Propan-1-ol

Propanol
IUPAC name	propan-1-ol
Other names	1-propanol propyl alcohol n-propanol n-propyl alcohol propanol
Identifiers
CAS number	[71-23-8]
RTECS	UH8225000
ChemSpider	1004
SMILES	CCCO
Properties
Chemical formula	C3H8O
Molar mass	60.10 g/mol
Appearance	Clear, colourless liquid
Density	0.8034 g/cm3, liquid
Melting point	−126.5 °C (146.7 K)
Boiling point	97.1 °C (370.3 K)
Solubility in water	Fully miscible
Acidity (pKa)	(~16)
Viscosity	1.938 cP at 25°C
Structure
Dipole moment	1.68 D
Hazards
EU classification	Flammable (F) Irritant (Xi)
R-phrases	Template:R11, Template:R41, Template:R67
S-phrases	Template:S2, Template:S7, Template:S16, Template:S24, Template:S26, Template:S39
NFPA 704
Flash point	15 °C
Related compounds
Other alcohols	Ethanol Propan-2-ol Butan-1-ol
Other compounds	Propionaldehyde Propionic acid 1-Chloropropane Propyl acetate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Propan-1-ol is a primary alcohol with the Molecular formula of C₃H₈O. It is also known as 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol. It is an isomer of propan-2-ol. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes.

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 90% yield, while PCl₃ with catalytic ZnCl₂ gives 1-chloropropane. 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

Preparation

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 is no longer a significant source of propanol.

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.

(1) H₂C=CH₂ + CO + H₂ → CH₃CH₂CH=O

(2) CH₃CH₂CH=O + H₂ → CH₃CH₂CH₂OH

A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag₂O.

History

1-Propanol was discovered in 1853 by Chancel, who obtained it by fractional distillation of fusel oil.

References

1. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: Harlow, 1989. ISBN 0-582-46236-3
2. (2006-06-26) CRC Handbook of Chemistry and Physics, 87th Edition, 87, TF-CRC. ISBN 0849304873. 
3. (2006-11-03) in Maryadele J. O'Neil: The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 14, Merck. ISBN 091191000X. 
4. (1922) Organic Chemistry. London: W. & R. Chambers. 

External links

• International Chemical Safety Card 0553
• NIOSH Pocket Guide to Chemical Hazards