3-Phenoxy-benzaldehyde
3-Phenoxybenzaldehyde
CAS: 39515-51-0
Molecular Formula: C13H10O2
3-Phenoxy-benzaldehyde - Names and Identifiers
| Name | 3-Phenoxybenzaldehyde |
| Synonyms | AKOS BBS-00003181 3-Phenoxybenzaldehyde 3-phenoxy-benzaldehyd 3-PHENOXYBENZALDEHYDE m-phenoxybenzaldehyde 3-phenoxy-benzaldehyde 3-Formyldiphenyl ether M-PHENOXY BENZALDEHYDE 3-FORMYLDIPHENYL ETHER Benzaldehyde,3-phenoxy- m-(phenyloxy)benzaldehyde m-Phenoxybenzaldehyde 3-Phenoxybenzaldehyde |
| CAS | 39515-51-0 |
| EINECS | 254-487-1 |
| InChI | InChI=1/C13H10O2/c14-10-11-5-4-8-13(9-11)15-12-6-2-1-3-7-12/h1-10H |
| InChIKey | MRLGCTNJRREZHZ-UHFFFAOYSA-N |
3-Phenoxy-benzaldehyde - Physico-chemical Properties
| Molecular Formula | C13H10O2 |
| Molar Mass | 198.22 |
| Density | 1.147g/mLat 25°C(lit.) |
| Melting Point | 13 °C |
| Boling Point | 169-169.5°C11mm Hg(lit.) |
| Flash Point | >230°F |
| Vapor Presure | 2.3E-06mmHg at 25°C |
| BRN | 511662 |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Sensitive | Air Sensitive |
| Refractive Index | n20/D 1.595(lit.) |
| Physical and Chemical Properties | Appearance: colorless or light yellow liquid |
| Use | It can be used as an intermediate of pyrethroid insecticides |
3-Phenoxy-benzaldehyde - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R26 - Very Toxic by inhalation |
| Safety Description | S23 - Do not breathe vapour. S24/25 - Avoid contact with skin and eyes. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S38 - In case of insufficient ventilation, wear suitable respiratory equipment. S28 - After contact with skin, wash immediately with plenty of soap-suds. |
| UN IDs | UN2810 - class 6.1 - PG 3 - EHS - Toxic, liquids, organic, n.o.s., HI: all |
| WGK Germany | 3 |
| RTECS | CU7560200 |
| TSCA | Yes |
| HS Code | 29124900 |
| Hazard Class | 6.1 |
| Packing Group | II |
| Toxicity | LD ipr-mus: >500 mg/kg JAFCAU26,954,78 |
3-Phenoxy-benzaldehyde - Nature
Open Data Verified Data
industrial product is dark brown oil. Boiling Point: 173~174 ℃(399Pa), 170~178 ℃(533Pa), melting point: 13~14 ℃, Flash point: 177 ℃. Refractive index 595, water-soluble 58mg/L(25 °c).
Last Update：2024-01-02 23:10:35
3-Phenoxy-benzaldehyde - Preparation Method
Open Data Verified Data
There are two main methods in industrialization: bromobenzaldehyde method and m-cresol method. Bromobenzaldehyde method has high cost, many impurities, and the purification of the product is difficult. At present, m-cresol route is adopted in China, that is, M-phenoxytoluene is first prepared by etherification, and then the final product is prepared by chlorination, hydrolysis, refining and other processes. The specific steps are:
- M-phenoxytoluene (MPT) was prepared by the reaction of m-cresol and halobenzene as raw materials under alkaline conditions.
- chlorination MPT is chlorinated to benzyl chloride and benzyl dichloride by the solvent method in the presence of an initiator:
- hydrolysis and chlorination of chlorinated liquid hydrolysis for MPA, there are two main hydrolysis methods: Mixed acid method with sulfuric acid and glacial acetic acid into 65% mixed acid. Dilute nitric acid method with 5%~ 10% of dilute nitric acid and oxidant, pressure of 2 ~ lOMPa
- at present, there are two main methods for refining and purifying MPA, namely, distillation method and chemical method.
Last Update：2022-01-01 10:42:29
3-Phenoxy-benzaldehyde - Use
Open Data Verified Data
This product can be used to synthesize a variety of pyrethroid pesticides, such as Deltamethrin, fenvalerate, cypermethrin, etc.
Last Update：2022-01-01 10:42:28
3-Phenoxy-benzaldehyde - Safety
Open Data Verified Data
- its gas forms an explosive mixture with air. In case of heat, spark is easy to burn. Combustion produces irritant, corrosive and/or toxic gases. Inhalation, ingestion and contact are harmful, and can be fatal in severe cases. Wear protective glasses, protective clothing and protective gloves.
- 200kg galvanized barrel packaging. Keep the container sealed and upright, and store in a cool, dry and ventilated environment.
Last Update：2022-01-01 10:42:29
3-Phenoxy-benzaldehyde - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | m-phenoxybenzaldehyde is an important intermediate of pyrethroid permethrin, cypermethrin, fenvalerate, fenpropathrin, fenfluvalerate, cyhalothrin, etc. can be used as an intermediate of pyrethroid insecticides mainly used to synthesize pyrethroid pesticides this product can be used to synthesize a variety of pyrethroid pesticides, such as deltamethrin, fenvalerate, cypermethrin, etc. |
| production method | there are two main industrialization methods: bromobenzaldehyde method and m-cresol method. The bromobenzaldehyde method has high cost, many impurities and difficult product purification. At present, the domestic use of m-cresol route, that is, through the etherification of the first to obtain m-phenoxy toluene, and then through the chlorination, hydrolysis, refining and other processes to produce the final product. The specific steps are:(1) the etherification of m-cresol and halogenated benzene as raw materials under alkaline conditions to produce m-phenoxy toluene (MPT). (2) Chlorination MPT is chlorinated in the presence of an initiator by solvent method to prepare benzyl chloride and benzyl dichloride. (3) Hydrolysis The chlorinated solution is hydrolyzed to MPA. There are mainly two hydrolysis methods: mixed acid method uses sulfuric acid and glacial acetic acid to prepare 65% mixed acid. The dilute nitric acid method uses 5%-10% dilute nitric acid and oxidant at a pressure of 2-10MPa. (4) There are currently two main methods for refining and purifying MPA, namely rectification and chemical methods. In addition, 3-phenoxytoluene is catalytically oxidized to produce 3-phenoxybenzoic acid, which is then electrolytically reduced to obtain phenoxybenzyl alcohol, and then 3-phenoxybenzaldehyde is selectively oxidized with sodium hypochlorite. There are two main methods for preparing m-phenoxybenzaldehyde in industry, namely bromobenzaldehyde method and m-phenoxytoluene method, which are described as follows. Benzene formaldehyde method Slowly add benzaldehyde to the dichloroethane in the presence of the catalyst aluminum trichloride, and then slowly add the dichloroethane solution of bromine containing chlorine, and after the reaction for a period of time, the post-treatment is carried out, and finally Distill to obtain m-bromobenzaldehyde. The catalyst cuprous chloride and solvent are added to the phenol potassium salt, and then m-bromobenzaldehyde is added dropwise. After heating and reacting for a period of time, post-treatment is carried out. The unreacted m-bromobenzaldehyde is recovered by distillation, and the distillation is continued. The 172~1 76 ℃/107.8 Pa fraction is collected as m-phenoxybenzaldehyde. This method is used in foreign countries for production. Due to technical and equipment problems in China, the cost is high and the purification is difficult. Production was stopped after a period of time. m-phenoxytoluene method m-phenoxytoluene is dissolved in benzene and first dehydrated, then the catalyst azobisisobutyronitrile is added, the temperature is increased to 80~84 ℃, chlorine gas is introduced for chlorination, and gas chromatography is used for intermediate control, Control in monochloride and dichloride, and then catch up with the remaining chlorine, distill and debenzene to obtain a mixture of m-phenoxybenzyl chloride and m-phenoxybenzyl dichloride, and then hydrolyze. The chloride hydrolysis of m-phenoxytoluene can be Sommlet by adding urotropine, glacial acetic acid, water and chloride of m-phenoxytoluene to the reaction kettle, heating to 103~108 ℃, heat preservation reaction for 7h, then post-treatment, adding toluene to extract m-phenoxybenzaldehyde, then removing toluene and m-phenoxybenzaldehyde for control. In addition, m-phenoxybenzaldehyde can also be prepared by alkaline hydrolysis oxidation. The m-phenoxytoluene chloride and 12% sodium carbonate aqueous solution are put into an autoclave for hydrolysis. The reaction temperature is 160 ℃, the pressure in the kettle is maintained at 0.7MPa, and the heat preservation reaction is carried out for 4 hours. During this period, the generated carbon dioxide is continuously removed to maintain the specified pressure. After the reaction is finished, the filtration is stratified. The oil layer is m-phenoxybenzyl alcohol and m-phenoxybenzaldehyde. The oil layer is further oxidized with 5% nitric acid, after the reaction is over, the layer is stratified, and the oil layer is crude m-phenoxybenzaldehyde. M-phenoxybenzaldehyde can be purified by rectification or chemical method (sodium metabisulfite). No matter which of the above methods is used, the obtained m-phenoxybenzaldehyde cannot meet the process requirements for preparing pyrethroid. For this reason, Jiangsu Chemical Pesticide Group has introduced a set of step-by-step crystallizer controlled by DCS from abroad to purify m-phenoxybenzaldehyde, which can reach a content of more than 99.5%. |
Last Update：2024-04-09 21:04:16
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