Acrylate

Source: Wikipedia, the free encyclopedia.

Acrylates (

bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.[1]

Monomers

Acrylates are defined by the formula CH2=CHCO2R, where R can be many groups:

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

Acrylate derivatives

Methacrylates ( CH2=C(CH3)CO2R) and cyanoacrylates ( CH2=C(CN)CO2R,) 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]

Polymers

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

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

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

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

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 (

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

References