Dimethylaminoethyl acrylate (2-dimethylaminoethyl acrylate) or DMAEA is an unsaturated

carboxylic acid ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are ...

having a

tertiary amino group In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent su ...

. It is a colorless to yellowish, water-miscible liquid with a pungent, amine-like odor. DMAEA is an important acrylic

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

that gives basic properties to

copolymer In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...

Preparation

2-Dimethylaminoethyl acrylate is prepared via

transesterification In organic chemistry, transesterification is the process of exchanging the organic 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. The reaction ca ...

of acrylic acid esters such as

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 al ...

(R = -CH₃) or ethyl acrylate (R = -CH₂-CH₃) with 2-dimethylaminoethanol under acid catalysis with tin compounds (for example stannoxanes) or titanium compounds (for example

tetraisopropyl orthotitanate Titanium isopropoxide, also commonly referred to as titanium tetraisopropoxide or TTIP, is a chemical compound with the formula . This alkoxide of titanium(IV) is used in organic synthesis and materials science. It is a diamagnetic tetrahedral m ...

). More than 95% yield can be achieved. EA Transesterification

During the reaction, inhibitors must be present (such as

phenothiazine Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. ...

), because of the high tendency of starting material and product to polymerize. When ethyl acrylate is used as a reactant,

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a h ...

is formed; this forms with the ethyl acrylate an azeotrope of the composition ethanol/ethyl acrylate 72.7:26.3%, which boils at 77.5 °C under atmospheric pressure. To achieve a high reaction yield, the ethanol is distilled off from the reaction mixture. The product is purified by vacuum distillation and stabilized with about 1,000 ppm

4-methoxyphenol Mequinol, MeHQ or 4-methoxyphenol, is a phenol used in dermatology and organic chemistry. Uses Dermatology Mequinol is a common active ingredient in topical drugs used for skin depigmentation. As a topical drug mequinol is often mixed with treti ...

(MEHQ).

Properties

Dimethylaminoethyl acrylate is a clear, colorless to slightly yellowish liquid with a pungent amine-like odor. It is miscible with water, reacts bases and hydrolyzes rapidly to acrylic acid and

dimethylaminoethanol Dimethylethanolamine (DMAE or DMEA) is an organic compound with the formula (CH3)2NCH2CH2OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care produ ...

. It can form ignitable mixtures with air. DMAEA tends to spontaneously polymerize at elevated temperatures, upon irradiation, and in the presence of free-radical initiators. It must therefore be adequately stabilized, stored in a dry and cool place (<25 °C). DMAEA is very toxic because of its high inhalation toxicity.

Use

Dimethylaminoethyl acrylate is an acrylic acid ester carrying a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...

with basic properties. It therefore reacts as an α, β-unsaturated carbonyl compound in an

addition reaction In organic chemistry, an addition reaction is, in simplest terms, an organic reaction where two or more molecules combine to form a larger one (the adduct).. Addition reactions are limited to chemical compounds that have multiple bonds, such as ...

with

nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they a ...

s in a

Michael addition In organic chemistry, the Michael reaction or Michael addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbo ...

. As a reactive monomer, 2-dimethylaminoethyl acrylate forms homopolymers and copolymers with acrylic acid and acrylic acid salts, amides and esters, as well as

methacrylate Methacrylates are derivatives of methacrylic acid. * Methyl methacrylate * Ethyl methacrylate * Butyl methacrylate * Hydroxyethyl methacrylate * Glycidyl methacrylate Glycidyl methacrylate (GMA) is an ester of methacrylic acid and glycidol. C ...

s, acrylonitrile, maleic acid esters,

vinyl acetate Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate and ethene-vinyl acetate copolymers, important industrial polymers. Production The worldwide production capacity of ...

, chloroethene (vinyl chloride),

1,1-dichloroethene 1,1-Dichloroethene, commonly called 1,1-dichloroethylene or vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula CHCl. It is a colorless liquid with a sharp odor. Like most chlorocarbons, it is poorly soluble in water, ...

, styrene,

1,3-butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two viny ...

, unsaturated polyesters and

drying oil A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air, at room temperature. The oil hardens through a chemical reaction in which the components crosslink (and hence, polymerize) by the action of oxygen ( ...

s. In copolymers, DMAEA improves their nucleophilicity,

basicity In chemistry, there are three definitions in common use of the word base, known as Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. ...

, water solubility and adhesion to polar negatively charged substrates, as well as dyeability of

acrylic fiber Acrylic fibers are synthetic fibers made from a polymer ( polyacrylonitrile) with an average molecular weight of ~100,000, about 1900 monomer units. For a fiber to be called "acrylic" in the US, the polymer must contain at least 85% acrylon ...

s with anionic dyes. Such copolymers are used as resins and paints, coatings and adhesives, as well as

hair spray Hair spray (also hair lacquer or spritz) is a common cosmetic hairstyling product that is sprayed onto hair to protect against humidity and wind. Hair sprays typically consist of several components for the hair as well as a propellant. Ingr ...

. The most significant use for DMAEA is the quaternization with alkylating agents (for example

chloromethane Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula . One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industrial ...

dimethyl sulfate Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agen ...

benzyl chloride Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block. Preparation Benzyl chloride is prepared indu ...

) to the quaternary ammonium salt. DMAEA quat Synthese

The most important compound is the reaction product with methyl chloride, trimethylammonium ethyl acrylate chloride.Arkema S.A.
''2-dimethylaminoethyl acrylate''
retrieved 6 December 2016. It has the most pronounced cationic properties of all acrylates and is traded as an 80% aqueous solution. Copolymerization of trimethylammoniumethyl acrylate chloride with acrylamide leads to high molecular weight cationic

polyacrylamide Polyacrylamide (abbreviated as PAM) 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, mainly f ...

s, which are widely used as coagulants and flocculants

SNF Floerger SNF is the global leader in manufacturing polyacrylamides with a capacity of 1190 kt/y (active equivalent). These water-soluble polymers are used as flocculants and coagulants in solid/water separation to recycle water, rheology modifiers and fric ...

''Water Treatment''
/ref> in waste water purification and as retention and dewatering agents in papermaking.

References

Acrylate esters Dimethylamino compounds Esters