:Diisopropyl ether
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 419351384
| ImageFile = Diisopropyl ether.svg
| PIN = 2-[(Propan-2-yl)oxy]propane
| OtherNames = Isopropyl ether
2-Isopropoxypropane
Diisopropyl oxide
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
| MeltingPtC=−60
| Solubility = 2 g/L at 20 °C
| BoilingPtC=68.5
| VaporPressure = 119 mmHg (20°C)
| MagSus = −79.4·10−6 cm3/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=1.4–7.9%
| PEL = TWA 500 ppm (2100 mg/m3){{PGCH|0362}}
| REL = TWA 500 ppm (2100 mg/m3)
| LC50 = 38,138 ppm (rat)
30,840 ppm (rabbit)
28,486 ppm (rabbit){{IDLH|108203|Isopropyl ether}}
| LD50 = 8470 mg/kg (rat, oral)
| LDLo = 5000-6500 mg/kg (rabbit, oral)
}}
}}
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 of propylene.{{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}} 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 recrystallizations because it has a wide liquid range.{{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 }}{{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 }} Diisopropyl ether is used for converting bromoboranes, which are thermally labile, into isopropoxy derivatives.{{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 }}
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.{{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}} Some laboratory procedures recommend use of freshly opened bottles. 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.{{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 }} Peroxides may be removed by shaking the ether with an aqueous solution of iron(II) sulfate or sodium metabisulfite.{{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}}{{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}} For safety reasons, methyl tert-butyl ether is often used as an alternative solvent.
See also
References
{{Reflist}}