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 number	UH8225000
SMILES	CCCO
ChemSpider ID	1004
Properties
Molecular formula	C3H8O
Molar mass	60.0952 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)
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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox 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 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. (1989), Vogel's Textbook of Practical Organic Chemistry (5th ed.), 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