Propan-1-ol
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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 number	UH8225000
SMILES	CCCO
Properties
Molecular formula	C3H8O
Molar mass	60.09 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
MSDS	External MSDS
EU classification	Flammable (F) Irritant (Xi)
NFPA 704	3 1 0
R-phrases	R11, R41, R67
S-phrases	(S2), S7, S16, S24, S26, S39
Flash point	15 °C
Related compounds
Related alcohols	Ethanol Propan-2-ol Butan-1-ol
Related compounds	Propionaldehyde Propionic acid 1-Chloropropane Propyl acetate
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Propan-1-ol is a primary alcohol with the formula CH₃CH₂CH₂OH. 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 1-iodopropane 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 1-iodopropane with moist Ag₂O.

History

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

References

The references used in this article may be clearer with a different or consistent style of citation, footnoting, or external linking. This article has been tagged since September 2007.

1. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. (1989). Vogel's Textbook of Practical Organic Chemistry (5th Edn.), Harlow:Longman. ISBN 0-582-46236-3
2. Handbook of Chemistry and Physics, 71st edition, CRC Press, Ann Arbor, Michigan, 1990.
3. The Merck Index, 7th edition, Merck & Co, Rahway, New Jersey, USA, 1960.
4. Perkin, W. H.; Kipping, F. S. (1922). Organic Chemistry, London: W. & R. Chambers.

External links

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