Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data
Phase behaviour solid–liquid–gas
Spectral data
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what isYN ?)
Infobox references
Chemical compound
1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.
1-Propanol shows the normal reactions of a primary alcohol. Thus it can be converted to alkyl halides; for example red phosphorus and iodine produce n-propyl iodide in 80% yield, while PCl3 with catalytic ZnCl2 gives n-propyl chloride. Reaction with acetic acid in the presence of an H2SO4 catalyst under Fischer esterification conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7 and H2SO4 gives only a 36% yield of propionaldehyde, and therefore for this type of reaction higher yielding methods using PCC or the Swern oxidation are recommended. Oxidation with chromic acid yields propionic acid.
Preparation[]
1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. Propionaldehyde is produced via the oxo process by hydroformylation of ethylene using carbon monoxide and hydrogen in the presence of a catalyst such as cobalt octacarbonyl or a rhodium complex.[5]
H2C=CH2 + CO + H2 → CH3CH2CH=O
CH3CH2CH=O + H2 → CH3CH2CH2OH
A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag2O.
Safety[]
1-Propanol is thought to be similar to ethanol in its effects on the human body, but 2–4 times more potent. Oral LD50 in rats is 1870 mg/kg (compared to 7060 mg/kg for ethanol). It is metabolized into propionic acid. Effects include alcoholic intoxication and high anion gap metabolic acidosis. As of 2011, only one case of lethal 1-propanol poisoning was reported.[6]
Propanol as fuel[]
1-propanol has high octane number and is suitable for engine fuel usage. However, propanol is too expensive to use as a motor fuel. The research octane number (RON) of propanol is 118, and anti-knock index (AKI) is 108.[7]
References[]
^Favre HA, Powell WH (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. p. 61. doi:10.1039/9781849733069. ISBN9780854041824.
^ abcdeNIOSH Pocket Guide to Chemical Hazards. "#0533". National Institute for Occupational Safety and Health (NIOSH).
^Pal A, Gaba R (2008). "Volumetric, acoustic, and viscometric studies of molecular interactions in binary mixtures of dipropylene glycol dimethyl ether with 1-alkanols at 298.15 K". J. Chem. Thermodyn.40 (5): 818–828. doi:10.1016/j.jct.2008.01.008.
^"n-Propyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^
Papa AJ (2011). "Propanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_173.pub2. ISBN9783527303854.
Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. (1989), Vogel's Textbook of Practical Organic Chemistry (5th ed.), Harlow: Longman, ISBN0-582-46236-3
Lide DR, ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). TF-CRC. ISBN0849304873.
O'Neil MJ, ed. (2006). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th ed.). Merck. ISBN091191000X.
Perkin WH, Kipping FS (1922). Organic Chemistry. London: W. & R. Chambers. ISBN0080223540.
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