CN114573487A - Method for preparing butylpropylthiourea - Google Patents
Method for preparing butylpropylthiourea Download PDFInfo
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- CN114573487A CN114573487A CN202210243185.3A CN202210243185A CN114573487A CN 114573487 A CN114573487 A CN 114573487A CN 202210243185 A CN202210243185 A CN 202210243185A CN 114573487 A CN114573487 A CN 114573487A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/20—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention discloses a method for preparing butylthiosemicarbazide, which comprises the following steps: (1) dissolving tert-butyl alcohol and ammonium thiocyanate in water, and mixing to obtain a homogeneous solution A; (2) pumping the homogeneous phase solution A and a hydrochloric acid solution into a microreactor and an extraction device I simultaneously, reacting and extracting, and collecting an organic phase liquid, namely a mixture of tert-butyl thiocyanate and tert-butyl isothiocyanate, which is called mixed ester for short; (3) pumping the obtained mixed ester into a microreactor II which is fixedly loaded with a catalyst for reaction, and collecting effluent liquid, namely tert-butyl isothiocyanate, namely isopropyl ester for short; (4) dissolving the obtained isopropyl ester in a first organic solvent to obtain a homogeneous phase solution B; dissolving isopropylamine in a second organic solvent to obtain a homogeneous solution C; (5) and respectively pumping the homogeneous solution B and the homogeneous solution C into the microreactor III at the same time, reacting, collecting effluent liquid, and performing aftertreatment to obtain the thiobutyronitrile. The method improves the heat and mass transfer efficiency, and is safe, efficient and energy-saving.
Description
Technical Field
The invention belongs to the technical field of butylpropylthiourea synthesis, and particularly relates to a method for preparing butylpropylthiourea.
Background
The butyl propyl thiourea is called 1-isopropyl-3-tert-butyl thiourea, and is a key intermediate for synthesizing pesticide buprofezin. Buprofezin, also known as chlorpheniramine, was developed by japan pesticide company in the 80 th 20 th century, and is an insecticide capable of effectively controlling pests such as rice planthoppers, leafhoppers, tea leafhoppers, citrus arrowhead scales and the like. The application and the demand of the insecticide pediculicide are highly related to the development of agricultural economy, in particular to the development of crop planting industries such as rice and the like. At present, the delphacidae product in China is mainly exported to regions such as Thailand, Singapore, Malaysia, Vietnam, Myanmar and the like, most of the regions are regions with developed agricultural economy and large rice planting area, and the insect disasters such as the Laodelphax striatellus and the rice planthopper in China occur more and the demand on pesticides is more.
The synthesis of the thiobutyronitrile takes ammonium thiocyanate as a raw material to react with tert-butyl alcohol in the presence of hydrochloric acid to obtain a mixture (called mixed ester for short) of tert-butyl thiocyanate and tert-butyl isocyanate, tert-butyl isothiocyanate (called isopropyl ester for short) is obtained through transposition, and then the tert-butyl thiocyanate and isopropyl amine react to obtain the thiobutyronitrile. The traditional production preparation method mostly adopts an intermittent production process, (1) the operation steps are complex, the yield loss is high, (2) the heat and mass transfer efficiency of mixing and reaction is low, the production time is long, and the control is difficult; (3) the production personnel can not be isolated from the materials and equipment, and the potential safety hazard in the production process is increased.
Disclosure of Invention
The purpose of the invention is as follows: in order to solve the problems in the prior art, the invention provides a method for preparing butylpropylthiourea, which improves the heat and mass transfer efficiency of the prior art and provides a safe, efficient and energy-saving solution for the preparation of butylpropylthiourea.
The technical scheme is as follows: in order to achieve the above-mentioned problem, the technical solution adopted by the present invention is as follows:
a method for preparing butylthiosemicarbazide by a micro-flow field reaction technology comprises the following steps:
(1) dissolving tert-butyl alcohol and ammonium thiocyanate in water, and mixing to obtain a homogeneous solution A;
(2) pumping the homogeneous phase solution A and a hydrochloric acid solution into a microreactor and an extraction device I simultaneously, reacting and extracting, and collecting an organic phase liquid, namely a mixture of tert-butyl thiocyanate and tert-butyl isothiocyanate, which is called mixed ester for short;
(3) pumping the obtained mixed ester into a microreactor II which is fixedly loaded with a catalyst for reaction, and collecting effluent liquid, namely tert-butyl isothiocyanate, namely isopropyl ester for short;
(4) dissolving the obtained isopropyl ester in a first organic solvent to obtain a homogeneous phase solution B; dissolving isopropylamine in a second organic solvent to obtain a homogeneous solution C;
(5) and respectively pumping the homogeneous solution B and the homogeneous solution C into the microreactor III at the same time, reacting, collecting effluent liquid, and performing aftertreatment to obtain the thiobutyronitrile.
Preferably, in the step (1), the molar ratio of ammonium thiocyanate to tert-butyl alcohol in the homogeneous solution a is controlled to be 1: 0.8-1.5, and the mass ratio of ammonium thiocyanate to water is 1: 1.0-3.0.
Preferably, in the step (2), the reaction molar ratio of ammonium thiocyanate to hydrogen chloride in hydrochloric acid is controlled to be 1: 0.8-1.5, and the reaction molar ratio is controlled by the flow rate ratio of the homogeneous solution A and the hydrochloric acid solution pumped into the microreactor & extraction device I.
Preferably, in the step (2), the microreactor & extraction device I is an integrated continuous microfluidic platform formed by connecting a microfluidic field reactor and a microfluidic field extraction device in series; the reaction temperature in the micro-flow field reactor is 60-110 ℃, and the reaction retention time is 1-15 min; the extraction retention time in the micro-flow field extraction device is 1-5 min.
Preferably, in the step (3), a catalyst is immobilized in the inner wall or the internal component of the microreactor II, the catalyst is selected from zinc chloride, the reaction temperature is 40-90 ℃, and the reaction residence time is 1-15 min.
Preferably, in the step (4), the first organic solvent and the second organic solvent are both organic solvents capable of dissolving the thiobutamide, the isopropyl ester and the isopropylamine, and the solvents do not react with the three substances.
Preferably, in the step (5), the reaction molar ratio of the isopropyl ester to the isopropylamine is controlled to be 1: 1.0-1.5, and the reaction molar ratio is controlled by the flow rate ratio of pumping the homogeneous solution B and the homogeneous solution C into the microreactor III.
Preferably, in the step (5), the reaction temperature is 0-100 ℃, and the reaction residence time is 1-15 min.
Preferably, in step (5), the post-treatment process includes, but is not limited to, evaporation drying, recrystallization and/or pulping purification.
Preferably, in the step (2), the water phase obtained after extraction is recovered by means of acid-base neutralization, distillation and the like and is used for the dissolving operation in the step (1); in the step (5), the organic solution containing isopropylamine obtained by evaporation and drying in the post-treatment process can be used for dissolving isopropylamine in the step (4), ethanol is adopted for recrystallization in the post-treatment process of the reaction liquid, and the ethanol used for recrystallization can be recycled after evaporation and drying of the product, so that recycling is realized.
Has the advantages that: compared with the prior art, the invention is based on the micro chemical technology of flow controllable and high-efficiency mixing transfer under the micro scale, and has the characteristic of high-efficiency heat and mass transfer. The reaction rate and the heat and mass transfer efficiency can be improved by improving the process flow through the micro chemical technology, and the specific expression is that the mass transfer effect in the first esterification reaction and the post-treatment separation process can be obviously improved, and the reaction temperature and the reaction pressure can be efficiently and stably controlled in the third strong exothermic reaction. The continuous production of the thiobutazine is realized by the micro-flow field reaction technology, the process can improve the automation control degree of the production flow, simplify the production operation flow and improve the production safety.
Drawings
FIG. 1 is a schematic diagram of the process flow of thiobutyrothiourea of the present invention.
FIG. 2 is a schematic view of a microfluidic field reaction and extraction apparatus according to the present invention.
FIG. 3 shows butylthiosemicarbazide obtained in example 1 of the present invention1HNMR map.
FIG. 4 shows tert-butyl isothiocyanate obtained in example 1 of the present invention1HNMR map.
Detailed Description
The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
The method has the following reaction formula:
example 1
16.3g (0.22mol) of tert-butanol and 15.2g (0.2mol) of ammonium thiocyanate were dissolved in 19g of water to give a homogeneous solution, ready for use. Pumping the prepared solution and 20% hydrochloric acid solution into a microreactor through a high-pressure injection pump, wherein the flow rate ratio of tert-butyl alcohol-ammonium thiocyanate solution to hydrochloric acid is 3:2, reacting the reaction solution at 85 ℃, adjusting the outlet pressure of the reactor to enable the reaction solution to stably flow in a reaction system, the reaction retention time is 10 minutes, allowing the effluent liquid to enter a microflow field extraction device, and separating a water phase and an organic phase through a membrane separator after the effluent liquid stays for 3 minutes, wherein the organic phase is mixed ester; pumping the mixed ester into a microreactor fixedly loaded with zinc chloride at the speed of 0.75mL/min, keeping the mixed ester for 5 minutes at the reaction temperature of 65 ℃; the obtained sample is the iso-ester, the mass of the obtained iso-ester is 22.1g, and the yield is 95.92%; dissolving 22.1g (0.192mol) of iso-ester by 40g of dichloromethane, dissolving 12g (0.2mol) of isopropylamine by 77.5g of dichloromethane, pumping the prepared two solutions into a microreactor, controlling the flow rate ratio of the iso-ester to the isopropylamine to be 2:3, the reaction temperature to be 50 ℃, the retention time to be 2min, collecting the effluent liquid, evaporating and drying to obtain a white solid, namely a crude product of the butylthiosemicarbazide, recrystallizing the crude product of the butylthiosemicarbazide by ethanol, and drying to obtain a pure product of the butylthiosemicarbazide, wherein the mass is 32.28g, the single-step yield is 96.47%, and the total yield is 92.60%.
Example 2
14.8g (0.2mol) of tert-butanol and 15.2g (0.22mol) of ammonium thiocyanate were dissolved in 19g of water to give a homogeneous solution, ready for use. Pumping the prepared solution and 20% hydrochloric acid solution into a microreactor through a high-pressure injection pump, wherein the flow rate ratio of tert-butyl alcohol-ammonium thiocyanate solution to hydrochloric acid is 3:2, reacting the reaction solution at 85 ℃, adjusting the outlet pressure of the reactor to enable the reaction solution to stably flow in a reaction system, the reaction retention time is 10 minutes, allowing the effluent liquid to enter a microflow field extraction device, and separating out an aqueous phase and an organic phase through a membrane separator after the effluent liquid stays for 3 minutes, wherein the organic phase is mixed ester, but a small amount of solid is adsorbed in the membrane separator; pumping the mixed ester into a microreactor fixedly loaded with zinc chloride, wherein the reaction temperature is 65 ℃, and the mixed ester stays for 5 minutes; the obtained sample is the isopropyl ester, the mass of the isopropyl ester is 21.3g, and the yield is 92.45%; dissolving 21.3g (0.185mol) of iso-ester by 40g of dichloromethane, dissolving 12g (0.2mol) of isopropylamine by 77.5g of dichloromethane, pumping the two prepared solutions into a microreactor, controlling the flow rate ratio of two phases of iso-ester and isopropylamine to be 2:3, the reaction temperature to be 50 ℃, the retention time to be 2min, collecting the effluent liquid, evaporating and drying to obtain a white solid, namely a crude product of butylthiosemicarbazide, recrystallizing the crude product of butylthiosemicarbazide by ethanol, and drying to obtain a pure product of butylthiosemicarbazide, wherein the mass is 31.12g, the single-step yield is 96.50%, and the total yield is 89.26%
Example 3
16.3g (0.22mol) of tert-butanol and 15.2g (0.2mol) of ammonium thiocyanate were dissolved in 19g of water to give a homogeneous solution, ready for use. Pumping the prepared solution and 20% hydrochloric acid solution into a microreactor through a high-pressure injection pump, wherein the flow rate ratio of tert-butyl alcohol-ammonium thiocyanate solution to hydrochloric acid is 3:2, reacting the reaction solution at 75 ℃, the reaction retention time is 10 minutes, feeding the effluent liquid into a microflow field extraction device, and separating a water phase and an organic phase through a membrane separator after the effluent liquid stays for 3 minutes, wherein the organic phase is mixed ester; pumping the mixed ester into a microreactor fixedly loaded with zinc chloride, wherein the reaction temperature is 65 ℃, and the mixed ester stays for 5 minutes; the obtained sample is the iso-ester, the mass of the obtained iso-ester is 21.6g, and the yield is 93.75%; dissolving 21.6g (0.188mol) of iso-ester by 40g of dichloromethane, dissolving 12g (0.2mol) of isopropylamine by 77.5g of dichloromethane, pumping the prepared two solutions into a microreactor, controlling the flow rate ratio of two phases of iso-ester and isopropylamine to be 2:3, the reaction temperature to be 50 ℃, the retention time to be 2min, collecting the effluent liquid, evaporating and drying to obtain a white solid, namely a crude product of butylthiosemicarbazide, recrystallizing the crude product of butylthiosemicarbazide by ethanol, and drying to obtain a pure product of butylthiosemicarbazide, wherein the mass is 31.54g, the single-step yield is 96.25%, and the total yield is 90.47%
Example 4
16.3g (0.22mol) of tert-butanol and 15.2g (0.2mol) of ammonium thiocyanate were dissolved in 19g of water to give a homogeneous solution, ready for use. Pumping the prepared solution and 20% hydrochloric acid solution into a microreactor through a high-pressure injection pump, wherein the flow rate ratio of tert-butyl alcohol-ammonium thiocyanate solution to hydrochloric acid is 3:2, reacting the reaction solution at 85 ℃, adjusting the outlet pressure of the reactor to enable the reaction solution to stably flow in a reaction system, the reaction retention time is 10 minutes, allowing the effluent liquid to enter a microflow field extraction device, and separating a water phase and an organic phase through a membrane separator after the effluent liquid stays for 3 minutes, wherein the organic phase is mixed ester; pumping the mixed ester into a microreactor fixedly loaded with zinc chloride, wherein the reaction temperature is 65 ℃, and the mixed ester stays for 5 minutes; the obtained sample is the iso-ester, the mass of the obtained iso-ester is 21.9g, and the yield is 95.05%; dissolving 21.9g (0.19mol) of iso-ester by 40g of dichloromethane, dissolving 12g (0.2mol) of isopropylamine by 77.5g of dichloromethane, pumping the prepared two solutions into a microreactor, controlling the flow rate ratio of two phases of iso-ester and isopropylamine to be 2:3, the reaction temperature to be 30 ℃, the retention time to be 2min, collecting the effluent liquid, evaporating and drying to obtain a white solid, namely a crude product of butylthiosemicarbazide, recrystallizing the crude product of butylthiosemicarbazide by ethanol, and drying to obtain a pure product of butylthiosemicarbazide, wherein the mass is 25.48g, the single-step yield is 76.93%, and the total yield is 73.09%
Example 5
The difference between this example and example 1 is that the reaction is set up as a simple continuous device to carry out an amplification experiment on example 1. Ammonium thiocyanate in mass ratio: preparing an ammonium thiocyanate solution by using water in a ratio of 4:5, pumping tertiary butanol and the prepared ammonium thiocyanate solution into a micro mixer according to a flow rate ratio of 1:2.7, and obtaining ammonium thiocyanate with a molar ratio of: the tertiary butanol is a solution of 1:1.1, the solution and 20% hydrochloric acid are directly pumped into a microreactor according to the flow rate ratio of 3:2, the reaction temperature is 85 ℃, the reaction residence time is 10 minutes, the liquid flowing out of an outlet enters a microflux field extraction device, the flowing-out organic phase is mixed ester, the mixed ester is pumped into the microreactor fixedly carrying zinc chloride along a pipeline, the reaction temperature is controlled at 65 ℃, the reaction residence time is 5 minutes, the liquid flowing out of the outlet is iso-ester, the iso-ester flows into a reaction temporary storage tank, the iso-ester and dichloromethane are pumped into a micromixer according to the flow rate of 1:1.3, and the mass ratio of isopropyl amine: and (3) preparing an isopropylamine solution from 13:84 dichloromethane, pumping the isopropylamine solution and the isopropyl amine solution into the microreactor at the same time, controlling the two-phase flow rate ratio of the isopropyl ester to the isopropyl amine to be 2:3, the reaction temperature to be 50 ℃, the retention time to be 2min, and collecting the effluent reaction liquid for 20 min. And distilling the effluent reaction liquid under reduced pressure to obtain a crude product of the butylpropylthiourea, recrystallizing the crude product of the butylpropylthiourea with ethanol, and drying to obtain a pure product of the butylpropylthiourea, wherein the total amount is 374.8g, 405.4g of the butylpropylthiourea can be obtained by calculating the feeding amount of the ammonium thiocyanate solution in 20 minutes, and the actual yield is 92.45%.
While the invention has been described with respect to a number of specific embodiments and methods, it will be appreciated by those skilled in the art that various modifications, additions and substitutions can be made without departing from the scope and spirit of the invention. All the components not specified in the present embodiment can be realized by the prior art.
Claims (10)
1. A method for preparing butylthiosemicarbazide by a micro-flow field reaction technology is characterized by comprising the following steps:
(1) dissolving tert-butyl alcohol and ammonium thiocyanate in water, and mixing to obtain a homogeneous solution A;
(2) pumping the homogeneous phase solution A and a hydrochloric acid solution into a microreactor and an extraction device I simultaneously, reacting and extracting, and collecting an organic phase liquid, namely a mixture of tert-butyl thiocyanate and tert-butyl isothiocyanate, which is called mixed ester for short;
(3) pumping the obtained mixed ester into a microreactor II which is fixedly loaded with a catalyst for reaction, and collecting effluent liquid, namely tert-butyl isothiocyanate, namely isopropyl ester for short;
(4) dissolving the obtained isopropyl ester in a first organic solvent to obtain a homogeneous phase solution B; dissolving isopropylamine in a second organic solvent to obtain a homogeneous solution C;
(5) and respectively pumping the homogeneous solution B and the homogeneous solution C into the microreactor III at the same time, reacting, collecting effluent liquid, and performing aftertreatment to obtain the thiobutyronitrile.
2. The method for preparing butylthiosemicarbazide by the micro-flow field reaction technology as claimed in claim 1, wherein in the step (1), the molar ratio of ammonium thiocyanate to tertiary butanol in the homogeneous solution A is controlled to be 1: 0.8-1.5, and the mass ratio of ammonium thiocyanate to water is 1: 1.0-3.0.
3. The method for preparing the thiobutanamide by the micro-flow field reaction technology according to claim 1, wherein in the step (2), the reaction molar ratio of the ammonium thiocyanate to the hydrogen chloride in the hydrochloric acid is controlled to be 1: 0.8-1.5, and the reaction molar ratio is controlled by the flow rate ratio of the homogeneous solution A and the hydrochloric acid solution pumped into the microreactor & extraction device I.
4. The method for preparing the thiobutazine by the micro-flow field reaction technology according to the claim 1, characterized in that, in the step (2), the micro-reactor and the extraction device I are an integrated continuous micro-flow control platform formed by connecting a micro-flow field reactor and a micro-flow field extraction device in series; the reaction temperature in the micro-flow field reactor is 60-110 ℃, and the reaction retention time is 1-15 min; the extraction retention time in the micro-flow field extraction device is 1-5 min.
5. The method for preparing the thiobutazine by the micro-flow field reaction technology as claimed in claim 1, wherein in the step (3), a catalyst is immobilized in the inner wall or the internal component of the micro-reactor II, the catalyst is selected from zinc chloride, the reaction temperature is 40-90 ℃, and the reaction residence time is 1-15 min.
6. The method for preparing thiobutanamide by micro-flow field reaction technique as claimed in claim 1, wherein in step (4), the first organic solvent and the second organic solvent are both organic solvents capable of dissolving thiobutanamide, isopropyl ester and isopropyl amine, and the solvents do not react with the three substances.
7. The method for preparing the thiobutanamide by the micro-flow field reaction technology according to claim 1, wherein in the step (5), the reaction molar ratio of the isopropyl ester to the isopropylamine is controlled to be 1: 1.0-1.5, and the reaction molar ratio is controlled by the flow rate ratio of pumping the homogeneous solution B and the homogeneous solution C into the microreactor III.
8. The method for preparing butathiosemicarbazide by the micro-flow field reaction technology as claimed in claim 1, wherein in the step (5), the reaction temperature is 0-100 ℃, and the reaction residence time is 1-15 min.
9. The method for preparing butathiosemicarbazide by the micro-flow field reaction technology as claimed in claim 1, wherein in the step (5), the post-treatment process comprises evaporation drying, recrystallization and/or pulping purification operations.
10. The method for preparing the butathiosemicarbazide by the micro-flow field reaction technology as claimed in claim 1, wherein in the step (2), the water phase obtained after extraction is neutralized by acid and alkali, and is recovered by distillation means and is used for the dissolving operation in the step (1); in the step (5), the obtained organic solution containing isopropylamine is subjected to post-treatment, and can be used for dissolving isopropylamine in the step (4).
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101973962A (en) * | 2010-11-01 | 2011-02-16 | 连云港市金囤农化有限公司 | Preparation method of buprofezin |
| CN105017114A (en) * | 2014-04-30 | 2015-11-04 | 连云港市金囤农化有限公司 | Preparation method of 1-isopropyl-3-tert-butylthiourea |
| CN108530388A (en) * | 2018-03-28 | 2018-09-14 | 江苏安邦电化有限公司 | A kind of preparation method of Buprofezin |
| CN112774606A (en) * | 2020-12-24 | 2021-05-11 | 安道麦安邦(江苏)有限公司 | Production method and equipment of high-purity buprofezin intermediate 1-isopropyl-3-tert-butylthiourea |
| CN113651771A (en) * | 2021-08-10 | 2021-11-16 | 安徽广信农化股份有限公司 | Synthesis method of combined buprofezin |
-
2022
- 2022-03-11 CN CN202210243185.3A patent/CN114573487A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101973962A (en) * | 2010-11-01 | 2011-02-16 | 连云港市金囤农化有限公司 | Preparation method of buprofezin |
| CN105017114A (en) * | 2014-04-30 | 2015-11-04 | 连云港市金囤农化有限公司 | Preparation method of 1-isopropyl-3-tert-butylthiourea |
| CN108530388A (en) * | 2018-03-28 | 2018-09-14 | 江苏安邦电化有限公司 | A kind of preparation method of Buprofezin |
| CN112774606A (en) * | 2020-12-24 | 2021-05-11 | 安道麦安邦(江苏)有限公司 | Production method and equipment of high-purity buprofezin intermediate 1-isopropyl-3-tert-butylthiourea |
| CN113651771A (en) * | 2021-08-10 | 2021-11-16 | 安徽广信农化股份有限公司 | Synthesis method of combined buprofezin |
Non-Patent Citations (2)
| Title |
|---|
| 凌 芳 等: "微通道反应器的发展研究进展", 上海化工, vol. 42, no. 4, pages 35 - 38 * |
| 吴 迪 等: "微反应器技术及其研究进展", 中国陶瓷工业, vol. 25, no. 5, pages 19 - 26 * |
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