Propan-1-ol (also propanol, n-propyl alcohol) is a
primary alcohol with the formula and sometimes
represented as PrOH or ''n''-PrOH. It is a colorless liquid and an
isomer of
2-propanol
Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group ( chemical formula ) it is the s ...
. It is formed naturally in small amounts during many fermentation processes and used as a
solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
in the pharmaceutical industry, mainly for
resin
In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on nat ...
s and
cellulose
Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wa ...
esters, and, sometimes, as a
disinfecting agent.
Chemical properties
Propan-1-ol shows the normal reactions of a
primary alcohol. Thus it can be converted to
alkyl halides; for example red
phosphorus
Phosphorus is a chemical element with the symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly reactive, phosphorus is never found as a free element on Ea ...
and
iodine produce
n-propyl iodide
''n''-Propyl iodide (also 1-propyl iodide or 1-iodopropane) is a colorless, flammable chemical compound. It has the chemical formula C3H7I and is prepared by heating ''n''-propyl alcohol with iodine and phosphorus
Phosphorus is a chemical ...
in 80% yield, while
with catalytic
gives
n-propyl chloride. Reaction with
acetic acid in the presence of an
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 propan-1-ol with
and 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.
Preparation
Propan-1-ol is manufactured by catalytic
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic ...
of
propionaldehyde. Propionaldehyde is produced via the
oxo process by
hydroformylation
Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon ...
of
ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds).
Ethylene ...
using
carbon monoxide
Carbon monoxide ( chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simpl ...
and
hydrogen
Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...
in the presence of a catalyst such as
cobalt octacarbonyl or a
rhodium
Rhodium is a chemical element with the symbol Rh and atomic number 45. It is a very rare, silvery-white, hard, corrosion-resistant transition metal. It is a noble metal and a member of the platinum group. It has only one naturally occurring i ...
complex.
:
:
A traditional laboratory preparation of propan-1-ol involves treating
''n''-propyl iodide with moist
.
Safety
Propan-1-ol is thought to be similar to
ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
in its effects on the human body, but 2–4 times more potent. Oral LD
50 in rats is 1870 mg/kg (compared to 7060 mg/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 propan-1-ol poisoning was reported.
Propan-1-ol as fuel
Propan-1-ol has high
octane number
An octane rating, or octane number, is a standard measure of a fuel's ability to withstand compression in an internal combustion engine without detonating. The higher the octane number, the more compression the fuel can withstand before detonating ...
and is suitable for
engine
An engine or motor is a machine designed to convert one or more forms of energy into mechanical energy.
Available energy sources include potential energy (e.g. energy of the Earth's gravitational field as exploited in hydroelectric power ...
fuel usage. However, propanol is too expensive to use as a motor fuel. The
research octane number (RON) of propanol is 118, and
anti-knock index
An octane rating, or octane number, is a standard measure of a fuel's ability to withstand compression in an internal combustion engine without detonating. The higher the octane number, the more compression the fuel can withstand before detonat ...
(AKI) is 108.
References
Further reading
#
#
#
#
External links
International Chemical Safety Card 0553
{{DEFAULTSORT:Propanol, 1-
Alkanols
Alcohol solvents
Primary alcohols
GABAA receptor positive allosteric modulators
Sedatives
Hypnotics