Boiling point of chloroform at atmospheric pressure. Chloroform. properties of chloroform. Application of chloroform

Chloroform(aka trichloromethane, methyl trichloride, freon 20) is an organic chemical compound with the formula 3. At normal conditions colorless volatile liquid c ethereal scent and sweet taste. Practically insoluble in water - forms solutions with it with mass fraction up to 0.23%, - miscible with most organic solvents. Non-combustible Phosgene poisoning is possible when working with chloroform, which has been stored for a long time in the light in a warm place.

Story

Chloroform was first obtained in 1831 independently as a solvent for rubber by Samuel Guthrie, then by Justus von Liebig and Eugène Soubeiran.

The French chemist Dumas established the formula for chloroform. He also came up with the name “chloroform” in the city, due to the property of this compound to form formic acid during hydrolysis (lat. formica translates as "ant").

AT clinical practice Chloroform was first used as a general anesthetic by Holmes Coote in 1847, and was introduced into widespread practice by obstetrician James Simpson, who used chloroform to relieve pain during childbirth.

In Russia, the method for the production of medical chloroform was proposed by the scientist Boris Zbarsky in 1916, when he lived in the Urals in the village of Vsevolodo-Vilva in the Perm Territory.

Physical properties

• Refractive index: 1.44858 at 15°C.
• Crystallization temperature: -63.55 °C
• Boiling point: 61.152 °C
• Dipole moment: 1.15 debay
• Dielectric constant: 4.806 at 20°C

Chemical properties

In the laboratory, chloroform can also be obtained from the reaction between acetone or ethanol and bleach.

Commercially available chloroform contains ethanol(1-2%) as a stabilizer that binds phosgene formed during long-term storage in the light and in the presence of oxygen. Chloroform is used in the Beilstein test, in this reaction, a bluish-green color of the flame is observed with copper ions.

$~\backslash mathsf(5CuO\; +\; 2CHCl\_3\; \backslash longrightarrow\; \backslash \; 3CuCl\_2\; +\; 2CO\_2\; +\; H\_2O\; +\; 2Cu)$

Application

$\backslash mathsf(CHCl\_3\; +\; 2HF\; \backslash xrightarrow(SbCl\_5)\; CF\_2HCl\; +\; 2HCl)$

Chloroform is also used as a solvent in the pharmaceutical industry and in the manufacture of dyes and pesticides. Chloroform containing deuterium (CDCl 3 ) is the most common solvent used in nuclear magnetic resonance (NMR).

cleaning

The cleaning process is divided into a number of stages. First, chloroform is shaken with concentrated sulfuric acid, washed with water, dried over calcium chloride or magnesium sulfate, and distilled. You can check the purity of chloroform by evaporation from filter paper: after chloroform, there should be no smell. A musty, pungent, irritating smell indicates the presence of impurities of chlorine, hydrogen chloride or phosgene.

Impact on the body

Inhalation of chloroform adversely affects the functioning of the central nervous system. Inhalation of air containing about 0.09% chloroform (900 ppm) per a short time may cause dizziness, fatigue and headache. Chronic exposure to chloroform can cause liver and kidney disease. Approximately 10% of the world's population has an allergic reaction to chloroform, resulting in an increase in body temperature (up to 40 ° C). Often causes vomiting (the frequency of postoperative vomiting reached 75-80%).

Animal studies have shown that pregnant rats and mice that breathe air containing 0.003% chloroform (30 ppm) miscarried. This has also been observed in rats given chloroform orally. Subsequent generations of rats and mice that inhaled chloroform had a higher percentage of birth defects than healthy individuals.

The effect of chloroform on reproduction in humans is not well understood. At long-term exposure on the Airways and human mucous membranes (2-10 minutes) possible fatal outcome. Suspected to be mutagenic and carcinogenic. These properties appear only when the concentration of chloroform in the air is exceeded.

When ingested, chloroform is quickly excreted with exhaled air: after 15-20 minutes. - 30-50% chloroform, within an hour - up to 90%. The rest of chloroform in the body is converted into carbon dioxide and hydrogen chloride as a result of biotransformation.

$~\backslash mathsf(2CHCl\_3\; +\; 2H\_2O\; +\; O\_2\backslash longrightarrow\; \backslash \; 2CO\_2\backslash uparrow\; +\; 6HCl\backslash uparrow)$

Forms phosgene with atmospheric oxygen if stored improperly:

$~\backslash mathsf(2CHCl\_3\; +\; O\_2\backslash longrightarrow\; \backslash \; 2COCl\_2\backslash uparrow\; +\; 2HCl\backslash uparrow)$

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Notes

An excerpt characterizing Chloroform

The rest of the infantry hurried across the bridge, vortexing at the entrance. Finally the wagons all passed, the crush became less, and the last battalion entered the bridge. Some hussars of Denisov's squadron remained on the other side of the bridge against the enemy. The enemy, visible in the distance from the opposite mountain, from below, from the bridge, was not yet visible, since from the hollow along which the river flowed, the horizon ended with the opposite elevation no further than half a verst. Ahead was a desert, along which in some places groups of our traveling Cossacks were moving. Suddenly, on the opposite elevation of the road, troops in blue hoods and artillery appeared. These were the French. The Cossacks' troop moved off downhill at a trot. All the officers and people of Denisov's squadron, although they tried to talk about strangers and look around, did not stop thinking only about what was there, on the mountain, and incessantly peered into the spots that appeared on the horizon, which they recognized as enemy troops. The weather cleared up again in the afternoon, the sun set brightly over the Danube and the dark mountains surrounding it. It was quiet, and from that mountain occasionally came the sounds of horns and cries of the enemy. There was no one between the squadron and the enemy, except for small sidings. An empty space, three hundred fathoms, separated them from him. The enemy stopped firing, and the more clearly felt that strict, formidable, impregnable and elusive line that separates the two enemy troops.
“One step beyond this line, reminiscent of the line separating the living from the dead, and - the unknown of suffering and death. And what's there? who's there? there, behind this field, and a tree, and a roof lit by the sun? Nobody knows, and one wants to know; and it’s scary to cross this line, and I want to cross it; and you know that sooner or later you will have to cross it and find out what is there, on the other side of the line, just as it is inevitable to find out what is there, on the other side of death. And he himself is strong, healthy, cheerful and irritable, and surrounded by such healthy and irritably lively people. So if he does not think, then every person who is in sight of the enemy feels, and this feeling gives a special brilliance and joyful sharpness of impressions to everything that happens at these moments.
The smoke of a shot appeared on a hillock near the enemy, and the ball, whistling, flew over the heads of the hussar squadron. The officers who had been standing together dispersed to their places. The hussars diligently began to straighten the horses. Everything in the squadron went silent. Everyone looked ahead at the enemy and at the squadron commander, waiting for the command. Another, third core flew by. It is obvious that they fired at the hussars; but the cannonball, whistling evenly quickly, flew over the heads of the hussars and hit somewhere behind. The hussars did not look back, but at every sound of a flying cannonball, as if on command, the entire squadron with its monotonously diverse faces, holding its breath while the cannonball flew, rose in the stirrups and lowered again. The soldiers, without turning their heads, squinted at each other, curiously looking for the impression of a comrade. On each face, from Denisov to the bugler, one common feature struggle, anger and excitement. The sergeant-major frowned, looking at the soldiers, as if threatening punishment. Junker Mironov stooped down with each passage of the core. Rostov, standing on the left flank on his touched but visible Grachik, had the happy look of a student called before a large audience for an exam, in which he was sure that he would excel. He looked around clearly and brightly at everyone, as if asking them to pay attention to how he calmly stands under the cannonballs. But in his face, too, the same feature of something new and strict, against his will, was shown near the mouth.
- Who bows there? Yunkeg "Mig" ons! Hexog "oh, look at me" ite! - shouted Denisov, who could not stand still and who was spinning on a horse in front of the squadron.
The snub-nosed and black-haired face of Vaska Denisov and his whole small, knocked-down figure with his sinewy (with short fingers covered with hair) hand, in which he held the hilt of a drawn saber, was exactly the same as always, especially in the evening, after drinking two bottles. He was only redder than usual, and, throwing his shaggy head up like birds when they drink, ruthlessly pressing his spurs into the sides of the good Bedouin with his small feet, he, as if falling back, galloped to the other flank of the squadron and hoarse voice shouted to inspect the pistols. He drove up to Kirsten. The staff captain, on a broad and sedate mare, rode towards Denisov at a pace. The captain's staff, with his long mustaches, was as serious as ever, only his eyes shone more than usual.
– Yes what? - he said to Denisov, - it will not come to a fight. You'll see, let's go back.
- Chog "does not know what they are doing," grumbled Denisov. "Ah! G" skeleton! he shouted to the cadet, noticing his cheerful face. - Well, I waited.
And he smiled approvingly, apparently rejoicing at the junker.
Rostov felt completely happy. At this time, the chief appeared on the bridge. Denisov galloped up to him.

Photo of the drug

Latin name: Chloroformium

ATX code: N01AB02; M02AX10

Active substance: Chloroform (Chloroformium)

Analogues: no data

Producer: RuiyuanGroupLimited, China (Chloroform for anesthesia); Dentalife, Australia; Technochemistry LLC, Ukraine; LLC NPP “SILUR”, Ukraine; OOO HaloPolymer Kirovo-Chepetsk, Russian Federation; OJSC Khimprom, RF

The description applies to: 27.09.7

Chloroform (aka trichloromethane, methyl trichloride, freon 20) - organic chemical compound with the formula CHCl 3 . Under normal conditions, a colorless volatile liquid with an ethereal odor and a sweet taste. It is practically insoluble in water - it forms solutions with it with a mass fraction of up to 0.23%, - it is miscible with most organic solvents. Non-combustible Phosgene poisoning is possible when working with chloroform, which has been stored in a warm place for a long time.

Chloroform was first obtained in 1831 independently as a solvent for rubber by Samuel Guthry, then by Justus von Liebig and Eugene Soubeiran.

The result of the process is a mixture consisting of methyl chloride, dichloromethane, chloroform and carbon tetrachloride. The separation of substances is carried out by distillation.

In the laboratory, chloroform can also be obtained by the reaction between acetone or ethanol and bleach.

You can also get chloroform at home by heating trichloroacetic acid to 75 ° C.

Commercially available chloroform contains ethyl alcohol (1-2%) as a stabilizer, which binds phosgene formed during long-term storage in the light and in the presence of oxygen.

AT late XIX and the beginning of the 20th century, chloroform was used as an anesthetic during surgical operations. For the first time, chloroform was used as an anesthetic in surgical operations. English doctor Simpson (1848). In Russia, chloroform as a means for general anesthesia was first used by N.I. Pirogov. However, in this role, chloroform was subsequently replaced by safer substances.

Chloroform is also used as a solvent in the pharmaceutical industry, and in the production of dyes and pesticides.

Inhalation of chloroform adversely affects the functioning of the central nervous system. Inhaling about 900 parts of chloroform to 1 million parts of air in a short time can cause dizziness, fatigue, and headache. Chronic exposure to chloroform can cause liver and kidney disease. Approximately 10% of the world's population has allergic reaction to chloroform, leading to an increase in body temperature (up to 40 ° C). Often causes vomiting (the frequency of postoperative vomiting reached 75-80%).

Animal studies have shown that pregnant rats and mice that breathe a mixture containing 30 parts of chloroform per 1 million parts of air miscarry. This has also been observed in rats given chloroform by mouth. Subsequent generations of rats and mice that inhaled chloroform had a higher percentage of birth defects than healthy individuals.

The effect of chloroform on reproduction in humans is not well understood. With prolonged exposure to the respiratory tract and mucous membranes of a person (2-10 minutes), a fatal outcome is possible. Suspected to be mutagenic and carcinogenic. These properties appear only when the concentration of chloroform in the air is exceeded.

Lethal dose when administered orally 20 ml, with inhalation 40 ml. Toxic concentration in blood 70-250 mg/l, lethal 390 mg/l

conclusions

Organochlorine compounds are very diverse in application. But most often these are insecticides, that is, substances that are used to control pests, in particular insects, and pesticides.

1. DDT, it is also called "dust" in the common people, has been around for a long time, and adversely affects human health. It is important to note that, like many pesticides, it does not have carcinogenic properties, that is, when it accumulates in the human body, tumors do not form. However, it adversely affects the reproductive system.

2. Hexachloran is also non-carcinogenic and less dangerous than DDT. Basically it hurts nervous system and parenchymal organs, i.e. liver and kidneys.

3. Ovotran is also an insecticide. It mainly affects the organs of the upper respiratory tract and the cardiovascular system.

4. Meta-chlorophenylpiperazine is not a pesticide or insecticide. However, it is very harmful to the human body. It is also called "ecstasy" narcotic substance, which can cause dysphoria, panic, nausea, and headache.

5. Chloroform is one of the popular organochlorine compounds. At the beginning of the 20th century used as an anesthetic during surgical operations. Today it is used as a solvent in the pharmaceutical industry. Inhalation of chloroform may cause dizziness, fatigue, and headache. Chronic exposure to chloroform causes liver and kidney disease.

List of used literature:

1. Industrial organochlorine products. Handbook / Ed. L.A. Oshina. - M.: Chemistry, 1978. - 656 pages, ill.

2. Melnikov N.N., Novozhilkov K.V., Pylova T.N. Chemicals plant protection (pesticides). Reference book: - M.: Chemistry, 1980. - 288 p.

3. http://ximuk.ru/vvp/2/600.html

4. Tarasov A.V. Smirnova A.V. Fundamentals of toxicology

5. M.: Folio, 2004. - 570 p. - ISBN: 5-93929-092-2.

Questions for self-control:

1. What are organochlorines most often used for?

2. Are DDT and hexachlorane carcinogenic?

3. What is the advantage of lindane over DDT in terms of human health?

4. What are acaricides used for?

5. What is the harm of Meta-chlorophenylpiperazine, and what is it also called?

6. When and by whom was chloroform obtained?

7. What is chloroform chemically? Name it according to the IUPAC system.

8. Is it possible to get chloroform at home? If so, write the reaction equation and characteristic conditions.

9. In what area, and for what purpose was chloroform used?

10. Why is chloroform not used in medicine today?

Tests:

1.DDT is used as:

a) insecticide

b) pesticide

c) acaricide

d) herbicide

2. On which organ system is the harm of organochlorine compounds most often concentrated:

a) respiratory system

b) cardiovascular system

c) the nervous system

3. In addition to the central nervous system, which organs suffer primarily from the effects of organochlorine compounds?

b) liver, kidneys

c) intestines, stomach

4. Chloroform formula:

d) CHCl 3

5. What was chloroform used for at first (late 19th century)?

a) as a solvent for rubber

b) as a solvent in the pharmaceutical industry

c) as a poison

6. Due to the fact that organochlorine compounds are lipophilic, how can they be removed from the body?

a) rinsing with water

b) washing with soda

c) washing with camphor oil

empirical formula. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . CHCl3

Molecular weight, kg/kmol. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 119.38

State of aggregation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . liquid

Appearance. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .colorless liquid

Smell. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . characteristic sweet smell

Application: as a starting material for the synthesis of freons (freons), as a solvent in laboratory practice and technology.

PHYSIOCHEMICAL PROPERTIES

Density at 20°C and pressure 101.3 kPa, kg/m3. . . . . . . . . . . . . . . . . . . . 1483

Boiling point, °С. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61.2

Melting point, °С. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . minus 63.5

Critical temperature, °C. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 262

Critical pressure, MPa. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.53

Heat of formation, kJ/mol. . . . . . . . . . . . . . . . . . . . . . . . . . . . . minus 131.8

Heat capacity, J / (mol? deg) . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . .116.3

Heat capacity, cal / (mol? ° deg) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .27.96

Solubility in water: . . . . . . . . . . . . . . . . . . . . . . . . practically insoluble.

Reactivity: soluble in most organic solvents. In the light, it is slowly oxidized by atmospheric oxygen. Dissolves fats, rubber, resins, phosphorus, iodine. Hydrolyzes with dilute alkali.

Reacting with bases, intermediately forms dichlorocarbene. With alcoholates gives orthoformic esters.

SANITARY AND HYGIENIC CHARACTERISTICS

CAS registration number. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67-66-3

Hazard class in the air of the working area. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .2

MPCm.r./d.s. in the air of the working area, mg/m3. . . . . . . . . . . . . . . . . . . . . . . . . . . . 10/5

Air pollutant code: . . . . . . . . . . . . . . . . 0898

Hazard class in atmospheric air. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .2

MPCm.r./d.s. in atmospheric air, mg/m3. . . . . . . . . . . . . . . . . . . . . . . . . 0.1/0.03

Impact on people: has a strong narcotic and anesthetic effect; due to significant toxicity to surgical anesthesia does not apply. Has a toxic effect on metabolism and internal organs especially on the liver.

Precautions: sealing equipment and communications, ventilation.

Means of protection: filtering industrial gas mask, hose gas mask with forced air supply. Special protection for skin and eyes.

FIRE AND EXPLOSION PROPERTIES

Flammability group. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . nonflammable liquid

Gross formula

Pharmacological group of substance Chloroform

Nosological classification (ICD-10)

CAS code

Characteristics of the substance Chloroform

Colorless, transparent, heavy mobile volatile liquid with a characteristic odor and a sweet burning taste. Miscible in all proportions with anhydrous ethanol, ether, gasoline, ethereal and fatty oils. Slightly soluble in water (1:200). Density 1.474-1.483. Boiling point 59.5-62 °C.

Pharmacology

The ability of chloroform to cause general anesthesia was opened in 1848. Provides irritant effect on the respiratory tract, has a cardiotonic effect, affects the central regulation of blood circulation. With deep chloroform anesthesia, pressor reflexes from the aortic and carotid sinus regions are weakened, which indicates a decrease in the excitability of the bulbar vasomotor center. Weakening of the work of the heart is caused not only central action chloroform, but also its direct effect on the heart. May cause extrasystoles and life-threatening ventricular flutter, acidosis, and liver and kidney dysfunction. After prolonged chloroform anesthesia, as a result of a violation of tissue metabolism, signs of degeneration may appear. parenchymal organs(in a few days, the so-called "late" death is possible).

Currently, as an anesthetic is used very rarely.

Excites nerve endings on the skin and mucous membranes, promotes the release of endorphins, enkephalins and other peptides responsible for the regulation pain, vascular permeability, etc. Improves blood supply to tissues and helps relieve pain. The effectiveness of the combination with valerian tincture is shown in functional disorders GI tract.