1,8-Octanediol
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| Names | |
|---|---|
| Preferred IUPAC name
Octane-1,8-diol | |
| Other names
1,8-Octanediol
Octamethylene glycol 1,8-Dihydroxyoctane | |
| Identifiers | |
3D model (JSmol)
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| 1633499 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.010.083 |
| EC Number |
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| 1524772 | |
| KEGG | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| 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) | |
| 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, 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
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
[edit]Cosmetics
[edit]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
[edit]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
[edit]It can also be used in the synthesis of PCE.[11]
See also
[edit]References
[edit]- ^ a b "1,8-Octanediol, 98+%, Safety Data Sheet". Thermo Fisher Scientific. 10 February 2024. Archived from the original on 29 April 2025. Retrieved 29 April 2025.
- ^ Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2. ISBN 978-3-527-30673-2.
- ^ Velliadou, Danai; Antoniadis, Konstantinos D.; Assimopoulou, Andreana N.; Assael, Marc J.; Sequeira, Maria Carolina Margarido; Wakeham, William A. (2023-04-03). "Accurate Measurements of the Thermal Conductivity of n-Docosane, n-Tetracosane, 1,6-Hexanediol, and 1,8-Octanediol in the Solid and Liquid Phases". International Journal of Thermophysics. 44 (5): 78. doi:10.1007/s10765-023-03182-6. ISSN 1572-9567.
- ^ Millar, Jocelyn G.; Williams, Livy; Serrano, Jacqueline M.; Halloran, Sean; Grommes, Anna C.; Huseth, Anders S.; Kuhar, Thomas P.; Hanks, Lawrence M. (August 2022). "A Symmetrical Diester as the Sex Attractant Pheromone of the North American Click Beetle Parallelostethus attenuatus (Say) (Coleoptera: Elateridae)". Journal of Chemical Ecology. 48 (7–8): 598–608. doi:10.1007/s10886-022-01360-8. hdl:10919/109769. ISSN 1573-1561. PMID 35397045.
- ^ Scott, Laura N.; Fiume, Monice; Bergfeld, Wilma F.; Belsito, Donald V.; Hill, Ronald A.; Klaassen, Curtis D.; Liebler, Daniel C.; Marks, James G.; Shank, Ronald C.; Slaga, Thomas J.; Snyder, Paul W.; Heldreth, Bart (2024-04-01). "Safety Assessment of Alkane Diols as Used in Cosmetics". International Journal of Toxicology. 43 (2_suppl): 70S – 131S. doi:10.1177/10915818231224234. ISSN 1091-5818.
- ^ Qin, Jisong; Cheng, Zhengzai; Djouonkep, Lesly Dasilva Wandji; Gauthier, Mario (2024-10-08). "Polyesters derived from 4,4'-dixydroxybenzophenone: syntheses and properties". Iranian Polymer Journal. doi:10.1007/s13726-024-01392-9. ISSN 1026-1265.
- ^ García-Argüelles, Sara; Serrano, M. Concepción; Gutiérrez, María C.; Ferrer, M. Luisa; Yuste, Luis; Rojo, Fernando; del Monte, Francisco (2013-07-30). "Deep Eutectic Solvent-Assisted Synthesis of Biodegradable Polyesters with Antibacterial Properties". Langmuir. 29 (30): 9525–9534. doi:10.1021/la401353r. ISSN 0743-7463.
- ^ a b Ren, Hui-Hui; Zhao, Hui-Yu; Cui, Yang; Ao, Xiang; Li, Ai-Ling; Zhang, Zhong-Min; Qiu, Dong (2017-11-01). "Poly(1,8-octanediol citrate)/bioactive glass composite with improved mechanical performance and bioactivity for bone regeneration". Chinese Chemical Letters. SI: Young Scientists in Material Chemistry. 28 (11): 2116–2120. doi:10.1016/j.cclet.2017.07.014. ISSN 1001-8417.
- ^ a b Guo, Furong; Liang, Kai; Ji, Yali (2024-06-01). "Electrospun poly(octamethylene citrate) thermoset fibrous mat from chitin nanocrystal constructed Pickering emulsion". Colloid and Polymer Science. 302 (6): 891–900. doi:10.1007/s00396-024-05238-x. ISSN 1435-1536.
- ^ Djordjevic, Ivan; Choudhury, Namita Roy; Dutta, Naba K.; Kumar, Sunil (2009-03-20). "Synthesis and characterization of novel citric acid-based polyester elastomers". Polymer. 50 (7): 1682–1691. doi:10.1016/j.polymer.2009.01.045. ISSN 0032-3861.
- ^ Wang, Lin; Huang, Tengxiao; Xu, Xiaowei; Bu, Nitong; Wu, Zhenzhen; Zhao, Yunpeng; Zhou, Ya-Qin; Chen, Su; Chen, Yong; Pang, Jie (February 2025). "Robust Dual Equivariant Gradient Antibacterial Wound Dressing-Loaded Artificial Skin with Nano-chitin Particles Via an Electrospinning-Reactive Strategy". Advanced Fiber Materials. 7 (1): 204–218. doi:10.1007/s42765-024-00476-8. ISSN 2524-7921.