2-Ethylhexyl acrylate is a colorless liquid

acrylate Acrylates (IUPAC: prop-2-enoates) are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion C H2=CHC OO−. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acry ...

with a pleasant odor.

Preparation

Racemic In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...

2-ethylhexyl acrylate can be prepared with a high yield by

esterification 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 ar ...

acrylic acid Acrylic acid (IUPAC: propenoic 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 a ...

with racemic

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

in the presence of hydroquinone as a polymerization inhibitor and a

strong acid Acid strength is the tendency of an acid, symbolised by the chemical formula HA, to dissociate into a proton, H+, and an anion, A-. The dissociation of a strong acid in solution is effectively complete, except in its most concentrated solutions. ...

such as

methanesulfonic acid Methanesulfonic acid (MsOH) or methanesulphonic acid (in British English) is an organosulfuric, colorless liquid with the chemical formula and structure . It is the simplest of the alkylsulfonic acids (). Salts and esters of methanesulfonic aci ...

reactive distillation Reactive may refer to: *Generally, capable of having a reaction (disambiguation) *An adjective abbreviation denoting a bowling ball coverstock made of reactive resin *Reactivity (chemistry) *Reactive mind *Reactive programming See also *Reactanc ...

using

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...

as an azeotroping agent.

Properties

2-Ethylhexyl acrylate

polymerizes In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many for ...

easily. The polymerization can be initiated by light,

peroxides In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable. The most common peroxide is hydrogen p ...

, heat, or contaminants. It can react violently when combined with strong oxidants and can form explosive mixtures with air at temperatures above . The chemical, physical, and toxicological properties, however, can be greatly modified by additives or stabilizers.

Use

2-Ethylhexyl acrylate and

butyl acrylate Butyl acrylate is an organic compound with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to polybutylacrylate, which is used in paints, sealants, coa ...

are the major base monomers for the preparation of acrylate adhesives. 2-Ethylhexyl acrylate can react by free-radical polymerization to form macromolecules having a molecular weight of up to 200,000 g/mol. Other monomers such as

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 v ...

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 ...

, and

styrene Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...

may be copolymerized to modify the properties of the resulting polymer.Bodo Müller, Walter Rath, Walter Rath: ''Formulierung von Kleb- und Dichtstoffen.'' 1. Auflage. Vincentz Network, Hannover 2004, , S. 235 ()

References

{{DEFAULTSORT:Ethylhexyl acrylate, 2- Acrylate esters