2-octanol

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Structural formula
Structural formula of 2-octanol
Simplified structural formula without stereochemistry
General
Surname 2-octanol
other names
  • Octan-2-ol
  • 2-octyl alcohol
  • 2-caprylic alcohol
  • Hexylmethyl carbinol
Molecular formula C 8 H 18 O
Brief description

colorless liquid with an aromatic odor

External identifiers / databases
CAS number
  • 123-96-6 (unspecified)
  • 4128-31-8 ( DL -2-octanol)
  • 5978-70-1 ( L -2-octanol)
  • 6169-06-8 ( D -2-octanol)
PubChem 20083
Wikidata Q10844270
properties
Molar mass 130.23 g mol −1
Physical state

liquid

density

0.82 g cm −3

Melting point
  • −32 ° C
  • −38.6 ° C (±)
boiling point

180 ° C

Vapor pressure

0.323 hPa (25 ° C)

solubility
  • sparingly soluble in water (1.12 g l −1 at 25 ° C)
  • miscible with diethyl ether, acetone, ethanol, most organic solvents, aromatic and aliphatic hydrocarbons
Refractive index

1.4260 (20 ° C)

safety instructions
GHS labeling of hazardous substances
05 - Corrosive

danger

H and P phrases H: 318
P: 280-305 + 351 + 338 + 310
Toxicological data

6100 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-Octanol is a chemical compound from the group of alcohols . It is also a chiral secondary alcohol.

Isomers

Whenever "2-octanol" is mentioned without a prefix in this article or in the scientific literature , the racemate (±) -2-octanol [synonym: ( RS ) -2-octanol] is meant, a 1: 1 mixture of ( R ) -2-octanol and ( S ) -2-octanol. In addition to 2-octanol, there are structural isomers of octanol, namely 1-octanol , 3-octanol and 4-octanol .

Occurrence

2-octanol occurs naturally in geranium oil, mint, and lavender.

Extraction and presentation

2-Octanol can be obtained by alkaline hydrolysis of castor oil to sodium ricinolate and subsequent pyrolysis , which also produces 2-octanone and hydrogen . As a result, the technical product contains around 15% 2-octanone.

properties

2-Octanol is a flammable, hardly inflammable, little volatile, colorless liquid with an aromatic odor that is sparingly soluble in water. It can be esterified with acids and a suitable catalyst , oxidized to ketones and dehydrated to olefins .

Biological importance

In addition to 1-octanol , 2-octanol is an alarm pheromone for honeybees .

use

2-Octanol is used in flavors, paints and coatings, antifoam agents , as a low-volatility solvent , in lubricants, fuels, paints and varnishes. It is used as a defoamer in wetting agents and is an intermediate product in the manufacture of surfactants , cosmetic emollients and plasticizers . It is also used as a starting material in the synthesis of pharmaceutical compounds and piperine derivatives. It is also considered an alternative to 2-ethylhexanol .

safety instructions

The vapors of 2-octanol can form an explosive mixture with air ( flash point 71 ° C, ignition temperature 265 ° C).

Individual evidence

  1. ↑ a b c d e f g h i j k Entry on 2-octanol in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  2. ↑ Shmuel Yannai: Dictionary of Food Compounds with CD-ROM, Second Edition . CRC Press, 2012, ISBN 978-1-4200-8351-4 , pp. 1440 ( limited preview in Google Book search).
  3. ↑ a b c d data sheet (±) -2-octanol, 98% from AlfaAesar, accessed on July 9, 2016 ( PDF )(JavaScript required) .
  4. ^ A b c Philip H. Howard: Handbook of Environmental Fate and Exposure Data for Organic Chemicals . CRC Press, 1993, ISBN 978-0-87371-413-6 , pp. 469 ( limited preview in Google Book search).
  5. ↑ Olfactory response characteristics and tuning structure of placodes in the honey bee Apis mellifera L WM Getz, RP Akers Apidologie, 1993 Vol 24 pp. 195-217