Hydrobromic acid
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| Names | ||
|---|---|---|
| IUPAC name
Bromane[1] | ||
| Other names
Hydronium bromide Bromhydric acid | ||
| Identifiers | ||
3D model (JSmol) |
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| ChEBI | ||
| ChEMBL | ||
| ChemSpider | ||
| ECHA InfoCard | 100.240.772 | |
| EC Number |
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| 620 | ||
| KEGG | ||
PubChem CID |
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| RTECS number |
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| UNII | ||
| UN number | 1048 1788 | |
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| Properties | ||
| HBr(aq) | ||
| Molar mass | 80.91 g·mol−1 | |
| Appearance | colorless liquid (impure samples can appear yellowish) | |
| Odor | acrid | |
| Density | 1.49 g/cm3 (48% w/w aq.) | |
| Melting point | −11 °C (12 °F; 262 K) (47–49% w/w aq.) | |
| Boiling point | 122 °C (252 °F; 395 K) at 700 mmHg (47–49% w/w aq.) | |
| 221 g/100 mL (0 °C) 204 g/100 mL (15 °C) 130 g/100 mL (100 °C) | ||
| Acidity (pKa) | −9[2] | |
| Viscosity | 0.84 cP (−75 °C) | |
| Thermochemistry | ||
Heat capacity (C) |
29.1 J/(K·mol) | |
Std molar entropy (S⦵298) |
198.7 J/(K·mol) | |
Std enthalpy of formation (ΔfH⦵298) |
−36.3 kJ/mol | |
| Hazards | ||
| GHS labelling: | ||
  | ||
| Danger | ||
| H314, H335 | ||
| P260, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P403+P233, P405, P501 | ||
| NFPA 704 (fire diamond) | ||
| Flash point | Nonflammable | |
| Safety data sheet (SDS) | ICSC 0282 | |
| Related compounds | ||
Other anions |
Hydrofluoric acid Hydrochloric acid Hydroiodic acid | |
Related compounds |
Hydrogen bromide | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hydrobromic acid is an aqueous solution of hydrogen bromide. It is a strong acid formed by dissolving the diatomic molecule hydrogen bromide (HBr) in water. "Constant boiling" hydrobromic acid is an aqueous solution that distills at 124.3 °C (255.7 °F) and contains 47.6% HBr by mass, which is 8.77 mol/L. Hydrobromic acid is one of the strongest mineral acids known.
Uses and reactions
[edit]Hydrobromic acid is mainly used for the production of inorganic bromides such as the hydrated bromides of iron, nickel, and zinc.[3]
Hydrobromic acid is a useful reagent for generating organobromine compounds. It converts primary alcohols to alkyl bromides.[4] Certain ethers are cleaved with HBr. HBr participates in anti-Markovnikov hydrohalogenation of alkenes in the presence of peroxides. The resulting 1-bromoalkanes are versatile alkylating agents, giving rise to fatty amines and quaternary ammonium salts.[5]
In the presence of hydrogen peroxide, it gives bromine. Since elemental bromine can be dangerous to handle, the H2O2/HBr mixture is used instead, e.g. for aromatic brominations:[6]
- 2 ArH + 2 HBr + H2O2 → 2 ArBr + 2 H2O (Ar = aryl)
Industrially significant organic compounds prepared from hydrobromic acid include allyl bromide, the fire-retardant tetrabromobisphenol A, and bromoacetic acid.
Synthesis
[edit]Hydrobromic acid can be prepared in the laboratory via the reaction of Br2, SO2, and water.[7]
- Br2 + SO2 + 2 H2O → H2SO4 + 2 HBr
More typically laboratory preparations involve the production of anhydrous HBr, which is then dissolved in water.
Hydrobromic acid has commonly been prepared industrially by reacting bromine with either sulfur or phosphorus and water. However, it can also be produced electrolytically.[7] It can also be prepared by treating bromides with non-oxidising acids like phosphoric or acetic acids.
Alternatively the acid can be prepared with dilute (5.8M) sulfuric acid and potassium bromide:[8]
- H2SO4 + KBr → KHSO4 + HBr
Using more concentrated sulfuric acid or allowing the reaction solution to exceed 75 °C further oxidizes HBr to elemental bromine. The acid is further purified by filtering out the KHSO4 and by distilling off the water until the solution reaches an azeotrope (124.3 °C). The yield is approximately 85%.[8]
Hydrobromic acid is available commercially in various concentrations and purities.
References
[edit]- ↑ Favre, Henri A.; Powell, Warren H., eds. (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. Cambridge: The Royal Society of Chemistry. p. 131. ISBN 9781849733069.
- ↑ Bell, R. P. The Proton in Chemistry, 2nd ed., Cornell University Press, Ithaca, NY, 1973.
- ↑ H. Lux (1963). "Iron". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 2. NY, NY: Academic Press. p. 1494.
- ↑ Martin K. Ellis and Bernard T. Golding (1985). "Optically Active Epoxides from Vicinal Diols via Vicinal Acetoxy Bromides: (S)-( − )- and (R)-( + )-Methyloxirane". Organic Syntheses. 63: 140. doi:10.15227/orgsyn.063.0140.
- ↑ Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. (2012). "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405. ISBN 978-3-527-30673-2.
- ↑ Schulze, Matthias (2016). "Synthesis of 1-Bromopyrene and 1-Pyrenecarbaldehyde". Organic Syntheses. 93: 100–114. doi:10.15227/orgsyn.093.0100.
- 1 2 Scott, A. (1900). "Preparation of Pure Hydrobromic Acid". Journal of the Chemical Society, Transactions. 77: 648–651. doi:10.1039/ct9007700648.
- 1 2 Brauer, Georg (1963). Handbook of Preparative Inorganic Chemistry. Vol. 1 (2nd ed.). New York: Academic Press. p. 285. ISBN 978-0121266011.
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External links
[edit]
Media related to Hydrogen bromide at Wikimedia Commons