Ethyl acrylate

• Ethyl
• Propenoate
• Ethylpropenat

Colorless liquid with a pungent odor

Liquid

0.92 g · cm -3

< -75 ° C

100 ° C.

39 hPa ( 20 ° C)

Poorly in water (15 g · l-1 at 20 ° C)

1,404

Risk

5 ml · m-3 and 21 mg · m-3

400 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Acrylic acid ethyl ester, also commonly referred to, ethyl acrylate, is an organic chemical compound consisting of the group of the carboxylic acid ester ( specifically, the acrylic acid ester). It is in the form of a flammable and volatile liquid before with unpleasant pungent odor.

History

Ethyl acrylate is produced commercially since the early 1930s. Ethyl acrylate is now with an annual production of approximately 500,000 tonnes of butyl acrylate by the world's most important acrylic acid ester. Thus, in 2006 in the USA 262 kt, kt in Western Europe 63 kt in South Africa and 35 kt in South Korea and 50 in 2009, China produced 94 kt ethyl acrylate.

Production and representation

Acrylic acid ethyl ester can be prepared by several methods. It can be obtained by reaction of acrylonitrile with ethanol and sulfuric acid as a catalyst. It can also be obtained from acetylene, carbon monoxide and ethanol. According to a method of Celanese Corp.. was prepared in ethyl USA by reacting acrylic acid with ethylene and sulfuric acid via the intermediately formed acid ethyl ester and diethyl sulphate.

In a pilot plant of ADM Corp.. is → → acrolein acrylic acid Ethanol → ethyl acrylate investigated the catalytic conversion of the biomass (maize stem ) in the reaction sequence glucose → glycerol.

Today ethyl is practically with ethanol produced exclusively by direct esterification of acrylic acid (yield 93% of theory).

Properties

Ethyl acrylate is chemically unstable and has a tendency, under the influence of light, at an elevated temperature and in contact with peroxide in a stabilized form in the spontaneous (sometimes explosive ) polymerization. It has a viscosity of 0.55 mPa.s at 25 ° C and a specific heat capacity of 1.98 kJ / (kg · K). Due to the high polymerization of ethyl acrylate is commercially available stabilized with 15 ± 5 ppm MEHQ. When stored in the absence of light in the presence of a polymerization- acting oxygen and at temperatures below 35 ° C. However, a storage period is given by a year.

Use

Ethyl acrylate reacts under catalysis by Lewis bases in a Michael addition reaction with amines in high yields of β -alanine derivatives

The nucleophilic addition of ethyl acrylate as α, β -unsaturated carbonyl compound is the recurring motif in the synthesis of pharmaceutical intermediates, to (now obsolete ) drugs such as the hypnotic glutethimide or the vasodilator Vincamine or newer agents such as the COPD drug cilomilast or nootropic Leteprinim lead.

Serve with ethyl acrylate as the dienophile goes Diels -Alder reactions, for example, react with 1,3- butadiene in a [ 4 2 ] cycloaddition with high yield to a cyclohexene carboxylic acid esters.

Acrylic acid ethyl ester is the starting material for homologous acrylic acid esters ( acrylates ) by transesterification with a higher alcohol by means of acidic or basic catalysis. Thus Specialty Acrylics are available, such as that used for pressure-sensitive adhesives 2-ethylhexyl acrylate ( 2 -ethylhexanol ), the cyclohexyl used for automotive clearcoats ( from cyclohexanol ), eg the with diisocyanates crosslinked to swellable gels 2-hydroxyethyl acrylate ( in ethylene glycol ), the comonomer of comb polymers which reduce the freezing point of paraffin oils, useful long-chain acrylates ( of C18 alcohols ) as well as for the production of flocculating agents for waste water treatment and paper making important 2 - dimethylaminoethyl ( from dimethylaminoethanol ).

As the reactive monomer is ethyl acrylate used in homopolymers and copolymers with ao Ethylene, acrylic acid and its salts, amides and esters, methacrylates, acrylonitrile, maleic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, unsaturated polyesters,

Copolymers of ethyl acrylate with ethylene (English EEA ethylene -ethyl acrylate copolymer ) are suitable, such as ethylene - vinyl acetate ( EVA) - increase copolymers as adhesives and polymer additives, copolymers with acrylic acid, the cleaning effect of liquid detergents, copolymers with methacrylic acid as enteric-coated tablet coatings (Eudragit ®).

The large number of possible co-monomer units and their combination in co-and terpolymers with ethyl acrylate allows different properties of acrylate copolymers in a variety of applications ranging from paints and adhesives to paper, textile and leather auxiliaries to cosmetics and pharmaceutical products.

Ethyl acrylate is used as a flavoring agent. It was found as a volatile component in pineapple and Beaufort cheese and is a minor component in vanilla flavor, which is obtained in the hot extraction of vanilla in amounts up to about 1 ppm and negative in such high concentrations of the extract flavor beeinflusst.Angesichts his Toxikologiedatenist the targeted use of to evaluate ethyl acrylate as a flavoring in consumer critical.

Safety

The vapors of ethyl acrylate combine with air to form an explosive mixture (flash point 9 ° C, ignition temperature 350 ° C). Contact with ethyl acrylate is a risk of skin sensitization. Evidence from animal experiments to a possible carcinogenicity of ethyl acrylate are not transferable to people.The high toxicity of ethyl acrylate ( LD50 1,000 mg / kg rat oral LD50 and 1,800 mg / kg rabbit dermal ) makes the handling of the substance in enclosed compartments where. However, the pungent odor of ethyl acrylate is perceptible even at concentrations of about 1 ppb, which is well below the guideline value for acute exposure (Acute Exposure Guideline Level, AEGL -1 ) of the U.S. Environmental Protection Agency of 8.3 ppm.