| Revision as of 16:23, 12 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 15:37, 6 November 2024 edit undo71.162.221.204 (talk) corrected manufacturer name. DuPont spun off Chemours. Chemours manufacturers HFPO. |
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{{Chembox |
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| verifiedrevid = 316524128 |
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| verifiedrevid = 428777059 |
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| ImageFile = HFPO.png |
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| ImageFile = HFPO.png |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageFile2 = Hexafluoropropylene oxide 3D BS.png |
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| ImageSize2 = 150px |
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| IUPACName = 2,2,3-Trifluoro-3-(trifluoromethyl)oxirane |
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| IUPACName = 2,2,3-Trifluoro-3-(trifluoromethyl)oxirane |
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| OtherNames = trifluoro(trifluoromethyl)oxirane |
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| OtherNames = trifluoro(trifluoromethyl)oxirane |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = HFPO |
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| Abbreviations = HFPO |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 428-59-1 |
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| CASNo = 428-59-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = JPY12AP87N |
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| PubChem = 9883 |
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| PubChem = 9883 |
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| SMILES = C1(C(O1)(F)F)(C(F)(F)F)F |
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| SMILES = C1(C(O1)(F)F)(C(F)(F)F)F |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 9499 |
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| Section2 = {{Chembox Properties |
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| SMILES2 = FC(F)(F)C1(F)OC1(F)F |
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| InChI = 1/C3F6O/c4-1(2(5,6)7)3(8,9)10-1 |
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| InChIKey = PGFXOWRDDHCDTE-UHFFFAOYAQ |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C3F6O/c4-1(2(5,6)7)3(8,9)10-1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = PGFXOWRDDHCDTE-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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| Formula = C<sub>3</sub>F<sub>6</sub>O |
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| Formula = C<sub>3</sub>F<sub>6</sub>O |
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| MolarMass = 166.02 g/mol |
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| MolarMass = 166.02 g/mol |
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| Appearance = colourless gas |
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| Appearance = colourless gas |
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| Density = |
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| Density = 1300kg/m3 at 25 °C |
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| MeltingPt = |
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| MeltingPtC = -144 |
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| BoilingPt = -27.4 |
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| BoilingPtC = -27.4 |
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| Solubility = nonpolar solvents |
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| SolubleOther = nonpolar solvents |
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| VaporPressure = 660kPa at 25 °C |
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| Section3 = {{Chembox Hazards |
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'''Hexafluoropropylene oxide''' (HFPO) is an intermediate used in industrial ]; specifically it is a monomer for ]s. This colourless gas is the ] of ], that is fluorinated analog of ], HFPO is produced by ] and ] and as a precursor to the lubricant ] and related materials. It is generated by oxidation of perfluoropropylene, e.g. with oxygen as well as other oxidants.<ref>Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. {{DOI|10.1002/14356007.a11_349}}</ref> |
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'''Hexafluoropropylene oxide''' (HFPO) is an intermediate used in industrial ]; specifically it is a monomer for ]s. This colourless gas is the ] of ], which is a fluorinated analog of ], HFPO is produced by ] and ] and as a precursor to the lubricant ] and related materials. It is generated by oxidation of perfluoropropylene, e.g. with oxygen as well as other oxidants.<ref>{{Cite book |last1=Siegemund |first1=Günter| chapter=Fluorine Compounds, Organic |last2=Schwertfeger |first2=Werner |last3=Feiring |first3=Andrew |last4=Smart |first4=Bruce |last5=Behr |first5=Fred |last6=Vogel |first6=Herward |last7=McKusick |first7=Blaine |last8=Kirsch |first8=Peer |date=2016-01-28 |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |isbn=978-3-527-30673-2 |location=Weinheim, Germany |pages=1–56 |language=en |doi=10.1002/14356007.a11_349.pub2|title=Ullmann's Encyclopedia of Chemical Technology}}</ref> |
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==Reactivity== |
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==Reactivity== |
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Fluoride catalyzes the formation of the perfluorinated polyethers. The initial step entails ] at the middle carbon to give the perfluoropropoxide anion, which in turn attacks another monomer. This process generates a polymer terminated by an acyl fluoride, which is hydrolyzed to the ] which is decarboxylated with fluorine. The net polymerization reaction can be represented as: |
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Fluoride catalyzes the formation of perfluorinated polyethers such as Krytox. The initial step entails ] at the middle carbon to give the perfluoropropoxide anion, which in turn attacks another monomer. This process generates a polymer terminated by an ], which is hydrolyzed to the ] which is decarboxylated with fluorine.<ref>{{cite web | url=https://cameochemicals.noaa.gov/chemical/844# | title=HEXAFLUOROPROPYLENE OXIDE | CAMEO Chemicals | NOAA }}</ref> The net polymerization reaction can be represented as: |
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:n+2 CF<sub>3</sub>CFCF<sub>2</sub>O → CF<sub>3</sub>CF<sub>2</sub>CF<sub>2</sub>O(CF(CF<sub>3</sub>)CF<sub>2</sub>O)<sub>n</sub>CF<sub>2</sub>CF<sub>3</sub> + CO |
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:n +2 CF<sub>3</sub>CFCF<sub>2</sub>O → CF<sub>3</sub>CF<sub>2</sub>CF<sub>2</sub>O(CF(CF<sub>3</sub>)CF<sub>2</sub>O)<sub>n</sub>CF<sub>2</sub>CF<sub>3</sub> + CO |
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Upon heating above 150 °C, HFPO decomposes to trifluoroacetyl fluoride and ]: |
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Upon heating above 150 °C, HFPO decomposes to trifluoroacetyl fluoride and ]: |
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:CF<sub>3</sub>CFCF<sub>2</sub>O → CF<sub>3</sub>C(O)F + CF<sub>2</sub> |
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:CF3CFCF<sub>2</sub>O → CF<sub>3</sub>C(O)F + CF<sub>2</sub> |
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The epoxide of ] is even more unstable with respect to trifluoracetyl fluoride. |
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The epoxide of ] is even more unstable with respect to trifluoroacetyl fluoride. |
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In the presence of ]s the compound rearranges to ], another important chemical intermediate. |
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In the presence of ]s the compound rearranges to ], another important ]. This rearrangement can be of concern during storage as the rearrangement be catalyzed by the material of the storage cylinder's walls and leads to unwanted formation of HFA during storage. As a result of this, 3M recommends using all HFPO shipped in carbon-steel containers within 90 days of shipping.<ref>https://multimedia.3m.com/mws/mediawebserver?SSSSSuUn_zu8l00xlYtG4x2G4v70k17zHvu9lxtD7SSSSSS {{Bare URL inline|date=August 2024}}</ref> |
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] affords methyl trifluoropyruvate, a reagent useful in organic synthesis:<ref>{{cite encyclopedia|title=Methyltrifluoropyruvate|author=Ruth Figueroa |author2=Richard P. Hsung |author3=Gang Li |author4=Jin Haek Yang |year=2007|doi=10.1002/047084289X.rn00769|publisher=John Wiley & Sons|encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis|isbn=978-0-471-93623-7 }}</ref> |
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:CF<sub>3</sub>CFCF<sub>2</sub>O + 2 ] → CF<sub>3</sub>C(O)CO<sub>2</sub>Me + MeF + 2 HF |
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==References== |
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==References== |
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== External links == |
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