Hydroxyethyl acrylate
Organic chemical-monomer
From Wikipedia, the free encyclopedia
Hydroxyethyl acrylate is the organic compound with the formula CH2=CHCO2CH2CH2OH. It is a colorless viscous liquid. The compound has dual functionality: a polymerizable acrylic and a hydroxy group. It is a monomer used to make emulsion polymers along with other monomers and the resultant resins are used in coatings, sealants, adhesives and elastomers and other applications.[2][3]
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| Names | |
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| IUPAC name
2-hydroxyethyl prop-2-enoate | |
| Other names
HEA | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.011.322 |
| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 2927 1760 |
CompTox Dashboard (EPA) |
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| Properties | |
| C5H8O3 | |
| Molar mass | 116.116 g·mol−1 |
| Appearance | colorless liquid |
| Density | 1.106 |
| Boiling point | 220 °C (428 °F; 493 K) |
| Hazards | |
| GHS labelling:[1] | |
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| Danger | |
| H311, H314, H317, H400 | |
| P260, P264, P272, P273, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P333+P313, P361+P364, P362+P364, P363, P391, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
A number of patents and synthesis papers describe its preparation. A traditional manufacturing process calls for the reaction of ethylene oxide with acrylic acid in the presence of a metal catalyst.[4]
Properties
The material is a water-white liquid with a mild but pungent ester like odor.[5] It has a low freezing point.
Applications
The most common use for the material is to be copolymerized with other acrylate and methacrylate monomers to make emulsion and other polymers including hydrogels.[6][7][8][9] Modification of rubbers and similar compounds is also a use for the material.[10] The resultant polymers may be used to manufacture pressure-sensitive adhesives.[11]