Diisopropyl ether

Last updated
Diisopropyl ether
Diisopropyl ether.svg
Names
Preferred IUPAC name
2-[(Propan-2-yl)oxy]propane
Other names
Isopropyl ether
2-Isopropoxypropane
Diisopropyl oxide
DIPE
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.237 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-560-6
PubChem CID
RTECS number
  • TZ5425000
UNII
UN number 1159
  • InChI=1S/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3 Yes check.svgY
    Key: ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3
    Key: ZAFNJMIOTHYJRJ-UHFFFAOYAC
  • O(C(C)C)C(C)C
Properties
C6H14O
Molar mass 102.177 g·mol−1
AppearanceColorless 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)
2 g/L at 20 °C
Vapor pressure 119 mmHg (20°C) [1]
−79.4·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H225, H316, H319, H335, H336, H361, H371, H412
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P309+P311, P312, P332+P313, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
3
1
Flash point −28 °C (−18 °F; 245 K)
443 °C (829 °F; 716 K)
Explosive limits 1.4–7.9%
Lethal dose or concentration (LD, LC):
8470 mg/kg (rat, oral) [2]
5000-6500 mg/kg (rabbit, oral) [2]
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Diisopropyl ether is a 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 also used as an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. [3] Diisopropyl ether is sometimes represented by the abbreviation DIPE.

Contents

Use as a solvent

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

In the laboratory, diisopropyl ether is useful for recrystallizations because it has a wide liquid range. [4] [5] Diisopropyl ether is used for converting bromoboranes, which are thermally labile, into isopropoxy derivatives. [6]

Safety

Diisopropyl ether forms explosive organic peroxides similar to TATP upon standing in air. This reaction proceeds more easily than for diethyl ether due to the increased lability of the C-H bond adjacent to oxygen. Many explosions have been known to occur during handling of old diisopropyl ether bottles. [7] Some laboratory procedures recommend use of freshly opened bottles. [4] Antioxidants such as butylated hydroxytoluene can be used to prevent this process. The stored solvent is generally tested for the presence of peroxides. It is recommended to test once every 3 months for diisopropyl ether compared to once every 12 months for diethyl ether. [8] Peroxides may be removed by stirring the ether with an aqueous solution of iron(II) sulfate (green vitriol) or sodium metabisulfite. [9] [10] For safety reasons, methyl tert-butyl ether is often used as an alternative solvent.

See also

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0362". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 "Isopropyl ether". Immediately Dangerous to Life or 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. ISBN   978-3-527-30673-2.
  4. 1 2 Andrea Goti; Francesca Cardona; Gianluca Soldaini (2005). "Methyltrioxorhenium Catalyzed Oxidation of Secondary Amines to Nitrones: N-Benzylidene-Benzylamine N-Oxide". Organic Syntheses. 81: 204. doi: 10.15227/orgsyn.081.0204 .
  5. ↑ Ferenc Merényi, Martin Nilsson (1972). "2-Acetyl-1,3-Cyclopentanedione". Organic Syntheses. 52: 1. doi:10.15227/orgsyn.052.0001.
  6. ↑ Shoji Hara, Akira Suzuk (1998). "Synthesis of 4-(2-Bromo-2-Propenyl)-4-Methyl-Y-Butyrolactone by the Reaction of Ethyl Levulinate with (2-Bromoallyl)Diisopropoxyborane Prepared by Haloboration of Allene". Organic Syntheses. 75: 129. doi:10.15227/orgsyn.075.0129.
  7. ↑ Matyáš, Robert; Pachman, Jiří. (2013). Primary explosives. Berlin: Springer. p. 272. ISBN   978-3-642-28436-6. OCLC   832350093.
  8. ↑ "Organic Peroxides - Hazards : OSH Answers". www.ccohs.ca. Canadian Centre for Occupational Health and Safety, Government of Canada.
  9. ↑ Chai, Christina Li Lin; Armarego, W. L. F. (2003). Purification of laboratory chemicals. Oxford: Butterworth-Heinemann. p. 176. ISBN   978-0-7506-7571-0.
  10. ↑ Hamstead, A. C. (1964). "Destroying Peroxides of Isopropyl Ether". Industrial and Engineering Chemistry. 56 (6): 37-42. doi:10.1021/ie50654a005.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.