1,6-Hexanediol 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 (CH₂CH₂CH₂OH)₂. It is a colorless water-soluble solid.

History and synthesis

W. H. Perkin Jr. and his graduate student Edward Haworth first prepared the compound in 1894 during their research on

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...

. They boiled 1,6-dibromohexane (which they were also the first to synthesize) with dilute

potassium carbonate Potassium carbonate is the inorganic compound with the formula . It is a white salt, which is soluble in water and forms a strongly alkaline solution. It is deliquescent, often appearing as a damp or wet solid. Potassium carbonate is mainly used ...

solution and named the product hexamethylene glycol. 1,6-Hexanediol is industrially made by the

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 ...

adipic acid Adipic acid or hexanedioic acid is the organic compound with the formula C6H10O4. It a white crystalline powder at standard temperature and pressure. From an industrial perspective, it is the most important dicarboxylic acid at about 2.5 billion ...

or its esters. Laboratory preparation could be achieved by reduction of

adipates Adipic acid or hexanedioic acid is the organic compound with the chemical formula, formula C6H10O4. It a white crystalline powder at standard temperature and pressure. From an industrial perspective, it is the most important dicarboxylic acid at ...

with

lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthe ...

, although this method is impractical on a commercial scale.

Properties

As 1,6-hexanediol contains

hydroxyl 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 ...

groups, it undergoes the typical chemical reactions of

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

s such as

dehydration In physiology, dehydration is a lack of total body water that disrupts metabolic processes. It occurs when free water loss exceeds intake, often resulting from excessive sweating, health conditions, or inadequate consumption of water. Mild deh ...

, substitution, and

esterification 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 ...

. Oxidation with pyridinium chlorochromate gives adipaldehyde. Dehydration of 1,6-hexanediol gives oxepane, 2-methyltetrahydropyran and 2-ethyltetrahydrofuran. Corresponding thiophene and pyrrolidone can be made by reacting 1,6-hexanediol with

hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is toxic, corrosive, and flammable. Trace amounts in ambient atmosphere have a characteristic foul odor of rotten eggs. Swedish chemist ...

and

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

respectively.BASF intermediates, BASF

Uses

1,6-Hexanediol is widely used for industrial

polyester Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include some natura ...

and

polyurethane Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...

production. 1,6-Hexanediol can improve the hardness and flexibility of polyesters as it contains a fairly long hydrocarbon chain. In polyurethanes, it is used as a chain extender, and the resulting modified polyurethane has high resistance to hydrolysis as well as mechanical strength, but with a low glass transition temperature. It is also an intermediate to acrylics as a crosslinking agent, e.g. hexanediol diacrylate. Unsaturated polyester resins have also been made from 1,6-hexanediol, along with

styrene Styrene is an organic compound with the chemical formula C6H5CH=CH2. Its structure consists of a vinyl group as substituent on benzene. Styrene is a colorless, oily liquid, although aged samples can appear yellowish. The compound evaporates easi ...

maleic anhydride Maleic anhydride is an organic compound with the formula . It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers. Str ...

and

fumaric acid Fumaric acid or ''trans''-butenedioic acid is an organic compound with the formula HO2CCH=CHCO2H. A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297. The sa ...

Uses to study biomolecular condensates

1,6-Hexanediol has been used to characterize biomolecular condensates. The material properties of condensates can be examined to determine if they are solid or liquid condensates. 1,6-Hexanediol has been reported to interfere with weak hydrophobic protein-protein or protein-RNA interactions that comprise liquid condensates. 1,6-Hexanediol has been reported to dissolve liquid but not solid condensates. 2,5-Hexanediol and 1,4-butanediol have been observed to have minimal effect on behavior of disorderd proteins as compared to 1,6-hexanediol.

Safety

1,6-Hexanediol has low toxicity and low flammability, and is generally considered as safe. It is not irritating to skin, but may irritate the respiratory tract or mucous membranes. Dust or vapor of the compound can irritate or damage the eyes.

References

{{DEFAULTSORT:Hexanediol, 1, 6- Alkanediols