Hydroxyethyl acrylate

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Hydroxyethyl acrylate
Names
IUPAC name
2-hydroxyethyl prop-2-enoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.322 Edit this at Wikidata
EC Number
  • 212-454-9
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
Appearance clear liquid
Density 1.011
Boiling point 220 °C (428 °F; 493 K)
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
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 an organic chemical and an aliphatic compound. It has the formula C5H8O3 and the CAS Registry Number 818–61–1. It is REACH registered with an EU number of 212–454–9.[2] It has dual functionality containing a polymerizable acrylic group and a terminal hydroxy group. It is used to make emulsion polymers along with other monomers and the resultant resins are used in coatings, sealants, adhesives and elastomers and other applications.[3]

Synthesis[edit]

There are a number of patents and synthesis papers to produce the material mostly aimed at reducing or removing heavy metals as catalysts. The traditional manufacturing process calls for the reaction of ethylene oxide with acrylic acid in the presence of a metal catalyst.[4]

Properties[edit]

The material is a clear water-white liquid with a mild but pungent ester like odor.[5] It has a low freezing point.

Applications[edit]

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][10] Modification of rubbers and similar compounds is also a use for the material.[11] The resultant polymers may be used to manufacture pressure-sensitive adhesives.[12]

Toxicity[edit]

The toxicity of the material has been studied and is fairly well understood.[13][14][15]

See also[edit]

References[edit]

  1. ^ "2-Hydroxyethyl acrylate". pubchem.ncbi.nlm.nih.gov.
  2. ^ PubChem. "2-Hydroxyethyl acrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-02-17.
  3. ^ Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer (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 978-3527306732.
  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. 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. ^ Monleón Pradas, M.; Gómez Ribelles, J. L.; Serrano Aroca, A.; Gallego Ferrer, G.; Suay Antón, J.; Pissis, P. (2001-05-01). "Porous poly(2-hydroxyethyl acrylate) hydrogels". Polymer. 42 (10): 4667–4674. doi:10.1016/S0032-3861(00)00742-4. ISSN 0032-3861.
  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. ^ Vargün, Elif; Usanmaz, Ali (2005-09-01). "Polymerization of 2-hydroxyethyl acrylate in bulk and solution by chemical initiator and by ATRP method". Journal of Polymer Science Part A: Polymer Chemistry. 43 (17): 3957–3965. Bibcode:2005JPoSA..43.3957V. doi:10.1002/pola.20867. ISSN 0887-624X.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ "CompTox Chemicals Dashboard". comptox.epa.gov. Retrieved 2023-02-17.
  15. ^ 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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