Acetyl iodide

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Acetyl iodide
Skeletal formula of acetyl iodide
Spacefill model of acetyl iodide
Names
Preferred IUPAC name
Ethanoyl iodide[citation needed]
Systematic IUPAC name
Acetyl iodide[1]
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.007.330
EC Number 208-062-2
UN number 1898
Properties
C2H3IO
Molar mass 169.95 g·mol−1
Boiling point 108 °C; 226 °F; 381 K
Decomposes
Thermochemistry
-163.18--161.42 kJ mol−1
Related compounds
Related acyl halides
Acetyl chloride
Related compounds
Acetic acid

Acetic anhydride

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acetyl iodide is an organoiodine compound with the formula CH3C(O)I. 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.[2] It is also an intermediate in the production of acetic anhydride from methyl acetate.[3]

Upon treatment with carboxylic acids, acetyl iodide does not exhibit reactions typical of acyl halides, such as acetyl chloride. Instead, acetyl iodide undergoes iodide/hydroxide exchange with most carboxylic acids:[4]

CH3C(O)I + RCO2H → CH3CO2H + RC(O)I

References[edit]

  1. ^ "ACETYL IODIDE - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. 
  2. ^ Jones, J. H. (2000). "The CativaTM Process for the Manufacture of Acetic Acid" (PDF). Platinum Metals Rev. 44 (3): 94–105. 
  3. ^ Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. (1992), "Eastman Chemical Company Acetic Anhydride Process", Catal. Today, 13 (1): 73–91, doi:10.1016/0920-5861(92)80188-S 
  4. ^ M. G. Voronkov; L. I. Belousova; A. A. Trukhina; N. N. Vlasova (2003). "Acyl Iodides in Organic Synthesis: IV. Reaction of Acetyl Iodide with Carboxylic Acids". Russian Journal of Organic Chemistry. 39 (12): 1702. doi:10.1023/B:RUJO.0000019730.43667.46.