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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1719322
ChEBI	CHEBI:37869;
ChEMBL	ChEMBL510068;
ChemSpider	1892;
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 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	130.231 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)	1.23E-04 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, P370+P378, P391, P403+P235, P501
Flash point	71 °C (160 °F; 344 K)
Autoignition; temperature	265 °C (509 °F; 538 K)
Explosive limits	0.8 vol. % - 7,4 vol.%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	>3.2 g/kg (rat, oral); 4 g/kg (mouse, oral)
	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. 2-Octanol can be a biobased alternative of 2-ethylhexanol and its derivates in numerous applications.

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]

Notes

^ ^a ^b " 2-Octanol " on NIST/WebBook
^ Techniques de l’ingénieur : Solvants organiques
^ ^a ^b " 2-Octanol " on ChemIDplus
^ ^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.
^ "2-Octanol | 4128-31-8". chemicalbook.com. Retrieved 2019-10-05.{{cite web}}: CS1 maint: url-status (link)
^ Industrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7
^ ^a ^b "Alcool caprylique secondaire". csst.qc.ca (in French). Retrieved 2019-10-05.{{cite web}}: CS1 maint: url-status (link)
^ Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523. ISBN 978-3527306732.
^ "Example of industrial valorisation of derivative products of Castor oil". OCL Journal. Retrieved 2019-10-05.{{cite web}}: CS1 maint: url-status (link)
^ "2-octanol, 123-96-6". thegoodscentscompany.com. Retrieved 2019-10-05.{{cite web}}: CS1 maint: url-status (link)
^ 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.
^ ^a ^b ^c "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] " 2-Octanol " on NIST/WebBook

[TechIngenieur-2] Techniques de l’ingénieur : Solvants organiques

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

[GESTIS-4] ^ ^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.

[5] "2-Octanol | 4128-31-8". chemicalbook.com. Retrieved 2019-10-05.{{cite web}}: CS1 maint: url-status (link)

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

[CSST-7] "Alcool caprylique secondaire". csst.qc.ca (in French). Retrieved 2019-10-05.{{cite web}}: CS1 maint: url-status (link)

[Ullmanns-8] Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523. ISBN 978-3527306732.

[9] "Example of industrial valorisation of derivative products of Castor oil". OCL Journal. Retrieved 2019-10-05.{{cite web}}: CS1 maint: url-status (link)

[10] "2-octanol, 123-96-6". thegoodscentscompany.com. Retrieved 2019-10-05.{{cite web}}: CS1 maint: url-status (link)

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

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

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

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

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

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

[17] 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

[18] 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

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

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

[:0-21] "2-Octanol | 123-96-6 | C8H18O | T&J Chemicals". Speciality Chemicals Supply | T&J Chemicals. Retrieved 2018-09-17.

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Manufacturing

Uses

See also

Notes

References