Ethyl iodide

From Sciencemadness Wiki
Jump to: navigation, search
Ethyl iodide
Names
IUPAC name
Iodoethane
Other names
1-Ethyl iodide
Ethyl iodine
Iodo-ethane
Monoiodoethane
Identifiers
Jmol-3D images Image
Properties
CH3CH2I
Molar mass 155.97 g/mol
Appearance Colorless liquid
Brownish liquid (old sample)
Odor Pungent, ether-like
Density 1.9308 g/cm3 (at 20 °C)[1]
Melting point −111.10 °C (−167.98 °F; 162.05 K)
Boiling point 71.5 to 73.3 °C (160.7 to 163.9 °F; 344.6 to 346.4 K)
4 g/L (at 20 °C)
Solubility Miscible with alcohol, diethyl ether
Vapor pressure 17.7 kPa
Viscosity 5.925 mPa s (at 20 °C)
Hazards
Safety data sheet ScienceLab
Related compounds
Related compounds
Methyl iodide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ethyl iodide or iodoethane is an organic chemical compound of iodine, which appears as a colorless dense liquid (older samples have a brownish or yellowish color), insoluble in water but miscible with other solvents. It has the chemical formula CH3CH2I, sometimes written as EtI.

Properties

Chemical

Like most alkyl iodides, ethyl iodide hydrolyzes in the presence of an alkali:

CH3CH2I + MOH → CH3CH2OH + MI

Physical

Ethyl iodide is a dense, colorless (though old samples have a brownish color) liquid, immiscible in water, but miscible with many solvents such as diethyl ether, ethanol, methanol. Ethyl iodide is toxic and has a strong ether-like odor. It has a density of 1.9308 g/cm3 at 20 °C.

Availability

Ethyl iodide is sold by various chemical suppliers, though it's difficult to acquire by the amateur chemist.

Preparation

Ethyl iodide can be prepared by distilling off a mixture of anhydrous ethanol with hydroiodic acid or hydrogen iodide.

A more direct route involves anhydrous ethanol, red phosphorus and iodine. This reaction forms the unstable phosphorus triiodide, which reacts with ethanol to yield iodoethane:

3 CH3CH2OH + PI3 → 3 CH3CH2I + H3PO3

Projects

  • Make esters
  • Diethyl zinc synthesis

Handling

Safety

Ethyl iodide is toxic and carcinogenic.

Iodoethane MUST be kept away from heavy metals as it reacts to form extremely toxic heavy ethyl iodides, which are more toxic than their corresponding metals. AVOID contact with their amalgam, as this yields their volatile, extremely toxic and quite deadly organometallic derivatives.

Storage

Ethyl iodide must be stored in amber bottles, in dark well ventilated places, away from light. Copper or silver wire can be added as a stabilizer.

Disposal

Ethyl iodide can be hydrolyzed to ethanol with sodium hydroxide, which can be either burned or recycled if necessary.

References

  1. Kibardin, A.M.; Gryaznov, P.I.; Gazizov, T.Kh.; Pudovik, A.N.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2166 - 2168

Relevant Sciencemadness threads