BENZENEAMINE
Aniline
CAS: 62-53-3
Molecular Formula: C6H7N
BENZENEAMINE - Names and Identifiers
| Name | Aniline |
| Synonyms | Anilin Aniline Anilina ai3-03053 Aminophen Benzamine C.I. 76000 Phenylamine BENZENAMINE amino-benzen Aminobenzene BENZENEAMINE anilin(czech) C.I. Oxidation Base |
| CAS | 62-53-3 |
| EINECS | 200-539-3 |
| InChI | InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 |
BENZENEAMINE - Physico-chemical Properties
| Molecular Formula | C6H7N |
| Molar Mass | 93.13 |
| Density | 1.022 g/mL at 25 °C (lit.) |
| Melting Point | -6 °C (lit.) |
| Boling Point | 184 °C (lit.) |
| Flash Point | 76 °C |
| Water Solubility | 36 g/L (20 ºC) |
| Solubility | water: soluble |
| Vapor Presure | 0.7 mm Hg ( 25 °C) |
| Vapor Density | 3.22 (185 °C, vs air) |
| Appearance | Liquid |
| Specific Gravity | 1.021 |
| Color | APHA: ≤250 |
| Odor | Sweet, amine-like odor detectable at 0.6 to 10 ppm |
| Exposure Limit | TLV-TWA skin 2 ppm (～8 mg/m3) (ACGIH),5 ppm (～19 mg/m3) (MSHA, OSHA, andNIOSH); IDLH 100 ppm (NIOSH). |
| Merck | 14,659 |
| BRN | 605631 |
| pKa | 4.63(at 25℃) |
| PH | 8.8 (36g/l, H2O, 20℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with oxidizing agents, bases, acids, iron and iron salts, zinc, aluminium. Light sensitive. Combustible. |
| Explosive Limit | 1.2-11%(V) |
| Refractive Index | n20/D 1.586(lit.) |
| Physical and Chemical Properties | Colorless oily flammable liquid with strong odor. Melting Point -6.3 ℃, boiling point 184 ℃,68.3 ℃(1.33kPa), relative density 1.0217(20/4 ℃), refractive index 1.5863, Flash Point (Open Cup) 70 ℃, spontaneous ignition point 770. In the open air or light will gradually turn brown. Can be volatilized with water vapor. Aniline can be miscible with ethanol, ether, chloroform and many other organic solvents. The solubility (weight percentage) of aniline in water is 3.7% at 30 °c, 4.2% at 50 °c, and 110 at 8.0% °c. There are alkaline, can be generated with hydrochloric acid hydrochloride, and sulfuric acid sulfate. |
| Use | Aniline is an important intermediate. The more important products produced by aniline were 300. There are about 80 aniline manufacturers in the world, with an annual total production capacity of more than 2.7 million t/a and an output of about 2.3 million t. The main consumption field is MDI, in 2000, its consumption accounted for about 84% of the total consumption of aniline. Aniline is mainly consumed in MDI, dye industry, rubber additives, pharmaceuticals, pesticides and organic intermediates. |
BENZENEAMINE - Risk and Safety
| Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R40 - Limited evidence of a carcinogenic effect R41 - Risk of serious damage to eyes R43 - May cause sensitization by skin contact R48/23/24/25 - R50 - Very Toxic to aquatic organisms R68 - Possible risk of irreversible effects R48/20/21/22 - R39/23/24/25 - R11 - Highly Flammable |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S27 - Take off immediately all contaminated clothing. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S46 - If swallowed, seek medical advice immediately and show this container or label. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S63 - S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. |
| UN IDs | UN 1547 6.1/PG 2 |
| WGK Germany | 2 |
| RTECS | BW6650000 |
| FLUKA BRAND F CODES | 8-9 |
| TSCA | Yes |
| HS Code | 2921 41 00 |
| Hazard Class | 6.1 |
| Packing Group | II |
| Toxicity | LD50 orally in rats: 0.44 g/kg (Jacobson) |
BENZENEAMINE - Upstream Downstream Industry
BENZENEAMINE - Nature
Open Data Verified Data
colorless or light yellow transparent liquid. Pure aniline is a colorless transparent liquid with special odor. 1g of the product can be dissolved in 28. 6mL water, 15.7ml boiling water, with ethanol, ether, benzene and other organic solvents miscible, with water vapor evaporation. The solubility of aniline in water increases with the increase of temperature. When the temperature is higher than 167 ^ 5 ℃, aniline and water can be dissolved in any proportion. The solubility of aniline in aniline salt is very large, and 50% of aniline hydrochloride can be miscible with aniline in any proportion. In the air oxygen, light irradiation or high temperature, aniline is easily oxidized.
Last Update：2024-01-02 23:10:35
BENZENEAMINE - Preparation Method
Open Data Verified Data
aniline is prepared by reduction of nitrobenzene with hydrogen in the presence of a catalyst.
Last Update：2022-01-01 09:25:51
BENZENEAMINE - Use
Open Data Verified Data
A standard sample for measuring the refractive index. Halogen, chromate, vanadate, nitrite and carboxylic acid were detected. For the pharmaceutical industry, organic synthesis.
Last Update：2022-01-01 09:25:52
BENZENEAMINE - Safety
Open Data Verified Data
The oral LD50 of rats was 440mg/kg. For absorption by intact skin. The percutaneous absorption rate of liquid aniline is about 1000 times faster than its vapor. Aniline can be through the respiratory tract, skin, eye contact or ingestion of human poisoning.
Last Update：2022-01-01 09:25:52
BENZENEAMINE - Reference Information
| Update Date: | 2022/11/14 7:31:25 |
| pH range of acid-base indicator discoloration | 8.1 |
| relative polarity | 0.42 |
| Henry's Law Constant | 1.91 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| (IARC) carcinogen classification | 2A (Vol. 27, Sup 7, 127) |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Product description | aniline is the simplest primary aromatic amine in which a hydrogen atom in the benzene molecule is substituted with an amino group, colorless oily flammable liquid with strong odor. The melting point is -6.3 ℃, the boiling point is 184 ℃, the relative density is 1.0217(20/4 ℃), the refractive index is 1.5863, the flash point (Open Cup) is 70 ℃, and the spontaneous ignition point is 770 ℃, heated to 370 ° C decomposition, slightly soluble in water, soluble in ethanol, ether, chloroform and other organic solvents. Brown when exposed to air or sunlight. Steam distillation can be used, and a small amount of zinc powder is added during distillation to prevent oxidation. 10 to 15ppm of NaBH4 can be added to the purified aniline to prevent oxidative deterioration. aniline solution is alkaline, and acid is easy to form salt. The hydrogen atom on the amino group may be substituted with a hydrocarbon group or an acyl group to produce secondary or tertiary aniline and acyl aniline. When the substitution reaction is carried out, ortho-and para-substitution products are mainly generated. The reaction with nitrous acid produces a diazonium salt, from which a series of benzene derivatives and azo compounds can be prepared. aniline is an important chemical raw material, the production of more important products up to 300 kinds, mainly used in MDI, dye industry, medicine, rubber vulcanization accelerator, such as sulfanilic acid in the dye industry, pharmaceutical industry of N-acetanilide. It is also a raw material for the manufacture of resins and coatings. In 2008the consumption of aniline was about 360,000 tons, and the demand is expected to be about 870,000 tons in 2012, The production capacity of commercial aniline reached 1.37 million tons, and the excess capacity was nearly 500,000 tons. Aniline on the blood and nerve toxicity is very strong, can be absorbed through the skin or respiratory tract caused by poisoning. aniline is mainly produced by two methods in industry: 1. Nitrobenzene is prepared by catalytic hydrogenation of active copper. This method can be used for continuous production and has no pollution. 2, chlorobenzene and ammonia are obtained by reaction at high temperature in the presence of copper oxide catalyst. |
| solubility in water (g/100ml) | grams dissolved per 100ml of water: 3.6g/20 ℃ |
| Study on domestic production process | in recent years, there are many studies on the reaction of benzene and H2O2 to aniline in China. In 2003, Xiamen Apex Technology Co., Ltd. developed a direct synthesis process of aniline from benzene, ammonia and oxygen. This process has the characteristics of high conversion rate of benzene and good selectivity. Aniline was synthesized from benzene with 25% ammonia and oxygen at 140~160 ℃ under 1.5MPa, the total selectivity of aniline is 94% (approximately 5% of phenol and 1% of benzene), aniline was synthesized from liquid ammonia and oxygen at 2.0 ~ 8.1MPa and 160~200 ℃, and the total selectivity was 95%. The catalysts used in this process are metal oxides, metal chlorides, metal fluorides, metal iodides, metal sulfates, metal phosphates, metal Heteropoly acid salts, BF3, metals other than iron powder, as well as mixtures of the above-listed compounds in any proportion, the carrier is at least one metal compound or non-metal compound selected from the group consisting of SiO2, B2O3, Al2O3, GeO2, TiO2, ZrO2, Nb2O5, Ta2O5, activated carbon, and the like. In 2004, the College of Chemistry, Sichuan University and the Key Laboratory of Green Chemistry and Technology of Sichuan province used H2O2 as an oxidant to synthesize aniline from benzene by direct oxidation and amination, and disclosed a patent for the preparation method. The researchers developed Ni-Zr-Ce/Al2O3 catalyst, at atmospheric pressure, 50 ℃ under mild conditions, the catalyst of benzene, ammonia and H2O2 direct oxidation of aniline has good activity, the selectivity of aniline is much higher than that of phenol. Increasing the ratio of ammonia to benzene in the reaction raw materials can improve the yield of aniline without increasing the amount of phenol. This method has low energy consumption and high atom utilization, and provides a new path for the green synthesis of aniline. One-step synthesis of aniline catalyst is γ-Al2O3 as the carrier, with nickel, molybdenum, vanadium, manganese, zirconium, cerium in 2 or 3 as the catalyst active component, obtained by a treatment such as roasting. In the one-step synthesis of aniline from the direct oxidation of benzene, the catalyst has high activity under mild reaction conditions, and the selectivity can reach 100%. |
| preparation of acetanilide | 1. Heating reaction of aniline with acetic acid catalyzed by sulfuric acid (Experimental Method: In a 50ml round bottom flask, place 10ml of freshly distilled aniline, 15ml of glacial acetic acid and a little zinc powder, install the fractionating column, insert the thermometer, reflux and heat for about 1H, and stir at the end of reaction, while hot, the reaction was poured into a 250ml cold water beaker, cooled and suction filtered, the crude product was washed, and the crude product was recrystallized and suction filtered.), General use of fractionation column to remove water to make the balance move to improve the yield: CH3COOH C6H5NH2 → CH3CONHC6H5 H2O2, acetyl chloride in aniline aminolysis (experimental method: in a dry test tube Dropwise adding aniline 5 drops, slowly add 8 drops of acetyl chloride, after the end of the reaction, add 5ml of water and stir with a glass rod (usually a tertiary amine is added to neutralize the acid produced): ch3coh5cl c6nh2 → CH3CONHC6H5 HCl3, acetic anhydride aminolysis in aniline (usually a tertiary amine is added to neutralize the acid produced):(CH3CO)O C6H5NH2 → CH3CONHC6H5 CH3COOH |
| Application | aniline is one of the most important intermediates in the dye industry, and is also the main raw material of medicine, rubber accelerator and antioxidant, can also be made of spices, varnishes and explosives. Aniline is used in the manufacture of dyes, pharmaceuticals, resins, varnishes, perfumes, vulcanized rubber and even solvents. Hazardous and harmful substances that affect the early life stages of marine animals. Environmental and food contaminants, Drinking Water Contaminants Candidate compound 3 (CCL3), according to the U. S. Environmental Protection Agency (EPA). aniline is an important raw material for the production of pesticides, aniline can be derived from N-alkyl aniline, alkyl aniline, O-nitroaniline, O-phenylenediamine, phenylhydrazine, cyclohexylamine, etc., can be used as a bactericide, seed dressing spirit, methyl sterilization Amine, sterilization Amine, carbendazim, carbendazim, benomyl, insecticide triazophos, pyridazine thiophos, quetiapine, herbicide alachlor, acetochlor, butachlor, cyclazinone, intermediate of imidazole quinolinic acid and the like. aniline is an important intermediate. The more important products produced by aniline were 300. There are about 80 aniline manufacturers in the world, with an annual total production capacity of more than 2.7 million t/a and an output of about 2.3 million t. The main consumption field is MDI, in 2000, its consumption accounted for about 84% of the total consumption of aniline. Aniline is mainly consumed in MDI, dye industry, rubber additives, pharmaceuticals, pesticides and organic intermediates. In 2000, the consumption of aniline was 185,000 t, which was insufficient and needed to be solved by import. Aniline series intermediates and dye products are: 2, 6-diethylaniline N-acetanilide, P-butylaniline, O-phenylenediamine, diphenylamine, diazoaminobenzene, 4,4 '-diaminotriphenylmethane, 4,4'-diaminodiphenylcyclohexylmethane, N,N-dimethylaniline, N-ethylaniline, N,N-diethylaniline, N,N-dipropylaniline, P-acetamidophenol, P-aminoacetophenone, 4,4 '-diethylaminobenzophenone, 4-(p-aminobenzene) butyric acid, P-nitroaniline, N-nitrosodiphenylamine, β-acetanilide, 1, 4-diphenylsemicarbazide, 2-phenylindole, P-phenylaminoaniline, N-formyl aniline, N-benzoyl aniline, N-acetanilide, 2,4, 6-trichloroaniline, P-iodoaniline, 1-aniline-3-methyl-5-pyrazolone, hydroquinone, dicyclohexylamine, 2-(N-methylanilino) propionitrile, 3-(N-ethylanilino) Propionitrile, 2-(N-ethylanilino) ethanol, P-aminoazobenzene, phenylhydrazine, monophenylurea, biphenylurea, P-thiocyanatoaniline, 4,4 '-diphenylmethane diisocyanate, polyphenylmethylene polyisocyanate, 4-aminoacetanilide, N-methyl-N-(β-hydroxyethyl) aniline, N-methyl-N(β-chloroethyl) aniline, N-dimethyl-p-phenylenediamine, N,N,N',N'-tetramethyl-p-phenylenediamine, N,N-diethyl-p-phenylenediamine, 4,4'-methylenebis (N,N-diethylaniline, phenylthiourea, diphenylthiourea, P-aminobenzenesulfonic acid, 4,4 '-diaminodiphenylmethane benzoquinone, N,N-diethanolaniline, acetanilide, p-aminophenol, N-ethylbenzylaniline, N-methylformylaniline, N-methylacetanilide, P-bromoacetanilide, bis (p-aminocyclohexyl) methane, phenylhydrazone diphenylcarbazone, acetophenone phenylhydrazone, aniline -2, 4-disulfonic acid, P-aminoazobenzene -4' sulfonic acid, phenylhydrazine -4-sulfonic acid, thioacetanilide, 2-methylindole, 2, 3-dimethylindole, N-methyl -2-phenyl indole used as analytical reagent, also used in the synthesis of dyes, resins, pseudo-paint and perfume used as weak base, can be in the form of hydroxide Easily hydrolyzable salts of trivalent and tetravalent elements (Fe3 +, Al3 +, Cr3 +) are precipitated to separate salts from the poorly hydrolyzable divalent element (Mn2 +). In microcrystallite analysis, to test for the formation of thiocyanate complex anions or other anions (These anions can be precipitated by aniline) elements (Cu, Mg, Ni, Co, Zn, Cd, Mo, W, V). Halogen, chromate, vanadate, nitrite and carboxylic acid were examined. Solvent. Organic Synthesis, dye manufacturing |
| production method | the industrial production methods of aniline mainly include the reduction method of nitrobenzene iron powder, the amination method of chlorinated benzene, nitrobenzene catalytic hydrogenation reduction method and phenol ammonia solution method. Due to the high cost, equipment corrosion and other reasons, the ammonium chloride method has been completely stopped in foreign countries. Nitrobenzene hydrogenation reduction method is the main production method at home and abroad. a small number of foreign companies such as Japan's myocardial Petrochemical Company (30,000 t/a unit) and the United States Iron and Steel Chemical Company (90,000 t/a unit) also use phenol ammoniation process. In addition, the traditional iron powder reduction method, such as Bayer company of Germany and Mobel company of the United States, uses by-produced iron oxide and iron-based raw materials, thus making the overall economic benefit superior to that of the hydrogenation method. 1. Iron powder reduction method nitrobenzene is reduced with iron powder, the reaction liquid is neutralized with lime, washed, and then distilled to obtain the finished product. 2. Hydrogenation reduction method in the presence of copper catalyst, nitrobenzene is hydrogenated and reduced in the gas phase in a fluidized bed reactor to obtain crude aniline. After condensation and stratification, the reaction solution is subjected to vacuum distillation to obtain a finished product. aniline is currently produced by catalytic hydrogenation of nitrobenzene. The commonly used catalyst is Cu-SiO2, and the catalyst has good selectivity, can smoothly reduce nitrobenzene to aniline, and is not easy to produce hydrogenation on benzene core. The reaction is carried out in a fluidized bed reactor. After purification, the hydrogen is heated to 350~400 ℃ by a heater and then enters the evaporator. At the same time, nitrobenzene enters the evaporator from a high level tank and is contacted with hot hydrogen for gasification, and overheat to 180~223 ℃, The mixed gas enters from the bottom of the fluidized bed and reacts with the copper catalyst supported on silica gel in the fluidized bed, and the crude aniline and water vapor generated are discharged from the top of the bed. The crude aniline is cooled by a condenser, separated, and then subjected to rectification to obtain the finished aniline. Now the production of aniline has been achieved in a continuous manner, and the reduction reaction is carried out under the condition of boiling reflux at atmospheric pressure, realizing the large-scale production of small equipment. |
| category | toxic substances |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 250 mg/kg; Oral-mouse LD50: 464 mg/kg |
| stimulation data | Skin-rabbits 20 mg/24 h moderate; eye-rabbit 20 mg/24 h moderate |
| explosive hazard characteristics | explosive when mixed with air; Reaction with oxidant |
| flammability hazard characteristics | open flame, high temperature, strong oxidant flammable; hyperthermic decomposition of toxic nitrogen oxide gases |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from oxidants and food additives |
| fire extinguishing agent | foam, carbon dioxide, dry powder |
| Occupational Standard | TLV-TWA 2 PPM; TWA 5 PPM (19 mg/m3); sel 20 mg/m3 |
| spontaneous combustion temperature | 615°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-and health-threatening concentration | 100 ppm |
Last Update：2024-06-05 11:50:41
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View History
Raw Materials for BENZENEAMINE
Downstream Products for BENZENEAMINE
Methylene diphenyl diisocyanate
N-Ethylaniline
2,4,6-Trichloroaniline
Cyclohexylamine
Phenylhydrazinesulfate
Dicyclohexylamine
2,6-Diethylaniline
N-Ethylaniline
2,4,6-Trichloroaniline
Cyclohexylamine
Phenylhydrazinesulfate
Dicyclohexylamine
2,6-Diethylaniline