2-ethylhexyl acetate

Structural formula
Structural formula without stereochemistry
General
Surname	2-ethylhexyl acetate
other names	2-Ethyhexylethanoate ( IUPAC ) 2-ethylhexyl acetate Ethanoic acid 2-ethylhexyl ester Isooctyl acetate
Molecular formula	C 10 H 20 O 2
Brief description	colorless liquid with a pleasant odor
External identifiers / databases
CAS number 103-09-3 EC number 203-079-1 ECHA InfoCard 100.002.800 PubChem 7635 Wikidata Q5656537
properties
Molar mass	172.27 g mol −1
Physical state	liquid
density	0.88 g cm −3 (20 ° C)
Melting point	−93 ° C
boiling point	199 ° C
Vapor pressure	0.28 h Pa (20 ° C)
solubility	practically insoluble in water (0.088 g l −1 at 25 ° C) miscible with most organic solvents
Refractive index	1.418 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315 P: 264-280-302 + 352-332 + 313-362
Toxicological data	3000 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

Acetic acid 2-ethylhexyl ester (according to IUPAC nomenclature: 2-ethylhexyl ethanoate , also known as 2-ethylhexyl acetate ) is an organochemical compound from the group of carboxylic acid esters .

Extraction and presentation

2-ethylhexyl acetate is produced on an industrial scale by transesterification of methyl acetate with 2-ethylhexanol at temperatures around 80 ° C. on acidic ion exchange resins .

properties

Physical Properties

2-Ethylhexyl acetate has a relative gas density of 5.93 (density ratio to dry air at the same temperature and pressure ) and a relative density of the steam-air mixture of 1.00 (density ratio to dry air at 20 ° C and normal pressure ). In addition, 2-ethylhexyl acetate has a vapor pressure of 0.28 hPa at 20 ° C.

Chemical properties

Acetic acid-2-ethylhexyl ester is a hardly inflammable liquid from the group of carboxylic acid esters . It is difficult or very difficult to volatilize and practically insoluble in water. In addition, 2-ethylhexyl acetate is heavier than water. Dangerous reactions occur on contact with alkali metals or strong alkalis and oxidizing agents . In addition, 2-methyl-1-pentanol occurs in two enantiomeric forms , since it has a center of chirality on the C2 carbon of the alkyl radical . Thus, there exist (R) -2-ethylhexyl acetate and (S) -2-ethylhexyl acetate. A 1: 1 mixture of the two enantiomers is called a racemate .

use

2-Ethylhexyl acetate is used as a high-boiling, hydrophobic solvent for cellulose nitrate and numerous natural and synthetic resins . It is also used in brush, spray and dip stoving lacquers. Here it is used to improve the flow and film formation. Furthermore, 2-ethylhexyl acetate is also used as an additive in cleaning , paint stripping and cleaning.

safety instructions

The vapors of 2-ethylhexyl acetate can form explosive mixtures with air when the substance is heated above the flash point. The substance is mainly absorbed through the respiratory tract. This can cause irritation to the mucous membranes and the skin. There is also the risk of a disturbance in the central nervous system. No further chronic diseases were found. 2-Ethylhexyl acetate is assigned to explosion group IIA and has a lower explosion limit of approx. 1.1% by volume and an upper explosion limit of approx. 7.5% by volume. With a flash point of 71 ° C, 2-ethylhexyl acetate is considered flame-retardant. The ignition temperature is 230 ° C. The substance therefore falls into temperature class T3.

Acetic acid 2-ethylhexyl ester was included in the EU's ongoing action plan ( CoRAP ) in 2013 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of 2-ethylhexyl acetate were concerns regarding consumer use and widespread use as well as the dangers arising from a possible assignment to the group of CMR substances. The re-evaluation took place from 2015 and was carried out by Belgium . A final report was then published.

Individual evidence

1. ↑ ^{a b c d e f g h i j k l m} Entry on 2-ethylhexyl acetate in the GESTIS substance database of the IFA , accessed on February 12, 2019(JavaScript required) .
2. ↑ ^{a b c} Entry on 2-ethylhexyl acetate. In: Römpp Online . Georg Thieme Verlag, accessed on February 12, 2019 .
3. ↑ Data sheet 2-Ethylhexyl acetate, ≥99% from Sigma-Aldrich , accessed on February 12, 2019 ( PDF ).
4. ↑ Lina Yin, Dazhi Wang, Fengzuo Qu, Lin Jia, Shaoyin Zhang: Synthesis of 2-Ethylhexyl Acetate by Transesterification of Methyl Acetate with 2-Ethylhexanol. In: Asian Journal of Chemistry. 27, 2015, p. 2861, doi : 10.14233 / ajchem.2015.18263 .
5. ↑ 2-ethylhexyl acetate. In: BASF Technical Data Sheet. BASF SE, March 2008, accessed on February 12, 2019 . 
6. ↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
7. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 2-ethylhexyl acetate , accessed on May 2, 2020.