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2-Octanol
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2-Octanol.svg Skeletal formula Octan-2-ol 2-Octanol2-Octyl alcohol1-Methyl-1-heptanolsec-Capryl alcoholMethylhexylcarbinolsec-Caprylic alcohol correct CAS 123-96-6 correct FDA 66B0DD5E40 204-667-0 RH0795000 510068 20083 37869 131016 1719322 18920 CC(O)CCCCCC 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) IMPUPYZMUDSKSF-UHFFFAOYAA 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) IMPUPYZMUDSKSF-UHFFFAOYSA-N 8 18 1 0.820 7 (g/cm3) (20°C)http://www.techniques-ingenieur.fr/res/media/docbase/table/sl2838491-web/SL2838491TBL-web.xml Techniques de l'ingénieur : Solvants organiques 2015-03-13 2015-04-02 https://web.archive.org/web/20150402160224/http://www.techniques-ingenieur.fr/res/media/docbase/table/sl2838491-web/SL2838491TBL-web.xml dead 6.2 cPIndustrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7 -38 " 2-Octanol " on ChemIDplus 178.5 Colourless liquid with characteristic odour" 2-Octanol " on NIST/WebBook 1.120 g/L22280 2-octanol 2 February 2010 0.031 mbar (20 °C) 0.11 mbar (30 °C)0.9 mbar (50 °C) 1.23·10−4 atm-m3/mol 1.426 (20 °C)http://www.chemicalbook.com/ChemicalProductProperty_EN_CB3272125.htm 2-Octanol 4128-31-8 chemicalbook.com 2019-10-05 live https://web.archive.org/web/20150402135208/http://www.chemicalbook.com/ChemicalProductProperty_EN_CB3272125.htm 2015-04-02 2.9 330.1 (J/mol*K) (298.5K) 02 07 09 Warning 210 233 240 241 242 243 273 280 303+361+353 370+378 391 403+235 501 305+351+338 226 315 319 411 412 2 2 71 265 0.8 % v/v (lower) 7.4 % v/v (upper) 1 2 0 >3.2 g/kg (rat, oral)4 g/kg (mouse, oral)http://www.csst.qc.ca/prevention/reptox/pages/fiche-complete.aspx?no_produit=52472&nom=Octanol-2 Alcool caprylique secondaire csst.qc.ca fr 2019-10-05 live https://web.archive.org/web/20150402115434/http://www.csst.qc.ca/prevention/reptox/pages/fiche-complete.aspx?no_produit=52472&nom=Octanol-2 2015-04-02 Flinn Scientific
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.10.15227/orgsyn.001.0061 free Methyl-n-hexylcarbinol Organic Syntheses 1921 1 61 Roger Adams, C. S. Marvel The coproduct is a mixture of sebacic acid ((C8H16CO2H)2). Castor oil, which consists mainly of triglycerides of ricinoleic acid, is the main feedstock. 10.1002/14356007.a08_523.pub3 Dicarboxylic Acids, Aliphatic 2014 Cornils Boy Lappe Peter 3527306730http://www.ocl-journal.org/articles/ocl/abs/2009/04/ocl2009164p211/ocl2009164p211.html Example of Industrial Valorisation of Derivative Products of Castor Oil 2009 OCL Journal 10.1051/ocl.2009.0276 2019-10-05 live https://web.archive.org/web/20150924054657/http://www.ocl-journal.org/articles/ocl/abs/2009/04/ocl2009164p211/ocl2009164p211.html 2015-09-24 Borg Patrick Lê Guillaume Lebrun Stéphanie Pées Bernard Oléagineux, Corps Gras, Lipides 16 4–5–6 211–214 free
Uses
It is a precursor to 2-octyl cyanoacrylate, a version of superglue used as a wound closure adhesive.http://www.accessdata.fda.gov/cdrh_docs/pdf/P960052b.pdf https://web.archive.org/web/20151118095205/http://www.accessdata.fda.gov/cdrh_docs/pdf/P960052b.pdf dead November 18, 2015 Summary of Safety and Effectiveness Data Food and Drug Administration 1998 It is closely related to octyl cyanoacrylate. The use of 2-octyl cyanoacrylate was approved in 1998; offered as an alternative to stitches, sutures, and or adhesive strips.Perera AG Nuwan 2-Octyl Cyanoacrylate 2022 https://www.ncbi.nlm.nih.gov/books/NBK532293/ StatPearls Treasure Island (FL) StatPearls Publishing 30335326 2022-08-19 Tavarez Melissa M.
2-Octanol is also used as:
Flavorhttp://www.thegoodscentscompany.com/data/rw1024631.html 2-octanol, 123-96-6 thegoodscentscompany.com 2019-10-05 live https://web.archive.org/web/20060605032514/http://www.thegoodscentscompany.com/data/rw1024631.html 2006-06-05Fenaroli's Handbook of Flavor Ingredients, Fifth Edition George A. Burdock; CRC Press, 3 déc. 2004 - 1864 pages, Page 1420Handbook of Flavor Ingredients, Volume 1 Giovanni Fenaroli (Prof. Dr.), Taylor & Francis, 1975 – page 443
low-volatility solvent : Diverses Resins (Paints & Coatings, Adhesives, Inks, etc.), Agrochemicals, Mineral Extraction, etc....Industrial Alcohol Technology Handbook; NPCS Board of Consultants & Engineers; ASIA PACIFIC BUSINESS PRESS Inc., 2 oct. 2010 - p. 206 – Utilisations principalesIndustrial Solvents Handbook, Revised And Expanded Nicholas P. Cheremisinoff; CRC Press, 15 avr. 2003 - 344 pages; pages 141Paint and Coating Testing Manual, ASTM International, page 396Chemistry of Tantalum and Niobium Fluoride Compounds; Anatoly Agulyansky; Elsevier, 13 déc. 2004 - 408 pages; page 284
Defoaming agent : Pulp & Paper, Oil & Gas, Cement, Coatings, Coal, etc.
a frother in mineral flotationFrothing in Flotation II: Recent Advances in Coal Processing, Volume 2; Janusz Laskowski, E T Woodburn; CRC Press, 21 oct. 1998 - 336 pages; page 19
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.),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
Plasticizers (acrylates, maleates, etc.),
Pesticides: Dinocap Pesticide Synthesis Handbook; Thomas A. Unger; William Andrew, 31 déc. 1996 - 1104 pages; page 1043http://www.crops2industry.eu/images/pdf/bordeaux/10.%20ARKEMA_18-2-11.pdf Valorization of Castor Oil for Polymer Applications 2015-03-13 https://web.archive.org/web/20150402103214/http://www.crops2industry.eu/images/pdf/bordeaux/10.%20ARKEMA_18-2-11.pdf 2015-04-02 dead
Lubricants: Zinc dithiophosphate (ZDDP)
Fragrances (salicylate)
Used in the manufacturing of perfumes and disinfectant soapshttps://www.tjchem.com.sg/2-octanol 2-Octanol 123-96-6 C8H18O T&J Chemicals Speciality Chemicals Supply T&J Chemicals en 2018-09-17
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
References
http://www.agrobiobase.com/fr/annuaire/bioproduits/chimie-formulation-synthese/2-octano
Category:Fatty alcohols
Category:Octanols