2-Octanol

2-Octanol (octan-2-ol, 2-OH) is a fatty alcohol. It is a secondary eight-carbon chiral compound. 2-Octanol is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. 2-Octanol can be a biobased alternative of 2-ethylhexanol and its derivates in numerous applications.

2-Octanol
Names
IUPAC name
Octan-2-ol
Other names
2-Octanol
2-Octyl alcohol
1-Methyl-1-heptanol
Capryl alcohol
Methylhexylcarbinol
sec-Caprylic alcohol
Identifiers
3D model (JSmol)
1719322
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.244
EC Number
  • 204-667-0
131016
RTECS number
  • RH0795000
UNII
Properties
C8H18O
Molar mass 130.231 g·mol−1
Appearance Colourless liquid with characteristic odour[1]
Density 0.820 7 (g/cm3) (20°C)[2]
Melting point −38[3] °C (−36 °F; 235 K)
Boiling point 178.5[3] °C (353.3 °F; 451.6 K)
1.120 g/L[4]
log P 2.9[4]
Vapor pressure 0.031 mbar (20 °C)
0.11 mbar (30 °C)
0.9 mbar (50 °C)[4]
1.23E-04 atm-m3/mol[4]
1.426 (20 °C)[5]
Viscosity 6.2 cP[6]
Thermochemistry
330.1 (J/mol*K) (298.5K)[1]
Hazards
GHS pictograms
GHS Signal word Warning
H226, H315, H319, H411, H412[4]
P210, P233, P240, P241, P242, P243, P273, P280, P303+361+353, P370+378, P391, P403+235, P501
Eye hazard 2[4]
Skin hazard 2[4]
Flash point 71[4] °C (160 °F; 344 K)
265[4] °C (509 °F; 538 K)
Explosive limits 0.8 vol. % - 7,4 vol.%[4]
Lethal dose or concentration (LD, LC):
>3.2 g/kg (rat, oral)
4 g/kg (mouse, oral)[7]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Manufacturing

Cleavage of ricinoleic acid produces a mixture of 2-octanol and sebacic acid ((CH2)8(CO2H)2).[8][9]

Uses

2-Octanol is mainly used as:

It can also be used as a chemical intermediate for production of various other chemicals:

See also

Notes

  1. " 2-Octanol " on NIST/WebBook
  2. Techniques de l’ingénieur : Solvants organiques
  3. " 2-Octanol " on ChemIDplus
  4. Record of 2-octanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2 February 2010.
  5. "2-Octanol | 4128-31-8". chemicalbook.com. Retrieved 2019-10-05.
  6. Industrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7
  7. "Alcool caprylique secondaire". csst.qc.ca (in French). Retrieved 2019-10-05.
  8. Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.
  9. "Example of industrial valorisation of derivative products of Castor oil". OCL Journal. Retrieved 2019-10-05.
  10. "2-octanol, 123-96-6". thegoodscentscompany.com. Retrieved 2019-10-05.
  11. Fenaroli's Handbook of Flavor Ingredients, Fifth Edition George A. Burdock ; CRC Press, 3 déc. 2004 - 1864 pages, Page 1420
  12. Handbook of Flavor Ingredients, Volume 1 Giovanni Fenaroli (Prof. Dr.), Taylor & Francis, 1975 – page 443
  13. Industrial Alcohol Technology Handbook ; NPCS Board of Consultants & Engineers ; ASIA PACIFIC BUSINESS PRESS Inc., 2 oct. 2010 - p. 206 – Utilisations principales
  14. Industrial Solvents Handbook, Revised And Expanded Nicholas P. Cheremisinoff ; CRC Press, 15 avr. 2003 - 344 pages; pages 141
  15. Paint and Coating Testing Manual, ASTM International, page 396
  16. Chemistry of Tantalum and Niobium Fluoride Compounds; Anatoly Agulyansky ; Elsevier, 13 déc. 2004 - 408 pages; page 284
  17. Frothing in Flotation II: Recent Advances in Coal Processing, Volume 2; Janusz Laskowski, E T Woodburn; CRC Press, 21 oct. 1998 - 336 pages; page 19
  18. A Consumer's Dictionary of Cosmetic Ingredients: Complete Information About the Harmful and Desirable Ingredients in Cosmetics and Cosmeceuticals ; Ruth Winter - Crown Publishing Group, 10 févr. 2010 - 576 pages
  19. Pesticide Synthesis Handbook ; Thomas A. Unger ; William Andrew, 31 déc. 1996 - 1104 pages; page 1043
  20. "Valorization of Castor Oil for Polymer Applications" (PDF). Archived from the original (PDF) on 2015-04-02. Retrieved 2015-03-13.
  21. "2-Octanol | 123-96-6 | C8H18O | T&J Chemicals". Speciality Chemicals Supply | T&J Chemicals. Retrieved 2018-09-17.

References

  1. http://www.agrobiobase.com/fr/annuaire/bioproduits/chimie-formulation-synthese/2-octano
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