2-nonanol

Structural formula
( R ) -2-nonanol (top) and ( S ) -2-nonanol (bottom)
General
Surname	2-nonanol
other names	Nonan-2-ol Heptyl methyl carbinol
Molecular formula	C 9 H 20 O
Brief description	colorless liquid
External identifiers / databases
CAS number 628-99-9 ( racemate ) 70419-06-6 [( S ) - (+) - 2-nonanol] 70419-07-7 [( R ) - (-) - 2-nonanol] EC number 211-065-1 ECHA InfoCard 100.010.060 PubChem 12367 Wikidata Q4596913
properties
Molar mass	144.26 g mol −1
Physical state	liquid
density	0.82 g cm −3 (racemate)
Melting point	−35 ° C (racemate)
boiling point	198 ° C (racemate)
solubility	almost insoluble in water
Refractive index	1,429
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
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-Nonanol is a naturally occurring chemical compound from the group of aliphatic alcohols . In addition to the two enantiomers ( R ) -2-nonanol and ( S ) -2-nonanol, there are further structural isomers, for example 1-nonanol , 3-nonanol and 4-nonanol .

Occurrence

Honey bee ( Apis mellifera )

Nonan-2-ol is found in various vegetable oils, e.g. For example in the oil from ginger ( Zingiber officinale ), and in the secretions of a number of insects . The alcohol is a pheromone of the honey bee .

properties

There are two stereoisomers of 2-nonanol . However, only the racemate is of practical importance . This has a melting point of −35 ° C. The boiling point under normal pressure is 198 ° C. According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in Pa, T in ° C) with A = 10.179, B = 1961.437 and C = 189.330 in the temperature range from 253 to 353 K. The critical temperature is 377 ° C, the critical pressure 25.3 bar and the critical volume 0.575 l · mol ⁻¹ .

The vapors of the hardly flammable liquid (flash point 82 ° C) can form explosive mixtures with air when the substance is heated above its flash point.

use

Nonan-2-ol - like the isomeric nonan-3-ol and nonan-4-ol - is used as a component of perfumes and as a flavoring in foods such as baked goods.

Individual evidence

1. ↑ ^{a b c d} Entry on 2-nonanol in the GESTIS substance database of the IFA , accessed on July 24, 2013(JavaScript required) .
2. ↑ ^{a b c d e f} Data sheet 2-nonanol for synthesis (PDF) from Merck , accessed on July 24, 2013.
3. ↑ ^{a b} entry on nonanols. In: Römpp Online . Georg Thieme Verlag, accessed on July 25, 2013.
4. ↑ Ellis, LM; Reid, EE: The Preparation and Properties of A Double Series of Aliphatic Mercaptans in J. Am. Chem. Soc. 54 (1932) 1674-1687, doi : 10.1021 / ja01343a067 .
5. ↑ N'Guimbi, J .; Berro, C .; Mokbel, I .; Rauzy, E .; Jose, J .: Experimental vapor pressure of 13 secondary and ternary alcohols - correlation and prediction by group contribution method in Fluid Phase Equilibria 162 (1999) 143-158, doi : 10.1016 / S0378-3812 (99) 00168-5 .
6. ↑ Gude, M .; Teja, AS: Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols in J. Chem. Eng. Data 40 (1995) 1025-1036, doi : 10.1021 / je00021a001 .