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Hydroiodic acid

From Wikipedia, the free encyclopedia
Aqueous solution of hydrogen iodide
Hydroiodic acid
Space-filling model of hydrogen iodide
Space-filling model of hydrogen iodide
Space-filling model of water
Space-filling model of water
The iodide anion
The iodide anion
Space-filling model of the hydronium cation
Space-filling model of the hydronium cation
An oxidized solution of hydroiodic acid
An oxidized solution of hydroiodic acid
Names
Other names
  • Aqueous hydrogen iodide
  • Hydriodic acid
  • Hydrogen iodide, hydrous
  • Hydronium iodide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 233-109-9
RTECS number
  • MW3760000
UNII
  • InChI=1S/BrH/h1H checkY
    Key: CPELXLSAUQHCOX-UHFFFAOYSA-N checkY
  • InChI=1/BrH/h1H
    Key: CPELXLSAUQHCOX-UHFFFAOYAZ
  • [OH3+].[I-]
Properties
HI(aq)
Molar mass127.912 g·mol−1 (HI)
Appearancecolorless liquid when pure, darkens on exposure to oxygen
Odoracrid
Density1.70 g/mL,azeotrope
(57% HI by weight)
Boiling point127 °C (261 °F; 400 K) 1.03bar, azeotrope
Aqueous solution
Acidity (pKa)−9.3 (HI)[1]
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P260,P264,P280,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P321,P363,P405,P501
NFPA 704 (fire diamond)
Flash pointNon-flammable
Related compounds
Otheranions
Related compounds
Hydrogen iodide
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Hydroiodic acid (orhydriodic acid) is a colorless liquid. It is anaqueous solution ofhydrogen iodide with thechemical formulaHI(aq). It is astrong acid, in which hydrogen iodide isionized completely in an aqueous solution. Concentrated aqueous solutions of hydrogen iodide are usually 48% to 57% HI by mass.[2]

Preparation

[edit]
Main article:Hydrogen iodide § Synthesis

Reactions

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Hydroiodic acid reacts withoxygen in air to giveiodine:

4 HI(aq) + O2 → 2 H2O + 2 I2

Likehydrogen halides, hydroiodic acid adds toalkenes to givealkyl iodides. It can also be used as areducing agent, for example in thereduction of aromatic nitro compounds toanilines.[3]

Cativa process

[edit]

TheCativa process is a major end use of hydroiodic acid, which serves as aco-catalyst for the production ofacetic acid by thecarbonylation ofmethanol.[4][5]

The catalytic cycle of the Cativa process
The catalytic cycle of the Cativa process

Illicit uses

[edit]

Hydroiodic acid is listed as a U.S.Federal DEA List I Chemical, owing to its use as areducing agent related to the production ofmethamphetamine fromephedrine orpseudoephedrine (recovered from nasal decongestant pills).[6]

References

[edit]
  1. ^Perrin, D. D., ed. (1982) [1969].Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution.IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 32.ISBN 0-08-029214-3.LCCN 82-16524.
  2. ^Lyday, Phyllis A. (2005). "Iodine and Iodine Compounds".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 382–390.doi:10.1002/14356007.a14_381.ISBN 978-3-527-30673-2.
  3. ^Kumar, J. S. Dileep; Ho, ManKit M.; Toyokuni, Tatsushi (2001). "Simple and chemoselective reduction of aromatic nitro compounds to aromatic amines: reduction with hydriodic acid revisited".Tetrahedron Letters.42 (33):5601–5603.doi:10.1016/s0040-4039(01)01083-8.
  4. ^Jones, J. H. (2000)."The Cativa Process for the Manufacture of Acetic Acid"(PDF).Platinum Metals Rev.44 (3):94–105.
  5. ^Sunley, G. J.; Watson, D. J. (2000). "High productivity methanol carbonylation catalysis using iridium - The Cativa process for the manufacture of acetic acid".Catalysis Today.58 (4):293–307.doi:10.1016/S0920-5861(00)00263-7.
  6. ^Skinner, Harry F. (1990). "Methamphetamine synthesis via hydriodic acid/Red phosphorus reduction of ephedrine".Forensic Science International.48 (2):123–134.doi:10.1016/0379-0738(90)90104-7.

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