Diisopropyl ether

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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
EC Number
  • 203-560-6
RTECS number
  • TZ5425000
UNII
UN number 1159
  • InChI=1S/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3 checkY
    Key: ZAFNJMIOTHYJRJ-UHFFFAOYSA-N checkY
  • 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
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)
2 g/L at 20 °C
Vapor pressure 119 mmHg (20°C)[1]
-79.4·10−6 cm3/mol
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
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)
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).
☒N verify (what is checkY☒N ?)

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 propylene.[3] Diisopropyl ether is sometimes represented by the abbreviation DIPE.

Uses

Whereas at 20 °C, diethyl ether will dissolve 1% by weight water, diisopropyl ether only 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. It has also been used as an antiknock agent.

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

See also

References

  1. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0362". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b c "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.
  4. ^ a b 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.

External links

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