acetonitrile

Organic compound

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This entry is made by China Science and Technology Information Magazine Participate in editing and review Science Popularization China · Science Encyclopedia authentication.

Acetonitrile is a kind of Organic compound , chemical formula is CH three CN or C two H three N^[3] , a colorless transparent liquid, has excellent solvent performance, can dissolve a variety of organic, inorganic and gaseous substances, and is infinitely miscible with water and alcohol. Acetonitrile can produce typical nitrile reactions and is used to prepare many typical Nitrogenous compound , is an important organic intermediate.

Chinese name: acetonitrile^[5]
Foreign name: Acetonitrile^[5]
Alias: Methyl cyanide
chemical formula: C two H three N^[5]
molecular weight: forty-one point zero five two^[5]
CAS login number: 75-05-8^[5]
EINECS login number: 200-835-2^[5]
Melting point: -45 ℃^[5]

Boiling point: 81 to 82 ℃
Water solubility: Soluble
Density: 0.786 g/cm³
Appearance: Colorless Transparent Liquid
Flash point: 2 ℃^{[6 ]}
Security description: S16；S26；S27；S36/37/39；S45^[5]
Hazard symbol: F^[5]
Hazard description: R11；R20/21/22；R36^[5]

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Physical and chemical properties

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Density: 0.786g/cm three

Melting point: - 45 ℃

Boiling point: 81-82 ℃

Flash point: 2 ℃ (CC)^{[6 ]}

Refractive index: 1.344 (20 ℃)

Saturated vapor pressure: 13.33kPa (27 ℃)^[5]

Critical temperature: 274.7 ℃^[5]

Critical pressure: 4.83MPa^[5]

Ignition temperature: 524 ℃^[5]

Upper explosive limit（ V / V ）：16.0%^[5]

Lower explosive limit（ V / V ）：3.0%^[5]

Appearance: colorless transparent liquid

Solubility: miscible with water, soluble in ethanol 、 Ether Most organic solvents^[4]

Molecular structure data

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Molar refractive index: 11.22^[5]

Molar volume (cm three /mol）：54.9^[5]

Isotonic specific volume (90.2K): 120.0^[5]

Surface tension (dyne/cm): 22.7^[5]

Polarization (10 -24 cm three ）：4.45^[4]

Calculate chemical data

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Drainage parameter calculation reference value (XlogP): 0^[5]

Number of hydrogen bond donors: 0^[5]

Number of hydrogen bond receptors: 1^[5]

Number of rotatable chemical bonds: 0^[5]

Number of tautomers: 0

Topological molecule polar surface area (TPSA): 23.8^[5]

Number of heavy atoms: 3^[5]

Surface charge: 0^[5]

Complexity: 29.3^[5]

Number of isotope atoms: 0^[5]

Determine the number of atomic structure centers: 0^[5]

Number of uncertain atomic structure centers: 0^[5]

Determine the number of chemical bond structure centers: 0^[5]

Number of uncertain chemical bond structure centers: 0^[5]

Number of covalent bond units: 1^[4]

purpose

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1. Chemical analysis and instrumental analysis

Acetonitrile has been used in recent years Thin layer chromatography 、 Paper chromatography 、 spectrum and Polarography Organic modifiers and solvents analyzed. Since high-purity acetonitrile does not absorb ultraviolet light at 200nm~400nm, one application under development is as high performance liquid chromatography HPLC The analytical sensitivity can be up to 10 -9 Level.

2. Hydrocarbon extraction and separation solvent

Acetonitrile is a widely used solvent, mainly used as the solvent for extractive distillation four Separation in hydrocarbons butadiene 。 Acetonitrile is also used for the separation of other hydrocarbons, such as separating from hydrocarbon fractions propylene 、 isoprene and Methyl acetylene Etc. Acetonitrile is also used for some special separation, such as extraction and separation from vegetable oil and cod liver oil fatty acid The treated oil is light and pure, and the smell is improved, while the vitamin content remains unchanged. Acetonitrile is also widely used as solvent in pharmaceutical, pesticide, textile and plastic sectors.^[2]

3. Intermediates of synthetic medicine and pesticide

Acetonitrile can be used as an intermediate in the synthesis of many medicines and pesticides. In medicine, it is used to synthesize a series of important pharmaceutical intermediates, such as vitamin B1, metronidazole, ethambutol, aminopteridine, adenine and dipyridamole; In pesticides, it is used to synthesize pesticide intermediates such as pyrethroid insecticides and acetamicarb.^[1]

4. Semiconductor cleaner

Acetonitrile is an organic solvent with strong polarity, which has good solubility in grease, inorganic salt, organic matter and macromolecular compound, and can clean grease, wax, fingerprint, corrosive agent and flux residue on silicon wafer. Therefore, high-purity acetonitrile can be used as semiconductor cleaning agent.

5. Other applications

In addition to the above applications, acetonitrile can also be used as raw material for organic synthesis, catalyst or component of transition metal complex catalyst. In addition, acetonitrile is also used in fabric dyeing and coating compounds, and it is also an effective stabilizer of chlorinated solvents.

toxicology data

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1、 acute toxicity

LD fifty : 2460mg/kg (rat by mouth); 1250mg/kg (rabbit percutaneous)

LC fifty : 7551ppm (inhaled by rats, 8h)

2、 thrill

Rabbit percutaneous: 500mg, mild stimulation (open stimulation test)

3. Subacute and chronic toxicity

Cats inhale its vapor 7mg/m three , 4 hours a day for 6 months. One month after exposure, the conditioned reflex began to break. Pathological examination showed pathological changes of liver, kidney and lung.

4、 Mutagenicity

Sex chromosome Absence and non separation: saccharomyces cerevisiae 47600ppm。 Sister chromatid exchange : Hamster ovary 5g/L。

5、 Teratogenicity

The lowest toxic dose (TCLo) of 5000ppm (1h) inhaled by hamsters 8 days after pregnancy caused central nervous system Developmental malformation.

The lowest toxic dose (TCLo) of 8000ppm (1h) inhaled by hamsters 8 days after pregnancy will lead to the malformation of musculoskeletal system.

6. Other toxicity

The lowest oral toxic dose (TDLo) of hamsters: 300mg/kg (8 days of pregnancy), causing abnormal musculoskeletal development.

7、 Ecotoxicity

LC5 zero ：1640mg/L（96h）（ Pimephales promelas ）

8、 Biodegradability

Aerobic biodegradability: 168~672h

Anaerobic biodegradability: 672~2688h

9. Non biodegradable

Photooxidation half-life in water: 2.80 × 10 six ~1.10×10 eight h

Photooxidation half-life in air: 1299~12991h

First level hydrolysis half-life: ＞ 150000ah

Toxicity test data
number	Toxicity type	test method	Test object	Dosage	Toxic effect
one	acute toxicity	Oral	adult female	500 mg/kg	Behavioral toxicity - coma Cardiotoxicity - heart rate increases, blood pressure does not decrease Lung, chest or respiratory toxicity - respiratory suppression
two	acute toxicity	Oral	children	800 mg/kg	Behavioral toxicity - hallucination, perception distortion Behavioral toxicity - convulsion or seizure threshold affected Gastrointestinal toxicity - nausea and vomiting
three	acute toxicity	Oral	Adult male	571 mg/kg	Behavioral toxicity - convulsion or seizure threshold affected Gastrointestinal toxicity - nausea and vomiting Nutritional and metabolic system toxicity - metabolic acidosis
four	acute toxicity	Oral	Adult male	64 mg/kg	Behavioral toxicity - excitement
five	acute toxicity	inhalation	human beings	160 ppm/4h	Lung, chest or respiratory toxicity - other changes
six	acute toxicity	Oral	Rat	2460 mg/kg	No values other than lethal dose were reported for detailed effects
seven	acute toxicity	inhalation	Rat	7551 ppm/8h	Behavioral toxicity - changes in sleep time (including changes in righting reflex) Behavioral toxicity - convulsion or seizure threshold affected Hemotoxicity - bleeding
eight	acute toxicity	intraperitoneal injection	Rat	850 mg/kg	No values other than lethal dose were reported for detailed effects
nine	acute toxicity	subcutaneous injection	Rat	3500 mg/kg	No values other than lethal dose were reported for detailed effects
ten	acute toxicity	intravenous injection	Rat	1680 mg/kg	No values other than lethal dose were reported for detailed effects
eleven	acute toxicity	Extraintestinal	Rat	1100 mg/kg	No values other than lethal dose were reported for detailed effects
twelve	acute toxicity	Oral	mice	269 mg/kg	No values other than lethal dose were reported for detailed effects
thirteen	acute toxicity	inhalation	mice	2693 ppm/1h	Hepatotoxicity - other changes
fourteen	acute toxicity	intraperitoneal injection	mice	175 mg/kg	Eye toxicity - corneal injury Behavioral toxicity - ataxia Lung, chest or respiratory toxicity - dyspnea
fifteen	acute toxicity	subcutaneous injection	mice	4480 mg/kg	No values other than lethal dose were reported for detailed effects
sixteen	acute toxicity	intravenous injection	mice	612 mg/kg	No values other than lethal dose were reported for detailed effects
seventeen	acute toxicity	inhalation	dog	16000 ppm/4h	No values other than lethal dose were reported for detailed effects
eighteen	acute toxicity	Oral	cat	200 mg/kg	No values other than lethal dose were reported for detailed effects
nineteen	acute toxicity	inhalation	cat	18 mg/m three	No values other than lethal dose were reported for detailed effects
twenty	acute toxicity	Oral	rabbit	50 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-one	acute toxicity	inhalation	rabbit	2828 ppm/4h	Behavioral toxicity - changes in sleep time (including changes in righting reflex) Behavioral toxicity - convulsion or seizure threshold affected Hemotoxicity - bleeding
twenty-two	acute toxicity	skin surface	rabbit	>2 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-three	acute toxicity	subcutaneous injection	rabbit	105 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-four	acute toxicity	Oral	guinea pig	177 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-five	acute toxicity	inhalation	guinea pig	5655 ppm/4h	Behavioral toxicity - changes in sleep time (including changes in righting reflex) Behavioral toxicity - convulsion or seizure threshold affected Hemotoxicity - bleeding
twenty-six	acute toxicity	subcutaneous injection	frog	9100 mg/kg	Peripheral neurotoxicity - spastic paralysis or no sensory change Lung, chest or respiratory toxicity - dyspnea
twenty-seven	acute toxicity	Oral	mammal	1670 mg/kg	No values other than lethal dose were reported for detailed effects
twenty-eight	Chronic toxicity	inhalation	Rat	655 ppm/7h/90D-I	Lung, chest or respiratory toxicity - chronic pulmonary edema Hepatotoxicity - other changes Kidney, ureter and bladder toxicity - changes in renal tubules (including acute renal failure and acute tubular necrosis)
twenty-nine	Chronic toxicity	inhalation	Rat	800 ppm/6h/13W-I	Behavioral toxicity - sleepiness Behavioral toxicity - ataxia Chronic disease related toxicity - death
thirty	Chronic toxicity	inhalation	mice	800 ppm/6h/13W-I	Behavioral toxicity - sleepiness Lung, chest or respiratory toxicity - chronic pulmonary edema Chronic disease related toxicity - death
thirty-one	Chronic toxicity	inhalation	dog	350 ppm/7h/91D-I	Nutrition and metabolic system toxicity - weight loss or weight gain rate decrease
thirty-two	Chronic toxicity	inhalation	monkey	350 ppm/7h/91D-I	Brain toxicity - changes in blood circulation (such as bleeding or thrombosis) Lung, chest or respiratory toxicity - emphysema Blood toxicity - red blood cell count changes
thirty-three	Eye toxicity	skin surface	rabbit	500 mg	Less effective
thirty-four	Eye toxicity	Eye penetration	rabbit	100 μL/24h	Moderate effect
thirty-five	Mutagenic toxicity	inhalation	Drosophila melanogaster	131 ppm
thirty-six	Mutagenic toxicity		Saccharomyces cerevisiae	47600 ppm
thirty-seven	Mutagenic toxicity		Hamster ovary	5 gm/L
thirty-eight	carcinogenicity	inhalation	Rat	400 ppm/6h/2Y-I	Carcinogenicity - possible carcinogenicity (according to RTECS standard) Hepatotoxicity - Tumor
thirty-nine	Reproductive toxicity	inhalation	Rat	1800 ppm/6h, 6-20 days after female pregnancy	Reproductive toxicity - increased mortality after implantation
forty	Reproductive toxicity	Oral	rabbit	390 mg/kg, 6-18 days after female pregnancy	Reproductive toxicity - affecting the mother Reproductive toxicity - death of embryos or fetuses Reproductive toxicity - musculoskeletal dysplasia
forty-one	Reproductive toxicity	Oral	Hamster	300 mg/kg, 8 days after female pregnancy	Reproductive toxicity - musculoskeletal dysplasia
forty-two	Reproductive toxicity	Oral	Hamster	400 mg/kg, 8 days after female pregnancy	Reproductive toxicity - increased mortality after implantation
forty-three	Reproductive toxicity	inhalation	Hamster	5000 ppm/1h, 8 days after female conception	Reproductive toxicity - increased mortality after implantation Reproductive toxicity - central nervous system dysplasia
forty-four	Reproductive toxicity	inhalation	Hamster	8000 ppm/1h, 8 days after female conception	Reproductive toxicity - such as fetal dysplasia, but not death Reproductive toxicity - musculoskeletal dysplasia

First aid measures

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Skin contact: Take off the contaminated clothes and wash the skin thoroughly with soapy water and clean water.

Eye contact: Lift the eyelid and flush with flowing water or physiological saline. 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 and seek medical advice.

Ingestion: If the patient is conscious, induce vomiting, gastric lavage and seek medical advice.

Fire fighting measures

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Hazard characteristics: flammable, its vapor and air can form an explosive mixture, which may cause combustion and explosion in case of open fire, high heat or contact with oxidant. It can react strongly with oxidants. There is a luminous flame when burning. It reacts violently with sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, perchlorate, etc.

Hazardous combustion products: carbon monoxide 、 carbon dioxide 、 Nitrogen oxide 、 Hydrogen cyanide 。

Fire extinguishing method: spray water to cool the container, and move the container from the fire site to an open place if possible.

Extinguishing agent: insoluble foam, dry powder, carbon dioxide, sand. Fire extinguishing with water is invalid.

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 with activated carbon or other inert materials. A large amount of water can also be used for flushing, and the diluted washing water will be discharged into the waste water system.

Large amount of leakage: build a dike or dig a pit to receive. Spray water cools and dilutes steam, protects on-site personnel, and dilutes leakage into incombustible materials. Use explosion-proof pump to transfer to tank car or special collector for recycling or transport to waste disposal site.

Handling and storage

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Precautions for operation: it shall be strictly sealed, and sufficient local exhaust and general ventilation shall be provided. 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 (full face masks), self-contained breathing apparatus or ventilated breathing apparatus, adhesive tape gas suits 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. Keep away from flammable and combustible materials. Prevent vapor leakage into the air of the workplace. Avoid contact with oxidants, reducing agents, acids and alkalis. 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 warehouse temperature should not exceed 30 ℃. Keep container sealed. It shall be stored separately from oxidants, reducing agents, acids, alkalis, combustibles and edible chemicals, and mixed storage is strictly prohibited. Explosion proof lighting and ventilation facilities shall be adopted. It is prohibited to use mechanical equipment and tools that are easy to generate sparks. The storage area shall be equipped with leakage emergency treatment equipment and appropriate materials.