1-Propanol
Names Pronunciation /ˈprəʊpən.wən.ɒl/ Preferred IUPAC name Other names Identifiers 1098242 ChEBI ChEMBL ChemSpider DrugBank ECHA InfoCard 100.000.679 EC Number 25616 KEGG MeSH 1-Propanol RTECS number UNII UN number 1274 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 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) 192.8 J/(K·mol) −302.79…−302.29 kJ/mol −2.02156…−2.02106 MJ/mol Pharmacology D08AX03 (WHO) Hazards Occupational safety and health (OHS/OSH): Flammable liquid GHS labelling: Danger H225, H302, H318, H336 P210, P261, P280, P305+P351+P338 NFPA 704 (fire diamond) Flash point 22 °C (72 °F; 295 K) 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): TWA 200 ppm (500 mg/m3)[2] TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin][2] 800 ppm[2] Related compounds PropaneIsopropyl alcoholPropanamineEthanolButanol Supplementary data page 1-Propanol (data page)
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.
The compound was discovered by Gustave Chancel in 1853 by fractional distillation of fusel oil.[5][6] 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.[7][8]
After several unsuccessful attempts, it was synthesized independently and by two different routes by Eduard Linnemann and Carl Schorlemmer in 1868.[9][10][11]
Fusel alcohols like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in many alcoholic beverages.
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.
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.[12]
Other proposed industrial processes include the two-step isomerization and hydrogenation of propylene oxide.[13]
A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag2O.
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.[14] Due to a lack of long term data, the carcinogenicity of 1-propanol in humans is unknown.
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.[15]
- 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
- Lide DR, ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). TF-CRC. ISBN 0849304873.
- O’Neil MJ, ed. (2006). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th ed.). Merck. ISBN 091191000X.
- Perkin WH, Kipping FS (1922). Organic Chemistry. London: W. & R. Chambers. ISBN 0080223540. {{cite book}}: ISBN / Date incompatibility (help)
- International Chemical Safety Card 0553
- NIOSH Pocket Guide to Chemical Hazards
