Hydroxyethyl acrylate

Organic chemical-monomer

Hydroxyethyl acrylate

Names
IUPAC name

2-hydroxyethyl prop-2-enoate

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)

* DTXSID2022123

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  | clear liquid
Density | 1.011
Boiling point | 220 °C (428 °F; 493 K)
Hazards
GHS labelling:[1]

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

Chemical compound

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]

* (Hydroxyethyl)methacrylate
* Synthetic resin

## 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.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H311]: H311: Toxic in contact with skin
*[H314]: H314: Causes severe skin burns and eye damage
*[H317]: H317: May cause an allergic skin reaction
*[H400]: H400: Very toxic to aquatic life
*[P260]: P260: Do not breathe dust/fume/gas/mist/vapours/spray.
*[P261]: P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
*[P264]: P264: Wash ... thoroughly after handling.
*[P272]: P272: Contaminated work clothing should not be allowed out of the workplace.
*[P273]: P273: Avoid release to the environment.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P301+P330+P331]: P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P302+P361+P354]: P302+P361+P354: IF ON SKIN: Take off Immediately all contaminated clothing. Immediately rinse with water for several minutes.
*[P304+P340]: P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
*[P305+P354+P338]: P305+P354+P338: IF IN EYES: Immediately rinse with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[P316]: P316: Get immediate emergency medical help.
*[P321]: P321: Specific treatment (see ... on this label).
*[P333+P313]: P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.
*[P361+P364]: P361+P364: Take off immediately all contaminated clothing and wash it before reuse.
*[P362+P364]: P362+P364: Take off contaminated clothing and wash it before reuse.
*[P363]: P363: Wash contaminated clothing before reuse.
*[P391]: P391: Collect spillage.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...