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
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−1
Appearance	Colourless liquid with characteristic odour
Density	0.820 7 (g/cm3) (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)	1.23·10−4 atm-m3/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 [77 °F], 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.^[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

It is a precursor to 2-octyl cyanoacrylate, a version of superglue used as a wound closure adhesive.^[11] 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.^[12]

2-Octanol is also used as:

Flavor^[7]^[13]^[14]^[15]
low-volatility solvent : Diverses Resins (Paints & Coatings, Adhesives, Inks, etc.), Agrochemicals, Mineral Extraction, etc....^[16]^[17]^[18]^[19]
Defoaming agent : Pulp & Paper, Oil & Gas, Cement, Coatings, Coal, etc.
a frother in mineral flotation^[20]
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.),^[21]
Plasticizers (acrylates, maleates, etc.),
Pesticides: Dinocap ^[22]^[23]
Lubricants: Zinc dithiophosphate (ZDDP)
Fragrances (salicylate)
Used in the manufacturing of perfumes and disinfectant soaps^[24]
Used to prevent foaming and as a solvent for fats and waxes^[24]
Used to examine and control Essential Tremor and other types of involuntary neurological tremors^[24]

Notes

1 2 " 2-Octanol " on NIST/WebBook
↑ "Techniques de l'ingénieur : Solvants organiques". Archived from the original on 2015-04-02. Retrieved 2015-03-13.
1 2 " 2-Octanol " on ChemIDplus
1 2 3 4 5 6 7 8 9 10 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. Archived from the original on 2015-04-02. Retrieved 2019-10-05.
↑ Industrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7
1 2 "Alcool caprylique secondaire". csst.qc.ca (in French). Archived from the original on 2015-04-02. Retrieved 2019-10-05.
↑ Roger Adams, C. S. Marvel (1921). "Methyl-n-hexylcarbinol". Organic Syntheses. 1: 61. doi:10.15227/orgsyn.001.0061.
↑ 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.
↑ 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.
↑ "Summary of Safety and Effectiveness Data" (PDF). Food and Drug Administration. 1998. Archived from the original (PDF) on November 18, 2015.
↑ Perera, AG Nuwan; Tavarez, Melissa M. (2022). "2-Octyl Cyanoacrylate". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 30335326. Retrieved 2022-08-19.
↑ "2-octanol, 123-96-6". thegoodscentscompany.com. Archived from the original on 2006-06-05. 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.
1 2 3 "2-Octanol | 123-96-6 | C8H18O | T&J Chemicals". Speciality Chemicals Supply | T&J Chemicals. Retrieved 2018-09-17.

References

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

[NIST-1] 1 2 " 2-Octanol " on NIST/WebBook

[TechIngenieur-2] "Techniques de l'ingénieur : Solvants organiques". Archived from the original on 2015-04-02. Retrieved 2015-03-13.

[ChemIdPlus-3] 1 2 " 2-Octanol " on ChemIDplus

[GESTIS-4] 1 2 3 4 5 6 7 8 9 10 Record of 2-octanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2 February 2010.

[5] "2-Octanol | 4128-31-8". chemicalbook.com. Archived from the original on 2015-04-02. Retrieved 2019-10-05.

[IndSolvHandbook-6] Industrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7

[CSST-7] 1 2 "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.

[Ullmanns-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.

[fda-11] "Summary of Safety and Effectiveness Data" (PDF). Food and Drug Administration. 1998. Archived from the original (PDF) on November 18, 2015.

[12] Perera, AG Nuwan; Tavarez, Melissa M. (2022). "2-Octyl Cyanoacrylate". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 30335326. Retrieved 2022-08-19.

[13] "2-octanol, 123-96-6". thegoodscentscompany.com. Archived from the original on 2006-06-05. Retrieved 2019-10-05.

[14] Fenaroli's Handbook of Flavor Ingredients, Fifth Edition George A. Burdock; CRC Press, 3 déc. 2004 - 1864 pages, Page 1420

[15] Handbook of Flavor Ingredients, Volume 1 Giovanni Fenaroli (Prof. Dr.), Taylor & Francis, 1975 – page 443

[16] Industrial Alcohol Technology Handbook; NPCS Board of Consultants & Engineers; ASIA PACIFIC BUSINESS PRESS Inc., 2 oct. 2010 - p. 206 – Utilisations principales

[17] Industrial Solvents Handbook, Revised And Expanded Nicholas P. Cheremisinoff; CRC Press, 15 avr. 2003 - 344 pages; pages 141

[18] Paint and Coating Testing Manual, ASTM International, page 396

[19] Chemistry of Tantalum and Niobium Fluoride Compounds; Anatoly Agulyansky; Elsevier, 13 déc. 2004 - 408 pages; page 284

[20] 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

[21] 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

[22] Pesticide Synthesis Handbook; Thomas A. Unger; William Andrew, 31 déc. 1996 - 1104 pages; page 1043

[23] "Valorization of Castor Oil for Polymer Applications" (PDF). Archived from the original (PDF) on 2015-04-02. Retrieved 2015-03-13.

[oc-24] 1 2 3 "2-Octanol | 123-96-6 | C8H18O | T&J Chemicals". Speciality Chemicals Supply | T&J Chemicals. Retrieved 2018-09-17.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]

[17]

[18]

[19]

[20]

[21]

[22]

[23]

[24]

This page was redesigned at the edge.

2-Octanol

Production

Uses

See also

Notes

References