Hexamethylene glycol; 1,6-Dihydroxyhexane; 1,6-Hexylene glycol; Hexamethylenediol; HDO
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||118.176 g·mol−1|
|Melting point||42 °C (108 °F; 315 K)|
|Boiling point||250 °C (482 °F; 523 K)|
|Solubility||soluble in ethanol and acetone, slightly soluble in diethyl ether, insoluble in benzene.|
|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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1,6-Hexanediol is prepared industrially by the hydrogenation of adipic acid or its esters. Laboratory synthesis can be done by reduction of adipic acid with lithium aluminium hydride; however, since it is inexpensive and commercially available, it is usually not synthesized in the laboratory.
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.
Polycarbonates can be made from reaction with 1,6-hexanediol with phosgene.
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.
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.
- Chemicals and reagents 2008-2010, Merck
- CRC Handbook of Chemistry and Physics, 87th Edition
- Peter Werle; Marcus Morawietz; Stefan Lundmark; Kent Sörensen; Esko Karvinen; Juha Lehtonen (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2.
- BASF intermediates, BASF