2-ethylhexyl acrylate

Structural formula
	Simplified structural formula - mixture of isomers
General
Surname	2-ethylhexyl acrylate
other names	2-ethylhexyl acrylic acid; Octyl acrylate; 2-propenoic acid 2-ethylhexyl ester;
Molecular formula	C 11 H 20 O 2
Brief description	colorless liquid with a sweet odor
External identifiers / databases
EC number	203-080-7
ECHA InfoCard	100.002.801
PubChem	7636
Wikidata	Q209383
properties
Molar mass	184.28 g mol −1
Physical state	liquid
density	0.89 g cm −3
Melting point	−90 ° C
boiling point	214 ° C; 91 ° C (13 hPa);
Vapor pressure	0.132 hPa (20 ° C); 1.33 hPa (50 ° C);
solubility	Slightly soluble in water (0.1 g l −1 at 25 ° C)
Refractive index	1.4332 (25 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 315-317-335-412
	P: 273-280-304 + 340 + 312-333 + 313
MAK	DFG / Switzerland: 5 ml m −3 or 38 mg m −3
	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-Ethylhexyl acrylate belongs to the group of acrylates . It is a colorless chemical compound that is liquid at room temperature and has a sweet odor.

Extraction and presentation

The present as a racemate 2-ethylhexyl acrylate is z. B. by esterification of acrylic acid with racemic 2-ethylhexanol in the presence of hydroquinone as a polymerization inhibitor and a strong acid, such as. B. methanesulfonic acid with toluene as an entrainer in a reactive distillation in high yield.

properties

Chemical properties

2-Ethylhexyl acrylate has a strong tendency to polymerize . The polymerization can be caused by light, peroxides , impurities or heat. The heat of polymerization is −78.2 kJ mol ⁻¹ or −424 kJ kg ⁻¹ . In combination with strong oxidizing agents it can cause violent reactions. The chemical, physical and toxicological properties can, however, be greatly modified by additives or stabilizers .

Safety-related parameters

2-Ethylhexyl acrylate is considered a flammable liquid. Flammable vapor-air mixtures can form above the flash point . The compound has a flash point of 86 ° C. The explosion range is between 0.8% by volume (60 g / m ³ ) as the lower explosion limit (LEL) and 6.0% by volume as the upper explosion limit (UEL). The lower explosion point is 77 ° C. The ignition temperature is 245 ° C. The substance therefore falls into temperature class T3.

use

Together with butyl acrylate, 2-ethylhexyl acrylate is one of the most important base monomers for the manufacture of acrylate adhesives. 2-Ethylhexyl acrylate can react to macromolecules with a molar mass of up to 200,000 g / mol through radical polymerization . In order to modify the properties of the resulting substance, other monomers such as vinyl acetate , methyl acrylate and styrene or molecules with functional groups can be added. The compound is also used as a reactive diluent in radical radiation curing .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on 2-ethylhexyl acrylate in the GESTIS substance database of the IFA , accessed on June 4, 2018(JavaScript required) .
↑ ^a ^b ^c ^d ^e Entry on (2-ethylhexyl) acrylate. In: Römpp Online . Georg Thieme Verlag, accessed on June 4, 2018.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-246.
↑ Entry on 2-ethylhexyl acrylate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 103-11-7 or 2-ethylhexyl acrylate ), accessed on November 2, 2015.
↑ Patent US2917538 : Process for the production of acrylic acid esters. Applied December 19, 1957 , published December 15, 1959 , Applicant: The Dow Chemical Co., Inventor: RL Carlyle. ‌
↑ Brandrup, J .; Immergut, EH; Grulke, EA; Abe, A .; Bloch, DR: Polymer Handbook , 4th Edition, Wiley-VCH 2003, ISBN 978-0-471-47936-9 , p. II / 369.
↑ ^a ^b ^c E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
↑ Bodo Müller, Walter Rath, Walter Rath: Formulation of adhesives and sealants. 1st edition. Vincentz Network, Hannover 2004, ISBN 3878707916 , p. 235 ( limited preview in Google book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on 2-ethylhexyl acrylate in the GESTIS substance database of the IFA , accessed on June 4, 2018(JavaScript required) .

[Roempp-2] Entry on (2-ethylhexyl) acrylate. In: Römpp Online . Georg Thieme Verlag, accessed on June 4, 2018.

[CRC90_3_246-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-246.

[CLP_100.002.801-4] Entry on 2-ethylhexyl acrylate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 103-11-7 or 2-ethylhexyl acrylate ), accessed on November 2, 2015.

[6] Patent US2917538 : Process for the production of acrylic acid esters. Applied December 19, 1957 , published December 15, 1959 , Applicant: The Dow Chemical Co., Inventor: RL Carlyle. ‌

[Polymer_Handbook-7] Brandrup, J .; Immergut, EH; Grulke, EA; Abe, A .; Bloch, DR: Polymer Handbook , 4th Edition, Wiley-VCH 2003, ISBN 978-0-471-47936-9 , p. II / 369.

[Brandes-8] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[Rathmüller-9] Bodo Müller, Walter Rath, Walter Rath: Formulation of adhesives and sealants. 1st edition. Vincentz Network, Hannover 2004, ISBN 3878707916 , p. 235 ( limited preview in Google book search).