1-Propanol

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1-Propanol
Skeletal formula of 1-propanol
Ball and stick model of 1-propanol
Names
Preferred IUPAC name
Propan-1-ol[1]
Other names
  • n-Propyl alcohol
  • n-Propanol
  • n-PrOH
  • Ethylcarbinol
  • 1-Hydroxypropane
  • Propionic alcohol
  • Propionyl alcohol
  • Propionylol
  • Propyl alcohol
  • Propylic alcohol
  • Propylol
Identifiers
3D model (JSmol)
3DMetB00883
1098242
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.679
EC Number200-746-9
25616
KEGG
MeSH1-Propanol
RTECS numberUH8225000
UNII
UN number1274
Properties
Chemical formulaC3H8O
Molar mass60.10 g·mol−1
AppearanceColorless liquid
Odormild, alcohol-like[2]
Density0.803 g/mL
Melting point −126 °C; −195 °F; 147 K
Boiling point 97 to 98 °C; 206 to 208 °F; 370 to 371 K
Solubility in watermiscible
log P0.329
Vapor pressure1.99 kPa (at 20 °C)
Acidity (pKa)16
Basicity (pKb)−2
Magnetic susceptibility (χ)-45.176·10−6 cm3/mol
Refractive index (nD)1.387
Viscosity1.959 mPa·s (at 25 °C) [3]
Dipole moment1.68 D
Thermochemistry
Heat capacity (C)143.96 J K−1 mol−1
Std molar
entropy
(So298)
192.8 J K−1 mol−1
Std enthalpy of
formation
fHo298)
−302.79–−302.29 kJ mol−1
Std enthalpy of
combustion
cHo298)
−2.02156–−2.02106 MJ mol−1
Pharmacology
ATC codeD08AX03 (WHO)
Hazards
GHS pictogramsThe flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal wordDANGER
GHS hazard statementsH225, H318, H336
GHS precautionary statementsP210, P261, P280, P305+351+338
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
1
0
Flash point 22 °C (72 °F; 295 K)
Autoignition temperature 371 °C (700 °F; 644 K)
Explosive limits2.2% - 13.7%[2]
Lethal dose or concentration (LD, LC):
LD502800 mg/kg (rabbit, oral)
6800 mg/kg (mouse, oral)
1870 mg/kg (rat, oral)[4]
US health exposure limits (NIOSH):
PEL (Permissible)TWA 200 ppm (500 mg/m3)[2]
REL (Recommended)TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin][2]
IDLH (Immediate danger)800 ppm[2]
Related compounds
Related compounds
Supplementary data page
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH (sometimes represented as PrOH or n-PrOH). This colorless liquid is also known as propan-1-ol, 1-propyl alcohol, n-propyl alcohol, and n-propanol. It is an isomer of 2-propanol (propan-2-ol, isopropyl alcohol, isopropanol). 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.

Chemical properties[edit]

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.

Some example reactions of 1-propanol

Preparation[edit]

1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. The propionaldehyde is itself 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.

1-Propanol was discovered in 1853 by Gustave C. B. Chancel, who obtained it by fractional distillation of fusel oil. Indeed, 1-propanol is a major constituent of fusel oil, a by-product formed from certain amino acids when potatoes or grains are fermented to produce ethanol. This process is no longer a significant source of 1-propanol.

Safety[edit]

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]

Inhalation[edit]

Although this method is rare, it does exist. Propanol might be much more convenient than ethanol for inhalation because of its potency with nebulizers.

Propanol as fuel[edit]

1-propanol has high octane numbers and it is suitable for engine fuel usage. However, the production of propanol has been too expensive to make it a common fuel. The research octane number (RON) of propanol is 118 and anti-knock index (AKI) is 108.[7]

References[edit]

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 61. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b c d e "NIOSH Pocket Guide to Chemical Hazards #0533". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Pal, Amalendu; Gaba, Rekha (2008). "Volumetric, acoustic, and viscometric studies of molecular interactions in binary mixtures of dipropylene glycol dimethyl ether with 1-alkanols at 298.15 K". The Journal of Chemical Thermodynamics. 40 (5): 818–828. doi:10.1016/j.jct.2008.01.008.
  4. ^ "n-Propyl alcohol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Anthony J. Papa "Propanols" in Ullmann’s Encyclopedia of Industrial Chemistry 2011, Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_173.pub2
  6. ^ "N-PROPANOL Health-Base Assessment and Recommendation for HEAC" (PDF).
  7. ^ "Bioalcohols". Biofuel.org.uk. Retrieved 2014-04-16.

Further reading[edit]

  1. 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, ISBN 0-582-46236-3
  2. Lide, David R., ed. (2006-06-26). CRC Handbook of Chemistry and Physics, 87th Edition (87 ed.). TF-CRC. ISBN 0-8493-0487-3.
  3. Maryadele J. O'Neil, ed. (2006-11-03). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14 ed.). Merck. ISBN 0-911910-00-X.
  4. Perkin, W. H.; Kipping, F. S (1922). Organic Chemistry. London: W. & R. Chambers. ISBN 0-08-022354-0.

External links[edit]