Acetyl iodide

Acetyl iodide
Skeletal formula of acetyl iodide
Skeletal formula of acetyl iodide
Spacefill model of acetyl iodide
Spacefill model of acetyl iodide
Names
Preferred IUPAC name
Acetyl iodide[1]
Systematic IUPAC name
Ethanoyl iodide
Identifiers
CAS Number
  • 507-02-8 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 10051 checkY
ECHA InfoCard 100.007.330 Edit this at Wikidata
EC Number
  • 208-062-2
PubChem CID
  • 10483
UNII
  • JAL3KV9I1O checkY
UN number 1898
CompTox Dashboard (EPA)
  • DTXSID0060141 Edit this at Wikidata
InChI
  • InChI=1S/C2H3IO/c1-2(3)4/h1H3 checkY
    Key: LEKJTGQWLAUGQA-UHFFFAOYSA-N checkY
  • InChI=1/C2H3IO/c1-2(3)4/h1H3
    Key: LEKJTGQWLAUGQA-UHFFFAOYAR
  • CC(I)=O
Properties
Chemical formula
 C2H3IO
Molar mass 169.949 g·mol−1
Boiling point 108 °C; 226 °F; 381 K
Solubility in water
 Decomposes
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298)
 -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
Chemical compound

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, which are the main industrial processes that generate 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]

CH3COI + RCO2H → CH3CO2H + RCOI

References

  1. ^ "ACETYL IODIDE - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. ^ Jones, J. H. (2000). "The Cativa Process for the Manufacture of Acetic Acid" (PDF). Platinum Metals Rev. 44 (3): 94–105. Archived from the original (PDF) on 2015-09-24. Retrieved 2011-07-03.
  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. S2CID 97920158.