Ethyl ethanoate

Ethyl ethanoate. Also called ethyl acetate, it is an ester of the formula CH ₃ -COO-CH ₂ -CH ₃ , formerly known as vinegar ether , in German Essig-Äther, where the term “esther” or ester comes from.

Summary

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• 1 Physical properties
• 2 Chemical properties
• 3 Obtaining
• 4 Uses
  • 1 Chemical industry
  • 2 In the laboratory
  • 3 Presence in wine
• 5 Risks
  • 1 Security
• 6 External links
• 7 Sources

Physical properties

• State of aggregation Colorless liquid, with a characteristic odor. It is a colorless, fruit-smelling liquid, less dense than water and slightly miscible with it. Its vapors are denser than air.
• Density 900 kg / m3; 0.9 g / cm3
• Molar mass 88.11 g / mol
• Melting point 189 K (-83 ° C)
• Boiling point 350 K (77 ° C)
• Viscosity 0.45 cP at 20 ° C
• Refractive index 1.3724 at 20 ° C
• It is miscible with hydrocarbons, ketones, alcohols and ethers and poorly soluble in water. It is used in art as a universal solvent.

Chemical properties

• Stability: Ethyl acetate is stable at room temperature in closed containers and under normal handling and storage conditions. Heat contributes to instability. * In the presence of water you can slowly hydrolyze Ethanoland Acetic Acid .
• Polymerization: No polymerization occurs.
• Chemical incompatibility: Ethyl acetate will react vigorously with chlorosulfonic acid, oleum, potassium t-butoxide, lithium aluminum hydride, and 2-chloromethyl furan.
• Contact with nitrates, acids, alkalis, or strong oxidants can cause fire or explosion.
• Decomposition Products: The oxidative thermal decomposition of ethyl acetate can produce carbon monoxide and dioxidevapors .

Obtaining

The main way to synthesize ethyl acetate is by Fischer esterification, direct esterification by acetic acid and ethanol in the presence of a catalyst.

CH ₃ CH ₂ OH + CH ₃ COOH ⇌ CH ₃ COOCH ₂ CH ₃ + H ₂ O

Another method of preparing esters is to use not the acid itself, but its chloride, ethyl ethanoate can be obtained by the action of alcohol on the chloride of ethanoic acid. Another method of obtaining, although not economically viable, consists in reacting the silver salts of the acids with alkyl halide, ethyl ethanoate can be prepared in the presence of silver ethanoate and ethyl iodide. It is insoluble in water and dissolves easily in organic solvents. Reacts with water to form acetic acid and ethanol, a reaction that is catalyzed by the presence of acids.

Applications

Ethyl acetate is commonly used in natural fruit essences, as a nitrocellulose solvent, varnishes and lacquers, in the manufacture of artificial leather, photographic films and plates, artificial silk, perfumes and fabric cleaners, among others.

For the use of this product a well ventilated place is necessary, using a gown, safety glasses and, if necessary, natural rubber or neoprene gloves (do not use PVC), to avoid prolonged contact with the skin.

It should be stored away from sources of ignition and direct sunlight, in a well ventilated area. Large quantities of this product should be stored in grounded metal tanks.

It is a promising solvent for the commercial synthesis of vitamin E. In addition, ethyl acetate has a very good solvation capacity with respect to the reagent and allows to reduce the process temperature to 80 ° C, which would certainly increase the quality of the product ( Vitamin E). However, there are some problems related to the regeneration of ethyl acetate, compared to the previous solvents used in this process (butyl acetate), since it is more soluble in water, more volatile, and is more subject to hydrolysis under Synthetic conditions

Chemical industry

• Production of printing inks for the graphic industry.
• Production of paint thinners and solvents in the paint industry.
• In the industry of adhesives and glues derived from cellulose.
• In the food industry, in confectionery, beverages, sweets.
• In artificial fruit essences.
• Removal of resinous substances in the rubber industry.
• In the manufacture of artificial leathers and to cover and decorate leather articles.
• Solvent of compounds used to coat and decorate ceramic objects.
• Solvent for the production of various explosive compounds.
• In the photographic industry, as a solvent for the manufacture of cellulose-based films.
• Ingredient of cosmetic preparations (perfumes, enamels, hair tonics) and pharmaceutical.
• In the paper industry, for the preparation of finished paper and for coating and decorating paper objects.
• In the textile industry, for the preparation of wool fabrics for dyeing, in cleaning processes and for the preparation of finished textiles.
• Reagent for the manufacture of pigments.
• Direct use in food and drug processing is not recommended.

At the laboratory

In the laboratory, ethyl acetate is commonly used in mixtures for liquid chromatography and extraction. It is rarely selected as a reaction solvent because it is prone to hydrolysis and transesterification. Ethyl acetate is very volatile and has a low boiling point. Due to these properties, it can be recovered from a sample by heating it in a water bath and ventilating with compressed air.

Presence in wine

Ethyl acetate is one of the components of wine, it is part of the solvent series, also known as ethereal, along with lower weight alcohols and some heavier esters. It occurs mainly in an oxidative type aging, and therefore is found in a greater proportion in fragrant wines.

Risks

Highly flammable. Ingestion Abdominal pain, vertigo, nausea, sore throat, weakness. Inhalation Cough, vertigo, drowsiness, headache, nausea, gasping, sore throat, loss of consciousness, weakness. Skin Redness, pain. LD50 11.3 g / kg, rat

Security

Flammable product, do not store or mix with strong oxidants, such as liquid chlorine and concentrated oxygen. Do not handle or store near open flames, heat, sparks, requires adequate ventilation. It is irritating to the skin and respiratory tract. For more information consult the international chemical safety sheet.