Acetyl fluoride

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Acetyl fluoride
Acetylfluorid.svg
Acetyl-Fluoride-3D-balls-by-AHRLS-2012.png
Names
Preferred IUPAC name
Acetyl fluoride
Systematic IUPAC name
Ethanoyl fluoride
Other names
Methylcarbonyl fluoride
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.354 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • Key: JUCMRTZQCZRJDC-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/C2H3FO/c1-2(3)4/h1H3
  • FC(=O)C
Properties
C2H3FO
Molar mass 62.043 g·mol−1
Density 1.032 g/cm3
Melting point −84 °C (−119 °F; 189 K)
Boiling point 21 °C (70 °F; 294 K) [1]
Hazards
GHS labelling:
GHS-pictogram-acid.svg
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Acetyl fluoride is an acyl halide with the chemical formula CH3COF. [2] The formula is commonly abbreviated AcF.

Contents

Synthesis

Acetyl fluoride is synthesized using hydrogen fluoride and acetic anhydride. Acetic acid is produced as a byproduct. [3]

HF + (CH
3
CO)
2
O
CH
3
CO
2
H
+ CH
3
COF

See also

Related Research Articles

Acetyl group Chemical compound

In organic chemistry, acetyl is a moiety, the acyl with chemical formula CH3CO. It is sometimes represented by the symbol Ac (not to be confused with the element actinium).

Acetate Chemical compound

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

Chloroacetic acid Chemical compound

Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.

In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

Acyl halide Chemical compound

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

Acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl functional group into a chemical compound. Such compounds are termed acetate esters or acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

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

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

Acetic anhydride Chemical compound

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.

Acetyl chloride Chemical compound

Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.

The Monsanto process is an industrial method for the manufacture of acetic acid by catalytic carbonylation of methanol. The Monsanto process has largely been supplanted by the Cativa process, a similar iridium-based process developed by BP Chemicals Ltd which is more economical and environmentally friendly.

Cativa process

The Cativa process is a method for the production of acetic acid by the carbonylation of methanol. The technology, which is similar to the Monsanto process, was developed by BP Chemicals and is under license by BP Plc. The process is based on an iridium-containing catalyst, such as the complex [Ir(CO)2I2] (1).

Trifluoroacetic acid Chemical compound

Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CF3CO2H. It is a structural analogue of acetic acid with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar-like odor.

Iron(II) acetate Chemical compound

Iron(II) acetate is a coordination complex with formula Fe(O2CCH3)2. It is a white solid, although impure samples can be slightly colored. A light green tetrahydrate is also known, which is highly soluble in water.

Peracetic acid (also known as peroxyacetic acid, or PAA) is an organic compound with the formula CH3CO3H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive.

Carbonyl fluoride is a chemical compound with the formula COF2. It is a carbon oxohalide. This gas, like its analog phosgene, is colourless and highly toxic. The molecule is planar with C2v symmetry, bond lengths of 1.174 Å (C=O) and 1.312 Å (C–F), and an F–C–F bond angle of 108.0°.

Acetyl iodide is an organoiodine compound with the formula CH3COI. It is a colourless liquid. It is formally derived from acetic acid. Although far rarer in the laboratory than the related acetyl bromide and acetyl chloride, acetyl iodide is produced, transiently at least, on a far larger scale than any other acid halide. Specifically, it is generated by the carbonylation of methyl iodide in the Cativa and Monsanto processes that are the main industrial route to acetic acid. It is also an intermediate in the production of acetic anhydride from methyl acetate.

Acetic acid Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

Acetic formic anhydride Chemical compound

Acetic formic anhydride is an organic compound with the chemical formula C
3
H
4
O
3
and a structural formula of H
3
C
-(C=O)-O-(C=O)H. It can be viewed as the mixed anhydride of acetic acid and formic acid.

Acetyl nitrate Chemical compound

Acetyl nitrate is the organic compound with the formula CH3C(O)ONO2. It is classified as the mixed anhydride of nitric and acetic acids. It is a colorless explosive liquid that fumes in moist air.

Lutetium(III) acetate Compound of lutetium

Lutetium(III) acetate is the acetate salt of lutetium with the chemical formula of Lu(CH3COO)3.

References

  1. "Acetyl fluoride". Archived from the original on 2014-03-28. Retrieved 2012-03-07.
  2. "Acetyl Fluoride". NIST. Archived from the original on 21 February 2019. Retrieved 7 March 2012.
  3. Tanaka, Mutsuo; Fujiwara, Masahiro; Ando, Hisanori (1995). "Dual Reactivity of the Formyl Cation as an Electrophile and a Bransted Acid in Superacids". Journal of Organic Chemistry. 60 (12): 3846–3850. doi:10.1021/jo00117a041.