A method for producing hexamine is described, which consists of the catalytic oxidation of methanol into formaldehyde by atmospheric oxygen at a temperature of 650-710 o C, the interaction of formaldehyde with ammonia in a reactor filled with mother liquor, followed by precipitation of the resulting crystals, while formaldehyde is additionally introduced into the reactor in the form of aqueous or aqueous -methanol solution taken in an amount of 5-50 wt.% of the formaldehyde supplied as part of the contact gases, and the methanol:ammonia mass ratio is maintained equal to 1:(0.35-0.5), respectively. 1 table

The invention relates to technology for the production of hexamethylenetetramine (urotropine) and can be used in the chemical industry for the synthesis of various brands of condensation resins, as well as in the pharmaceutical industry. There is a known method for the synthesis of hexamethylenetetramine (HMTA), which includes the interaction in a synthesis reactor of an aqueous or water-methanol solution of formaldehyde (formalin) with a concentration of 37-42 wt.% with gaseous ammonia to form a dilute aqueous solution of HMTA, evaporative crystallization of technical hexamine in a vacuum crystallizer, carried out by supplying the required amount of heat to the heating chamber of the apparatus [Czechoslovakia Patent 230110 dated May 1, 1986]. The disadvantage of this method is the need to carry out the synthesis and crystallization process in separate apparatuses, the low power of the synthesis reactor, and the heat consumption for evaporation of a dilute solution of HMTA. The technical result to which the present invention is aimed is to increase the power of the HMTA synthesis reactor and reduce energy costs. Specified technical result is achieved by a method for producing hexamethylenetetramine (urotropine), which consists in the catalytic oxidation of methanol into formaldehyde by atmospheric oxygen at a temperature of 650-710 o C, the interaction of formaldehyde with ammonia in a reactor filled with mother liquor, followed by precipitation of the resulting crystals, while formaldehyde is additionally introduced into the reactor in the form an aqueous or water-methanol solution taken in an amount of 5-50 wt.% of the formaldehyde supplied as part of the contact gases, and the mass ratio of methanol: ammonia is maintained equal to 1: (0.35-0.5), respectively. The established amount of additionally introduced aqueous or water-methanol solution of formaldehyde depends on the required increase in power, the concentration of the supplied formaldehyde solution (35-60 wt.%), the minimum possible amount of reflux, providing the required composition of the exhaust gases. The introduction of formaldehyde in an amount of less than 5% does not significantly increase power and has virtually no effect on the operating mode of the HMTA synthesis reactor. The introduction of formaldehyde in an amount of more than 50% does not allow, due to the heat released during the interaction of ammonia with formaldehyde in the contact gases, to ensure the evaporative crystallization of a dilute solution of HMTA and the evaporation of a minimum amount of reflux for the required purification of exhaust gases. An example of the method. Rectified methanol in an amount of 3.5 t/hour is diluted with demineralized water to a concentration of 60-68 wt.% and sent to an alcohol evaporator. Air in an amount of 3800 nm 3 /hour, bubbling in an alcohol evaporator, is saturated with vapors of methanol and water. The resulting alcohol-air mixture, heated to 80-100 o C, enters the contact apparatus, where the oxidation and dehydrogenation reactions of methanol CH 3 OH + 1/2O 2 --> CH 3 O + H take place on a silver catalyst at a temperature of 650-710 o C 2 O+Q 1 CH 3 OH-->CH 2 O+H 2 -Q 2 From the contact zone, a gas mixture containing carbon dioxide, carbon monoxide, hydrogen, formaldehyde, water, methane, unreacted methanol and oxygen, nitrogen is cooled to 120 o C and under vacuum enters a reactor filled with mother liquor. At the same time, contact gases containing formaldehyde, an aqueous or water-methanol solution of formaldehyde in an amount of 0.5-3.5 m 3 /hour and gaseous ammonia in an amount of 1.216-1.721 t/hour are fed into the reactor, where at a temperature of 72-83 o C and vacuum 460 mm Hg. HMTA 6CH 2 O+4NH 3 -->(CH 2) 6 N 4 +6H 2 O+Q 3 is formed. Mass ratio of methanol: ammonia = 1: (0.35-0.5). The supply of reflux to the bubble plates in the upper part of the reactor is maintained automatically in the range of 1.0-2.35 c/h, depending on the level of the mother liquor in the apparatus. The resulting HMTA is isolated in the form of crystals from saturated solution. The suspension from the bottom of the reactor enters the turbidity chamber, where HMTA crystals precipitate. The pulp (condensed suspension) from the bottom of the turbidity plant enters a centrifuge to separate HMTA crystals, including those from formaldehyde in the contact gases, from the formaldehyde solution. To clarify the above, we provide examples of the implementation of the proposed method in the stated modes. The conditions and results of implementing the claimed method are presented in the table. From the analysis of experimental data it follows that the proposed method makes it possible to increase the power of the HMTA synthesis reactor by 4.8-48%, to combine the synthesis and crystallization of HMTA from ammonia and formaldehyde in the composition of contact gases with the synthesis and evaporative crystallization of HMTA from ammonia and aqueous or water-methanol formaldehyde solution, reduce energy costs through the rational use of excess heat generated in the synthesis reactor.

Claim

A method for producing hexamethylenetetramine (urotropine), including the catalytic oxidation of methanol into formaldehyde by atmospheric oxygen at a temperature of 650-710 o C, the interaction of formaldehyde with ammonia in a reactor filled with mother liquor, followed by precipitation of the resulting crystals, characterized in that formaldehyde is additionally introduced into the reactor in the form an aqueous or water-methanol solution taken in an amount of 5-50 wt.% of the formaldehyde supplied as part of the contact gases, and the mass ratio of methanol: ammonia is maintained equal to 1: (0.35-0.5), respectively.

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IN modern world Absolutely every person has at least once suffered from any infectious disease caused by a certain pathogenic microorganism. One of the most common localizations of bacteria in human body is the urinary system. When these organs are damaged, unpleasant symptoms occur such as:

If one or more of the listed symptoms occurs, you must immediately contact a urologist, who will prescribe the appropriate tests and provide the necessary treatment.

For example, Urotropin is often used in such cases. What kind of drug this is, what its formula is, and what is included in Urotropin will be discussed in detail below.

Description

The drug, which is produced by the Russian plant OJSC Metafrax, located in the Perm region, the city of Gubakha, has a substance called methenamine as its main active ingredient.

Externally, it is a powder consisting of rhombic crystals white, and also has a slight specific smell and sweet taste.

A characteristic feature of the drug is its rich history of use in medicine. It dates back about a hundred years, that is, for about a century the drug has been helping to effectively cope with some ailments.

Formula

"Urotropin" by its chemical nature belongs to the class of polycyclic amines. This organic matter, which contain several benzene rings, as well as nitrogen atoms.

Full name chemical formula"Hurotropine" is 1,3,5,7-tetraazotricyclodecane.

If we talk about how the nitrogen atoms included in the drug molecule are located, their arrangement is as follows.

This is called the structural formula of "Herotropin", looking at which you can clearly see how the nitrogen atoms are connected to each other by carbon bonds.

However, it often happens that such spellings of a substance are not always convenient. Therefore, the short formula of “Urotropin” is often used - C 6 H 12 N 4.

Thus, methenamine consists of carbon and hydrogen atoms. In addition, the formula of "Urotropin" includes four more nitrogen atoms.

Components of the drug

Most often in medical and veterinary practice, an injection solution is used. Next, we will analyze in more detail the composition of "Urotropin".

Instructions for use indicate what it contains:

• Methenamine is the active substance.
• Water for injection - as a solvent.

Release forms

On the pharmaceutical market the drug is presented in several forms:

1. Injection solution for intravenous administration, having a concentration of 40%.
2. Powder, which is packaged in bags.
3. Tablets of 0.25 and 0.5 g.

Indications for use

"Urotropin" is a universal drug. In addition, it has a fairly diverse list of conditions for which its use is relevant. These include:

• Infectious diseases urinary system (cystitis, pyelitis, pyelonephritis).
• Hyperhidrosis. The drug is effectively used to eliminate sweating of the armpits, palms and feet.
• "Urotropin" is widely used in veterinary medicine. Possessing an anti-inflammatory effect, it is able to quickly eliminate diseases of the kidneys, bladder, and mammary glands in cattle.

Contraindications for use

Like any other drug, Urotropin has a number of contraindications, namely:

• Children's age up to 6 years.
• Individual intolerance to the drug.
• Kidney or liver failure.
• Dehydrated state of the body.

Use during pregnancy and breastfeeding

There is no scientifically proven data on the safety of use by women during this period, so it is better for this group of people to refrain from treatment with Urotropin.

Side effects

In some cases, "Urotropin" can have a negative effect on the body, especially on the function of the kidneys and bladder.

The main unwanted side effects are as follows:

• An allergic reaction in the form of an itchy rash on the skin. This symptom disappears quickly and without a trace after stopping the drug.
• Hematuria is the appearance of blood in the urine.
• Proteinuria is the appearance of protein in the urine.
• Frequent urination.

If such negative reactions occur, you must immediately consult a doctor in order to decide whether to stop treatment with Urotropin or adjust its dosage.

Storage conditions

The drug should be stored in a dry place, at a temperature not exceeding 25 degrees, away from sunlight and out of reach for children.

Conditions for dispensing from pharmacies

"Urotropin" is a prescription drug, therefore free access he can't be found. When selling it, the pharmacist (or pharmacist) will definitely ask for a prescription form, which must be prescribed by the attending physician.

Cost of medicine

"Urotropin" (formula C 6 H 12 N 4) is a cheap drug. Its cost does not exceed 100 rubles per package.

Conclusion

"Urotropin" is a unique drug with a wide spectrum of action.

The main advantages of the drug are its low cost, as well as high efficiency, time-tested.

The disadvantage is the presence of a whole list of side effects, due to which some patients have to stop the course of treatment with Urotropin and again contact the doctor to change the medication.

It should be remembered that the product can negatively affect the body, so it is unacceptable to use it independently without a doctor’s prescription.

Hexamethylenetetramine (Urotropin)

Preparation of hexamethylenetetramine

Hexamethylenetetramine is a product of the reaction of a solution of formaldehyde with ammonia. It was first obtained by A. M. Butlerov (1860), but only 35 years after its discovery it began to be used in medicine.

The raw materials for the production of hexamethylenetetramine are a 40% solution of formaldehyde in water and ammonia water. 25% ammonia water is added to the formaldehyde solution, the mixture is stirred and the temperature is maintained within 40-50 °C.

After the reaction is complete, the reaction mixture should be alkaline and smell of ammonia. Activated carbon is added to the mixture, filtered, and the filtrate is evaporated in vacuum to a paste. When cooled, crystals of hexamethylenetetramine crystallize. They are sucked off, washed and dried at a temperature of 30-35 °C. The resulting hexamethylenetetramine is recrystallized from alcohol.

Hexamethylenetetramine is a white crystalline powder, very hygroscopic. Has no smell. The taste is pungent, sweet at first, then bitter. The drug is highly soluble in water and alcohol, soluble in chloroform, and almost insoluble in ether. Aqueous solutions hexamethylenetetramine have a slightly alkaline reaction. When heated, they evaporate without melting.

Pharmacological properties of hexamethylenetetramine

Synonyms:

Urotropine, Aminoform, Cystamine, Cystogen, Formamin, Hexamethylentetramin, Hexamina, Methenamine, Metramine, Urisol, Urotropinum, etc.

Colorless crystals or white crystalline powder with a pungent and sweet, and then bitter taste, odorless. Easily soluble in water (1:1.5) and alcohol (1:10). When heated, it evaporates without melting. Burns with a pale flame. Aqueous solutions have an alkaline reaction (pH of 40% solution 7.8 - 8.2).

For intravenous administration, the solution is prepared aseptically.

Pharmacological properties:

The preparation of hexamethylenetetramine was the first experience (1899) in the creation of a medicinal substance, which is currently called a prodrug (Phenyl salicylate). When hexamethylenetetramine breaks down in the body (in an acidic environment), formaldehyde is released, which has an antiseptic property when excreted in the urine.

Hexamethylenetetramine is used as an antiseptic for infectious processes in the urinary tract (cystitis, pyelitis). With an alkaline reaction of urine, the elimination of formaldehyde does not occur and no therapeutic effect is observed. In these cases, substances are prescribed that shift the urine reaction to the acidic side (Ammonium chloride). To prevent the breakdown of hexamethylenetetramine in the stomach, it is prescribed on an empty stomach. If necessary, a solution of hexamethylenetetramine is administered intravenously.

Indications for the use of hexamethylenetetramine also include cholecystitis and cholangitis, allergic skin diseases (urticaria, erythema multiforme, etc.), eye diseases (iridocyclitis, keratitis, etc.). The drug is also used for meningitis, encephalitis, and arachnoiditis.

Currently, due to the availability of more effective agents, hexamethylenetetramine is not widely used.

Application:

Prescribed orally in tablets and solutions for adults at 0.5 - 1.0 g per dose, for children - 0.1 - 0.5 g; taken several times a day. 5-10 ml of a 40% solution is injected into a vein.

Side effects: Hexamethylenetetramine can cause irritation of the renal parenchyma and in some cases contribute to the spread of the disease process in pyelitis. If signs of kidney irritation are detected, stop taking the drug.

Release form: powder; tablets of 0.25 and 0.5 g; 40% solution in ampoules of 5 and 10 ml.

Storage: in a well-closed container; solutions - at a temperature not higher than +20 C.

Hexamethylenetetramine is an integral part of the combined tablets “Kaltsex” and “Urobesal”. The previously produced Urosal tablets, which contained 0.3 g each of hexamethylenetetramine and phenyl salicylate, were excluded from the range of medicines.

The drug Urotropine is a synthetic antiseptic that is widely used in modern medicine. The second name is Hexamethylenetetramine. This medication has several dosage forms and acts systemically in the body. Before starting a therapeutic course, you must individually consult with your doctor.

Composition and release form

The drug Urotropin is a diuretic (diuretic) developed on the basis of methenamine. The medicine is produced in several release forms:

1. White powder without a specific odor with a sweetish-burning taste. Quickly dissolves in water and alcohol. The medicine is packaged in special bags.
2. A transparent solution for injection, which is poured into ampoules of 10, 20 and 100 ml, instructions for use are included.
3. White tablets with a bitter taste, dosage 0.25 and 0.5 g, quickly soluble in water. The medicine is distributed into glass test tubes and packaged in 10 pieces.

A stable therapeutic effect is provided by synthetic components from chemical composition and their interaction. The active component of the drug is methenamine. The excipient for the solution is water for injection. For other forms of release of Hexamine, the concentration of the active component is different, detailed description contained in the instructions.

Pharmacodynamics and pharmacokinetics

Detailed instructions for use of Urotropin describe the principle of action of the medication in the patient’s body. The active substance is broken down in an acidic environment, releasing active formaldehyde. A medication with antimicrobial and anti-inflammatory properties destroys bacteria that cause urinary tract diseases and suppresses inflammatory processes with a high content of acidic tissue breakdown products. Hexamine, having a diuretic effect, increases the permeability of cell membranes and promotes the elimination of toxins during intoxication.

When administered orally or by injection, Urotropin active substances are productively absorbed from the digestive tract, penetrate into the bloodstream, and are evenly distributed throughout the tissues. The metabolic process with the release of inactive metabolites occurs in the liver. The half-life of the active substances is 6–12 hours. Inactive metabolites are excreted by the kidneys and urine.

Indications for use

According to the instructions for use, Urotropin is recommended for infectious and inflammatory processes of the urinary tract and kidneys, for example, for progressive cystitis, pyelitis. Among other indications for use, doctors identify increased sweating of the armpits, palms, and legs. The drug is prescribed independently or as part of complex therapy. Veterinarians recommend this medication for similar diseases for the treatment of cattle.

Directions for use and dosage

The rules for using the medication depend on the prescribed form of release. Medicine needs to be used full course, and do not self-medicate. In case of infectious and inflammatory processes of the urinary system, Urotropin is recommended to be taken orally; in case of impaired functioning of the sebaceous glands, it is recommended to be taken externally, directly to the site of the pathology.

Urotropine for sweaty feet

If the purchased antiperspirant only temporarily eliminates sweating and unpleasant odor of the lower extremities, it is recommended to use a solution of Hexamine. This medication not only removes unpleasant odors and discomfort, but also effectively destroys bacteria and fungi, as a factor that provokes increased sweating. According to the instructions for use, during treatment the sequence of patient actions is as follows:

1. The procedure is recommended to be carried out in the evening, preferably before bedtime.
2. The first step in case of hyperhidrosis is to thoroughly wash and dry your feet and the space between your toes.
3. Using a cotton pad, you need to thoroughly treat your feet with the medicine, put on socks made of natural material and go to bed.
4. Start the morning by rinsing your feet with warm water; it is additionally recommended to use talc.
5. Before starting treatment with this medication, it is necessary to get rid of fungal infections, open wounds, suppurations, and cracks using medicinal methods.
6. When treating sweaty feet, you need to keep your shoes clean and periodically treat them with local antiseptics in the form of sprays.
7. With the help of this local antiseptic, you can get rid of excessive sweating of the feet for a period of 15–30 days.

Urotropine for armpit sweating

With such a piquant health problem, the rules for using Hexamine are identical, but the drug is used much less frequently. Before applying the medicinal composition in the form of powder or liquid, you need to shave, wash, and dry your armpits. It is necessary to make sure that there are no abrasions, open wounds and suppuration at the sites of pathology. Applying the medicinal composition to the armpit area is allowed once every 2 weeks. Afterwards, put on underwear made from natural material and go to bed. Additionally, it is recommended to use soap with an antimicrobial effect.

special instructions

The drug Urotropin at the beginning of the course can provoke the development of hematuria (blood in the urine) or proteinuria (detection of protein in the urine). In such clinical cases further treatment you need to stop and choose a gentle analogue of urotropine. The instructions for use provide valuable information for patients:

1. Since alcohol-containing substances increase the acidity of urine, it is better to avoid drinking alcohol during the period of treatment, even in small dosages.
2. Treatment for excessive sweating should have A complex approach: in addition to Hexamine, it is important to regularly change underwear made from natural materials, observe basic rules of personal hygiene, and disinfect shoes.
3. To avoid side effects, it is not recommended to use the medicine too often (the optimal dose depends on individual characteristics each clinical case).
4. Since the use of a concentrate excessively dries out the skin, it is recommended to pre-dilute the Hexamine solution with water.
5. Before using Hexamethylenetetramine, the first step is to get rid of a pathogenic fungus or other infectious process.
6. If a concentrated drug comes into contact with the pathology site, a feeling of pain, internal discomfort, and irritation is possible.
7. If there are erosions, cracks, or open wounds on the skin, before using Urotropin, it is recommended to cure the underlying disease, for example, for 5-6 days you should perform medicinal baths with a weak solution of potassium permanganate.

Hexamine for animals

In veterinary practice, it is an effective drug with a pronounced antitoxic, antimicrobial and diuretic effect. Hexamine is recommended for the treatment of inflammation in the kidneys, bladder and urinary tract in large domestic animals. If you follow the recommendations of a specialist, you can as soon as possible destroy the infection, normalize urination.

Drug interactions

In case of infectious processes of the urinary system and increased sweating of the legs and armpits, complex drug therapy is necessary. Information about drug interactions is not described in the instructions for use.

Side effects and overdose

Hexamine is well tolerated by the body, especially when used externally. In isolated clinical cases, side effects develop, which are described in detail in the instructions for use:

• frequent urination;
• proteinuria;
• hematuria;
• skin rash;
• allergic reactions.

If the prescribed daily doses are systematically exceeded, the patient complains of increased side effects. He is bothered by burning, itching and irritation of the urinary tract and urethra. Dysuric manifestations, hematuria, and increased allergic reactions cannot be excluded. Treatment is symptomatic and begins with adjusting the daily dosage of the medication. There is no specific antidote.

Contraindications

Hexamine is not recommended for use in hypersensitivity body to the active ingredients of the drug. This concludes the list of absolute medical contraindications. During pregnancy and lactation, before starting the course, you must individually consult with your doctor.

Terms of sale and storage

The drug is a prescription drug, so not everyone can buy it at the pharmacy. According to the instructions for use, the medicine must be stored in a dry, dark, cool place, inaccessible to small children. It is important to avoid exposure to sunlight. The optimal temperature is up to 23 degrees. The shelf life is 2 years, after which the medication must be disposed of.

Hexamethylenetetramine (urotropine) was first obtained by Butlerov in 1860 by the action of ammonia on polyoxymethylene.

Hexamethylenetetramine has the empirical formula (CH2)6N4; its molecular weight is 140.14; structural formula

Hexamine crystallizes from alcohol in the form of colorless shiny rhombohedrons, sublimes in a vacuum almost without decomposition, and dissolves in water with the release of heat and the formation of a hexahydrate. In warm water, methenamine is less soluble than in cold water, and in ethyl alcohol, on the contrary, methenamine is more soluble in hot water than in cold water.

Hexamine has a very high reactivity and forms many salts, for example, CeH^NUHCl, dini - waste C 6HI 2N42 HN 03, perchlorate C6H12N4HCIO3, etc.; with phenols gives addition products. Once set on fire, it burns with a calm, non-smoking flame; flammable but not explosive.

In medicine, methenamine is used in the treatment of bacterial diseases, urinary tract diseases, in the treatment of influenza and other diseases. It finds use in the canning of certain foods; Thus, when canning caviar, it is used in a mixture with citric acid and sodium benzoate.

Together with zinc oxide, methenamine is an accelerator of rubber vulcanization; in large quantities it is used for the preparation of artificial resins and for other purposes.

The raw materials for the production of methenamine are formaldehyde, ammonia, ethyl alcohol and activated carbon.

The formation reaction of methenamine consists of combining six molecules of formaldehyde with four molecules of ammonia, releasing six molecules of water:

6NSON - 4NH, = (CH,),. N4 v 6Н,0. (205)

The technological process diagram for the production of hexamine is shown in Fig. 122.

Formalin to be processed is pumped into a collection tank 2, From where it flows by gravity into reactor 3; here through the bar -

Rice. 122. Scheme of the technological process for the production of hexamine: 1- Pressure tank for 257g ammonia, 2-pressure tank for formaldehyde, 3 -reactor,Behind- Reverse capacitor, 4 -pump, 5 , 6, 7 - settling tanks, 8 And 9 -filters, 10 -evaporator, 11 - Nutsch filter, 12 -receiver, 13 -pump, 14 -centrifuge, 15- Barrel for methenamine

The boiler, located in the lower part of the reactor, supplies a 25% ammonia solution in an equimolecular amount from pressure tank 1.

Reactor 3 is a closed iron cylinder equipped with a stirrer and a reflux condenser. Behind.

Since the process of formation of hexamine is an exothermic process, in order to maintain the required temperature, the mixture in the reactor is cooled, for which a coil is placed in it through which cooling water is passed.

After the reaction is completed, the liquid is pumped over 4 To settling tanks 5, 6 i 7. The settled solution of hexamine enters through pumice filters 8 And 9 into the evaporator 10 with steam jacket.

After evaporation, the solution flows by gravity into the Nutsch filter. 11, from which hexamine crystals are manually transferred into a centrifuge 14. Extracted methenamine is unloaded into barrels 15.

Mother liquor from a suction filter 11 goes to the receiver 12, and from it, by pump 13 Pacraqp is again sent for evaporation into the evaporator cube 10.

As a result of such processing, technical urotropine is obtained. To obtain a medical product, technical urotropine is dissolved in alcohol and crystallized from it. The resulting “crystals are dried and sorted by crystal size using sieves.

For one ton finished product 7.6 tons of formaldehyde consumed40% and 2.48 tons of ammonia 35%.