Chemistry:1,8-Octanediol

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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.[1]: 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).[2]

1,8-Octanediol dihexanoate strongly attracts adult male Parallelostethus attenuatus click beetles, and the pheromone of this species may consist entirely of this compound.[3]

Applications

Cosmetics

It is sometimes an ingredient of cosmetics as a plasticizer.[4]


Polymers

1,8-Octanediol is used as a monomer in the synthesis of some polymers such as polyesters[5] and polyurethanes. For example, poly(octanediol-co-citrate) is a biodegradable polymer that can be made antibacterial for biomedical applications.[6] This polymer, abbreviated POC[7][8] and also sometimes called poly(octamethylene-citrate),[8] is promising as a biocompatible and biodegradable polymer, and has been extensively investigated in relation to soft tissue engineering.[7]

A polymer created from 1,8-octanediol, citric acid, and sebacic acid, called polyoctanediol citrate/sebacate [p(OCS)], has also been synthesized.[9]

Synthesis

It can also be used in the synthesis of PCE.[10]

See also

References

  1. ↑ Noweck, Klaus; Grafahrend, Wolfgang (2006). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2. 
  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" (in en). International Journal of Thermophysics 44 (5): 78. doi:10.1007/s10765-023-03182-6. ISSN 1572-9567. 
  3. ↑ 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. ISSN 1573-1561. PMID 35397045. 
  4. ↑ Scott, Laura N.; Fiume, Monice; Bergfeld, Wilma F.; Belsito, Donald V.; Hill, Ronald A.; Klaassen, Curtis D.; Liebler, Daniel C.; Marks, James G. et al. (2024-04-01). "Safety Assessment of Alkane Diols as Used in Cosmetics" (in en). International Journal of Toxicology 43 (2_suppl): 70S–131S. doi:10.1177/10915818231224234. ISSN 1091-5818. https://journals.sagepub.com/doi/10.1177/10915818231224234. 
  5. ↑ Qin, Jisong; Cheng, Zhengzai; Djouonkep, Lesly Dasilva Wandji; Gauthier, Mario (2024-10-08). "Polyesters derived from 4,4'-dixydroxybenzophenone: syntheses and properties" (in en). Iranian Polymer Journal 34 (4): 485–497. doi:10.1007/s13726-024-01392-9. ISSN 1026-1265. https://link.springer.com/10.1007/s13726-024-01392-9. 
  6. ↑ 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. https://pubs.acs.org/doi/10.1021/la401353r. 
  7. ↑ 7.0 7.1 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. https://www.sciencedirect.com/science/article/abs/pii/S1001841717302590. 
  8. ↑ 8.0 8.1 Guo, Furong; Liang, Kai; Ji, Yali (2024-06-01). "Electrospun poly(octamethylene citrate) thermoset fibrous mat from chitin nanocrystal constructed Pickering emulsion" (in en). Colloid and Polymer Science 302 (6): 891–900. doi:10.1007/s00396-024-05238-x. ISSN 1435-1536. https://link.springer.com/article/10.1007/s00396-024-05238-x. 
  9. ↑ 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. https://www.sciencedirect.com/science/article/abs/pii/S0032386109000834. 
  10. ↑ Wang, Lin; Huang, Tengxiao; Xu, Xiaowei; Bu, Nitong; Wu, Zhenzhen; Zhao, Yunpeng; Zhou, Ya-Qin; Chen, Su et al. (February 2025). "Robust Dual Equivariant Gradient Antibacterial Wound Dressing-Loaded Artificial Skin with Nano-chitin Particles Via an Electrospinning-Reactive Strategy" (in en). Advanced Fiber Materials 7 (1): 204–218. doi:10.1007/s42765-024-00476-8. ISSN 2524-7921. https://link.springer.com/10.1007/s42765-024-00476-8. 



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