From Wikipedia, the free encyclopedia
Hexafluoropropylene oxide
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Names
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IUPAC name
2,2,3-Trifluoro-3-(trifluoromethyl)oxirane
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Other names
trifluoro(trifluoromethyl)oxirane
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Identifiers
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Abbreviations
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HFPO
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ChemSpider
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ECHA InfoCard
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100.006.411
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UNII
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InChI=1S/C3F6O/c4-1(2(5,6)7)3(8,9)10-1
N
Key: PGFXOWRDDHCDTE-UHFFFAOYSA-N
N
InChI=1/C3F6O/c4-1(2(5,6)7)3(8,9)10-1
Key: PGFXOWRDDHCDTE-UHFFFAOYAQ
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C1(C(O1)(F)F)(C(F)(F)F)F
FC(F)(F)C1(F)OC1(F)F
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Properties
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C
3
F
6
O
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Molar mass
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166.02 g/mol
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Appearance
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colourless gas
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Density
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1300kg/m3 at 25 °C
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Melting point
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?144 °C (?227 °F; 129 K)
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Boiling point
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?27.4 °C (?17.3 °F; 245.8 K)
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Solubility
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nonpolar solvents
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Vapor pressure
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660kPa at 25 °C
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Except where otherwise noted, data are given for materials in their
standard state
(at 25 °C [77 °F], 100 kPa).
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Chemical compound
Hexafluoropropylene oxide
(HFPO) is an intermediate used in industrial
organofluorine chemistry
; specifically it is a monomer for
fluoropolymers
. This colourless gas is the
epoxide
of
hexafluoropropylene
, which is a fluorinated analog of
propylene oxide
, HFPO is produced by
DuPont
and
3M
and as a precursor to the lubricant
Krytox
and related materials. It is generated by oxidation of perfluoropropylene, e.g. with oxygen as well as other oxidants.
[1]
Reactivity
[
edit
]
Fluoride catalyzes the formation of perfluorinated polyethers such as Krytox. The initial step entails
nucleophilic attack
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
carboxylic acid
which is decarboxylated with fluorine.
[2]
The net polymerization reaction can be represented as:
- n +2 CF
3
CFCF
2
O → CF
3
CF
2
CF
2
O(CF(CF
3
)CF
2
O)
n
CF
2
CF
3
+ CO
Upon heating above 150 °C, HFPO decomposes to trifluoroacetyl fluoride and
difluorocarbene
:
- CF3CFCF
2
O → CF
3
C(O)F + CF
2
The epoxide of
tetrafluoroethylene
is even more unstable with respect to trifluoroacetyl fluoride.
In the presence of
Lewis acids
the compound rearranges to
hexafluoroacetone
, another important
chemical intermediate
. 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.
[3]
Methanolysis
affords methyl trifluoropyruvate, a reagent useful in organic synthesis:
[4]
- CF
3
CFCF
2
O + 2
MeOH
→ CF
3
C(O)CO
2
Me + MeF + 2 HF
References
[
edit
]
- ^
Siegemund, Gunter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine; Kirsch, Peer (2016-01-28). Wiley-VCH Verlag GmbH & Co. KGaA (ed.).
Fluorine Compounds, Organic
. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA. pp. 1?56.
doi
:
10.1002/14356007.a11_349.pub2
.
ISBN
978-3-527-30673-2
.
- ^
https://cameochemicals.noaa.gov/chemical/844#
- ^
https://multimedia.3m.com/mws/mediawebserver?SSSSSuUn_zu8l00xlYtG4x2G4v70k17zHvu9lxtD7SSSSSS
- ^
Ruth Figueroa; Richard P. Hsung; Gang Li; Jin Haek Yang (2007). "Methyltrifluoropyruvate".
e-EROS Encyclopedia of Reagents for Organic Synthesis
. John Wiley & Sons.
doi
:
10.1002/047084289X.rn00769
.
ISBN
978-0-471-93623-7
.
External links
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]