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)
ECHA InfoCard 100.002.801
Properties
C11H20O2
Molar mass 184.28 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Ethylhexyl acrylate chemical compound which belongs to the acrylates. It is a colorless liquid with a sweet odour.

Preparation

The 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 azeotroping agent.[1]

Properties

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

Use

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

References

  1. ↑ US 2917538, R.L. Carlyle, "Process for the production of acrylic acid esters", published 1959-12-15, assigned to The Dow Chemical Co.
  2. ↑ Bodo Müller, Walter Rath, Walter Rath: Formulierung von Kleb- und Dichtstoffen. 1. Auflage. Vincentz Network, Hannover 2004, ISBN 3878707916, S. 235 (, p. 235, at Google Books).
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