CN104447246A - Method for preparing o-methoxybenzaldehyde by using micro-reaction device - Google Patents
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 74
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 26
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 239000012043 crude product Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 46
- 239000000243 solution Substances 0.000 claims description 23
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 2
- 230000003321 amplification Effects 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 2
- 239000012456 homogeneous solution Substances 0.000 abstract 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005086 pumping Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 239000012530 fluid Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
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- 150000001299 aldehydes Chemical class 0.000 description 3
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- 238000005516 engineering process Methods 0.000 description 3
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
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- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
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- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
- 229960003022 amoxicillin Drugs 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing o-methoxybenzaldehyde by a micro-reaction device, which comprises the following steps: dissolving salicylaldehyde in a strong alkali water solution to obtain a homogeneous solution; dissolving dimethyl sulfate in an organic solvent to obtain a homogeneous solution; respectively and simultaneously pumping the two homogeneous phase solutions into a micro-reaction device, wherein the reaction temperature is 70-120 ℃, and the reaction residence time is 1-10 min; collecting the effluent liquid, namely the o-methoxybenzaldehyde crude product. The micro-reactor has the advantages of large specific surface area, high transfer rate, short contact time, few by-products and very strong heat transfer and mass transfer capacities; rapid and direct amplification, high safety, good operability and the like.
Description
Technical field
The invention belongs to chemosynthesis technical field, be specifically related to a kind of method utilizing micro-reaction device to prepare o-methoxybenzaldehyde.
Background technology
O-methoxybenzaldehyde, also known as sweet fennel aldehyde, is a kind of organic synthesis intermediate, for medicine, food and daily chemical industry.Be widely used in the spices of preparation floral type as middle taste type spices, it has lasting hawthorn fragrance, in may blossom, sunflower, Syringa oblata Lindl. essence, do main body fragrant material; Modifier is made in osmanthus flower fragrance; Also can be used for daily essence and food flavor(ing), coordinate with the essential oil of tangerine orange etc., effect is fine.For the manufacture of antimicrobial medicine amoxycillin etc. in medicine industry, it is the intermediate of antihistamine drug.As the excellent brightening agent of non-cyanogen galvanization DE additive, anodic polarization can be improved in wider current density range, obtain bright coating.
The preparation of o-methoxybenzaldehyde has many methods.1. plant extraction method: sweet fennel aldehyde is present in the natural matters such as olium anisi, oleum anethi, Acacia caul-fat, vanilla medicinal extract, can add some oxygenant Sum decomposition agent to extract anisyl aldehyde.But this complex process, yield is low, is eliminated at present; 2. chemical synthesis: different according to raw material sources, have kinds of processes route, as ortho-cresol method, methyl-phenoxide method, O-methoxy toluene oxidation method, p-Hydroxybenzaldehyde methylation method etc., each method has its relative merits.
Microreactor be a kind of by means of special micro-processing with the three-dimensional structure element that can be used for carrying out chemical reaction of solid substrate manufacture.Microreactor is usually containing little channel size (equivalent diameter is less than 500 μm) and passage diversity, and fluid flows in these passages, and requires the reaction in these passages required by generation.Which results in, in the chemical device of micro-structure, there is very large surface area/volume ratio rate.The people such as G.WieBmeier describe the micro passage reaction for heterogeneous catalytic reaction in micro-reacting tcchnology international conference.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of efficient, free of contamination method utilizing micro-reaction device to prepare o-methoxybenzaldehyde.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows:
Micro-reaction device prepares a method for o-methoxybenzaldehyde, and it comprises the steps:
(1) salicylic aldehyde is dissolved in strong alkali aqueous solution, obtains homogeneous phase solution;
(2) methyl-sulfate is dissolved in organic solvent, obtains homogeneous phase solution;
(3) pumped into respectively in micro-reaction device by two kinds of homogeneous phase solutions that step (1) and step (2) obtain, temperature of reaction is 70 ~ 120 DEG C simultaneously, and reaction time is 1 ~ 10min;
(4) collect flowing liquid, be o-methoxybenzaldehyde crude product.
In step (1), described highly basic is sodium hydroxide or potassium hydroxide.
In step (1), in the homogeneous phase solution obtained, the concentration of salicylic aldehyde is 0.1 ~ 0.2g/ml, and the mol ratio of salicylic aldehyde and highly basic is 1:1.0 ~ 1.2.
In step (2), described organic solvent is tetrahydrofuran (THF), dimethyl formamide, Isosorbide-5-Nitrae-dioxane or for its derivative kind solvent.
In step (2), in the homogeneous phase solution obtained, the concentration of methyl-sulfate is 0.1 ~ 0.3g/ml.
In step (3), described micro-reaction device is by the liquor inlet be linked in sequence by pipe connecting, T-shaped mixing valve, micro passage reaction and material liquid outlet.
Wherein, the diameter of described pipe connecting is 0.8 ~ 2mm.
Wherein, described micro passage reaction volume is 2 ~ 10ml.
In step (3), the reaction mol ratio of salicylic aldehyde and methyl-sulfate controls in 1:1.0 ~ 1.5.
In step (3), two kinds of homogeneous phase solution flow velocitys are 0.1 ~ 5ml/min.
In step (3), temperature of reaction is preferably 70 ~ 100 DEG C, and reaction time is 1 ~ 10min.
Beneficial effect: microreactor has that specific surface area is large, and transfer rate is high, and duration of contact is short, and by product is few, heat transfer, mass transfer ability are very strong; Amplify fast, directly, the features such as security is high, good operability; Micro-reactive system is the parallel system in modular structure, there is good portability feature, can realize making land used disperse construction also to produce on the spot, supply at product, real realization is by chemical plant portability, and can according to market situation increase and decrease port number and change module regulate production, there is very high turndown ratio.O-methoxybenzaldehyde production method technique provided by the invention is simple, can continuous seepage, there is higher processing safety and higher selectivity, reaction volume be little, the time is short less to equipment corrosion; Most importantly overcome methyl-sulfate to the pollution of the injury of the person to environment, operation full safety is closed.Meanwhile, utilize the High Efficiency Thermal mass transfer ability of micro passage reaction and be easy to the feature of directly amplification, transforming rate high is more than 85%, and good product quality, energy consumption are low, is a kind of method that o-methoxybenzaldehyde is synthesized in environmental protection efficiently.
Accompanying drawing explanation
Fig. 1 is the structural representation of micro passage reaction of the present invention.
Fig. 2 is reaction formula of the present invention.
Embodiment
According to following embodiment, the present invention may be better understood.But those skilled in the art will readily understand, the content described by embodiment only for illustration of the present invention, and should can not limit the present invention described in detail in claims yet.
Following microchannel reaction unit is by the liquor inlet be linked in sequence by pipe connecting, T-shaped mixing valve, micro passage reaction and material liquid outlet, Fig. 1 is shown in concrete assembling, wherein two reaction raw materials storage tanks connect respective liquor inlet by pipe connecting and are connected with T-shaped mixing valve respectively, this pipe connecting is respectively equipped with pump, T-shaped mixing valve is connected with micro passage reaction by pipe connecting, micro passage reaction is connected with material liquid outlet by pipe connecting, described head tank is the Erlenmeyer flask of 250ml, micro passage reaction model is vapourtac R series, be purchased from De Xiang International Technology company.The reagent used in experiment is all AR, all purchased from Shanghai Ling Feng chemical reagent company limited.
Embodiment 1:
In the reaction unit of microchannel, pipe connecting diameter is 0.8mm, and liquid-inlet pipe length is 15cm, and the pipe connecting length between T-shaped valve and micro passage reaction is 32cm, and the pipe connecting length between microreactor and outlet is 32cm; Micro passage reaction volume is 5ml.
Get salicylic aldehyde 0.025mol (3.05g), join in the aqueous solution containing 0.025mol sodium hydroxide and stir in homogeneous phase, obtain mixeding liquid volume 30mL; Take 0.025mol (3.15g) methyl-sulfate, add THF and be diluted to 30mL.Two kinds of materials are entered in micro passage reaction by T-shaped valve mixing pump.Two kinds of reaction solution fluids flow through microreactor with 2.5mL/min respectively, and the reaction mol ratio of salicylic aldehyde and methyl-sulfate is 1:1.0, and temperature of reactor is 110 DEG C, and reaction time is 1min, and thick product is collected in outlet; In thick product, add excessive sodium hydrate to be hydrolyzed residual methyl-sulfate, stirring is spent the night.Be extracted with ethyl acetate three times, recycling 1mol/L aqueous sodium hydroxide solution washing organic phase, adds anhydrous magnesium sulfate drying, revolves evaporate to dryness dry.Productive rate is 90.2%.
Embodiment 2:
In the reaction unit of microchannel, pipe connecting diameter is 2.0mm, and liquid-inlet pipe length is 15cm, and the pipe connecting length between T-shaped valve and micro passage reaction is 32cm, and the pipe connecting length between microreactor and outlet is 32cm; Micro passage reaction volume is 2ml.
Get salicylic aldehyde 0.025mol (3.05g), join in the aqueous solution containing 0.0275mol sodium hydroxide and stir in homogeneous phase, obtain mixeding liquid volume 30mL; Take 0.0275mol (3.47g) methyl-sulfate, add DMF and be diluted to 30mL.Two kinds of materials are entered in micro passage reaction by T-shaped valve mixing pump.Two kinds of reaction solution fluids flow through microreactor with 0.1mL/min respectively, and it is 1:1.1 that salicylic aldehyde and methyl-sulfate react mol ratio, and temperature of reactor is 90 DEG C, and reaction time is 10min, and thick product is collected in outlet; In thick product, add excessive sodium hydrate to be hydrolyzed residual methyl-sulfate, stirring is spent the night.Be extracted with ethyl acetate three times, recycling 1mol/L aqueous sodium hydroxide solution washing organic phase, adds anhydrous magnesium sulfate drying, revolves evaporate to dryness dry.Productive rate is 88.6%.
Embodiment 3:
In the reaction unit of microchannel, pipe connecting diameter is 1.0mm, and liquid-inlet pipe length is 15cm, and the pipe connecting length between T-shaped valve and micro passage reaction is 32cm, and the pipe connecting length between microreactor and outlet is 32cm; Micro passage reaction volume is 10ml.
Get salicylic aldehyde 0.05mol (6.05g), join in the aqueous solution containing 0.0525mol sodium hydroxide and stir in homogeneous phase, obtain mixeding liquid volume 40mL; Take 0.065mol (8.19g) methyl-sulfate, add dioxane and be diluted to 40mL.Two kinds of materials are entered in micro passage reaction by T-shaped valve mixing pump.Two kinds of reaction solution fluids flow through microreactor with 2.5mL/min respectively, and the reaction mol ratio of salicylic aldehyde and methyl-sulfate is 1:1.3, and temperature of reactor is 70 DEG C, and reaction time is 2min, and thick product is collected in outlet; In thick product, add excessive sodium hydrate to be hydrolyzed residual methyl-sulfate, stirring is spent the night.Be extracted with ethyl acetate three times, recycling 1mol/L aqueous sodium hydroxide solution washing organic phase, adds anhydrous magnesium sulfate drying, revolves evaporate to dryness dry.Productive rate is 95.6%.
Embodiment 4:
In the reaction unit of microchannel, pipe connecting diameter is 1.0mm, and liquid-inlet pipe length is 15cm, and the pipe connecting length between T-shaped valve and micro passage reaction is 32cm, and the pipe connecting length between microreactor and outlet is 32cm; Micro passage reaction volume is 5ml.
Get salicylic aldehyde 0.05mol (6.05g), join in the aqueous solution containing 0.055mol sodium hydroxide and stir in homogeneous phase, obtain mixeding liquid volume 40mL; Take 0.06mol (7.56g) methyl-sulfate, add DMF and be diluted to 40mL.Two kinds of materials are entered in micro passage reaction by T-shaped valve mixing pump.Two kinds of reaction solution fluids flow through microreactor with 2.5mL/min respectively, and the reaction mol ratio of salicylic aldehyde and methyl-sulfate is 1:1.2, and temperature of reactor is 120 DEG C, and reaction time is 1min, and thick product is collected in outlet; In thick product, add excessive sodium hydrate to be hydrolyzed residual methyl-sulfate, stirring is spent the night.Be extracted with ethyl acetate three times, recycling 1mol/L aqueous sodium hydroxide solution washing organic phase, adds anhydrous magnesium sulfate drying, revolves evaporate to dryness dry.Productive rate is 91.6%.
Embodiment 5:
In the reaction unit of microchannel, pipe connecting diameter is 1.2mm, and liquid-inlet pipe length is 15cm, and the pipe connecting length between T-shaped valve and micro passage reaction is 32cm, and the pipe connecting length between microreactor and outlet is 32cm; Micro passage reaction volume is 5ml.
Get salicylic aldehyde 0.05mol (6.05g), join in the aqueous solution containing 0.0525mol sodium hydroxide and stir in homogeneous phase, obtain mixeding liquid volume 32mL; Take 0.065mol (8.19g) methyl-sulfate, add DMF and be diluted to 32mL.Two kinds of materials are entered in micro passage reaction by T-shaped valve mixing pump.Two kinds of reaction solution fluids flow through microreactor with 1.25mL/min respectively, and the reaction mol ratio of salicylic aldehyde and methyl-sulfate is 1:1.3, and temperature of reactor is 70 DEG C, and reaction time is 2min, and thick product is collected in outlet; In thick product, add excessive sodium hydrate to be hydrolyzed residual methyl-sulfate, stirring is spent the night.Be extracted with ethyl acetate three times, recycling 1mol/L aqueous sodium hydroxide solution washing organic phase, adds anhydrous magnesium sulfate drying, revolves evaporate to dryness dry.Productive rate is 92.6%.
Claims (10)
1. micro-reaction device prepares a method for o-methoxybenzaldehyde, it is characterized in that, it comprises the steps:
(1) salicylic aldehyde is dissolved in strong alkali aqueous solution, obtains homogeneous phase solution;
(2) methyl-sulfate is dissolved in organic solvent, obtains homogeneous phase solution;
(3) pumped into respectively in micro-reaction device by two kinds of homogeneous phase solutions that step (1) and step (2) obtain, temperature of reaction is 70 ~ 120 DEG C simultaneously, and reaction time is 1 ~ 10min;
(4) collect flowing liquid, be o-methoxybenzaldehyde crude product.
2. micro-reaction device according to claim 1 prepares the method for o-methoxybenzaldehyde, it is characterized in that, in step (1), described highly basic is sodium hydroxide or potassium hydroxide.
3. micro-reaction device according to claim 1 and 2 prepares the method for o-methoxybenzaldehyde, it is characterized in that, in step (1), in the homogeneous phase solution obtained, the concentration of salicylic aldehyde is 0.1 ~ 0.2g/ml, and the mol ratio of salicylic aldehyde and highly basic is 1:1.0 ~ 1.2.
4. micro-reaction device according to claim 1 prepares the method for o-methoxybenzaldehyde, it is characterized in that, in step (2), described organic solvent is tetrahydrofuran (THF), dimethyl formamide, Isosorbide-5-Nitrae-dioxane or for its derivative kind solvent.
5. the micro-reaction device according to claim 1 or 4 prepares the method for o-methoxybenzaldehyde, it is characterized in that, in step (2), in the homogeneous phase solution obtained, the concentration of methyl-sulfate is 0.1 ~ 0.3g/ml.
6. micro-reaction device according to claim 1 prepares the method for o-methoxybenzaldehyde, it is characterized in that, in step (3), described micro-reaction device is by the liquor inlet be linked in sequence by pipe connecting, T-shaped mixing valve, micro passage reaction and material liquid outlet.
7. micro-reaction device according to claim 6 prepares the method for o-methoxybenzaldehyde, it is characterized in that, the diameter of described pipe connecting is 0.8 ~ 2mm.
8. micro-reaction device according to claim 6 prepares the method for o-methoxybenzaldehyde, it is characterized in that, described micro passage reaction volume is 2 ~ 10ml.
9. micro-reaction device according to claim 1 prepares the method for o-methoxybenzaldehyde, it is characterized in that, in step (3), the reaction mol ratio of salicylic aldehyde and methyl-sulfate controls in 1:1.0 ~ 1.5.
10. micro-reaction device according to claim 1 prepares the method for o-methoxybenzaldehyde, it is characterized in that, in step (3), two kinds of homogeneous phase solution flow velocitys are 0.1 ~ 5ml/min.
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Cited By (8)
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| CN105820349A (en) * | 2016-05-06 | 2016-08-03 | 南京工业大学 | Method for preparing polysaccharide-polyester graft copolymer by using micro-reaction device |
| CN106866380A (en) * | 2017-02-20 | 2017-06-20 | 河北工业大学 | A kind of micro- reactive distillation plate prepares the method and its equipment of 2,6 BHTs |
| CN106866453A (en) * | 2017-01-23 | 2017-06-20 | 齐鲁天和惠世制药有限公司 | A kind of method that microreactor prepares scheme for lacosamide |
| CN108017524A (en) * | 2017-11-24 | 2018-05-11 | 天津大学 | A kind of preparation method of 3,4,5-Trimethoxybenzaldehyde |
| CN109264744A (en) * | 2018-10-19 | 2019-01-25 | 湖南雅城新材料有限公司 | A kind of recovery method as resource of low cost ferric phosphate nitrogen-containing wastewater |
| CN109482119A (en) * | 2018-12-12 | 2019-03-19 | 西南大学 | A kind of the nano molecular sieve microreactor and preparation method of efficient production benzaldehyde |
| CN110256217A (en) * | 2019-04-29 | 2019-09-20 | 武汉理工大学 | A kind of preparation method of o-methoxybenzaldehyde |
| CN111302915A (en) * | 2020-03-05 | 2020-06-19 | 复旦大学 | Method for preparing anisaldehyde through micro-channel continuous ozone oxidation |
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| CN105820349A (en) * | 2016-05-06 | 2016-08-03 | 南京工业大学 | Method for preparing polysaccharide-polyester graft copolymer by using micro-reaction device |
| CN106866453A (en) * | 2017-01-23 | 2017-06-20 | 齐鲁天和惠世制药有限公司 | A kind of method that microreactor prepares scheme for lacosamide |
| CN106866380A (en) * | 2017-02-20 | 2017-06-20 | 河北工业大学 | A kind of micro- reactive distillation plate prepares the method and its equipment of 2,6 BHTs |
| CN106866380B (en) * | 2017-02-20 | 2020-04-07 | 河北工业大学 | Method and equipment for preparing 2, 6-di-tert-butyl-p-cresol by using micro-reaction rectifying plate |
| CN108017524A (en) * | 2017-11-24 | 2018-05-11 | 天津大学 | A kind of preparation method of 3,4,5-Trimethoxybenzaldehyde |
| CN108017524B (en) * | 2017-11-24 | 2021-03-12 | 天津大学 | Preparation method of 3, 4, 5-trimethoxybenzaldehyde |
| CN109264744A (en) * | 2018-10-19 | 2019-01-25 | 湖南雅城新材料有限公司 | A kind of recovery method as resource of low cost ferric phosphate nitrogen-containing wastewater |
| CN109482119A (en) * | 2018-12-12 | 2019-03-19 | 西南大学 | A kind of the nano molecular sieve microreactor and preparation method of efficient production benzaldehyde |
| CN109482119B (en) * | 2018-12-12 | 2021-05-07 | 西南大学 | Nano molecular sieve microreactor for efficiently producing benzaldehyde and preparation method thereof |
| CN110256217A (en) * | 2019-04-29 | 2019-09-20 | 武汉理工大学 | A kind of preparation method of o-methoxybenzaldehyde |
| CN110256217B (en) * | 2019-04-29 | 2020-08-04 | 武汉理工大学 | Preparation method of o-methoxybenzaldehyde |
| CN111302915A (en) * | 2020-03-05 | 2020-06-19 | 复旦大学 | Method for preparing anisaldehyde through micro-channel continuous ozone oxidation |
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