2-Octanol

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
CAS Number	123-96-6
ChemSpider	1892
EC Number	204-667-0
Jmol interactive 3D	Image
PubChem	1968
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 c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)N5C=CCC(=C5)N)O)O)O)OP(=O)(O)O)N
Properties
Chemical formula	C8H18O
Molar mass	130.23 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)
Solubility in water	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]
Henry's law constant (kH)	1.23E-04 atm-m3/mol)[4]
Refractive index (nD)	1.426 (20 °C)[5]
Viscosity	6.2 cP[6]
Thermochemistry
Specific heat capacity (C)	330.1 (J/mol*K) (298.5K)[1]
Hazards
GHS hazard statements	H315, H319, H412[4]
EU classification (DSD)	Directive 1999/45/EC
R-phrases	R36/38, R52/53[4]
Eye hazard	2[4]
Skin hazard	2[4]
Flash point	71[4] °C (160 °F; 344 K)
Autoignition temperature	265[4] °C (509 °F; 538 K)
Explosive limits	0.8 vol. % - 7,4 vol.%[4]
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	>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

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.

It is used such as or as a raw material in various applications: flavors and fragrances, paints and coatings, inks, adhesives, home care, lubricants and fuels. 2-Octanol can be a biobased alternative of 2-ethylhexanol and its derivates in numerous applications.

Manufacturing

2-Octanol is produced from castor oil through a cracking process. It is created as a by-product of sebacic acid manufacturing.^[8] Nowadays, India and China are the key producing countries of castor oil. Consequently, the majority of 2-Octanol production comes from these two countries: China & India.

Uses

2-Octanol is mainly used as:

• Flavor^{[7][9][10][11]}
• low-volatility solvent : Diverses Resins (Paints & Coatings, Adhesives, Inks, etc.), Agrochemicals, Mineral Extraction, etc.… ^{[12][13][14][15]}
• Defoaming agent : Pulp & Paper, Oil & Gas, Cement, Coatings, Coal, etc.
• a frother in mineral flotation^[16]
• 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.),^[17]
• Plasticizers (acrylates, maleates, etc.),
• Pesticides: Dinocap ^[18][19]
• Lubricants: Zinc dithiophosphate (ZDDP)
• Fragrances (salicylate)

See also

• 1-Octanol

Notes

1. 1 2 " 2-Octanol " on NIST/WebBook
2. ↑ Techniques de l’ingénieur : Solvants organiques
3. 1 2 " 2-Octanol " on ChemIDplus
4. 1 2 3 4 5 6 7 8 9 10 11 Record of 2-octanol in the GESTIS Substance Database of the IFA, accessed on 2 February 2010
5. ↑ http://www.chemicalbook.com/ChemicalProductProperty_EN_CB3272125.htm
6. ↑ Industrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7
7. 1 2 http://www.csst.qc.ca/prevention/reptox/pages/fiche-complete.aspx?no_produit=52472&nom=Octanol-2
8. ↑ http://www.ocl-journal.org/articles/ocl/abs/2009/04/ocl2009164p211/ocl2009164p211.html
9. ↑ http://www.thegoodscentscompany.com/data/rw1024631.html
10. ↑ Fenaroli's Handbook of Flavor Ingredients, Fifth Edition George A. Burdock ; CRC Press, 3 déc. 2004 - 1864 pages, Page 1420
11. ↑ Handbook of Flavor Ingredients, Volume 1 Giovanni Fenaroli (Prof. Dr.), Taylor & Francis, 1975 – page 443
12. ↑ Industrial Alcohol Technology Handbook ; NPCS Board of Consultants & Engineers ; ASIA PACIFIC BUSINESS PRESS Inc., 2 oct. 2010 - p. 206 – Utilisations principales
13. ↑ Industrial Solvents Handbook, Revised And Expanded Nicholas P. Cheremisinoff ; CRC Press, 15 avr. 2003 - 344 pages; pages 141
14. ↑ Paint and Coating Testing Manual, ASTM International, page 396
15. ↑ Chemistry of Tantalum and Niobium Fluoride Compounds; Anatoly Agulyansky ; Elsevier, 13 déc. 2004 - 408 pages; page 284
16. ↑ 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
17. ↑ 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
18. ↑ Pesticide Synthesis Handbook ; Thomas A. Unger ; William Andrew, 31 déc. 1996 - 1104 pages; page 1043
19. ↑ http://www.crops2industry.eu/images/pdf/bordeaux/10.%20ARKEMA_18-2-11.pdf

References

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