Acetyl iodide
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Acetyl iodide
| Acetyl iodide | |
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Ethanoyl iodide[citation needed] |
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Acetyl iodide[1] |
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| Identifiers | |
| CAS number | 507-02-8  |
| PubChem | 10483 |
| ChemSpider | 10051  |
| EC number | 208-062-2 |
| UN number | 1898 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C2H3OI |
| Molar mass | 169.9491 g mol-1 |
| Exact mass | 169.922858138 g mol-1 |
| Boiling point |
108 °C, 381 K, 226 °F |
| Solubility in water | Decomposes |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
-163.18--161.42 kJ mol-1 |
| Related compounds | |
| Related acyl halides | Acetyl chloride |
| Related compounds | Acetic acid |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Acetyl iodide (IUPAC name: ethanoyl iodide) is an organoiodine compound wth 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 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, say acetyl chloride. Instead acetyl iodide undergoes iodide/hydroxide exchange with most carboxylic acids:[4]
- CH3C(O)I + RCO2H → CH3CO2H + RC(O)I
References
- ^ "ACETYL IODIDE - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10483.
- ^ Jones, J. H. (2000). "The CativaTM Process for the Manufacture of Acetic Acid". Platinum Metals Rev. 44 (3): 94–105. http://www.platinummetalsreview.com/pdf/pmr-v44-i3-094-105.pdf.
- ^ 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
- ^ 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.
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