N-乙酰苯胺
N-Acetylaniline
CAS: 103-84-4
Molecular Formula: C8H9NO
N-乙酰苯胺 - Names and Identifiers
| Name | N-Acetylaniline |
| Synonyms | ACETANIL Antifebrin ACETANILIDE Acetanilide 'LGC' (4002) 'LGC' (2605) ACETYLANILINE N-Acetylaniline N-Phenylacetamide AKOS BBS-00004291 ACETYLAMINOBENZENE ACETIC ACID ANILIDE N-(4-fluorophenyl)acetamide Acetanilide,(N-Phenylacetamide) |
| CAS | 103-84-4 |
| EINECS | 203-150-7 |
| InChI | InChI:1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) |
N-乙酰苯胺 - Physico-chemical Properties
| Molecular Formula | C8H9NO |
| Molar Mass | 135.16 |
| Density | 1,121 g/cm3 |
| Melting Point | 113-115°C(lit.) |
| Boling Point | 304°C(lit.) |
| Flash Point | 173 °C |
| Water Solubility | 5 g/L (25 ºC) |
| Solubility | Slightly soluble in water; very soluble in ethanol and acetone; soluble in ethyl ether. |
| Vapor Presure | 1 mm Hg ( 114 °C) |
| Vapor Density | 4.65 (vs air) |
| Appearance | Powder |
| Color | Off-white to beige to grayish-blue |
| Merck | 14,50 |
| BRN | 606468 |
| pKa | 0.5(at 25℃) |
| PH | 5-7 (10g/l, H2O, 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, caustics, alkalies. |
| Refractive Index | 1.5700 (estimate) |
| Physical and Chemical Properties | Character white lustrous Flake crystal or white crystalline powder. Odorless. melting point 114.3 ℃ boiling point 304 ℃ relative density 1.2190 flash point 173.9 ℃ solubility slightly soluble in cold water, soluble in hot water, methanol, ethanol, ether, chloroform, acetone, glycerol and benzene. |
| Use | Sulfonamides, rubber vulcanization accelerator, dyes and synthetic camphor and other raw materials and intermediates, cosmetics industry hydrogen peroxide stabilizer |
N-乙酰苯胺 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 1 |
| RTECS | AD7350000 |
| TSCA | Yes |
| HS Code | 29242995 |
| Toxicity | LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger) |
N-乙酰苯胺 - Nature
Open Data Verified Data
white glossy Flake crystal or white crystalline powder. Slight odor of aniline and acetic acid. mp 113~115 ℃; bp 304 ~ 305aC; d15 1. 219; pK(28 ℃)13.0. lg the product is soluble in water 18 5mL, boiling water 20mL, ethanol 3.4mL, methanol 3mL, boiling ethanol 0. 6mL, ether 18mL, chloroform 3.7mL, acetone 4mL, 5mL glycerol and 47mL benzene. The alkalinity is very weak. When acid or alkaline aqueous solution is easy to decompose into aniline and acetic acid. Flammable. In case of high heat, open flame or contact with oxidant, there is a risk of combustion. Combustion decomposition, release of toxic nitrogen oxides.
Last Update：2024-01-02 23:10:35
N-乙酰苯胺 - Preparation Method
Open Data Verified Data
aniline and glacial acetic acid were placed in the reactor and refluxed until free aniline was absent. After completion of the reaction, the residue was removed by hot filtration. The filtrate was cooled, crystallized, centrifuged, washed with water and dried to obtain the product.
Last Update：2022-01-01 09:27:03
N-乙酰苯胺 - Use
Open Data Verified Data
This product is commonly used in the raw materials of sulfonamides, but also for dyes, rubber vulcanization accelerator and synthetic camphor.
Last Update：2022-01-01 09:27:03
N-乙酰苯胺 - Safety
Open Data Verified Data
rat oral LD50: 800mg/kg; Mouse oral LD50: 1210mg/kg. Inhalation of the product on the upper respiratory tract irritation. High dose intake can cause methemoglobinemia and bone marrow hyperplasia. Staff should be protected. Store in a cool, ventilated warehouse. Keep away from fire and heat source. Protection from direct sunlight. Keep the container sealed. Should be stored separately from the oxidant, alkali.
Last Update：2022-01-01 09:27:04
N-乙酰苯胺 - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | used as a stabilizer for analytical reagents and hydrogen peroxide, and also used in the pharmaceutical industry acetanilide is the raw material of sulfonamides and can be used as analgesics, antipyretics and preservatives. Used to make dye intermediates p-nitroacetanilide, p-nitroaniline and p-phenylenediamine. During the Second World War, it was used in large quantities to make acetaminobenzenesulfonyl chloride (Acetylsulfanilylchloride). Acetanilide is also used to make thioacetamide. In industry, it can be used as rubber vulcanization accelerator, stabilizer of fiber grease coating, stabilizer of hydrogen peroxide, and synthetic camphor. It is the raw materials and intermediates of sulfonamides, rubber vulcanization accelerators, dyes and synthetic camphor. Hydrogen peroxide stabilizer for cosmetics industry Test cerium, chromium, iron, ferrocyanide, lead, Manganese, chlorinating agent, nitrate. Stabilizer of hydrogen peroxide solution, organic microanalysis, standard for determination of nitrogen. Acetanilide is also the raw material of sulfonamides. |
| production method | is obtained by acetylation of aniline with acetic acid. Aniline and glacial acetic acid (excess 100%) were placed in a jacketed glass-lined reactor and refluxed for 6-14h until there was no free aniline. If dilute acetic acid is used, the reaction temperature is 150-160 ℃. After the reaction, filter while hot to remove the residue, cool and crystallize the filtrate, filter by centrifugation, wash with water and dry to obtain the product. It is also possible to use acetic anhydride as an acylating agent, and the reaction is carried out in a benzene solution, and the acetic anhydride is 150% in excess. Operation Example 1 Four reaction tanks are arranged in a trapezoid, with the highest one equipped with a fractionation column. Aniline is added continuously from the top of the fractionation column, the mixture of recovered acetic acid and aniline is added continuously from the second reaction tank, and acetic acid is added continuously from the third reaction tank. Control different reaction temperatures (the third is 160-170 ℃, the fourth is 200-210 ℃), so that acetic acid and aniline undergo gas-liquid convection reaction, and the water generated by the reaction is evaporated from the top of the fractionation column, The acetylation stream is fed into the fourth reaction tank, and then pumped into the distillation tank, and the unconverted aniline and acetic acid are evaporated under reduced pressure. The reaction product is cooled into flakes to obtain acetanilide. Weight ratio: aniline: acetic acid = 1:(0.65-0.70), 99.5% yield. Operation Example 2: First, aniline and 3/10 amount of acetic acid (with a content of more than 60%) are added to the acylation pot, heated, and at the same time, 1/10 amount of acetic acid is slowly added, heated to boiling, the fractional dilute acetic acid is collected, and 4/10 amount of concentrated acetic acid or glacial acetic acid is slowly added to the pot, and the reaction is 7 hours. The last time to add the remaining 2/10 amount of glacial acetic acid, reflux fractionation, when the concentration of fractionated acetic acid reaches more than 85%, vacuum distillation, distillation of the remaining acetic acid. Discharge, cooling and crushing are finished products. Most of the production of acetanilide by aniline acylation uses glacial acetic acid as an acylating agent. Raw material consumption quota: aniline (99%)690kg/t, glacial acetic acid 500kg/t. Laboratory preparation can be done by the following method: 20.5g(0.22mol) aniline, 21.5g(0.21mol) acetic anhydride, 21g(0.35mol) glacial acetic acid and 0.1g zinc powder are added into a 500ml flask with reflux condenser. After mixing, slowly heat and boil for half an hour. Then the hot reactants are poured into 500ml of cold water in a fine flow, stirred, and cooled. Filter and dry to obtain 26g of coarse product. Melting point 113 ℃. Recrystallization and purification with ethanol and water, melting point 114 ℃. |
| category | combustible items |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 800 mg/kg; Oral-mouse LD50: 1210 mg/kg |
| flammability hazard characteristics | combustible in case of open flame, high temperature and strong oxidant; combustion decomposition releases toxic nitrogen oxide smoke |
| storage and transportation characteristics | complete packaging, light loading and unloading; warehouse ventilation, away from open flames, high temperature, separate storage from oxidant |
| fire extinguishing agent | foam, dry powder, carbon dioxide, mist water, sand |
| spontaneous combustion temperature | 540°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:05
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