Diethyl ether(ethyl ether, sulfuric ether). In terms of chemical properties, it is a typical aliphatic ether. Widely used as a solvent. First obtained in the Middle Ages.

Story

It is possible that diethyl ether was first obtained in the 9th century by the alchemist Jabir ibn Hayyan or the alchemist Raymond Lull in 1275. It is reliably known that it was synthesized in 1540 by Valerius Cordus, who called it “sweet oil of vitriol” (lat. oleum dulce vitrioli), since it was obtained by distilling a mixture of ethyl alcohol and sulfuric acid, which was then called “oil of vitriol.” Cordus also noted its anesthetic properties.

The name "ether" was given to this substance in 1729 Frobenius .

Synthesis

It is obtained by the action of acid catalysts on ethyl alcohol when heated, for example by distilling a mixture of ethyl alcohol and sulfuric acid at a temperature of about 140-150 °C. It is also obtained as a by-product in the production of ethyl alcohol by hydration of ethylene in the presence of phosphoric acid or 96-98% sulfuric acid at 65-75 ° C and a pressure of 2.5 MPa. The main part of diethyl ether is formed at the stage of hydrolysis of ethyl sulfates (95-100 °C, 0.2 MPa)

Properties

• Colorless, transparent, very mobile, volatile liquid with a peculiar odor and pungent taste.
• Solubility in water 6.5% at 20 °C. Forms an azeotropic mixture with water (bp 34.15 °C; 98.74% diethyl ether). Mixes with ethanol, benzene, essential and fatty oils in all proportions.
• Highly flammable, including vapors; In a certain ratio with oxygen or air, ether vapors for anesthesia are explosive.
• Decomposes when exposed to light, heat, air and moisture to form toxic aldehydes, peroxides and ketones, which are irritating to the respiratory tract.
• The resulting peroxides are unstable and explosive; they can cause spontaneous ignition of diethyl ether during storage and explosion during its distillation to dryness.

In terms of chemical properties, diethyl ether has all the properties characteristic of ethers, for example, it forms unstable oxonium salts with strong acids:

$\backslash mathsf((C\_2H\_5)\_2O\; +\; HBr\; \backslash rightarrow\; [(C\_2H\_5)\_2OH]^+Br^-)$

Forms relatively stable complex compounds with Lewis acids: (C 2 H 5) 2 O BF 3

Application

Pharmacology

In medicine it is used as a general anesthetic drug, since its effect on neuronal membranes and the ability to “immobilize” the central nervous system is very specific and completely reversible. It is used in surgical practice for inhalation anesthesia, and in dental practice - topically, for the treatment of carious cavities and root canals of the tooth in preparation for filling.

Due to the slow decomposition of diethyl ether, the established storage periods must be strictly adhered to. For anesthesia, ether can only be used from bottles opened immediately before surgery. After every 6 months of storage, ether for anesthesia is checked for compliance with the requirements. The use of technical ether for these purposes is not permitted.

Technique

• It is used as a solvent for cellulose nitrates in the production of smokeless powder, natural and synthetic resins, and alkaloids.
• It is used as an extractant for the separation of plutonium and its fission products during the production and processing of nuclear fuel, and for the separation of uranium from ores.
• It is used as a fuel component in model aircraft compression engines.
• When starting gasoline internal combustion engines in harsh winter conditions.

In the USSR, Arctic starting fluid was produced; a small amount was poured into the intake manifold through the carburetor with the air filter removed. For the army, ether was produced in a sealed aluminum casing; before use, the casing was pierced with a bayonet or screwdriver. Abroad, “starting fluid on cold days” is produced in an aerosol can. Ingredients: diethyl ether, industrial oil, propellant.

The engine starting mechanism in this case is mostly diesel: the mixture of ether and air is ignited by compression already at a compression ratio of about 5-6; Engines that have lost compression for various reasons can make several revolutions on ether, but nevertheless do not work on gasoline.

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Notes

Literature

• Babayan E. A., Gaevsky A. V., Bardin E. V. “Legal aspects of the circulation of narcotic, psychotropic, potent, toxic substances and precursors” M.: MCFR, 2000 p. 148
• Gurvich Ya. A. “Handbook of a young apparatchik-chemist” M.: Chemistry, 1991 p. 229
• Devyatkin V.V., Lyakhova Yu.M. “Chemistry for the curious, or what you won’t learn about in class” Yaroslavl: Academy Holding, 2000 p. 48
• Rabinovich V. A., Khavin Z. Ya. “A short chemical reference book” L.: Chemistry, 1977 p. 148
• Hauptmann 3., Organic chemistry, trans. from German, M.: Khimiya, 1979, p. 332-40;
• Graefe Yu., General organic chemistry, trans. from English, vol. 2, M., 1982, p. 289-353;
• Remane X., Kirk-Othmer encyclopedia, v. 9, N.Y., 1980, p. 381-92.

Excerpt characterizing Diethyl Ether

1 liter

Typical aliphatic ether.
Widely used as a solvent.
First obtained in the Middle Ages.

Chemical formula C₄H₁₀O

Melting point-116.3 °C

Boiling point 34.65 °C

Russian name

Diethyl ether

Latin name of the substance Diethyl ether

Aether diaethylicus (genus. Aetheris diaethylici)

Chemical name
1,1-Hydroxy-bis-ethane

Gross formula

Characteristics of the substance Diethyl ether

Ethyl acetate is a typical aliphatic ether.
Molecular weight = 74.1 grams per mole.
The substance is also called: ethyl, sulfuric ether.
This is a colorless liquid, mobile and very transparent, has a specific smell and taste.
The substance is poorly soluble in water and forms an azeotropic mixture with it.
Mixes freely with benzene, fatty oils, ethyl alcohol.
The compound is volatile and flammable, and is explosive when combined with oxygen or air.
The anesthetic drug contains about 96-98% of the substance, the density of the medical ether is 0.715.
The product boils at 35 degrees Celsius.

Structural formula of Diethyl Ether:

CH3-CH2-O-CH2-CH3

The substance has homologues and isomers.
The isomer of Diethyl Ether is: methylpropyl (CH3-CH2-CH2-O-CH3) And methyl isopropyl ethers .
Propionic acid ethyl ester formula: С5Н10О2.
Chemical formula of acetic acid ethyl ester: CH3-COO-CH2-CH3.

The substance decomposes when exposed to heat, air and light, forming toxic aldehydes, ketones and peroxides.
The compound also has all the chemical properties that are characteristic of ethers and forms oxonium salts and complex compounds.

Preparation of Diethyl Ether

The substance can be synthesized by the action of acid catalysts on ethyl alcohol. For example, Diethyl Ether is obtained by distilling sulfuric acid and ethylene at high temperatures (about 140-150 degrees). The compound can also be formed as a by-product in the hydration of ethylene with acetic or sulfuric acid at appropriate pressure and temperature.

• The product is widely used in medicine;
• used as a solvent for cellulose nitrates in the production of smokeless vice, synthetic and natural resins, alkaloids;
• in the production of fuel for aircraft model engines;
• used for gasoline internal combustion engines at low temperatures;
• the substance is used in the reprocessing of nuclear fuel as an extractant to separate plutonium and its fission products, uranium from ore, and so on.
  

Where and how to buy Diethyl Ether?

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Esters are products of substitution of the hydrogen atom of the hydroxyl group of alcohols or phenols with the carbon radical R: R1-O-R2. Diethyl ether - formula H3C-O-CH3. Esters are characterized by hydrocarbon chain isomerism and metamerism. The first is due to the branching of the hydrocarbon chain. Metamerism is a type of isomerism in which two or more ethers have the same molecular formula, but different molecular structures due to different radicals on both sides of the oxygen “bridge.”

Diethyl ether: preparation

Esters are obtained synthetically (they are not found in nature in a free state). In order to synthesize esters, several methods can be used: using mineral acids, the interaction of alcoholates with halogen alkyls. Dimethyl and methyl ethyl ethers have a gaseous state, the next few representatives are solutions, and the higher ones are solids. Esters are poorly soluble in water, but well in water, and the middle representatives (diethyl ether, propyl and dipropyl ethers) are excellent organic solvents. they vary depending on Diethyl ether mixes well with alcohol, chloroform, benzene, essential oils, and also with fatty oils. If the storage conditions of ether are violated, toxic and explosive compounds - hydroperoxides - are formed in it.

Diethyl ether is used in medicine. It is used for inhalation anesthesia. This type of anesthesia is characterized by a pronounced stage of excitation (cardiac activity increases, vascular tone increases, catecholamine excretion is activated, the concentration of glucose, pyruvic and lactate acids in the blood increases, the secretory and motor functions of the digestive tract are inhibited). You should know that when using this type of ether, anesthesia occurs slowly, and very often you will observe strong agitation and motor activity. In general, anesthesia has a multifaceted effect on the human body (muscle-relaxing, analgesic and narcotic).

The local effect of the ether manifests itself in the form of irritation of nerve endings, as a result of which the patient feels a cooling effect. In this regard, it is sometimes used internally to regulate motor function and subcutaneously to reflexively stimulate breathing and improve blood circulation. When inhaled, ether vapors irritate the respiratory tract, which first causes a reflex inhibition of breathing, after which it activates the secretion of the bronchial glands. For the first time, diethyl ether was used for inhalation anesthesia by the outstanding Russian surgeon N.I. Pirogov, the founder of military field surgery, during the Crimean War (1853-1856).

Diethyl ether is easily absorbed by the mucous membrane of the respiratory tract, but complete anesthesia occurs a little later compared to chloroform. The narcotic effect occurs only when inhaling 5-8% of the mixture of ether vapors, and complete anesthesia occurs within 30 minutes when inhaling 10% of the mixture. The narcotic effect of the drug manifests itself in a concentration of 110 to 150 mg per 100 ml of blood, paralysis of the respiratory center occurs at 200 mg/100 ml of blood. The overall toxicity of the ether is insignificant. Awakening after anesthesia occurs 20-40 minutes after stopping the inhalation of ether, but the body returns to a normal state only after a few hours. The ether is released through the respiratory tract and through the kidneys. Approximately 50% of its total amount is excreted from the body in the first 30-60 minutes after the end of anesthesia. It should be said that some products of diethyl ether hydrolysis can be localized in triglycerides and other lipids for up to several days.

Gross formula

Pharmacological group of the substance Diethyl ether

Nosological classification (ICD-10)

CAS code

Characteristics of the substance Diethyl ether

Colorless, transparent, very mobile, volatile liquid with a peculiar odor and pungent taste. Anesthesia ether contains 96-98% diethyl ether. The density of anesthesia ether is 0.713-0.714, medical ether 0.714 - 0.717, boiling point 34-35 °C and 34-36 °C, respectively. When 1 ml of anesthesia ether is evaporated, 230 ml of steam is formed; the vapor density of the ether for anesthesia is 2.6, the relative molecular weight is 74. It decomposes under the influence of light, heat, air and moisture to form toxic aldehydes, peroxides and ketones that irritate the respiratory tract. Solubility in water 1:12. Mixes with alcohol, benzene, essential and fatty oils in all proportions. Highly flammable, incl. couples; in a certain ratio with oxygen, air and dinitrogen oxide, ether vapors for anesthesia are explosive.

Pharmacology

Non-specifically interacts with neuronal membranes, mainly with bilayer lipid membranes of axons of the brain, medulla oblongata and spinal cord, reversibly changes their ultrastructure and functions. Depresses the central nervous system: blocks synaptic transmission of excitation (mainly afferent impulses), functionally disintegrates cortical-subcortical interactions while maintaining the activity of bulbar centers. Causes clearly defined “classical” stages of anesthesia - analgesia, excitement, surgical anesthesia with 3 levels (superficial, medium, deep) and characteristic signs: lack of consciousness and all types of sensitivity, inhibition of reflex reactions and relaxation of skeletal muscles.

In the case of premedication and against the background of other inhalational or non-inhalational general anesthetics, the classic picture of anesthesia changes significantly. At the analgesic stage, it reduces the functional activity of cortical neurons and causes an amnestic effect. In the stage of excitation, it inhibits the cerebral cortex, turns off subordination mechanisms that control the state of subcortical structures (mainly the midbrain). An increase in the activity of subcortical formations is manifested by psychomotor agitation, variability of breathing, blood pressure, pulse, etc.). This stage is more pronounced in adults than in children, less (or absent) during premedication and basic anesthesia. Irritates mucous membranes, incl. oral cavity, increases the secretion of the salivary glands (hypersalivation). Through the receptor zones of the trigeminal, laryngeal and vagus nerves, it increases bronchial secretion; causes cough, laryngospasm, spasm of the bronchi (changed during deep anesthesia by their expansion), respiratory disorders (reflex stimulation or inhibition, up to apnea) and cardiac activity (tachycardia or bradycardia, cardiac arrest), hypertension. When saliva or mucus saturated with ether enters the stomach, it irritates its mucous membrane, reflexively stimulates the vomiting center, causing nausea and vomiting (in the beginning of anesthesia and upon awakening).

During the stage of surgical anesthesia, it significantly inhibits interneuronal transmission in the brain and spinal cord. Increases the activity of parts of the hypothalamus that regulate the functions of the pituitary-adrenal cortex system and the sympathetic nervous system, increases the secretion of glucocorticoids and catecholamines. Increases the release of adrenaline from the adrenal medulla, causes hyperglycemia, vasospasm of internal organs, increases blood pressure, heart rate and heart rate (does not sensitize the myocardium to catecholamines). Activation of the sympathetic nervous system neutralizes the inhibitory effect on vascular tone, blood pressure and cardiac function. Increases capillary bleeding, inhibits intestinal motility (at the beginning of anesthesia). Relaxes skeletal muscles, because disrupts the central regulation of muscle tone and blocks the propagation of local potential on the postsynaptic membrane of skeletal muscle.

In high concentrations, it directly inhibits the respiratory and vasomotor centers (impaired pulmonary ventilation, hypotension) and has a direct cardiodepressive effect. Causes cooling of the lung tissue, which, in combination with the accumulation of mucus in the bronchi (due to the irritating effect), contributes to the development of pneumonia, more often in young children. Disturbs metabolism (loss of glycogen reserves, fatty infiltration), and liver function, incl. detoxification. Induces microsomal enzymes of the cytochrome P450 system. Inhibits renal function and reduces diuresis due to the release of antidiuretic hormone and constriction of renal vessels. It is characterized by a small breadth of anesthetic action (therapeutic index does not exceed 1.5), relatively low organ toxicity (heart, liver, kidneys).

Ether anesthesia is characterized by good controllability and manageability. With the mask method, the effect develops slowly, the stage of surgical anesthesia occurs in 15-20 minutes (faster in young children). Awakening is gradual - (20-40 minutes). And in the subsequent period, depression of the central nervous system, drowsiness and analgesia persist for a long time (brain functions are completely restored after a few hours). Against the background of barbiturates and muscle relaxants, there is usually no stage of excitation (induction of anesthesia is not accompanied by suffocation, fear and other unpleasant sensations), muscle relaxation is potentiated and the severity of post-anesthesia depression is reduced.

Passes well through the BBB, easily diffuses to neurons through interneuronal fluid (low-molecular uncharged compound). It is unevenly distributed in organs: the level in the brain exceeds the concentration in the blood and other organs (the content in the medulla oblongata and spinal cord is approximately 50% higher than in the brain, due to the higher lipid content in the nerve conductors). Concentrations in the blood are: 10-25 mg% (analgesia stage), 25-70 mg% (excitation stage) and 80-110 mg% (surgical anesthesia stage). Passes through the placental barrier and creates high concentrations in the fetus. Deposited in the membranes of hepatocytes. Slightly (10-15%) biotransforms. It is quickly eliminated during the first few minutes, then excretion gradually slows down: 85-90% is excreted unchanged by the lungs, the rest by the kidneys. Medical ether, when applied locally to dental tissue, causes a “drying” effect (evaporates quickly at room temperature), exhibits weak antibacterial and local anesthetic activity (due to the irritant effect). The local irritating effect of ether on the skin can be used for distraction therapy (rubbing).

Application of the substance Diethyl ether

Ether for anesthesia: for inhalation anesthesia (mixed, combined, potentiated), incl. maintaining anesthesia (usually in a mixture with oxygen and dinitrogen oxide, against the background of muscle relaxants, induction of anesthesia with barbiturates, or dinitrogen oxide).

Medical ether: for the treatment of carious cavities and root canals of the tooth (preparation for filling).

Contraindications

Pulmonary tuberculosis, acute respiratory diseases, increased intracranial pressure, cardiovascular diseases with a significant increase in blood pressure, incl. hypertension, cardiac decompensation, severe liver and kidney diseases, general exhaustion, thyrotoxicosis, diabetes mellitus, state of agitation, severe acidosis, operations using electrosurgical instruments, incl. electrocoagulation.

Restrictions on use

Operations on the maxillofacial area (due to explosion hazard); use of mask anesthesia using only ether; childhood, pregnancy, breastfeeding.

Use during pregnancy and breastfeeding

With caution during pregnancy (adequate clinical studies have not been conducted) and during breastfeeding (data on excretion into human milk are not available).

Side effects of the substance Diethyl ether

From the respiratory system: hypersecretion of bronchial glands, cough, laryngo- and bronchospasm, disturbances in pulmonary ventilation, increased or depressed respiration, up to apnea, pneumonia and bronchopneumonia (in the postoperative period), diffusion hypoxia (against the background of impaired function of the lungs and heart or with prolonged use in high concentrations ).

From the cardiovascular system and blood (hematopoiesis, hemostasis): tachycardia or bradycardia, up to cardiac arrest; arrhythmia; hyper- or hypotension; collapse; bleeding

From the gastrointestinal tract: hypersalivation, nausea, vomiting, decreased tone and motility of the gastrointestinal tract, paralytic ileus (with long-term anesthesia), transient jaundice, changes in liver tests.

From the nervous system and sensory organs: agitation, motor activity, rarely - convulsions in children, drowsiness, depression (after surgery).

Others: metabolic acidosis, hypoalbuminemia, hypogammaglobulinemia, decreased urine output, albuminuria.

Interaction

Potentiates the effect of CNS depressants (mutually), the effect of non-depolarizing muscle relaxants, such as tubocurarine, and the hypotensive effect of beta-blockers. Reduces the hypoglycemic effect of insulin and sulfonylurea derivatives, oxytocin and other hormonal stimulants of the uterus. Incompatible with analeptics and psychostimulants. MAO inhibitors inhibit metabolism (increase the anesthetic effect); epinephrine and aminophylline increase the risk of arrhythmias, m-anticholinergics and antihistamines neutralize side effects, muscle relaxants reduce ether consumption by half.