Hydroxyethyl acrylate

Last updated
Hydroxyethyl acrylate
2-Hydroxyethyl acrylate.svg
Names
IUPAC name
2-hydroxyethyl prop-2-enoate
Other names
HEA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.322 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 212-454-9
PubChem CID
RTECS number
  • AT1750000
UNII
UN number 2927 1760
  • InChI=1S/C5H8O3/c1-2-5(7)8-4-3-6/h2,6H,1,3-4H2
    Key: OMIGHNLMNHATMP-UHFFFAOYSA-N
  • C=CC(=O)OCCO
Properties
C5H8O3
Molar mass 116.116 g·mol−1
Appearancecolorless liquid
Density 1.106
Boiling point 220 °C (428 °F; 493 K)
Hazards
GHS labelling: [1]
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
Danger
H311, H314, H317, H400
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).

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]

Contents

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

References

  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. Archived from the original on April 17, 2025. 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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