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Industrial methods for the synthesis of ethyl acetate include:

Distillation of a mixture of ethyl alcohol, acetic and sulfuric acids.
Treatment of ethyl alcohol with ketene.
According to the Tishchenko reaction from acetaldehyde at 0-5 °C in the presence of catalytic amounts of aluminum alcoholate:

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Physical properties

Colorless mobile liquid with a pungent odor of ether. Molar mass 88.11 g / mol, melting point -83.6 ° C, boiling point 77.1 ° C, density 0.9001 g / cm³, n 20 4 1.3724. Soluble in water 12% (by mass), in ethanol, diethyl ether, benzene, chloroform; forms double azeotropic mixtures with water (bp 70.4 °C, water content 8.2% by mass), ethanol (71.8; 30.8), methanol (62.25; 44.0), isopropanol (75.3; 21.0), CCl4 (74.7; 57), cyclohexane (72.8; 54.0) and a triple azeotropic mixture of E.: water: ethanol (b.p. 70.3 ° C, content respectively 83.2, 7.8 and 9% by weight).

Application

Ethyl acetate is widely used as a solvent, due to its low cost and low toxicity, and acceptable odor. In particular, as a solvent for cellulose nitrates, cellulose acetate, fats, waxes, for cleaning printed circuit boards, mixed with alcohol - a solvent in the production of artificial leather. Annual world production in 1986 was 450-500 thousand tons. The world production of ethyl acetate for 2014 is about 3.5 million tons per year.

It is used as a component of fruit essences. Registered as a dietary supplement E1504 .

Laboratory Application

Ethyl acetate is often used for extraction, and for column and thin layer chromatography. Rarely used as a reaction solvent due to its tendency to hydrolyze and transesterify.

Used to produce acetoacetic ester:

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Cleaning and drying

Commercially available ethyl acetate usually contains water, alcohol, and acetic acid. To remove these impurities, it is washed with an equal volume of 5% sodium carbonate, dried with calcium chloride and distilled. For higher requirements for water content, phosphoric anhydride is added several times (portions), filtered and distilled, protecting from moisture. With 4A molecular sieve, the water content of ethyl acetate can be reduced to 0.003%.

Security

Flash point - 2 °C, self-ignition temperature - 400 °C, concentration limits of vapor explosion in air 2.1-16.8% (by volume).

Transport safety. In accordance with ADR (ADR) hazard class 3, UN code 1253.

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Notes

An excerpt characterizing Ethyl acetate

I couldn’t bear it any longer and decided to talk to this unfortunate, clinging to each other, frightened couple of children whom fate suddenly, for no reason at all, threw out into some strange and completely incomprehensible world. And I could only try to imagine how scary and wild it all must have been, especially for this little baby, who still had no idea what death was ...
I approached them closer and quietly, so as not to scare, said:
Let's talk, I can hear you.
– Oh, Vidas, you see, she hears us!!! - the baby squealed. - And who are you? You are nice? Can you tell mom that we're scared?..
Words flowed in a continuous stream from her lips, apparently she was very afraid that I would suddenly disappear and she would not have time to say everything. And then she looked at the ambulance again and saw that the activity of the doctors had doubled.
- Look, look, they will take us all away now - but what about us ?!. - the little girl babbled in horror, completely unaware of what was happening.
I felt at a complete dead end, as the first time I encountered children who had just died and had no idea how to explain it all to them. The boy seemed to already understand something, but his sister was so terribly frightened by what was happening that her little heart did not want to understand anything at all ...
For a moment, I was completely lost. I really wanted to calm her down, but I couldn’t find the right words for this, and, afraid of making it worse, I kept silent.
Suddenly, a figure of a man appeared from the ambulance, and I heard one of the nurses shout to someone: “We are losing, we are losing!”. And I realized that the next to die was apparently the father ...
- Oh, daddy!!! - the girl squealed happily. - And I already thought you left us, and you are here! Oh how good!..
Father, not understanding anything, looked around, when he suddenly saw his wounded body and the doctors fussing around him, grabbed his head with both hands and howled softly ... It was very strange to watch such a big and strong adult man contemplating his death in such wild horror . Or maybe this is how it was supposed to happen? .. Because, unlike children, he just understood that his earthly life was over and nothing more could be done, even with the greatest desire ...
“Daddy, daddy, aren’t you happy? Can you see us? You can, right? .. - the daughter squealed happily, not understanding his despair.
And my father looked at them with such confusion and pain that my heart just broke ...
– My God, you too?!.. And you?.. – was all he could say. - Well, why are you?
In the ambulance, three bodies were already completely covered, and there was no longer any doubt that all these unfortunate people were already dead. So far, only one mother has survived, whose “awakening” I honestly admit, I did not envy at all. After all, seeing that she had lost her entire family, this woman could simply refuse to live.
- Dad, dad, and mom will wake up soon too? - As if nothing had happened, the girl asked happily.
The father stood in complete confusion, but I saw that he was struggling to gather himself in order to somehow calm his little daughter.
- Katenka, dear, mom will not wake up. She will no longer be with us,” my father said as calmly as possible.
- How will it not?! .. Are we all in the same place? We should be together!!! Isn't it? .. - little Katya did not give up.
I realized that it would be very difficult for a father to somehow explain to this little man - his daughter - that life had changed a lot for them and there would be no return to the old world, no matter how much she wanted to ... Father himself was in complete shock and , in my opinion, no less than a daughter needed consolation. The boy was the best so far, although I saw very well that he was also very, very scared. It all happened too suddenly, and none of them were ready for it. But, apparently, some kind of “masculinity instinct” worked for the boy when he saw his “big and strong” dad in such a confused state, and he, poor thing, purely like a man, took over the “reins of government” from the hands of his confused father into his own. small, shaking children's hands...
Before that, I had never seen people (except my grandfather) at the present moment of their death. And it was on that ill-fated evening that I realized how helpless and unprepared people meet the moment of their transition to another world! .. Probably the fear of something completely unknown to them, as well as the view of my body from the outside (but without their presence in it!) , created a real shock for those who did not suspect anything about it, but, unfortunately, already “leaving” people.
- Dad, dad, look - they are taking us away, and mom too! How can we find it now?
The little girl “shaked” her father by the sleeve, trying to attract his attention, but he was still somewhere “between the worlds” and did not pay any attention to her ... I was very surprised and even disappointed by such unworthy behavior of her father. No matter how frightened he was, a tiny man stood at his feet - his tiny daughter, in whose eyes he was the "strongest and best" dad in the world, whose participation and support she really needed at the moment. And to such an extent to become limp in her presence, in my opinion, he simply had no right ...

It dissolves well in alcohol, chloroform and ether, it dissolves worse in water, burns well, the explosive limit has a concentration in air of 2.2 - 9%. It is a solvent having a low cost, low toxicity, and an acceptable odor.

Ethyl acetate is obtained by:

Acetylation of ethyl alcohol with acetyl chloride or acetic anhydride. (Laboratory method)
. distillation of a mixture of ethyl alcohol, acetic and sulfuric acids. (Industrial way).
. treatment of ethanol with ketene. (Industrial way).
. according to the Tishchenko reaction from acetaldehyde at 0-5 °C in the presence of catalytic amounts of aluminum alcoholate. (Industrial way)

Specifications of ethyl acetate .

The name of indicators	Norm
Appearance of ethyl acetate	colorless, transparent liquid, free of mechanical impurities
Density of ethyl acetate at 20 °C, g/cm*3	0,898-0,900
Chromaticity of the Hazen unit	5
Mass fraction of the main substance, %, not less than	99,0
Mass fraction of acetic acid, %, no more	0,004
Mass fraction of non-volatile residue, %, max	0,001
Temperature limits for the distillation of ethyl acetate at a pressure of 760 mm. rt. Art., ° С	75-78
Mass fraction of water, %, no more	0,1
Relative volatility (by ethyl ether)	2-3
Mass fraction of ethyl alcohol	is absent

Characteristics of ethyl acetate by brand and grade.

Name of indicator	ethyl acetate
	BUT		B
	top grade	1st grade	B
Appearance	Transparent liquid without mechanical impurities
Chromaticity, Halen units, no more	5	10	10
Density at 20 0С, g/cm3	0,898-0,900	0,897-0,900	0,890-0,900
Mass fraction of the main substance, %	at least 99	at least 98	91±1
Mass fraction of acids in terms ofacetic acid, %, no more	0,004	0,008	0,01
Mass fraction of non-volatile residue, %, no more	0,001	0,003	0,007
Temperature limits of distillation atpressure 101.3 kPa 93% (by volume)product must be distilled withintemperature, 0С	75-78	74-79	70-80
Mass fraction of water, % no more	0,1	0,2	1
Mass fraction of aldehydes inrecalculation foracetaldehyde, % no more	0,05	not marked	-

Ethyl acetate is used in the following industries:

As a solvent in the production of paints and varnishes and inks for printing machines;
. as a solvent in the manufacture of adhesive compositions;
. at the stage of packaging various goods with flexible packaging materials - as an ink solvent when applying inscriptions and images by screen printing;
. as a reagent and as a reaction medium in the production of pharmaceuticals (methoxazole, rifampicin, etc.);
. as a degreasing agent in the production of aluminum foil and thin aluminum sheets;
. as a cleaning and degreasing agent in the electronics industry;
. as a solvent for cellulose ethers;
. mixed with alcohol as a solvent in the production of artificial leather;
. as an extracting agent for various organic substances from aqueous solutions. Due to its low toxicity, ethyl acetate is used in the food industry, for example, to extract caffeine from coffee.
. as a gelling agent in the manufacture of explosives;
. as a component of fruit essences;

Ethyl acetate (acetic acid ethyl ester)

ethyl acetate(acetic acid ethyl ester) is a colorless liquid with a characteristic odor. The literature indicates that ethyl acetate and butyl acetate have a fruity odor. Maybe. But most people who work directly with ethyl acetate are more inclined to think that its smell resembles acetone, with a slightly sweeter tint. Ethyl acetate is a classic representative of esters (group No. 3 in the classification of solvents for the paint and varnish industry. See the "Products" section).

Ethers- organic substances formed during the interaction of alcohols and acids. Alcohol + acid = ether + water. (See Butyl Acetate section for more details.) Ethyl acetate is the result of the esterification of ethyl alcohol and acetic acid. All esters are practically insoluble in water, but interact with water, reacting (hydrolysis of esters is the reverse process of esterification).

As a result, an equilibrium system is formed - on the one hand, ether and water, on the other hand, alcohol and acid. Although ethyl acetate does not contain water, but due to storage conditions (condensate in containers) or as part of mixed solvents where water may be present (this is a solvent R-646, R-645, R-649, R-650 i.e. practically all solvents in which there are alcohols) ethyl acetate, interacting with water, decomposes into its original components - acetic acid and ethyl alcohol. That is why in solvents which include esters, acidity increases over time.

And ethyl acetate better than butyl acetate mixes with water and interacts more actively with it. In the early 90s, some talented chemistry students used ethyl acetate to extract ethyl alcohol. If anyone remembers, it was hard with alcohol in stores, and there was a lot of cheap ethyl acetate. Ethyl acetate + water = ethyl alcohol + acid. Neutralize the acid and distill the resulting mixture. Everyone was fine.

ethyl acetate mixes well with alcohols, acetone, toluene, orthoxylene, solvent, i.e. with all organic solvents. Dissolves cellulose ethers, oils, fats, chlorinated rubbers, vinyl polymers, carbinol resins, etc. Almost everything is the same as acetone, methyl acetate, butyl acetate. By dissolving power ethyl acetate close to acetone, but weaker than it, however, stronger than butyl acetate. The addition of a small amount of alcohols enhances the dissolving power of ethyl acetate.

Raw materials for production. To obtain ethyl acetate, technical acetic acid and ethyl alcohol are used.

consumption of ethyl acetate. Up to 90% of all ethyl acetate produced is consumed by the paint and varnish industry (enamels, paints, varnishes, primers, adhesives, solvents). The remaining volume is used in the production of artificial leather, rubber goods, plastics and pharmaceuticals, cosmetics and the food industry.

Manufacturers. OJSC Nevinnomyssky Azot, Nevinnomyssk, Stavropol Territory (among other things, a producer of acetic acid and butyl alcohol) is part of OJSC Eurochem, OJSC Ashinsky Chemical Plant, Chelyabinsk Region, OJSC Karbokhim, Perm, OJSC Amzinsky Lesokombinat Amzya Bashkiria, FKP "Plant named after Ya.M. Sverdlov", Dzerzhinsk.

Ethyl acetate GOST 8981-78

Name of indicator	Norm according to GOST for grade "A"
Name of indicator	Top grade	First grade
1. Appearance	Transparent liquid without mechanical impurities
2. Chromaticity, Hazen units, no more	5	10
3. Density at 20°С, g/cm	0,898-0,900	0,897-0,900
4. Mass fraction of the main substance % not less than	99,0	98,0
5. Mass fraction of acids in terms of acetic acid,%, no more	0,004	0,008
6. Mass fraction of non-volatile residue,%, no more	0,001	0,003
7. Temperature limits of distillation at a pressure of 101.3 kPa (760 mm Hg): 95% (by volume) of the product must be distilled within the temperature range, C °	75 - 78	74 - 79
8. Mass fraction of water, %, no more	0,1	0,2
9. Mass fraction of aldehydes in terms of acetaldehyde,%, not more than	no more than 0.05%	Not standardized
10. Relative volatility (by ethyl ether)	2 - 3	2 - 3

Ethyl acetate (Ethyl ester of acetic acid) can be bought at our warehouse, near Podolsk and Klimovsk

Organic chemistry originated as the chemistry of natural compounds isolated from organisms of animal and plant origin. The filling of various classes of substances with natural compounds is random in nature and is determined by biosynthesis (Kartsova A.A., 2005).

The first task of organic synthesis is the artificial production of useful substances by copying natural structures. This is preceded by the stage of isolation of a natural compound, the study of its properties, and, finally, organic synthesis itself - the reproduction in a research laboratory of what was created in the laboratory of nature. Well, then you need to go further - to synthesize what is absent in nature.

Every day, 100 thousand new chemical compounds are synthesized in the world, 97% of which are organic substances.

I decided to consider the synthesis of ethyl acetate by the esterification reaction.

Ethyl acetate is ethyl acetate, which is widely used in medicine and veterinary medicine, in the printing industry; as a solvent to give the necessary consistency to the paint, hardener to fix the paint, furniture varnish. It is also used as an extractant of organic compounds from aqueous solutions, a gelling agent in the production of explosives; is part of the industrial heat-sealing adhesive. World production of ethyl acetate 0.45-0.5 million tons per year (1986) (Reed R. et al., 1982)

One of the methods in the industry of ethyl acetate is the esterification of acetic acid with ethanol at 110-115 ° C in the presence of sulfuric acid.

Therefore, the purpose of my work was to carry out the synthesis of ethyl acetate by the esterification reaction and study its properties.

Calcium chloride

Synthesis is carried out in the device shown in the figure. 2.5 ml of ethyl alcohol is poured into a 100 ml Wurtz flask equipped with an addition funnel and connected to a descending condenser, and then 1.5 ml of concentrated sulfuric acid is carefully added with stirring. The flask is closed with a stopper into which an addition funnel is inserted. And heated in an oil (or metal) bath to 140 ° C (the thermometer is immersed in the bath). A mixture of 2 ml of ethyl alcohol and 4.5 ml of glacial acetic acid is gradually poured into the flask from a dropping funnel. The influx should be carried out at the same speed as the forming ether is distilled off. At the end of the reaction (after stopping the distillation of the ether), the shoulder strap is transferred to a separating funnel and shaken with a concentrated soda solution to remove acetic acid. The upper ether layer is separated and shaken with a saturated solution of calcium chloride (to remove alcohol, which gives with calcium chloride a crystalline molecular compound CaCl2 * C2H5OH, insoluble in acetic ethyl ether). After separating the ether, it is dried with calcined calcium chloride and distilled in a water bath from a flask with a reflux condenser. At a temperature of 71-75 ° C, a mixture of alcohol and ethyl acetate will be distilled off, at 75-78 ° C, almost pure acetic ethyl ester passes. The yield is 20 g (65% theoretical) (Glodnikov G.V., Mandelstam, 1976).

results

1. Reaction mechanism.

The production of ethyl acetate is based on the esterification reaction, as a result of which an ester is formed when acetic acid is heated to 140-150 0C with ethyl alcohol in the presence of a catalyst - sulfuric acid.

General reaction equation

The role of the catalyst is to protonate the carbonyl oxygen: in this case, the carbonyl carbon atom becomes more positive and more "vulnerable" to attack by the nucleophilic agent, which is the alcohol molecule. The cation formed first attaches the alcohol molecule at the expense of the lone electrons of the oxygen atom, giving the cation:

The cation, as a result of the elimination of a proton, forms an ester molecule;

The use of the method of "tagged atoms" made it possible to solve the problem of the place of bond breaking in the esterification reaction. It turned out that usually a water molecule is formed from the hydroxyl of an acid and the hydrogen of an alcohol. Consequently, in an acid molecule, the bond between acyl and hydroxyl is broken, and in an alcohol molecule, the bond between hydrogen and oxygen is broken. Such a conclusion follows from the results of work on the esterification of benzoic acid with methanol containing the heavy oxygen isotope O18. The resulting ester contained the indicated oxygen isotope:

The presence of O18 was established by burning an ether sample and analyzing the resulting combustion products (CO2 and H2O) for the presence of a heavy oxygen isotope (Tyukavkina N.A., Baukov Yu.I., 2004).

The esterification reaction is a reversible process, therefore, in order to avoid hydrolysis of the resulting product, the ether was distilled off using a direct refrigerator.

The hydrolysis of esters is the reverse reaction of their transformation. Hydrolysis can be carried out in both acidic and alkaline conditions. For the acid hydrolysis of esters, everything that was said above in relation to the esterification reaction, about the reversibility and mechanism of the process, and about the methods of shifting the equilibrium is true. The alkaline hydrolysis of esters goes through the following steps:

Practically, alkaline hydrolysis of esters is carried out in the presence of caustic alkalis KOH, NaOH, and alkaline earth metal hydroxides Ba(OH)2, Ca(OH)2. The acids formed during hydrolysis bind in the form of salts of the corresponding metals, so the hydroxides have to be taken at least in an equivalent ratio with the ester. Usually an excess of base is used. The separation of acids from their salts is carried out with the help of strong mineral acids.

During the synthesis, the establishment of chemical equilibrium is possible. According to the Le Chatelier principle, in order to shift the equilibrium towards the formation of the reaction product, the addition of a mixture of ethyl alcohol and glacial acetic acid was carried out at the same rate as the forming ester was distilled off. The synthesis temperature did not exceed 150 0C.

When the temperature rises above the specified value, the reaction of intramolecular dehydration is possible:

As a result of the experiment, a colorless liquid with a characteristic odor was obtained. After cessation of the release of the ether, the resulting product was transferred to a separating funnel and shaken with a concentrated soda solution to remove acetic acid.

To remove alcohol, the upper ethereal layer was separated and shaken with a saturated solution of calcium chloride. Ethyl alcohol gives with calcium chloride a crystalline molecular compound of the composition CaCl2 * C2H5OH, insoluble in acetic ethyl ether. After separating the ether, it was dried with calcined calcium chloride.

2. Research results.

The yield (%) of ethyl acetate in the reaction was calculated. According to the law of conservation of mass and energy, the theoretical yield of ether is 6.3 g (7.0 ml). As a result of the synthesis, 4.5 ml (4.05 g) of ethyl acetate were obtained. The yield of the reaction product (acetic acid ethyl ester) is 64.29%.

To identify and determine the purity of the resulting ethyl acetate, the angle of refraction was determined using a refractometer. According to the literature, pure acetic ethyl ether has a refractive angle of 1.3722. (Rid R. et al., 1982). In our case, the refractive angle of ethyl acetate was 1.3718. This value is close to the reference data, which indicates a sufficient degree of purity of the obtained product.

Ethyl acetate (acetic acid ethyl ester) 88 0.9 1.3722 1.3718 64.29

As a result of the synthesis (esterification of acetic acid with ethyl alcohol in the presence of sulfuric acid at a temperature of 140 - 150 0C), an ester was obtained - ethyl acetate, which was a transparent liquid with a characteristic odor. To identify the product, the refractive angle of ethyl acetate (1.3718) was measured, which is close to the reference data. The yield of ethyl ester of acetic acid was 64.29%.

Structural formula

True, empirical, or gross formula: C4H8O2

Molecular weight: 88.106

ethyl acetate- (acetic acid ethyl ester) CH 3 -COO-CH 2 -CH 3 - a colorless volatile liquid with a pungent odor.

Receipt

Ethyl acetate is formed by the direct reaction of ethanol with acetic acid:
CH 3 COOH + C 2 H 5 OH → CH 3 COOC 2 H 5 + H 2 O
The laboratory method for obtaining ethyl acetate is to acetylate ethyl alcohol with acetyl chloride or acetic anhydride:
CH 3 COCl + C 2 H 5 OH → CH 3 COOC 2 H 5 + HCl
Industrial methods for the synthesis of ethyl acetate include:
Distillation of a mixture of ethyl alcohol, acetic acid and sulfuric acid. Treatment of ethyl alcohol with ketene. According to the Tishchenko reaction from acetaldehyde at 0-5 °C in the presence of catalytic amounts of aluminum alcoholate:
2CH 3 CHO → CH 3 COOC 2 H 5

Physical properties

Colorless mobile liquid with a pungent odor of ether. Molar mass 88.11 g/mol, melting point −83.6 °C, boiling point 77.1 °C, density 0.9001 g/cm³, n204 1.3724. Soluble in water 12% (by mass), in ethanol, diethyl ether, benzene, chloroform; forms double azeotropic mixtures with water (bp 70.4 °C, water content 8.2% by mass), ethanol (71.8; 30.8), methanol (62.25; 44.0), isopropanol (75.3; 21.0), CCl4 (74.7; 57), cyclohexane (72.8; 54.0) and a triple azeotropic mixture of E.: water: ethanol (b.p. 70.3 ° C, content respectively 83.2, 7.8 and 9% by weight).

Application

Ethyl acetate is widely used due to its low cost and low toxicity, as well as an acceptable odor. In particular, as cellulose nitrates, cellulose acetate, fats, waxes, for cleaning printed circuit boards, mixed with alcohol - in the production of artificial leather. Annual world production in 1986 was 450-500 thousand tons. The world production of ethyl acetate for 2014 is about 3.5 million tons per year.
One of the most popular poisons used in entomological stains to kill insects. Insects after killing in its vapors are much softer and more pliable in preparation than after killing in chloroform vapors. It is used as a component of fruit essences. Registered as food additive E1504.

Laboratory Application

Ethyl acetate is often used for extraction, as well as for column and thin layer chromatography. Rarely used for reactions due to tendency to hydrolysis and transesterification. Used to obtain acetoacetic ester:
2CH 3 COOC 2 H 5 → CH 3 COCH 2 COOC 2 H 5

Cleaning and drying

Security

The LD 50 for rats is 11.6 g/kg, showing low toxicity. Ethyl acetate vapors irritate the mucous membranes of the eyes and respiratory tract, and when exposed to the skin cause dermatitis and eczema. MPC in the air of the working area is 200 mg/m³. MPC in the atmospheric air of populated areas is 0.1 mg/m³. Flash point - 2 °C, self-ignition temperature - 400 °C, concentration limits of vapor explosion in air 2.1-16.8% (by volume). Transport safety. In accordance with ADR (ADR) hazard class 3, UN code 1253.