1-Hexanol is an organic alcohol

Alcohol

In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

 with a six-carbon

Carbon

Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 chain and a condensed structural formula of CH₃(CH₂)₅OH. This colorless liquid is slightly soluble in water, but miscible with ether

Diethyl ether

Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

 and ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

. Two additional straight chain isomers of 1-hexanol, 2-hexanol

2-Hexanol

2-Hexanol is a six carbon alcohol in which the OH group is located on the second carbon atom. Its chemical formula is C6H14O or C6H13OH. It is an isomer of the other hexanols. 2-Hexanol has a chiral center and can be resolved into enantiomers....

 and 3-hexanol

3-Hexanol

3-Hexanol is an organic chemical compound. It occurs naturally in the flavor and aroma of plants such as pineapple and is used as a food additive to add flavor.- Reactions :...

, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C₆H₁₃OH. It is used in the perfume

Perfume

Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...

 industry.

Preparation

Hexanol is produced industrially by the oligomerization of ethylene

Ethylene

Ethylene is a gaseous organic compound with the formula . It is the simplest alkene . Because it contains a carbon-carbon double bond, ethylene is classified as an unsaturated hydrocarbon. Ethylene is widely used in industry and is also a plant hormone...

 using triethylaluminium

Triethylaluminium

Triethylaluminium is an organoaluminium compound. This volatile, colorless liquid is highly pyrophoric, igniting immediately upon exposure to air. It is normally stored in stainless steel containers either as a pure liquid or as a solution in hydrocarbon solvents such as hexane, heptane, or ...

 followed by oxidation of the alkylaluminium products

Organoaluminium

Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium bond. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer triisobutylaluminium, and the...

. An idealized synthesis is shown:

Al(C₂H₅)₃ + 6C₂H₄ → Al(C₆H₁₃)₃

Al(C₆H₁₃)₃ + 1½O₂ + 3H₂O → 3HOC₆H₁₃ + Al(OH)₃

The process generates a range of oligomers that are separated by distillation

Distillation

Distillation is a method of separating mixtures based on differences in volatilities of components in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....

.

Alternative methods

Another method of preparation entails hydroformylation

Hydroformylation

Hydroformylation, also known as oxo synthesis or oxo process, is an important industrial process for the production of aldehydes from alkenes. This chemical reaction entails the addition of a formyl group and a hydrogen atom to a carbon-carbon double bond...

 of 1-pentene followed by hydrogenation

Hydrogenation

Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...

 of the resulting aldehydes. This method is practiced in industry to produce mixtures of isomeric C₆-alcohols, which are precursors to plasticizer

Plasticizer

Plasticizers or dispersants are additives that increase the plasticity or fluidity of the material to which they are added; these include plastics, cement, concrete, wallboard, and clay. Although the same compounds are often used for both plastics and concretes the desired effects and results are...

s.

In principle, 1-hexene

1-Hexene

1-Hexene is an organic compound with the formula CH2CHC4H9. It is an alkene that is classified in industry as higher olefin and an alpha-olefin, the latter term meaning that the double bond is located at the alpha position, endowing the compound with higher reactivity and thus useful chemical...

 could be converted to 1-hexanol by hydroboration (diborane

Diborane

Diborane is the chemical compound consisting of boron and hydrogen with the formula B2H6. It is a colorless gas at room temperature with a repulsively sweet odor. Diborane mixes well with air, easily forming explosive mixtures. Diborane will ignite spontaneously in moist air at room temperature...

 in tetrahydrofuran

Tetrahydrofuran

Tetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. This heterocyclic compound has the chemical formula 4O. As one of the most polar ethers with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor...

 followed by treatment with hydrogen peroxide

Hydrogen peroxide

Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...

 and sodium hydroxide):



This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from ethylene.

Occurrence in Nature

1-Hexanol is believed to be a component of the odour of freshly mown grass. Alarm pheromones emitted by the Koschevnikov gland

Koschevnikov gland

The Koschevnikov gland is a gland of the honeybee. It is located near the sting shaft. The gland produces an alarm pheromone which is released when a bee stings. The pheromone contains more than 40 different compounds, including pentylacetate, butylacetate, 1-hexanol, n-butanol, octanol,...

 of honey bee

Honey bee

Honey bees are a subset of bees in the genus Apis, primarily distinguished by the production and storage of honey and the construction of perennial, colonial nests out of wax. Honey bees are the only extant members of the tribe Apini, all in the genus Apis...

s contain 1-hexanol.

See also

Cis-3-Hexenal

Cis-3-Hexenal

cis-3-Hexenal, also known as -3-hexenal and leaf aldehyde, is colorless liquid and an aroma compound with an intense grassy-green odor of freshly cut green grass and leaves. It is one of the major volatile compounds in ripe tomatoes. It is produced in small amounts by most plants and it acts as an...

, another volatile organic carbon biomolecule, is also considered responsible for the freshly mowed grass flavor.