aniline

[běn àn]

Organic compound

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This entry is made by Compilation and application of scientific encyclopedia entries of "Science Popularization China" to examine.

Aniline, also known as aminobenzene, is an organic compound with the chemical formula C six H seven N， It is a colorless oily liquid, which is heated to 370 ℃ to decompose, slightly soluble in water, and easily soluble in ethanol, ether and other organic solvents.

Aniline is one of the most important amine substances. It is mainly used for manufacturing dyes, drugs, resins, and also can be used as rubber vulcanization accelerator. It can also be used as a black dye. Its derivative methyl orange can be used as an indicator for acid-base titration.

On October 27, 2017, the list of carcinogens published by the International Agency for Research on Cancer of the World Health Organization (WHO) was preliminarily collated and referenced, and aniline was included in the list of three types of carcinogens.^[2]

Chinese name: aniline
Foreign name: Aniline
Alias: Aminobenzene
chemical formula: C six H seven N
molecular weight: ninety-three point one two seven
CAS login number: 62-53-3
EINECS login number: 200-539-3
Melting point: -6.2 ℃

Boiling point: 184 ℃
Water solubility: Slightly soluble
Density: 1.022 g/cm³
Appearance: Colorless to light yellow transparent liquid
Flash point: 76 ℃
Security description: S26；S27；S36/37/39；S45；S46；S61；S63
Hazard symbol: T
Hazard description: R40；R41；R43；R48/23/24/25；R50；R68
UN dangerous goods number: one thousand five hundred and forty-seven

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Physical and chemical properties

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Density: 1.022g/cm three

Melting point: - 6.2 ℃

Boiling point: 184 ℃

Flash point: 76 ℃

Refractive index: 1.586 (20 ℃)

Saturated vapor pressure: 2.00kPa (77 ℃)^[3]

Critical temperature: 425.6 ℃

Critical pressure: 5.30MPa

Ignition temperature: 615 ℃

Upper explosive limit（ V /V）：11.0%

Lower explosive limit（ V /V）：1.2%

Appearance: colorless to light yellow transparent liquid

Solubility: slightly soluble in water, soluble in ethanol, ether, benzene^[1]

conjugated structure

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N in aniline is almost sp two Hybridization (actually sp three Hybridization), the orbital occupied by the lone pair of electrons can be conjugated with the benzene ring, and the electron cloud can be dispersed on the benzene ring, reducing the density of the electron cloud around nitrogen.

Aniline structural formula

Molecular structure data

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Molar refractive index: 30.48

Molar volume (cm three /mol）：91.7

Isotonic specific volume (90.2K): 233.1

Surface tension (dyne/cm): 41.7

Polarization (10 -24 cm three ）：12.08^[1]

Calculate chemical data

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Reference value for drainage parameter calculation (XlogP): None

Number of hydrogen bond donors: 1

Number of hydrogen bond receptors: 1

Number of rotatable chemical bonds: 0

Number of tautomers: 0

Topological molecular polar surface area: 26

Number of heavy atoms: 7

Surface charge: 0

Complexity: 46.1

Number of isotope atoms: 0

Determine the number of atomic structure centers: 0

Number of uncertain atomic structure centers: 0

Determine the number of chemical bond structure centers: 0

Number of uncertain chemical bond structure centers: 0

Number of covalent bond units: 1^[1]

toxicology data

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1. Acute toxicity

LD fifty : 250mg/kg (rat oral); 1400mg/kg (rat percutaneous); 1000mg/kg (rabbit mouth); 820mg/kg (rabbit percutaneous).

LC fifty ：665mg/m three (mice inhaled, 7h).

2. Irritation

Rabbit percutaneous: 500mg (24h), moderate irritation.

Rabbit eyes: 20mg (24h), moderate irritation.

3. Subacute and chronic toxicity

Rats inhaled 19mg/m three Methemoglobin increased to 600mg/mL at week 23 and 6h every day.

4. Mutagenicity

Microbial mutagenesis: Salmonella typhimurium 100 μ g/plate.

Sister chromatid exchange: 210mg/kg in the abdominal cavity of mice.

Micronucleus test: mice were given 50mg/kg intraperitoneally.

DNA damage: 1g/kg by mouth in mice.

5. Carcinogenicity

IARC carcinogenicity review: G3, insufficient evidence of carcinogenicity to humans and animals.^[1]

Ecological data

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1. Ecotoxicity

LC one hundred : 21.5mmol/L (24h) (Tetrahymena pyriformis).

LC fifty : 51~92mg/L (48h); 8.2mg/L (7d) (rainbow trout).

EC fifty : 0.1~0.65mg/L (48h) (Daphnia).

2. Biodegradability

At low concentration, 40%~60% can be degraded in natural water within one day; It can degrade 75%~99% within 21 days.

3. Non biodegradable

Half life in air 3.3h (theoretical).^[1]

purpose

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Aniline is one of the most important intermediates in the dye industry, which can be used to produce acid ink blue G, acid mordant BS, acid light yellow, direct orange S, direct pink, indigo, disperse yellow brown, cationic pink FG, reactive brilliant red X-SB, etc; In the aspect of organic pigments, it is used to manufacture golden red, golden red g, scarlet powder, phenol cyanine red, oil soluble black, etc. In the printing and dyeing industry for the dye aniline black; In the pesticide industry, it is used to produce many pesticides and fungicides, such as DDV, herbicide, mefenacet, etc; Aniline is an important raw material for rubber additives, which is used to manufacture antioxidant A, antioxidant D, antioxidant RD, antioxidant 4010, accelerator M, 808, D, CA, etc; It can also be used as the raw material of pharmaceutical sulfonamides, as well as the intermediate for the production of spices, plastics, varnish, films, etc; It can also be used as stabilizer in explosives, explosion-proof agent in gasoline and solvent; It can also be used to produce hydroquinone, 2-phenylindole, etc.

Aniline is an important raw material for pesticide production, which can be derived from aniline N -Alkyl aniline, alkyl aniline, o-nitroaniline, cyclohexylamine, etc., can be used as intermediates of fungicides such as sodium dichloride, seed dressing, pesticides triazophos, pyridazinon, quinthion, herbicides such as alachlor, cyclozinone, imidazolidinoic acid, etc.

Poisoning performance

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Acute poisoning

It mainly causes methemoglobinemia and liver, kidney and skin damage.

Those who absorb or inhale a large amount of aniline in a short period of time will first develop methemoglobinemia, which is characterized by cyanosis, and the tongue, lips, finger (toe) nails, cheeks, and auricles are blue brown. In severe cases, the skin and mucosa are lead gray, and there are dizziness, headache, fatigue, chest tightness, palpitations, shortness of breath, anorexia, nausea, vomiting, and even disturbance of consciousness. The methemoglobin is more than 10%, and Hernz bodies appear in red blood cells. Hemolytic anemia may occur about 4 days after poisoning. Toxic liver disease occurs within 2-7 days after poisoning. In addition to the above symptoms, the symptoms of gastrointestinal irritation are obvious.

Eye contact: conjunctival keratitis may occur.

Skin contact: may cause dermatitis.

Manifestations of chronic poisoning

Long term low concentration exposure may cause toxic liver disease.

Health hazard: This product mainly causes methemoglobinemia, hemolytic anemia and liver and kidney damage. Easily absorbed through the skin. Acute poisoning: the patient has cyanosis on the lips, fingertips and auricles, headache, dizziness, nausea, vomiting, numbness of fingers, and trance; In case of severe poisoning, the skin and mucous membrane are severely cyanotic, with dyspnea, convulsions, even coma and shock. Hemolytic jaundice, toxic hepatitis and renal damage occur. There may be chemical cystitis. Eye contact causes conjunctival keratitis. Chronic poisoning: the patient has neurasthenic syndrome, accompanied by mild cyanosis, anemia, and hepatosplenomegaly. Skin contact can cause eczema.

First aid measures

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Skin contact: Take off contaminated clothes immediately, and wash skin thoroughly with soapy water and clean water. Get medical attention.

Eye contact: immediately lift the eyelid, and thoroughly flush it with a large amount of flowing water or physiological saline for at least 15 minutes. Get medical attention.

Inhalation: quickly leave the site to a place with fresh air. Keep the respiratory tract unobstructed. If breathing is difficult, give oxygen. If breathing stops, perform artificial respiration immediately. Get medical attention.

Ingestion: drink enough warm water to induce vomiting. Get medical attention.

Fire fighting measures

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Hazardous combustion products: carbon monoxide, nitrogen oxides.

Extinguishing method: firefighters must wear gas masks and extinguish the fire upwind from a safe distance.

Extinguishing agent: water, foam, carbon dioxide, sand.

Leakage emergency treatment

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Evacuate the personnel in the leakage contaminated area to a safe area quickly, isolate them, and strictly restrict access. Cut off the ignition source. It is recommended that emergency personnel wear self-contained positive pressure respirators and anti poison clothing. Do not touch the leakage directly. Cut off the leakage source as much as possible. Prevent from flowing into restricted spaces such as sewers and flood discharge ditches.

Small amount of leakage: absorb or absorb with sand or other incombustible materials.

Large amount of leakage: build a dike or dig a pit to receive. Spray water or foam is used to cool and dilute steam and protect on-site personnel. Transfer to tank car or special collector with pump, and recycle or transport to waste disposal site for disposal.

Handling storage

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Precautions for operation: closed operation, providing sufficient local ventilation. The operation shall be mechanized and automated as far as possible. Operators must be specially trained and strictly abide by the operating procedures. It is recommended that operators wear filter type gas masks (half masks), safety goggles, anti poison penetration work clothes and rubber oil resistant gloves. Keep away from kindling and heat sources, and smoking is strictly prohibited in the workplace. Use explosion-proof ventilation systems and equipment. Prevent vapor leakage into the air of the workplace. Avoid contact with oxidants and acids. Load and unload gently during transportation to prevent damage to packaging and containers. Fire fighting equipment and leakage emergency treatment equipment of corresponding types and quantities shall be provided. Empty containers may leave harmful substances.

Precautions for storage: store in a cool and ventilated warehouse. Keep away from kindling and heat sources. The storage temperature shall not exceed 30 ℃, and the relative humidity shall not exceed 80%. Keep away from light. The package shall be sealed and shall not contact with air. It shall be stored separately from oxidants, acids and edible chemicals, and mixed storage is strictly prohibited. Equip with corresponding types and quantities of fire-fighting equipment. The storage area shall be equipped with leakage emergency treatment equipment and appropriate materials.

security information

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Safety terminology

S26：In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

After eye contact, immediately flush with plenty of water and seek medical advice.

S27：Take off immediately all contaminated clothing.

Take off all contaminated clothes immediately.

S36/37/39：Wear suitable protective clothing, gloves and eye/face protection.

Wear appropriate protective clothing, gloves and eye/face protection.

S45：In case of accident or if you feel unwell, seek medical advice immediately (show the lable where possible).

In case of an accident or feeling unwell, seek medical advice immediately (show the label if possible).

S46：If swallowed, seek medical advice immediately and show this container or label.

If ingested, seek medical advice immediately and show the container/label.

S61：Avoid release to the environment. Refer to special instructions/Safety data sheets.

Avoid releasing into the environment, refer to special instructions/safety receipt instructions.

S63：There may be a risk of harm to the fetus.

There may be danger of harm to the fetus.

Risk terminology

R40：Possible risks of irreversible effects.

There may be risk of irreversible effects.

R41：Risk of serious damage to eyes.

Risk of serious damage to eyes.

R43：May cause sensitization by skin contact.

Skin contact may cause irritation.

R48/23/24/25：Toxic : danger of serious damage to health by prolonged exposure through inh.,in contact with skin and if swallowed

Toxic: danger of serious damage to health through long-term exposure through inhalation, skin and ingestion.

R50：Very toxic to aquatic organisms.

Very toxic to aquatic organisms.

R68：Possible risk of irreversible effects.

There may be danger of irreversible consequences.

Substance toxicity

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Toxicity test data
number	Toxicity type	test method	Test object	Dosage	Toxic effect
one	acute toxicity	Oral	children	3125 mg/kg	Lung, chest or respiratory toxicity - cyanosis
two	acute toxicity	Not reported	Adult male	350 mg/kg	No values other than lethal dose were reported for detailed effects
three	acute toxicity	Not reported	Adult male	150 mg/kg	No values other than lethal dose were reported for detailed effects
four	acute toxicity	Oral	Rat	250 mg/kg	No values other than lethal dose were reported for detailed effects
five	acute toxicity	inhalation	Rat	250 ppm/4H	No values other than lethal dose were reported for detailed effects
six	acute toxicity	skin surface	Rat	1400 mg/kg	No values other than lethal dose were reported for detailed effects
seven	acute toxicity	intraperitoneal injection	Rat	420 mg/kg	No values other than lethal dose were reported for detailed effects
eight	acute toxicity	Oral	mice	464 mg/kg	No values other than lethal dose were reported for detailed effects
nine	acute toxicity	inhalation	mice	175 ppm/7H	No values other than lethal dose were reported for detailed effects
ten	acute toxicity	intraperitoneal injection	mice	492 mg/kg	No values other than lethal dose were reported for detailed effects
eleven	acute toxicity	subcutaneous injection	mice	200 mg/kg	No values other than lethal dose were reported for detailed effects
twelve	acute toxicity	Oral	dog	195 mg/kg	No values other than lethal dose were reported for detailed effects
thirteen	acute toxicity	skin surface	dog	1540 mg/kg	No values other than lethal dose were reported for detailed effects
fourteen	acute toxicity	intravenous injection	dog	200 mg/kg	No values other than lethal dose were reported for detailed effects
fifteen	acute toxicity	Oral	cat	100 mg/kg	No values other than lethal dose were reported for detailed effects
sixteen	acute toxicity	inhalation	cat	180 ppm/8H	No values other than lethal dose were reported for detailed effects
seventeen	acute toxicity	skin surface	cat	254 mg/kg	No values other than lethal dose were reported for detailed effects
eighteen	acute toxicity	subcutaneous injection	cat	100 mg/kg	No values other than lethal dose were reported for detailed effects
nineteen	acute toxicity	Oral	rabbit	500 mg/kg	No values other than lethal dose were reported for detailed effects
twenty	acute toxicity	skin surface	rabbit	820 μL/kg	No values other than lethal dose were reported for detailed effects
twenty-one	acute toxicity	subcutaneous injection	rabbit	1 mg/kg	Lung, chest or respiratory toxicity - other changes
twenty-two	acute toxicity	intravenous injection	rabbit	64 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-three	acute toxicity	Oral	guinea pig	400 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-four	acute toxicity	skin surface	guinea pig	1290 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-five	acute toxicity	intraperitoneal injection	guinea pig	100 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-six	acute toxicity	Oral	quail	750 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-seven	acute toxicity	Oral	mammal	500 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-eight	acute toxicity	inhalation	mammal	2500 mg/m three	No values other than lethal dose were reported for detailed effects
twenty-nine	acute toxicity	Oral	Wild birds	562 mg/kg	No values other than lethal dose were reported for detailed effects
thirty	Chronic toxicity	Oral	Rat	913 mg/kg/2W-I	Endocrine toxicity - changes in spleen weight Nutritional and metabolic system toxicity - changes in iron content Biochemical toxicity - inhibiting transaminase activity and changing the spatial structure of transaminase
thirty-one	Chronic toxicity	Oral	Rat	550 mg/kg/5D-C	Hemotoxicity - spleen changes Nutrition and metabolic system toxicity - weight loss or weight gain rate decrease Chronic disease related toxicity - death
thirty-two	Chronic toxicity	Oral	Rat	210 mg/kg/12W-C	Blood toxicity - abnormal staining of red blood cells or affecting nucleated red blood cells Hemotoxicity - Methemoglobin, carboxyhemoglobin Biochemical toxicity - inhibition or induction of esterase
thirty-three	Chronic toxicity	inhalation	Rat	3 mg/m three /22W-I	Hemotoxicity - changes in serum composition (such as TP, bilirubin, cholesterol) Blood toxicity - other changes
thirty-four	Chronic toxicity	inhalation	Rat	87 ppm/6H/2W-I	Hepatotoxicity - changes in liver weight Endocrine toxicity - changes in spleen weight Blood toxicity - red blood cell count changes
thirty-five	Chronic toxicity	inhalation	Rat	300 μg/m three /24H/80D-C	Behavioral toxicity - muscle contraction or spasm
thirty-six	Chronic toxicity	inhalation	Rat	5 mg/m three /24H/21D-C	Hemotoxicity - Methemoglobin, carboxyhemoglobin
thirty-seven	Chronic toxicity	subcutaneous injection	Rat	900 mg/kg/6D-I	Hepatotoxicity - other changes Biochemical toxicity - inhibition or induction of liver microsomal mixed functional oxidase (dealkylation, hydroxylation, etc.) Biochemical toxicity - inhibition or dehydrogenase induction
thirty-eight	Eye toxicity	skin surface	rabbit	20 mg/24H	Moderate effect
thirty-nine	Eye toxicity	Eye penetration	rabbit	102 mg	Serious effect
forty	Eye toxicity	Eye penetration	rabbit	20 mg/24H	Moderate effect
forty-one	Mutagenic toxicity		Salmonella typhimurium	100 μg/plate
forty-two	Mutagenic toxicity		Escherichia coli	39658 μg/well/16H
forty-three	Mutagenic toxicity		Human lymphocytes	300 μmol/L
forty-four	Mutagenic toxicity	intraperitoneal injection	Rat	105 mg/kg
forty-five	Mutagenic toxicity		Salmonella typhimurium in rats	300 mg/kg
forty-six	Mutagenic toxicity		Rat liver	200 μmol/L
forty-seven	Mutagenic toxicity	intraperitoneal injection	mice	50 mg/kg
forty-eight	Mutagenic toxicity		Mouse lymphocyte	500 μmol/L
forty-nine	Mutagenic toxicity		Mouse lymphocyte	500 mg/L
fifty	Mutagenic toxicity		Mouse fibroblast	800 μg/L
fifty-one	Mutagenic toxicity	intraperitoneal injection	mice	300 mg/kg
fifty-two	Mutagenic toxicity		Mouse lymphocyte	21500 μmol/L
fifty-three	Mutagenic toxicity	Oral	mice	1 mg/kg
fifty-four	Mutagenic toxicity	intraperitoneal injection	mice	210 mg/kg
fifty-five	Mutagenic toxicity		Mouse lymphocyte	2500 μmol/L
fifty-six	Mutagenic toxicity		Hamster ovary	444 mg/L
fifty-seven	Mutagenic toxicity		Hamster ovary	50 mg/L
fifty-eight	Mutagenic toxicity		Hamster lung	500 μg/L
fifty-nine	carcinogenicity	Oral	Rat	11 mg/kg/29W-C	Carcinogenicity - tumor (according to RTECS standard) Kidney, ureter and bladder toxicity - tumor
sixty	carcinogenicity	Oral	Rat	72800 mg/kg/2Y-C	Carcinogenicity - tumor (according to RTECS standard) Hemotoxicity - Tumor
sixty-one	Reproductive toxicity	Oral	mice	4480 mg/kg, 6-13 days after female pregnancy	Reproductive toxicity - decreased weight gain of newborn

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