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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 396342449 |
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| Watchedfields = changed |
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| ImageFile=Diisopropyl_ether_chemical_structure.svg |
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| verifiedrevid = 419351384 |
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| Section1 = {{Chembox Identifiers |
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| ImageFile = Diisopropyl ether.svg |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = 2-propane <!-- corrected; see also https://www.qmul.ac.uk/sbcs/iupac/bibliog/BBerrors.html --> |
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| OtherNames = Isopropyl ether<br />2-Isopropoxypropane<br />Diisopropyl oxide<br />DIPE |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7626 |
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| ChemSpiderID = 7626 |
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| InChI = 1/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3 |
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| InChI = 1/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3 |
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| InChIKey = ZAFNJMIOTHYJRJ-UHFFFAOYAC |
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| InChIKey = ZAFNJMIOTHYJRJ-UHFFFAOYAC |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZAFNJMIOTHYJRJ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=108-20-3 |
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| CASNo=108-20-3 |
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| PubChem = 7914 |
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| SMILES = O(C(C)C)C(C)C |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = DO7Y998826 |
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| EC_number = 203-560-6 |
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| RTECS = TZ5425000 |
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| UNNumber = 1159 |
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| ChEMBL = 3185565 |
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| StdInChI=1S/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3 |
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| StdInChIKey = ZAFNJMIOTHYJRJ-UHFFFAOYSA-N |
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| SMILES = O(C(C)C)C(C)C |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6 | H=14 | O=1 |
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| Formula=C<sub>6</sub>H<sub>14</sub>O |
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| MolarMass=102.18 g/mol |
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| Density=0.725 g/ml |
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| Appearance=Colorless liquid |
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| Density=0.725 g/ml |
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| Odor=Sharp, sweet, ether-like<ref name=NIOSH/> |
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| MeltingPt=−60 °C |
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| MeltingPtC=−60 |
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| BoilingPt=69 °C |
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| Solubility = 2 g/L at 20 °C |
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| BoilingPtC=68.5 |
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| VaporPressure = 119 mmHg (20°C)<ref name=NIOSH/> |
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| MagSus = -79.4·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section7={{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| NFPA-H=1 |
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| EUClass=Flammable ('''F''') |
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| NFPA-F=3 |
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| EUIndex=603-045-00-X |
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| NFPA-H=1 |
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| NFPA-R=1 |
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| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} |
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| NFPA-F=3 |
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| GHSSignalWord = Danger |
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| NFPA-R=1 |
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| HPhrases = {{H-phrases|225|316|319|335|336|361|371|412}} |
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| RPhrases={{R11}}, {{R19}}, {{R66}}, {{R67}} |
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| 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}} |
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| SPhrases={{S2}}, {{S9}}, {{S16}}, {{S29}}, {{S33}} |
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| FlashPtC = −28 |
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| FlashPt=−28 °C |
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| AutoignitionPtC = 443 |
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| Autoignition=443 °C |
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| ExploLimits=1.4–7.9% |
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| ExploLimits=1.4–7.9% |
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| PEL = TWA 500 ppm (2100 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0362}}</ref> |
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| IDLH = 1400 ppm<ref name=NIOSH/> |
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| REL = TWA 500 ppm (2100 mg/m<sup>3</sup>)<ref name=NIOSH/> |
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| LC50 = 38,138 ppm (rat)<br/>30,840 ppm (rabbit)<br/>28,486 ppm (rabbit)<ref name=IDLH>{{IDLH|108203|Isopropyl ether}}</ref> |
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| LD50 = 8470 mg/kg (rat, oral)<ref name=IDLH/> |
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| LDLo = 5000-6500 mg/kg (rabbit, oral)<ref name=IDLH/> |
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'''Diisopropyl ether''' is secondary ] that is used as a ]. It is a colorless liquid that is slightly soluble in water, but miscible with most organic solvents. It is also used as an ] ]. |
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'''Diisopropyl ether''' is a secondary ] that is used as a ]. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an ] ]. It is obtained industrially as a byproduct in the production of ] by ] of ].<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. |
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==Uses== |
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Diisopropyl ether is sometimes represented by the abbreviation "DIPE". |
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Whereas at 20 °C, ] 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 ]. |
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In the laboratory, diisopropyl ether is useful for ]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 }}</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> |
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==Safety== |
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==Safety== |
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Diisopropyl ether tends to form explosive ] upon standing in air for long periods (years). This reaction proceeds more easily than for ], due to the secondary carbon next to the oxygen atom, which makes storage of diisopropyl ether more dangerous. 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<ref name="OSH Answers: Organic peroxides">http://www.ccohs.ca/oshanswers/chemicals/organic/organic_peroxide.html</ref>). For safety reasons, ] is often used as an alternative solvent. |
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Diisopropyl ether forms explosive ] upon standing in air. This reaction proceeds more easily than for ] 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 ] or ].<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, ] is often used as an alternative solvent. |
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== See also == |
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==External links== |
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*{{ICSC|0906|09}} |
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*{{ecb}} |
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==References== |
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==References== |
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==External links== |
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*{{ICSC|0906|09}} |
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