Difference between revisions of "Formamide"
| Line 116: | Line 116: | ||
:HC(O)NH<sub>2</sub> → CO + NH<sub>3</sub> | :HC(O)NH<sub>2</sub> → CO + NH<sub>3</sub> | ||
| − | If the decomposition occurs in the presence of | + | If the decomposition occurs in the presence of solid acid catalysts, formamide dehydrates to HCN:<ref>https://onlinelibrary.wiley.com/doi/10.1002/14356007.a12_001.pub2/otherversions</ref> |
:HC(O)NH<sub>2</sub> → HCN + H<sub>2</sub>O | :HC(O)NH<sub>2</sub> → HCN + H<sub>2</sub>O | ||
Latest revision as of 20:51, 26 December 2022
| Names | |
|---|---|
| IUPAC name
Formamide
| |
| Preferred IUPAC name
Formamide | |
| Systematic IUPAC name
Methanamide | |
| Other names
Carbamaldehyde
| |
| Properties | |
| CH3NO | |
| Molar mass | 45.04 g/mol |
| Appearance | Colorless liquid |
| Odor | Ammonia-like |
| Density | 1.133 g/cm3 (20 °C) |
| Melting point | 2.55 °C (36.59 °F; 275.70 K) |
| Boiling point | 210 °C (410 °F; 483 K) |
| Miscible | |
| Solubility | Miscible with acetic acid, acetone, chloroform, dichloromethane, diethyl ether, dioxane, ethanol, ethylene glycol, glycerol, isopropanol, methanol, petroleum ether, phenol |
| Vapor pressure | 0.08 mmHg (20 °C) |
| Acidity (pKa) | 23.5 (in DMSO) |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 154 °C (309 °F; 427 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
5.325 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Dimethylformamide Acetamide |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Formamide, also known as methanamide, is an amide derived from formic acid, a clear liquid with an ammonia-like odor.
Contents
Properties
Chemical
Thermal decomposition of formamide at 180 °C yields carbon monoxide and ammonia, as well as traces of hydrogen cyanide.
- HC(O)NH2 → CO + NH3
If the decomposition occurs in the presence of solid acid catalysts, formamide dehydrates to HCN:[1]
- HC(O)NH2 → HCN + H2O
Physical
Formamide is colorless liquid with an ammonia-like odor miscible in water and many organic compounds.
Availability
Formamide is sold by chemical suppliers.
Preparation
Formamide can be prepared from the pyrolysis of ammonium acetate, which in turn is made by neutralizing ammonia with formic acid.
- HCOOH + NH3 → HCOONH4
- HCOONH4 → HCONH2 + H2O
Formamide can also be obtained from the aminolysis of ethyl formate:
- HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH
Projects
- Leuckart reaction
- Make hydrogen cyanide (VERY DANGEROUS!!)
Handling
Safety
Formamide is moderately irritating to the skin, eyes and mucous membranes. Formamide has been shown to exhibit hematoxicity in animals and prolonged exposure via inhalation or dermal absorption is considered hazardous. It is also classified as teratogen. Formamide should never be handled without proper safety attire including gloves and goggles.
Storage
In closed bottles.
Disposal
Should be mixed with a more flammable solvent and incinerated.
