2-ethylhexane-1,3-diol

Structural formula
Structural formula without information on stereoisomerism
General
Surname	2-ethylhexane-1,3-diol
other names	3-hydroxymethyl- n -heptan-4-ol Ethylhexylene glycol Ethylhexanediol Ethohexadiol Octylene glycol Octylene glycol ETHYL HEXANEDIOL ( INCI ) Rutgers 612 Skecto-go
Molecular formula	C 8 H 18 O 2
Brief description	colorless and odorless liquid
External identifiers / databases
CAS number 94-96-2 EC number 202-377-9 ECHA InfoCard 100.002.162 PubChem 7211 ChemSpider 21106534 DrugBank DB13826 Wikidata Q992192
properties
Molar mass	146.22 g mol −1
Physical state	liquid
density	0.94 g cm −3
Melting point	−40 ° C
boiling point	243 ° C
Vapor pressure	<0.01 hPa (20 ° C)
solubility	soluble in water (42 g l −1 at 20 ° C) unlimited in alcohols, esters, ketones, ethers
Refractive index	1.4497
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 318 P: 280-305 + 351 + 338
Toxicological data	1400 mg kg −1 ( LD 50 ,  rat ,  oral ) 2000 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
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-Ethylhexan-1,3-diol (also simplified ethylhexanediol ) is a mixture of several isomeric organic chemical compounds from the group of alkanediols .

Stereochemistry

The molecule has two stereocenters , on the 2nd and 3rd carbon, so that there are four stereoisomeric compounds of ethylhexanediol:

• (2 R , 3 R ) -2-ethylhexane-1,3-diol
• (2 S , 3 S ) -2-ethylhexane-1,3-diol
• (2 R , 3 S ) -2-ethylhexane-1,3-diol
• (2 S , 3 R ) -2-ethylhexane-1,3-diol

presentation

Ethylhexanediol can be synthesized by condensation of butanal with magnesium aluminum ethoxide and subsequent hydrolysis of the ester formed . Another approach is the hydrogenation of butyraldol ( 2-ethyl-3-hydroxyhexanal ). Starting compounds of industrial production are chemicals of the petrochemical industry .

use

It is used as a mixture of the four stereoisomeric forms as a repellent against insects (especially effective against Aedes ), cooling lubricant and as an emollient .

See also

• 2-ethylhexanol

Individual evidence

1. ↑ Entry on ETHYL HEXANEDIOL in the CosIng database of the EU Commission, accessed on December 28, 2019.
2. ↑ ^{a b c d e f g h i j k} Entry on 2-ethylhexane-1,3-diol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
3. ↑ ^{a b c} Werner Baumann, Thomas Rothardt: printing chemicals . Springer, Berlin / Heidelberg 1999, ISBN 3-540-66046-1 , pp. 935 ( limited preview in Google Book search).
4. ↑ Entry on 2-ethylhexane-1,3-diol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Military Preventive Medicine: Mobilization and Deployment, Vol 1.Chapter 22: Personal Protection Measures Against Arthropods , p. 508.