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2-Ethylhexyl acrylate
2-Ethylhexyl acrylate is a colorless liquid acrylate used in the making of paints, plastics and adhesives. It has an odor that has been variously described as pleasant or acrid and musty.
| Column 1 | Column 2 |
|---|---|
| Preferred IUPAC name | |
| 2-Ethylhexyl prop-2-enoate | |
| Other names | |
| 2-Ethylhexyl acrylate2-EHA | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}103-11-7 Y |
| 3D model (JSmol) | Interactive image |
| ChEBI | CHEBI:82465 |
| ChemSpider | 7354 |
| ECHA InfoCard | 100.002.801 |
| EC Number | 203-080-7 |
| KEGG | C19420 |
| PubChem CID | 7636 |
| UNII | HR49R9S6XG Y |
| CompTox Dashboard (EPA) | DTXSID9025297 |
| InChI | |
| InChI=1S/C11H20O2/c1-4-7-8-10(5-2)9-13-11(12)6-3/h6,10H,3-5,7-9H2,1-2H3Key: GOXQRTZXKQZDDN-UHFFFAOYSA-N | |
| SMILES | |
| CCCCC(CC)COC(=O)C=C | |
| Chemical formula | C11H20O2 |
| Molar mass | 184.279 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.885 g/mL |
| Melting point | −90 °C (−130 °F; 183 K) |
| Boiling point | 215–219 °C (419–426 °F; 488–492 K) |
| Solubility in water | organic solvents |
| GHS labelling: | |
| Pictograms | |
| Signal word | Warning |
| Hazard statements | H315, H317, H335, H412 |
| Precautionary statements | P273, P280, P304+P340+P312, P333+P313 |
| Flash point | 82 °C; 180 °F; 355 K |
| Autoignitiontemperature | 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 used in the making of paints, plastics and adhesives. It has an odor that has been variously described as pleasant or acrid and musty.
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.
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.
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.
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