化工社化工社 化学情報印刷レポート · 研究参考用
ヘキサメチレンテトラミン
ヘキサメチレンテトラミン · ヘキサミン · 1,3,5,7-テトラアザアダマンタン · シスタミン【利尿薬】 · シストゲン · メテナミン · ウロトロピン · アミノホルム
識別子と物理属性
| CAS No. | 100-97-0 |
|---|---|
| 分子式 | C6H12N4 |
| 平均分子量 | 140.19 g/mol |
| 単同位体質量 | 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 |
| 現地名 | ヘキサメチレンテトラミン |
化学・物理的性質
| XLogP | 0.3 |
|---|---|
| 極性表面積 | 13 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 0 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 84.8 |
| 物質分類 | Nitrogen Compounds -> Amines, AliphaticPharmaceutical |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antibiotics |
| 化粧品 | 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 |
| 農薬 | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approvedBactericides |
| LogP（分配係数） | log Kow = -2.18 at pH 7-9, 20 °C-2.84 |
| 臭い | OdorlessPractically odorless無臭 |
| 密度 | 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 |
| 溶解度 | 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: 1M at20℃、透明、無色895g/L（20℃） |
| 引火点 | 482 °F (NTP, 1992)250 °C (482 °F) - closed cup250 °C c.c. |
| 融点 | 280 °C (subl.) (lit.) |
| 沸点 | 246.7°C (rough estimate) |
| 蒸気密度 | 4.9 (vs air) |
| 蒸気圧 | <0.01 mm Hg ( 20 °C) |
| 屈折率 | 1.4260 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 5.1(at 25℃) |
| 色 | 白い |
| Merck | 14,5966 |
| BRN | 2018 |
| ヘンリー定数 | 6.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。強酸、強酸化剤とは相容れない。 |
| 化粧品成分の機能 | 防腐剤抗菌剤 |
| 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（分配係数） | -2.18--2 at 20℃ |
| CAS データベース | 100-97-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Hexamethylenetetramine(100-97-0) |
| EPAの化学物質情報 | Hexamethylenetetramine (100-97-0) |
化学的特性
White or almost white, crystalline powder or colourless crystals.
安全性と法規制
| GHS 分類 | 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] |
|---|---|
| 規制情報 | 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 |
| その他の安全情報 | IMAP assessments - 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane: Human health tier II assessment |
| 輸送ラベル（DOT） | Flammable Solid |
| 火災危険 | 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. |
| 火災の可能性 | Combustible. |
| 健康有害性 | 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. |
| 有害性の概要 | 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. |
| 輸送番号・ガイド（DOT） | 1328 133 |
| FDA 要件 | 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. |
| 反応性グループ | Amines, Phosphines, and Pyridines |
| EC 分類 | Symbol: F, XnR: 11-42/43S: (2)-16-22-24-37 |
| UN 分類 | UN Hazard Class: 4.1UN Pack Group: III |
| 消火 | Excerpt from ERG Guide 133 [Flammable Solids]:Use water spray, foam, powder. |
| 応急処置措置 | 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 . |
| 漏出応急措置 | · 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. |
| 応急処置 | 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: |
| 安全保管 | Separated from strong acids and strong oxidants. Dry. |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 消火手順 | 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. |
| 保管条件 | Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. Storage class (TRGS 510): Flammable solid hazardous materials |
| 清掃方法 | 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. |
| 非火災時の漏出対応 | 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. |
| 処分方法 | 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. |
| 漏出処分 | 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. |
| 相互作用 | /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. |
| 生態毒性値 | 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/ |
| 環境中動態 | 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). |
| 食品調査値 | Methenamine was not detected in Korean retail provolone cheese, glass noodle and tofu snack (detection limit 0.3-1.0 mg/kg)(1). |
| 有害作用 | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its aerosol and by ingestion. |
| Milk Concentrations | Methenamine is excreted into breast milk. |
| 毒性の概要 | 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 要件 | 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. |
| 大気基準 | 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 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | MN4725000 |
| 輸送番号（UN） | UN 1328 |
| 毒性 | LD50 orally in Rabbit: 9200 mg/kg |
| PRTR法 | 第一種指定化学物質 |
| 税関コード | 2933 69 40 |
| 危険文句（R） | 11-42/43-43 |
| 化審法 | (5)-1155 |
| 安衛法 | 変異原性物質 |
| 危険表示 | F,Xn,Xi |
| 安全措置（S） | 16-22-24-37 |
| 危険等級 | 4.1Flam. Sol. 2Skin Sens. 1B |
| 包装等級 | III |
| 自然発火温度 | 770 °F |
| 環境リスク評価 | ヘキサメチレンテトラミン(100-97-0) |
| 貯蔵分類 | 4.1B - Flammable solid hazardous materials |
| 有害物質データ | 100-97-0(Hazardous Substances Data) |
用途
解説
ヘキサメチレンテトラミン．ヘキサミン，ウロトロピンともいう．ホルムアルデヒドと計算量のアンモニア水をまぜてつくる．結晶性粉末．263 ℃ で昇華する．水，エタノール，クロロホルムに可溶，ベンゼン，アセトン，エーテルに難溶．酸性水溶液中では原料に分解し，低温で濃硝酸と反応して爆薬トリメチレントリニトロアミンを，還元によりメチルアミンを生じる．利尿剤，尿路消毒薬，ゴムの加硫促進剤，ビスマス，銀などの分析試薬として用いられる．
用途
泌尿器官系において、抗菌作 用を示すとされています。
用途
泌尿器官系において、抗菌作 用を示すとされています。
用途
pH緩衝剤。医薬原料。合成樹脂硬化促進剤、ゴム加硫促進剤。
説明
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.
使用
Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction, the Sommelet reaction, and in the Delepine reaction.
一般的な説明
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).
使用用途
ヘキサメチレンテトラミンは、治療薬に使用可能です。具体的には、適応症や膀胱炎、尿路感染症などが挙げられます。作用機序は、まずヘキサメチレンテトラミンが尿中でホルムアルデヒドになります。 そのホルムアルデヒドは、尿路で防腐性を有するため、尿路防腐剤として利用可能です。また、食品用の防腐保存剤も使用用途として挙げられます。海外では、チーズやイクラに添加されて使用されていますが、日本では食品防腐保存剤として用いられていません。
製法・合成法
製造方法
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.
純化方法
It is soluble in H2O (67%), CHCl3 (10%), EtOH (8%) and Et2O (0.3%), and a 0.2M solution has a pH of 8.4. Dissolve it in hot absolute EtOH (reflux, Norit), filter using a heated funnel, cool at room temperature first, then in ice. Wash the crystals with cold Et2O, dry them in air or under a vacuum. A further crop can be obtained by adding Et2O to the filtrate. It sublimes above 260o without melting. The picrate has m 179o(dec). [pK2 0 4.85: Reilley & Schmid Anal Chem 30 947 1958, pK2 0 6.30: Pummerer & Hofmann Chem Ber 56 1255 1923.] [Beilstein 26 I 306, 26 II 200, 26 III/IV 1680.]