Hexamine synthesis from Formaldehyde: Mechanism, Structure, Use
BP607P Medicinal Chemistry III Practical: I Preparation of drugs Sulphanilamide * 7-Hydroxy, 4-methyl coumarin * Chlorobutanol * Triphenyl imidazole * Tolbutamide * Hexamine II Assay of drugs Isonicotinic acid hydrazide * Chloroquine * Metronidazole * Dapsone * Chlorpheniramine maleate * Benzyl penicillin III Microwave irradiation technique Synthesis of Phenytoin by Microwave * Synthesis of Aspirin by Microwave IV Drawing structures and reactions using chem draw®
Aim
To prepare and submit hexamine from formaldehyde and calculate its Percentage Yield.
Principle
Hexamine is a heterocyclic organic compound (CH2)6N4. At the same time has a symmetrical tetrahedral cage-like structure. It is prepared by a condensation reaction between formaldehyde and ammonia.
Reaction
Chemical Required
Formaldehyde – 4.7 g
Ammonia Solution – 7 g
Procedure
Time needed: 2 hours
Synthesis of hexamine from formaldehyde
- Measure formaldehyde solution
Take 4.7g of 30% formaldehyde solution in a beaker
- Add ammonia solution
Add 7g of 24% ammonia solution until the solution becomes slightly alkaline
- Heat and cool the solution
Heat the mixture in a water bath for 5 minutes and then allowed it to stand for 15 minutes.
- Filter the solution
Filter the solution through the filtration membrane
- Evaporate the solution
Evaporate the solution on a direct flame using a china dish to a thick paste
- Formation of crystal
Collect the crystals and dry them
- Recrystallization
Carry out recrystallization with water or alcohol (colorless as well as odorless crystals)
Use
Urinary anti-infective agents as well as general antiinfective
Report
Hexamine was prepared and then submitted.
Report the following
e.g. Theoretical Yield:
e.g. Practical Yield:
then Percentage Yield:
Hexamine:
Hexamine, also known as methenamine or hexamethylenetetramine, is a versatile organic compound with the chemical formula (CH₂)₆N₄. It’s a white crystalline solid with a cage-like structure and several important properties:
Properties of Hexamine:
- Highly soluble in water and polar solvents: This makes it readily available for various applications.
- Neutral pH: It’s neither acidic nor basic, making it suitable for a wider range of uses.
- High melting point (280°C): It can withstand high temperatures without decomposition.
- Flammable: It burns cleanly and hot, making it a good fuel source.
- Formaldehyde releasing: In acidic environments, it releases formaldehyde, which has antibacterial and antiseptic properties.
Uses of Hexamine (Pharmaceutical):
Urinary Antiseptic: Hexamine is used as a urinary antiseptic in the treatment of urinary tract infections (UTIs). When ingested, it is converted to formaldehyde in the acidic environment of the urinary tract. Formaldehyde has antimicrobial properties, helping to kill bacteria and prevent the growth of pathogens in the urinary system.
Excipient in Tablet Formulations: Hexamine can be used as an excipient in tablet formulations. It is added to tablets as a binder or a disintegrant, helping to hold the tablet together and promote its dissolution when consumed.
Stabilizer in Drug Formulations: Hexamine can act as a stabilizer in certain drug formulations, particularly those prone to degradation or instability. It helps prevent chemical reactions, such as hydrolysis or oxidation, which could lead to the degradation of active pharmaceutical ingredients (APIs) or affect the overall stability of the formulation.
Microencapsulation: Hexamine has been utilized in microencapsulation processes for controlled drug release. It can be used as a core material or a crosslinking agent in the formation of microcapsules, allowing for the controlled release of drugs over an extended period.
Analytical Reagent: Hexamine is used as an analytical reagent in pharmaceutical laboratories. It can be employed in various chemical tests and assays to determine the presence or concentration of certain compounds or to assess the quality and purity of pharmaceutical products.
Hexamine structure
Hexamine, also known as methenamine or urotropin, has a unique and fascinating structure. Here’s a breakdown:
1. Cage-like Structure:
The most striking feature of hexamine is its cage-like structure. Imagine a tetrahedron (a 3D pyramid) with four corners and six edges. Each corner of this tetrahedron is occupied by a nitrogen atom, and each edge is formed by a methylene group (CH2).
2. Symmetrical Arrangement:
The nitrogen and methylene groups are arranged in a highly symmetrical way, giving the molecule its characteristic shape. This symmetry also contributes to many of hexamine’s interesting properties.
3. Similarity to Adamantane:
Hexamine’s cage-like structure is similar to that of adamantane, another interesting molecule. Adamantane is a diamondoid hydrocarbon known for its stability and resistance to chemicals.
4. Bond Angles and Distances:
The bond angles and distances between the atoms in hexamine are also noteworthy. The nitrogen atoms are connected by methylene groups at angles of approximately 109.5°, which is the ideal angle for sp³ hybridization. The carbon-nitrogen bonds have a length of about 1.47 Å, which is slightly longer than a typical single bond.
5. Internal Cavity:
The cage-like structure of hexamine creates an internal cavity that can be occupied by other molecules. This ability to form complexes with other molecules contributes to some of hexamine’s applications.
Hexamine is a crystalline organic compound with the chemical formula (CH₂)₆N₄. It is composed of carbon, hydrogen, and nitrogen atoms arranged in a hexagonal ring structure.
Hexamine is commonly synthesized through the reaction between formaldehyde and ammonia. The reaction takes place under controlled conditions, typically involving the use of acid catalysts.
The balanced chemical equation for hexamine synthesis is:
6 CH₂O + 4 NH₃ → (CH₂)₆N₄ + 6 H₂O
The key reactants are formaldehyde (CH₂O) and ammonia (NH₃). Formaldehyde is the primary building block for the hexamine molecule.
An acid catalyst, often sulfuric acid, is used to facilitate the reaction between formaldehyde and ammonia. It helps promote the formation of hexamine and increases the reaction rate.
Hexamine synthesis typically requires a temperature of around 80-100°C and a pressure of about 1-2 atm. These conditions are conducive to the formation of hexamine while ensuring safety and efficiency.
Hexamine synthesis is an exothermic reaction, meaning it releases heat during the chemical process.
Hexamine has various applications, including:
Medicinal use as a urinary antiseptic and treatment for urinary tract infections.
Industrial applications in the production of resins, rubber additives, and explosives.
Laboratory use as a reagent and buffer.
Fuel tablets for camping stoves and solid fuel heaters.
The purity of synthesized hexamine is typically determined through analysis methods such as chromatography or spectroscopy. Quality control measures are taken during the synthesis process to achieve the desired purity level.
Yes, hexamine can be synthesized on a laboratory scale using similar reaction principles as the industrial process. Proper safety measures and equipment are essential when conducting laboratory synthesis.
Yes, hexamine synthesis involves the use of formaldehyde and potentially hazardous acids. Proper ventilation, personal protective equipment, and adherence to safety protocols are crucial to prevent exposure to harmful substances.
Hexamine is typically stored in a dry and cool place, away from direct sunlight and moisture. Proper labeling and handling procedures should be followed to ensure safety.
Yes, the synthesis conditions and reactants can be modified to produce hexamine derivatives with specific properties suitable for different applications.
Research is ongoing to explore sustainable and environmentally friendly methods for hexamine synthesis, including the use of renewable resources as starting materials.
For some applications, there are alternatives to hexamine. However, its unique properties make it valuable for certain uses, such as in fuel tablets and medicinal formulations.
Understanding hexamine synthesis is important for its various applications and contributions to different industries. It involves controlled chemical reactions that result in a versatile compound with a wide range of practical uses.
Uses of urotropine
Main Uses:
- Solid fuel: Hexamine tablets are commonly used by campers and backpackers for their clean, hot burning.
- Urinary tract infections (UTIs): Hexamine releases formaldehyde in acidic urine, which helps kill bacteria causing UTIs. This use requires a doctor’s prescription.
- Industrial applications: Hexamine acts as a binder, curing agent, and component of resins in various industries like brake linings, rubber, and adhesives.
Other Uses:
- Corrosion inhibitor: Protects metals from rust and corrosion.
- Food preservative: Inhibits mold and bacterial growth in some foods.
- Textile industry: Used in certain dye processes.
- Vulcanization process: Aids in vulcanizing rubber.
- Histology stain: Used in the Grocott methenamine silver stain to identify fungi.
Important Points:
- Urotropine/hexamine is a controlled substance in some countries due to its potential use in explosives.
- Always consult a healthcare professional before using urotropine for medicinal purposes.
- Urotropine dust can irritate the eyes and respiratory system; handle with care.
