1-Pentanol, (or ''n''-pentanol, pentan-1-ol), is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula and is classified as 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 ...

CRC Handbook of Chemistry and Physics The ''CRC Handbook of Chemistry and Physics'' is a comprehensive one-volume reference resource for science research. First published in 1914, it is currently () in its 105th edition, published in 2024. It is known colloquially among chemists as ...

65th ed. It is a colourless

liquid Liquid is a state of matter with a definite volume but no fixed shape. Liquids adapt to the shape of their container and are nearly incompressible, maintaining their volume even under pressure. The density of a liquid is usually close to th ...

with a distinctive

aroma An odor (American English) or odour (Commonwealth English; see spelling differences) is a smell or a scent caused by one or more volatilized chemical compounds generally found in low concentrations that humans and many animals can perceive v ...

. It is one of 8 isomeric alcohols with the formula . It is used as a solvent, a biological drying agent and in the synthesis of some fragrance compounds. It is also a common component of fusel alcohols (fusel oils), the undesirable byproducts of alcoholic fermentation.

Preparation

1-Pentanol is prepared from

1-butene 1-Butene (IUPAC name: But-1-ene, also known as 1-butylene) is the organic compound with the formula CH3CH2CH=CH2. It is a colorless gas, but easily condensed to give a colorless liquid. It is classified as a linear alpha-olefin (terminal alkene). ...

hydroformylation In organic chemistry, 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 () and a hydrogen ...

followed by

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 redox, reduce or Saturated ...

of the resulting pentanal. : : Pentanol can be prepared by

fractional distillation Fractional distillation is the separation of a mixture into its component parts, or fractions. Chemical compounds are separated by heating them to a temperature at which one or more fractions of the mixture will vaporize. It uses distillation ...

of fusel oil. To reduce the use of

fossil fuel A fossil fuel is a flammable carbon compound- or hydrocarbon-containing material formed naturally in the Earth's crust from the buried remains of prehistoric organisms (animals, plants or microplanktons), a process that occurs within geolog ...

s, research is underway to develop cost-effective methods of producing (chemically identical) bio-pentanol with

fermentation Fermentation is a type of anaerobic metabolism which harnesses the redox potential of the reactants to make adenosine triphosphate (ATP) and organic end products. Organic molecules, such as glucose or other sugars, are catabolized and reduce ...

Uses and occurrence

The

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

(OH) is the active site of many reactions. The

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

formed from 1-pentanol and

butyric acid Butyric acid (; from , meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula . It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid (2-met ...

is pentyl butyrate, which has an

apricot An apricot (, ) is a fruit, or the tree that bears the fruit, of several species in the genus ''Prunus''. Usually an apricot is from the species '' P. armeniaca'', but the fruits of the other species in ''Prunus'' sect. ''Armeniaca'' are also ...

-like odor. The ester formed from 1-pentanol and

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

is amyl acetate (also called pentyl acetate), which has a

banana A banana is an elongated, edible fruit – botanically a berry – produced by several kinds of large treelike herbaceous flowering plants in the genus '' Musa''. In some countries, cooking bananas are called plantains, distinguishing the ...

-like odor. It is a precursor to dipentyl

zinc dithiophosphate Zinc dialkyldithiophosphates (often referred to as ZDDP) are a family of coordination compounds developed in the 1940s that feature zinc bound to the anion of a dialkyldithiophosphoric salt (e.g., ammonium diethyl dithiophosphate). These uncharge ...

s, which are used in froth flotation. In 2014, a study was conducted comparing the performance of

diesel fuel Diesel fuel, also called diesel oil, heavy oil (historically) or simply diesel, is any liquid fuel specifically designed for use in a diesel engine, a type of internal combustion engine in which fuel ignition takes place without a spark as a re ...

blends with various proportions of pentanol as an

additive Additive may refer to: Mathematics * Additive function, a function in number theory * Additive map, a function that preserves the addition operation * Additive set-function see Sigma additivity * Additive category, a preadditive category with fin ...

. While gaseous emissions increased with higher concentrations of pentanol, particulate emissions decreased.Wei, Liangjie & Cheung, C.s & Huang, Zuohua. (2014). Effect of n-pentanol addition on the combustion, performance and emission characteristics of a direct-injection diesel engine. Energy. 70. 10.1016/j.energy.2014.03.106. Pentanol is often used as a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

References

{{DEFAULTSORT:Pentanol, 1- Alkanols Primary alcohols GABAA receptor positive allosteric modulators Sedatives Hypnotics Pentyl compounds