Hydroxyethyl acrylate

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:
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

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]

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]

References

^ "2-Hydroxyethyl acrylate". pubchem.ncbi.nlm.nih.gov.
^ Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer, Timothy D.; Nandi, Partha (2020). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4. ISBN 9783527303854.
^ Neugebauer, Dorota (2017). "Modifications of Hydroxyl-Functionalized HEA/HEMA and Their Polymers in the Synthesis of Functional and Graft Copolymers". Current Organic Synthesis. 14 (6): 798–809. doi:10.2174/1570179414666161115163449.
^ Huo, Fanglin; Lu, Yangcheng (2022-10-15). "Green and high-efficiency synthesis of 2-hydroxyethyl acrylate with ion exchange resins as Cr(III) support and collector". Chemical Engineering Journal. 446: 137130. Bibcode:2022ChEnJ.44637130H. doi:10.1016/j.cej.2022.137130. ISSN 1385-8947. S2CID 249140875.
^ "2-HYDROXY ETHYL ACRYLATE (HEA) |". atamankimya.com. Retrieved 2023-02-19.
^ Kakwere, Hamilton; Perrier, Sébastien (2011). "Design of complex polymeric architectures and nanostructured materials/Hybrids by living radical polymerization of hydroxylated monomers". Polym. Chem. 2 (2): 270–288. doi:10.1039/c0py00160k.
^ Schier, Jan E. S.; Hutchinson, Robin A. (2016). "The influence of hydrogen bonding on radical chain-growth parameters for butyl methacrylate/2-hydroxyethyl acrylate solution copolymerization". Polymer Chemistry. 7 (27): 4567–4574. doi:10.1039/C6PY00834H. hdl:1974/26579. ISSN 1759-9954.
^ Steinhauer, Wiktor; Hoogenboom, Richard; Keul, Helmut; Moeller, Martin (2013-02-26). "Block and Gradient Copolymers of 2-Hydroxyethyl Acrylate and 2-Methoxyethyl Acrylate via RAFT: Polymerization Kinetics, Thermoresponsive Properties, and Micellization". Macromolecules. 46 (4): 1447–1460. Bibcode:2013MaMol..46.1447S. doi:10.1021/ma302606x. ISSN 0024-9297.
^ Steinhauer, Wiktor; Hoogenboom, Richard; Keul, Helmut; Moeller, Martin (2010-09-14). "Copolymerization of 2-Hydroxyethyl Acrylate and 2-Methoxyethyl Acrylate via RAFT: Kinetics and Thermoresponsive Properties". Macromolecules. 43 (17): 7041–7047. Bibcode:2010MaMol..43.7041S. doi:10.1021/ma101122b. ISSN 0024-9297.
^ Chueangchayaphan, Wannarat; Tanrattanakul, Varaporn; Chueangchayaphan, Narong; Muangsap, Suchanya; Borapak, Warisara (2017-06-21). "Synthesis and thermal properties of natural rubber grafted with poly(2-hydroxyethyl acrylate)". Journal of Polymer Research. 24 (7): 107. doi:10.1007/s10965-017-1269-5. ISSN 1572-8935. S2CID 103796137.
^ Iseki, Masashi; Suzuki, Yasuhito; Tachi, Hideki; Matsumoto, Akikazu (2018-11-30). "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". ACS Omega. 3 (11): 16357–16368. doi:10.1021/acsomega.8b02371. ISSN 2470-1343. PMC 6643581. PMID 31458271.
^ Tokumura, Fumio; Matsui, Tetsuya; Suzuki, Yasuko; Sado, Masashi; Taniguchi, Masaharu; Kobayashi, Ichiro; Kamiyama, Masashi; Suda, Shin; Nakamura, Atsushi; Yamazaki, Yuhiro; Yamori, Akira; Igarashi, Ryosuke; Kawai, Jun; Oka, Keiji (2010-01-01). "The potential dermal irritating effect of residual (meth)acrylic monomers in pressure sensitive adhesive tapes". Drug and Chemical Toxicology. 33 (1): 1–7. doi:10.3109/01480540903311043. ISSN 0148-0545. PMID 20001660. S2CID 9253289.
^ "CompTox Chemicals Dashboard". comptox.epa.gov. Retrieved 2023-02-17.
^ Moser, Virginia C.; Anthony, Douglas C.; Sette, William F.; MacPhail, Robert C. (1992). "Comparison of Subchronic Neurotoxicity of 2-Hydroxyethyl Acrylate and Acrylamide in Rats". Toxicological Sciences. 18 (3): 343–352. doi:10.1093/toxsci/18.3.343. PMID 1597260. Retrieved 2023-02-17.

[1] "2-Hydroxyethyl acrylate". pubchem.ncbi.nlm.nih.gov.

[2] Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer, Timothy D.; Nandi, Partha (2020). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4. ISBN 9783527303854.

[3] Neugebauer, Dorota (2017). "Modifications of Hydroxyl-Functionalized HEA/HEMA and Their Polymers in the Synthesis of Functional and Graft Copolymers". Current Organic Synthesis. 14 (6): 798–809. doi:10.2174/1570179414666161115163449.

[4] Huo, Fanglin; Lu, Yangcheng (2022-10-15). "Green and high-efficiency synthesis of 2-hydroxyethyl acrylate with ion exchange resins as Cr(III) support and collector". Chemical Engineering Journal. 446: 137130. Bibcode:2022ChEnJ.44637130H. doi:10.1016/j.cej.2022.137130. ISSN 1385-8947. S2CID 249140875.

[5] "2-HYDROXY ETHYL ACRYLATE (HEA) |". atamankimya.com. Retrieved 2023-02-19.

[6] Kakwere, Hamilton; Perrier, Sébastien (2011). "Design of complex polymeric architectures and nanostructured materials/Hybrids by living radical polymerization of hydroxylated monomers". Polym. Chem. 2 (2): 270–288. doi:10.1039/c0py00160k.

[7] Schier, Jan E. S.; Hutchinson, Robin A. (2016). "The influence of hydrogen bonding on radical chain-growth parameters for butyl methacrylate/2-hydroxyethyl acrylate solution copolymerization". Polymer Chemistry. 7 (27): 4567–4574. doi:10.1039/C6PY00834H. hdl:1974/26579. ISSN 1759-9954.

[8] Steinhauer, Wiktor; Hoogenboom, Richard; Keul, Helmut; Moeller, Martin (2013-02-26). "Block and Gradient Copolymers of 2-Hydroxyethyl Acrylate and 2-Methoxyethyl Acrylate via RAFT: Polymerization Kinetics, Thermoresponsive Properties, and Micellization". Macromolecules. 46 (4): 1447–1460. Bibcode:2013MaMol..46.1447S. doi:10.1021/ma302606x. ISSN 0024-9297.

[9] Steinhauer, Wiktor; Hoogenboom, Richard; Keul, Helmut; Moeller, Martin (2010-09-14). "Copolymerization of 2-Hydroxyethyl Acrylate and 2-Methoxyethyl Acrylate via RAFT: Kinetics and Thermoresponsive Properties". Macromolecules. 43 (17): 7041–7047. Bibcode:2010MaMol..43.7041S. doi:10.1021/ma101122b. ISSN 0024-9297.

[10] Chueangchayaphan, Wannarat; Tanrattanakul, Varaporn; Chueangchayaphan, Narong; Muangsap, Suchanya; Borapak, Warisara (2017-06-21). "Synthesis and thermal properties of natural rubber grafted with poly(2-hydroxyethyl acrylate)". Journal of Polymer Research. 24 (7): 107. doi:10.1007/s10965-017-1269-5. ISSN 1572-8935. S2CID 103796137.

[11] Iseki, Masashi; Suzuki, Yasuhito; Tachi, Hideki; Matsumoto, Akikazu (2018-11-30). "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". ACS Omega. 3 (11): 16357–16368. doi:10.1021/acsomega.8b02371. ISSN 2470-1343. PMC 6643581. PMID 31458271.

[12] Tokumura, Fumio; Matsui, Tetsuya; Suzuki, Yasuko; Sado, Masashi; Taniguchi, Masaharu; Kobayashi, Ichiro; Kamiyama, Masashi; Suda, Shin; Nakamura, Atsushi; Yamazaki, Yuhiro; Yamori, Akira; Igarashi, Ryosuke; Kawai, Jun; Oka, Keiji (2010-01-01). "The potential dermal irritating effect of residual (meth)acrylic monomers in pressure sensitive adhesive tapes". Drug and Chemical Toxicology. 33 (1): 1–7. doi:10.3109/01480540903311043. ISSN 0148-0545. PMID 20001660. S2CID 9253289.

[13] "CompTox Chemicals Dashboard". comptox.epa.gov. Retrieved 2023-02-17.

[14] Moser, Virginia C.; Anthony, Douglas C.; Sette, William F.; MacPhail, Robert C. (1992). "Comparison of Subchronic Neurotoxicity of 2-Hydroxyethyl Acrylate and Acrylamide in Rats". Toxicological Sciences. 18 (3): 343–352. doi:10.1093/toxsci/18.3.343. PMID 1597260. Retrieved 2023-02-17.

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