Difference between revisions of "Acetonitrile"
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| − | '''Acetonitrile''', also known as '''cyanomethane''', '''ethanenitrile''' or '''methyl cyanide''' is a chemical compound | + | '''Acetonitrile''', also known as '''cyanomethane''', '''ethanenitrile''' or '''methyl cyanide''' is a organic chemical compound, mainly used as a solvent in chemistry. It has the formula CH<sub>3</sub>CN. |
==Properties== | ==Properties== | ||
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:PdCl<sub>2</sub> + 2 CH<sub>3</sub>CN → PdCl<sub>2</sub>[CH<sub>3</sub>CN]<sub>2</sub> | :PdCl<sub>2</sub> + 2 CH<sub>3</sub>CN → PdCl<sub>2</sub>[CH<sub>3</sub>CN]<sub>2</sub> | ||
| + | |||
| + | Pyrolysis of acetonitrile yields carbon dioxide, water and hydrogen cyanide. | ||
===Physical=== | ===Physical=== | ||
| − | 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. | + | 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 over time. It has a melting point between −46 to −44 °C and a boiling point between 81.3 to 82.1 °C. |
==Availability== | ==Availability== | ||
| − | Acetonitrile can be purchased from chemical suppliers. [http://www.sciencestuff.com/prod/Chem-Rgnts/C1147 ScienceStuff] sells 1 liter at $76.88 + UPS hazardous material surcharge of $28.50 per shipment. | + | Acetonitrile can be purchased from chemical suppliers. [http://www.sciencestuff.com/prod/Chem-Rgnts/C1147 ScienceStuff] sells 1 liter at $76.88 + UPS hazardous material surcharge of $28.50 per shipment. In most places it's difficult to acquire due to being a cyanide compound. |
==Preparation== | ==Preparation== | ||
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[[Category:Solvents]] | [[Category:Solvents]] | ||
[[Category:Nitriles]] | [[Category:Nitriles]] | ||
| + | [[Category:Contact poisons]] | ||
Revision as of 17:48, 18 November 2015
Acetonitrile, also known as cyanomethane, ethanenitrile or methyl cyanide is a organic chemical compound, mainly used as a solvent in chemistry. It has the formula CH3CN.
Contents
Properties
Chemical
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
Pyrolysis of acetonitrile yields carbon dioxide, water and hydrogen cyanide.
Physical
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 over time. It has a melting point between −46 to −44 °C and a boiling point between 81.3 to 82.1 °C.
Availability
Acetonitrile can be purchased from chemical suppliers. ScienceStuff sells 1 liter at $76.88 + UPS hazardous material surcharge of $28.50 per shipment. In most places it's difficult to acquire due to being a cyanide compound.
Preparation
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
Projects
- Ethylamine synthesis
Handling
Safety
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. See cyanide for antidotes and methods of treatment.
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.
Storage
Acetontrile is very hygroscopic and must be stored in closed bottles. Anhydrous calcium chloride pellets are usually added to keep the solvent dry.
Disposal
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]
References
- ↑ http://onlinelibrary.wiley.com/doi/10.1002/anie.201302613/abstract
- ↑ http://link.springer.com/article/10.1007%2FBF02318626
