Hydroxyethyl acrylate

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]

Hydroxyethyl acrylate

Names
IUPAC name 2-hydroxyethyl prop-2-enoate
Other names HEA
Identifiers
CAS Number	818-61-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1330518
ChemSpider	12612
ECHA InfoCard	100.011.322
EC Number	212-454-9
PubChem CID	13165
RTECS number	AT1750000
UNII	25GT92NY0C
UN number	2927 1760
CompTox Dashboard (EPA)	DTXSID20891159 DTXSID2022123, DTXSID20891159
InChI InChI=1S/C5H8O3/c1-2-5(7)8-4-3-6/h2,6H,1,3-4H2 Key: OMIGHNLMNHATMP-UHFFFAOYSA-N
SMILES C=CC(=O)OCCO
Properties
Chemical formula	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]
Pictograms
Signal word	Danger
Hazard statements	H311, H314, H317, H400
Precautionary statements	P260, P261, 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). Infobox references

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]

Toxicity

The toxicity of the material has been studied and is fairly well understood.^[12][13][14]

See also

• (Hydroxyethyl)methacrylate
• Synthetic resin