2-Ethylhexyl acrylate

2-Ethylhexyl acrylate
Names
Preferred IUPAC name
2-Ethylhexyl prop-2-enoate
Other names
2-Ethylhexyl acrylate
2-EHA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.801 Edit this at Wikidata
EC Number
  • 203-080-7
KEGG
UNII
  • InChI=1S/C11H20O2/c1-4-7-8-10(5-2)9-13-11(12)6-3/h6,10H,3-5,7-9H2,1-2H3
    Key: GOXQRTZXKQZDDN-UHFFFAOYSA-N
  • CCCCC(CC)COC(=O)C=C
Properties
C11H20O2
Molar mass 184.279 g·mol−1
Appearance colorless liquid
Density 0.885 g/mL
Melting point −90 °C (−130 °F; 183 K)
Boiling point 215–219 °C (419–426 °F; 488–492 K)
organic solvents
Hazards
GHS labelling:
GHS07: Exclamation mark[1]
Warning
H315, H317, H335, H412[1]
P273, P280, P304+P340+P312, P333+P313[1]
Flash point 82 °C; 180 °F; 355 K
258 °C; 496 °F; 531 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Ethylhexyl acrylate is a colorless liquid acrylate used in the making of paints,[2] plastics[3] and adhesives.[4] It has an odor that has been variously described as pleasant[5] or acrid and musty.[6]

Preparation

Racemic 2-ethylhexyl acrylate can be prepared with a high yield by esterification of acrylic acid with racemic 2-ethylhexanol in the presence of hydroquinone as a polymerization inhibitor and a strong acid such as methanesulfonic acid by reactive distillation using toluene as an azeotroping agent.[7]

Properties

2-Ethylhexyl acrylate polymerizes easily. The polymerization can be initiated by light, peroxides, heat, or contaminants. It can react violently when combined with strong oxidants and can form explosive mixtures with air at temperatures above 82 °C (180 °F).[2] The chemical, physical, and toxicological properties, however, can be greatly modified by additives or stabilizers.

Use

2-Ethylhexyl acrylate and butyl acrylate are the major base monomers for the preparation of acrylate adhesives. 2-Ethylhexyl acrylate can react by free-radical polymerization to form macromolecules having a molecular weight of up to 200,000 g/mol. Other monomers such as vinyl acetate, methyl acrylate, and styrene may be copolymerized to modify the properties of the resulting polymer.[8]

References

  1. ^ a b c Record of 2-Ethylhexyl acrylate in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 11 March 2020.
  2. ^ a b "2-ETHYLHEXYL ACRYLATE". CAMEO Chemicals. Retrieved April 22, 2024.
  3. ^ "2-Ethylhexyl acrylate (compound)". PubChem. National Center for Biotechnology Information.
  4. ^ Heatley, Frank; Lovell, Peter A.; Yamashita, Tsuyoshi (2001-10-01). "Chain Transfer to Polymer in Free-Radical Solution Polymerization of 2-Ethylhexyl Acrylate Studied by NMR Spectroscopy". Macromolecules. 34 (22): 7636–7641. doi:10.1021/ma0101299. ISSN 0024-9297.
  5. ^ "2-Ethylhexyl acrylate". PubChem. Retrieved April 22, 2024.
  6. ^ Shah, Yogi (January 1995). "2-Ethylhexyl acrylate" (PDF). Occupational Safety and Health Administration.
  7. ^ US 2917538, R.L. Carlyle, "Process for the production of acrylic acid esters", published 1959-12-15, assigned to The Dow Chemical Co. 
  8. ^ Bodo Müller, Walter Rath: Formulierung von Kleb- und Dichtstoffen 1. Auflage. Vincentz Network, Hannover 2004, ISBN 3878707916, S. 235 ([1], p. 235, at Google Books)