Chemistry:Hydroxyethyl acrylate

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Short description: Organic chemical-monomer
Hydroxyethyl acrylate
2-Hydroxyethyl acrylate.svg
Names
IUPAC name
2-hydroxyethyl prop-2-enoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 212-454-9
RTECS number
  • AT1750000
UNII
UN number 2927 1760
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 pictograms GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
GHS Signal word Danger
H311, H314, H317, H400
P260, P261, P264, P272, P273, P280, P301+330+331, P302+352, P302+361+354Script error: No such module "Preview warning".Category:GHS errors, P304+340, P305+354+338Script error: No such module "Preview warning".Category:GHS errors, P316Script error: No such module "Preview warning".Category:GHS errors, P321, P333+313, P361+364Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, 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
Tracking categories (test):

Hydroxyethyl acrylate is an organic chemical and a 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

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

The material is a clear 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][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

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

See also

References

  1. ↑ "2-Hydroxyethyl acrylate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/13165#section=Safety-and-Hazards. 
  2. ↑ PubChem. "2-Hydroxyethyl acrylate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/13165. 
  3. ↑ Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut et al. (2020). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4. 
  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" (in en). Chemical Engineering Journal 446: 137130. doi:10.1016/j.cej.2022.137130. ISSN 1385-8947. https://www.sciencedirect.com/science/article/pii/S1385894722026213. 
  5. ↑ "2-HYDROXY ETHYL ACRYLATE (HEA) |". https://atamankimya.com/sayfalaralfabe.asp?LanguageID=2&cid=3&id=2867&id2=5362. 
  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" (in en). Polymer 42 (10): 4667–4674. doi:10.1016/S0032-3861(00)00742-4. ISSN 0032-3861. https://www.sciencedirect.com/science/article/pii/S0032386100007424. 
  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" (in en). Polymer Chemistry 7 (27): 4567–4574. doi:10.1039/C6PY00834H. ISSN 1759-9954. http://xlink.rsc.org/?DOI=C6PY00834H. 
  8. ↑ Vargün, Elif; Usanmaz, Ali (2005-09-01). "Polymerization of 2-hydroxyethyl acrylate in bulk and solution by chemical initiator and by ATRP method" (in en). Journal of Polymer Science Part A: Polymer Chemistry 43 (17): 3957–3965. doi:10.1002/pola.20867. ISSN 0887-624X. Bibcode: 2005JPoSA..43.3957V. https://onlinelibrary.wiley.com/doi/10.1002/pola.20867. 
  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" (in en). Macromolecules 46 (4): 1447–1460. doi:10.1021/ma302606x. ISSN 0024-9297. Bibcode: 2013MaMol..46.1447S. https://pubs.acs.org/doi/10.1021/ma302606x. 
  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" (in en). Macromolecules 43 (17): 7041–7047. doi:10.1021/ma101122b. ISSN 0024-9297. Bibcode: 2010MaMol..43.7041S. https://pubs.acs.org/doi/10.1021/ma101122b. 
  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)" (in en). Journal of Polymer Research 24 (7): 107. doi:10.1007/s10965-017-1269-5. ISSN 1572-8935. https://doi.org/10.1007/s10965-017-1269-5. 
  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" (in en). ACS Omega 3 (11): 16357–16368. doi:10.1021/acsomega.8b02371. ISSN 2470-1343. PMID 31458271. 
  13. ↑ Tokumura, Fumio; Matsui, Tetsuya; Suzuki, Yasuko; Sado, Masashi; Taniguchi, Masaharu; Kobayashi, Ichiro; Kamiyama, Masashi; Suda, Shin et al. (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. https://doi.org/10.3109/01480540903311043. 
  14. ↑ "CompTox Chemicals Dashboard". https://comptox.epa.gov/dashboard/chemical/details/DTXSID2022123. 
  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. https://academic.oup.com/toxsci/article-lookup/doi/10.1093/toxsci/18.3.343. Retrieved 2023-02-17. 



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