Editing Diisopropyl ether

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 419351384
| ImageFile = Diisopropyl ether.svg
| PIN = 2-[(Propan-2-yl)oxy]propane <!-- corrected; see also https://www.qmul.ac.uk/sbcs/iupac/bibliog/BBerrors.html -->
| OtherNames = Isopropyl ether<br />2-Isopropoxypropane<br />Diisopropyl oxide<br />DIPE
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7626
| InChI = 1/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3
| InChIKey = ZAFNJMIOTHYJRJ-UHFFFAOYAC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=108-20-3
| PubChem = 7914
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DO7Y998826
| EC_number = 203-560-6
| RTECS = TZ5425000
| UNNumber = 1159
| ChEMBL = 3185565
| StdInChI=1S/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3
| StdInChIKey = ZAFNJMIOTHYJRJ-UHFFFAOYSA-N
| SMILES = O(C(C)C)C(C)C
}}
|Section2={{Chembox Properties
| C=6 | H=14 | O=1
| Density=0.725 g/ml
| Appearance=Colorless liquid
| Odor=Sharp, sweet, ether-like<ref name=NIOSH/>
| MeltingPtC=−60
| Solubility = 2 g/L at 20 °C
| BoilingPtC=68.5
| VaporPressure = 119 mmHg (20°C)<ref name=NIOSH/>
| MagSus = −79.4·10<sup>−6</sup> cm<sup>3</sup>/mol
  }}
|Section7={{Chembox Hazards
| NFPA-H=1
| NFPA-F=3
| NFPA-R=1
| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|316|319|335|336|361|371|412}}
| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|261|264|270|271|273|280|281|303+361+353|304+340|305+351+338|308+313|309+311|312|332+313|337+313|370+378|403+233|403+235|405|501}}
| FlashPtC = −28
| AutoignitionPtC = 443
| ExploLimits=1.4&ndash;7.9%
| PEL = TWA 500 ppm (2100 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0362}}</ref>
| IDLH = 1400 ppm<ref name=NIOSH/>
| REL = TWA 500 ppm (2100 mg/m<sup>3</sup>)<ref name=NIOSH/>
| LC50 = 38,138 ppm (rat)<br/>30,840 ppm (rabbit)<br/>28,486 ppm (rabbit)<ref name=IDLH>{{IDLH|108203|Isopropyl ether}}</ref>
| LD50 = 8470 mg/kg (rat, oral)<ref name=IDLH/>
| LDLo = 5000-6500 mg/kg (rabbit, oral)<ref name=IDLH/>
  }}
}}

'''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 used as an extractant and an [[oxygenate]] [[gasoline additive]].  It is obtained industrially as a byproduct in the production of [[isopropanol]] by [[hydration reaction|hydration]] of [[propylene]].<ref name=Ullmann>{{Ullmann|first1=Michael |last1=Sakuth|first2=Thomas |last2=Mensing|first3= Joachim|last3=Schuler|first4=Wilhelm |last4=Heitmann|first5=Günther |last5=Strehlke|first6Dieter |last6=Mayer|title=Ethers, Aliphatic|year=2010|doi=10.1002/14356007.a10_023.pub2}}</ref> Diisopropyl ether is sometimes represented by the abbreviation DIPE.

==Uses==
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. It has also been used as an [[antiknock agent]].

In the laboratory, diisopropyl ether is useful for [[Recrystallization (chemistry)|recrystallization]]s because it has a wide liquid range.<ref name=OS>{{cite journal |doi=10.15227/orgsyn.081.0204|title=Methyltrioxorhenium Catalyzed Oxidation of Secondary Amines to Nitrones: N-Benzylidene-Benzylamine N-Oxide |journal=Organic Syntheses |year=2005 |volume=81 |page=204|author1=Andrea Goti |author2=Francesca Cardona |author3=Gianluca Soldaini |doi-access=free |url=http://www.orgsyn.org/orgsyn/default.asp?dbname=orgsyn&dataaction=search&metadata_directive=blind_gui&formgroup=quick_form_group&Preps.CollVol=11&order_by=Preps.CollPage%20ASC }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.052.0001|title=2-Acetyl-1,3-Cyclopentanedione |journal=Organic Syntheses |year=1972 |volume=52 |page=1|author=Ferenc Merényi, Martin Nilsson }}</ref>  Diisopropyl ether is used for converting bromoboranes, which are thermally labile, into isopropoxy derivatives.<ref>{{cite journal |doi=10.15227/orgsyn.075.0129|title=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 |journal=Organic Syntheses |year=1998 |volume=75 |page=129|author=Shoji Hara, Akira Suzuk }}</ref>

==Safety==
Diisopropyl ether forms explosive [[organic peroxide|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.<ref>{{cite book | last=Matyáš | first=Robert | last2=Pachman | first2=Jiří. | title=Primary explosives | publisher=Springer | publication-place=Berlin | date=2013 | isbn=978-3-642-28436-6 | oclc=832350093 |page=272}}</ref> Some laboratory procedures recommend use of freshly opened bottles.<ref name=OS/> Antioxidants can be used to prevent this process. The stored solvent is generally 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.<ref name="OSH Answers: Organic peroxides">{{Cite web | url=https://www.ccohs.ca | title=Organic Peroxides - Hazards : OSH Answers | publisher = Canadian Centre for Occupational Health and Safety, Government of Canada | website=www.ccohs.ca }}</ref> Peroxides may be removed by shaking the ether with an aqueous solution of [[iron(II) sulfate]] or [[sodium metabisulfite]].<ref>{{cite book |author1=Chai, Christina Li Lin |author2=Armarego, W. L. F. |title=Purification of laboratory chemicals |publisher=Butterworth-Heinemann |location=Oxford |year=2003 |pages= 176|isbn=978-0-7506-7571-0}}</ref><ref>{{cite journal|title=Destroying Peroxides of Isopropyl Ether|last=Hamstead|first=A. C.|journal=Industrial and Engineering Chemistry|year=1964|volume=56|issue=6|page=37-42|doi=10.1021/ie50654a005}}</ref> For safety reasons, [[methyl tert-butyl ether|methyl ''tert''-butyl ether]] is often used as an alternative solvent.

== See also ==
* [[Dimethyl ether]]
* [[Diethyl ether]]
* [[Dipropyl ether]]
* [[Di-tert-butyl ether|Di-''tert''-butyl ether]]
* [[Methyl tert-butyl ether|Methyl ''tert''-butyl ether]]
*[[List of gasoline additives]]

==References==
{{Reflist}}

==External links==
*{{ICSC|0906|09}}

[[Category:Dialkyl ethers]]
[[Category:Ether solvents]]
[[Category:Oxygenates]]
[[Category:Isopropyl compounds]]
[[Category:Symmetrical ethers]]
[[Category:Sweet-smelling chemicals]]