Isopropyl nitrate
| Names | |
|---|---|
| IUPAC name
Propan-2-yl nitrate
| |
| Other names
2-Propyl nitrate
IPN Isonite Nitric acid, 1-methylethyl ester | |
| Properties | |
| C3H7NO3 | |
| Molar mass | 105.09 g/mol |
| Appearance | Colorless liquid |
| Odor | Sweet, pleasant |
| Density | 1.036 g/cm3 (20 °C) |
| Melting point | −82.5 °C (−116.5 °F; 190.7 K) |
| Boiling point | 101.5 °C (214.7 °F; 374.6 K) |
| 0.365 g/100 ml (25 °C) | |
| Vapor pressure | 34.10 mmHg |
| Acidity (pKa) | 16.9 |
| Thermochemistry | |
| Std enthalpy of
formation (ΔfH |
-229.7 kJ/mol |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 22.2 °C (72.0 °F; 295.3 K) |
| Related compounds | |
| Related compounds
|
Ethyl nitrate Propylene glycol dinitrate |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Isopropyl nitrate (IPN) or 2-propyl nitrate is a colorless liquid monopropellant. It is used as a diesel cetane improver.
Contents
Properties
Chemical
Isopropyl nitrate is extremely flammable and burns with a practically invisible flame. The flame is significantly less luminous than hydrogen or methanol flame and is only visible due to the turbulent hot air it generates. This presents unique hazards in its handling.
Physical
Isopropyl nitrate is a colorless liquid, with a pleasant odor. It is immiscible with water, but miscible with many organic solvents.
Explosive
IPN is a low-sensitivity explosive, with a detonation velocity of approximately 5400 m/s.[2]
Availability
Isopropyl nitrate is sold by several chemical suppliers, though it's not easy to acquire.
Preparation
Isopropyl nitrate can be prepared by nitrating dry isopropanol in the presence of urea, using 40% nitric acid.
Direct nitration of isopropyl alcohol is difficult due to oxidation of the secondary carbon atom carrying the hydroxyl group. Simple nitration of isopropanol tends to yield acetone and other side products, which is why urea is used.
Like wise, using fuming nitric acid and sulphuric acid to nitrate isopropanol tends to yield nitroform instead.
One possible route involved reaction of silver nitrate to isopropyl chloride or iodide.
Projects
- Make invisible flame
- Various propellants
Handling
Safety
Isopropyl nitrate, like all nitrate esters, affects blood pressure, causes respiratory toxicity, damages liver and kidneys, distorts vision, causes methoglobinuria, and can cause headache and lack of coordination. It may be absorbed through skin. Its primary toxicity mechanism is methemoglobinemia.
Storage
Should not be kept for long.
Disposal
Dilute it in a solvent, then carefully add a cooled solution of sodium hydroxide.
References
- ↑ Gray; Pratt; Journal of the Chemical Society; (1957); p. 2163-2167
- ↑ http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Zhang-131.pdf
