Properties characteristic of acetone. Acetone: formula, properties, application

Acetone - (from Latin acetum - vinegar) (2-propanone, dimethyl ketone) CH 3 COCH 3, molecular weight 58.079; volatile colorless liquid with a characteristic odor; melting point -94.6°C, boiling point 56.1°C. a widely used solvent for organic substances, primarily nitrates and cellulose acetates; due to its relatively low toxicity, it is also used in the food and pharmaceutical industries; acetone also serves as a raw material for the synthesis of acetic anhydride, ketene, diacetone alcohol, oxide, mesityl, methyl isobutyl ketone, methyl methacrylate, diphenylolpropane, isophorone and many other compounds. Miscible with water and organic solvents, such as ether, methanol. ethanol esters.
It also has all the chemical properties characteristic of aliphatic ketones. Forms crystalline compounds with alkali metal hydrosulfites. for example with NaHSO 3 - (CH 3) 2 C(OH)SO 3 Na. Only strong oxidizing agents. for example, an alkaline solution of KMnO 4 and chromic acid oxidize acetone to acetic and formic acids and then to CO 2 and water. It is catalytically reduced to isopropanol by amalgams of Mg or Zn, as well as Zn with CH 3 COOH - to pinacone (CH 3) 2 C(OH)C(OH)(CH3)2. Hydrogen atoms are easily replaced during halogenation. nitrosation, etc. By the action of chlorine and alkali, acetone is converted into chloroform, which reacts with acetone to form chloroethone (CH 3) 2 C(OH)CCl 3, used as an antiseptic. Technical acetone is obtained by the cumene method in the process of phenol synthesis, by the method of acetone-butyl fermentation, and also as a by-product in a number of industries. Acetone is used in the paint and varnish industry, is used in the production of plastics, synthetic rubber and chemical fibers, and serves as a raw material for the synthesis of many other organic products. It is used in the production of acetic anhydride, acetone cyanohydrin, diphenylolpropane, for degreasing surfaces, as a solvent in various industries.

Production of acetone in industry.

Acetone is obtained in several ways:
Udris-Sergeev method or cumene method.
It is carried out in three stages. In the first stage, benzene is alkylated with propylene to isopropylbenzene (cumene), which is then oxidized with oxygen in an alkaline medium at 130°C to cumyl hydroperoxide. As a result of hydrolysis of the latter in an acidic environment at 60°C, the final products of the process are formed - phenol and acetone:
C6H6 + CH3CH=CH2 --> C6H5CH(CH3)2
C6H5CH(CH3)2 + O2 --> C6H5C(CH3)2OOH
C6H5C(CH3)2OOH --> C6H5OH + (CH3)2C=O
- Oxidation of isopropyl alcohol in the vapor phase at 450-650°C in the presence of metallic copper, silver, nickel or platinum:
(CH3)2CHOH + 1/2O2 --> (CH3)2C=O + H2O
- autocatalytic oxidation of isopropanol in the liquid phase at 90-140°C and 0.2-0.3 MPa. In addition to acetone, the product of the process is hydrogen peroxide:
(CH3)2CHOH + O2 --> (CH3)2C=O + H2O2
- Direct oxidation of propylene in the liquid phase in the presence of palladium chloride PdCl2 at 50-120°C and 5-10MPa:
CH3CH=CH2 + PdCl2 + H2O --> (CH3)2C=O + Pd + 2HCl
Pd + 2HCl + 1/2O2 --> PdCl2 + H2O

Application

Technical acetone is widely used in the paint and varnish industry as a solvent for nitro varnishes, nitro enamels (in the production of aviation, automobile, cable, leather and other varnishes), in the production of cellulose acetate and nitrocellulose, in the production of certain types of artificial silk, in the production of organic unbreakable glass, in the production of film films , smokeless powder, celluloid, Akrikhin and others.
The ability of acetone to dissolve acetylene is used on a large scale when filling steel cylinders in which acetylene is stored, used for welding metals. Acetylene is absorbed by the porous material impregnated with acetone; at a pressure of 15 atm. 1 volume it dissolves 375 volumes of acetylene.
The use of acetone to extract wax from lubricating oils is becoming increasingly important. Acetone serves as a raw material for the production of many chemical products: synthetic rubber, indigo, ionone (perfume), sulfonal (hypnotics). Compounds of acetone with salts of sulfurous and hydrosulfuric acids are used in dyeing and printing fabrics.
Technical acetone is used in the production of artificial leather, for disinfecting wool and fur, and for extracting essential oils. Pure acetone is used in the food industry for the extraction of food products, vitamins, and fats; for the extraction of certain drugs and the preparation of pharmaceuticals requiring a chemically pure solvent with a low boiling point.
It is also used for degreasing surfaces or products used in industry and everyday life. Acetone is widely used in industry as a solvent for extracting a number of substances, for recrystallizing chemical compounds, dry cleaning, producing chloroform, etc. Acetone vapor is heavier than air. Therefore, in rooms where acetone evaporates, there is a danger of poisoning when inhaling its vapors, it is used in the paint and varnish industry, is used in the production of plastics, synthetic rubber and chemical fibers, and serves as a raw material for the synthesis of many other organic products. It is used in the production of acetic anhydride, acetone cyanohydrin, diphenylolpropane, for degreasing surfaces, as a solvent in various industries. Acetone is transported by all types of transport in accordance with the cargo transportation rules in force for this type of transport. Air transport is carried only on cargo ships with a maximum net volume per package of 60 dm 3. They are transported by rail in barrels in covered wagons (wagonload or small shipments). When transporting acetone in barrels with a capacity of 100 dm 3 in covered railway cars, river and sea transport, transportation is carried out in packages in accordance with the rules for the transportation of goods. Acetone in bottles is transported only by road.

Acetone detection

In chemical-toxicological analysis, reactions with solutions of iodine, sodium nitroprusside, furfural, o-nitrobenzaldehyde and the microdiffusion method are used to detect acetone.
Reaction of formation of iodoform. When acetone reacts with iodine solution in an alkaline medium, iodoform is formed: Carrying out the reaction. To 1 ml of the test solution add 1 ml of 10% ammonia solution and a few drops of iodine and potassium iodide solution. In the presence of acetone, a yellow precipitate of iodoform is formed with a characteristic odor, and its crystals have a characteristic shape.
Detection limit: 0.1 mg acetone per sample.
Ethyl alcohol also gives this reaction.

Precautionary measures

According to the degree of impact on the body, acetone belongs to the 4th hazard class. With prolonged inhalation of vapors, acetone accumulates in the body and can be absorbed through intact skin. Acetone poisoning is possible when inhaling acetone vapor in a concentration exceeding the maximum permissible concentration (200 mg/m3).
According to its pharmacological properties, acetone is one of the substances that exhibit a narcotic effect. It has cumulative properties. Acetone is slowly eliminated from the body. It can enter the body with inhaled air, as well as through the alimentary canal and skin. After acetone enters the blood, part of it passes to the brain, spleen, liver, pancreas, kidneys, lungs and heart. The acetone content in these organs is slightly lower than in the blood. When working with technical acetone, the following precautions must be observed:
- protect from contact with the skin of your hands using rubber gloves;
- avoid contact with the mucous membranes of the eyes;
- work using acetone should be carried out in well-ventilated areas, or using protective breathing masks;
If acetone gets on your skin, you should quickly wash it off with plenty of warm water and soap.

Acetone toxicity and prevalence of poisoning

Acetone is relatively low toxic. Nelson et al. found that the maximum permissible concentration of acetone in air for an 8-hour exposure was 0.02%. Drinker and Cook believe that the maximum permissible concentration of acetone is 0.05-0.25%. Smith and Myers cite cases of acute poisoning by vapors of a mixture of acetone and butanone at concentrations of the order of 0.1%. Unpublished research by Sterner, Oglesby and Fassett showed that of all the solvents used in industry, acetone is one of the least toxic and in this respect is quite comparable to ethyl alcohol. Currently, the maximum permissible concentration is considered to be 0.1%. Staying for a short time in an atmosphere in which the concentration of acetone is much higher than specified does not cause harm.
The flammability limits in air are 2.55-12.8 vol.%.
Acetone is a natural metabolite of the human and animal body. It is part of a triad of compounds (beta-hydroxybutyrate, acetoacetate and acetone) referred to as ketone bodies. Acetone is formed by the non-enzymatic decarboxylation of acetoacetic acid. Under normal conditions, the content of acetone in human blood serum usually does not exceed 6 mg/l (0.1 mmol/l). A three-day fast leads to an increase in serum acetone concentration in obese individuals to 17 mg/l, and in healthy non-obese individuals to 44 mg/l
Under conditions of glucose deficiency (fasting) or when its bioavailability decreases (diabetes mellitus), the content of ketone bodies in the blood can increase tenfold. At the same time, they also act as part of a feedback regulatory mechanism, blocking the excessive mobilization of fatty acids from adipose tissue and thereby weakening the toxic effect of the latter.
The toxicity of acetone entering the body from the outside has been well studied. Acute toxicity of acetone (LD50) entering through the stomach is, according to various authors, for rats - 5.8-9.8 g/kg, for mice - 3.0-5.25 g/kg, for rabbits and dogs - 3 .8-8.0 g/kg. In this indicator, acetone differs little from ethanol.
The effective single effective dose (EDmin) of acetone for humans, determined by its effect on the nervous system, kidneys and blood when administered through the stomach, is 2.9 g/kg.
The dose with minimal toxic effect (MDx.), determined in rats subject to intragastric administration of acetone for 6 months. is 7 mg/kg.
Its maximum permissible concentration (MPC) in public water is 2.2 mg/l.
The toxic effect of acetone is associated with a narcotic effect on the central nervous system, a cauterizing effect on the mucous membrane of the respiratory tract and digestive organs, metabolic acidosis and a negative effect on fetal development.

Acetone is one of the most common solvents in construction. It is used for dilution, primarily of acetates and nitrates, and due to its fairly low toxicity level it is also used in the food and pharmaceutical industries. Acetone is also a raw material for the synthesis of vinegar anhydride, methyl methacrylate, isophron, methyl isobutyl ketone, oxide, ketene, mesityl, diacetone alcohol and other compounds.

Acetone is a volatile and colorless substance. It is a hygroscopic liquid with a characteristic, pronounced odor. It can also be mixed with ethanol, chloroform, methanol, water, diethyl alcohol and other organic solvents in a wide variety of ratios and proportions.

This chemical has the same qualities and features as aliphatic ketones. It can be catalytically reduced by zinc and magnesium amalgams to isopropyl alcohol. Acetone can also oxidize secondary alcohols to ketones in the absence of aluminum alkoxides.

Its main technical features and characteristics:

Density - 790.8 kg/m3;

Melting point - 94.90 C;

Boiling point - 56.20 C.

Under industrial conditions and scale, this substance is released during the production of acetic acid, film, plexiglass, varnishes, plastics and paints.

From a medical point of view, acetone is a real drug. Parts of it are used by substance abusers in order to achieve a state of euphoria. However, this substance is very dangerous and can affect the entire central nervous system.

Poisoning of the body can occur if this substance is ingested by inhaling its concentrated vapors. The lethal dose is 60 ml or more. If acetone enters the body, symptoms such as abdominal pain, cyanosis of the skin, vomiting, and nausea may occur. If a large amount enters the body, loss of consciousness may occur, and death occurs approximately 7 to 12 hours after ingestion of this substance.

Today, acetone is one of the most popular products, which is actively used in the production and manufacture of paints and varnishes, in painting works, construction, in the chemical industry, and also as an effective and inexpensive solvent for paints and other substances.

Every day its use is becoming increasingly important for removing wax from lubricating oils, for degreasing wool and fur, in the production of artificial leather, as well as for the effective extraction of various essential oils. In addition, acetone is actively used when filling cylinders in order to store acetylene. One volume of this substance dissolves approximately 25 volumes of acetylene under normal pressure and temperature.

This substance must be stored in glass, plastic or metal bottles in places that are reliably protected from sparks or sunlight. Premises for storing acetone should also be well ventilated and ventilated. In addition, you need to ensure that acetone is not available to small children.

ACETONE, dimethyl ketone, chemical composition CH 3 · CO · CH 3, the simplest representative of the ketone group; plays a very important role in various branches of the chemical industry, where it is used either as a solvent or as a starting material for the preparation of valuable chemicals. Known since 1732 as a product of dry distillation of salts of acetic acid and was formerly called pyroacetic ether (Pyroessigather). Its composition was first determined by Liebig and Dumas (in 1832), and Williamson established the present formula of the structure, which was later confirmed by the synthesis of acetone from zincmethyl and acetyl chloride. The first production of acetone was carried out in Austria, which until the 90s of the 19th century. was his main supplier. Recently, due to the increasing need for acetone and the development of new cheap methods for its production, acetone production has become firmly established in France, England and the USA.

Physical and chemical properties of acetone. Colorless, easily mobile liquid with an odor slightly reminiscent of mint, boiling point at 760 mm 56°.2; melting point - 94°.9; flash point 18°; critical temperature 232°.6; critical pressure 522 atm; specific gravity (at 15°) 0.79726; latent heat of evaporation for 1 kg 125.28 Cal (at 56°.2).

Acetone not only easily mixes in any ratio with water, alcohol, ether, gasoline and many other organic solvents, but, when added to two solvents that do not mix with each other, transforms them into a homogeneous solution. On the other hand, acetone is an excellent solvent for resins, fats, tannic acids and other organic compounds.

Chemically, acetone is a ketone, so it adds acid salts of sulfurous acid, ammonia; forms an oxime with hydroxylamine, and hydrazones with hydrazines; upon reduction, it turns into a secondary alcohol - isopropyl alcohol (CH 3) 2 CH·OH. Under the influence of certain catalysts, acetone condenses, giving various compaction products (phoron, mesityl oxide, etc.). Metallic sodium in an aqueous solution is reduced to dihydric alcohol - pinacone (CH 3) 2 · C (OH) · C (OH) · (CH 3) 2, which has recently found use as a starting product for the production of synthetic rubber. When exposed to halogens - chlorine or iodine - in the presence of solutions of caustic alkalis, acetone is converted into chloroform or iodoform (a sensitive reaction to acetone in the absence of ethyl alcohol).

Obtaining acetone. Among the various methods for producing acetone, the following are of technical importance: 1) methods based on the processing of dry distillation products of wood, 2) acetone fermentation of carbohydrates and 3) synthetic methods.

1) Raw wood alcohol, in the form in which it is obtained by dry distillation of wood, always contains acetone, the amount of which varies within certain limits, depending on the type of wood, conditions of dry distillation, etc.; On average, its content is 10-20% by weight of alcohol. When this raw alcohol is distilled in column stills, the first distillates containing about 50% acetone are obtained. Fractions are separated from these shoulder straps by repeated distillations; even richer in acetone, which, however, do not represent pure acetone, because they contain as impurities substances that have a boiling point close to acetone (methyl ester of acetic acid), and which therefore cannot be separated from acetone by distillation; therefore, for such industries where high purity acetone is required (for example, the preparation of pyroxylin, cordite, etc.), this product is not suitable. The oldest, but still most widespread, is the method of producing acetone, based on the thermal decomposition of calcium acetate, the so-called. “vinegar powder” - a product of dry distillation of wood obtained by neutralizing acetic acid with lime. The process of acetone formation is expressed by the equation (CH 3 COO) 2 Ca = CH 3 COCH 3 + CaCO 3, and occurs at a temperature of about 400°. Since technical calcium acetate - vinegar powder - contains, at best, 80% pure calcium acetate salt, then from 100 parts by weight, theoretically, 30 parts by weight of acetone should be obtained. In practice, however, the yield of acetone is significantly lower due to a number of side processes occurring along with the main reaction. Together with acetone, higher ketones (methyl ethyl ketone CH 3 · CO · C 2 H 5), aldehydes, acids, gaseous products (methane) and resins are formed. Therefore, the yield of acetone almost never exceeds 20-21% of the weight of vinegar powder (80%).

When the powder is heated in factory apparatus, distillation begins at 110-125°. First, the water in the vinegar powder is distilled, then water with a small amount of acetone, and finally, there is a short break in distillation, after which the actual decomposition of calcium acetate begins. At the same time, the color and specific gravity of the shoulder strap change, and abundant gas evolution begins. Distillation is continued until the formation of liquid distillate has almost completely ceased. After this, steam is passed into the retort in which the decomposition is carried out to completely remove the acetone. One of the oldest designs of apparatus for the factory production of acetone from vinegar powder is an iron or cast iron flat retort, equipped with a lid in which there are three holes: the first is used to load the powder, the other is connected to an outlet pipe, a dust collector and a refrigerator, and a stirrer is inserted into the third. The purpose of the dust collector is to retain fine dust formed when mixing the powder. Despite the presence of a dust collector, vinegar powder, due to its lightness, spreads throughout the room and clogs the distillate. In addition, when the powder comes into direct contact with the hot walls and bottom of the retort, b. or its strong burning, which is why the yield of acetone in devices of this type is 10-12% lower than in devices of new designs, where the powder is heated by radiant heat.

This is achieved by laying out the powder in a thin layer on shelves placed on a trolley. The trolley on rails rolls into a horizontal retort, which is evenly heated on all sides by flue gases. Distillation continues for 10-24 hours. At the end of it, steam is passed into the retort to decompose the remaining calcium acetate and to remove acetone, after which the trolley is replaced with a new one. In this way, process continuity is achieved. The yield of acetone is about 70% of theoretical.

In addition to these two types of devices, a third one is used in technology, which differs from them in that the powder is heated using superheated steam. In this case, any possibility of local overheating is eliminated, but the resulting acetone is strongly diluted with water (10% instead of 30-40%), which does not seem economically profitable, since some gain in yield is entirely covered by the costs associated with heat consumption for concentrating aqueous solutions of acetone. Acetone obtained by one of these methods is a liquid that separates into two layers: the lower one is light yellow, in which acetone predominates, and the upper one is oily, dark brown, consisting of higher ketones, resinous substances, hydrocarbons, phenols and other products . To purify acetone, raw material is treated with water in special drums with mixers. The oily, dark-colored substances released are separated, and an aqueous solution of acetone is neutralized with lime and subjected to rectification in column apparatuses. The first shoulder strap is collected within the temperature range of 54-60° - this is technically pure acetone (97%); the second goes between 60-85° - a liquid that, when mixed with water, releases higher ketones that are difficult to dissolve in water; the third is a mixture of water and yellow oil. After further processing and rectification, the first run produces chemically pure acetone, the second - a product boiling at a temperature of 70 to 120 °, mainly consisting of methyl ethyl ketone and called white acetone oil; from the third, yellow acetone oil is obtained with a boiling point from 120 to 250°.

2) The first observation of the formation of acetone from carbohydrates as a result of an enzymatic process (with the participation of Bacillus macerans) was made in 1905 by Schardinger. A number of research works, of which Fernbach's research at the Pasteur Institute deserves special attention, found that under the influence of certain types of microorganisms (Bacillus butylicus B. F., Granulobacter pectinovorum, B. acetoaethylicus) starch is converted into acetone and butyl alcohol. The practical application of fermentation to produce acetone dates back to 1912 (Fernbach and Strange, G. P. 323533). At the beginning of the imperialist war, the British government became interested in this method, as it needed large quantities of acetone to prepare a special type of smokeless gunpowder (cordite). Then, at the end of the war, the fermentation method began to be used in the United States, where it has now reached a great degree of perfection and has gained predominant importance. Various types of cereals, potatoes and many other substances containing starch can serve as the starting material for the production of acetone. In practice, however, corn is almost always used, since it contains a sufficient amount of nitrogen compounds necessary for the successful completion of the process.

According to one of the existing methods, acetone is produced as follows. After the corn is freed from the husk, it is ground and the flour is stirred in special devices with hot water (10 parts of water are taken for 1 teaspoon of flour), which is why the starch contained in the flour turns into a finely dispersed state and is partially hydrolyzed; This also achieves sterilization of the mass. The sterilized mixture is then pumped into fermentation tanks and, after cooling, a pure culture of Granulobacter pectinovorum is added. The fermentation tanks are equipped with hydraulic valves through which the gases formed during the process, consisting of carbon monoxide (60%) and hydrogen (40%), freely escape. During fermentation, sterile conditions are strictly observed and the temperature is maintained at 30-35°. At the end of fermentation, the resulting products (acetone, ethyl and butyl alcohol) are separated by distillation in column units. Acetone is distilled first, ethyl alcohol second, and then a mixture of butyl alcohol and water containing about 68% butyl alcohol. From such a waste stream, pure butyl alcohol is obtained by further processing. At the same time, from 1 bushel (36.4 l) of grain, 4.319 kg of useful product is obtained, consisting of 60% acetone, 30% ethyl and 10% butyl alcohol.

3) Synthetic acetone can be obtained in two ways: a) contact - from carbon monoxide and hydrogen (water gas) and b) from calcium carbide - through acetylene, acetaldehyde and acetic acid.

The contact method is the youngest of all existing methods for producing acetone. It arose in connection with the synthesis of methanol. Acetone is obtained, along with higher ketones, aldehydes and other compounds, with a certain change in the conditions for the synthesis of methyl alcohol from water gas; Acetone is separated from impurities by fractionation. That. acetone is a by-product here; There is no exact information regarding its release, but, judging by some data, the release may not be possible. big.

Regarding the intermediate stages of obtaining acetone from calcium carbide, see Acetylene, Acetaldehyde, Acetic acid. From the latter, acetone can be obtained by contact - by passing acetic acid vapor through barium carbonate or acetate or another catalyst. In this case, however, complete conversion does not occur: some of the acetic acid passes unchanged and requires additional processing. This circumstance and the formation of ethane that occurs as a side reaction are a great obstacle to the industrial implementation of this method. Of all the described methods for extracting acetone, fermentation is the most economically profitable: it does not require complex equipment, equipment costs are relatively low and cheap raw materials are used. The advantages of the fermentation method are so significant that, for example, in the USA, despite the highly developed industry of dry distillation of wood, acetone is almost exclusively obtained by fermentation. According to the latest American data, the cost of acetone does not exceed the cost of ethyl alcohol.

Application of acetone. Most of the acetone is used to dissolve and gelatinize nitrocellulose for the purpose of preparing smokeless powder and celluloid from it. Nitrocellulose in a small amount of acetone swells and turns into a gelatinous mass, which is easily rolled and shaped and is therefore especially suitable for various crafts. Its solutions in acetone are also used as glue. Since acetone is a good solvent for fats, resins, tannic acids and other organic substances, it is widely used for the extraction of these substances from plant products. Quite a lot of acetone is used to prepare autogas, obtained by dissolving acetylene in acetone. Products combining acetone with salts of sulfurous and hydrosulfuric acids are widely used in photography, printing and dyeing of fabrics as developers and reducing agents. Many artificial resins and plastics are obtained by condensation of acetone with casein and formaldehyde. Acetone is also used in paint and varnish production; in addition, it serves as a starting material for the preparation of a number of valuable organic products: chloroform, iodoform, sulfonal, ionone, synthetic indigo, isoprene and pinacone; the latter two, in turn, are the starting materials for the preparation of synthetic rubber.

See also:

• ACETONEMIA, the presence in the blood of a large amount of acetone, jS-hydroxybutyric acid and acetoacetic acid due to incomplete oxidation of metabolic products in debilitating diseases, such as diabetes (see), cancer, starvation, nervous and mental...
• ACETONE BODIES, a name that combines acetone, acetoacetic and |3-hydroxy-butyric acids into one group, due to the commonality of their formation in the body, the mutual connection of these three substances with chemicals. points of view and their ease...
• ACETONURIA, excretion of acetone in the urine. Acetone is usually found in very small quantities (about 0.01 g per day) in urine. Of the nutrients, the most important source of its formation is fats. Oxidation...
• ACETOPYRINE, akopirin, Antipyrinum acetylo-salicylicum, a compound of aspirin with antipyrine, white crystalline powder, faintly smelling of acetic acid; melting temperature 63-65°; dissolves in 20 parts of 2% sodium bicarbonate solution, in 30 parts of hot...
• ACETOACETIC ACID, SB„.SO. .CH2. COOH, a colorless, strongly acidic liquid, is miscible in all respects with water, alcohol and ether. When heated, it easily decomposes into carbon dioxide and acetone. For high-quality detection of A. c....

Pick up some nail polish remover (it seems like everyone has this substance in their house, or at least has come across it at least once). Most of them now have a bright inscription: no acetone. But not everyone knows anything other than the name about a chemical called acetone.

What is acetone?

The chemical formula of acetone is extremely simple: C 3 H 6 O. If a person was attentive in chemistry lessons, then perhaps he even remembers the class of chemical compounds to which this substance belongs, namely, a ketone. Or an attentive school student in the past may remember not only chemistry. the formula of acetone and the class of the compound, as well as the structural formula, which is presented in the figure below.

In addition to the structure, the formula of acetone also reflects its generally accepted name according to the IUPAC nomenclature: propanone-2. Although, again, it is worth noting that some readers may even remember the rules for naming chemicals from school.

What if we talk about what lies under the acetone formula in real life, and not in the picture with the formula or structure? Acetone under normal conditions is a volatile liquid without color, but with a characteristic pungent odor. You can be sure that almost every person is familiar with the smell of acetone.

History of discovery

Like any chemical substance, acetone has its own “parent”, that is, the person who first discovered the substance and wrote the first page in the history of the chemical compound. The “parent” of acetone is Andreas Libavi (photo below), who first identified it during the dry distillation of lead acetate. This happened no less than a little more than 400 years ago: in 1595!

However, this could not be a full-fledged discovery, because the chemical composition, nature, and formula of acetone could only be established 300 years later: only in 1832 were Jean-Baptiste Dumas and Justus von Liebig able to find answers to these questions.

Until 1914, the method for producing acetone was the coking process of wood. But during the First World War, the demand for acetone greatly increased, as it began to act as a vital component in the production of smokeless gunpowder. It was this fact that served as the impetus for the creation of more elegant methods for producing this compound. It’s hard to believe, but they began to produce acetone from corn, and the discovery of this method in support of military needs belongs to Chaim Weizmann, a chemist from Israel.

Application of acetone

We have established the “official” name, some physical properties and formula of acetone, the production of which in the world is about 7 million tons per year (and these are data for 2013, and production volumes are only growing). But what can be said about its role in the life of humanity?

As mentioned above, this substance is a volatile liquid, which greatly complicates its use in production. What use are we talking about? The fact is that acetone is used as a solvent for many substances. However, its increased volatility often prevents it from being used in its pure form, for which purpose the composition of this solvent is deliberately changed in production.

In the food industry, acetone plays an important role because it is not so toxic (unlike most other solvents). Everyone has at least once encountered a banal nail polish remover based on acetone (even though modern society is trying to eradicate it from its composition). Acetone is also often used to degrease various surfaces. It is also important to note that this substance is widely used in pharmaceutical syntheses, in the syntheses of epoxy resins, polycarbonates and even explosives!

How dangerous is acetone for humans?

Words have been heard more than once about the mild toxicity of the substance of interest to us. It’s worth saying more specifically about the danger that such a harmless, at first glance, formula of acetone poses to humans.

This substance is classified as flammable and hazard class 4 substances, that is, low-toxic.

The consequences of acetone getting into the eyes are extremely serious - this is either a severe decrease in vision or its complete loss, since acetone causes a severe chemical burn to the mucous membrane, and healing leaves a scar on the retina. Immediately flushing your eyes with plenty of clean water will help reduce some of the damage to your vision.

Ingestion of acetone into the body orally causes the following consequences: loss of consciousness after a few minutes, periodic stoppages of breathing, possible decrease in blood pressure, nausea and vomiting, abdominal pain, swelling of the mucous membranes of the mouth, esophagus and stomach, shortness of breath, rapid heartbeat, as well as hallucinations.

Inhalation poisoning with gaseous acetone manifests itself almost similarly to that described above. The obvious difference is swelling of the airways rather than the digestive tract. The eyes may also become swollen when exposed to ambient gases.

Skin burns from contact with acetone are most often not observed, which is due to the high volatility of the substance. However, there are still known cases of 1st and 2nd degree burns.

An interesting acetone derivative: meet acetoxime

In addition to the properties and formula of acetone as such, it is worth taking a closer look at its closest “relatives”. For example, let's get acquainted with a substance such as acetoxime.

Acetoxime is a derivative of acetone. The formula of acetone oxime is not much more complicated than the formula of propanone-2, which is so familiar to us: C 3 H 7 NO. The spatial structure is shown in the figure below.

One of the possible ways to obtain acetoxime is by reacting acetone with hydroxylamine.

Application of oximes

Speaking about such a class of organic compounds as oximes, it is necessary to note the scope of their use in the modern world. Oximes themselves are solids, but fusible, that is, with low melting points.

Different oximes have accordingly different uses. Thus, some of them are necessary in the production of caprolactam, others are used in analytical chemistry, where they help in the detection and quantification of nickel (since the result of the interaction is a red substance).

A separate class of oximes is used as a medicine for poisoning with organophosphate compounds.