1,8-Octanediol

Chemical compound From Wikipedia, the free encyclopedia

1,8-Octanediol, also known as octamethylene glycol, is a diol with the molecular formula HO(CH2)8OH, a white solid. It can be produced with high purity by hydrogenation of esters of suberic acid.[2]: 133 

Quick facts Names, Identifiers ...
1,8-Octanediol
Names
Preferred IUPAC name
Octane-1,8-diol
Other names
1,8-Octanediol
Octamethylene glycol
1,8-Dihydroxyoctane
Identifiers
3D model (JSmol)
1633499
ChEBI
ChemSpider
ECHA InfoCard 100.010.083 Edit this at Wikidata
EC Number
  • 214-254-7
1524772
KEGG
UNII
  • InChI=1S/C8H18O2/c9-7-5-3-1-2-4-6-8-10/h9-10H,1-8H2 ☒N
    Key: OEIJHBUUFURJLI-UHFFFAOYSA-N ☒N
  • InChI=1/C8H18O2/c9-7-5-3-1-2-4-6-8-10/h9-10H,1-8H2
    Key: OEIJHBUUFURJLI-UHFFFAOYAW
  • OCCCCCCCCO
Properties
C8H18O2
Molar mass 146.227 g/mol
Appearance White solid[1]
Melting point 57 to 61 °C (135 to 142 °F; 330 to 334 K)
Boiling point 278.8 °C at 760 mmHg; 172 °C (342 °F; 445 K) at 20 mmHg
Slightly soluble[1]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Flash point 148 °C (298 °F; 421 K)
Safety data sheet (SDS) GFS Chemicals, Inc. MSDS
Related compounds
Related compounds
 1,9-Nonanediol
1,7-Heptanediol
1,2-Octanediol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,8-Octanediol, which has a low melting temperature, can be found at high purity for relatively low cost. These characteristics are ideal for a reference material at moderate temperature in the context of solid-liquid Phase-Changing Materials (PCMs).[3]

1,8-Octanediol dihexanoate strongly attracts adult male Parallelostethus attenuatus click beetles, and the pheromone of this species may consist entirely of this compound.[4]

Applications

Cosmetics

It is sometimes an ingredient of cosmetics as a plasticizer.[5]

As with other fatty alcohols, octane-1,8-diol is used in cosmetics as an emollient and humectant.[citation needed]

Polymers

1,8-Octanediol is used as a monomer in the synthesis of some polymers such as polyesters[6] and polyurethanes.[citation needed]

For example, poly(octanediol-co-citrate) is a biodegradable polymer that can be made antibacterial for biomedical applications.[7] This polymer, abbreviated POC[8][9] and also sometimes called poly(octamethylene-citrate),[9] is promising as a biocompatible and biodegradable polymer, and has been extensively investigated in relation to soft tissue engineering.[8]

A polymer created from 1,8-octanediol, citric acid, and sebacic acid, called polyoctanediol citrate/sebacate [p(OCS)], has also been synthesized.[10]

Synthesis

It can also be used in the synthesis of PCE.[11]

See also

References

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