Ethyl acetate

Ethyl acetate


IUPAC name	Ethyl ethanoate
Other names	ethyl ester, acetic ester, ester of ethanol
Identifiers
CAS number	[141-78-6]
RTECS number	AH5425000
SMILES	CCOC(C)=O
Properties
Molecular formula	C₄H₈O₂
Molar mass	88. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 105 g/mol
Appearance	colorless liquid
Density	0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 897 g/cm³, liquid
Melting point	−83. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 6 °C (189. 55 K)
Boiling point	77. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 1 °C (350. 25 K)
Solubility in water	8. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 3 g/100 mL (20 °C)
Solubility in ethanol, acetone, diethyl ether, benzene	Miscible
Refractive index (n_D)	1. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium 3720
Viscosity	0. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 426 cP at 25 °C
Structure
Dipole moment	1. The poise (symbol P pwɑːz is the unit of dynamic Viscosity in the Centimetre gram second system of units. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 78 D
Hazards
MSDS	External MSDS
Main hazards	Flammable (F), Irritant (Xi)
NFPA 704	3 1 0
R-phrases	R11, R36, R66, R67
S-phrases	S16, S26, S33
Flash point	−4 °C
Related compounds
Related carboxylate esters	Methyl acetate, Propyl acetate, Butyl acetate
Related compounds	Acetic acid, ethanol
Supplementary data page
Structure and properties	n, ε_r, etc. The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance This page provides supplementary chemical data on Ethyl acetate. Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air A carboxylate ester is an Ester where the parent Acid is a Carboxylic acid. Methyl acetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear flammable liquid with a characteristic not unpleasant smell like certain The Chemical compound propyl acetate, also known as propyl ethanoate, is a common Solvent. n -Butyl acetate, also known as butyl ethanoate, is an Organic compound commonly used as a Solvent in the production of Lacquers Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste This page provides supplementary chemical data on Ethyl acetate. This page provides supplementary chemical data on Ethyl acetate. The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Ethyl acetate (systematically, ethyl ethanoate, commonly abbreviated EA) is the organic compound with the formula CH₃COOCH₂CH₃. This page provides supplementary chemical data on Ethyl acetate. This page provides supplementary chemical data on Ethyl acetate. Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry ( UV/ VIS) involves the Spectroscopy of Photons in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly The IUPAC nomenclature of organic chemistry is a systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. This colorless liquid has a characteristic, not unpleasant smell (similar to pear drops) like certain glues or nail polish removers, in which it is used. A pear drop is a boiled sweet made from Sugar and Flavourings. Glue or adhesive is a compound that adheres or bonds two items together Nail polish or nail varnish is a Lacquer that is applied to the nails of both the Fingers and Toes usually cosmetically but also as Ethyl acetate is the ester from ethanol and acetic acid; it is manufactured on a large scale for use as a solvent. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste

1 Properties
2 Preparation
3 Industrial production
4 Uses
5 Reactions
6 References
7 External links

Properties

Ethyl acetate is a moderately polar solvent that has the advantages of being volatile, relatively non-toxic, and non-hygroscopic. Volatility in the context of Chemistry, Physics and Thermodynamics is a measure of the tendency of a substance to Vaporize. Hygroscopy is the ability of a substance to attract Water Molecules from the surrounding environment through either absorption or Adsorption It is a weak hydrogen bond acceptor, and is not a donor due to the lack of an acidic proton (one directly bonded to an electronegative atom such as fluorine, oxygen, or nitrogen). A hydrogen bond results from a Dipole-dipole force between an Electronegative atom and a Hydrogen atom bonded to Nitrogen, Oxygen In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are " Electronegativity " is the opposite of " Electropositivity," which describes an element's ability to donate electrons Ethyl acetate can dissolve up to 3% water and has a solubility of 8% in water at room temperature. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. At elevated temperature its solubility in water is higher. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. It is unstable in the presence of strong aqueous bases and acids. In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are

Preparation

Ethyl acetate is synthesized via the Fischer esterification reaction from acetic acid and ethanol, typically in the presence of an acid catalyst such as sulfuric acid. Fischer esterification or Fischer-Speier esterification is a special type of Esterification and the process of forming an Ester by Refluxing a Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid.

CH₃CH₂OH + CH₃COOH → CH₃COOCH₂CH₃ + H₂O

It can also be prepared through Tishchenko reaction, by combining two equivalents of acetaldehyde in the precence of an alkoxide base as catalyst. Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as The Tishchenko reaction is a Chemical reaction that involves Disproportionation of an Aldehyde lacking a hydrogen atom in the alpha position in the presence Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula C[[Hydrogen H]]3CH O or MeCHO An alkoxide is the Conjugate base of an Alcohol and therefore consists of an organic group bonded to a negatively charged Oxygen atom This way is a commercial method of producing ethyl acetate.

CH₃CHO + CH₃CHO → CH₃COOC₂H₅

Industrial production

Industrially, ethyl acetate can be produced by the catalytic dehydrogenation of ethanol. Dehydrogenation is a chemical reaction that involves the elimination of Hydrogen (H2 For cost reasons, this method is primarily applied to conversion of surplus ethanol feedstock as opposed to predetermined generation on an industrial scale. In addition, it is commonly accepted as far less practical and less cost effective.

Catalysts for dehydrogenation include copper, operating at an elevated temperature but below 250 °C. The copper may have its surface area increased by depositing it on zinc, promoting the growth of snowflake, fractal like, structures. This surface area can be again increased by deposition onto a zeolite, typically ZSM-5. Zeolites (Greek zein, "to boil" lithos, "a stone" are hydrated Aluminosilicate Minerals and have a micro-porous structure Traces of rare earth metals or alkalies, such as that of sodium and potassium, have also been found to be beneficial to the process. Byproducts of hydrogenation include diethyl ether (thought to primarily arise due to aluminum sites in the catalyst), acetaldehyde, acetaldehyde aldol products, higher esters and ketones. Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a Acetaldehyde and MEK complicate conversion and purification as ethanol forms an azeotrope with water, as does ethyl acetate with ethanol and water and MEK with both ethanol and the acetate. Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula C[[Hydrogen H]]3CH O or MeCHO Butanone is a manufactured organic chemical. It is a colorless liquid with a sharp sweet butterscotch odor reminiscent of Acetone. An azeotrope (pronounced To obtain a high purity product, these azeotropes must be "broken", and this can be achieved by making use of pressure swing distillation.

The composition of the distillate removed from the conversion products is biased towards acetate at atmospheric pressure and ethanol at increased pressure. First, the raw product is fed into a high pressure column where the bulk of the contaminating ethanol is removed. By then feeding the ethanol depleted distillate into a low pressure column, the acetate can be removed from the remaining ethanol azeotrope.

MEK forms during the conversion process from 2-butanol. The latter fails to form an azeotrope with the acetate and so MEK can be removed by hydrogenation of the contaminated product over nickel and further distillation to strip away 2-butanol. This provides the simultaneous benefit of removing the acetylaldehyde contaminant by returning it to an ethanol form and is easily accomplished as hydrogen is a byproduct of the initial dehydrogenation process.

It may also be possible to break the azeotropes with the use of membrane distillation, molecular sieves, an entrainer or absorption medium.

The distilled ethanol and rehydrogenated contaminants can then be recycled into the raw feedstock.

Uses

Solvent

Ethyl acetate is primarily used as a solvent. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. For example, it is commonly used to dissolve the pigments for nail varnishes, and is responsible for the solvent-effect of some nail varnish remover (acetone and acetonitrile are also used). Nail polish or nail varnish is a Lacquer that is applied to the nails of both the Fingers and Toes usually cosmetically but also as Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Acetonitrile (ACN is the Chemical compound with formula CH3CN Industrially it is used to decaffeinate coffee beans and tea leaves. Decaffeination is the act of removing Caffeine from coffee beans, mate, Cocoa, Tea leaves and other caffeine-containing materials It is also used in paints as an activator or hardener.

In the laboratory, a mixture of ethyl acetate and hexane is the most common solvent system used as a chromatography solvent. Chromatography (from Greek χρώμα chroma, color and γραφειν"graphein" to write is the collective term for a family of Laboratory It is also used as a solvent for extractions. Liquid-liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds based on their relative solubilities in two It is rarely used as a reaction mixture because it is prone to hydrolysis. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions

Like most simple esters, ethyl acetate has a fruity smell. Ethyl acetate is present in confectionery, perfumes, and fruits. In perfumes, it evaporates quickly, leaving but the scent of the perfume on the skin.

Occurrence in wines

Ethyl acetate is present in wines. It may be considered a contaminant at too high concentrations, as typically occurs when wine is exposed to air for a prolonged period. When present at too high concentration in wine, it is regarded as an off-flavor. Wine is an Alcoholic beverage made from the fermentation of Grape juice

Other uses

In the field of entomology, ethyl acetate is an effective poison for use in insect collecting and study. Entomology (from Greek grc ἔντομος entomos, "that which is cut in pieces or engraved/segmented" hence "insect" and grc -λογία Insect collecting is historically a widespread essential predecessor of scientific Entomology and at the same time the formerly popular (until the mid-20th century educational In a killing jar charged with ethyl acetate, the vapors will kill the collected (usually adult) insect quickly without destroying it. A killing jar is a device used by Entomologists to kill captured Insects quickly humanely and with minimum damage Because it is not hygroscopic, ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection. Hygroscopy is the ability of a substance to attract Water Molecules from the surrounding environment through either absorption or Adsorption

Reactions

Ethyl acetate can be hydrolyzed in acid or basic conditions to regain acetic acid and ethanol. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions The use of an acid catalyst such as sulfuric acid gives poor yields due to it being an equilibrium — the reverse reaction of the Fischer esterification. Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid.

To obtain high yields, it is preferable to use a stoichiometric amount of strong base, such as sodium hydroxide. Sodium hydroxide ( Na[[hydroxide OH]]) also known as Lye, caustic soda and (incorrectly according to IUPAC nomenclature This reaction gives ethanol and sodium acetate, which is not able to react with ethanol any longer:

CH₃CO₂C₂H₅ + NaOH → C₂H₅OH + CH₃CO₂Na

References

Chembytes e-zine - Team effort: Steve Colley describes work to develop a new route to make ethyl acetate starting from low grade renewable feedstocks (2001)[1]

Ingenia Online - Renewable Processing: The Green Alternative; Using Bio-Ethanol To Manufacture An Industrial Solvent by Mike Ashley (Issue 29, 2006)[2]

Some industrial plants use Ethylene----> Acetic Acid in the presence of an tungstasilic acid on a silica support. Sodium acetate, (also sodium ethanoate) is the Sodium salt of Acetic acid. This is the catalyst and the Exothermic reaction is cooled by water/ethanol/acetic acid.

External links

Dictionary

-noun

(organic chemistry) The ethyl ester of acetic acid; CH₃COOCH₂CH₃

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