Diisopropyl ether

Diisopropyl ether is secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propene.[3] Diisopropyl ether is sometimes represented by the abbreviation "DIPE".

Diisopropyl ether
Names
Preferred IUPAC name
2-[(Propan-2-yl)oxy]propane
Other names
Isopropyl ether
2-Isopropoxypropane
Diisopropyl oxide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.237
EC Number
  • 203-560-6
PubChem CID
RTECS number
  • TZ5425000
UNII
UN number 1159
CompTox Dashboard (EPA)
Properties
Chemical formula
 C6H14O
Molar mass 102.177 g·mol−1
Appearance Colorless liquid
Odor Sharp, sweet, ether-like[1]
Density 0.725 g/ml
Melting point −60 °C (−76 °F; 213 K)
Boiling point 68.5 °C (155.3 °F; 341.6 K)
Solubility in water
 2 g/L at 20 °C
Vapor pressure 119 mmHg (20°C)[1]
Magnetic susceptibility (χ)
 -79.4·10−6 cm3/mol
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H316, H319, H335, H336, H361, H371, H402, H412
GHS precautionary statements
 P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P303+361+353, P304+340, P305+351+338, P308+313, P309+311, P312, P332+313, P337+313, P370+378
NFPA 704 (fire diamond)
3
1
1
Flash point −28 °C (−18 °F; 245 K)
Autoignition
temperature
 443 °C (829 °F; 716 K)
Explosive limits 1.4–7.9%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 8470 mg/kg (rat, oral)[2]
LDLo (lowest published)
 5000-6500 mg/kg (rabbit, oral)[2]
LC50 (median concentration)
 38,138 ppm (rat)
30,840 ppm (rabbit)
28,486 ppm (rabbit)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 500 ppm (2100 mg/m3)[1]
REL (Recommended)
 TWA 500 ppm (2100 mg/m3)[1]
IDLH (Immediate danger)
 1400 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uses

Whereas at 20 °C, diethyl ether will dissolve 1% by weight water, DIPE only dissolves 0.88%. It is used as a specialized solvent to remove or extract polar organic compounds from aqueous solutions, e.g. phenols, ethanol, acetic acid. DIPE was used as an antiknock agent.

Safety

Diisopropyl ether can form explosive peroxides upon standing in air for long periods. This reaction proceeds more easily than for ethyl ether, due to the secondary carbon next to the oxygen atom. Antioxidants can be used to prevent this process. The stored solvent should therefore be tested for the presence of peroxides more often (recommended once every 3 months for diisopropyl ether vs. once every 12 months for ethyl ether[4]). Peroxides may be removed by shaking the ether with an aqueous solution of iron(II) sulfate or sodium metabisulfite.[5][6] For safety reasons, methyl tert-butyl ether is often used as an alternative solvent.

See also

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0362". National Institute for Occupational Safety and Health (NIOSH).
  2. "Isopropyl ether". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. Sakuth, Michael; Mensing, Thomas; Schuler, Joachim; Heitmann, Wilhelm; Strehlke, Günther; Mayer (2010). "Ethers, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_023.pub2.
  4. http://www.ccohs.ca/oshanswers/chemicals/organic/organic_peroxide.html
  5. Chai, Christina Li Lin; Armarego, W. L. F. (2003). Purification of laboratory chemicals. Oxford: Butterworth-Heinemann. p. 176. ISBN 978-0-7506-7571-0.
  6. Hamstead, A. C. (1964). "Destroying Peroxides of Isopropyl Ether". Industrial and Engineering Chemistry. 56: 37-42. doi:10.1021/ie50654a005.
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