2-Octanol

2-Octanol
Skeletal formula
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
3D model (JSmol)
1719322
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.244 Edit this at Wikidata
EC Number
  • 204-667-0
131016
RTECS number
  • RH0795000
UNII
  • 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
  • CC(O)CCCCCC
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 °C (−36 °F; 235 K)[6]
Boiling point 178.5 °C (353.3 °F; 451.6 K)[6]
1.120 g/L[3]
log P 2.9[3]
Vapor pressure 0.031 mbar (20 °C)
0.11 mbar (30 °C)
0.9 mbar (50 °C)[3]
1.23E-04 atm-m3/mol[3]
1.426 (20 °C)[4]
Viscosity 6.2 cP[5]
Thermochemistry
330.1 (J/mol*K) (298.5K)[1]
Hazards
Occupational safety and health (OHS/OSH):
Eye hazards
 2[3]
Skin hazards
 2[3]
GHS labelling:[3]
GHS02: Flammable GHS07: Exclamation mark GHS09: Environmental hazard
Warning
H226, H315, H319, H411, H412
P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P305+P351+P338, P370+P378, P391, P403+P235, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 71 °C (160 °F; 344 K)[3]
265 °C (509 °F; 538 K)[3]
Explosive limits 0.8 % v/v (lower)
7.4 % v/v (upper)[3]
Lethal dose or concentration (LD, LC):
>3.2 g/kg (rat, oral)
4 g/kg (mouse, oral)[7]
Safety data sheet (SDS) Flinn Scientific
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[8] The coproduct is a mixture of sebacic acid ((C8H16CO2H)2). Castor oil, which consists mainly of triglycerides of ricinoleic acid, is the main feedstock.[9][10]

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. ^ a b " 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. ^ a b c d e f g h i j 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. ^ a b " 2-Octanol " on ChemIDplus
  7. ^ a b "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. ^ a b c "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