Hexafluoroacetone

Last updated
Hexafluoroacetone
Hexafluoraceton.svg
Hexafluoroacetone 3D.png
Names
Preferred IUPAC name
1,1,1,3,3,3-Hexafluoropropan-2-one
Other names
perfluoroacetone
acetone hexafluoride
perfluoro-2-propanone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.616 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-676-3
PubChem CID
RTECS number
  • UC2450000
UNII
UN number 2420
  • InChI=1S/C3F6O/c4-2(5,6)1(10)3(7,8)9 Yes check.svgY
    Key: VBZWSGALLODQNC-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3F6O/c4-2(5,6)1(10)3(7,8)9
    Key: VBZWSGALLODQNC-UHFFFAOYAI
  • FC(F)(F)C(=O)C(F)(F)F
Properties
C3F6O
Molar mass 166.02 g/mol
AppearanceColorless gas
Odor musty [1]
Density 1.32 g/ml, liquid
Melting point −129 °C (144 K)
Boiling point −28 °C (245 K)
Reacts with water
Vapor pressure 5.8 atm (20 °C) [1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic (T),
Corrosive (C)
GHS labelling:
GHS-pictogram-bottle.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H280, H301, H310, H311, H314, H315, H330, H360, H370, H372
P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P403+P233, P405, P410+P403, P501
NFPA 704 (fire diamond)
3
0
2
W
Flash point Nonflammable [1]
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
TWA 0.1 ppm (0.7 mg/m3) [skin] [1]
IDLH (Immediate danger)
N.D. [1]
Related compounds
Related ketones;
organofluorides
 Acetone;
Hexafluoro-2-propanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Hexafluoroacetone (HFA) is a chemical compound with the formula (CF3)2CO. It is structurally similar to acetone; however, its reactivity is markedly different. It a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a musty odour. [2] The most common form of this substance is hexafluoroacetone sesquihydrate (1.5 H2O), which is a hemihydrate of hexafluoropropane-2,2-diol (F
3C)
2C(OH)
2, a geminal diol.

Contents

Synthesis

The industrial route to HFA involves treatment of hexachloroacetone with HF: [3]

(CCl3)2CO + 6 HF → (CF3)2CO + 6 HCl

Hexafluoropropylene oxide rearranges to give HFA.

In the laboratory, HFA can be prepared in a two step process from perfluoropropene. In the first step KF catalyzes the reaction of the alkene with elemental sulfur to give the 1,3-dithietane [(CF3)2CS]2. This species is then oxidized by iodate to give (CF3)2CO. [4]

Uses

Hexafluoroacetone is used in the production of hexafluoroisopropanol:

(CF3)2CO + H2 → (CF3)2CHOH

It is also used as a precursor to hexafluoroisobutylene, [3] a monomer used in polymer chemistry, and as a building block in the synthesis of midaflur, bisphenol AF, 4,4′-(hexafluoroisopropylidene)diphthalic anhydride, and alitame.

Reactivity

Hexafluoroacetone is an electrophile. Nucleophiles attack at the carbonyl carbon. In water, hexafluoroacetone predominantly exists as the hydrate. The equilibrium constant (Keq) for the formation of this geminal diol is 106 M−1. The analogous equilibrium for acetone is an unfavorable 10−3 M−1. [5] Hexafluoroacetone-hydrates are acidic. In an analogous reaction, ammonia adds to hexafluoroacetone to give the hemiaminal (CF3)2C(OH)(NH2) which can be dehydrated with phosphoryl chloride to give the imine (CF3)2CNH. [6]

Hexafluoroacetone imine is an unusual primary ketimine that is isolable. Hexafluoroacetone imine.svg
Hexafluoroacetone imine is an unusual primary ketimine that is isolable.
Ammonia adduct of hexafluoroacetone CF3-stabilizedHemiaminal.svg
Ammonia adduct of hexafluoroacetone

See also

Related Research Articles

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is a functional group with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Ketene</span> Organic compound of the form >C=C=O

In organic chemistry, a ketene is an organic compound of the form RR'C=C=O, where R and R' are two arbitrary monovalent chemical groups. The name may also refer to the specific compound ethenone H2C=C=O, the simplest ketene.

<span class="mw-page-title-main">Potassium hydroxide</span> Inorganic compound (KOH)

Potassium hydroxide is an inorganic compound with the formula KOH, and is commonly called caustic potash.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.

<span class="mw-page-title-main">Imine</span> Organic compound or functional group containing a C=N bond

In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

<span class="mw-page-title-main">Diazomethane</span> Simplest diazo compound and methylating agent

Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.

<span class="mw-page-title-main">Propyne</span> Hydrocarbon compound (HC≡C–CH3)

Propyne (methylacetylene) is an alkyne with the chemical formula CH3C≡CH. It is a component of MAPD gas—along with its isomer propadiene (allene), which was commonly used in gas welding. Unlike acetylene, propyne can be safely condensed.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

<span class="mw-page-title-main">Chromium(III) chloride</span> Chemical compound

Chromium(III) chloride (also called chromic chloride) describes any of several chemical compounds with the formula CrCl3 · xH2O, where x can be 0, 5, and 6. The anhydrous compound with the formula CrCl3 is a violet solid. The most common form of the trichloride is the dark green hexahydrate, CrCl3 · 6 H2O. Chromium chlorides find use as catalysts and as precursors to dyes for wool.

<span class="mw-page-title-main">Hemiaminal</span> Organic compound or group with a hydroxyl and amine attached to the same carbon

In organic chemistry, a hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: −C(OH)(NR2)−. R can be hydrogen or an alkyl group. Hemiaminals are intermediates in imine formation from an amine and a carbonyl by alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols.

<span class="mw-page-title-main">Methyl methacrylate</span> Chemical compound

Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Mesityl oxide</span> Chemical compound

Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.

<span class="mw-page-title-main">Geminal diol</span>

A geminal diol is any organic compound having two hydroxyl functional groups (-OH) bound to the same carbon atom. Geminal diols are a subclass of the diols, which in turn are a special class of alcohols. Most of the geminal diols are considered unstable.

<span class="mw-page-title-main">Sulfur tetrafluoride</span> Chemical compound

Sulfur tetrafluoride is the chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

<span class="mw-page-title-main">Propargyl alcohol</span> Chemical compound

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

<span class="mw-page-title-main">Diacetone alcohol</span> Chemical compound

Diacetone alcohol is an organic compound with the formula CH3C(O)CH2C(OH)(CH3)2, sometimes called DAA. This colorless liquid is a common synthetic intermediate used for the preparation of other compounds, and is also used as a solvent.

Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.

Methanediol, also known as formaldehyde monohydrate or methylene glycol, is an organic compound with chemical formula CH2(OH)2. It is the simplest geminal diol. In aqueous solutions it coexists with oligomers. The compound is closely related and convertible to the industrially significant derivatives paraformaldehyde, formaldehyde, and 1,3,5-trioxane.

<span class="mw-page-title-main">Chloroacetaldehyde</span> Chemical compound

Chloroacetaldehyde is an organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hemiacetal (ClCH2CH(OH))2O.

<span class="mw-page-title-main">Acetone imine</span> Chemical compound

Acetone imine, or 2-propanimine is an organic compound and an imine with the chemical formula (CH3)2CNH. It is a volatile and flammable liquid at room temperature. It is the simplest ketimine. This compound is mainly of academic interest.

References

  1. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0319". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ CDC - NIOSH Pocket Guide to Chemical Hazards
  3. 1 2 Günter Siegemund; Werner Schwertfeger; Andrew Feiring; Bruce Smart; Fred Behr; Herward Vogel; Blaine McKusick (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349.
  4. ↑ Van Der Puy, M.; Anello, L. G. (1990). "Hexafluoroacetone". Organic Syntheses .; Collective Volume, vol. 7, p. 251
  5. ↑ Lemal, David M. (2004). "Perspective on Fluorocarbon Chemistry". The Journal of Organic Chemistry. 69 (1): 1–11. doi:10.1021/jo0302556. PMID   14703372.
  6. ↑ W. J. Middleton; H. D. Carlson (1970). "Hexafluoroacetone imine". Org. Syntheses. 50: 81–3. doi:10.15227/orgsyn.050.0081..
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.