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2-Octanol

Names
Preferred IUPAC name Octan-2-ol
Other names 2-Octanol 2-Octyl alcohol 1-Methyl-1-heptanol sec-Capryl alcohol Methylhexylcarbinol sec-Caprylic alcohol
Identifiers
CAS Number	123-96-6
3D model (JSmol)	Interactive image
Beilstein Reference	1719322
ChEBI	CHEBI:37869
ChEMBL	ChEMBL510068
ChemSpider	18920
ECHA InfoCard	100.004.244
EC Number	204-667-0
Gmelin Reference	131016
PubChem CID	20083
RTECS number	RH0795000
UNII	66B0DD5E40
CompTox Dashboard (EPA)	DTXSID0027014
InChI InChI=1S/C20H30N7O16P3/c21-9-2-1-3-26(4-9)19-15(30)13(28)10(40-19)5-38-45(34,35)43-46(36,37)39-6-11-14(29)16(42-44(31,32)33)20(41-11)27-8-25-12-17(22)23-7-24-18(12)27/h1,3-4,7-8,10-11,13-16,19-20,28-30H,2,5-6,21H2,(H,34,35)(H,36,37)(H2,22,23,24)(H2,31,32,33)Key: IMPUPYZMUDSKSF-UHFFFAOYSA-N InChI=1/C20H30N7O16P3/c21-9-2-1-3-26(4-9)19-15(30)13(28)10(40-19)5-38-45(34,35)43-46(36,37)39-6-11-14(29)16(42-44(31,32)33)20(41-11)27-8-25-12-17(22)23-7-24-18(12)27/h1,3-4,7-8,10-11,13-16,19-20,28-30H,2,5-6,21H2,(H,34,35)(H,36,37)(H2,22,23,24)(H2,31,32,33)Key: IMPUPYZMUDSKSF-UHFFFAOYAA
SMILES CC(O)CCCCCC
Properties
Chemical formula	C8H18O
Molar mass	130.231 g·mol
Appearance	Colourless liquid with characteristic odour
Density	0.820 7 (g/cm) (20°C)
Melting point	−38 °C (−36 °F; 235 K)
Boiling point	178.5 °C (353.3 °F; 451.6 K)
Solubility in water	1.120 g/L
log P	2.9
Vapor pressure	0.031 mbar (20 °C) 0.11 mbar (30 °C) 0.9 mbar (50 °C)
Henry's law constant (kH)	1.23E-04 atm-m/mol
Refractive index (nD)	1.426 (20 °C)
Viscosity	6.2 cP
Thermochemistry
Heat capacity (C)	330.1 (J/mol*K) (298.5K)
Hazards
Occupational safety and health (OHS/OSH):
Eye hazards	2
Skin hazards	2
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H319, H411, H412
Precautionary statements	P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P305+P351+P338, P370+P378, P391, P403+P235, P501
NFPA 704 (fire diamond)	1 2 0
Flash point	71 °C (160 °F; 344 K)
Autoignition temperature	265 °C (509 °F; 538 K)
Explosive limits	0.8 % v/v (lower) 7.4 % v/v (upper)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	>3.2 g/kg (rat, oral) 4 g/kg (mouse, oral)
Safety data sheet (SDS)	Flinn Scientific
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

2-Octanol (octan-2-ol, 2-OH) is an organic compound with the chemical formula CH₃CH(OH)(CH₂)₅CH₃. It is a colorless oily liquid that is poorly soluble in water but soluble in most organic solvents. 2-Octanol is classified fatty alcohol. A secondary alcohol, it is chiral.

Production

2-Octanol is produced commercially by base-cleavage of ricinoleic acid. The coproduct is a mixture of sebacic acid ((C₈H₁₆CO₂H)₂). Castor oil, which consists mainly of triglycerides of ricinoleic acid, is the main feedstock.

Uses

2-Octanol is mainly used as:

• Flavor
• low-volatility solvent : Diverses Resins (Paints & Coatings, Adhesives, Inks, etc.), Agrochemicals, Mineral Extraction, etc....
• Defoaming agent : Pulp & Paper, Oil & Gas, Cement, Coatings, Coal, etc.
• a frother in mineral flotation
• wetting agent

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

• Surfactants (ethoxylates, sulfates, ether sulfates, etc.),
• Cosmetic emollients esters (palmitate, adipate, maleate, stearate, myristate, etc.),
• Plasticizers (acrylates, maleates, etc.),
• Pesticides: Dinocap
• Lubricants: Zinc dithiophosphate (ZDDP)
• Fragrances (salicylate)
• Used in the manufacturing of perfumes and disinfectant soaps
• Used to prevent foaming and as a solvent for fats and waxes
• Used to examine and control Essential Tremor and other types of involuntary neurological tremors

See also

• 1-Octanol

Notes

1. ^ " 2-Octanol " on NIST/WebBook
2. "Techniques de l'ingénieur : Solvants organiques". Archived from the original on 2015-04-02. Retrieved 2015-03-13.
3. ^ Record of 2-octanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2 February 2010.
4. "2-Octanol | 4128-31-8". chemicalbook.com. Archived from the original on 2015-04-02. Retrieved 2019-10-05.
5. Industrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7
6. ^ " 2-Octanol " on ChemIDplus
7. ^ "Alcool caprylique secondaire". csst.qc.ca (in French). Archived from the original on 2015-04-02. Retrieved 2019-10-05.
8. Roger Adams, C. S. Marvel (1921). "Methyl-n-hexylcarbinol". Organic Syntheses. 1: 61. doi:10.15227/orgsyn.001.0061.
9. Cornils, Boy; Lappe, Peter (2014). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.pub3. ISBN 3527306730.
10. Borg, Patrick; Lê, Guillaume; Lebrun, Stéphanie; Pées, Bernard (2009). "Example of Industrial Valorisation of Derivative Products of Castor Oil". Oléagineux, Corps Gras, Lipides. 16 (4–5–6). OCL Journal: 211–214. doi:10.1051/ocl.2009.0276. Archived from the original on 2015-09-24. Retrieved 2019-10-05.
11. "2-octanol, 123-96-6". thegoodscentscompany.com. Archived from the original on 2006-06-05. Retrieved 2019-10-05.
12. Fenaroli's Handbook of Flavor Ingredients, Fifth Edition George A. Burdock; CRC Press, 3 déc. 2004 - 1864 pages, Page 1420
13. Handbook of Flavor Ingredients, Volume 1 Giovanni Fenaroli (Prof. Dr.), Taylor & Francis, 1975 – page 443
14. Industrial Alcohol Technology Handbook; NPCS Board of Consultants & Engineers; ASIA PACIFIC BUSINESS PRESS Inc., 2 oct. 2010 - p. 206 – Utilisations principales
15. Industrial Solvents Handbook, Revised And Expanded Nicholas P. Cheremisinoff; CRC Press, 15 avr. 2003 - 344 pages; pages 141
16. Paint and Coating Testing Manual, ASTM International, page 396
17. Chemistry of Tantalum and Niobium Fluoride Compounds; Anatoly Agulyansky; Elsevier, 13 déc. 2004 - 408 pages; page 284
18. 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
19. 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
20. Pesticide Synthesis Handbook; Thomas A. Unger; William Andrew, 31 déc. 1996 - 1104 pages; page 1043
21. "Valorization of Castor Oil for Polymer Applications" (PDF). Archived from the original (PDF) on 2015-04-02. Retrieved 2015-03-13.
22. ^ "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

• Fatty alcohols
• Alkanols