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Acetonitrile

The simplest organic nitrile Toxic and hazardous effects Purification methods Laboratory use Chemical properties Uses Production method Category Toxicity grading Acute toxicity Data of irritation Explosive characteristics Flammability characteristics Storage characteristics Professional standards
Acetonitrile
Acetonitrile structure
CAS No.
75-05-8
Chemical Name:
Acetonitrile
Synonyms
AN;ACN;AN2;MGDA;CH3CN;48484;ACY1L;NA 1648;C18orf14;CCDC102B
CBNumber:
CB2127174
Molecular Formula:
C2H3N
Formula Weight:
41.05
MOL File:
75-05-8.mol

Acetonitrile Properties

Melting point:
−48 °C(lit.)
Boiling point:
81-82 °C(lit.)
Density 
0.982 g/mL at 20 °C
vapor density 
1.41 (vs air)
vapor pressure 
72.8 mm Hg ( 20 °C)
refractive index 
n20/D 1.344(lit.)
Flash point:
48 °F
storage temp. 
2-8°C
solubility 
organic solvents: soluble(lit.)
pka
25(at 25℃)
form 
liquid
color 
<10(APHA)
Specific Gravity
approximate 0.78(20/20℃)
Odor
Aromatic ether-like odor detectable at 40 ppm
Relative polarity
0.46
explosive limit
3.0-17%(V)
Water Solubility 
miscible
λmax
λ: 195 nm Amax: ≤0.12
λ: 200 nm Amax: ≤0.032
λ: 230 nm Amax: ≤0.0044
λ: 235 nm Amax: ≤0.0044
λ: 250 nm Amax: ≤0.0044
λ: 400 nm Amax: ≤0.0044
Merck 
14,70
BRN 
741857
Exposure limits
TLV-TWA 70 mg/m3 (40 ppm) (ACGIH and OSHA); STEL 105 mg/m3 (60 ppm) (ACGIH); IDLH 4000 ppm (NIOSH).
Stability:
Stability Unstable. Incompatible with alkali metals, acids, bases, reducing agents and oxidizing agents. Highly flammable.
CAS DataBase Reference
75-05-8(CAS DataBase Reference)
NIST Chemistry Reference
Acetonitrile(75-05-8)
EPA Substance Registry System
Acetonitrile(75-05-8)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
Hazard Codes  F,Xi,Xn,T
Risk Statements  11-36-20/21/22-10-36/37/38-23/24/25-41-24-20/22
Safety Statements  16-36/37-45-36/37/39-27-26-36
RIDADR  UN 1993 3/PG 3
WGK Germany  2
RTECS  AL7700000
9
Autoignition Temperature 524 °C
Hazard Note  Highly Flammable/Harmful/Irritant
TSCA  Yes
HazardClass  3
PackingGroup  II
HS Code  29269095
Hazardous Substances Data 75-05-8(Hazardous Substances Data)
Toxicity LD50 orally in rats: 3800 mg/kg (Smyth)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H311 Toxic in contact with skin Acute toxicity,dermal Category 3 Danger P280, P302+P352, P312, P322, P361,P363, P405, P501
H312 Harmful in contact with skin Acute toxicity,dermal Category 4 Warning P280,P302+P352, P312, P322, P363,P501
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H332 Harmful if inhaled Acute toxicity,inhalation Category 4 Warning P261, P271, P304+P340, P312
H336 May cause drowsiness or dizziness Specific target organ toxicity,single exposure; Narcotic effects Category 3 Warning P261, P271, P304+P340, P312,P403+P233, P405, P501
H341 Suspected of causing genetic defects Germ cell mutagenicity Category 2 Warning P201,P202, P281, P308+P313, P405,P501
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233 Keep container tightly closed.
P240 Ground/bond container and receiving equipment.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P271 Use only outdoors or in a well-ventilated area.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P307+P311 IF exposed: call a POISON CENTER or doctor/physician.
P337+P313 IF eye irritation persists: Get medical advice/attention.
P370+P378 In case of fire: Use … for extinction.
P405 Store locked up.
P403+P235 Store in a well-ventilated place. Keep cool.
P501 Dispose of contents/container to..…

NFPA 704

Diamond Hazard Value Description
3
2 0
Health   2 Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury (e.g. diethyl ether, ammonium phosphate, iodine)
Flammability   3 Liquids and solids (including finely divided suspended solids) that can be ignited under almost all ambient temperature conditions . Liquids having a flash point below 22.8 °C (73 °F) and having a boiling point at or above 37.8 °C (100 °F) or having a flash point between 22.8 and 37.8 °C (73 and 100 °F). (e.g. gasoline, acetone)
Instability   0 Normally stable, even under fire exposure conditions, and is not reactive with water (e.g. helium,N2)
Special  

(NFPA, 2010)

Acetonitrile price More Price(195)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 110086 Acetonitrile ReagentPlus , 99% 75-05-8 1l $116 2018-11-13 Buy
Sigma-Aldrich 1012699 Alcohol Determination - Acetonitrile United States Pharmacopeia (USP) Reference Standard 75-05-8 5x5ml $401 2018-11-13 Buy
TCI Chemical A0793 Acetonitrile [for HPLC Solvent] >99.5%(GC) 75-05-8 500mL $110 2018-11-22 Buy
TCI Chemical A0293 Acetonitrile [for Spectrophotometry] >99.5%(GC) 75-05-8 100mL $45 2018-11-22 Buy
Alfa Aesar 022927 Acetonitrile, HPLC Grade, 99.7+% min 75-05-8 1L $80.2 2018-11-16 Buy

Acetonitrile Chemical Properties,Uses,Production

The simplest organic nitrile

Acetonitrile is the simplest organic nitrile, usually also called as nitrile methyl cyanide and methane. It is a colorless transparent liquid at room temperature. It is highly volatile, with special smell like ether, and flammable with flame burning brightly. It is mutually soluble in water, methanol, carbon tetrachloride, methyl acetate, ethyl acetate, ethylene dichloride, and many other non-saturated hydrocarbon solvents. It is toxic and can be metabolized into hydrogen cyanide and thiocyanate. Acetonitrile is a good solvent with excellent performance and is an important organic intermediate. It is also widely used as a polar aprotic solvent. The biggest application of acetonitrile is as a solvent which can be used as the solvents for the synthesis of vitamin A, cortisone, carbon amine drugs and their intermediates solvent. It also used as an active medium solvent in the manufacture of vitamin B1 and amino acids. It can substitute chlorinated solvents as a vinyl coating, an extracting agent of fatty acid, a alcohol denaturant, the extracting agent of butadiene, and the solvent of acrylonitrile synthetic fibers. It also has a lot of applications in fabric dyeing, light industry, spice manufacturing, and photographic materials manufacturing.

Toxic and hazardous effects

Acetonitrile class is produced by heating a mixture of glacial acetic acid and acetamide. It is an important industrial solvent primarily used for the medium of organic synthesis (e.g. acetophenone, 1-naphthyl acetic acid, thiamine, etc.), extracting agent of fatty acids, and alcohol denaturant. During the production process, exposure to liquid or vapor may cause poisoning.
[Clinical manifestations] Acute and occupational acetonitrile poisoning is not uncommon. There are many reports at both home and abroad. Vapor of acetonitrile has mild irritation so it can cause some degree of upper respiratory tract irritation in the case of high concentrations. Compared with hydrogen cyanide, acetonitrile although causes symptoms like nausea, vomiting, abdominal pain, diarrhea, chest pain, fatigue, and weakness, even respiratory depression in severe case, sometimes also causes hypotension, coma, and convulsions, but its onset process is relatively slow with the incubation period over 4H; nor does it cause illness as severe as hydrogen cyanide. It also rarely causes sudden death; For poisoned patients, their heart rates, pulse rates as well as the respiration rates decrease. They often got pale faces and also suffer kidney impairment like protein-urine. The toxicity of acetonitrile is not only related to the released CN-in vivo but also related to itself and its thiocyanate metabolites. There are currently no clinic products for treating chronic acetonitrile poisoning.
[Diagnosis and differential diagnosis] Diagnosis is mainly based on reliable history of exposure to large doses of acetonitrile and clinical characteristics, the appearance of similar poisoning effects for mutual contractees plays a obvious indication role; timely determination of plasma CN-, SCN-, and acetonitrile content is also indicative, and is the biomarker of contacting with acetonitrile. However, it cannot tell the existence and extent of poisoning. Acute acetonitrile poisoning should be paid attention to distinguish with toxic poisoning caused by other industrial toxic substance such as organic solvents, asphyxiating gas. It should also be distinguished from cerebrovascular accident, diabetic coma.
[Treatment] Refer to the content on treatment of hydrogen cyanide but cut the dose of methemoglobin forming agent by half. In the presence of sodium thiosulfate, we can apply in early phase of the slowly acted methemoglobin generation agents such as amino benzene acetone (PAPP). Taken one orally each time, and can repeat for every 4H. For the next day, maintaining with sodium thiosulfate is enough. The dosage of sodium thiosulfate can also be cut by half two days later and totally stopped after 3 to 5 days. Because of the toxic effect of the acetonitrile, when apply it as the antidote of cyanide antidote, people should be particularly participate in actively supportive treatment according to the symptomatic and supportive treatment, pay attention to the function maintenance of the heart, lung, brain, and apply rehydration for diuresis to accelerate the toxic discharge and reduce kidney impairment.

Purification methods

Industrially, acetonitrile is a byproduct of the reaction between propylene and ammonia which produces acrylonitrile, so often acetonitrile often contains water, acrylonitrile, ether, ammonia and some other impurities, even hydrolyzed acetic acid and ammonia. The purification method is as below:
1. Add phosphorus pentoxide (10-20g/L) into acetonitrile; heat and reflux until reaching colorless which can remove most water; avoid adding an excess of phosphorus pentoxide which will generate an orange polymer. Add a small amount of potassium carbonate into the distilled acetonitrile and continue distillation which can further remove excess phosphorus pentoxide; finally fractionate by fractional distillation column.
2. Use 36 g of mashed potassium permanganate and 28 g of mashed potassium carbonate to reflux 1L common anhydrous acetonitrile for 5 hours before evaporate it. Then add 10g of phosphorus pentoxide to the evaporated solvent; reflux for another 5 hours, fine slip, keeping the temperature constant, take the fraction of 81 °C.
3. Adding 4A molecular sieves or silica gel and shaking can also remove most of the water in acetonitrile. Next, stir it together with the calcium hydroxide until no hydrogen being further released; fractionate to get acetonitrile which also contain only a small amount of water without the existence of any acetate.
4. Acetonitrile can also be mixed together with methylene chloride, benzene and trichlorethylene for azeotropic distillation and drying.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Laboratory use

Acetonitrile is also used as a polar aprotic solvent.
In inorganic chemistry, acetonitrile is widely used as a ligand which is abbreviated MeCN. For example, acetonitrile complex PdCl2 (MeCN)2 can be produced by thermal polymerization of palladium chloride in the suspension of acetonitrile.
The high dielectric constant of acetonitrile makes it a popular cyclic voltammetry of solvents. Acetonitrile can also be used as a two-carbon raw material in organic synthesis. It can produce malononitrile via reaction with cyanogen chloride.
Acetonitrile can also be used as the mobile phase molecules which are commonly used in the column chromatography, more modernized high performance liquid chromatography (HPLC).
In the field of nuclear medicine, acetonitrile is used for the synthesis of radiopharmaceutical like fluoro-deoxy-glucose positron (FDG). During the synthesis of FDG, the evaporation of acetonitrile can take away the water in the reaction system. The exact content of acetonitrile in the reaction system plays a significant role in ensuring the synthesis efficiency and quality of medicines; at the same time, acetonitrile is also sued as the solvent and the matrix for the reaction system. In addition, in the routine quality inspection of FDG, acetonitrile: water mixture (for example, 85% v/v) is also applied as the mobile phase of TLC.

Chemical properties

Colorless; transparent liquid; has a unique fragrance similar to ether; miscible with water, methanol, methyl acetate, acetone, ether, chloroform, carbon tetrachloride and vinyl chloride miscible.

Uses

Acetonitrile is the raw material for preparing orthoacetate. It is also used as the intermediate of producing DV-acid methyl ester and 2-chloro-3,3,3-trifluoro-1-propenyl-2,2-dimethyl cyclopropanecarboxylate. It can also be used as the raw materials of making pyrimidine derivatives which is the intermediate of sulfonylurea herbicides. Moreover, it can be used for making vitamin B1 in the field of pharmaceutical industry and as the extraction agent of C4 fraction in the synthetic rubber industry.
Used as nitrile rubber monomer; Used for pharmaceutical industry and extraction of carbon IV.
As standard reference in chromatographic analysis; also as solvent and stationary phase for gas chromatography.
The major application of acetonitrile is as a solvent such as solvents for butadiene extraction, solvent for synthetic fibers and solvents for some special paints. In the oil industry, acetonitrile is used as the solvent for removing tar, phenol and other substances from petroleum hydrocarbons. It is also used as the solvent for extracting fatty acids from vegetable and animal oil in the fatty acid industry, and used as the reaction medium of the recrystallization of steroidal drugs in medicine industry. The binary azeotropic mixtures of acetonitrile and water are often used when a polar solvent of high dielectric constant is demanded: containing 84% acetonitrile, boiling point: 76 °C. Acetonitrile is used as the intermediate of pharmaceutical (vitamin B1) and spices, as the raw materials for making the synergist of triazine nitrogenous fertilizer, and also as a denaturant for ethyl alcohol. Moreover, it can also be used for synthesizing ethylamine, acetic acid, etc., and have many applications in textile dyeing and light industry.
It is used as the solvent of most inorganic compounds. It is also used as the solvent for spectrophotometric measurement, as a non-aqueous solvent, and as the diluents for determination of the carboxyl group. Furthermore, it is also applied in recrystallization of steroids and extraction of fatty acid, and also used as the solvents of High pressure liquid chromatography (HPLC).

Production method

There are many ways of making acetonitrile. Those major ways for industrial production include acetate amination method, acetylene amination method and propylene ammoxidation byproduct method. 1. Acetate amination method use acetate and ammonia as raw materials with reaction being performed at a temperature of 360-420 °C in the presence of aluminum oxide as the catalyst. This is a one-step synthesis method. The reaction mixture is further gone through water absorption and fine distillation to get the final product. Material consumption quantity: acetate (98%) 1763kg /t, ammonia (99.5%) 691kg/t. 2. Acetylene amination method uses ammonia and acetylene as the raw materials and the reaction is carried out at a temperature of 500-600 °C with aluminum oxide being the catalyst. It is again a one-step synthesis approach. Material consumption quantity: acetylene 10231 m3, ammonia (99.4%) 1007 kg/t. 3. Propylene amination and oxidation byproduct method use propylene, ammonia, and air as the raw materials. It produces acrylonitrile with the catalyst while producing acetonitrile as byproducts. Per ton of acrylonitrile can make 25-100kg byproduct of acetonitrile. 4. Made from the dehydration reaction between acetamide and phosphorus pentoxide. 5. Obtained from reaction between dimethyl sulfate and sodium cyanide.
Acetonitrile is usually the byproduct of ammoxidation reaction used for producing acrylonitrile. We can also apply acetate amination method with aluminum oxide as the catalyst. Acetonitrile is obtained by one-step reaction at 360 °C. Reaction equation:
CH3COOH + NH3 [Al2O3] → CH3CN + 2H2O.

Category

Flammable liquid

Toxicity grading

highly toxic

Acute toxicity

oral: rat LD50: 2730 mg/kg; Oral-Mouse LD50: 269 mg/kg.

Data of irritation

skin: rabbit 500 mg, Mild; Eyes-rabbit 79 mg/24 hours, moderate.

Explosive characteristics

Can be explosive when mixed with air.

Flammability characteristics

Flammable in case of fire, high temperature and oxidant; thermally decomposed to release highly toxic fumes of cyanide and nitrogen oxides.

Storage characteristics

Treasury: ventilation, low-temperature, dry; store it separately from oxidants and acids.

Professional standards

TWA 70 mg/m3; STEL 105 mg/m3.

Description

Acetonitrile is a colourless liquid, with an ether-like odour, and a polar solvent. Acetonitrile is predominantly used as a solvent in the manufacture of pharmaceuticals, for spinning fibers and for casting and molding of plastic materials, in lithium batteries, for the extraction of fatty acids from animal and vegetable oils, and in chemical laboratories for the detection of materials such as pesticide residues. Acetonitrile is also used in dyeing textiles and in coating compositions as a stabilizer for chlorinated solvents and in perfume production as a chemical intermediate. It is a by-product from the manufacture of acrylonitrile, and acetonitrile has, in fact, replaced the acrylonitrile. It is used as a starting material for the production of acetophenone, alpha-naphthaleneacetic acid, thiamine, and acetamidine. It has been used as a solvent in making pesticides, pharmaceuticals, batteries, rubber products, and formulations for nail polish remover despite its low but significant toxicity. Acetonitrile has been banned in cosmetic products in the European Economic Area (EEA) since early 2000, and acetone and ethyl are often preferred as safer for domestic use. Acetonitrile has a number of uses: primarily as an extraction solvent for butadiene; as a chemical intermediate in pesticide manufacturing; as a solvent for both inorganic and organic compounds to remove tars, phenols, and colouring matter from petroleum hydrocarbons not soluble in acetonitrile; in the production of acrylic fibres; and in pharmaceuticals, perfumes, nitrile rubber, and acrylonitrile butadiene styrene (ABS) resins; in high-performance liquid and gas chromatographic analysis; and in extraction and refining of copper.

Chemical Properties

Acetonitrile is a colorless liquid with an ether-like odor and a polar solvent. It is the simplest organic nitrile and is widely used. It is a by-product of the manufacture of acrylonitrile, and acetonitrile has, in fact, replaced acrylonitrile. It is used as a starting material for the produc- tion of acetophenone, alpha-naphthalenacetic acid, thiamine, and acetamidine. It has been used as a solvent and in making pesticides, pharmaceuticals, batteries, and rubber products, and formulations for nail polish remover, despite its low but signifi cant toxicity. Acetonitrile has been banned in cosmetic products in the European Economic Area (EEA) since early 2000 and acetone and ethyl are often preferred as safer for domestic use. Acetonitrile has a number of uses, primarily as an extraction solvent for butadiene; as a chemical interme- diate in pesticide manufacturing; as a solvent for both inorganic and organic compounds; to remove tars, phenols, and coloring matter from petroleum hydrocarbons not soluble in acetonitrile; in the production of acrylic fi bers; in pharmaceuticals, perfumes, nitrile rubber, and acrylonitrile-butadiene-styrene (ABS) resins; in high-performance liquid and gas chro- matographic analysis; and in extraction and refi ning of copper.

Chemical Properties

Acetonitrile is an extremely flammable, colorless liquid with an ethereal odor

Uses

Solvent

Uses

In organic synthesis as starting material for acetophenone, a-naphthaleneacetic acid, thiamine, acetamidine. To remove tars, phenols, and coloring matter from petroleum hydrocarbons which are not soluble in acetonitrile. To extract fatty acids from fish liver oils and other animal and vegetable oils. Can be used to recrystallize steroids. As an indifferent medium in physicochemical investigations. Wherever a polar solvent having a rather high dielectric constant is required. As medium for promoting reactions involving ionization. As a solvent in non-aqueous titrations. As a non-aqueous solvent for inorganic salts.

Uses

Acetonitrile is used as a solvent for polymers, spinning fibers, casting and molding plastics, and HPLC analyses; for extraction of butadiene and other olefins from hydrocarbon streams; in dyeing and coating textiles; and as a stabilizer for chlorinated solvents. It occurs in coal tar and forms as a by-product when acrylonitrile is made.

Production Methods

Acetonitrile is mainly prepared by dehydration of acetamide (CH3CONH2) with glacial acetic acid (Turner 1950) or by reacting acetic acid with ammonia at 400-500°C in the presence of a dehydration catalyst (Anon 1978).

General Description

A colorless limpid liquid with an aromatic odor. Flash point 42°F. Density 0.783 c / cm3. Toxic by skin absorption. Less dense than water. Vapors are denser than air.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

Acetonitrile decomposes when heated to produce deadly toxic hydrogen cyanide gas and oxides of nitrogen. Strongly reactive [Hawley]. May react vigorously with strong oxidizing reagents, sulfuric acid, chlorosulfonic acid, sulfur trioxide, perchlorates, nitrating reagents, and nitric acid. [Sax, 9th ed., 1996, p. 20]. Potentially explosive in contact with nitrogen-fluorine compounds (e.g., tetrafluorourea) [Fraser, G. W. et al., Chem. Comm., 1966, p. 532].

Health Hazard

Exposure to 160 ppm for 4 hours causes flushing of the face and a feeling of constriction in the chest; 500 ppm for brief periods is irritating to the nose and throat. Severe exposures cause irritability, skin eruptions, confusion, delirium, convulsions, paralysis, and death due to central nervous system depression.

Health Hazard

Acetonitrile liquid or vapor is irritating to the skin, eyes, and respiratory tract. Acetonitrile has only a modest toxicity, but it can be metabolized in the body to hydrogen cyanide and thiocyanate. Acetonitrile causes delayed symptoms of poisoning (several hours after the exposure) that include, but are not limited to, salivation, nausea, vomiting, anxiety, confusion, hyperpnea, dyspnea, respiratory distress, disturbed pulse rate, unconscious- ness, convulsions, and coma. Cases of acetonitrile poisoning in humans (or, more strictly, of cyanide poisoning after exposure to acetonitrile) are rare but not unknown, by inha- lation, ingestion, and (possibly) by skin absorption. Repeated exposure to acetonitrile may cause headache, anorexia, dizziness, weakness, and macular, papular, or vesicular dermatitis.

Health Hazard

Several cases of accidental poisoning were caused by inhalation of acetonitrile in different work places. Signs of toxicity include: bronchial tightness, gastric distress, respiratory distress, hypotension, hypersecretion of saliva, conjunctivitis, skin discoloration, tachypnea, general weakness, absence of deep reflexes, coma and death in some cases (Grabois 1955; Amdur 1959; Dequidt et al 1974; and Pozzani et al 1959). Postmortem analysis for cyanide and thiocyanate revealed that of all tissues, the spleen contained the largest amount of cyanide. While high levels of thiocyanate were found in the lungs, the largest amounts of acetonitrile were found in the liver and kidneys.

Health Hazard

The toxicity of acetonitrile to human and test animals is considerably lower than that of some other nitriles. However, at high concentrations, this compound could produce severe adverse effects. The target organs are the kidney, liver, central nervous system, lungs, cardiovascular system, skin, and eyes. In humans, inhalation of its vapors can cause asphyxia, nausea, vomiting, and tightness of the chest. Such effects can probably be manifested at several hours exposure to concentration in air above 400–500 ppm. At a lower concentration of 100 ppm, only a slight adverse effect may be noted. It is excreted in the urine as cyanate. The blood cyanide concentration does not show any significant increase in cyanide at low concentrations.
The acute oral toxicity of acetonitrile is generally of low order. The toxic symptoms associated with oral intake can be gastrointestinal pain, nausea, vomiting, stupor, convulsion, and weakness. These effects may become highly marked in humans from ingestion of 40–50 mL of acetonitrile. Freeman and Hayes (1985) observed toxicological interaction between acetone and acetonitrile when administered in rats by oral dose. There was a delay in the onset of toxicity (due to acetonitrile) and an elevation of blood cyanide concentration when the dose consisted of a mixture of acetone and acetonitrile. Acetone inhibited the cyanide formation. The toxicity of both the solvents were prevented by administering sodium thiosulfate. Sodium nitrite also provided protection against mortality from lethal concentrations (Willhite 1981). Intraperitoneal administration of acetonitrile resulted in damage to cornea, ataxia, and dyspnea in mice. It is an eye and skin irritant.
LD50 value, oral (mice): 269 mg/kg
LD50 value, intraperitoneal (mice): 175 mg/kg
Ahmed et al. (1992) studied kinetics of acetonitrile distribution in mice by autoradiography. The study revealed heavy localization of acetonitrile metabolites in the gastrointestinal tissues and bile. Initially, the highest levels of radioactivity were detected in the liver and kidney which declined over time. At 24- and 48 hours after exposure the radioactivity was detected in gastrointestine, thymus, liver, and male reproductive organs. The study also indicated that 40 to 50% of total radioactivity was present in the liver, covalently bound to the macromolecular fractions of the tissues while the remaining radioactivity in the other organs were present in the lipid fraction of the tissue.
Acetonitrile is a teratomer. Pregnant hamsters were exposed to this compound by inhalation, ingestion, or injection during the early stage of embryogenesis. Severe axial skeletal disorders resulted in the offspring at a high concentration of 5000–8000 ppm (inhalation) or 100–400 mg/kg (oral dose) (Willhite 1983). Teratogenic effects were attributed to the release of cyanide, which was detected in high concentrations along with thiocyanate in all tissues after an oral or intraperitoneal dose. Sodium thiosulfatetreated hamsters did not display a teratogenic response to acetonitrile.
A 2-year inhalation studies (NTP 1996) showed a marginally increased incidence of hepatocellular adenoma and carcinoma in male rats exposed to 100, 200, or 400 ppm acetonitrile for 6 hours per day, 5 days per week. However, there was no incidence of carcinogenic activity in female rats and male and female mice.

Fire Hazard

Flammable liquid; flash point (open cup) 5.5°C (42°F); vapor pressure 73 torr at 20°C (68°F); vapor density at 38°C (100°F) 1.1 (air = 1); the vapor is heavier than air and can travel some distance to a source of ignition and flash back; ignition temperature 524°C (975°F); fire-extinguishing agent: dry chemical, CO2, or “alcohol” foam; use a water spray to flush and dilute the spill and keep fire-exposed containers cool.
Muraki et al. (2001) have reported a case of systemic rhabdomyolysis and acute renal failure in a 35-year old man after acetonitrile exposure. The symptoms were vomiting, convulsion, and loss of consciousness 15 hours after exposure. Initial therapy against cyanide poisoning was only partially effective.
Acetonitrile vapors form an explosive mixture with air; the LEL and UEL values are 4.4% and 16.0% by volume of air, respectively. It reacts with strong oxidizers and acids, liberating heat along with pressure increase. Thus contact in a close container can result in rupture of the container. Erbium perchlorate tetrasolvated with acetonitrile when dried to disolvate exploded violently on light friction (Wolsey 1973). Neodymium perchlorate showed similar heat and shock sensitivity when dried down to lower levels of solvation (Chemical & Engineering News, Dec. 5, 1983). Bretherick (1990) proposed that the tendency for oxygen balance to shift toward zero for maximum energy release, with diminishing solvent content, decreased the stability of solvated metal perchlorates at lower levels of solvation. Such a zero balance for maximum exotherm should occur at 2.18 mol of acetonitrile solvated to metal perchlorate. Metals such as lithium react exothermically with acetonitrile at ambient temperature (Dey and Holmes 1979).

Flammability and Explosibility

Acetonitrile is a flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." Acetonitrile vapor forms explosive mixtures with air at concentrations of 4 to 16% (by volume).
Hazardous gases produced in a fire include hydrogen cyanide, carbon monoxide, carbon dioxide, and oxides of nitrogen. Carbon dioxide or dry chemical extinguishers should be used for acetonitrile fires.

Industrial uses

Acetonitrile is used as a solvent both in industry and in the laboratory, as a rodenticide, and in the denaturation of alcohol. Because of both its solvent properties and volatility, it is useful for extracting vegetable and animal oils and dissolving hydrocarbons, oils, and greases. Acetonitrile is used for the purification of acetylene and artificial textile fibers, and as an antioxidant for rubber (Dequidt et al 1974). It has also been used to extract herbicide residues from soils (Smith 1980), to remove tars and other compounds from petroleum hydrocarbons, and to extract fatty acids from vegetable and fish liver oil. Acetonitrile is now a standard solvent component in reversed-phase high-performance liquid chromatography. It is the starting point for the syntheses of a number of organic compounds such as carboxylic acids and various nitrogen derivatives (Smiley 1981).

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by several routes. An experimental teratogen. Other experimental reproductive effects. A skin and severe eye irritant. Human systemic effects by ingestion: convulsions, nausea or vomiting, and metabolic acidosis. Human respiratory system effects by inhalation. Mutation data reported. Dangerous fire hazard when exposed to heat, flame, or oxidizers. Explosion Hazard: See also CYANIDE and NITRILES. When heated to decomposition it emits highly toxic fumes of CNand NOx,. Potentially explosive reaction with lanthanide perchlorates and nitrogen-fluorine compounds. Exothermic reaction with sulfuric acid at 53°C. Will react with water, steam, acids to produce toxic and flammable vapors. Incompatible with oleum, chlorosulfonic acid, perchlorates, nitrating agents, inchum, dinitrogen tetraoxide, N-fluoro compounds (e.g., perfluorourea + acetonitrile), HNO3, so3. To fight fire, use foam, Con, dry chemical

Potential Exposure

Acetonitrile is used as an extractant for animal and vegetable oils, as a solvent; particularly in the pharmaceutical industry, and as a chemical intermediate in pesticide manufacture; making batteries and rubber products. It is present in cigarette smoke

First aid

Acetonitrile can cause fatal Cyanide poisoning. A cyanide antidote kit should be kept in the immediate work area and must be rapidly available. Kit ingredients should be replaced every 1 2 years to ensure freshness. Persons trained in the use of this kit; oxygen use, and CPR must be available within 1 2 minutes. In the event of overexposure, and/or symptoms: move victim to fresh air; call emergency medical care. Give Amyl Nitrate capsules (as directed, by trained personnel only). If this chemical gets into the eyes, remove any contact lenses at once, and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, quickly remove contaminated clothing and wash with large amounts of water. Speed in removing material from skin is of extreme importance. Seek medical attention immediately. When this chemical has been swallowed, get medical attention immediately. If this chemical has been inhaled, remove from exposure and transfer promptly to a medical facility. If not breathing, give artificial respiration (avoid mouth to mouth resuscitation). If breathing is difficult, give oxygen. If heart has stopped, begin CPR. Keep victim quiet and maintain normal body temperature. Effects may be delayed; keep victim under observation. Avoid contact with contaminated skin. Observe victim for 24 to 48 hours.

Metabolism

Acetonitrile metabolism in dogs was demonstrated by Lang (1894), who reported that about 20% of the nitrile administered was converted to thio-cyanate in the urine, while guinea pigs metabolized acetonitrile to a greater extent (50% of dose excreted as thiocyanate). When the animals were pre-treated with ethanol, acetonitrile metabolism was induced (Tanii and Hashimoto 1986). In rats, acetone was found to potentiate acetonitrile toxicity and elevate cyanide concentrations in the blood (Freeman and Hays 1985). Baumann et al (1933) found that rabbits injected with acetonitrile excreted 27-35% of the dose as thiocyanate, while in thyroidectomized rabbits, the excretion decreased significantly (3-5% of the dose). Thiocyanate excretion was increased notably upon feeding dessicated thyroid to these animals. Hunt (1923) found that powdered sheep thyroid protected mice against acetonitrile toxicity. However, the role played by the thyroid in the detoxication of cyanide to thiocyanate is unclear. It has been suggested that the thyroid may have a role in the microsomal cleavage of cyanide from acetonitrile other than its direct effect on sulphation of cyanide to thiocyanate.
The nature of oxidizing enzymes for nitriles in general, including acetonitrile have been studied by Ahmed and Patel (1979). The enzymes were localized in the hepatic microsomal fraction and required NADPH as a cofactor in the presence of oxygen. In recent studies on the mammalian metabolism of acetonitrile, the mechanisms of cyanide liberation, and the enzymes involved, have also been reported by Tanii and Hashimoto (1984, 1986) and Freeman and Hays (1988). These studies confirmed the role of microsomal mixed function oxidase in the metabolism of acetonitrile.
Firmin and Gray (1976) studied the fate of acetonitrile in the bacterium Pseudomonas. They found that [14C]-acetonitrile is metabolized to citrate, succinate, fumarate, malate, glutamate, pyrrolidonecarboxylic acid, and asparate. They reported that this species of bacteria metabolized acetonitrile by direct hydrolysis of the cyanide moiety to acetamide. Although it is possible that a similar reaction may occur in mammalian systems, it has not yet been reported.

storage

Acetonitrile should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers.

Shipping

UN1648 Acetonitrile, Hazard Class: 3; Labels: 3-Flammable liquid

Purification Methods

Commercial acetonitrile is a by-product of the reaction of propylene and ammonia to acrylonitrile. The following procedure that significantly reduces the levels of acrylonitrile, allyl alcohol, acetone and *benzene was used by Kiesel [Anal Chem 52 2230 1988]. Methanol (300mL) is added to 3L of acetonitrile fractionated at high reflux ratio until the boiling temperature rises from 64o to 80o, and the distillate becomes optically clear down to = 240nm. Add sodium hydride (1g) free from paraffin, to the liquid, reflux for 10minutes, and then distil rapidly until about 100mL of residue remains. Immediately pass the distillate through a column of acidic alumina, discarding the first 150mL of percolate. Add 5g of CaH2 and distil the first 50mL at a high reflux ratio. Discard this fraction, and collect the following main fraction. The best way of detecting impurities is by gas chromatography. Usual contaminants in commercial acetonitrile include H2O, acetamide, NH4OAc and NH3. Anhydrous CaSO4 and CaCl2 are inefficient drying agents. Preliminary treatment of acetonitrile with cold, saturated aqueous KOH is undesirable because of base-catalysed hydrolysis and the introduction of water. Drying by shaking with silica gel or Linde 4A molecular sieves removes most of the water in acetonitrile. Subsequent stirring with CaH2 until no further hydrogen is evolved leaves only traces of water and removes acetic acid. The acetonitrile is then fractionally distilled at high reflux, taking precaution to exclude moisture by refluxing over CaH2 [Coetzee Pure Appl Chem 13 429 1966]. Alternatively, 0.5-1% (w/v) P2O5 is often added to the distilling flask to remove most of the remaining water. Excess P2O5 should be avoided because it leads to the formation of an orange polymer. Traces of P2O5 can be removed by distilling from anhydrous K2CO3. Kolthoff, Bruckenstein and Chantooni [J Am Chem Soc 83 3297 1961] removed acetic acid from 3L of acetonitrile by shaking for 24hours with 200g of freshly activated alumina (which had been reactivated by heating at 250o for 4hours). The decanted solvent was again shaken with activated alumina, followed by five batches of 100-150g of anhydrous CaCl2. (Water content of the solvent was then less than 0.2%.) It was shaken for 1hour with 10g of P2O5, twice, and distilled in a 1m x 2cm column, packed with stainless steel wool and protected from atmospheric moisture by CaCl2 tubes. The middle fraction had a water content of 0.7 to 2mM. Traces of unsaturated nitriles can be removed by initially refluxing with a small amount of aqueous KOH (1mL of 1% solution per L). Acetonitrile can be dried by azeotropic distillation with dichloromethane, *benzene or trichloroethylene. Isonitrile impurities can be removed by treatment with conc HCl until the odour of isonitrile has gone, followed by drying with K2CO3 and distilling. Acetonitrile is refluxed with, and distilled from alkaline KMnO4 and KHSO4, followed by fractional distillation from CaH2. (This is better than fractionation from molecular sieves or passage through a type H activated alumina column, or refluxing with KBH4 for 24hours and fractional distillation)[Bell et al. J Chem Soc, Faraday Trans 1 73 315 1977, Moore et al. J Am Chem Soc 108 2257 1986]. Material suitable for polarography is obtained by refluxing over anhydrous AlCl3 (15g/L) for 1hour, distilling, refluxing over Li2CO3 (10g/L) for 1hour and redistilling. It is then refluxed over CaH2 (2g/L) for 1hour and fractionally distilled, retaining the middle portion. The product is not suitable for UV spectroscopy use. A better purification procedure uses refluxing over anhydrous AlCl3 (15g/L) for 1hour, distilling, refluxing over alkaline KMnO4 (10g KMnO4, 10g Li2CO3/L) for 15minutes, and distilling. A further reflux for 1hour over KHSO4 (15g/L), then distillation, is followed by refluxing over CaH2 (2g/L) for 1hour, and fractional distillation. The product is protected from atmospheric moisture and stored under nitrogen [Walter & Ramalay Anal Chem 45 165 1973]. Purificaton of "General Purity Reagent" for this purpose is not usually satisfactory because very large losses occur at the KMnO4/LiCO3 step. For electrochemical work involving high oxidation fluorides, further reflux over P2O5 (1g/mL for 0.5hours) and distilling (discarding 3% of first and last fractions) and repeating this step is necessary. The distillate is kept over molecular sieves in vacuo after degassing, for 24hours and distilling in a vacuum onto freshly activated 3A molecular sieves. The MeCN should have absorption at 200nm of <0.05 (H2O reference) and UV cutoff at ca 175nm. Also the working potential range of purified Et4N+ BF4 (0.1mol.dcm-3 in the MeCN) should be +3.0 to -2.7V vs Ag+/Ago. If these criteria are not realised then further impurities can be removed by treatment with activated neutral alumina (60 mesh) in vacuo before final molecular sieves treatment [Winfield J Fluorine Chem 25 91 1984]. Acetonitrile has been distilled from AgNO3, collecting the middle fraction over freshly activated Al2O3. After standing for two days, the liquid is distilled from the activated Al2O3. The specific conductivity should be 0.8-1.0 x 10-8 mhos [Harkness & Daggett Can J Chem 43 1215 1965]. Acetonitrile 14C is best purified by gas chromatography and is water free and distils at 81o. [Beilstein 2 H 183, 2 IV 419.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, chlorosulfonic acid, oleum, epoxides. May accumulate static electrical charges, and may cause ignition of its vapors. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration with nitrogen oxide removal from effluent gases by scrubbers or incinerators

Acetonitrile Preparation Products And Raw materials

Raw materials

Preparation Products


Acetonitrile Suppliers

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