What are harmful phenol. Phenol: properties and production technology. Why is phenol dangerous?

Largest Quantities phenols are used to produce phenol-formaldehyde resins, which are used in the production of phenolic plastics. Large quantities of phenol are processed into cyclohexanol, which is essential for the synthetic fiber industry. A mixture of cresols is used to produce cresol-formaldehyde resins. Pure cresols are used for the synthesis of dyes, medicines, antiseptics, and antioxidants.

Application in medicine:

With the introduction of a large dose of phenol into the stomach, the latter was found in the contents of the stomach, in the blood, in the liver, kidneys, spleen, muscles and urine. Undesirable side effects can develop even after medical doses of phenol, namely, mild headache, sometimes - dizziness, a feeling of intoxication or deafness, a feeling of crawling, increased sweating and general fatigue. But when ingested in large quantities, the signs of poisoning are characterized by: severe headache, dizziness, fainting, tinnitus, pallor, nausea, vomiting, loss of strength, abnormal breathing and a small pulse; urine in mild cases of poisoning, as well as after medical doses taken for a long time, is colored dark, which depends on the transition of a significant amount of phenol introduced into the body into hydroquinone, which, upon further oxidation, gives colored compounds. Severe cases of poisoning are characterized by unconsciousness, cyanosis, shortness of breath, corneal insensitivity, fast, barely perceptible pulse, cold sweat, low temperature, and often convulsions. If, after the introduction of phenol through the mouth, vomiting appears, then the vomit has the smell of phenol; urination in most cases is upset, urine contains protein, in rare cases there is a blood pigment in the urine - the so-called hemoglobinuria is observed. In rare cases, after such symptoms, a fairly rapid recovery of strength was observed, but in the vast majority of cases, despite the return of consciousness from time to time, death occurs very quickly due to difficulty in breathing and an extreme decline in cardiac activity. The mucosal burns produced by phenol rarely penetrate the muscular layer of the latter, and usually they do not occur below the duodenum; sometimes they found limited and diffuse bruises in the first ways of the digestive canal, in other cases the mucous membrane acquired a firmer consistency, resembling tanned skin. The stomach contains brown clotted blood, the intestines are covered with blood mucus; pulmonary edema was often observed; in the kidneys, hyperemia, swelling of the cortex, blood blockages in the cortex and fatty degeneration of the renal epithelium are found. The possibility of fatal phenol poisoning following topical application of large amounts to intact skin has been proven both by human observations and experimental studies on animals. A case of death is described after lubricating the skin against scabies with a concentrated solution of phenol. By the end of rubbing, there was a burning sensation in the skin, a feeling of dizziness and severe deafness, delirium and complete loss of consciousness, after which death soon followed. As an antidote for poisoning with phenol administered orally, based on experiments on animals, caustic lime with sugar was proposed (5 hours of caustic lime are dissolved in 40 hours of water, 60 hours of cane sugar are added to the solution, then the mixture is filtered and evaporated to dryness at a temperature .100°). The combination of lime with phenol is sparingly soluble and therefore slightly toxic. The drug should be prescribed in the first minutes after poisoning, since phenol is very quickly absorbed from the stomach. Among the antidotes, mention should be made of lime water, lime carbonate, and crushed chalk. In addition, useful: gastric lavage, stimulants, and especially useful to warm the patient.

Phenol, extracted by Runge from coal tar in 1834, was already known at that time as an anti-putrefactive agent, but this agent was widely used in medicine only from the end of the 1860s. of the last century, when the famous English surgeon Lister used phenol to treat wounds and for the doctrine of antiseptics he created.

Pharmachologic effect. Solutions of carbolic acid (3-5%) cause the clotting of the dissolved protein; phenol has the same effect on the glue solution, on milk, albumin and casein of which coagulate from a 5% phenol solution. With putrefactive proteins, carbolic acid seems to form a strong chemical bond, since it cannot be opened in coagulated liquid unless it has been added in excess. Red blood globules with direct action on them of 3-4% phenol solutions gradually wrinkle, the coloring matter is separated from the stroma; the drug has the same destructive effect on purulent balls, on muscle and nerve fibers. It has been proven that 1-2% phenol solutions destroy mold fungi; solutions 1:500 stop the development of fungi; 1-2% solutions reduce the ability of yeast cells to ferment grape or milk sugar, stronger solutions (4-5%) completely destroy the vital activity of these cells. Bacteria that cause putrefaction of organic matter are not so easily influenced by phenol; this requires the action of more concentrated solutions and a longer action; so a solution of 1:200 only delays the development of putrefactive microorganisms, to destroy the ability to reproduce the latter, concentrations of 1:25 are required. 1% solutions (according to Koch) do not act on anthrax spores even for 15 days; 2% retard development in about 10-20 hours; 3% cause, after 3 days, free gaps in breeding, but spores are killed after 7 days; A 4% solution gives the same effect on the third, and 5% on the second day (note that carbolic acid in an alcoholic or oily solution does not even have a weak antiseptic effect when microorganisms are outside the body or on artificial nutrient media) . Erysipelatous cocci resist the action of 1% phenol solution for only 60 seconds; diphtheritic sticks detect a decrease in growth after 30 seconds; yellow pyogenic grapevine resists the 5-minute action of 1% and the 15-second action of the 2nd solution; the microorganisms of typhus and cerebrospinal meningitis turned out to be more resistant; glanders sticks, chain coccus of puerperal fever were destroyed by 3% carbolic solution in 15-60 seconds. Carbolic acid acts on unorganized enzymes to a much lesser extent: the addition of phenol in 1/2% of the mixture of saliva and sugar does not affect the physiological properties of saliva. The conversion of protein into peptones under the influence of digestive juice, apparently, is delayed and even completely stopped by the action of a 1/2% or stronger solution, which is explained by changes in the physical properties of the protein, namely, coagulation and difficulty in converting it into acidalbumin. The formation of hydrocyanic acid under the action of emulsin on amygdalin is only temporarily stopped by a 4% solution, reappearing after dilution of the phenol solution.

Therapeutic application. Lubrication with concentrated solutions causes whitening of the skin, a feeling of pain; the white spot consists of a highly unstable combination of carbolic acid with the tissue of the upper skin; areas of the skin become after lubrication 3-5 percent. solutions, due to impregnation of sensitive, insensitive endings with carbolic acid, they experience a feeling of numbness for several hours. Based on these properties of carbolic acid, its external use in weak solutions as an analgesic and in concentrated solutions as a cauterizing and destructive substance is based. Due to its anti-putrefactive properties, phenol is widely used for disinfecting objects and premises in which harmful bacteria can remain after infectious patients, as well as for the anti-putrefactive method of treating wounds; for the same purpose, dressings (gauze, cotton wool, yuta, etc.) are still impregnated with phenol solutions, although they are now trying to replace the "anti-putrefactive" method with a "putrefactive", i.e., a method in which microorganisms are not allowed to enter the wound , as this gives the best results. In case of burns, lubrication with a 1-2% solution of phenol has an antiseptic effect, relieves pain and limits the separation of the ulcerative surface; local anesthesia when using alcohol or ether solutions is more pronounced than from oil or glycerin solutions. Inside, phenol is prescribed, usually in pills, 0.02-0.04 several times a day, against abnormal processes of fermentation or putrefaction in the stomach or intestines, then also for the same processes in the respiratory organs, and inhalations have proven useful in such diseases. 1-2% solution of phenol, but the appointment inside gives some improvement in putrefactive bronchitis, with gangrene of the lungs. Undoubtedly, the use of phenol for the disinfection of departments and secretions of the patient, his linen, dwelling, etc. % phenol).

The use of phenols. A solution of phenol is used as a disinfectant (carbolic acid). Dihydric phenols - pyrocatechin, resorcinol (Fig. 3), as well as hydroquinone (para-dihydroxybenzene) are used as antiseptics), tibacterial disinfectants), are introduced into tanning agents for leather and fur, as stabilizers for lubricating oils and rubber, as well as for processing photographic materials and as reagents in analytical chemistry.

In the form of individual compounds, phenols are used to a limited extent, but their various derivatives are widely used. Phenols serve as starting compounds for obtaining a variety of polymer products - phenolic resins (Fig. 7), polyamides, polyepoxides. Based on phenols, numerous drugs are obtained, for example, aspirin, salol, phenolphthalein, in addition, dyes, perfumes, plasticizers for polymers and plant protection products.

Lysol is used to disinfect the skin. Resorcinol is used for skin diseases (eczema, seborrhea, itching, fungal diseases) externally in the form of solutions (water and alcohol) and ointments. Benzonaphthol, an antiseptic for diseases of the gastrointestinal tract. Adults appoint 0.3-0.5 g 3-4 times a day. Children under 1 year old - 0.05 g per dose, up to 2 years old - 0.1 g, 3-4 years old - 0.15 g, 5-6 years old - 0.2 g, 7 years old - 0.25 g, 8 -14 years - 0.3 g.

CONCLUSION: Phenol compounds are very diverse, phenol and its compounds are widely used in industry and medicine.

Phenol - what it is, what effect it has on the body, what the symptoms of poisoning with this substance and its consequences can be - every person living in an urban environment needs to know about this.

There is a strong opinion that phenol compounds are a product chemical industries and they are bad for environment and living organisms. This is only partly true, since phenol is found in many foods, is part of plants and one of the elements constantly present in the human body.

What it is?

Phenol is a hydrocarbon of organic origin, also known as hydroxybenzene and carbolic acid.

The effect of phenol on the human body depends on the type of substance - compounds produced by synthesis are dangerous, their evaporation is especially harmful, and natural phenol, on the contrary, is useful.

Outside of industrial laboratories, this substance is found:

In nuts.
in cocoa beans.
In all fruits and berries.
In olive and other vegetable oils.

Natural phenol is an antioxidant and preservative that protects plants and fruits from harmful insects, diseases and ensures their safety.

Artificial phenols have the following properties that characterize them:

Completely soluble in water and alcohols, with a large amount they give the liquid a faint smell of gouache paint.
It begins to evaporate already when heated to 40-42 degrees.

Due to this, phenol poisoning can be completely accidental, not even suspecting contact with its vapors or itself, dissolved in water or alcoholic beverages.

Where is phenol used?

Chemical compounds of phenol, the poisoning of which, as a rule, occurs, are used in the manufacture of:

Medicines.
cosmetics.
A range of litmus liquids used in laboratory medical tests.
In the production of plastic packaging and plastics.
In the paint and varnish and oil refining industries.
in the production of fertilizers.
In the manufacture of automotive oils, glass cleaners and other technical fluids.
In veterinary medicine - for the treatment of the skin of animals.
In the production of household chemicals.

The list of uses of phenols is quite voluminous, and encounter in Everyday life with the poisoning effect of this substance on the body is quite easy. For example, the cause of phenol poisoning can be a simple skin cream, forgotten on the windowsill and lying for some time in direct sunlight, which heated the flask to 40 degrees and above.

What happens in case of poisoning?

An artificially obtained substance has a second hazard class, which means high toxicity and danger to both living organisms and the environment. According to environmentalists, the period of full recovery natural area after a phenol leak is from 25 to 35 years, not taking into account the poisoning of animals, the consequences of which are almost impossible to calculate.

People are most often poisoned by the vapors of this substance, and this usually occurs due to improper storage or use of products containing phenol, improper handling of plastic items and their use for other purposes.

For example, heating food in a microwave oven in a plastic container that is not intended for this, that is, does not have the appropriate labeling, can cause mild poisoning, which can be mistaken for food intoxication.

When ingested, phenol has the following effects:

The mucous membranes are affected, especially the mucous membranes of the eyes, respiratory tract, nasopharynx and esophagus - when toxic fumes are inhaled.
Severe chemical burns - if phenolic acids come into contact with the skin, for example, when working with pesticides or technical oils.
Necrosis of muscle tissue and blood clotting - when ingested with drinks or food.

Regardless of how exactly the toxin entered the body - by inhaling vapors or together with products, the consequences of its toxic effect are:

The destruction of red blood cells and the breakdown of the integrity of the blood composition, which leads to oxygen starvation.
The emergence and rapid development of pyelonephritis.
Death of liver cells.
Allergic edema of the respiratory tract and dermatitis.
Violation of brain activity, the breakdown of protein cells in the brain.
Dysfunction of neural processes, that is, the cessation of the normal functioning of the nervous system.

Intoxication by inhalation, that is, poisoning with vapors of phenol and its compounds, occurs already when the content of the toxic substance in the air is at a concentration of 0.01 mg / m³, and the lethal dosage for an adult is the ingestion of 8-10 grams of the toxin, for a child it takes less - 5 to 7 grams of phenol.

How to distinguish poisoning?

Unlike food intoxication, phenol poisoning begins to manifest itself not in the form of nausea, but in the form of brain phenomena and disturbances in nervous activity.

Intoxication with this poison is accompanied by such signs of poisoning:

Sudden psycho-emotional arousal, turning into uncontrollable irritation, which is replaced by complete apathy for everything around.
There is a loss of strength, general muscle weakness, a desire to rest, there is a feeling of severe physical fatigue.
Tactile sensations decrease, against the background of aggravated reactions to light and sound.
Dizziness appears, sometimes accompanied by a loss of coordination in space and time.
There is a headache, with a concentration in the occipital region, against which drugs do not help.
Motility is impaired, spontaneous convulsions may occur.
The skin turns pale, covered with goosebumps, the person becomes cold.
There is shortness of breath, which is accompanied by the urge to sneeze and spasmodic cough.
With local contact with phenol, for example, when playing with a toy colored with a dye containing it, a skin rash develops, of a beet-cyanotic hue.

With constant contact with the toxin, chronic phenol poisoning develops, hallmark which is not passing physical fatigue, along with irritability, headaches and fatigue.

What do we have to do?

Treatment of intoxication requires medical intervention, it is impossible to cope with such poisoning on your own and it is impossible to prevent its consequences.

Having noticed the symptoms of phenol intoxication, you should immediately call the doctors, and while the doctors are on their way, provide first aid to the victim.

The specificity of first aid is that, first of all, it is necessary to isolate a source that is harmful to health, that is:

Remove the person to fresh air if the harm is caused by phenol vapors concentrated in the room.
If the toxin gets on the skin, the affected area should be washed with soap and water.
It is necessary to change the victim's clothing, since phenolic fumes tend to accumulate in the tissues.
It is necessary to rinse the eyes with plenty of running water, since particles hazardous to health settle on the mucous membranes, and you should also wash your face.
If phenol enters the body with water, drinks or food, sorbents should be taken.

Among the sorbent preparations for first aid in case of poisoning of the human body with phenolic compounds, the following are most effective:

Carbolene;
Enterosorb;
Sorbex;

Of course, these drugs cannot neutralize the harm, but they help to reduce the pathogenic activity of the toxin. It is also useful to restore health to take activated charcoal. It acts not only on the digestive system, but also on the blood.

Most often, poisoning is not in pairs, but by contact, occurs in children, poor-quality toys are to blame for this. The first help in such a situation would be washing the area of the skin that has come into contact with the toxin with soap, rinsing the mouth with water and taking coal in the proportion of 1 washer per 5 kg of weight.

Pre-medical home treatment of this type of poisoning excludes gastric lavage, even if it is certain that the poison entered the body along with drinks or food. Phenol has a different density than gastric juice or foods and liquids in the stomach, so when inducing vomiting, it can burn the mucosa of the esophagus.

Video: film about phenol.

What will the doctors do?

Treatment of intoxication with this substance involves the use of its antidote - calcium gluconate. The introduction of this solution is carried out only intravenously, and the dosage is determined based on the weight, age of the victim and the severity of the poisoning itself.

Children usually do not tolerate injections with a solution, so they are often replaced with injections for drip injections.

In addition to using an antidote, treatment for this poisoning includes the following procedures:

General detoxification therapy, this treatment is not so much aimed at destroying the toxin, but rather at cleansing the blood, kidney and liver tissues and restoring the balance of red blood cells.
Hemosorption, this treatment consists in cleaning the blood in a medical device, it is similar to a transfusion and quite painful, such a medical action is used when it is impossible to bind and remove poison molecules from the blood in another way.
Hemodialysis, that is, "artificial kidneys", is used if there is a failure of the kidneys, there is a potential for their dysfunction, or for other medical reasons.

People can experience symptoms of intoxication with this substance, without encountering either its vapors or household chemicals, of which it is included, even without using plastic and plastic items and cosmetics. This happens due to the consumption of meat, eggs, milk or cottage cheese that have not passed sanitary checks.

Poisoning of animals with phenol derivatives happens quite often, since this substance is part of pesticides, fertilizers and a number of drugs used by veterinarians and livestock specialists to treat livestock and poultry.

To avoid the risk of such intoxication, you should buy only those livestock products that have sanitary certificates, this is especially important when purchasing them at markets and farmers' fairs.

Of course, phenol is a poison. Therefore, it is used as a preservative so that the infection does not multiply.

Phenol kills microbes, which is why it is introduced into vaccines so that they do not settle there.

Phenol is also used in cosmetics, creams, shampoos. Phenol and its derivatives easily penetrate the human body through the skin

Even such appetizing green apples do not spoil for a long time precisely because they are treated with phenol. Wash the apples thoroughly, but rather cut off the peel. Of course, this applies to other fruits as well.

Very, very many foods contain phenol.

Phenol is also found in building materials,

in any where synthetic or plastic adhesives are used: in chipboard, fiberboard, OSB, in plywood, in heat-insulating plates, in linoleum, in laminate, a little in vinyl wallpaper, in stretch ceilings, in the plastic that is on the windows, in panels PVC, in almost all of our kitchen oilcloths, etc., we live in the age of chemistry, we can’t do without it. And insofar as our furniture is made of sawdust mixed with glue, that is, made of fiberboard, chipboard, MDF boards, there is also enough of it in furniture, often even more than in building materials.

Phenol vapors are poisonous. They have a specific smell (such as the smell of gouache, because gouache contains phenol).

Question - and how much phenol evaporates from building materials? I can't stand the smell of fresh building materials.

Some nasal and ear drops contain phenol.

Even in the human body, phenol is formed during metabolism and excreted in the urine. The mechanism is not clear to me.
Some microorganisms living in the intestine produce phenol.

It is clear that all poison and all medicine and is dose dependent. Limit concentrations have not been canceled.

Once again, the child does not want to introduce phenol. You always need to evaluate the benefit-harm ratio.

For example, Mantoux, diaskintest, containing phenol, identify patients with tuberculosis. You can also do PCR. This is blood or saliva taken for analysis.
In theory, probably better to do PCR. At least no byaka is injected into the body. I don’t know just how informative it is, and whether it is accepted as a replacement for Mantoux. I found about PCR

Order No. 64 dated February 21, 2000 "On approval of the nomenclature of clinical laboratory research"It is very clearly stated there that the Ministry of Health of the Russian Federation recommends PCR as an alternative method of testing for tuberculosis, clause 9.4.5 of the appendix. The high efficiency of this method is also prescribed there.
Polymerase chain reaction(PCR), based on the detection of a DNA segment characteristic only for a given pathogen, can serve as one of the methods for express diagnosis of tuberculosis. The high sensitivity of PCR makes it possible to detect single cells or even fragments of pathogen DNA in the test material within 4-5 hours. PCR enables differential diagnosis in limited forms of tuberculosis (focal infiltrates, tuberculomas, tuberculosis of the intrathoracic lymph nodes), as well as in the disseminated form of tuberculosis, in which differential diagnosis using only traditional microbiological methods is very difficult due to the rare detection of the pathogen in sputum. Summarizing the results of bacterioscopy, inoculation on solid nutrient media and PCR studies of material obtained from patients with limited forms of tuberculosis, we can conclude that the latter has a significantly higher sensitivity compared to traditional methods. PCR is highly informative when it is necessary to confirm the diagnosis of tuberculosis in children and adolescents with negative results of traditional microbiological research methods. The use of PCR in the diagnosis of tuberculosis is recommended by the Ministry of Health of the Russian Federation (order No. 64 of February 21, 2000 "On approval of the nomenclature of clinical laboratory tests", clause 9.4.5. of the appendix).
http://www.mamakazan.ru/forum/viewtopic.php?f=80&t=15006
Although it is possible that no one will give a 100% guarantee of the absence of the disease.
I don't want to do more manta. A 10-year-old boy has a constantly positive reaction. In the TB dispensary, they diagnosed an allergy, but they did not stop doing Mantoux. No information content. And I'm worried. Must at least general analysis ask for blood. Still, it will show whether there is inflammation or not.
In general, I wonder why not first do a general blood test for everyone to find out if there is inflammation. For example, with tuberculosis, an increased content of monocytes in the blood.
Of course, an increase in monocytes can also be with other diseases, then it can be diagnosed by other methods (diaskin test, Mantoux, PCR)

Hydroxybenzene

Chemical properties

What is Phenol? Hydroxybenzene, what is it? According to Wikipedia, this is one of the simplest representatives of its class of aromatic compounds. Phenols are organic aromatic compounds in the molecules of which carbon atoms from the aromatic ring are attached to the hydroxyl group. General formula Phenols: C6H6n(OH)n. According to the standard nomenclature, organic matter of this series are distinguished by the number of aromatic nuclei and HE- groups. There are monohydric arenols and homologues, dihydric arendiols, terchatomic arentriols and polyhydric formulas. Phenols also tend to have a number of spatial isomers. For example, 1,2-dihydroxybenzene (pyrocatechin ), 1,4-dihydroxybenzene (hydroquinone ) are isomers.

Alcohols and phenols differ from each other by the presence of an aromatic ring. ethanol is a homologue of methanol. Unlike phenol, methanol interacts with aldehydes and enters into esterification reactions. The statement that methanol and Phenol are homologues is incorrect.

It is to consider in detail the structural formula of Phenol, it can be noted that the molecule is a dipole. In this case, the benzene ring is the negative end, and the group HE- positive. The presence of a hydroxyl group causes an increase in the electron density in the ring. The lone pair of oxygen electrons enters into conjugation with the pi system of the ring, and the oxygen atom is characterized by sp2 hybridization. Atoms and atomic groups in a molecule have a strong mutual influence on each other, and this is reflected in the physical and chemical properties of substances.

Physical Properties. The chemical compound has the form of colorless needle-shaped crystals that turn pink in air, as they are subject to oxidation. The substance has a specific chemical smell, it is moderately soluble in water, alcohols, alkali, acetone and benzene. Molar mass = 94.1 grams per mole. Density = 1.07 g per liter. Crystals melt at 40-41 degrees Celsius.

What does Phenol interact with? Chemical properties of Phenol. Due to the fact that the compound molecule contains both an aromatic ring and a hydroxyl group, it exhibits some properties of alcohols and aromatic hydrocarbons.

How does the group react? HE? The substance does not show strong acid properties. But it is a more active oxidizing agent than alcohols, unlike ethanol, it interacts with alkalis forming phenolate salts. Reaction with sodium hydroxide :C6H5OH + NaOH → C6H5ONa + H2O. The substance reacts with sodium (metal): 2C6H5OH + 2Na → 2C6H5ONa + H2.

Phenol does not react with carboxylic acids. Esters are obtained by reacting salts of phenolates with acid halides or anhydrides. For a chemical compound, formation reactions are not characteristic ethers. Esters form phenolates under the action of haloalkanes or halogen derivatives of arenes. Hydroxybenzene reacts with zinc dust, while the hydroxyl group is replaced by H, the reaction equation looks like this: C6H5OH + Zn → C6H6 + ZnO.

Chemical interaction along the aromatic ring. The substance is characterized by reactions of electrophilic substitution, alkylation, halogenation, acylation, nitration and sulfonation. Of particular importance is the reactions of the synthesis of salicylic acid: C6H5OH + CO2 → C6H4OH(COONa), proceeds in the presence of a catalyst sodium hydroxide . Then, upon exposure, it is formed.

Interaction reaction with bromine water is a qualitative reaction to Phenol. C6H5OH + 3Br2 → C6H2Br2OH + 3HBr. Bromination produces a white solid 2,4,6-tribromophenol . Another qualitative response ferric chloride 3 . The reaction equation looks like this: 6C6H5OH + FeCl3 → (Fe(C6H5OH)6)Cl3.

Phenol nitration reaction: C6H5OH + 3HNO3 → C6H2(NO2)3OH + 3H2O. The substance is also characterized by an addition reaction (hydrogenation) in the presence of metal catalysts, platinum, aluminum oxide, chromium, and so on. As a result, cyclohexanol And cyclohexanone .

The chemical compound undergoes oxidation. The stability of the substance is much lower than that of benzene. Depending on the reaction conditions and the nature of the oxidizing agent, different reaction products are formed. Under the action of hydrogen peroxide in the presence of iron, diatomic Phenol is formed; under action manganese dioxide , chromium mixture in an acidified medium - para-quinone.

Phenol reacts with oxygen, combustion reaction: С6Н5ОН + 7О2 → 6СО2 + 3Н2О. Also of particular importance for industry is the reaction of polycondensation with formaldehyde (For example, metanalem ). The substance enters into a polycondensation reaction until one of the reactants is completely consumed and huge macromolecules are formed. As a result, solid polymers are formed, phenol-formaldehyde or formaldehyde resins . Phenol does not interact with methane.

Receipt. On this moment Several methods for the synthesis of hydroxybenzene exist and are actively used. The cumene method for obtaining Phenol is the most common of them. About 95% of the total production of the substance is synthesized in this way. In this case, non-catalytic oxidation by air undergoes cumene and formed cumene hydroperoxide . The resulting compound is decomposed by sulfuric acid on acetone and Phenol. An additional by-product of the reaction is alpha-methylstyrene .

Also, the compound can be obtained by oxidation toluene , the reaction intermediate will be benzoic acid . Thus, about 5% of the substance is synthesized. All other raw materials for various needs are isolated from coal tar.

How to get from benzene? Phenol can be obtained using the direct oxidation reaction of benzene NO2() with further acid decomposition sec-butylbenzene hydroperoxide . How to get phenol from chlorobenzene? There are two options for getting chlorobenzene this chemical compound. The first is the reaction of interaction with alkali, for example, with sodium hydroxide . As a result, phenol and table salt are formed. The second is the reaction with water vapor. The reaction equation looks like this: C6H5-Cl + H2O → C6H5-OH + HCl.

Receipt benzene from Phenol. To do this, you first need to treat benzene with chlorine (in the presence of a catalyst), and then add an alkali to the resulting compound (for example, NaOH). As a result, Phenol is formed and.

transformation methane - acetylene - benzene - chlorobenzene can be done as follows. First, the methane decomposition reaction is carried out at a high temperature of 1500 degrees Celsius to acetylene (C2H2) and hydrogen. Then acetylene, under special conditions and high temperature, is converted into benzene . Chlorine is added to benzene in the presence of a catalyst FeCl3, get chlorobenzene and hydrochloric acid: C6H6 + Cl2 → C6H5Cl + HCl.

One of the structural derivatives of Phenol is an amino acid that is of great biological importance. This amino acid can be considered as para-substituted Phenol or alpha-substituted para-cresol . Cresols - quite common in nature along with polyphenols. Also, the free form of a substance can be found in some microorganisms in an equilibrium state with tyrosine .

Hydroxybenzene is used:

in production bisphenol A , epoxy resin and polycarbonate ;
for the synthesis of phenol-formaldehyde resins, capron, nylon;
in the oil refining industry, in the selective purification of oils from aromatic sulfur compounds and resins;
in the production of antioxidants, surfactants, cresols , lek. drugs, pesticides and antiseptics;
in medicine as an antiseptic and anesthetic for topical use;
as a preservative in the manufacture of vaccines and smoked foods, in cosmetology during deep peeling;
for disinfection of animals in cattle breeding.

Hazard Class. Phenol is an extremely toxic, poisonous, caustic substance. When a volatile compound is inhaled, the work of the central nervous system is disrupted, the vapors irritate the mucous membranes of the eyes, skin, Airways and cause severe chemical burns. Upon contact with the skin, the substance is rapidly absorbed into the bloodstream and reaches the brain tissue, causing paralysis of the respiratory center. The lethal dose by ingestion for an adult is 1 to 10 grams.

pharmachologic effect

Antiseptic, cauterizing.

Pharmacodynamics and pharmacokinetics

The agent exhibits bactericidal activity against aerobic bacteria, their vegetative forms and fungi. Virtually no effect on fungal spores. The substance interacts with protein molecules of microbes and leads to their denaturation. Thus, the colloidal state of the cell is disturbed, its permeability is significantly increased, redox reactions are disturbed.

In an aqueous solution, it is an excellent disinfectant. When using a 1.25% solution, almost microorganisms die within 5-10 minutes. Phenol, in a certain concentration, has a cauterizing and irritating effect on the mucous membrane. The bactericidal effect of the use of the product increases with increasing temperature and acidity.

Upon contact with the surface of the skin, even if it is not damaged, the drug is rapidly absorbed, penetrates into the systemic circulation. With systemic absorption of a substance, its toxic effect is observed, mainly on the central nervous system and the respiratory center in the brain. About 20% of the dose taken undergoes oxidation, the substance and its metabolic products are excreted by the kidneys.

Indications for use

Application of Phenol:

for disinfection of tools and linen and disinfestation;
as a preservative in some lek. products, vaccines, suppositories and serums;
at superficial, conflict , osteofolliculitis , sykose , streptococcal impetigo ;
for the treatment of inflammatory diseases of the middle ear, oral cavity and pharynx, periodontitis , genital spiky warts .

Contraindications

The substance is not used:

with widespread lesions of the mucous membrane or skin;
for the treatment of children;
during breastfeeding and;
when on Phenol.

Side effects

Sometimes the drug can provoke the development of allergic reactions, itching, irritation at the site of application and a burning sensation.

Instructions for use (Method and dosage)

Preservation of drugs, sera and vaccines is carried out using 0.5% solutions of Phenol.

For external use, the drug is used in the form of an ointment. The drug is applied in a thin layer to the affected areas of the skin several times a day.

In the treatment, the substance is used in the form of a 5% solution in. The drug is heated and instilled 10 drops into the affected ear for 10 minutes. Then you need to remove the remnants of the medicine with cotton wool. The procedure is repeated 2 times a day for 4 days.

Phenol preparations for the treatment of ENT diseases are used in accordance with the recommendations in the instructions. Duration of therapy - no more than 5 days.

To eliminate spiky warts they are treated with a 60% Phenol solution or a 40% solution tricresol . The procedure is carried out once every 7 days.

When disinfecting linen, 1-2% soap-based solutions are used. With the help of a soap-phenolic solution, the room is treated. When disinsection, phenol-turpentine and kerosene mixtures are used.

Overdose

When the substance gets on the skin, burning, redness of the skin, anesthesia of the affected area occur. The surface is treated with vegetable oil or shock .

Interaction

There is no drug interaction.

special instructions

Phenol has the ability to be adsorbed by food products.

The product should not treat large areas of the skin.

Before using the substance for disinfection of household items, they must be mechanically cleaned, as the agent is absorbed by organic compounds. After processing, things can retain a specific smell for a long time.

The chemical compound must not be used to treat premises for the storage and preparation of food products. It does not affect the color and structure of the fabric. Damages varnished surfaces.

children

The tool can not be used in pediatric practice.

During pregnancy and lactation

Phenol is not prescribed during breastfeeding and during pregnancy .

Preparations containing (Analogues)

Coincidence in the ATX code of the 4th level:

Phenol is part of the following drugs:, Phenol solution in glycerin , Pharmaseptic . As a preservative, it is contained in preparations: Belladonna extract , Skin Diagnosis Kit for Drug Allergy , and so on.

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Abstract on

ORGANIC CHEMISTRY

TOPIC: "Phenol in medicine and pharmacy»

Introduction

1.1 Physical properties

1.2 Impact on the human body

1.3 Application in medicine and pharmacy

2. Resorcinol

2.1 Physical properties

2.2 Effects on the human body

2.3 Application in medicine and pharmacy

3. Pyrocatechin

3.1 Physical properties

3.2 Effects on the human body

3.3 Application in medicine and pharmacy

4. Hydroquinone

4.1 Physical properties

4.2 Effects on the human body

4.3 Application in medicine and pharmacy

5. Phloroglucinol

5.1 Physical properties

5.2 Medical and pharmaceutical applications

Introduction

Phenols are organic substances whose molecules contain a phenyl radical associated with one or more hydroxyl groups.

Phenols - colorless crystalline substances with a low melting point and a characteristic odor. Phenols are slightly soluble in cold water, readily soluble in organic solvents, toxic, gradually darken when stored in air as a result of oxidation.

1. Phenol

1.1 Physical properties of phenol

1) Molecular formula: C 6 H 6 O;

2) Relative molecular weight: 94.11 a. eat.;

3) Melting point: 40.5°C;

4) Boiling point: 181.7 °C;

5) Density: 1.07 g/cm3.

Phenol - Chemical substance organic origin, belongs to the group of aromatic hydrocarbons.

Phenol is a colorless crystalline mass. Under the influence of air gradually acquires a pink tint. Easily soluble in water, ether, alcohol and fatty oils.

Phenol is poisonous. Dust and phenol solution irritate the mucous membranes of the eyes, respiratory tract, and skin. Possesses slightly acidic properties, under the action of alkalis forms salts - phenolates. Under the action of bromine, tribromophenol is formed, which is used to obtain an antiseptic - xeroform. The benzene nucleus and the OH group combined in the phenol molecule affect each other, significantly increasing the reactivity of each other. Of particular importance are the condensation reactions of phenols with aldehydes and ketones, as a result of which polymer products are obtained.

1.2

Phenol causes irreparable damage to the health of many vital human organs. Once inside through the respiratory tract, it irritates the nasopharynx, leaves burns that can develop into pulmonary edema.

If a phenol solution accidentally gets on the skin, chemical burns instantly form on it, then ulcers. A phenolic burn of 25% of the body area is likely to be fatal. The intake of this toxic compound into the body through the gastrointestinal tract (with water) makes it difficult to move, threatens with bleeding, muscle atrophy, peptic ulcer. Despite the fact that phenol is excreted from the body rather quickly (in 24 hours), it manages to significantly damage health and leave consequences for many years.

Among the most serious consequences of phenol intoxication are infertility, heart failure and cancer.

1.3

Among the antiseptic agents widely used in modern medicine, phenol occupies a significant place. Its solutions have a good bactericidal effect against microorganisms (vegetative form) and fungi. They have little effect on spores of microorganisms. Interacting with the protein of microorganism cells, phenol causes its denaturation, increases the permeability of cell membranes, and affects the oxidative processes in the cell. The bactericidal effect increases with increasing temperature and in an acidic environment.

Most often, this substance is used in the form of a 3-5% solution for disinfecting various surfaces. Phenol can be used at home to disinfect objects, things, floors. Lacquered furniture should not be treated with this substance. In medical institutions, it is used to process hospital items, linen, and tools. The use of phenol in the form of a soap-carbolic solution makes it possible to process large areas of public premises. Phenol-turpentine, phenol-kerosene and other mixtures are also often used.

It is widely used in pharmaceutical practice. So 0.5-0.1% phenol is used to preserve suppositories, medicines, serums and other preparations. The use of phenol in medicine is possible with some serious skin diseases (ostiofolliculitis, sycosis, folliculitis, streptococcal impetigo), with genital warts and acute inflammation of the middle ear. Phenol has a cauterizing and irritating effect on the mucous membranes and skin. The drug is easily absorbed and in high doses can cause such toxic effects as weakness, dizziness, collapse, respiratory disorders. It should not be used for common diseases of the mucous membranes and skin. When using this substance, one should not forget that it is easily adsorbed with all food products.

The use of phenol is also possible in the following forms:

a) Pure liquid phenol, consisting of a mixture of 100 parts of molten carboxylic acid and 10 parts of water. It is a pinkish or colorless oily liquid;

b) 3 and 5% solution of carboxylic acid in glycerin;

c) 2% phenol ointment;

d) Solution "Fukortsin", containing 0.8 parts of boric acid; 3.9 parts of pure phenol; 7.8 parts resorcinol; 0.4 parts fuchsin; 4.9 parts of acetone; 9.6 parts 95% ethyl alcohol; and distilled water (in an amount that brings it to 100 parts). This disinfectant liquid is red in color and smells like phenol. Used as an antifungal and antiseptic agent. Is issued in bottles with dark glass on 25 ml.;

e) The preparation "Ferezol" is a homogeneous mixture, which includes phenol (60%) and tricresol (40%). This brown oily liquid with a phenolic odor has a bactericidal and cauterizing effect. It is used to remove warts, papillomas, genital warts, dry corns. This drug is used mainly in medical institutions.

2. Resorcinol

2.1 Physical Properties

Resorcinol is meta-dihydroxybenzene. Colorless crystals, up to 70.8°C exist in the a-modification, higher in the p-modification. If stored incorrectly, resorcinol becomes pinkish-orange due to easy oxidation. phenol resorcinol pyrocatechin phloroglucinol

May spontaneously ignite at 608°C. Melts at a temperature of 109-110°C. Flashes at 127°C. Starts to boil at 280.8°C. Easily soluble in ethanol, diethyl ether, acetone, water, sparingly soluble in CHCl 3 , CS 2 , benzene (in 100 g 2.2 g at 20 °C, 14.1 g at 60 °C).

With picric acid gives picrate. When nitric acid acts on resorcinol, resazurin is formed.

Color reaction to resorcinol - when interacting with iron chloride, a dark purple color appears, turning into black.

2.2 Impact on the human body

Vapors and dust of resorcinol can irritate the skin, mucous membranes of the eyes, as well as respiratory organs. Once in the lungs, they provoke a temporary and chronic cough. Has a specific smell.

2.3 Application in medicine and pharmacy

Resorcinol is a cauterizing and disinfectant. It is used in low concentrations (0.25-2%) as part of lotions and ointments as a keratoplastic (epithelizing, healing) agent, is prescribed for weeping lesions as an astringent, anti-inflammatory agent, stimulates regenerative processes, and has an antiseptic effect.

Higher concentrations of resorcinol (5-10% ointment) have specific keratolytic (promoting rejection of the stratum corneum) and cauterizing properties - they dry the stratum corneum, which takes the form of parchment, after which it is easily removed.

30-50% concentration of resorcinol has a pronounced cauterizing effect.

Indications for use:

a) Resorcinol is prescribed externally for skin diseases - itchy skin, eczema, sycosis, seborrhea, fungal skin diseases, for cauterization of genital warts;

b) Resorcinol is also used for acne and freckles, for alopecia - as an irritant;

c) Resorcinol is part of the Fucorcin combination drug used to treat fungal diseases, some skin diseases and as an antiseptic.

3. Pyrocatechin

3.1 Physical Properties

By appearance Pyrocatechin is a colorless crystalline substance that tends to turn brown in open light.

Melting point 104.8°C, Boiling point 245°C; 170°C at 13.3 kPa. Vapor pressure 1.33 kPa at 104.3°C. Solubility in water 8.5% at 20ºC.

Pyrocatechin is highly soluble in substances such as diethyl ether, acetone, ethanol, water, pyridine, it dissolves much worse benzene, chloroform and other liquids. General affiliation to the group of phenols determined the dependence of properties on this general category. This property determined many practical indicators and chemical reactions characteristic of pyrocatechol.

Appearance aqueous solution in air, it oxidizes very quickly and changes color to green, and then black.

3.2 Impact on the human body

Pyrocatechin is an allergen that causes occupational skin diseases. There are experimental data on the possibility of mutagenic and carcinogenic effects. Similar to other phenols, it excites the centers of the medulla oblongata, dyspneic breathing appears, blood pressure rises, and in case of an overdose, convulsions and paralysis of the central nervous system. Poison became the basis for the refusal of the active use of catechol in medicine.

3.3 Application in medicine and pharmacy

The use of pyrocatechol is justified by its basic properties. In the chemical industry and related industries, catechol is used as a feedstock, and guaiacol, veratrol and other esters are produced from it. With the help of catechol, a synthetic method was mastered for obtaining some varieties of catecholamine with neurotransmitter and hormonal properties, such as adrenaline, epinephrine, norepinephrine, dopamine. In the field of photography, pyrocatechin is used as a developer, in pharmacology - for the synthesis of papaverine.

4. hydroquinone

4.1 Physical Properties

1) Boiling point: 287°C;

2) Melting point: 172°C;

3) Relative density (water = 1): 1.3;

4) Solubility in water, g/100 ml at 15°C: 5.9;

5) Vapor pressure, Pa at 20°C: 0.12;

6) Relative vapor density (air = 1): 3.8;

7) Relative density of steam/air mixture at 20°C (air = 1): 1;

8) Flash point: 165°C;

9) Auto ignition temperature: 515°C.

4.2 Impact on the human body

The main negative effect of this chemical on the human body is a decrease in the production of melanin (pigment) in the skin and hairline. At the same time, it affects the deep layers of the skin, as a result of ultraviolet radiation and its own carcinogenic effects, it leads to an increased risk of developing skin cancer. Hydroquinone, when it enters the human body, interacts with blood hemoglobin, forming a strong oxidizing agent - n-benzoquinone. Despite the fact that this substance is prohibited in Europe for use in cosmetology, nevertheless, in the territory of some Western countries and the CIS is found in the sale of American-made personal care products. In the US, up to 2% hydroquinone is considered safe and approved.

Hydroquinone as a carcinogen (immunotoxicant) negatively affects the development of the fetus during pregnancy, as well as the endocrine and nervous system, the work of some organs.

With excessive use of products containing hydroquinone - bleaching creams, ointments - it is possible to develop ochronosis, a skin disease in which the skin acquires a grayish-brown color and is covered with age spots.

4.3 Application in medicine andpharmacy

In cosmetic preparations, it was previously used as a component for skin whitening, but in last years almost everywhere banned because of the high danger to the skin. As an inhibitor of the reaction of free radical polymerization, methyl methacrylate is included in the composition of dental composite materials of chemical curing.

5. Phloroglucinol

5.1 Physical Properties

Phloroglucinum - colorless lamellar crystals. Molecular mass: 126.12 amu Melting point: 219°C. Density: 1.46 (20°C, g/cm3).

Solubility (in g/100 g or specification):

1) benzene: highly soluble;

2) water: 1 (20°C);

3) water: 1.13 (25°C);

4) diethyl ether: easily soluble;

5) pyridine: highly soluble;

6) ethanol: easily soluble.

5.2 Application in medicine and pharmacy

Included in the composition of flavones and catechins in the form of glycosides. Used for the qualitative and quantitative determination of pentoses and pentosans. Furfural released during the hydrolysis of pentoses in the presence of of hydrochloric acid forms a red, water-insoluble precipitate with phloroglucinol.

Conclusion

Phenols -- organic compounds aromatic series, in the molecules of which the hydroxyl groups are bonded to the carbon atoms of the aromatic ring. According to the number of OH groups, they distinguish:

a) monohydric phenols (arenols): phenol (C 6 H 5 OH) and its homologues;

b) dihydric phenols (arendiols): hydroquinone, catechol, resorcinol;

c) trihydric phenols (arentriols): pyrogallol, phloroglucinol, hydroxyhydroquinone, etc.

Most monohydric phenols under normal conditions are colorless crystalline substances with a low melting point and a characteristic odor. Phenols are poorly soluble in water, readily soluble in organic solvents, toxic, and gradually darken when stored in air as a result of oxidation.

Phenols are used in the production of various phenol-aldehyde resins, polyamides, polyarylates, polyarylene sulfones, epoxy resins, antioxidants, bactericides and pesticides (for example, nitrafen). Alkylphenols are used in the production of surfactants, stabilizers and fuel additives. Dihydric phenols and their derivatives are part of tanning agents for leather and fur, modifiers and stabilizers of rubbers and rubbers, and are used for processing film and photographic materials.

In medicine, phenols and their derivatives are used as antimicrobial (phenol, resorcinol), anti-inflammatory (salol, osarsol), antispasmodic (adrenaline, papaverine), antipyretic (aspirin, salicylic acid), laxatives (phenolphthalein), adrenolytic (mesatone), astringents ( tannins) and other medicines, as well as vitamins E and P.

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