Propan-1-ol (also propanol, n-propyl alcohol) is a

primary alcohol A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group. In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary a ...

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 sim ...

. 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 n ...

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 w ...

esters, and, sometimes, as a disinfecting agent.

Chemical properties

Propan-1-ol shows the normal reactions of a

. Thus it can be converted to

alkyl halides The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely us ...

; 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 Ear ...

and iodine produce n-propyl iodide in 80% yield, while with catalytic gives

n-propyl chloride ''n''-Propyl chloride (also 1-propyl chloride or 1-chloropropane) is a colorless, flammable chemical compound. It has the chemical formula C3H7Cl and is prepared by reacting ''n''-propyl alcohol with phosphorus trichloride in the presence of ...

. Reaction with acetic acid in the presence of an catalyst under Fischer esterification conditions gives

propyl acetate Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used i ...

, 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 Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a slightly fruity odour. It is produced on a large scale industrially. Production Propionalde ...

, and therefore for this type of reaction higher yielding methods using PCC or the

Swern oxidation The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine. It is one ...

are recommended. Oxidation with

chromic acid The term chromic acid is usually used for a mixture made by adding concentrated sulfuric acid to a dichromate, which may contain a variety of compounds, including solid chromium trioxide. This kind of chromic acid may be used as a cleaning mixtu ...

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 organ ...

. Propionaldehyde is produced via the

oxo process 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 d ...

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 d ...

of 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 simple ...

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-toxic ...

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 LD₅₀ 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 High anion gap metabolic acidosis is a form of metabolic acidosis characterized by a high anion gap (a medical value based on the concentrations of ions in a patient's serum). Metabolic acidosis occurs when the body produces too much acid, or when ...

. 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 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 detonating ...

(AKI) is 108.

References

External links