Hydroiodic acid

Hydroiodic acid
Space-filling model of hydrogen iodide	Space-filling model of water
The iodide anion	Space-filling model of the hydronium cation
Names
	IUPAC name Iodane[1]
	Other names Hydronium iodide
Identifiers
CAS Number	10034-85-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:43451 ;
ChemSpider	23224 ;
EC Number	233-109-9;
PubChem CID	24841;
RTECS number	MW3760000;
UNII	694C0EFT9Q ;
	InChI InChI=1S/BrH/h1H Key: CPELXLSAUQHCOX-UHFFFAOYSA-N ; InChI=1/BrH/h1H Key: CPELXLSAUQHCOX-UHFFFAOYAZ;
	SMILES I;
Properties
Chemical formula	HI(aq)
Molar mass	127.91 g/mol
Appearance	colorless liquid
Odor	acrid
Density	1.70 g/mL, azeotrope; (57% HI by weight)
Boiling point	127 °C (261 °F; 400 K) 1.03 bar, azeotrope
Solubility in water	Aqueous solution
Acidity (pKa)	-9.3
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
NFPA 704 (fire diamond)	3 0 0 ACID
Flash point	Non-flammable
Related compounds
Other anions	Hydrofluoric acid; Hydrochloric acid; Hydrobromic acid
Related compounds	Hydrogen iodide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hydroiodic acid (or hydriodic acid) is an aqueous solution of hydrogen iodide (HI). It is a strong acid, i.e. an acid that is ionized completely in an aqueous solution. It is colorless. Concentrated solutions are usually 48% to 57% HI.[2]

An oxidized solution of hydriodic acid.

Reactions

Hydroiodic acid reacts with oxygen in air to give iodine:

4 HI + O₂ → 2 H
₂O + 2 I₂

Like other hydrogen halides, hydroiodic acid adds to alkenes to give alkyl iodides. It can also be used as a reducing agent, for example in the reduction of aromatic nitro compounds to anilines.[3]

Cativa process

The Cativa process is a major end use of hydroiodic acid, which serves as a co-catalyst for the production of acetic acid by the carbonylation of methanol.[4][5]

The catalytic cycle of the Cativa process

Illicit uses

Hydroiodic acid is listed as a U.S. Federal DEA List I Chemical, owing to its use as a reducing agent related to the production of methamphetamine from ephedrine or pseudoephedrine (recovered from nasal decongestant pills).[6]

References

Henri A. Favre; Warren H. Powell, eds. (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. Cambridge: The Royal Society of Chemistry. p. 131.
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.
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.
Jones, J. H. (2000). "The Cativa Process for the Manufacture of Acetic Acid" (PDF). Platinum Metals Rev. 44 (3): 94–105.
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.
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.

External links

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[1] Henri A. Favre; Warren H. Powell, eds. (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. Cambridge: The Royal Society of Chemistry. p. 131.

[Ullmann-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.

[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.

[Cativa-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.