HEXAMETHYLENE TETRAMINE (HEKZAMETLEN TETRAMN)

HEXAMETHYLENE TETRAMINE/ HEKZAMETLEN TETRAMN

CAS NO:100-97-0

EC NO:202-905-8

Synonyms:

HMTA; E239; Carin; Uramin; Urisol; FORMIN; Hexa B; ekagomh; Heterin; Hexamin; 1,3,5,7- Tetraazaadamantane; Ammonioformaldehyde; Aceto HMT; Aminoform; Ammoform; Cystamin; Cystogen; Esametilentetramina (Italian); Formamine; Formin; Hexaform; Hexamethylenamine; Urotropin; Hexamethyleneamine; Hexamethylenetetraamine; Hexamethylentetramin (German); Hexamethylentetramine; Hexilmethylenamine; HMT; Methamin; Methenamine; Resotropin; Uritone; Urotropine; Esametilentetramina (Italian); 1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane; HEKZAMETLEN TETRAMN, HEXAMETLEN TETRAMN; hekzametilen tetramin; heksametilen tetramin; hexamn; hexamin; hexamine; hexamne; HEXAMIN; HEXAMN; HEXAMNE; HEXAMINE; HMTA; E239; Carin; Uramin; Urisol; FORMIN; Hexa B; ekagomh; Heterin; Hexamin; 1,3,5,7- Tetraazaadamantane; Ammonioformaldehyde; Aceto HMT; Aminoform; Ammoform; Cystamin; Cystogen; Esametilentetramina (Italian); Formamine; Formin; Hexaform; Hexamethylenamine; Urotropin; Hexamethyleneamine; Hexamethylenetetraamine; Hexamethylentetramin (German); Hexamethylentetramine; Hexilmethylenamine; HMT; Methamin; Methenamine; Resotropin; Uritone; Urotropine; Esametilentetramina (Italian); 1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane; HEKZAMETLEN TETRAMN, HEXAMETLEN TETRAMN; hekzametilen tetramin; heksametilen tetramin; hexamn; hexamin; hexamine; hexamne; HEXAMIN; HEXAMN; HEXAMNE; HEXAMINE; heksametilen, tetramin; hekzametilen, tetramin.; Hexamethylene tetramin; Hexamethylene tetramine; Hexamethylene tetramine;Hexa methylenetetramine ;Hexa methylene tetramine;Hexa methylene tetra amine; Hexamethylenetetramine; methenamine; methen amine; HEKZAMETLEN TETRAMN ;Hekza metilen Tetramin ; Hekzametilen Tetra amin; Hekza metilen Tetra amin ;Hekzametilen Tetramine; Hekza metilen Tetramine; Hekza metilen Tetra amine; méthénamine ; methenamin; methenamine; metenamin; meten amine;Hexamethylene tetramine;Hexa methylenetetramine ;Hexa methylene tetramine;Hexa methylene tetra amine; Hexamethylenetetramine; methenamine; methen amine; HEKZAMETLEN TETRAMN ;Hekza metilen Tetramin ; Hekzametilen Tetra amin; Hekza metilen Tetra amin ;Hekzametilen Hexamethylene tetramine; Hexamethylene tetramine;Hexa methylenetetramine ;Hexa methylene tetramine;Hexa methylene tetra amine; Hexamethylenetetramine; methenamine; methen amine; HEKZAMETLEN TETRAMN ;Hekza metilen Tetramin ; Hekzametilen Tetra amin; Hekza metilen Tetra amin ;Hekzametilen Tetramine; Hekza metilen Tetramine; Hekza metilen Tetra amine; méthénamine ; methenamin; methenamine; metenamin; meten amine;Hexamethylene tetramine; Hexamethylene tetramine;Hexa methylenetetramine ;Hexa methylene tetramine;Hexa methylene tetra amine; Hexamethylenetetramine; methenamine; methen amine; HEKZAMETLEN TETRAMN ;Hekza metilen Tetramin ; Hekzametilen Tetra amin; Hekza metilen Tetra amin ;Hekzametilen Tetramine; Hekza metilen Tetramine; Hekza metilen Tetra amine; méthénamine ; methenamin; methenamine; metenamin; meten amine; ; Tetramine; Hekza metilen Tetramine; Hekza metilen Tetra amine; méthénamine ; methenamin; methenamine; metenamin; meten amine; HEKZAMETLEN TETRAMN ; Hekzametilen Tetramin; heksametilen, tetramin; hekzametilen, tetramin.; Hexamethylene tetramin; Hexamethylene tetramine; Hexamethylene tetramine;Hexa methylenetetramine ;Hexa methylene tetramine;Hexa methylene tetra amine; Hexamethylenetetramine; methenamine; methen amine; HEKZAMETLEN TETRAMN ;Hekza metilen Tetramin ; Hekzametilen Tetra amin; Hekza metilen Tetra amin ;Hekzametilen Tetramine; Hekza metilen Tetramine; Hekza metilen Tetra amine; méthénamine ; methenamin; methenamine; metenamin; meten amine;Hexamethylene tetramine;Hexa methylenetetramine ;Hexa methylene tetramine;Hexa methylene tetra amine; Hexamethylenetetramine; methenamine; methen amine; HEKZAMETLEN TETRAMN ;Hekza metilen Tetramin ; Hekzametilen Tetra amin; Hekza metilen Tetra amin ;Hekzametilen Hexamethylene tetramine; Hexamethylene tetramine;Hexa methylenetetramine ;Hexa methylene tetramine;Hexa methylene tetra amine; Hexamethylenetetramine; methenamine; methen amine; HEKZAMETLEN TETRAMN ;Hekza metilen Tetramin ; Hekzametilen Tetra amin; Hekza metilen Tetra amin ;Hekzametilen Tetramine; Hekza metilen Tetramine; Hekza metilen Tetra amine; méthénamine ; methenamin; methenamine; metenamin; meten amine;Hexamethylene tetramine; Hexamethylene tetramine;Hexa methylenetetramine ;Hexa methylene tetramine;Hexa methylene tetra amine; Hexamethylenetetramine; methenamine; methen amine; HEKZAMETLEN TETRAMN ;Hekza metilen Tetramin ; Hekzametilen Tetra amin; Hekza metilen Tetra amin ;Hekzametilen Tetramine; Hekza metilen Tetramine; Hekza metilen Tetra amine; méthénamine ; methenamin; methenamine; metenamin; meten amine; ; Tetramine; Hekza metilen Tetramine; Hekza metilen Tetra amine; méthénamine ; methenamin; methenamine; metenamin; meten amine; HEKZAMETLEN TETRAMN ; Hekzametilen Tetramin

HEXAMETHYLENE TETRAMNE

Hexamethylene tetramine

Hexamine.svg

Hexamine-3D-balls.png

Names

IUPAC name

1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane

Other names

Hexamine; Hexamethylene tetramine;

Urotropine; 1,3,5,7- tetraazaadamantane, Formin, Aminoform

Identifiers of Hexamethylene tetramine

CAS Number of Hexamethylene tetramine

100-97-0 ☑

3D model (JSmol)

Interactive image

Beilstein Reference 2018

ChEBI

CHEBI of Hexamethylene tetramine:6824 ☑

ChEMBL

ChEMBL1201270 ☑

ChemSpider

3959 ☑

DrugBank

DB06799

ECHA InfoCard 100.002.642

EC Number of Hexamethylene tetramine

202-905-8

E number of Hexamethylene tetramine E239 (preservatives)

Gmelin Reference of Hexamethylene tetramine 26964

KEGG

D00393 ☑

MeSH of Hexamethylene tetramine Hexamethylene tetramine

PubChem CID

4101

UNII

J50OIX95QV ☑

CompTox Dashboard (EPA)

DTXSID6020692 Edit this at Wikidata

InChI[show] of Hexamethylene tetramine

SMILES[show] of Hexamethylene tetramine

Properties of Hexamethylene tetramine

Chemical formula of Hexamethylene tetramine C6H12N4

Molar mass of Hexamethylene tetramine 140.186 g/mol

Appearance of Hexamethylene tetramine White crystalline solid

Odor of Hexamethylene tetramine Fishy, ammonia like

Density of Hexamethylene tetramine 1.33 g/cm3 (at 20 °C)

Melting point of Hexamethylene tetramine 280 °C (536 °F; 553 K) (sublimes)

Solubility of Hexamethylene tetramine in water 85.3 g/100 mL

Solubility Soluble in chloroform, methanol, ethanol, acetone, benzene, xylene, ether

Solubility of Hexamethylene tetramine in chloroform 13.4 g/100 g (20 °C)

Solubility of Hexamethylene tetramine in methanol 7.25 g/100 g (20 °C)

Solubility of Hexamethylene tetramine in ethanol 2.89 g/100 g (20 °C)

Solubility of Hexamethylene tetramine in acetone 0.65 g/100 g (20 °C)

Solubility of Hexamethylene tetramine in benzene 0.23 g/100 g (20 °C)

Acidity of Hexamethylene tetramine(pKa) 4.89[1]

Pharmacology of Hexamethylene tetramine

ATC code J01XX05 (WHO)

Hazards

Main hazards Highly combustible, harmful

GHS pictograms GHS02: Flammable GHS07: Harmful

GHS Signal word Warning

GHS hazard statements H228, H317

GHS precautionary statements P210, P240, P241, P261, P272, P280, P302+352, P321, P333+313, P363, P370+378, P501

NFPA 704 (fire diamond)

NFPA 704 four-colored diamond

321

Flash point 250 °C (482 °F; 523 K)

Autoignition

temperature 410 °C (770 °F; 683 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

☒ verify (what is ☑☒ ?)

Infobox references

Hexamethylene tetramine or Hexamethylene tetramine, also known as hexamine or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. Hexamethylene tetramine has a cage-like structure similar to adamantane. It is useful in the synthesis of other chemical compounds, e.g., plastics, pharmaceuticals, rubber additives. It sublimes in vacuum at 280 °C.

Synthesis, structure, reactivity

Hexamethylene tetramine was discovered by Aleksandr Butlerov in 1859.[2][3] It is prepared industrially by combining formaldehyde and ammonia.[4] The reaction can be conducted in gas phase and in solution.

Synthesis Hexamethylene tetramine

The molecule has a symmetric tetrahedral cage-like structure, similar to adamantane, whose four “corners” are nitrogen atoms and “edges” are methylene bridges. Although the molecular shape defines a cage, no void space is available at the interior for binding other atoms or molecules, unlike crown ethers or larger cryptand structures.

The molecule behaves like an amine base, undergoing protonation and N-alkylation (e.g. Quaternium-15).

Applications of Hexamethylene tetramine

The dominant use of Hexamethylene tetramine is in the production of powdery or liquid preparations of phenolic resins and phenolic resin moulding compounds, where it is added as a hardening component. These products are used as binders, e.g. in brake and clutch linings, abrasive products, non-woven textiles, formed parts produced by moulding processes, and fireproof materials.[4]

Hexamethylene tetramine has been proposed that Hexamethylene tetramine could work as a molecular building block for self-assembled molecular crystals.[5][6]

Medical uses of Hexamethylene tetramine

As the mandelic acid salt (generic Hexamethylene tetramine mandelate, USP[7]) it is used for the treatment of urinary tract infection. It decomposes at an acidic pH to form formaldehyde and ammonia, and the formaldehyde is bactericidal; the mandelic acid adds to this effect. Urinary acidity is typically ensured by co-administering vitamin C (ascorbic acid) or ammonium chloride. Its use had temporarily been reduced in the late 1990s, due to adverse effects, particularly chemically-induced hemorrhagic cystitis in overdose,[8] but its use has now been re-approved because of the prevalence of antibiotic resistance to more commonly used drugs. This drug is particularly suitable for long-term prophylactic treatment of urinary tract infection, because bacteria do not develop resistance to formaldehyde. It should not be used in the presence of chronic kidney disease.

Hexamethylene tetramine in the form of cream and spray is successfully used for treatment of excessive sweating and concomitant odor.[medical citation needed]

Histological stains

Hexamethylene tetramine silver stains are used for staining in histology, including the following types:

Grocott’s Hexamethylene tetramine silver stain, used widely as a screen for fungal organisms.

Jones’ stain, a Hexamethylene tetramine silver-Periodic acid-Schiff that stains for basement membrane, availing to view the “spiked” Glomerular basement membrane associated with membranous glomerulonephritis.

Solid fuel

Together with 1,3,5-trioxane, Hexamethylene tetramine is a component of hexamine fuel tablets used by campers, hobbyists, the military and relief organizations for heating camping food or military rations. It burns smokelessly, has a high energy density of 30.0 megajoules per kilogram (MJ/kg), does not liquify while burning, and leaves no ashes, although its fumes are toxic.

Standardized 0.149 g tablets of Hexamethylene tetramine (hexamine) are used by fire-protection laboratories as a clean and reproducible fire source to test the flammability of carpets and rugs.[9]

Food additive

Hexamethylene tetramine or hexamine is also used as a food additive as a preservative (INS number 239). It is approved for usage for this purpose in the EU,[10] where it is listed under E number E239, however it is not approved in the USA, Russia, Australia, or New Zealand.[11]

Reagent in organic chemistry

Hexamethylene tetramine is a versatile reagent in organic synthesis.[12] It is used in the Duff reaction (formylation of arenes),[13] the Sommelet reaction (converting benzyl halides to aldehydes),[14] and in the Delepine reaction (synthesis of amines from alkyl halides).[15]

Explosives of Hexamethylene tetramine

Hexamethylene tetramine is the base component to produce RDX and, consequently, C-4[4] as well as Octogen, hexamine dinitrate, hexamine diperchlorate and HMTD.

Historical uses of Hexamethylene tetramine

Hexamethylene tetramine was first introduced into the medical setting in 1899 as a urinary antiseptic.[16] However, it was only used in cases of acidic urine, whereas boric acid was used to treat urinary tract infections with alkaline urine.[17] Scientist De Eds found that there was a direct correlation between the acidity of Hexamethylene tetramine’s environment and the rate of its decomposition.[16] Therefore, its effectiveness as a drug depended greatly on the acidity of the urine rather than the amount of the drug administered.[17] In an alkaline environment, Hexamethylene tetramine was found to be almost completely inactive.[17]

Hexamethylene tetramine was also used as a method of treatment for soldiers exposed to phosgene in World War I. Subsequent studies have shown that large doses of Hexamethylene tetramine provide some protection if taken before phosgene exposure but none if taken afterwards.[18]

Producers

Since 1990 the number of European producers has been declining. The French SNPE factory closed in 1990; in 1993, the production of Hexamethylene tetramine in Leuna, Germany ceased; in 1996, the Italian facility of Agrolinz closed down; in 2001, the UK producer Borden closed; in 2006, production at Chemko, Slovak Republic, was closed. Remaining producers include INEOS in Germany, Caldic in the Netherlands, and Hexion in Italy. In the US, Eli Lilly and Company stopped producing Hexamethylene tetramine tablets in 2002.[9] In Australia, Hexamine Tablets for fuel are made by Thales Australia Ltd. In México, Hexamine is produced by Abiya.

Properties of Hexamethylene tetramine

Related Categoriesof Hexamethylene tetramine Building Blocks, Chemical Synthesis, Nitrogen Compounds – Organic Building Blocks, Organic Building Blocks, Polyamines Less…

Quality Levelof Hexamethylene tetramine 200

gradeof Hexamethylene tetramine ACS reagent

vapor pressure of Hexamethylene tetramine <0.01 mmHg ( 20 °C)

assayof Hexamethylene tetramine ≥99.0%

autoignition temp.of Hexamethylene tetramine 770 °F

ign. residueof Hexamethylene tetramine ≤0.1%

loss of Hexamethylene tetramine ≤2.0% loss on drying

Description of Hexamethylene tetramine

General description of Hexamethylene tetramine

Hexamethylene tetramine (HMTA) is a water soluble, heterocyclic organic compound with a cage-like structure resembling adamantane.[1] Hexamethylene tetramine is commonly used in treating urinary tract infection.[2]

Application of Hexamethylene tetramine

Hexamethylene tetramine (HMTA) may be used as:

• Raw material in the synthesis of blue emitting boron carbon oxynitride (BCNO) phosphors[3] and Zinc oxide (ZnO) nanorods.[6]

• Catalyst in the synthesis of 2-amino-4H-pyran derivatives.[1]

• Surfactant in the synthesis of HMTA capped transition metals doped ZnS nanoparticles.[4]

• Precipitant and template in the synthesis of Ni(OH)2.[5

Reactions of Hexamethylene tetramine

The chemistry of hexamethylene tetramine, or hexamine (70), has been reviewed thoroughly 〈B-61MI22000, p. 688, 59HC(13)1,p.545, 79S161〉. The discussion below summarizes these reviews. Hexamethylene tetramine has a symmetrical adamantane-like structure, and is quite stable. Hexamethylene tetramine is hydrolyzed by hot mineral acid to formaldehyde and the appropriate ammonium salt, but in cold dilute organic or mineral acid it forms salts. Hexamethylene tetramine is reduced to ammonia and formaldehyde in zinc and mineral acid. Quaternary salts (71) are formed by treatment of hexamine with alkyl halides. These salts are valuable synthetic reagents which may be used to prepare amines, imines and aldehydes (Scheme 48) and to effect ring closure.

Computed Properties HelpNew Window

Property Name Property Value Reference

Molecular Weight of Hexamethylene tetramine 140.19 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)

XLogP3-AA 0.3 Computed by XLogP3 3.0 (PubChem release 2019.06.18)

Hydrogen Bond Donor Count of Hexamethylene tetramine 0 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Hydrogen Bond Acceptor Count of Hexamethylene tetramine 4 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Rotatable Bond Count of Hexamethylene tetramine 0 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Exact Mass of Hexamethylene tetramine 140.106196 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)

Monoisotopic Mass of Hexamethylene tetramine 140.106196 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18)

Topological Polar Surface Area of Hexamethylene tetramine 13 Å² Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Heavy Atom Count of Hexamethylene tetramine 10 Computed by PubChem

Formal Charge of Hexamethylene tetramine 0 Computed by PubChem

Complexity of Hexamethylene tetramine 84.8 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Isotope Atom Count of Hexamethylene tetramine 0 Computed by PubChem

Defined Atom Stereocenter Count of Hexamethylene tetramine 0 Computed by PubChem

Undefined Atom Stereocenter Count of Hexamethylene tetramine 0 Computed by PubChem

Defined Bond Stereocenter Count of Hexamethylene tetramine 0 Computed by PubChem

Undefined Bond Stereocenter Count of Hexamethylene tetramine 0 Computed by PubChem

Covalently-Bonded Unit Count of Hexamethylene tetramine 1 Computed by PubChem

Compound of Hexamethylene tetramine Is Canonicalized Yes

Physical Description

Hexamethylene tetramine appears as odorless white crystalline powder or colorless lustrous crystals. Sublimes in a vacuum at about 505° F with some decomposition. Solutions are strong bases

Product Description

Hexamethylene tetramine

Application Notes of Hexamethylene tetramine

Hexamethylene tetramine is used for amino acid preparation. Hexamethylene tetramine is also used in synthesis as a formylation agent and is employed in preparing specialized materials. Hexamethylene tetramine is also used as a precipitating agent.Hexamethylenetetramine (HMTA) may be used as:

• Raw material in the synthesis of blue emitting boron carbon oxynitride (BCNO) phosphors and Zinc oxide (ZnO) nanorods.

• Catalyst in the synthesis of 2-amino-4H-pyran derivatives.

• Surfactant in the synthesis of HMTA capped transition metals doped ZnS nanoparticles.

• Precipitant and template in the synthesis of Ni(OH)2.

Usage Statement

Unless specified otherwise, MP Biomedical’s products are for research or further manufacturing use only, not for direct human use. For more information, please contact our customer service department.

Key Applications

Formylation agent | Amino acid preparation

Hexamethylenetetramine or methenamine is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like structure similar to adamantane. It is useful in the synthesis of other chemical compounds, e.g., plastics, pharmaceuticals, rubber additives. It sublimes in vacuum at 280 °C.

Applications

The dominant use of hexamethylenetetramine is in the production of powdery or liquid preparations of phenolic resins and phenolic resin moulding compounds, where it is added as a hardening component. These products are used as binders, e.g. in brake and clutch linings, abrasive products, non-woven textiles, formed parts produced by moulding processes, and fireproof materials.

It has been proposed that hexamethylenetetramine could work as a molecular building block for self-assembled molecular crystals.

Medical uses

As the mandelic acid salt (generic methenamine mandelate, USP) it is used for the treatment of urinary tract infection. It decomposes at an acidic pH to form formaldehyde and ammonia, and the formaldehyde is bactericidal; the mandelic acid adds to this effect. Urinary acidity is typically ensured by co-administering vitamin C (ascorbic acid) or ammonium chloride. Its use had temporarily been reduced in the late 1990s, due to adverse effects, particularly chemically-induced hemorrhagic cystitis in overdose, but its use has now been re-approved because of the prevalence of antibiotic resistance to more commonly used drugs. This drug is particularly suitable for long-term prophylactic treatment of urinary tract infection, because bacteria do not develop resistance to formaldehyde. It should not be used in the presence of renal insufficiency. Methenamine in the form of cream and spray is successfully used for treatment of excessive sweating and concomitant odour.

Histological stains

Methenamine silver stains are used for staining in histology, including the following types:

Grocott’s methenamine silver stain, used widely as a screen for fungal organisms.

Jones’ stain, a methenamine silver-Periodic acid-Schiff that stains for basement membrane, availing to view the “spiked” Glomerular basement membrane associated with membranous glomerulonephritis.

Solid fuel

Together with 1,3,5-trioxane, hexamethylenetetramine is a component of hexamine fuel tablets used by campers, hobbyists, the military and relief organizations for heating camping food or military rations. It burns smokelessly, has a high energy density of 30.0 megajoules per kilogram (MJ/kg), does not liquify while burning, and leaves no ashes.

Standardized 0.149 g tablets of methenamine (hexamine) are used by fire-protection laboratories as a clean and reproducible fire source to test the flammability of carpets and rugs.

Food additive

Hexamethylene tetramine or hexamine is also used as a food additive as a preservative (INS number 239). It is approved for usage for this purpose in the EU, where it is listed under E number E239, however it is not approved in the USA, Russia, Australia, or New Zealand.

Reagent in organic chemistry

Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction (formylation of arenes), the Sommelet reaction (converting benzyl halides to aldehydes), and in the Delepine reaction (synthesis of amines from alkyl halides).

Explosives

Hexamethylenetetramine is the base component to produce RDX and, consequently, C-4as well as Octogen, hexamine dinitrate and HMTD.

Application

Hexamethylenetetramine (HMTA) may be used as:

• Raw material in the synthesis of blue emitting boron carbon oxynitride (BCNO) phosphors and Zinc oxide (ZnO) nanorods.

• Catalyst in the synthesis of 2-amino-4H-pyran derivatives.

• Surfactant in the synthesis of HMTA capped transition metals doped ZnS nanoparticles.

• Precipitant and template in the synthesis of Ni(OH)2

It can be used as the curing agent for resins and plastics, the vulcanization accelerator of rubber (accelerator H) and textiles shrink-proof agent. It can also be used for making antibacterial drug, explosives and so on. As medicine, after oral administration, it can be decomposed when coming across acidic urine to generate formaldehyde and exerts its antibacterial effect used for treating mild urinary tract infection; it can be externally used for treating ringworm, antiperspirants, and treatment of underarm odor. Its being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks.

It can be used as a kind of anti-microbial agents.

It can be used as anti-shrinking textile finishing agent, bleaching agents of sodium chlorite and the buffer of waterproofing agents CR.

Hexamethylenetetramine is mainly used as the curing agent of plastic and resin, the catalyst and foaming agent of aminoplast, rubber vulcanization accelerator (accelerator H), and the shrink-proof agents of textiles. Hexamethylenetetramine is the raw material for organic synthesis and can be used for the production of chloramphenicol in the pharmaceutical industry. Hexamethylenetetramine can be used as the disinfectant of urinary system with itself having no antibacterial effect and being effective in treating gram-negative bacteria. Its 20% solution can be used for the treatment of underarm odor, sweaty feet, tinea and so on. Its being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks. It can also be used for the manufacture of pesticides. Hexamethylenetetramine can react with fuming nitric acid to obtain highly explosive cyclonite, briefly referred as RDX. Hexamethylenetetramine can be used as the reagent and chromatography reagents for determination of bismuth, indium, manganese, cobalt, thorium, platinum, producing magnesium, lithium, copper, uranium, beryllium, tellurium, bromide, and iodide.

In the liver function tests, it can be used for formulating thymol turbidity, test and measurement of object such as bismuth, iron, manganese, cobalt, thorium, platinum and magnesium as well as the determination and identification of lithium, iron cyanide, iron bromide and iodide. It can also be used for the determination of copper, uranium, beryllium, tellurium etc. Moreover, it can be used as gas chromatography fixed solution (maximum usage temperature of 180 ℃ with the solvent being chloroform).

HEXAMINE is also useful in adhesives, coatings, and sealing compounds. In medicine, it is an antibacterial agent. It is used as a dye fixative and in the preservation of hides. It is used in vulcanizing rubber and as an anti-corrosive agent in steel. It is used in the detection of metals and in the absorption of poisonous gases. It stabilizes lubricating and insulating oils. It is sometimes burned in camping stoves, because it burns without smoke.

HEKZAMETLEN TETRAMN

Hekzametilen Tetramin (E239)

Hekzametilen-tetramin.png

Hekzametilen Tetramin ya da Avrupa Birliinin verdii adyla E239 gda sanayinde koruyucu katk maddesi olarak kullanlan organik bir bileiktir. Metanamin olarak da bilinen hekzametilen tetramin ilk olarak Rus kimyager Aleksandr Butlerov tarafndan 1859’da kefedilmitir. Ticari olarak renksiz ya da beyaz kristaller halinde bulunan ve suda çok iyi çözünen hekzametilen tetramin formaldehitin amonyak ile reaksiyona sokulmas ile elde edilir. Antibakteriyel etkisi ile farkl sektörlerde kullanm alan bulan hekzametilen tetramin gda sanayinde özellikle peynir ve balk ürünlerinde küf mantarlarnn geliimini engellemek için kullanlr. Muhtemel salk etkileri nedeniyle hekzametilen tetraminin gdalara katk maddesi olarak ilave edilmesi baz ülkelerde yasaklanmtr. Türk Gda Kodeksi hekzametilen tetraminin sadece baz peynir çeitlerinde ve snrlandrlan miktarlarda kullanmna izin vermektedir.

çindekiler

1 Hekzametilen Tetramin Hakknda Bilgiler

2 Canllarda Hekzametilen Tetramin

3 Hekzametilen Tetraminin Kullanm Amac

4 Hekzametilen Tetramin Helal midir

5 Hekzametilen Tetraminin Sala Etkileri

6 Hekzametilen Tetramin Nasl Üretilir

7 lgili Maddeler

8 Kaynakça

Hekzametilen Tetramin Hakknda Bilgiler

Hekzametilen Tetraminin Dier simleri: Metanamin, hekzamin

Hekzametilen Tetraminin Avrupa Birlii Kodu: E239

Hekzametilen Tetraminin Kimyasal Formülü: C6H12N4

Hekzametilen Tetraminin ngilizcesi: Hexamethylenetetramine, methenamine, hexamine

Canllarda Hekzametilen Tetramin

Hekzametilen tetramin canllarda doal olarak bulunmayan ve kimyasal reaksiyon ile elde edilen organik bir bileiktir. nsan vücuduna alndnda hekzametilen tetramin %10-20’si hidrolize urayarak formaldehit ve amonyak meydana gelir; geri kalan ksm deiime uramadan idrarla atlr.[1]

Hekzametilen Tetraminin Kullanm Amac

Hekzametilen tetramin peynirlerde ve balk ürünlerinde küf mantarlarnn geliiminin engellenmesi için koruyucu katk maddesi olarak kullanlr. Ülkemizde sadece provolone peynir çeidinde kullanlabilmektedir.

Koruyucu etkisi ile hekzametilen tetramin ampuan ve saç kremi gibi kiisel bakm ürünlerinde ve veteriner ilaçlarnda kullanlr. Ayrca hayvan beslemede kullanlan silajlara katk maddesi olarak ilave edilir.

Hekzametilen tetramin idrar yolu enfeksiyonlarnn tedavisinde kullanlan baz ilaçlarn etken maddesidir. lave olarak ar terleme rahatszlnda hekzametilen tetramin içeren krem ya da spreyler kullanlr.

Farkl sektörlerde kullanlan fenolik resinlerin üretiminde hekzametilen tetraminden faydalanlr. Fenolik resinler otomotiv sanayinde fren ve debriyaj balatalarnda, dokuma olmayan tekstil ürünlerinde ve andrc ürünlerde kullanlmaktadr.

Hekzametilen Tetramin Helal midir

Hekzametilen tetraminin kullanlmasnda dini açdan bir saknca yoktur.

Hekzametilen Tetraminin Sala Etkileri

FAO/WHO (Birlemi Milletler Gda ve Tarm Örgütü/Dünya Salk Örgütü) tarafndan oluturulmu Gda Katk Maddeleri Ortak Uzman Komitesi hekzametilen tetramin insan salna olumsuz etki yapmadan günlük alnabilecek miktarn 0,15 mg/kg vücut arl olarak belirlemitir.[2] Hekzametilen tetramin ürtiker, solunum zorluu, yüz ve dudaklarda ime gibi alerjik reaksiyonlara ya da iç bulants ve mide bozukluu gibi yan tesirlere yol açabilir. Ancak bu olumsuz salk etkilerin hekzametilen tetraminin içeren gdalarn tüketilmesi sonucu görülmesi ihtimali düüktür. Yan tesirler genellikle hekzametilen tetraminin idrar yolu enfeksiyonlarna kar ilaç olarak kullanldna ortaya çkar. Hekzametilen tetramin nitrit ile tepkimeye girdiinde sala zararl nitrozamin bileikleri oluur. Bu nedenle bu katk maddesinin kullanld gdalarn nitrit içeren ürünlerle beraber tüketilmemesi tavsiye edilir.

Hekzametilen Tetramin Nasl Üretilir

Hekzametilen Tetraminin üretimi: Düük basnç altnda formaldehitin amonyak ile sv fazda tepkimeye girmesi ile kat halde hekzametilen tetramin oluur. Elde edilen saf haldeki hekzametilen tetramin daha sonra boyut küçültme ilemine tabi tutulup ambalajlanr.

Hekzametilen Tetramin Formül: C6H12N4

Hekzametilen Tetramin Molar kütle: 140,186 g/mol

Hekzametilen Tetramin IUPAC numaras: 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane

Hekzametilen Tetramin Kaynama noktas: 280 °C

Hekzametilen Tetramin Younluk: 1,33 g/cm³

Hekzametilen Tetramin çinde çözündüü madde: Su

Hexamethylen etetramine ya da methenamine, amonyan formola etkimesiyle elde edilen kimyasal ilaç. Genellikle idrar yollar antiseptii olarak kullanlr.

Hekzametilen Tetramin

Hekzametilen Tetramin ya da methenamine, (fr. méthénamine) amonyan formola etkimesiyle elde edilen kimyasal ilaç. Genellikle idrar yollar antiseptii olarak kullanlr. Hekzametilen Tetramin Formülü (CH2)6N4 ‘dr. 1860 ylnda Rus kimyager Butlerov tarafndan bulunmutur. 1972 ylna kadar formin, hekzametilen tetramin , hekzamin, ürotropin gibi adlar metanamin kimyasal için kullanlmtr. Metanamin kimyasal azdan alnr. Hekzametilen Tetramin baz romatizma hastalar içinde kullanlmtr.[1]

Heksametilen tetraminin özellikleri

lgili Kategorilerheksametilen tetramin Yap Talar, Kimyasal Sentez, Azot Bileikleri – Organik Yap Talar, Organik Yap Talar, Poliaminler Daha Az …

Heksametilen tetramin 200 Kalite Düzeyi

gradeof Heksametilen tetramin ACS reaktifi

Heksametilen tetraminin buhar basnc <0.01 mmHg (20 ° C)

heksametilen tetramin tayini ≥% 99.0

Kendiliinden tutuma scakl Heksametilen tetramin 770 ° F

ign. Heksametilen tetramin kalnts ≤% 0,1

Heksametilen tetramin kayb ≤% 2,0 kuruma kayb

Heksametilen tetraminin tanm

Heksametilen tetraminin genel tanm

Heksametilen tetramin (HMTA), adamantana benzeyen kafes benzeri bir yapya sahip, suda çözünür, heterosiklik bir organik bileiktir. [1] Hekzametilen tetramin, idrar yolu enfeksiyonunun tedavisinde yaygn olarak kullanlmaktadr. [2]

Heksametilen tetramin uygulamas

Hekzametilen tetramin (HMTA) u ekilde kullanlabilir:

• Mavi yayan bor karbon oksinitrür (BCNO) fosforlar [3] ve Çinko oksit (ZnO) nanorodlarnn sentezinde hammadde. [6]

• 2-amino-4H-piran türevlerinin sentezinde katalizör. [1]

• HMTA balkl geçi metalleri katkl ZnS nanopartiküllerinin sentezinde yüzey aktif madde. [4]

• Ni (OH) 2’nin sentezinde çökeltici ve ablon. [5

Heksametilen tetramin reaksiyonlar

Hekzametilen tetramin veya heksaminin (70) kimyas iyice gözden geçirilmitir 〈B-61MI22000, s. 688, 59HC (13) 1, s. 545, 79S161〉. Aadaki tartma bu incelemeleri özetlemektedir. Hekzametilen tetramin simetrik adamantana benzer bir yapya sahiptir ve oldukça stabildir. Heksametilen tetramin, scak mineral asit ile formaldehite ve uygun amonyum tuzuna hidrolize edilir, ancak souk seyreltik organik veya mineral asitte tuzlar oluturur. Hekzametilen tetramin, çinko ve mineral asitte amonyak ve formaldehite indirgenir. Kuaterner tuzlar (71), heksaminin alkil halojenürlerle ilenmesiyle oluturulur. Bu tuzlar, aminleri, iminleri ve aldehitleri (ema 48) hazrlamak ve halka kapanmasn gerçekletirmek için kullanlabilen deerli sentetik reaktiflerdir.

Hekzametilen Tetramin Hesaplanan Özellikler Yardm

Heksametilen tetraminin Moleküler Arl 140,19 g / mol PubChem 2.1 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

XLogP3-AA 0.3, XLogP3 3.0 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

Heksametilen tetraminin Hidrojen Ba Donör Says 0 Cactvs 3.4.6.11 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

Heksametilen tetramin 4 Hidrojen Ba Kabul Eden Says Cactvs 3.4.6.11 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

Heksametilen tetraminin Döndürülebilir Ba Says 0 Cactvs 3.4.6.11 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

Heksametilen tetraminin Tam Kütlesi 140.106196 g / mol PubChem 2.1 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

Heksametilen tetraminin Monoizotopik Kütlesi 140.106196 g / mol PubChem 2.1 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

Heksametilen tetramin 13 Å²’nin Topolojik Polar Yüzey Alan Cactvs 3.4.6.11 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

PubChem Tarafndan Hesaplanan Heksametilen tetramin 10 Ar Atom Says

Heksametilen tetraminin Resmi Yükü 0 PubChem tarafndan hesaplanmtr

Heksametilen tetramin 84.8’in karmakl Cactvs 3.4.6.11 tarafndan hesaplanmtr (PubChem sürümü 2019.06.18)

Heksametilen tetraminin zotop Atom Says 0 PubChem tarafndan hesaplanmtr

Tanmlanm Atom Stereocenter Says Heksametilen tetramin 0 PubChem tarafndan hesaplanmtr

Tanmlanmam Atom Stereocenter Heksametilen tetramin Says 0 PubChem tarafndan hesaplanmtr

Tanmlanm Ba Stereocenter Says Heksametilen tetramin 0 PubChem tarafndan hesaplanmtr

Tanmlanmam Ba Stereocenter Says Heksametilen tetramin 0 PubChem tarafndan hesaplanmtr

PubChem Tarafndan Hesaplanan Kovalent Bal Heksametilen tetramin 1 Birim Says

Heksametilen tetramin Bileii Kanonikalletirilmitir Evet

Hekzametilen Tetramin Fiziksel tanm

Hekzametilen tetramin, kokusuz beyaz kristal toz veya renksiz parlak kristaller olarak görünür. Bir miktar ayrmayla yaklak 505 ° F’de vakumda süblimleir. Çözümler güçlü temellerdir

Ürün Açklamas

Hekzametilen tetramin

Hekzametilen tetramin Uygulama Notlar

Amino asit hazrlanmasnda heksametilen tetramin kullanlr. Heksametilen tetramin ayrca bir formilasyon ajan olarak sentezde kullanlr ve özel materyallerin hazrlanmasnda kullanlr. Heksametilen tetramin ayrca çökeltme ajan olarak kullanlr. Heksametilentetramin (HMTA) u ekilde kullanlabilir:

• Mavi yayan bor karbon oksinitrür (BCNO) fosforlar ve Çinko oksit (ZnO) nanorodlarnn sentezinde hammadde.

• 2-amino-4H-piran türevlerinin sentezinde katalizör.

• HMTA balkl geçi metalleri katkl ZnS nanopartiküllerinin sentezinde yüzey aktif madde.

• Ni (OH) 2 sentezinde çökeltici ve ablon.

Heksametilentetramin veya metenamin, (CH2) 6N4 formülüne sahip bir heterosiklik organik bileiktir. Bu beyaz kristalin bileik, su ve polar organik çözücüler içinde oldukça çözünürdür. Adamantana benzer kafes benzeri bir yapya sahiptir. Dier kimyasal bileiklerin, örnein plastik, farmasötik maddeler, kauçuk katk maddeleri sentezinde yararldr. 280 ° C’de vakum altnda yükselir.

Hekzametilen Tetramin Uygulamalar

Heksametilen tetramin baskn kullanm, bir sertletirme bileeni olarak ilave edildiinde, fenolik reçinelerin ve fenolik reçine kalplama bileiklerinin toz veya sv müstahzarlarnn üretiminde bulunur. Bu ürünler balayc olarak kullanlr, örn. Fren ve debriyaj astarlar, andrc ürünler, dokumasz tekstil, kalplama yöntemiyle üretilen parçalar ve yanmaz malzemeler.

Heksametilen tetramin’in kendi kendine monte edilmi moleküler kristaller için bir moleküler yap ta olarak çalabilecei önerilmitir.

Hekzametilen Tetramin Tbbi kullanmlar

Mandelik asit tuzu (jenerik metenamin mandelat, USP) idrar yolu enfeksiyonunun tedavisinde kullanlr. Formaldehit ve amonyak oluturmak için asidik bir pH’da ayrr ve formaldehit bakterisidaldr; Mandelik asit bu etkiyi arttrr. drar asiditesi, tipik olarak, C vitamini (askorbik asit) veya amonyum klorürün birlikte uygulanmasyla salanmaktadr. Ar dozlarda kimyasal kaynakl hemorajik sistit gibi yan etkiler nedeniyle kullanm 1990’l yllarn sonunda geçici olarak azalmt, ancak artk yaygn kullanlan ilaçlara kar antibiyotik direnci yaygnl nedeniyle kullanm tekrar onayland. Bu ilaç, idrar yolu enfeksiyonunun uzun vadeli profilaktik tedavisi için özellikle uygundur, çünkü bakteriler formaldehite direnç göstermezler. Böbrek yetmezliinde kullanlmamaldr. Krem ve sprey eklindeki metenamin, ar terleme ve beraberinde gelen kokunun tedavisinde baarl bir ekilde kullanlr.

Histolojik boyalar

Methenamin gümü lekeleri, histoloji boyama için kullanlr, bunlar arasnda aadakiler bulunur:

Grocott’un metanamin gümü lekesi, fungal organizmalar için bir ekran olarak yaygn olarak kullanlr.

Jones’un lekesi, metanamin gümüü-Periyodik asit-Schiff, membranöz glomerülonefrit ile ilikili “çivili” Glomerüler bazal membrann görüntüsünü elde etmek için avare eden bazal membran için lekeler.

Kat yakt

1,3,5-trioksan ile birlikte, hekzametilenetetamin, kampçlara, hobi üyelerine, ordu ve yardm organizasyonlarnn kamp yemekleri veya askeri rasyonalrn stlmas için kullanlan heksamin yakt tabletlerinin bir bileenidir. Dumanszca yakar, kilogram bana 30.0 megazul (MJ / kg) kadar yüksek bir enerji younluuna sahiptir, yanarken svlamaz ve kül brakmaz.

Standartlatrlm 0.149 g metenamin tabletleri (heksamin), hal ve kilimlerin yancln test etmek için yangn koruma laboratuvarlar tarafndan temiz ve tekrarlanabilir bir yangn kayna olarak kullanlr.

Gda katk maddesi

Heksametilen tetramin veya heksamin ayrca bir koruyucu olarak gda katk maddesi olarak kullanlr (INS numaras 239). Bu amaçla, E numaras E239 altnda listelenen AB’de kullanm için onaylanmtr, ancak ABD, Rusya, Avustralya veya Yeni Zelanda’da onaylanmamtr.

Organik kimyada reaktif

Heksametilentetramin, organik sentezde çok yönlü bir reaktiftir. Duff reaksiyonunda (arilenlerin formilasyonu), Sommelet reaksiyonu (benzil halidlerin aldehitlere dönütürülmesi) ve Delepin reaksiyonunda (alkil halojenürlerden amin sentezi) kullanlr.

Patlayclar

Heksametilentetramin, RDX üretmek için temel bileenidir ve dolaysyla Octogen, hexamine dinitrate ve HMTD gibi C-4as’tr.

Uygulama

Heksametilentetramin (HMTA) u ekilde kullanlabilir:

• Mavi yayc bor karbon oksinitrid (BCNO) fosfor ve Çinko oksit (ZnO) nanorodlarnn sentezinde hammadde.

• 2-amino-4H-piran türevlerinin sentezinde katalizör.

• HMTA kapl geçi metallerinin sentezindeki yüzey aktif madde, ZnS nanopartiküllerine katkl.

• Ni (OH) 2 sentezinde çökelti ve ablon

Reçineler ve plastikler için kürleme ajan, kauçuun vulkanizasyon hzlandrcs (hzlandrc H) ve tekstil küçülmez ajan olarak kullanlabilir. Ayn zamanda antibakteriyel ilaç, patlayc vb. Üretmek için de kullanlabilir. laç olarak oral yoldan verildikten sonra, formaldehit üretmek için asidik idrar ile karlatnda ayrabilir ve hafif üriner sistem enfeksiyonunun tedavisinde kullanlan antibakteriyel etkisini uygular; Kirpiklerin, terleyicilerin ve koltukalt kokusunun tedavisinde dardan kullanlabilir. Kostik soda ve sodyum fenol ile kartrlmas, gaz maskelerinin fosgen emici olarak kullanlabilir.

Bir çeit anti-mikrobiyal ajan olarak kullanlabilir.

Darbelere kar dayankl tekstil apre maddesi, sodyum klorit aartma maddeleri ve su yaltm malzemeleri CR tamponu olarak kullanlabilir.

Heksametilentetramin çounlukla plastik ve reçinenin sertletirici ajan, aminoplastn katalizör ve köpükletirici ajan, kauçuk vulkanizasyon hzlandrcs (hzlandrc H) ve tekstillerin büzüme önleyici ajanlar olarak kullanlr. Heksametilentetramin organik sentez için hammaddedir ve farmasötik endüstrisinde kloramfenikol üretimi için kullanlabilir. Heksametilentetramin, kendisinin antibakteriyel etkisi olmayan ve gram negatif bakterilerin tedavisinde etkilidir idrar sisteminin dezenfektan olarak kullanlabilir. % 20 solüsyonu, koltuk alt kokusunun, terli ayaklarn, tinea’nn vb. Tedavisinde kullanlabilir. Kostik soda ve sodyum fenol ile kartrlmas, gaz maskelerinin fosgen emici olarak kullanlabilir. Pestisit imalatnda da kullanlabilir. Heksametilenetetamin, ksaca RDX olarak anlacak patlayc sikloniti elde etmek için dumanl nitrik asit ile reaksiyona girebilir. Heksametilenetetamin, bizmut, indiyum, manganez, kobalt, toryum, platin, magnezyum, lityum, bakr, uranyum, berilyum, tellür, bromür ve iyodür üretmek için reaktif ve kromatografi reaktifleri olarak kullanlabilir.

Karacier fonksiyon testlerinde, bizmut, demir, manganez, kobalt, toryum, platin ve magnezyum gibi timol bulankln, deneyi ve ölçümü ile lityum, demir siyanür, demir bromürün belirlenmesi ve tanmlanmas için kullanlabilir Ve iyodür. Ayrca bakr, uranyum, berilyum, tellürum vb. Tayini için kullanlabilir. Ayrca, gaz kromatografi sabit çözeltisi (solventin kloroform olmas ile maksimum kullanm scakl 180 ° C) olarak kullanlabilir.

Hekzametilen Tetramin yapkanlarda, kaplamalarda ve szdrmazlk bileiklerinde de yararldr. Tpta antibakteriyel bir ajandr.Hekzametilen Tetramin Boya fiksatifi olarak ve derilerin korunmasnda kullanlr. Kauçuk vulkanizasyonunda ve paslanmaya kar koruyucu bir ajan olarak kullanlr.Hekzametilen Tetramin Metallerin tespitinde ve zehirli gazlarn emilmesinde kullanlr. Hekzametilen Tetramin Yalama ve izolasyon yalarn dengeler.Hekzametilen Tetramin Kamp ocaklarnda bazen yanar, çünkü dumansz yanar.

Hexaméthylène Tétramine

Propriétés de l’hexaméthylène tétramine

Catégories associéesde Blocs de construction hexaméthylène tétramine, Synthèse chimique, Composés azotés – Blocs de construction organiques, Blocs de construction organiques, Polyamines Moins …

Niveau de qualité de l’hexaméthylène tétramine 200

grade de réactif ACS hexaméthylène tétramine

pression de vapeur de l’hexaméthylène tétramine <0,01 mmHg (20 ° C)

dosage de l’hexaméthylène tétramine ≥99,0%

température d’auto-inflammation de l’hexaméthylène tétramine 770 ° F

ign. résidu d’hexaméthylène tétramine ≤0,1%

perte d’hexaméthylène tétramine ≤ 2,0% perte au séchage

Description de l’hexaméthylène tétramine

Description générale de l’hexaméthylène tétramine

L’hexaméthylène tétramine (HMTA) est un composé organique hétérocyclique soluble dans l’eau avec une structure en forme de cage ressemblant à l’adamantane. [1] L’hexaméthylène tétramine est couramment utilisée dans le traitement des infections des voies urinaires. [2]

Application de l’hexaméthylène tétramine

L’hexaméthylène tétramine (HMTA) peut être utilisé comme:

• Matière première dans la synthèse de phosphores d’oxynitrure de carbone (BCNO) émettant dans le bleu [3] et de nanorods d’oxyde de zinc (ZnO). [6]

• Catalyseur dans la synthèse de dérivés de 2-amino-4H-pyrane. [1]

• Tensioactif dans la synthèse de nanoparticules de ZnS dopées par des métaux de transition coiffés de HMTA. [4]

• Précipitant et matrice dans la synthèse de Ni (OH) 2. [5

Réactions de l’hexaméthylène tétramine

La chimie de l’hexaméthylène tétramine, ou hexamine (70), a été revue de manière approfondie 〈B-61MI22000, p. 688, 59HC (13) 1, p. 545, 79S161〉. La discussion ci-dessous résume ces examens. L’hexaméthylène tétramine a une structure symétrique de type adamantane et est assez stable. L’hexaméthylène tétramine est hydrolysée par l’acide minéral chaud en formaldéhyde et le sel d’ammonium approprié, mais dans l’acide organique ou minéral dilué à froid, elle forme des sels. L’hexaméthylène tétramine est réduite en ammoniac et en formaldéhyde en zinc et en acide minéral. Les sels quaternaires (71) sont formés par traitement de l’hexamine avec des halogénures d’alkyle. Ces sels sont des réactifs synthétiques intéressants qui peuvent être utilisés pour préparer des amines, des imines et des aldéhydes (schéma 48) et pour effectuer la cyclisation.

Aide sur les propriétés calculées Nouvelle fenêtre

Nom de la propriété Valeur de la propriété Référence

Poids moléculaire de l’hexaméthylène tétramine 140,19 g / mol calculé par PubChem 2.1 (PubChem release 2019.06.18)

XLogP3-AA 0.3 calculé par XLogP3 3.0 (PubChem release 2019.06.18)

Nombre de donneurs de liaison hydrogène d’hexaméthylène tétramine 0 calculé par Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Nombre d’accepteurs de liaison hydrogène de l’hexaméthylène tétramine 4 calculé par Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Nombre de liaisons rotatives de l’hexaméthylène tétramine 0 calculé par Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Masse exacte d’hexaméthylène tétramine 140,106196 g / mol calculée par PubChem 2.1 (PubChem release 2019.06.18)

Masse monoisotopique de l’hexaméthylène tétramine 140,106196 g / mol calculée par PubChem 2.1 (PubChem release 2019.06.18)

Surface polaire topologique de l’hexaméthylène tétramine 13 Å² calculée par Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Nombre d’atomes lourds d’hexaméthylène tétramine 10 calculé par PubChem

Charge formelle d’hexaméthylène tétramine 0 calculée par PubChem

Complexité de l’hexaméthylène tétramine 84,8 calculée par Cactvs 3.4.6.11 (PubChem release 2019.06.18)

Nombre d’atomes isotopiques de l’hexaméthylène tétramine 0 calculé par PubChem

Nombre défini de stéréocentres atomiques d’hexaméthylène tétramine 0 calculé par PubChem

Nombre de stéréocentre atomique indéfini d’hexaméthylène tétramine 0 calculé par PubChem

Nombre défini de stéréocentre de liaison d’hexaméthylène tétramine 0 calculé par PubChem

Nombre de stéréocentres de liaison indéfini d’hexaméthylène tétramine 0 calculé par PubChem

Nombre d’unités liées par covalence d’hexaméthylène tétramine 1 calculé par PubChem

Le composé d’hexaméthylène tétramine est canonisé Oui

Description physique

L’hexaméthylène tétramine se présente sous forme de poudre cristalline blanche inodore ou de cristaux brillants incolores. Sublime sous vide à environ 505 ° F avec une certaine décomposition. Les solutions sont des bases solides

Description du produit

Hexaméthylène tétramine

Notes d’application de l’hexaméthylène tétramine

L’hexaméthylène tétramine est utilisée pour la préparation des acides aminés. L’hexaméthylène tétramine est également utilisée en synthèse comme agent de formylation et est utilisée dans la préparation de matériaux spécialisés. L’hexaméthylène tétramine est également utilisée comme agent de précipitation.L’hexaméthylènetétramine (HMTA) peut être utilisée comme:

• Matière première dans la synthèse de phosphores d’oxynitrure de carbone et de bore émettant dans le bleu (BCNO) et de nanorods d’oxyde de zinc (ZnO).

• Catalyseur dans la synthèse de dérivés 2-amino-4H-pyrane.

• Tensioactif dans la synthèse de nanoparticules de ZnS dopées aux métaux de transition coiffés de HMTA.

• Précipitant et matrice dans la synthèse de Ni (OH) 2.

Hexaméthylène Tétramine

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Méthénamine

Image illustrative de l’article Méthénamine

Identification

Nom UICPA 1,3,5,7-tétraazatricyclo[3.3.1.13,7]décane

Synonymes

hexamine, urotropine, hexaméthylènetétramine

No CAS du Hexaméthylène Tétramine 100-97-0

No ECHA du Hexaméthylène Tétramine 100.002.642

No CE du Hexaméthylène Tétramine 202-905-8

Code ATC J01XX05

PubChem du Hexaméthylène Tétramine 4101

No E du Hexaméthylène Tétramine E239

SMILES

[Afficher]

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Apparence du Hexaméthylène Tétramine cristaux hygroscopiques et incolores ou poudre cristalline blanche1

Propriétés chimiques du Hexaméthylène Tétramine

Formule brute du Hexaméthylène Tétramine C6H12N4 [Isomères]

Masse molaire du Hexaméthylène Tétramine2 140,1863 ± 0,0064 g/mol

C 51,41 %, H 8,63 %, N 39,97 %,

Propriétés physiques du Hexaméthylène Tétramine

T° fusion du Hexaméthylène Tétramine >263 °C décomposition en formaldéhyde, NOx, ammoniac

T° ébullition du Hexaméthylène Tétramine Point de sublimation : environ 260 °C1

Solubilité du Hexaméthylène Tétramine Eau : 853 g·l-1 à 25 °C

Chloroforme du Hexaméthylène Tétramine : 13,4 % à 20 °C

Éthanol du Hexaméthylène Tétramine : 2,89 % à 20 °C

Acétone du Hexaméthylène Tétramine : 0,65 % à 20 °C

Éther du Hexaméthylène Tétramine: 0,06 % à 20 °C

Méthanol du Hexaméthylène Tétramine : 7,25 % à 20 °C

Masse volumique du Hexaméthylène Tétramine 1,33 g·cm-31

T° d’auto-inflammation 390 °C1

Point d’éclair 250 °C (coupelle fermée)1

Pression de vapeur saturante ≈0,0005 mbar à 20 °C

≈0,0015 mbar à 30 °C

≈0,009 mbar à 50 °C

Précautions

SGH3

SGH02 : InflammableSGH08 : Sensibilisant, mutagène, cancérogène, reprotoxique

Danger

H228, H317, H334,

[+]

SIMDUT4

B4 : Solide inflammable

B4,

[+]

Transport

–

1328

[+]

Écotoxicologie

DL50 569 mg·kg-1 (souris, oral)

17,7 ml·kg-1 (souris, i.v.)

215 mg·kg-1 (souris, s.c.)

LogP -2,841

Unités du SI et CNTP, sauf indication contraire.

modifier Consultez la documentation du modèle

La méthénamine, hexamine, urotropine, ou hexaméthylènetétramine, est un composé organique hétérocyclique possédant une structure cage de type adamantane. Il fut découvert en 1859 par le chimiste russe Alexandre Boutlerov.

Ce composé est utilisé dans des applications diverses et variées, par exemple comme antibiotique pour le traitement des infections urinaires, dans la fabrication de résines, ou comme réactif organique.

Généralités

Structure

La hexaméthylène tétramine(CH2)6N4 possède quatre atomes d’azote reliés entre eux par des groupements méthylène. Cette molécule présente donc une structure cage, symétrique, similaire à celle de l’adamantane. Malgré sa forme moléculaire, la hexaméthylène tétraminen’est pas capable d’encapsuler d’autres atomes ou molécules car l’espace vide à l’intérieur de celle-ci n’est pas suffisant à la création de liaisons.

Synthèse

La hexaméthylène tétramineest obtenue par une réaction de condensation entre le formaldéhyde et l’ammoniac. Cette réaction peut être réalisée en phase gaz ou en solution.

Schéma de la réaction de synthèse de l’HMTA

Propriétés

La hexaméthylène tétraminese présente sous la forme d’une poudre blanche ou de cristaux incolores hygroscopiques.

Elle est très soluble dans l’eau, soluble dans les solvants organiques polaires tels que le méthanol et l’éthanol, peu soluble dans l’éther éthylique et insoluble dans l’éther de pétrole.

À température élevée (200 à 300 °C), la hexaméthylène tétraminese décompose principalement en ammoniac et en formaldéhyde.

Les solutions aqueuses de hexaméthylène tétramine sont faiblement basiques (une solution à 0,2 M en HMTA a un pH de 8,4). En milieu acide, elle s’hydrolyse en libérant ammoniac et formaldéhyde5.

Applications du hexaméthylène tétramine

méthénamine

Noms commerciaux

Antihydral (pommade, en association) (Suisse)

Carbobel (en association) (Belgique)

Hip Rex Tab 1 GM (Canada)

Mandelamine (Canada)

Mictasol (Belgique)

Urotropine (France : retiré du marché en mai 2011)

Laboratoire Erfa Canada 2012 Inc, Graceway, Iromedica, Lafran, Medgenix

Forme comprimés dosés à 50 mg, à 100 mg pour 5 g, à 1 g

Administration per os ; pommade pour applications cutanées

Classe

autres préparations dermatologiques, antisudoraux, ATC code D11AA

antibactériens à usage systémique, autres antibactériens, ATC code J01XX05

Identification

No CAS 100-97-0Voir et modifier les données sur Wikidata

No ECHA 100.002.642

Code ATC J01XX05

DrugBank 06799Voir et modifier les données sur Wikidata

modifier Consultez la documentation du modèle

Domaine médical

De par certaines de ses caractéristiques, la hexaméthylène tétramine est utilisée comme antibiotique dans le traitement des infections des voies urinaires basses. L’urine étant acide, la molécule, relativement peu toxique, se décompose en formaldéhyde et ammoniac. Le formaldéhyde possède des propriétés bactéricides et va donc combattre l’infection.

La hexaméthylène tétramine se présente sous la forme d’un comprimé gastro-résistant nécessaire pour contourner l’acidité gastrique et n’agir que dans les voies urinaires. Malgré cette forme d’administration, ce médicament reste relativement peu coûteux.

De plus, il est particulièrement adapté à long terme car les bactéries ne développent pas de résistance au formaldéhyde.

Colorant histologique

Les colorants argentiques de la hexaméthylène tétraminesont employés pour la coloration en histologie, incluant les méthodes suivantes :

la coloration argentique de Grocott, largement employée pour la visualisation des organismes fongiques ;

la coloration argentique de Jones, un acide periodique de Schiff, combiné à de l’argent et à de la méthénamine, permettant de voir l’aspect « piqueté » des membranes basales glomérulaires des glomérulonéphrites extramembraneuses, pour le diagnostic de cette maladie auto-immune.

Résine

La hexaméthylène tétramine sert également dans la préparation des résines phénoliques. Elle peut être utilisée comme agent réticulant de par la formation de formaldéhyde qui va permettre d’assembler les phénols entre eux.

La hexaméthylène tétramineest aussi utilisée comme catalyseur et permet le contrôle de la porosité au sein de la résine.

Combustible solide

L’hexaméthylène tétramine est aussi le principal composé de certaines pastilles de combustible. Ces pastilles sont utilisées par les campeurs, des laboratoires de recherches pour standardiser les sources de feu (essais d’inflammabilité) ou les militaires pour le réchauffage des aliments dans certaines rations alimentaires de l’armée française.

Elles brûlent sans dégagement de fumée, ne se liquéfient pas en brûlant et ne produisent pas de cendres. La densité énergétique est importante (30,0 MJ/kg). Cependant, la chaleur produite par ces pastilles est difficile à contrôler et les vapeurs qui s’en échappent sont nocives.

Additif alimentaire

L’hexaméthylène tétramine est aussi employée comme additif alimentaire en tant que conservateur, sous le code E239. Autorisée à l’usage dans ce but dans l’Union européenne, elle n’est cependant pas approuvée aux États-Unis, ainsi qu’en Russie, l’Australie ou la Nouvelle-Zélande.

Chimie organique

L’hexaméthylène tétramine est un réactif en synthèse organique utilisé dans plusieurs réactions chimiques notamment la réaction de Duff (formylation aromatique), la réaction de Sommelet (transformation des halogénures benzyliques en aldéhydes) ou dans la réaction de Delépine (en) (synthèse d’amines à partir d’halogénures d’alkyles).

Explosifs

L’hexaméthylène tétramine est le composant de base dans la production du RDX (hexogène) et en conséquence du C-4, ainsi que de l’octogène, le dinitrate d’hexamine (HDN), le triperoxyde d’hexaméthylène diamine (HMTD), etc.

Autres applications

L’hexaméthylènetétramine est également utilisée comme inhibiteur de corrosion dans l’industrie des métaux, conservateur dans l’industrie des peintures, comme fongicide et a une utilité dans le domaine des cosmétiques, de l’industrie alimentaire, etc.

Notes et références

HEXAMETHYLENE TETRAMINE [archive], fiche(s) de sécurité du Programme International sur la Sécurité des Substances Chimiques [archive], consultée(s) le 9 mai 2009

Masse molaire calculée d’après « Atomic weights of the elements 2007 » [archive], sur www.chem.qmul.ac.uk.

Numéro index 612-101-00-2 dans le tableau 3.1 de l’annexe VI du règlement CE N° 1272/2008 [archive] (16 décembre 2008)

« Hexaméthylènetétramine [archive] » dans la base de données de produits chimiques Reptox de la CSST (organisme québécois responsable de la sécurité et de la santé au travail), consulté le 25 avril 2009

(en) Substance Display 7847459 [archive], NCBI database

Voir aussi

HEXAMETHYLENE TETRAMINE (HEKZAMETLEN TETRAMN)

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HEXAMETHYLENE TETRAMINE (HEKZAMETLEN TETRAMN)

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