1-Propanol

1-Propanol is a primary alcohol with the formula CH
3CH
2CH
2OH (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.

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
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference
 1098242
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.679
EC Number
  • 200-746-9
Gmelin Reference
 25616
KEGG
MeSH 1-Propanol
PubChem CID
RTECS number
  • UH8225000
UNII
UN number 1274
Properties
Chemical formula
 C3H8O
Molar mass 60.096 g·mol−1
Appearance Colorless liquid
Odor mild, alcohol-like[2]
Density 0.803 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 water
 miscible
log P 0.329
Vapor pressure 1.99 kPa (at 20 °C)
Acidity (pKa) 16
Basicity (pKb) −2
Magnetic susceptibility (χ)
 −45.176·10−6 cm3/mol
Refractive index (nD)
 1.387
Viscosity 1.959 mPa·s (at 25 °C) [3]
Dipole moment
 1.68 D
Thermochemistry
Heat capacity (C)
 143.96 J/(K·mol)
Std molar
entropy (So298)
 192.8 J/(K·mol)
Std enthalpy of
formation (ΔfH⦵298)
 −302.79…−302.29 kJ/mol
Std enthalpy of
combustion (ΔcH⦵298)
 −2.02156…−2.02106 MJ/mol
Pharmacology
D08AX03 (WHO)
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H318, H336
GHS precautionary statements
 P210, P261, P280, P305+351+338
NFPA 704 (fire diamond)
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 code
3
1
0
Flash point 22 °C (72 °F; 295 K)
Autoignition
temperature
 371 °C (700 °F; 644 K)
Explosive limits 2.2–13.7%[2]
Lethal dose or concentration (LD, LC):
2800 mg/kg (rabbit, oral)
6800 mg/kg (mouse, oral)
1870 mg/kg (rat, oral)[4]
NIOSH (US health exposure limits):
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
 Propane
Isopropyl alcohol
Propanamine
Ethanol
Butanol
Supplementary data page
Structure and
properties
 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 verify (what is YN ?)
Infobox references

Chemical properties

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 PCl
3 with catalytic ZnCl
2 gives n-propyl chloride. Reaction with acetic acid in the presence of an H
2SO
4 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 Na
2Cr
2O
7 and H
2SO
4 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

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]

H
2C=CH
2 + CO + H
2 → CH
3CH
2CH=O
CH
3CH
2CH=O + H
2 → CH
3CH
2CH
2OH

A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag
2O.

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

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

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

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
  1. 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. ISBN 9780854041824.
  2. NIOSH Pocket Guide to Chemical Hazards. "#0533". National Institute for Occupational Safety and Health (NIOSH).
  3. 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.
  4. "n-Propyl alcohol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. Papa AJ (2011). "Propanols". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_173.pub2. ISBN 9783527303854.
  6. Unmack JL (2011). "N-PROPANOL Health-Base Assessment and Recommendation for HEAC" (PDF).
  7. "Bioalcohols". Biofuel.org.uk. 2010. Retrieved 16 Apr 2014.

Further reading
  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 DR, ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). TF-CRC. ISBN 0849304873.
  3. O'Neil MJ, ed. (2006). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th ed.). Merck. ISBN 091191000X.
  4. Perkin WH, Kipping FS (1922). Organic Chemistry. London: W. & R. Chambers. ISBN 0080223540.
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