Acrylate

Short description: Salt or ester of acrylic acid

Acrylates (IUPAC: prop-2-enoates) are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH
2=CHCO−
2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.[1]

## Contents

* 1 Monomers
* 1.1 Acrylate derivatives
* 2 Polymers
* 2.1 Related polymers
* 3 Other uses
* 4 Production
* 5 See also
* 6 References

## Monomers

Acrylates are defined by the formula CH
2=CHCO
2R, where R can be many groups:

* Acrylic acid
* Methyl acrylate
* Ethyl acrylate
* 2-Chloroethyl vinyl ether
* 2-Ethylhexyl acrylate
* Butyl acrylate
* Trimethylolpropane triacrylate (TMPTA)

The versatility of the resulting polymers is owed to the range of R groups.

* Structures of some acrylates
* The acrylate anion

* Trimethylolpropane triacrylate (TMPTA), a trifunctional acrylate ester

* Methyl acrylate, an acrylic ester

* Hexandiol diacrylate, a bifunctional acrylate

* Pentaerythritol tetraacrylate (PETA), a tetrafunctional acrylate

* A generic polyacrylate

### Acrylate derivatives

Methacrylates ( CH
2=C(CH
3)CO
2R) and cyanoacrylates ( CH
2=C(CN)CO
2R,) are closely related to acrylates. The feature a methyl and a nitrile in place of the H alpha to the carboxy functional group. They share several properties, being polymerized by radicals and being colorless.[2]

* Structures of some important modified acrylates
* Methyl methacrylate, precursor to "perspex" (plexiglass)

* Ethyl cyanoacrylate, precursor to "super glue"

## Polymers

Structure of a generic polyacrylate. Polyacrylates are derived from acrylates but do not contain acrylate groups.

Main article: Physics:Acrylate polymer

Some acrylate polymers (poly(methyl methacrylate) etc. not included):

* Poly(methyl acrylate) (PMA)
* Poly(ethyl acrylate) (PME)
* Poly(butyl acrylate)

Acrylate monomers are used to form acrylate polymers. Most commonly, these polymers are in fact copolymers, being derived from two monomers.[3][4]

### Related polymers

Structure of the backbone of a cyanoacrylate polymer.

In the same way that several variants of acrylic esters are known, so too are the corresponding polymers. Their properties strongly depends on the substituent.

A large family of acrylate-like polymers are derived from methyl methacrylate and many related esters, especially polymethyl methacrylate.

A second large family of acrylate-like polymers are derived from ethyl cyanoacrylate, which gives rise to cyanoacrylates.

Yet another family of acrylate-related polymers are the polyacrylamides, especially the parent derived from acrylamide.

## Other uses

In addition to forming polymers, acrylate esters participate in other reactions relevant to organic chemistry. They are Michael acceptors and dienophiles. They undergo transesterification.

## Production

Acrylates are industrially prepared by treating acrylic acid with the corresponding alcohol in presence of a catalyst. The reaction with lower alcohols (methanol, ethanol) takes place at 100–120 °C with acidic heterogeneous catalysts (cation exchanger). The reaction of higher alcohols (n-butanol, 2-ethylhexanol) is catalysed with sulfuric acid in homogeneous phase. Acrylates of even higher alcohols are obtainable by transesterification of lower esters catalysed by titanium alcoholates or organic tin compounds (e.g. dibutyltin dilaurate).[5]

## See also

* Acrylate polymer
* Sodium polyacrylate thickeners
* Methacrylate

## References

1. ↑ Takashi Ohara; Takahisa Sato; Noboru Shimizu; Günter Prescher; Helmut Schwind; Otto Weiberg; Klaus Marten; Helmut Greim (2003). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.pub2. ISBN 3527306730.
2. ↑ Veerle Coessens; Tomislav Pintauer; Krzysztof Matyjaszewski (2001). "Functional polymers by atom transfer radical polymerization". Functional polymers by atom transfer radical polymerization. 26. 337–377. doi:10.1016/S0079-6700(01)00003-X.
3. ↑ Takashi Ohara; Takahisa Sato; Noboru Shimizu; Günter Prescher; Helmut Schwind; Otto Weiberg; Klaus Marten; Helmut Greim (2002). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.pub2. ISBN 978-3-527-30673-2. (Subscription content?)
4. ↑ "Polyacrylates". http://pslc.ws/macrog/acrylate.htm.
5. ↑ Arpe, Hans-Jürgen (2007). Industrielle organische Chemie: bedeutende Vor- und Zwischenprodukte. (6 ed.). Weinheim: Wiley-VCH. ISBN 978-3-527-31540-6.

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