1-Propanol

1-Propanol
Skeletal formula of 1-propanol
Skeletal formula of 1-propanol
Ball and stick model 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
3D model (JSmol)
Beilstein Reference
 1098242
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.679
EC Number
  • 200-746-9
Gmelin Reference
 25616
KEGG
MeSH 1-Propanol
RTECS number
  • UH8225000
UNII
UN number 1274
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3 checkY
    Key: BDERNNFJNOPAEC-UHFFFAOYSA-N checkY
SMILES
  • CCCO
Properties
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
−45.176·10−6 cm3/mol
1.387
Viscosity 1.959 mPa·s (at 25 °C)[3]
1.68 D
Thermochemistry
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 diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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):
LD50 (median dose)
 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 liquid and an isomer of 2-propanol. 1-Propanol is used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

History

The compound was discovered by Gustave Chancel in 1853 by fractional distillation of fusel oil.[5] He measured its boiling point at 96°C, correctly identified its empirical formula, studied some of its chemical properties and gave it two names: propionic alcohol and hydrate of trityl.[6][7]

After several unsuccessful attempts, it was synthesized independently and by two different routes by Eduard Linnemann and Carl Schorlemmer in 1868.[8][9][10]

Occurrence

Fusel alcohols like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in many alcoholic beverages.

Chemical properties

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 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 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.[11]

H2C=CH2 + CO + H2 → CH3CH2CH=O
CH3CH2CH=O + H2 → CH3CH2CH2OH

Other proposed industrial processes include the two-step isomerization and hydrogenation of propylene oxide.[12]

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 to 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.[13] Due to a lack of long term data, the carcinogenicity of 1-propanol in humans is unknown.

1-Propanol as fuel

1-Propanol has a high octane number and is suitable for use as engine fuel. However, propanol is too expensive to use as a motor fuel. The research octane number (RON) of propanol is 118, and the anti-knock index (AKI) is 108.[14]

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. ^ a b c d e 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. Bibcode:2008JChTh..40..818P. doi:10.1016/j.jct.2008.01.008.
  4. ^ "n-Propyl alcohol". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
  5. ^ Chisholm, Hugh, ed. (1911). "Propyl Alcohols" . Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. p. 450.
  6. ^ Wisniak, Jaime (2013). "Gustav Charles Bonaventure Chancel". Educación Química. 24 (1): 23–30. doi:10.1016/S0187-893X(13)73191-4. ISSN 0187-893X.
  7. ^ s:fr:Page:Comptes rendus hebdomadaires des séances de l’Académie des sciences, tome 037, 1853.djvu/414
  8. ^ Linnemann, Eduard (1868). "Ueber die Darstellung der Fettalkohole aus ihren Anfangsgliedern. Reduction des Essigsäure-Anhydrids zu Aethylalkohol". Justus Liebigs Annalen der Chemie (in German). 148 (2): 249–251. doi:10.1002/jlac.18681480216. ISSN 1099-0690.
  9. ^ Zeitschrift für Chemie (in German). Quandt & Händel. 1868.
  10. ^ Schorlemmer, C. (1869). "On the Derivatives of Propane (Hydride of Propyl)". Proceedings of the Royal Society of London. 17: 372–376. doi:10.1098/rspl.1868.0072. ISSN 0370-1662.
  11. ^ Papa AJ (2011). "Propanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_173.pub2. ISBN 9783527303854.
  12. ^ Papa, Anthony J. (2000). Ullmann's Encyclopedia of Industrial Chemistry (1 ed.). Wiley. pp. 243–254. doi:10.1002/14356007. ISBN 978-3-527-30385-4.
  13. ^ Unmack JL (2011). "N-PROPANOL Health-Base Assessment and Recommendation for HEAC" (PDF).
  14. ^ "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. {{cite book}}: ISBN / Date incompatibility (help)
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