Difference between revisions of "Isopropyl nitrate"

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Latest revision as of 22:54, 14 March 2020

Not to be confused with isopropyl nitrite.
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
-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.

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.

Can also be prepared by adding silver nitrate to isopropyl chloride.

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

  1. Gray; Pratt; Journal of the Chemical Society; (1957); p. 2163-2167
  2. http://www.intdetsymp.org/detsymp2002/PaperSubmit/FinalManuscript/pdf/Zhang-131.pdf

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