CN117024310A - Method for continuously synthesizing hydroxamic acid compounds by utilizing microreactor - Google Patents
Method for continuously synthesizing hydroxamic acid compounds by utilizing microreactor Download PDFInfo
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- CN117024310A CN117024310A CN202310883304.6A CN202310883304A CN117024310A CN 117024310 A CN117024310 A CN 117024310A CN 202310883304 A CN202310883304 A CN 202310883304A CN 117024310 A CN117024310 A CN 117024310A
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- microreactor
- hydroxamic acid
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- hydroxylamine
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- 238000000034 method Methods 0.000 title claims abstract description 36
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000002253 acid Substances 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 title abstract description 8
- 230000002194 synthesizing effect Effects 0.000 title abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000003513 alkali Substances 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims abstract description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002443 hydroxylamines Chemical class 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000012266 salt solution Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 claims 1
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 3
- 229960001171 acetohydroxamic acid Drugs 0.000 description 3
- 230000006978 adaptation Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006146 oximation reaction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005112 continuous flow technique Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- KTHCAJSGBFXFKE-UHFFFAOYSA-N n-hydroxyfuran-2-carboxamide Chemical compound ONC(=O)C1=CC=CO1 KTHCAJSGBFXFKE-UHFFFAOYSA-N 0.000 description 1
- AWJLBFXUZYCIIH-UHFFFAOYSA-N n-hydroxypyridine-2-carboxamide Chemical compound ONC(=O)C1=CC=CC=N1 AWJLBFXUZYCIIH-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for continuously synthesizing hydroxamic acid compounds by utilizing a microreactor, belonging to the field of chemical synthesis of the biochemical technology. The method comprises the following steps: continuously inputting hydroxylamine salt solution and alkali solution into a pre-cooling/heating microreactor through a metering pump, mixing, neutralizing on-line free hydroxylamine with acid and alkali, mixing with raw material ester which is input into the microreactor through a metering pump, reacting completely, flowing reaction liquid out of the microreactor into a collecting kettle, regulating pH to be 3-4 by using 10wt% hydrochloric acid, and finally obtaining the hydroxamic acid compound. The invention adopts the micro-reaction technology to realize the continuous synthesis of the hydroxamic acid compound, has simple process flow and short reaction time, is easy to realize the automatic control of the technological process, adopts water as a reaction medium, has no organic solvent, improves the safety of the process and reduces the production cost. The conversion rate of the raw material ester is more than 99 percent, and the yield of the hydroxamic acid is 58-97 percent, thereby providing a feasible method for industrially producing hydroxamic acid compounds.
Description
Technical Field
The invention belongs to the field of chemical synthesis of micro-chemical technology, and in particular relates to a method for continuously preparing a hydroxamic acid compound by utilizing a micro-reactor.
Background
The wide application of hydroxamic acid compounds in biological activity, medicine, mineral flotation agents and the like is receiving more and more attention. Meanwhile, because of tautomerism and nitroxide double coordination function of the chemical structure, the method is widely applied to biology and organic synthesis methodologies.
At present, the hydroxamic acid synthesis is mainly performed in an intermittent kettle, and is influenced by the mass and heat transfer efficiency of the hydroxamic acid synthesis, so that the problems of low oximation rate, multiple side reactions, easiness in generating hot spots in the reaction process and the like exist. The invention provides a method for continuously preparing hydroxamic acid by utilizing a microreactor aiming at the problems existing in the reaction process of synthesizing hydroxamic acid by using a batch kettle.
In contrast to batch tanks, continuous flow processes feed the reaction mass into the microreactor at a constant flow rate and continuously produce the product. Meanwhile, the micro-reactor has the advantages of high heat and mass transfer coefficient, good mixing performance, narrow residence time distribution, easy realization of automatic control and integration of the technological process, and the like. The advantage of the continuous synthesis method of the microreactor is utilized, the rapid transfer of substances and heat in the preparation process of the hydroxamic acid is realized, the occurrence of side reaction is effectively reduced, and the process safety is improved, so that obvious changes are generated in the aspects of conversion rate, selectivity and safety. The micro-reactor is adopted to continuously prepare the hydroxamic acid, so that a new solution is provided for solving the problems existing in the intermittent kettle preparation process.
Disclosure of Invention
In order to solve the problems existing in the prior batch kettle production process of hydroxamic acid, the invention provides a method for continuously preparing hydroxamic acid by utilizing a microreactor. By utilizing the efficient mass and heat transfer characteristics of the microreactor, the mass transfer of substances and heat in the reaction process is enhanced, the volume and the reaction time of the microreactor can be obviously reduced, the occurrence of side reactions is reduced, the reaction selectivity is improved, and the process safety is improved. Compared with the traditional batch kettle type preparation process, the method can realize continuous production of the hydroxamic acid, has the advantages of high raw material oximation rate, less side reaction, high yield, no organic solvent, less three wastes, environmental friendliness and extremely high commercial value.
A method for continuously preparing hydroxamic acid by utilizing a microreactor comprises the steps of mixing and reacting hydroxylamine salt solution with alkali solution in a first-stage microreactor at a reaction temperature, mixing and reacting with raw material ester in a second-stage microreactor, entering a collecting kettle after the reaction is completed, and adjusting pH=3-4 by using hydrochloric acid to obtain the corresponding hydroxamic acid.
Further, in the above technical scheme, the hydroxamic acid and the raw ester have chemical structures as shown in formula I and formula II:
r in the formula I and the formula II is:(R 1 ＝H，Cl，Br，I，NO 2 ，CH 3 ，)，/>-alkyl，H，(R 2 ＝C1～C5)。
further, in the above technical scheme, the first-stage microreactor and the second-stage microreactor comprise microchannel reactors, tubular reactors, microtube-type filler reactors and combinations thereof, and the first-stage microreactor and the second-stage microreactor are internally provided with micro heat exchangers.
Further, in the technical scheme, the molar concentration of the hydroxylamine salt solution and the alkali solution is respectively 1-5 mol/l; mixing and reacting hydroxylamine salt solution and alkali solution in a first stage microreactor to obtain hydroxylamine, wherein the molar ratio of the hydroxylamine to the alkali is 1:1.5-2.2.
Further, in the above technical scheme, -alkyl is preferably C1-C5 alkane.
Further, in the technical scheme, the molar ratio of the ester to the hydroxylamine is 1:1-1.08.
Further, in the technical scheme, the reaction temperature of the materials in the reactor is-10 ℃ to 50 ℃.
Further, in the technical scheme, the retention time of the materials in the first-stage micro-reactor is 10 s-30 s, the retention time of the materials in the second-stage micro-reactor is 20 s-4.5 min, and the total retention time of the materials from entering the first-stage micro-reactor to exiting the second-stage micro-reactor is 0.5-5 min.
Further, in the above technical scheme, 5 to 20wt% hydrochloric acid is used to adjust ph=3 to 4, to obtain a hydroxamic acid product.
The beneficial effects of the invention are as follows: (1) Realizing the continuous preparation of different hydroxamic acids in a microreactor; (2) Compared with the intermittent kettle type process, the invention adopts the continuous preparation process of the micro-reactor, so that the mixing efficiency is high, the mass and heat transfer coefficients are high, the temperature in the reaction process is highly controllable, the side reaction is effectively reduced, and the yields of fatty hydroxamic acid, pyridine hydroxamic acid and furan hydroxamic acid are improved; (3) The micro-reactor has small volume, simplifies the process flow, and is easy to realize the automatic control and the integrated amplification of the process flow; (4) The process of the invention uses water as solvent, has no organic solvent, high safety, environment-friendly production process and good application value.
The characteristic advantages of the invention will be apparent from the following description of the examples of embodiment.
Drawings
FIG. 1, a flow chart for the continuous preparation of hydroxamic acid according to the present invention.
Detailed Description
The invention will be further illustrated by the following examples, which are not intended to limit the scope of the invention, in order to provide a better understanding of the invention to those skilled in the art. The reagents used in the examples are all commercially available, and the technical means used in the examples are conventional means well known to those skilled in the art.
Example 1
The specific steps for continuously preparing acetyl hydroxamic acid by the microreactor are as follows:
examples the microreaction system is adopted, the reaction temperature and the total residence time of the materials from entering the first stage microreactor to exiting the second stage microreactor are respectively represented by T and tau, and the process for continuously preparing hydroxamic acid by the microreaction is shown in figure 1. The micro-reaction system comprises a hydroxylamine solution storage tank and an alkali solution storage tank which are respectively connected to the micro-reactor 1 through pumps; the outlet of the micro-reactor 1 is sequentially connected with the micro-reactor 2 and the product collecting kettle. The ester feed stock tank is connected to the microreactor 2 by a pump. The outside of the microreactor 1 and the microreactor 2 is provided with circulating water.
Firstly, hydroxylamine hydrochloride aqueous solution (3.0 mol/l, Q=7.0 ml/min) and sodium hydroxide aqueous solution (3.0 mol/l, Q=18.0 ml/min) are continuously input into a micro-reactor 1 through a pump 1 and a pump 2 to be mixed and reacted, the mixture enters the micro-reactor 2 after flowing out of the micro-reactor 1, the mixture is mixed and reacted with ethyl acetate (Q=2.0 ml/min) input through the pump 3, the retention time of the mixture in the first-stage micro-reactor 1 is 19s, the retention time in the second-stage micro-reactor 2 is 55s, the temperature of the micro-reactor 1 and the micro-reactor 2 is controlled to be 15 ℃ through external circulation, after the reaction is completed, the mixture flows out of the reactor and enters a collecting kettle, and the pH=3-4 is regulated by 10wt% hydrochloric acid, so that the acetyl hydroxamic acid is obtained. And analyzing the component content by a liquid chromatography area normalization method. Analyzed: the conversion rate of the raw material ester is more than 99.9%, the product acetyl hydroxamic acid is 98.4%, and the impurity is 1.6%.
Examples 2 to 11
The microreactor continuously prepares other hydroxamic acids as follows:
other hydroxamic acids were continuously prepared in the same manner as in example 1. The reaction temperature and residence time of the microreactor during the reaction were varied, and the specific results are shown in Table 1.
TABLE 1 continuous preparation of different hydroxamic acids by microreactors
By the method for continuously preparing different types of hydroxamic acid by utilizing the microreactor, the material and heat transfer in the reaction process is enhanced, and the raw material conversion rate and the product yield are effectively improved. Meanwhile, the method takes water as a solvent, has no organic solvent, has low production cost and safe process, and has extremely high commercial development value.
Those skilled in the art will appreciate that certain modifications and adaptations of the invention may be made. Such modifications and adaptations are intended to be within the scope of the present invention as defined in the appended claims.
Claims (10)
1. A method for continuously preparing hydroxamic acid using a microreactor, comprising the steps of: mixing and reacting hydroxylamine salt solution and alkali solution in a first-stage microreactor at the reaction temperature, mixing and reacting with raw material ester in a second-stage microreactor, entering a collecting kettle after the reaction is completed, and adjusting the pH value to be 3-4 by using hydrochloric acid to obtain the corresponding hydroxamic acid.
2. The method according to claim 1, wherein: the hydroxamic acid and the raw material ester have chemical structures shown in the formulas I and II:
r in the formula I and the formula II is:(R 1 ＝H，Cl，Br，I，NO 2 ，CH 3 ，)，/>-alkyl，H，(R 2 ＝C1～C5)。
3. the method according to claim 1, wherein: the hydroxylamine salt comprises hydroxylamine hydrochloride and hydroxylamine sulfate.
4. The method according to claim 1, wherein: the alkali liquor comprises sodium hydroxide aqueous solution and potassium hydroxide aqueous solution.
5. The method according to claim 1, wherein: the first-stage microreactor and the second-stage microreactor comprise a multichannel microreactor, a tubular reactor, a microtube type filler reactor and a combination thereof.
6. The method according to claim 1, wherein: the reaction temperature is controlled between-10 ℃ and 50 ℃.
7. The method according to claim 1, wherein: the molar ratio of hydroxylamine salt to alkali is 1:1.5-2.2.
8. The method according to claim 1, wherein: mixing and reacting hydroxylamine salt solution and alkali solution in a first stage microreactor to obtain hydroxylamine, wherein the molar ratio of ester to hydroxylamine is 1:1-1.08.
9. The method according to claim 1, wherein: the residence time in the first-stage micro-reactor is 10 s-30 s, the residence time in the second-stage micro-reactor is 20 s-4.5 min, and the total residence time of the materials from entering the first-stage micro-reactor to exiting the second-stage micro-reactor is 0.5-5 min.
10. The method according to claim 1, wherein: the solvent used was water.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310883304.6A CN117024310A (en) | 2023-07-18 | 2023-07-18 | Method for continuously synthesizing hydroxamic acid compounds by utilizing microreactor |
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| CN202310883304.6A CN117024310A (en) | 2023-07-18 | 2023-07-18 | Method for continuously synthesizing hydroxamic acid compounds by utilizing microreactor |
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