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Acetonitrile, also known as cyanomethane, ethanenitrile or methyl cyanide is a chemical compound with the formula CH3CN.

PropertiesEdit

ChemicalEdit

Acetonitrile reacts with aldehydes to form hydroxynitriles.

R-CHO + CH3CN → R-CH(OH)-CH2(CN)[1]

Palladium chloride will form a complex with acetonitrile:

PdCl2 + 2 CH3CN → PdCl2[CH3CN]2

PhysicalEdit

Acetonitrile is a colorless liquid, with a faint ether like smell and a sweet burnt smell. Acetonitile is hygroscopic, and will readily absorb water from air if kept in open air. It has a melting point between −46 to −44 °C and a boiling point between 81.3 to 82.1 °C.

AvailabilityEdit

Acetonitrile can be purchased from chemical suppliers. ScienceStuff sells 1 liter at $76.88 + UPS hazardous material surcharge of $28.50 per shipment.

PreparationEdit

Acetonitrile can be made by dehydrating acetamide, which itself results from the thermal decomposition of ammonium acetate.

CH3COONH4 → CH3C(O)NH2 + H2O
CH3C(O)NH2 → CH3CN + H2O

ProjectsEdit

HandlingEdit

SafetyEdit

Acetonitrile has modest toxicity in small doses, but it will be metabolised by the organism to produce hydrogen cyanide, which is very toxic. This occurs several hours after the exposure. Acetonitrile can be absorbed through the skin and via inhalation, so proper protection, such as gloves and a mask should be worn.

Acetonitrile however, has a much lower toxicity than the other simple nitriles, with a LD50 of 2460 mg/kg, while the next simple nitriles (propionitrile, butyronitrile, malononitrile, acrylonitrile) have values between 40-90 mg/kg.

StorageEdit

Acetontrile is very hygroscopic and must be stored in closed bottles. Anhydrous calcium chloride pellets are usually added to keep the solvent dry.

DisposalEdit

Acetonitrile can be neutralized by reacting it with sodium hydroxide, added in excess (for 1 mol MeCN, 2.5 mol NaOH should be added). The byproducts are acetic acid and ammonia.[2]

ReferencesEdit

  1. http://onlinelibrary.wiley.com/doi/10.1002/anie.201302613/abstract
  2. http://link.springer.com/article/10.1007%2FBF02318626

Relevant Sciencemadness threadsEdit

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