2-Octanol

2-Octanol
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)	1.23E-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, 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.

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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]

2-Octanol is mainly used as:

Flavor^[7]^[11]^[12]^[13]
low-volatility solvent : Diverses Resins (Paints & Coatings, Adhesives, Inks, etc.), Agrochemicals, Mineral Extraction, etc....^[14]^[15]^[16]^[17]
Defoaming agent : Pulp & Paper, Oil & Gas, Cement, Coatings, Coal, etc.
a frother in mineral flotation^[18]
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.),^[19]
Plasticizers (acrylates, maleates, etc.),
Pesticides: Dinocap ^[20]^[21]
Lubricants: Zinc dithiophosphate (ZDDP)
Fragrances (salicylate)
Used in the manufacturing of perfumes and disinfectant soaps^[22]
Used to prevent foaming and as a solvent for fats and waxes^[22]
Used to examine and control Essential Tremor and other types of involuntary neurological tremors^[22]

1-Octanol

[1]
" 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]
" 2-Octanol " on ChemIDplus
[4]
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.
[6]
Industrial Solvents Handbook, Revised And Expanded by Nicholas P. Cheremisinoff – page 7
[7]
"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]
"2-Octanol | 123-96-6 | C8H18O | T&J Chemicals". Speciality Chemicals Supply | T&J Chemicals. Retrieved 2018-09-17.

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

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

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

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

[GESTIS-4] [4]
Record of 2-octanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2 February 2010.

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

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

[CSST-7] [7]
"Alcool caprylique secondaire". csst.qc.ca (in French). Archived from the original on 2015-04-02. Retrieved 2019-10-05.

[8] [8]
Roger Adams, C. S. Marvel (1921). "Methyl-n-hexylcarbinol". Organic Syntheses. 1: 61. doi:10.15227/orgsyn.001.0061.

[Ullmanns-9] [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] [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] [11]
"2-octanol, 123-96-6". thegoodscentscompany.com. Archived from the original on 2006-06-05. Retrieved 2019-10-05.

[12] [12]
Fenaroli's Handbook of Flavor Ingredients, Fifth Edition George A. Burdock ; CRC Press, 3 déc. 2004 - 1864 pages, Page 1420

[13] [13]
Handbook of Flavor Ingredients, Volume 1 Giovanni Fenaroli (Prof. Dr.), Taylor & Francis, 1975 – page 443

[14] [14]
Industrial Alcohol Technology Handbook ; NPCS Board of Consultants & Engineers ; ASIA PACIFIC BUSINESS PRESS Inc., 2 oct. 2010 - p. 206 – Utilisations principales

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

[16] [16]
Paint and Coating Testing Manual, ASTM International, page 396

[17] [17]
Chemistry of Tantalum and Niobium Fluoride Compounds; Anatoly Agulyansky ; Elsevier, 13 déc. 2004 - 408 pages; page 284

[18] [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] [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] [20]
Pesticide Synthesis Handbook ; Thomas A. Unger ; William Andrew, 31 déc. 1996 - 1104 pages; page 1043

[21] [21]
"Valorization of Castor Oil for Polymer Applications" (PDF). Archived from the original (PDF) on 2015-04-02. Retrieved 2015-03-13.

[:0-22] [22]
"2-Octanol | 123-96-6 | C8H18O | T&J Chemicals". Speciality Chemicals Supply | T&J Chemicals. Retrieved 2018-09-17.

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[9]

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[17]

[18]

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[22]

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2-Octanol

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Production

Uses

See also

Notes

References

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^Y
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^Y
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^[1]
Density	0.820 7 (g/cm³) (20°C)^[2]
Melting point	−38 °C (−36 °F; 235 K)^[3]
Boiling point	178.5 °C (353.3 °F; 451.6 K)^[3]
Solubility in water	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 (k_H)	1.23E-04 atm-m³/mol^[4]
Refractive index (n_D)	1.426 (20 °C)^[5]
Viscosity	6.2 cP^[6]
Thermochemistry
Heat capacity (C)	330.1 (J/mol*K) (298.5K)^[1]
Hazards
Occupational safety and health (OHS/OSH):
Eye hazards	2^[4]
Skin hazards	2^[4]
GHS labelling:^[4]
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)^[4]
Autoignition temperature	265 °C (509 °F; 538 K)^[4]
Explosive limits	0.8 % v/v (lower) 7.4 % v/v (upper)^[4]
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	>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). Infobox references