Hydroxyethyl acrylate

Organic chemical-monomer

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:[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 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

[edit]

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

[edit]

The material is a 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] 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

[edit]

The toxicity of the material has been studied and is fairly well understood.[12][13][14]

## See also

[edit]

* (Hydroxyethyl)methacrylate
* Synthetic resin

## References

[edit]

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.

*[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 ...