2-Ethylhexyl acrylate

Names
Preferred IUPAC name 2-Ethylhexyl prop-2-enoate
Other names 2-Ethylhexyl acrylate 2-EHA
Identifiers
CAS Number	103-11-7 Y
3D model (JSmol)	Interactive image
ECHA InfoCard	100.002.801
PubChem CID	7636
UNII	HR49R9S6XG Y
CompTox Dashboard (EPA)	DTXSID9025297
SMILES CCCCC(CC)COC(=O)C=C
Properties
Chemical formula	C11H20O2
Molar mass	184.279 g·mol−1
Density	0.885 g/mL
Melting point	−90 °C (−130 °F; 183 K)
Boiling point	215–219 °C (419–426 °F; 488–492 K)
Hazards
GHS labelling:
Pictograms	[1]
Signal word	Warning
Hazard statements	H315, H317, H335, H412[1]
Precautionary statements	P273, P280, P304+P340+P312, P333+P313[1]
Flash point	82 °C; 180 °F; 355 K
Autoignition temperature	258 °C; 496 °F; 531 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Ethylhexyl acrylate is a colorless liquid acrylate with a pleasant odor, used in the making of paints, plastics^[2] and adhesives.

Preparation

Racemic 2-ethylhexyl acrylate can be prepared with a high yield by esterification of acrylic acid with racemic 2-ethylhexanol in the presence of hydroquinone as a polymerization inhibitor and a strong acid such as methanesulfonic acid by reactive distillation using toluene as an azeotroping agent.^[3]

Properties

2-Ethylhexyl acrylate polymerizes easily. The polymerization can be initiated by light, peroxides, heat, or contaminants. It can react violently when combined with strong oxidants and can form explosive mixtures with air at temperatures above 82 °C (180 °F). The chemical, physical, and toxicological properties, however, can be greatly modified by additives or stabilizers.

Use

2-Ethylhexyl acrylate and butyl acrylate are the major base monomers for the preparation of acrylate adhesives. 2-Ethylhexyl acrylate can react by free-radical polymerization to form macromolecules having a molecular weight of up to 200,000 g/mol. Other monomers such as vinyl acetate, methyl acrylate, and styrene may be copolymerized to modify the properties of the resulting polymer.^[4]