Octyldodecanol

Octyldodecanol is a branched-chain primary alcohol used as the isomer 2-octyl-1-dodecanol in cosmetics such as lipstick,[2] or as an anti-blooming agent in facepowder.[3] It is a medium spreading emollient, with equilibrium spreading pressure of 17.0 dyne/cm.[4] Octyldodecanol is in the class of Guerbet alcohols, because it has the branch at the β position.[5] Compared to arachidyl alcohol, the linear alcohol of the same molecular weight, it has a lower melting point, yet retains low volatility.[5]

Octyldodecanol
Names
IUPAC name
2-Octyldodecan-1-ol[1]
Other names
2-Octyl-1-dodecanol, 2-Octyldodecanol, Eutanol G, Guerbet C20, Isofol 20, Kalcohl 200G
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.023.857
EC Number
  • 226-242-9
KEGG
UNII
  • InChI=1S/C20H42O/c1-3-5-7-9-11-12-14-16-18-20(19-21)17-15-13-10-8-6-4-2/h20-21H,3-19H2,1-2H3
    Key: LEACJMVNYZDSKR-UHFFFAOYSA-N
  • CCCCCCCCCCC(CCCCCCCC)CO
Properties
C20H42O
Molar mass 298.555 g·mol−1
Appearance yellow oil
Density 0.84
Melting point 1 °C (34 °F; 274 K)
Boiling point 382 °C (720 °F; 655 K)
1.454
Hazards
Flash point 113 °C (235 °F; 386 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Production

2-Octyldodecanol is produced by the Guerbet condensation of decyl alcohol.[6]

Reactions

When octyldodecanol is melted with an alkali it yields octyldodecanoic acid by a dehydrogenation reaction.[5]

References
  1. "2-Octyl-1-dodecanol".
  2. Milne, G. W. A. (2005). Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties. John Wiley & Sons. p. 456. ISBN 9780471736615.
  3. Williams, S. D. (1996). Chemistry and Technology of the Cosmetics and Toiletries Industry. Springer Science & Business Media. p. 164. ISBN 9780751403343.
  4. Kroke, H. P. (April 1978). "Oily components in cosmetics from a European view". Journal of the American Oil Chemists' Society. 55 (4): 444–446. doi:10.1007/BF02911910. S2CID 85148769.
  5. O'Lenick, Anthony J. (July 2001). "Guerbet chemistry". Journal of Surfactants and Detergents. 4 (3): 311–315. doi:10.1007/s11743-001-0185-1. S2CID 195343946.
  6. Williams (1996), p. 26.
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