 1 is a scheme for the synthesis of tebuconazole of the present invention;
FIG. 2 is a flow chart of the method of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in 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.
Referring to fig. 1-2, a technical solution provided by the present invention is:
example 1
A green high-efficiency synthesis method of tebuconazole comprises the following steps: step one, preparing raw materials; step two, raw material reaction; step three, standing and phase splitting; step four, cooling; step five, obtaining a finished tebuconazole product;
in the first step, preparing a proper amount of 1,2, 4-triazole, imidazole ionic liquid 1-butyl-3-methylimidazolium bromide and pentocyclic oxygen;
in the second step, 16.7g of 1,2, 4-triazole and 50.0g of imidazole ionic liquid 1-butyl-3-methylimidazolium bromide are added into a three-neck flask, the temperature is controlled to be 100-105 ℃, 50.0g (0.2 mol) of pentone is added dropwise, and the mixture is stirred for 2-3 hours after the addition is finished;
in the third step, after the reaction in the second step is finished, standing and phase splitting are carried out to obtain an ionic liquid phase and a tebuconazole phase;
in the fourth step, the ionic liquid phase obtained after phase splitting in the third step is recycled and reused, and the tebuconazole phase is cooled to room temperature to obtain a solid;
in the fifth step, the solid obtained by cooling in the fourth step is pulped by 50.0g of 50% methanol water, the finished product of tebuconazole is obtained after the solid is filtered and dried, and the methanol water can be used for the next batch; LCMS:308 (M + H); 1 H NMR(CDCl 3 )8.22(s，1H)，8.03(s，1H)，7.21(d，J＝8.0Hz，2H)，6.95(d，J＝8.0Hz，2H)，4.37(s，2H)，3.07(s，1H)，2.42-2.48(m，1H)，1.67-1.86(m，3H)，1.03(s，9H)。
example 2
A green high-efficiency synthesis method of tebuconazole comprises the following steps: step one, preparing raw materials; step two, raw material reaction; step three, standing and phase splitting; step four, cooling; step five, obtaining a finished tebuconazole product;
in the first step, preparing a proper amount of 1,2, 4-triazole, imidazole ionic liquid 1-butyl-3-methylimidazolium bromide and pentone oxygen; wherein the imidazole ionic liquid 1-butyl-3-methylimidazolium bromide is recovered in example 1;
in the second step, 16.7g of 1,2, 4-triazole and 50.0g of imidazole ionic liquid 1-butyl-3-methylimidazolium bromide are added into a three-neck flask, the temperature is controlled to be 100-105 ℃, 50.0g (0.2 mol) of pentone is added dropwise, and the mixture is stirred for 2-3 hours after the addition is finished;
in the third step, after the reaction in the second step is finished, standing and phase splitting are carried out to obtain an ionic liquid phase and a tebuconazole phase;
in the fourth step, the ionic liquid phase obtained after the phase separation in the third step is recycled and reused, and the tebuconazole phase is cooled to room temperature to obtain a solid;
in the fifth step, the solid obtained by cooling in the fourth step is pulped by 50.0g of 50% methanol water, the finished product of the tebuconazole is obtained by filtering and drying the solid, and the methanol water can be used for the next batch.
Example 3
A green high-efficiency synthesis method of tebuconazole comprises the following steps: step one, preparing raw materials; step two, raw material reaction; step three, standing and phase splitting; step four, cooling; step five, obtaining a finished tebuconazole product;
in the first step, preparing a proper amount of 1,2, 4-triazole, imidazole ionic liquid 1-benzyl-3-methylimidazole chloride and pentone oxygen;
in the second step, 16.7g of 1,2, 4-triazole and 50.0g of imidazole ionic liquid 1-benzyl-3-methylimidazole chloride are added into a three-neck flask, the temperature is controlled to be 100-105 ℃, 50.0g (0.2 mol) of pentone oxygen is added dropwise, and the mixture is stirred for 2-3 hours after heat preservation;
in the third step, after the reaction in the second step is finished, standing and phase splitting are carried out to obtain an ionic liquid phase and a tebuconazole phase;
in the fourth step, the ionic liquid phase obtained after the phase separation in the third step is recycled and reused, and the tebuconazole phase is cooled to room temperature to obtain a solid;
in the fifth step, the solid obtained by cooling in the fourth step is pulped by 50.0g of 50% methanol water, the finished product of tebuconazole is obtained after the solid is filtered and dried, and the methanol water can be used for the next batch.
Example 4
A green high-efficiency synthesis method of tebuconazole comprises the following steps: step one, preparing raw materials; step two, raw material reaction; step three, standing and phase splitting; step four, cooling; step five, obtaining a tebuconazole finished product;
in the first step, preparing a proper amount of 1,2, 4-triazole, imidazole ionic liquid 1-benzyl-3-methylimidazole chloride and pentone oxygen; wherein, the imidazole ionic liquid 1-benzyl-3-methylimidazole chloride is recovered from the embodiment 3;
in the second step, 16.7g of 1,2, 4-triazole and 50.0g of imidazole ionic liquid 1-benzyl-3-methylimidazole chloride are added into a three-neck flask, the temperature is controlled to be 100-105 ℃, 50.0g (0.2 mol) of pentone oxygen is added dropwise, and the mixture is stirred for 2-3 hours after heat preservation;
in the third step, after the reaction in the second step is finished, standing and phase splitting are carried out to obtain an ionic liquid phase and a tebuconazole phase;
in the fourth step, the ionic liquid phase obtained after the phase separation in the third step is recycled and reused, and the tebuconazole phase is cooled to room temperature to obtain a solid;
in the fifth step, the solid obtained by cooling in the fourth step is pulped by 50.0g of 50% methanol water, the finished product of the tebuconazole is obtained by filtering and drying the solid, and the methanol water can be used for the next batch.
The properties and ratios of the above examples are as follows:
based on the above, the method has the advantages that the tebuconazole is directly synthesized by taking the tebuconazole intermediates of the pentylene oxide and the 1,2, 4-triazole as raw materials under the condition of no need of other solvents and alkali, the yield and the purity of the obtained tebuconazole are high, and the method has the advantages of environmental protection, simple and efficient process and great industrial development value.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Claims (6)
1. A green high-efficiency synthesis method of tebuconazole comprises the following steps: step one, preparing raw materials; step two, reacting raw materials; step three, standing and phase splitting; step four, cooling; step five, obtaining a tebuconazole finished product; the method is characterized in that:
wherein in the first step, a proper amount of 1,2, 4-triazole, ionic liquid and pentoxy are prepared;
in the second step, 1,2, 4-triazole and ionic liquid are added into a reaction bottle, the mixture is heated to a certain temperature, pentylene oxide is dripped, and the reaction is carried out under heat preservation after the addition;
in the third step, after the reaction in the second step is finished, standing and phase splitting are carried out to obtain an ionic liquid phase and a tebuconazole phase;
in the fourth step, the ionic liquid phase obtained after the phase separation in the third step is recycled and reused, and the tebuconazole phase is cooled to room temperature to obtain a solid;
in the fifth step, the solid obtained by cooling in the fourth step is pulped by methanol water with a certain proportion, and the finished product of the tebuconazole is obtained by filtering and drying the solid, wherein the methanol water can be used for the next batch.
2. The green high-efficiency synthesis method of tebuconazole according to claim 1, characterized by comprising the following steps of: in the first step, the ionic liquid is selected from any one or more of the following combinations: imidazole ionic liquid, pyridine ionic liquid, pyrrolidine ionic liquid, morpholine ionic liquid and piperidine ionic liquid.
3. The green high-efficiency synthesis method of tebuconazole according to claim 1, characterized by comprising the following steps of: in the second step, the weight of the ionic liquid is 0.1-2 times of that of the pentone oxygen.
4. The green high-efficiency synthesis method of tebuconazole according to claim 1, characterized by comprising the following steps of: in the second step, the heat preservation temperature is 80-110 ℃, and the heat preservation time is 1-5h.
5. The green high-efficiency synthesis method of tebuconazole according to claim 1, characterized by comprising the following steps of: in the fifth step, the proportion of the methanol and the water is 30-60 percent.
6. The green high-efficiency synthesis method of tebuconazole according to claim 1, characterized by comprising the following steps of: in the fifth step, the yield of the finished tebuconazole is 93.0-93.3%, and the purity is 98.0-98.3%.
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| WO2024078646A1 (en) * | 2023-07-18 | 2024-04-18 | 常州大学 | Method for preparing (r)-tebuconazole by means of enzyme chemical process |
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| CN102258011A (en) * | 2011-06-03 | 2011-11-30 | 中国农业大学 | Bactericidal pesticide preparation by taking ionic liquid as cosolvent and preparation method thereof |
| CN103435564A (en) * | 2013-08-22 | 2013-12-11 | 上虞颖泰精细化工有限公司 | Preparation method of tebuconazole |
| CN106588791A (en) * | 2016-11-01 | 2017-04-26 | 盐城辉煌化工有限公司 | Novel technology for synthesizing bactericide tebuconazole without solvent |
| CN106946787A (en) * | 2017-03-22 | 2017-07-14 | 南京工业大学 | A kind of synthetic method of imidazoles acidic ion liquid |
| CN108299319A (en) * | 2018-02-08 | 2018-07-20 | 盐城辉煌化工有限公司 | The easy technique new method of synthesis in water Tebuconazole |
| CN109336848A (en) * | 2018-10-26 | 2019-02-15 | 江苏七洲绿色化工股份有限公司 | A kind of preparation method of tebuconazole intermediate and Tebuconazole |
| CN109705048A (en) * | 2019-01-31 | 2019-05-03 | 上海生农生化制品股份有限公司 | A kind of clean method for preparing of Tebuconazole |
| CN110563660A (en) * | 2019-09-11 | 2019-12-13 | 江苏七洲绿色化工股份有限公司 | Method for reducing 1,3, 4-triazole substituent in alkylation reaction process of 1,2, 4-triazole |
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| WO2024078646A1 (en) * | 2023-07-18 | 2024-04-18 | 常州大学 | Method for preparing (r)-tebuconazole by means of enzyme chemical process |
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