1,6-Hexanediol
Chemical compound
From Wikipedia, the free encyclopedia
1,6-Hexanediol is an organic compound with the formula (CH2CH2CH2OH)2. It is a colorless water-soluble solid.[3]
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| Names | |
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| Preferred IUPAC name
Hexane-1,6-diol | |
| Other names
Hexamethylene glycol; 1,6-Dihydroxyhexane; 1,6-Hexylene glycol; Hexamethylenediol; HDO | |
| Identifiers | |
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| DrugBank | |
| ECHA InfoCard | 100.010.068 |
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CompTox Dashboard (EPA) |
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| Properties | |
| C6H14O2 | |
| Molar mass | 118.176 g·molâ1 |
| Density | 0.967 |
| Melting point | 42 °C (108 °F; 315 K) |
| Boiling point | 250 °C (482 °F; 523 K) |
| 500g/L [1] | |
| Solubility | soluble in ethanol and acetone, slightly soluble in diethyl ether, insoluble in benzene.[2] |
| Hazards | |
| Flash point | 102 °C (216 °F; 375 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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History and synthesis
W. H. Perkin Jr. and his graduate student Edward Haworth first prepared the compound in 1894 during their research on cyclohexane. They heated a suspension of 1,6-dibromohexane, (which they were also the first to synthesize) in dilute aqueous potassium carbonate solution. They named resulting colorless syrup hexamethylene glycol.[4]
1,6-Hexanediol is industrially made by the hydrogenation of adipic acid or its esters.[3][5] Laboratory preparation could be achieved by reduction of adipates with lithium aluminium hydride, although this method is impractical on a commercial scale.
Properties
As 1,6-hexanediol contains hydroxyl groups, it undergoes the typical chemical reactions of alcohols such as dehydration, substitution, and esterification. Oxidation with pyridinium chlorochromate gives adipaldehyde.[6]
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 and ammonia respectively.[7]
Uses
1,6-Hexanediol is widely used for industrial polyester and polyurethane production.[3]
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.[3] Unsaturated polyester resins have also been made from 1,6-hexanediol, along with styrene, maleic anhydride and fumaric acid.[7]
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.[8] 2,5-Hexanediol and 1,4-butanediol have been observed to have minimal effect on behavior of disordered proteins as compared to 1,6-hexanediol.[9][10]