CN116410070A - Production process of p-fluoro-m-phenoxy benzaldehyde - Google Patents
Production process of p-fluoro-m-phenoxy benzaldehyde Download PDFInfo
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- CN116410070A CN116410070A CN202111665905.7A CN202111665905A CN116410070A CN 116410070 A CN116410070 A CN 116410070A CN 202111665905 A CN202111665905 A CN 202111665905A CN 116410070 A CN116410070 A CN 116410070A
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- fluoro
- phenoxy
- aldehyde
- fluoroether
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- JDICMOLUAHZVDS-UHFFFAOYSA-N 4-fluoro-3-phenoxybenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1OC1=CC=CC=C1 JDICMOLUAHZVDS-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 18
- ILKFYEKKPVEUOK-UHFFFAOYSA-N 1-fluoro-4-methyl-2-phenoxybenzene Chemical compound CC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 ILKFYEKKPVEUOK-UHFFFAOYSA-N 0.000 claims abstract description 16
- NJZKTQSPKJPMNT-UHFFFAOYSA-N 4-(dichloromethyl)-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(C(Cl)Cl)C=C1OC1=CC=CC=C1 NJZKTQSPKJPMNT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- WFUPNMGWVAEEFM-UHFFFAOYSA-N methoxycarbonyloxy methyl carbonate Chemical compound COC(=O)OOC(=O)OC WFUPNMGWVAEEFM-UHFFFAOYSA-N 0.000 claims description 3
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001774 Perfluoroether Polymers 0.000 abstract description 29
- 150000001299 aldehydes Chemical class 0.000 abstract description 29
- 239000000047 product Substances 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- FAHZIKXYYRGSHF-UHFFFAOYSA-N 3-bromo-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1Br FAHZIKXYYRGSHF-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- 238000005705 Cannizzaro reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- -1 azodiisoheptonitrile Chemical compound 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/24—Preparation of ethers by reactions not forming ether-oxygen bonds by elimination of halogens, e.g. elimination of HCl
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- 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 production process of p-fluoro-m-phenoxy benzaldehyde, which takes p-fluoro-m-phenoxy toluene as a raw material, and under the action of a catalyst, the p-fluoro-m-phenoxy toluene is converted into p-fluoro-m-phenoxy benzylidene dichloride with high selectivity, the p-fluoro-m-phenoxy benzylidene dichloride is hydrolyzed under alkaline conditions to generate the p-fluoro-m-phenoxy benzaldehyde, and the obtained crude fluoroether aldehyde is rectified to obtain refined fluoroether aldehyde, wherein the overall reaction yield is more than 89%. The invention improves the high selectivity and conversion rate of dichloro by selecting the high-efficiency catalyst, avoids the conditions of monochloro and excessive chloro, and the dichloro product is directly hydrolyzed under alkaline condition without purification to generate crude fluoroether aldehyde, and the crude fluoroether aldehyde is rectified to obtain refined fluoroether aldehyde. The method has the advantages of reasonable design of the process route, mild process conditions, high conversion rate of the synthesized product, few byproducts, high total yield and content of the product, low comprehensive cost required by production, no need of adding additional organic solvent in the chlorination process, and clean and efficient production process.
Description
Technical Field
The invention relates to a production method of a compound, in particular to a production process of p-fluoro-m-phenoxy benzaldehyde (fluoroether aldehyde), and belongs to the technical field of chemical synthesis.
Background
The traditional fluoroether aldehyde production method is to use p-fluorobenzaldehyde as a raw material, bromine is firstly used for brominating to obtain 3-bromo-4-fluorobenzaldehyde, and under alkaline conditions, the 3-bromo-4-fluorobenzaldehyde is easy to undergo a Cannizzaro reaction to generate corresponding acid and alcohol, so that glycol is used for reacting with 3-bromo-4-fluorobenzaldehyde to generate acetal to protect aldehyde groups, then etherification reaction is carried out with sodium phenolate, and finally hydrolysis is carried out to obtain the p-fluoro-m-phenoxy benzaldehyde. The method uses bromine for bromination, the reaction has high requirements on equipment, the wastewater is difficult to treat, the aldehyde group introduced groups are required to be protected during the reaction, the etherate is required to be hydrolyzed after the etherification reaction, the protecting groups are removed, the process flow is long, and the overall yield of the reaction is low.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention provides a production process of para-fluoro-m-phenoxy benzaldehyde (fluoroether aldehyde), which takes para-fluoro-m-phenoxy toluene as a raw material, prepares the para-fluoro-m-phenoxy benzaldehyde (fluoroether aldehyde) through high-selectivity dichlorination and hydrolysis, adds a high-efficiency selective catalyst in the chlorination process, converts the para-fluoro-m-phenoxy toluene into para-fluoro-m-phenoxy benzylidene dichloride, hydrolyzes the para-fluoro-m-phenoxy benzylidene dichloride to generate the para-fluoro-m-phenoxy benzaldehyde (fluoroether aldehyde), improves the high selectivity and conversion rate of dichloro by selecting the high-efficiency catalyst, avoids the conditions of monochloro and overchloro, and the chlorination product is directly hydrolyzed under alkaline conditions without purification to generate crude fluoroether aldehyde, and the crude fluoroether aldehyde is rectified to obtain refined fluoroether aldehyde. The process route is reasonable in design, mild in process condition, high in conversion rate of the synthesized product, few in byproducts, high in total yield and content of the product, low in comprehensive cost required by production, and free of additional organic solvent in the chlorination process, and is a clean and efficient production process.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a production process of p-fluoro-m-phenoxy benzaldehyde comprises the following steps:
adding a high-efficiency selective catalyst in the process of introducing chlorine into the para-fluoro-m-phenoxy toluene for chlorination reaction, and directly converting the para-fluoro-m-phenoxy toluene into para-fluoro-m-phenoxy benzylidene dichloride; the generated para-fluoro-meta-phenoxy benzylidene dichloride is subjected to hydrolysis reaction under alkaline conditions to generate para-fluoro-meta-phenoxy benzaldehyde; the chemical reaction formula is as follows:
in the technical proposal, the reaction temperature of the chlorination reaction carried out by introducing chlorine is 40-120 ℃ and the reaction time is 2-10hr.
In the technical scheme, the mass ratio of the p-fluoro-m-phenoxy toluene to the high-efficiency selective catalyst is 1:0.001-0.05.
In the above technical scheme, the high-efficiency selective catalyst is selected from any one, two or more than one of azodiisobutyronitrile, azodiisoheptonitrile, benzoyl peroxide, cyclohexanone peroxide, dimethyl azodiisobutyrate and dimethyl peroxydicarbonate, and the mixture is formed by mixing the two or more than one of the above components in any proportion.
In the technical scheme, the mass ratio of the p-fluoro-m-phenoxy toluene to the chlorine is 1:0.68-0.8.
In the technical scheme, the hydrolysis reaction is carried out at the temperature of 80-160 ℃ for 0.5-5hr.
In the above technical solution, the alkaline condition refers to a condition formed by adding an aqueous alkali solution, the aqueous alkali solution refers to an aqueous solution formed by dissolving alkali such as potassium hydroxide, potassium carbonate, sodium hydroxide, sodium carbonate, cesium carbonate, hexamethylenetetramine and the like in water, and the mass concentration of solute is 5% -30%.
In the technical scheme, the molar ratio of the para-fluoro-m-phenoxy benzylidene dichloride to the solute in the aqueous solution of the alkali is 1:1.1-2.4.
Compared with the prior art, the invention has the following advantages:
according to the invention, an organic solvent is not required to be added in the chlorination process, the p-fluoro-m-phenoxy toluene is converted into an intermediate p-fluoro-m-phenoxy benzylidene dichloro in a high selectivity under the catalysis of a high-efficiency selective catalyst, the intermediate p-fluoro-m-phenoxy benzylidene dichloro is not required to be treated, p-fluoro-m-phenoxy benzaldehyde is obtained after direct hydrolysis, and refined fluoroether aldehyde is obtained after rectification. The method has the advantages of low safety and toxicity of the used materials, mild process conditions, high conversion rate and selectivity of the synthesized p-fluoro-m-phenoxy benzylidene dichloride, few byproducts, high total yield and content of products and low production cost, and is a clean and efficient production process.
Detailed Description
The following detailed description of the technical scheme of the present invention is provided, but the present invention is not limited to the following descriptions:
example 1:
a production process of fluoroether aldehyde comprises the following steps: 600kg of p-fluoro-m-phenoxy toluene and 12kg of azo-diisoheptonitrile are put into a 1000L reaction kettle with stirring, the temperature is raised to 40 ℃, 475kg of liquid chlorine is introduced for 8 hours, 0.1% of p-fluoro-m-phenoxy toluene, 95.9% of p-fluoro-m-phenoxy benzylidene dichloride, chlorinated impurities and 2.4% are controlled in the reaction, the obtained intermediate p-fluoro-m-phenoxy benzylidene dichloride is hydrolyzed by 3509kg of 10% potassium hydroxide aqueous solution for 2 hours at 110 ℃ to obtain crude fluoroether aldehyde, 587kg of refined fluoroether aldehyde is obtained after rectification, 98.6% is normalized, and the total yield of two steps is 91.1%.
Example 2:
a production process of fluoroether aldehyde comprises the following steps: 600kg of p-fluoro-m-phenoxy toluene and 6kg of azodiisobutyronitrile are put into a 1000L reaction kettle with stirring, the temperature is raised to 70 ℃ and 430kg of liquid chlorine is introduced for 5 hours, 1.8% of p-fluoro-m-phenoxy toluene, 94% of p-fluoro-m-phenoxy benzylidene dichloride, chlorinated impurities and 2.4% of p-fluoro-m-phenoxy benzylidene dichloride are controlled in the reaction, the obtained intermediate p-fluoro-m-phenoxy benzylidene dichloride is subjected to hydrolysis reaction at 100 ℃ for 3 hours by 3350kg of 8% sodium hydroxide aqueous solution to obtain crude fluoroether aldehyde, 579kg of refined fluoroether aldehyde is obtained after rectification, the normalized 98.1% is achieved, and the total yield of two steps is 89.4%.
Example 3:
a production process of fluoroether aldehyde comprises the following steps: 600kg of p-fluoro-m-phenoxy toluene, 3kg of dimethyl azodiisobutyrate and 440kg of liquid chlorine are introduced into a 1000L reaction kettle with stirring, 1.3% of p-fluoro-m-phenoxy toluene, 94.4% of p-fluoro-m-phenoxy benzylidene dichloro, chlorinated impurities and 2.8% of p-fluoro-m-phenoxy benzylidene dichloro are controlled in the reaction, the obtained intermediate p-fluoro-m-phenoxy benzylidene dichloro is subjected to hydrolysis reaction at 90 ℃ by 4385kg of 25% cesium carbonate aqueous solution for 4 hours to obtain crude fluoroether aldehyde, 582kg of refined fluoroether aldehyde is obtained after rectification, 98.2% is integrated, and the total yield of two steps is 90%.
Example 4:
a production process of fluoroether aldehyde comprises the following steps: 600kg of p-fluoro-m-phenoxy toluene, 9kg of dimethyl peroxydicarbonate, heating to 80 ℃ and introducing 452kg of liquid chlorine for 6 hours into a 1000L reaction kettle with stirring, controlling 0.5% of p-fluoro-m-phenoxy toluene, 95.3% of p-fluoro-m-phenoxy benzylidene dichloro, chlorinated impurities and 2.6% of p-fluoro-m-phenoxy benzylidene dichloro at 140 ℃ and carrying out hydrolysis reaction on 2605kg of 15% potassium carbonate aqueous solution for 1 hour to obtain crude fluoroether aldehyde, rectifying to obtain 584kg of refined fluoroether aldehyde, and returning to 98.3% and the total yield of two steps of 90.4%.
Example 5:
a production process of fluoroether aldehyde comprises the following steps: 600kg of p-fluoro-m-phenoxy toluene, 3kg of benzoyl peroxide and 3kg of cyclohexanone peroxide are put into a 1000L reaction kettle with stirring, the temperature is raised to 100 ℃, 460kg of liquid chlorine is introduced for 5 hours, 95.5% of p-fluoro-m-phenoxy benzylidene dichloride, 95.7% of chlorinated impurities and 2.7% of p-fluoro-m-phenoxy benzylidene dichloride are controlled in the reaction, the obtained intermediate p-fluoro-m-phenoxy benzylidene dichloride is hydrolyzed by 2255kg of 20% sodium carbonate aqueous solution for 2 hours at 120 ℃ to obtain crude fluoroether aldehyde, 586kg of refined fluoroether aldehyde is obtained after rectification, 98.5% is normalized, and the total yield of two steps is 90.9%.
The foregoing examples are merely illustrative of the technical concept and technical features of the present invention, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made according to the essence of the present invention should be included in the scope of the present invention.
Claims (8)
1. The production process of the p-fluoro-m-phenoxy benzaldehyde is characterized by comprising the following steps of:
adding a high-efficiency selective catalyst in the process of introducing chlorine into the para-fluoro-m-phenoxy toluene for chlorination reaction, and directly converting the para-fluoro-m-phenoxy toluene into para-fluoro-m-phenoxy benzylidene dichloride; the generated para-fluoro-meta-phenoxy benzylidene dichloride is subjected to hydrolysis reaction under alkaline conditions to generate para-fluoro-meta-phenoxy benzaldehyde; the chemical reaction formula is as follows:
2. the process according to claim 1, wherein the chlorination reaction is carried out at a reaction temperature of 40 to 120 ℃ for a reaction time of 2 to 10hr.
3. The production process according to claim 1, wherein the mass ratio of the p-fluorom-phenoxytoluene to the high-efficiency selective catalyst is 1:0.001-0.05.
4. The production process according to claim 1, wherein the high-efficiency selective catalyst is selected from any one, two or more of azobisisobutyronitrile, azobisisoheptonitrile, benzoyl peroxide, cyclohexanone peroxide, dimethyl azobisisobutyrate and dimethyl peroxydicarbonate.
5. The production process according to claim 1, wherein the mass ratio of p-fluorom-phenoxytoluene to chlorine is 1:0.68-0.8.
6. The process according to claim 1, wherein the hydrolysis reaction is carried out at a temperature of 80-160 ℃ for a time of 0.5-5hr.
7. The production process according to claim 1, wherein the alkaline condition is a condition formed by adding an aqueous alkali solution, the aqueous alkali solution is an aqueous solution formed by dissolving alkali such as potassium hydroxide, potassium carbonate, sodium hydroxide, sodium carbonate, cesium carbonate, hexamethylenetetramine and the like in water, and the mass concentration of the solute is 5% -30%.
8. The process according to claim 1, wherein the molar ratio of p-fluoro-m-phenoxy benzylidene dichloride to solute in aqueous alkali is 1:1.1-2.4.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111665905.7A CN116410070A (en) | 2021-12-31 | 2021-12-31 | Production process of p-fluoro-m-phenoxy benzaldehyde |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111665905.7A CN116410070A (en) | 2021-12-31 | 2021-12-31 | Production process of p-fluoro-m-phenoxy benzaldehyde |
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| CN116410070A true CN116410070A (en) | 2023-07-11 |
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| CN202111665905.7A Pending CN116410070A (en) | 2021-12-31 | 2021-12-31 | Production process of p-fluoro-m-phenoxy benzaldehyde |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56166142A (en) * | 1980-05-26 | 1981-12-21 | Nippon Oil & Fats Co Ltd | Preparation of m-phenoxybenzaldehyde |
| JPS56166131A (en) * | 1980-05-26 | 1981-12-21 | Nippon Oil & Fats Co Ltd | Preparation of mixture of m-phenoxybenzyl alcohol with m-phenoxybenzaldehyde |
| CN1244521A (en) * | 1999-08-18 | 2000-02-16 | 广东省化州市农药厂 | 3-bromo-4-fluoro methylbenzene process of cyhalofop-butyl production |
| CN102513148A (en) * | 2011-12-12 | 2012-06-27 | 南京工业大学 | Catalyst and process for coproduction of benzaldehyde and acyl chloride by benzal chloride acidolysis reaction |
| CN109796318A (en) * | 2019-01-22 | 2019-05-24 | 江苏佳麦化工有限公司 | A kind of synthesis technology of benzaldehyde |
| CN112707801A (en) * | 2020-12-30 | 2021-04-27 | 锦州三丰科技有限公司 | Preparation method of m-phenoxy benzaldehyde |
-
2021
- 2021-12-31 CN CN202111665905.7A patent/CN116410070A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56166142A (en) * | 1980-05-26 | 1981-12-21 | Nippon Oil & Fats Co Ltd | Preparation of m-phenoxybenzaldehyde |
| JPS56166131A (en) * | 1980-05-26 | 1981-12-21 | Nippon Oil & Fats Co Ltd | Preparation of mixture of m-phenoxybenzyl alcohol with m-phenoxybenzaldehyde |
| CN1244521A (en) * | 1999-08-18 | 2000-02-16 | 广东省化州市农药厂 | 3-bromo-4-fluoro methylbenzene process of cyhalofop-butyl production |
| CN102513148A (en) * | 2011-12-12 | 2012-06-27 | 南京工业大学 | Catalyst and process for coproduction of benzaldehyde and acyl chloride by benzal chloride acidolysis reaction |
| CN109796318A (en) * | 2019-01-22 | 2019-05-24 | 江苏佳麦化工有限公司 | A kind of synthesis technology of benzaldehyde |
| CN112707801A (en) * | 2020-12-30 | 2021-04-27 | 锦州三丰科技有限公司 | Preparation method of m-phenoxy benzaldehyde |
Non-Patent Citations (1)
| Title |
|---|
| 邹新琢等: "消旋反式菊酸α-氰基-4-氟-3-苯氧基苄酯合成", 应用化学, vol. 7, no. 2, 31 December 1990 (1990-12-31), pages 57 - 59 * |
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