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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.
1-Propanol shows the normal reactions of a primary alcohol
. Thus it can be converted to alkyl halides
; for example red phosphorus
produce n-propyl iodide
in 90% yield, while PCl3
with catalytic ZnCl2
. 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
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
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.
1-Propanol was discovered in 1853
by Chancel, who obtained it by fractional distillation
of fusel oil
- Handbook of Chemistry and Physics, 71st edition, CRC Press, Ann Arbor, Michigan, 1990.
- The Merck Index, 7th edition, Merck & Co, Rahway, New Jersey, USA, 1960.
- Perkin, W. H.; Kipping, F. S. (1922). Organic Chemistry, London: W. & R. Chambers.