1-Propanol

1-Propanol
Skeletal formula of 1-propanol
Ball and stick model of 1-propanol
Names
Pronunciation ˈprəʊpən.wən.ɒl
Preferred IUPAC name
Propan-1-ol[1]
Other names
  • n-Propyl alcohol
  • n-Propanol
  • n-PrOH
  • Ethyl carbinol
  • 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
InChI
  • InChI=1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3 checkY
    Key: BDERNNFJNOPAEC-UHFFFAOYSA-N checkY
SMILES
  • CCCO
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 (S⦵298)
 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
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable liquid
GHS labelling:
Pictograms
 GHS02: Flammable GHS07: Exclamation mark
Signal word
 Danger
Hazard statements
 H225, H302, H318, H336
Precautionary statements
 P210, P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
3
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)
1699 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
1-Propanol (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

1-Propanol (also propan-1-ol, propanol, n-propyl alcohol) is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless, water-miscible liquid. It is an isomer of 2-propanol. 1-Propanol is used as a solvent.

Occurrence

Fusel alcohols like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in many alcoholic beverages. Propanol has been detected in the interstellar medium.[5]

Reactions

Some example reactions of 1-propanol

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, 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. When treated with formic acid it converts to propyl formate. Oxidation of 1-propanol with Na2Cr2O7 and H2SO4 gives propionaldehyde, as does PCC and the Swern oxidation. 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.[6]

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 according to a study conducted on rabbits. Many toxicology studies find oral acute LD50 ranging from 1.9 g/kg to 6.5 g/kg (compared to 7.06 g/kg for ethanol). It is metabolized into propionic acid. Effects include alcoholic intoxication and high anion gap metabolic acidosis. As of 2011, one case of lethal poisoning was reported following oral ingestion of 500mL of 1-propanol.[7] Due to lack of long term data, the carcinogenicity of 1-propanol in human beings is unknown.

Uses

1-Propanol is mainly used as a solvent, e.g., for inks, resins, and cellulose esters. It is a precursor to more specialized solvents such as glycol monopropyl ether and propyl propionate that are of commercial interest.[6] It is sometimes used as a disinfecting agent.

1-Propanol has high octane number and would be suitable as a motor fuel, but it is too expensive. The research octane number (RON) of propanol is 118, and anti-knock index (AKI) is 108.[8]

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. 1 2 3 4 5 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 or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ↑ Jiménez-Serra, Izaskun; Rodríguez-Almeida, Lucas F.; Martín-Pintado, Jesús; Rivilla, Víctor M.; Melosso, Mattia; Zeng, Shaoshan; Colzi, Laura; Kawashima, Yoshiyuki; Hirota, Eizi; Puzzarini, Cristina; Tercero, Belén; de Vicente, Pablo; Rico-Villas, Fernando; Requena-Torres, Miguel A.; Martín, Sergio (July 2022). "Precursors of fatty alcohols in the ISM: Discovery of n-propanol". Astronomy & Astrophysics. 663: A181. doi:10.1051/0004-6361/202142699. ISSN 0004-6361.
  6. 1 2 Papa AJ (2011). "Propanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_173.pub2. ISBN 9783527303854.
  7. ↑ Unmack JL (2011). "N-PROPANOL Health-Base Assessment and Recommendation for HEAC" (PDF).
  8. ↑ "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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