Acrylates (

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

: prop-2-enoates) are the

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s, and

conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid gives a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as it loses a hydrogen ion in the reve ...

s of

acrylic acid Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has ...

. The acrylate ion is the anion . Often, acrylate refers to

s of acrylic acid, the most common member being

methyl acrylate Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is a ...

. These acrylates contain

vinyl group In organic chemistry, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a functional group with the formula . It is the ethylene (IUPAC name: ethene) molecule () with one fewer hydrogen atom. The name is also used for any compound contai ...

s. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.

Monomers

Acrylates are defined by the formula , where R can be many groups: *

Acrylic acid Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has ...

Methyl acrylate Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is a ...

Ethyl acrylate Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is ...

* 2-Chloroethyl vinyl ether * 2-Ethylhexyl acrylate *

Butyl acrylate Butyl acrylate is an organic compound with the formula . A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to poly(butyl acrylate). Especially as copolymers, such materials are u ...

* Trimethylolpropane triacrylate (TMPTA) The versatility of the resulting polymers is owed to the range of R groups. File:Acrylate-anion.svg, The acrylate anion File:Trimethylolpropane triacrylate.svg, Trimethylolpropane triacrylate (TMPTA), a trifunctional acrylate ester File:Methylacrylat.svg,

, an acrylic ester File:Hexandioldiacrylat.svg, Hexandiol diacrylate, a bifunctional acrylate File: Pentaerythritol tetraacrylate.png, Pentaerythritol tetraacrylate (PETA), a tetrafunctional acrylate File:Polyacrylate.svg, A generic polyacrylate

Acrylate derivatives

Methacrylate Methacrylates are derivatives of methacrylic acid. These derivatives are mainly used to make poly(methyl methacrylate) and related polymers. *Monomers ** Methyl methacrylate ** Ethyl methacrylate ** Butyl methacrylate ** Hydroxyethyl methacrylate ...

s ( ) and

cyanoacrylate Cyanoacrylates are a family of strong fast-acting adhesives with industrial, medical, and household uses. They are derived from ethyl cyanoacrylate and related esters. The cyanoacrylate group in the monomer rapidly polymerizes in the presence ...

s ( ,) 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. File:Methyl-methacrylate-skeletal.svg,

Methyl methacrylate Methyl methacrylate (MMA) is an organic compound with the formula . This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA). History MMA ...

, precursor to "perspex" (plexiglass) File:Ethyl cyanoacrylate.svg,

Ethyl cyanoacrylate Ethyl cyanoacrylate (ECA), a cyanoacrylate ester, is an ethyl ester of 2-cyano-acrylic acid. It is a colorless liquid with low viscosity and a faint sweet smell in pure form. It is the main component of cyanoacrylate glues and can be encountered ...

, precursor to "super glue"

Polymers

Some acrylate polymers (

poly(methyl methacrylate) Poly(methyl methacrylate) (PMMA) is a synthetic polymer derived from methyl methacrylate. It is a transparent thermoplastic, used as an engineering plastic. PMMA is also known as acrylic, acrylic glass, as well as by the trade names and bran ...

etc. not included): *

Poly(methyl acrylate) Poly(methyl acrylate) (PMA) is a family of organic polymers with the formula ()n. It is a synthetic acrylate polymer derived from methyl acrylate monomer. The polymers are colorless. This homopolymer is far less important than copolymers derived ...

(PMA) *

Poly(ethyl acrylate) Poly(ethyl acrylate) (PEA) is a family of organic polymers with the formula ()n. It is a synthetic acrylate polymer derived from ethyl acrylate monomer. The polymers are colorless. This homopolymer is far less important than copolymers derived fr ...

(PEA) *

Poly(butyl acrylate) Poly(butyl acrylate) (PBA) is a family of organic polymers with the formula ()n. It is a synthetic acrylate polymer derived from butyl acrylate monomer. The polymers are colorless. This homopolymer is far less important than copolymers derived fr ...

(PBA) Acrylate

monomer A monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or two- or three-dimensional network in a process called polymerization. Classification Chemis ...

s are used to form acrylate polymers. Most commonly, these polymers are in fact copolymers, being derived from two monomers.

Related polymers

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 Methyl methacrylate (MMA) is an organic compound with the formula . This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA). History MMA ...

and many related esters, especially

polymethyl methacrylate Poly(methyl methacrylate) (PMMA) is a synthetic polymer derived from methyl methacrylate. It is a transparent thermoplastic, used as an engineering plastic. PMMA is also known as acrylic, acrylic glass, as well as by the trade names and brands ...

. A second large family of acrylate-like polymers are derived from

ethyl cyanoacrylate Ethyl cyanoacrylate (ECA), a cyanoacrylate ester, is an ethyl ester of 2-cyano-acrylic acid. It is a colorless liquid with low viscosity and a faint sweet smell in pure form. It is the main component of cyanoacrylate glues and can be encountered ...

, which gives rise to

s. Yet another family of acrylate-related polymers are the

polyacrylamide Polyacrylamide (abbreviated as PAM or pAAM) is a polymer with the formula (-CH2CHCONH2-). It has a linear-chain structure. PAM is highly water-absorbent, forming a soft gel when hydrated. In 2008, an estimated 750,000,000 kg were produced, ...

s, especially the parent derived from

acrylamide Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary ...

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 Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the r ...

Production

Acrylates are industrially prepared by treating acrylic acid with the corresponding alcohol in presence of a catalyst. The reaction with lower alcohols (

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

) takes place at 100–120 °C with acidic

heterogeneous catalysts Heterogeneous catalysis is catalysis where the phase of catalysts differs from that of the reagents or products. The process contrasts with homogeneous catalysis where the reagents, products and catalyst exist in the same phase. Phase distingui ...

(

cation exchanger An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

). The reaction of higher alcohols ( ''n''-butanol,

2-ethylhexanol 2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula . It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a l ...

) is catalysed with

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

in homogeneous phase. Acrylates of even higher alcohols are obtainable by

of lower esters catalysed by titanium alcoholates or organic tin compounds (e.g. dibutyltin dilaurate).

References

{{Authority control Carboxylate anions Monomers Acrylate esters