HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hexamethylenetetramine
HMTA · HEXAMINE · METHENAMINE · UROTROPINE · 1,3,5,7-TETRAAZAADAMANTANE · UROTROPIN · hexamethylentetramine · WLTP
Identifiers & Physical Properties
| CAS No. | 100-97-0 |
|---|---|
| Molecular formula | C6H12N4 |
| Average molar mass | 140.19 g/mol |
| Monoisotopic mass | 140.10619638 g/mol |
| SMILES | C1N2CN3CN1CN(C2)C3 |
| InChIKey | VKYKSIONXSXAKP-UHFFFAOYSA-N |
| PubChem CID | 4101 |
| ChEMBL | CHEMBL1201270 |
| ChEBI | CHEBI:6824 |
| EC No. | 202-905-8 |
| DTXSID | DTXSID6020692 |
Chemical & Physical Properties
| XLogP | 0.3 |
|---|---|
| Topological polar surface area | 13 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 0 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 84.8 |
| Chemical classes | Nitrogen Compounds -> Amines, AliphaticPharmaceutical |
| Drugs | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics |
| Cosmetics | Cosmetic ingredients (Methenamine) -> CIR (Cosmetic Ingredient Review)Preservative |
| pH | pH of 0.2 molar aqueous solution: 8.47-10 (100g/l, H2O, 20℃) |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| Pesticides | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approvedBactericides |
| LogP (partition coefficient) | log Kow = -2.18 at pH 7-9, 20 °C-2.84 |
| Odor | OdorlessPractically odorless |
| Density | 1.35 at 68 °F (USCG, 1999) - Denser than waterwill sink1.3394 g/cu cm at 22 °CDensity: 1.27 at 25 °C1.33 g/cm³1.331 @ -5°C |
| Color/Form | Crystallizes from ethanol as colorless, hygroscopic rhombododecahedra.Colorless crystalline solidColorless, lustrous crystals or white crystalline powderWhite, crystalline powder or colorless, lustrous crystals |
| Solubility | greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)In water, 302,300 mg/L at 25 °CSolubility of methenamine in 100 g of various solvents at 20 °C is: 13.4 g chloroform, 7.25 g in methanol, 2.89 g in absolute ethanol, 0.65 g in acetone, 0.23 g in benzene, 0.14 g in xylene, 0.06 g in ether, and near zero in petroleum ether.At 12 °C, 81.3 g dissolves in 100 g of waterthe solubility decreases slightly with increasing temperature.Freely soluble in waterpractically insoluble in petroleum etherFor more Solubility (Complete) data for METHENAMINE (6 total), please visit the HSDB record page.H2O: 1 M at 20 °C, clear, colorless895 g/L (20 ºC) |
| Flash point | 482 °F (NTP, 1992)250 °C (482 °F) - closed cup250 °C c.c. |
| Melting point | 280 °C (subl.) (lit.) |
| Boiling point | 246.7°C (rough estimate) |
| Bulk density | 600kg/m3 |
| Vapor density | 4.9 (vs air) |
| Vapor pressure | <0.01 mm Hg ( 20 °C) |
| Refractive index | 1.4260 (estimate) |
| Storage conditions | Store below +30°C. |
| Physical state | Solid |
| pKa (acidity coefficient) | 5.1(at 25℃) |
| Color | white |
| Sensitivity | Hygroscopic |
| Merck | 14,5966 |
| Sublimation | 263-295 ºC |
| BRN | 2018 |
| Henry's law constant | 6.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stability | Stable. Incompatible with strong acids, strong oxidizing agents. |
| Cosmetics Ingredients Functions | PRESERVATIVEANTIMICROBIAL |
| Cosmetic Ingredient Review (CIR) | Hexamethylenetetramine (100-97-0) |
| InChI | 1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2 |
| InChIKey | VKYKSIONXSXAKP-UHFFFAOYSA-N |
| SMILES | C1N2CN3CN1CN(C2)C3 |
| LogP (partition coefficient) | -2.18--2 at 20℃ |
| FDA 21 CFR | 175.105176.170176.180177.1210177.1460177.1900177.2410177.2600181.30 |
| Indirect Additives used in Food Contact Substances | HEXAMETHYLENETETRAMINE |
| CAS DataBase Reference | 100-97-0(CAS DataBase Reference) |
| FDA UNII | J50OIX95QV |
| ATC code | J01XX05 |
| NIST Chemistry Reference | Hexamethylenetetramine(100-97-0) |
| EPA Substance Registry System | Hexamethylenetetramine (100-97-0) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS02,GHS07 |
| Signal word | Warning |
| GHS hazard statements | H228-H317 |
| GHS precautionary statements | P210-P240-P241-P261-P280-P302+P352 |
| Hazard symbols | F,Xn,Xi |
| Risk statements (R) | 11-42/43-43 |
| Safety statements (S) | 16-22-24-37 |
| UN transport number | UN 1328 |
| Water hazard class (WGK) | 1 |
| RTECS number | MN4725000 |
| F | 9-23 |
| Autoignition temperature | 770 °F |
| TSCA inventory status | TSCA listed |
| Customs code | 2933 69 40 |
| Hazard class | 4.1Flam. Sol. 2Skin Sens. 1B |
| Packing group | III |
| Storage class | 4.1B - Flammable solid hazardous materials |
| Hazardous substances data | 100-97-0(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 9200 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | WarningH228: Flammable solid [Danger Flammable solids]P210, P240, P241, P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, P370+P378, and P501 (click each P-code to see the statement)H228 (100%): Flammable solid [Danger Flammable solids] |
|---|---|
| Regulatory information | Chemical: 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decaneRegulation (EC) No 1831/2003 (amended)1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)2007/442Status: Active Update: 19-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15907Hexamethylenetetramine: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane: Human health tier II assessment |
| DOT label | Flammable Solid |
| Fire hazards | Special Hazards of Combustion Products: Formaldehyde gas and ammonia may be given off when hot. (USCG, 1999)· Flammable/combustible material.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Fire potential | Combustible. |
| Health hazards | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Exposure may cause skin rash and kidney irritation. Inhalation may cause coughing and shortness of breath. It may cause corrosion of the respiratory tract. Skin contact may cause redness, pain, rashes and burns of the skin. Eye contact may cause redness, pain and blurred vision. Ingestion of this compound may cause urinary tract irritation, digestive disturbances, and severe nephritis which may be fatal. If large amounts are ingested it can cause sore throat, abdominal pain, vomiting, diarrhea, painful and frequent urination, and blood in the urine. Large oral doses can also cause gastrointestinal irritation, albuminuria, hemorrhagic cystitis, mild azotemia, gross hematuria and dysuria, with inflammatory lesions in the renal tubules, renal pelvis, and urinary bladder. It can also cause irritation of the bladder, and nausea. Repeated use can lead to skin sensitization with urticaria or dermatitis. Prolonged contact can cause smarting and reddening of the skin. It can produce an asthma-like condition. Kidney damage has been reported.· Fire may produce irritating and/or toxic gases. |
| Hazards summary | A skin and eye irritantA skin sensitizerMay cause asthma[ICSC] Danger of skin sensitization[MAK] TLV Basis is dermal sensitization. No evidence of increased risk of occupational asthma at concentrations of 0.2-2.6 mg/m3. |
| DOT ID and guide | 1328 133 |
| FDA requirements | Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Methenamine is included in orally administered menstrual drug products. |
| Reactive group | Amines, Phosphines, and Pyridines |
| EC classification | Symbol: F, XnR: 11-42/43S: (2)-16-22-24-37 |
| UN classification | UN Hazard Class: 4.1UN Pack Group: III |
| Fire fighting | Excerpt from ERG Guide 133 [Flammable Solids]:Use water spray, foam, powder. |
| First aid measures | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention . |
| Accidental release measures | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.General First Aid: |
| Safe storage | Separated from strong acids and strong oxidants. Dry. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Fire fighting procedures | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Use water spray to cool unopened containers.Solid streams of water may spread fire. Use water in flooding quantities as fog. Use dry chemical, graphite, or dry earth. |
| Storage conditions | Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. Storage class (TRGS 510): Flammable solid hazardous materials |
| Cleanup methods | Accidental Release Measures: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Avoid breathing dustEnvironmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drainsMethods and materials for containment and cleaning up: Sweep up and shovel. Contain spillage, and then collect with an electrically protected vacuum cleaner or by wetbrushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.Toxic compd can be removed by reverse osmosis. Hexamethyleneamine treated with oxygen in presence of pyrolusite ores to form HCO2H & NaNO3 which can be removed by biol treatment. |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Disposal methods | SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this materialContaminated packaging: Dispose of as unused product. |
| Spillage disposal | Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. |
| Interactions | /In vet use/...in vivo synergism with antimicrobials has been demonstrated.Diuretics, such as...thiazides can alkalinize urine & thus theoretically would limit usefulness of methenamine as well as its mandelate & hippurate salts...Formaldehyde and some sulfonamides (e.g., sulfamethizole, sulfathiazole (not commercially available in the US)) form an insoluble precipitate in acid urinetherefore, methenamine salts should not be administered concomitantly with sulfonamides. |
| Hepatotoxicity | In prospective controlled trials, methenamine was generally well tolerated at conventional doses and no episodes of serum aminotransferase elevations or clinically apparent liver injury were reported. Since its approval and in over 100 years of general use, there have been no reports of clinically apparent liver injury attributable to methenamine. Thus, clinically apparent liver injury from methenamine must be rare if it occurs at all. |
| Ecotoxicity values | LC50Species: Nitocra spinipes (Harpacticoid Copepod) adult, length 0.6-0.8 mmConditions: saltwater, static, 10 °C, pH 7.8, salinity 7 ppt, alkalinity 75 mg/L CaCO3, dissolved oxygen >5 mg/LConcentration: 92500000 ug/L for 96 hr (95% confidence interval: 26800000-305000000 ug/L) /formulation/Species: Alburnus alburnus (Bleak) length 8 cmConcentration: >10000000 ug/L for 96 hr /formulation/Species: Pimephales promelas (Fathead Minnow) 33 days, length 18.8 mm, weight 0.096 gConditions: freshwater, flow through, 25.2 °C, pH 7.8, hardness 44.9 mg/L CaCO3, dissolved oxygen 5.8 mg/LConcentration: 49800000 ug/L for 96 hr (95% confidence interval: 44600000-55600000 ug/L) /99% purity/Species: Cyprinodon variegatus (Sheepshead Minnow)Conditions: saltwater, static, pH 7.7, salinity 20.5 ppt, alkalinity 174 mg/L CaCO3Concentration: 49000000 ug/L for 96 hr (95% confidence interval: 35885000-66908000 ug/L) /formulation/ |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that methenamine is expected to have very high mobility in soil(SRC). The pKa of methenamine is 4.89(3), indicating that this compound will exist partially in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of methenamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.7X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 6.1X10-4 mm Hg(5), and water solubility, 3.02X10+5 mg/L(6). Methenamine is not expected to volatilize from dry soil surfaces based on its vapor pressure(SRC). Various biolodegradation screening studies have observed between 28-100% degradation of methenamine(7) suggesting that biodegradation is an important environmental fate process in soil(SRC). However, part (or most) of the degradation may be explained by hydrolysis to form formaldehyde and ammonia followed by biodegradation with the degradation rate increasing with acidity(7). Hydrolysis is expected to be an important fate process, especially in moist acidic soils. Aqueous hydrolysis half-lives of 13.8 hours and 1.6 hours have been measured at 37.5 °C and pH 5.8 and pH 2 respectively(8).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that methenamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.7X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 6.1X10-4 mm Hg(4), and water solubility, 3.02X10+5 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of -2.18(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Various biolodegradation screening studies have observed between 28-100% degradation of methenamine(8) suggesting that biodegradation is an important environmental fate process in soil(SRC). However, part (or most) of the degradation may be explained by hydrolysis to form formaldehyde and ammonia followed by biodegradation with the degradation rate increasing with acidity(8). Aqueous hydrolysis half-lives of 13.8 hours and 1.6 hours have been measured at 37.5 °C and pH 5.8 and pH 2 respectively(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methenamine, which has a vapor pressure of 6.1X10-4 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase methenamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 45 minutes(SRC), calculated from its rate constant of 5.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase methenamine may be removed from the air by wet and dry deposition(SRC). |
| Food survey values | Methenamine was not detected in Korean retail provolone cheese, glass noodle and tofu snack (detection limit 0.3-1.0 mg/kg)(1). |
| Adverse effects | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Exposure routes | The substance can be absorbed into the body by inhalation of its aerosol and by ingestion. |
| Milk Concentrations | Methenamine is excreted into breast milk. |
| Toxicity summary | On the basis of the animal and clinical data presented in this report, the CIR Expert Panel concludes that Methenamine is safe for cosmetic use at concentrations not to exceed 0.16% in formulation. It cannot be concluded that Methenamine is safe for use in cosmetic products intended to be aerosolized.Safe for use in cosmetics, with qualificationsIDENTIFICATION AND USE: Methenamine is a white or colorless crystalline solid. It is an anti-infective agent. Methenamine hippurate tablets, USP are indicated for prophylactic or suppressive treatment of frequently recurring urinary tract infections when long-term therapy is considered necessary. Non-medical uses include the following: in adhesives, coatings, and sealing compoundsas cross-linking agent for hardening phenol-formaldehyde resin and vulcanizing rubberas corrosion inhibitor for steelas fuel tablets for camping stovesas stabilizer for lubricating and insulating oilsin the chemical detection of metalsin the preservation of hidesas dye fixativefor the manufacture of explosive compoundsantimicrobial food additive. HUMAN EXPOSURE AND TOXICITY: GI distress frequently is caused by doses >500 mg four times a day, even with enteric coated tablets. Painful and frequent micturition, albuminuria, hematuria, and rashes may result from doses of 4 to 8 g/day given for longer than 3-4 weeks. Inhalation may cause asthma-like reactions in previously sensitized individuals. Vapors or solutions have produced skin irritation. Methenamine does not appear to be linked to congenital defects. ANIMAL STUDIES: Studies on rats, mice, cats, and guinea pigs suggest that methenamine is moderately toxic following acute exposure. Mild irritation occurred when a 5% solution of a mixture that contained 40% methenamine was placed on the skin of guinea pigs. In chronic toxicity studies in dogs and rats receiving oral methenamine, gastric and bladder irritation occurred with some hemorrhagic sites and ulceration. Methenamine hippurate has been administered to rats for 12 months and to monkeys for 6 months at dosages equivalent to twice the usual recommended human dosage without evidence of adverse effects. Dogs have received single IV dosages of up to 600 mg/kg of methenamine hippurate without overt toxic effects. |
| Signs and Symptoms | Cough.Redness. Pain.Abdominal pain. Nausea. Vomiting. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of December 17, 2015: http://actor.epa.gov/dashboard/] |
| Effluent Concentrations | Methenamine was identified as a volatile organic compound emitted from various types of furniture coatings(1). |
| FIFRA requirements | Residues of hexamethylenetetramine are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. Use: Preservative. Limit: For use in citrus washing solutions only at not more than 1%.Residues of hexamethylenetetramine are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Stabilizer for carriers in solid pesticide formulations. Limit: None. |
| Atmospheric standards | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Hexamethylenetetramine is produced, as an intermediate or a final product, by process units covered under this subpart. |
| F | 9-23 |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | MN4725000 |
| UN transport number | UN 1328 |
| Customs code | 2933 69 40 |
| Toxicity | LD50 orally in Rabbit: 9200 mg/kg |
| Risk statements (R) | 11-42/43-43 |
| Signal word | Warning |
| GHS pictogram | GHS02,GHS07 |
| Hazard symbols | F,Xn,Xi |
| Safety statements (S) | 16-22-24-37 |
| Hazard class | 4.1Flam. Sol. 2Skin Sens. 1B |
| Storage class | 4.1B - Flammable solid hazardous materials |
| Packing group | III |
| GHS hazard statements | H228-H317 |
| REACH registrations | Active |
| Autoignition temperature | 770 °F |
| GHS precautionary statements | P210-P240-P241-P261-P280-P302+P352 |
| Hazardous substances data | 100-97-0(Hazardous Substances Data) |
Applications & Uses
Uses
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).
Description
Hexamethylenetetramine is a hardener in epoxy resins of the bisphenol A type and can also be used as an anticorrosive agent. It is a sensitizing agent in ceramics workers.
Uses
antibacterial, tuberculostatic
Uses
Used in the treatment of urinary track infection.
Uses
Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction, the Sommelet reaction, and in the Delepine reaction.
General Description
Odorless white crystalline powder or colorless lustrous crystals. Sublimes in a vacuum at about 505° F with some decomposition. Solutions are strong bases (pH of 0.2 molar aqueous solution is 8.4).
Preparation & Synthesis
Preparation
Hexamethylenetetramine (also known as hexamine, hexa or HMT) is prepared from ammonia and formaldehyde: Ammonia is passed into formalin at 20-30C, with agitation. The resulting solution is evaporated under reduced pressure until most of the water is removed and the hexamethylenetetramine crystallizes. Yields of about 95% on both ammonia and formaldehyde can be achieved. Hexamethylenetetramine is a colourless crystalline solid which, on heating, sublimes with decomposition.