CN112979550A - Method for preparing 1-methyl-5-hydroxypyrazole by using microchannel reactor - Google Patents
Method for preparing 1-methyl-5-hydroxypyrazole by using microchannel reactor Download PDFInfo
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- CN112979550A CN112979550A CN202110325290.7A CN202110325290A CN112979550A CN 112979550 A CN112979550 A CN 112979550A CN 202110325290 A CN202110325290 A CN 202110325290A CN 112979550 A CN112979550 A CN 112979550A
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- JMARSTSWTFXHMC-UHFFFAOYSA-N 2-methyl-1h-pyrazol-3-one Chemical compound CN1NC=CC1=O JMARSTSWTFXHMC-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- 239000007864 aqueous solution Substances 0.000 claims abstract description 16
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 10
- AUTCCPQKLPMHDN-ONEGZZNKSA-N methyl (e)-3-methoxyprop-2-enoate Chemical compound CO\C=C\C(=O)OC AUTCCPQKLPMHDN-ONEGZZNKSA-N 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 20
- 239000012295 chemical reaction liquid Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000002920 hazardous waste Substances 0.000 abstract description 4
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 238000010924 continuous production Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001514 detection method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001802 infusion Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000011895 specific detection Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- DERAACKMMNJAFU-UHFFFAOYSA-N 2-ethoxy-1,3-dioxane-4,6-dione Chemical compound CCOC1OC(=O)CC(=O)O1 DERAACKMMNJAFU-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- GJUJIVCZCCXXOX-UHFFFAOYSA-N CN1N=C(C(O)=O)C=C1O Chemical compound CN1N=C(C(O)=O)C=C1O GJUJIVCZCCXXOX-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
Abstract
The invention relates to a method for preparing 1-methyl-5-hydroxypyrazole by using a microchannel reactor, belonging to the technical field of fine chemical engineering. The invention adopts methyl 3-methoxyacrylate and methyl hydrazine aqueous solution as reaction raw materials, and utilizes a microchannel reactor as reaction equipment to prepare 1-methyl-5-hydroxypyrazole. Compared with the kettle type reaction, the method has the advantages that the yield and the reaction purity are obviously improved. Moreover, the invention does not use solvent in the preparation process, so that the hazardous waste generated is less. The invention uses the microchannel reactor to prepare the 1-methyl-5-hydroxypyrazole, can realize continuous production, simplifies the operation process and improves the production efficiency and safety.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a method for preparing 1-methyl-5-hydroxypyrazole by using a microchannel reactor.
Background
1-methyl-5-hydroxypyrazole (MHP) is an important pesticide intermediate, and can be used for synthesizing topramezone. Sucrow W et al reported that hydrolytic decarboxylation of 1-methyl-5-hydroxypyrazole-3-carboxylate produced 1-methyl-5-hydroxypyrazole as early as 1967, but only in 6% yield. In 1971, 2-methyl-1-acyl-3-pyrazolone hydrolysis methods such as Dorn H and the like are adopted to prepare 1-methyl-5-hydroxypyrazole, but the hydrolysis methods are complex in reaction, multiple in steps and lack practical value. The existing synthesis method of 1-methyl-5-hydroxypyrazole mainly comprises a cyclization decarboxylation method of ethoxymethylene malonate and methyl hydrazine, a cyclization method of 3-alkoxy acrylate and a condensation cyclization method of acrylate or amide, formaldehyde and hydrazine hydrate, wherein the most commonly used method in industry is a cyclization method for batch synthesis of methyl 3-methoxyacrylate and methyl hydrazine in a kettle manner.
The kettle type batch synthesis of 1-methyl-5-hydroxypyrazole is carried out by dropping 3-methoxy methyl acrylate and methyl hydrazine into methanol at certain temperature, reacting for certain time, evaporating to remove methanol and water, adding solvent, cooling to precipitate, and filtering to obtain 1-methyl-5-hydroxypyrazole. The kettle type batch synthesis method has simple operation, but the yield is not high and is only proved to be 30 percent. And the kettle type intermittent synthesis method generates a large amount of viscous mother liquor containing a small amount of products, and only can be used for treating hazardous wastes, so that the cost of the 1-methyl-5-hydroxypyrazole is higher.
Disclosure of Invention
Aiming at the problems of low yield, more dangerous waste generation and the like in the process of synthesizing 1-methyl-5-hydroxypyrazole by using a kettle type batch synthesis method in the prior art, the invention provides a method for preparing 1-methyl-5-hydroxypyrazole by using a microchannel reactor, and aims to solve the problems. The invention improves the existing preparation yield and reduces the generation of hazardous wastes by using the microchannel reactor as the reaction equipment. Moreover, the method can realize continuous and automatic production and improve the production efficiency.
The technical scheme of the invention is as follows:
a method for preparing 1-methyl-5-hydroxypyrazole by using a microchannel reactor has the following reaction formula:
the preparation method comprises the following steps:
(1) marking 3-methoxy methyl acrylate as liquid A, marking methyl hydrazine aqueous solution as liquid B, starting a delivery pump, delivering the liquid A and the liquid B to a first reaction module of a microchannel reactor, and reacting the two materials in the first reaction module;
(2) after the reaction liquid passes through a plurality of reaction modules, obtaining an aqueous solution containing 1-methyl-5-hydroxypyrazole from a discharge hole;
(3) and (3) evaporating the aqueous solution of the 1-methyl-5-hydroxypyrazole prepared in the step (2) to dryness, adding a solvent, stirring, cooling, crystallizing, filtering, and drying to obtain the 1-methyl-5-hydroxypyrazole.
Preferably, the microchannel reactor is an enhanced mass transfer microchannel reactor.
Preferably, the temperature of the reaction module is set to be 0-50 ℃.
Preferably, in the step (1), the feeding molar ratio of the methyl 3-methoxyacrylate to the methylhydrazine is 1: 1.0-1.5.
Preferably, in the step (1), the feeding molar ratio of the methyl 3-methoxyacrylate to the methylhydrazine is 1: 1.05-1.1.
Preferably, in the step (2), the reaction solution passes through 10 reaction modules, and the residence time in each reaction module is 1-25 s.
Preferably, in the step (3), the aqueous solution of the 1-methyl-5-hydroxypyrazole is evaporated to dryness until the water content is less than or equal to 0.1%.
Preferably, in the step (3), the solvent is an anhydrous solvent, such as ethanol, ethyl acetate, or a mixture thereof.
Preferably, in the step (3), the crystallization temperature is-5 to 10 ℃, and the crystallization time is 4 to 24 hours.
The invention has the beneficial effects that:
the invention adopts a microchannel reactor to prepare 1-methyl-5-hydroxypyrazole, and replaces the existing kettle type reaction. Compared with the kettle type reaction, the method has the advantages that the yield and the reaction purity are obviously improved. Moreover, the invention does not use solvent in the preparation process, so that the hazardous waste generated is less. The invention uses the microchannel reactor to prepare the 1-methyl-5-hydroxypyrazole, can realize continuous production, simplifies the operation process and improves the production efficiency and safety.
Drawings
In order to more clearly illustrate the embodiments or technical solutions in the prior art of the present invention, the drawings used in the description of the embodiments or prior art will be briefly described below, and it is obvious for those skilled in the art that other drawings can be obtained based on these drawings without creative efforts.
FIG. 1 is a gas phase detection spectrum of a reaction liquid of example 1 of the present invention;
FIG. 2 is a gas-phase detection spectrum of a reaction solution of example 2 of the present invention;
FIG. 3 is a gas phase detection spectrum of a reaction liquid of a comparative example of the present invention.
Detailed Description
In order to make those skilled in the art better understand the technical solution of the present invention, the technical solution in the embodiment of the present invention will be clearly and completely described below with reference to the drawings in the embodiment of the present invention, and it is obvious that the described embodiment is only a part of the embodiment of the present invention, and not all 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
Microchannel reactor model: RMCS1010, 10 reaction modules, a single-chip reaction unit with liquid holdup of 0.75mL and a pipeline and joint with liquid holdup of 2.9 mL; the infusion pump model: PF100 semi-preparative medium pressure infusion pump.
The preparation method comprises the following steps:
(1) 592g of methyl 3-methoxyacrylate with the content of 98 percent is placed in a liquid storage bottle A and is marked as solution A; 600g of 40% methylhydrazine aqueous solution is placed in a liquid storage bottle B and labeled as solution B. The flow rate of the liquid A is set to be 15.6g/min, the flow rate of the liquid B is set to be 15.8g/min, the temperature of the reaction modules is 10 ℃, and the residence time of each reaction module is 2 s. And starting the delivery pump, and delivering the solution A and the solution B to a first reaction module of the microchannel reactor for reaction.
(2) After the reaction liquid passes through 10 reaction modules, the aqueous solution containing 1-methyl-5-hydroxypyrazole is obtained from a discharge hole. The reaction solution was temporarily stored in a receiving vessel. Sampling gas phase detection shows that the purity of the 1-methyl-5-hydroxypyrazole in the reaction liquid is 91.3279%, and the specific detection value is shown in Table 1.
(3) And (3) evaporating the aqueous solution of the 1-methyl-5-hydroxypyrazole prepared in the step (2) to dryness under negative pressure. Then 1000mL of absolute ethyl alcohol is added, the mixture is stirred and cooled to 0 ℃ for crystallization for 6h, and 1-methyl-5-hydroxypyrazole 341g is obtained after filtration and drying. The purity by gas phase detection was 98.3%, and the yield was 69.6%.
TABLE 1 gas phase test results of the reaction solution of example 1
| Peak number | Retention time/min | Peak height | Peak area | Content/% |
| 1 | 1.830 | 7594.660 | 8231.336 | 4.9827 |
| 2 | 1.888 | 3918.805 | 5617.642 | 3.4005 |
| 3 | 1.955 | 93090.258 | 150871.953 | 91.3279 |
| 4 | 2.842 | 309.000 | 477.200 | 0.2889 |
Example 2
Microchannel reactor model: RMCS402, 10 reaction modules, a single-chip reaction unit liquid holdup of 9.2mL, and a pipeline and joint liquid holdup of 7.8 mL; the infusion pump model: PF100 semi-preparative medium pressure infusion pump.
The preparation method comprises the following steps:
(1) putting 5kg of methyl 3-methoxyacrylate with the content of 98% in a liquid storage bottle A, and marking as solution A; 5.3kg of 40% methylhydrazine aqueous solution was placed in a liquid storage bottle B and labeled as solution B. The flow rate of the liquid A is set to be 58.2g/min, the flow rate of the liquid B is set to be 61.8g/min, the temperature of the reaction modules is set to be 30 ℃, and the residence time of each reaction module is set to be 5 s. And starting the delivery pump, and delivering the solution A and the solution B to a first reaction module of the microchannel reactor for reaction.
(2) After the reaction liquid passes through 10 reaction modules, the aqueous solution containing 1-methyl-5-hydroxypyrazole is obtained from a discharge hole. The reaction solution was temporarily stored in a receiving vessel. Sampling gas phase detection shows that the purity of the 1-methyl-5-hydroxypyrazole in the reaction liquid is 94.4231%, and the specific detection value is shown in Table 2.
(3) And (3) evaporating the aqueous solution of the 1-methyl-5-hydroxypyrazole prepared in the step (2) to dryness under negative pressure. Then 10L of absolute ethyl alcohol is added, the mixture is stirred and cooled to 5 ℃ for crystallization for 10h, and the mixture is filtered and dried to obtain 2.92kg of 1-methyl-5-hydroxypyrazole, the purity is 98.7 percent by gas phase detection, and the yield is 70.5 percent.
TABLE 2 gas phase test results of the reaction solution of example 2
| Peak number | Retention time/min | Peak height | Peak area | Content/% |
| 1 | 1.712 | 1933.001 | 1976.100 | 1.1270 |
| 2 | 1.792 | 212.857 | 161.550 | 0.0921 |
| 3 | 1.867 | 4072.412 | 7201.979 | 4.1073 |
| 4 | 1.937 | 84337.477 | 165567.250 | 94.4231 |
| 5 | 3.677 | 76.748 | 329.200 | 0.1877 |
| 6 | 4.285 | 58.368 | 110.100 | 0.0628 |
Comparative example
The kettle type reaction is adopted to prepare the 1-methyl-5-hydroxypyrazole, and the specific method is as follows:
(1) adding 1500kg of anhydrous methanol into a reaction kettle, adding 1000kg of 98% methyl 3-methoxyacrylate under stirring, cooling to 5-10 ℃ after stirring and dissolving, and slowly adding 1067kg of 40% methylhydrazine aqueous solution; after the addition is finished, the temperature is raised to 80-85 ℃ for reaction, and GC monitors that the reaction of the 3-methoxy methyl acrylate is complete, wherein the total time is 16 hours. The purity of 1-methyl-5-hydroxypyrazole in the reaction solution at the end of the reaction was 83.0714%, and the specific detection values are shown in Table 3.
(2) Evaporating the reaction solution prepared in the step (1) to dryness under negative pressure, adding 2000L of absolute ethanol, stirring, cooling to 5 ℃ for crystallization for 11h, filtering, and drying to obtain 267kg of 1-methyl-5-hydroxypyrazole, wherein the purity is 98.5% by gas phase detection, and the yield is 32.2%.
TABLE 3 gas phase test results of comparative example reaction solution
| Peak number | Retention time/min | Peak height | Peak area | Content/% |
| 1 | 1.807 | 16988.158 | 19544.121 | 11.9211 |
| 2 | 1.865 | 4743.316 | 6219.829 | 3.7938 |
| 3 | 1.940 | 76933.977 | 136191.750 | 83.0714 |
| 4 | 2.832 | 172.444 | 105.000 | 0.0640 |
| 5 | 3.890 | 100.667 | 192.500 | 0.1174 |
| 6 | 4.623 | 81.438 | 291.600 | 0.1779 |
| 7 | 6.215 | 58.537 | 1400.700 | 0.8544 |
As can be seen from the comparison of the examples 1 and 2 with the comparative example, the invention adopts the microchannel reactor, the reaction time and the purity of the 1-methyl-5-hydroxypyrazole in the reaction liquid prepared after the reaction are both better than the kettle type reaction, and the yield of the finally obtained product is much higher than that of the comparative example. Therefore, the conversion rate of the reaction and the production efficiency can be effectively improved by adopting the microchannel reactor.
Although the present invention has been described in detail by referring to the drawings in connection with the preferred embodiments, the present invention is not limited thereto. Various equivalent modifications or substitutions can be made on the embodiments of the present invention by those skilled in the art without departing from the spirit and scope of the present invention, and these modifications or substitutions are within the scope of the present invention/any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (9)
1. A method for preparing 1-methyl-5-hydroxypyrazole by using a microchannel reactor is characterized by comprising the following reaction formula:
the preparation method comprises the following steps:
(1) marking 3-methoxy methyl acrylate as liquid A, marking methyl hydrazine aqueous solution as liquid B, starting a delivery pump, delivering the liquid A and the liquid B to a first reaction module of a microchannel reactor, and reacting the two materials in the first reaction module;
(2) after the reaction liquid passes through a plurality of reaction modules, obtaining an aqueous solution containing 1-methyl-5-hydroxypyrazole from a discharge hole;
(3) and (3) evaporating the aqueous solution of the 1-methyl-5-hydroxypyrazole prepared in the step (2) to dryness, adding a solvent, stirring, cooling, crystallizing, filtering, and drying to obtain the 1-methyl-5-hydroxypyrazole.
2. The process of claim 1 wherein the microchannel reactor is an enhanced mass transfer microchannel reactor.
3. The method of claim 1, wherein the temperature of the reaction module is set to 0 to 50 ℃.
4. The method according to claim 1, wherein in the step (1), the feeding molar ratio of the methyl 3-methoxyacrylate to the methylhydrazine is 1: 1.0-1.5.
5. The method according to any one of claims 1 or 4, wherein in the step (1), the feeding molar ratio of the methyl 3-methoxyacrylate to the methylhydrazine is 1: 1.05-1.1.
6. The method according to claim 1, wherein in the step (2), the reaction solution passes through 10 reaction modules, and the residence time in each reaction module is 1-25 s.
7. The method according to claim 1, wherein in the step (3), the aqueous solution of 1-methyl-5-hydroxypyrazole is evaporated to dryness until the water content is 0.1% or less.
8. The method according to claim 1, wherein in the step (3), the solvent is selected from anhydrous solvents, and the anhydrous solvent is at least one selected from ethanol and ethyl acetate.
9. The method according to claim 1, wherein in the step (3), the crystallization temperature is-5 to 10 ℃ and the crystallization time is 4 to 24 hours.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040082804A1 (en) * | 2002-10-22 | 2004-04-29 | Brophy John H. | Multiphasic microchannel reactions |
| CN109320457A (en) * | 2018-10-12 | 2019-02-12 | 凯莱英医药化学（阜新）技术有限公司 | The preparation method and device of hydroxypyrazoles |
| CN112062720A (en) * | 2020-09-10 | 2020-12-11 | 江苏七洲绿色化工股份有限公司 | Continuous preparation method of 1-methyl-3-hydroxypyrazole-4-carboxylic acid ethyl ester |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040082804A1 (en) * | 2002-10-22 | 2004-04-29 | Brophy John H. | Multiphasic microchannel reactions |
| CN109320457A (en) * | 2018-10-12 | 2019-02-12 | 凯莱英医药化学（阜新）技术有限公司 | The preparation method and device of hydroxypyrazoles |
| CN112062720A (en) * | 2020-09-10 | 2020-12-11 | 江苏七洲绿色化工股份有限公司 | Continuous preparation method of 1-methyl-3-hydroxypyrazole-4-carboxylic acid ethyl ester |
Non-Patent Citations (1)
| Title |
|---|
| 杨光富: "《有机合成》", 31 August 2016, 华东理工大学出版社 * |
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Application publication date: 20210618 |