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.
 | |
| 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) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.004.244 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
|
| |
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| 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] |
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 | |
Heat capacity (C) |
330.1 (J/mol*K) (298.5K)[1] |
| Hazards | |
GHS hazard statements |
H315, H319, H412[4] |
| 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): | |
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 | |
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:
- Flavor[7][10][11][12]
- low-volatility solvent : Diverses Resins (Paints & Coatings, Adhesives, Inks, etc.), Agrochemicals, Mineral Extraction, etc....[13][14][15][16]
- Defoaming agent : Pulp & Paper, Oil & Gas, Cement, Coatings, Coal, etc.
- a frother in mineral flotation[17]
- 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.),[18]
- Plasticizers (acrylates, maleates, etc.),
- Pesticides: Dinocap [19][20]
- Lubricants: Zinc dithiophosphate (ZDDP)
- Fragrances (salicylate)
- Used in the manufacturing of perfumes and disinfectant soaps[21]
- Used to prevent foaming and as a solvent for fats and waxes[21]
- Used to examine and control Essential Tremor and other types of involuntary neurological tremors[21]
See also
Notes
- " 2-Octanol " on NIST/WebBook
- Techniques de l’ingénieur : Solvants organiques
- " 2-Octanol " on ChemIDplus
- Record of 2-octanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2 February 2010.
- "2-Octanol | 4128-31-8". chemicalbook.com. Retrieved 2019-10-05.
- Industrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7
- "Alcool caprylique secondaire". csst.qc.ca (in French). Retrieved 2019-10-05.
- Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.
- "Example of industrial valorisation of derivative products of Castor oil". OCL Journal. Retrieved 2019-10-05.
- "2-octanol, 123-96-6". thegoodscentscompany.com. Retrieved 2019-10-05.
- Fenaroli's Handbook of Flavor Ingredients, Fifth Edition George A. Burdock ; CRC Press, 3 déc. 2004 - 1864 pages, Page 1420
- Handbook of Flavor Ingredients, Volume 1 Giovanni Fenaroli (Prof. Dr.), Taylor & Francis, 1975 – page 443
- Industrial Alcohol Technology Handbook ; NPCS Board of Consultants & Engineers ; ASIA PACIFIC BUSINESS PRESS Inc., 2 oct. 2010 - p. 206 – Utilisations principales
- Industrial Solvents Handbook, Revised And Expanded Nicholas P. Cheremisinoff ; CRC Press, 15 avr. 2003 - 344 pages; pages 141
- Paint and Coating Testing Manual, ASTM International, page 396
- Chemistry of Tantalum and Niobium Fluoride Compounds; Anatoly Agulyansky ; Elsevier, 13 déc. 2004 - 408 pages; page 284
- 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
- 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
- Pesticide Synthesis Handbook ; Thomas A. Unger ; William Andrew, 31 déc. 1996 - 1104 pages; page 1043
- "Valorization of Castor Oil for Polymer Applications" (PDF). Archived from the original (PDF) on 2015-04-02. Retrieved 2015-03-13.
- "2-Octanol | 123-96-6 | C8H18O | T&J Chemicals". Speciality Chemicals Supply | T&J Chemicals. Retrieved 2018-09-17.
References
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