Hydroxyethyl acrylate

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.{{Cite journal |last1=Huo |first1=Fanglin |last2=Lu |first2=Yangcheng |date=2022-10-15 |title=Green and high-efficiency synthesis of 2-hydroxyethyl acrylate with ion exchange resins as Cr(III) support and collector |url=https://www.sciencedirect.com/science/article/pii/S1385894722026213 |journal=Chemical Engineering Journal |language=en |volume=446 |pages=137130 |doi=10.1016/j.cej.2022.137130 |bibcode=2022ChEnJ.44637130H |s2cid=249140875 |issn=1385-8947|url-access=subscription }}

The material is a water-white liquid with a mild but pungent ester like odor.{{Cite web |title=2-HYDROXY ETHYL ACRYLATE (HEA) {{!}} |url=https://atamankimya.com/sayfalaralfabe.asp?LanguageID=2&cid=3&id=2867&id2=5362 |access-date=2023-02-19 |website=atamankimya.com}} It has a low freezing point.

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.{{Cite journal |doi=10.1039/c0py00160k |title=Design of complex polymeric architectures and nanostructured materials/Hybrids by living radical polymerization of hydroxylated monomers |date=2011 |last1=Kakwere |first1=Hamilton |last2=Perrier |first2=Sébastien |journal=Polym. Chem. |volume=2 |issue=2 |pages=270–288 }}{{Cite journal |last1=Schier |first1=Jan E. S. |last2=Hutchinson |first2=Robin A. |date=2016 |title=The influence of hydrogen bonding on radical chain-growth parameters for butyl methacrylate/2-hydroxyethyl acrylate solution copolymerization |url=http://xlink.rsc.org/?DOI=C6PY00834H |journal=Polymer Chemistry |language=en |volume=7 |issue=27 |pages=4567–4574 |doi=10.1039/C6PY00834H |hdl=1974/26579 |issn=1759-9954|hdl-access=free |url-access=subscription }}{{Cite journal |last1=Steinhauer |first1=Wiktor |last2=Hoogenboom |first2=Richard |last3=Keul |first3=Helmut |last4=Moeller |first4=Martin |date=2013-02-26 |title=Block and Gradient Copolymers of 2-Hydroxyethyl Acrylate and 2-Methoxyethyl Acrylate via RAFT: Polymerization Kinetics, Thermoresponsive Properties, and Micellization |url=https://pubs.acs.org/doi/10.1021/ma302606x |journal=Macromolecules |language=en |volume=46 |issue=4 |pages=1447–1460 |doi=10.1021/ma302606x |bibcode=2013MaMol..46.1447S |issn=0024-9297|url-access=subscription }}{{Cite journal |last1=Steinhauer |first1=Wiktor |last2=Hoogenboom |first2=Richard |last3=Keul |first3=Helmut |last4=Moeller |first4=Martin |date=2010-09-14 |title=Copolymerization of 2-Hydroxyethyl Acrylate and 2-Methoxyethyl Acrylate via RAFT: Kinetics and Thermoresponsive Properties |url=https://pubs.acs.org/doi/10.1021/ma101122b |journal=Macromolecules |language=en |volume=43 |issue=17 |pages=7041–7047 |doi=10.1021/ma101122b |bibcode=2010MaMol..43.7041S |issn=0024-9297|url-access=subscription }} Modification of rubbers and similar compounds is also a use for the material.{{Cite journal |last1=Chueangchayaphan |first1=Wannarat |last2=Tanrattanakul |first2=Varaporn |last3=Chueangchayaphan |first3=Narong |last4=Muangsap |first4=Suchanya |last5=Borapak |first5=Warisara |date=2017-06-21 |title=Synthesis and thermal properties of natural rubber grafted with poly(2-hydroxyethyl acrylate) |url=https://doi.org/10.1007/s10965-017-1269-5 |journal=Journal of Polymer Research |language=en |volume=24 |issue=7 |pages=107 |doi=10.1007/s10965-017-1269-5 |s2cid=103796137 |issn=1572-8935|url-access=subscription }} The resultant polymers may be used to manufacture pressure-sensitive adhesives.{{Cite journal |last1=Iseki |first1=Masashi |last2=Suzuki |first2=Yasuhito |last3=Tachi |first3=Hideki |last4=Matsumoto |first4=Akikazu |date=2018-11-30 |title=Design of a High-Performance Dismantlable Adhesion System Using Pressure-Sensitive Adhesive Copolymers of 2-Hydroxyethyl Acrylate Protected with tert -Butoxycarbonyl Group in the Presence of Cross-Linker and Lewis Acid |journal=ACS Omega |language=en |volume=3 |issue=11 |pages=16357–16368 |doi=10.1021/acsomega.8b02371 |issn=2470-1343 |pmc=6643581 |pmid=31458271}}

The toxicity of the material has been studied and is fairly well understood.{{Cite journal |last1=Tokumura |first1=Fumio |last2=Matsui |first2=Tetsuya |last3=Suzuki |first3=Yasuko |last4=Sado |first4=Masashi |last5=Taniguchi |first5=Masaharu |last6=Kobayashi |first6=Ichiro |last7=Kamiyama |first7=Masashi |last8=Suda |first8=Shin |last9=Nakamura |first9=Atsushi |last10=Yamazaki |first10=Yuhiro |last11=Yamori |first11=Akira |last12=Igarashi |first12=Ryosuke |last13=Kawai |first13=Jun |last14=Oka |first14=Keiji |date=2010-01-01 |title=The potential dermal irritating effect of residual (meth)acrylic monomers in pressure sensitive adhesive tapes |url=https://doi.org/10.3109/01480540903311043 |journal=Drug and Chemical Toxicology |volume=33 |issue=1 |pages=1–7 |doi=10.3109/01480540903311043 |issn=0148-0545 |pmid=20001660|s2cid=9253289 |url-access=subscription }}{{Cite web |title=CompTox Chemicals Dashboard |url=https://comptox.epa.gov/dashboard/chemical/details/DTXSID2022123 |access-date=2023-02-17 |website=comptox.epa.gov}}{{Cite journal |url=https://academic.oup.com/toxsci/article-lookup/doi/10.1093/toxsci/18.3.343 |title=Comparison of Subchronic Neurotoxicity of 2-Hydroxyethyl Acrylate and Acrylamide in Rats |access-date=2023-02-17 |journal=Toxicological Sciences|year=1992 |doi=10.1093/toxsci/18.3.343|last1=Moser |first1=Virginia C. |last2=Anthony |first2=Douglas C. |last3=Sette |first3=William F. |last4=MacPhail |first4=Robert C. |volume=18 |issue=3 |pages=343–352 |pmid=1597260 |url-access=subscription }}

• (Hydroxyethyl)methacrylate
• Synthetic resin

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Category:Monomers

Category:Acrylate esters

Category:Hydroxyethyl compounds