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Hydroiodic acid

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

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
  • 10034-85-2 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:43451 Y
ChemSpider
  • 23224 Y
EC Number
  • 233-109-9
  • 24841
RTECS number
  • MW3760000
UNII
  • 694C0EFT9Q N
  • InChI=1S/BrH/h1H Y
    Key: CPELXLSAUQHCOX-UHFFFAOYSA-N Y
  • InChI=1/BrH/h1H
    Key: CPELXLSAUQHCOX-UHFFFAOYAZ
Properties
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
Aqueous solution
Acidity (pKa) -9.3
Hazards
GHS labelling:
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 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).
An oxidized solution of hydriodic acid.

Reactions edit

Hydroiodic acid reacts with oxygen in air to give iodine:

4 HI + O2 → 2 H
2
O
+ 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 edit

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 edit

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 edit

  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.
  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 978-3527306732.
  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.

External links edit

hydroiodic, acid, hydriodic, acid, colorless, aqueous, solution, hydrogen, iodide, strong, acid, which, ionized, completely, aqueous, solution, concentrated, solutions, hydroiodic, acid, usually, space, filling, model, hydrogen, iodide, space, filling, model, . Hydroiodic acid or hydriodic acid is a colorless and aqueous solution of hydrogen iodide HI It is a strong acid which is ionized completely in an aqueous solution Concentrated solutions of hydroiodic acid are usually 48 to 57 HI 2 Hydroiodic acid Space filling model of hydrogen iodide Space filling model of waterThe iodide anion Space filling model of the hydronium cationNamesIUPAC name Iodane 1 Other names Hydronium iodideIdentifiersCAS Number 10034 85 2 Y3D model JSmol Interactive imageChEBI CHEBI 43451 YChemSpider 23224 YEC Number 233 109 9PubChem CID 24841RTECS number MW3760000UNII 694C0EFT9Q NInChI InChI 1S BrH h1H YKey CPELXLSAUQHCOX UHFFFAOYSA N YInChI 1 BrH h1HKey CPELXLSAUQHCOX UHFFFAOYAZSMILES IPropertiesChemical formula HI aq Molar mass 127 91 g molAppearance colorless liquidOdor acridDensity 1 70 g mL azeotrope 57 HI by weight Boiling point 127 C 261 F 400 K 1 03 bar azeotropeSolubility in water Aqueous solutionAcidity pKa 9 3HazardsGHS labelling PictogramsSignal word DangerHazard statements H314Precautionary statements P260 P264 P280 P301 P330 P331 P303 P361 P353 P304 P340 P305 P351 P338 P310 P321 P363 P405 P501NFPA 704 fire diamond 300ACIDFlash point Non flammableRelated compoundsOther anions Hydrofluoric acidHydrochloric acidHydrobromic acidRelated compounds Hydrogen iodideExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references An oxidized solution of hydriodic acid Contents 1 Reactions 1 1 Cativa process 1 2 Illicit uses 2 References 3 External linksReactions editHydroiodic acid reacts with oxygen in air to give iodine 4 HI O2 2 H2 O 2 I2Like 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 edit 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 nbsp The catalytic cycle of the Cativa processIllicit uses edit 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 edit 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 ISBN 978 3527306732 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 editInternational Chemical Safety Card 1326 European Chemicals Bureau Viscosities of Aqueous Hydrochloric Acid Solutions and Densities and Viscosities of Aqueous Hydroiodic Acid Solutions Retrieved from https en wikipedia org w index php title Hydroiodic acid amp oldid 1194994569, wikipedia, wiki, book, books, library,

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