Hexamethylenetetramine, Heksametilen Tetramin, Methenamine, Hexamine, Methenamine, Urotropine, Hexamethylene Tetramine, E239, HMT, HMTA, 100-97-0

HEXAMETHYLENETETRAMINE (HMTA, HEXAMINE)

PRODUCT IDENTIFICATION INFORMATION

CHEMICAL STRUCTURE

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    Hexamethylenetetramine (HMTA)
    Tetrahedral Cage-like Heterocyclic Structure
    (Adamantane-like Cage)

Molecular Formula: C₆H₁₂N₄
SMILES: C1N2CN3CN1CN(C2)C3
InChI: InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
Structure: Tetrahedral cage-like heterocyclic structure (adamantane-like)
Note: Product is obtained by controlled condensation of ammonia with formaldehyde, followed by crystallization/drying. Weak base; forms complexes with many metal ions (Bi, Co, Cu, Mn, Mg, Li, Pt, In, Th, etc.)

SECTION 1: CHEMICAL IDENTITY AND DEFINITION

SECTION 2: PHYSICAL AND CHEMICAL PROPERTIES

SECTION 3: CHEMICAL PROPERTIES AND REACTIVITY

SECTION 4: COMPARISON OF HEXAMETHYLENETETRAMINE GRADES

SECTION 5: PRODUCTION METHODS

Method 1: Condensation of Ammonia and Formaldehyde (Main Industrial Method)

• Reaction: 4NH₃ + 6HCHO → C₆H₁₂N₄ + 6H₂O

• Description: Ammonia and formaldehyde are reacted in controlled conditions; Hexamethylenetetramine is formed through condensation; Product is crystallized, separated, and dried; Most common industrial production method

Method 2: Gas Phase Reaction

• Process: Ammonia gas + Formaldehyde gas → HMTA

• Description: Gaseous ammonia and formaldehyde are reacted in the gas phase; Solid HMTA is formed; Used for specialized applications

Method 3: Crystallization Purification

• Process: Crude HMTA → Dissolve in water → Filtration → Crystallization → Drying → Pure HMTA

• Description: Crude product is dissolved in water; Impurities are removed by filtration; Crystallization yields high-purity product; Drying at controlled temperature

Method 4: Controlled Crystallization for Particle Size Control

• Process: HMTA solution → Controlled cooling → Crystallization → Milling/Classifying → Specific particle size

• Description: Crystallization conditions are controlled to achieve specific particle size; Used for applications requiring specific particle size distribution

SECTION 6: FUNCTIONAL PROPERTIES AND MECHANISM OF ACTION

SECTION 7: MAIN APPLICATION AREAS

SECTION 8: QUALITY SPECIFICATIONS (TECHNICAL GRADE)

SECTION 9: TOXICOLOGICAL PROFILE

SECTION 10: GHS CLASSIFICATION AND LABELING

GHS Classification (Compliant with CLP and UN GHS):

Signal Word: WARNING

Hazard Pictograms: GHS02 (Flame), GHS07 (Exclamation Mark)

Hazard Statements (H-Codes):

Precautionary Statements (P-Codes):

NFPA 704 Hazard Classification:

SECTION 11: PRECAUTIONARY STATEMENTS (P-CODES)

SECTION 12: FIRST AID MEASURES

SECTION 13: FIREFIGHTING MEASURES

SECTION 14: STORAGE AND SHELF LIFE

SECTION 15: PACKAGING OPTIONS

SECTION 16: TRANSPORT INFORMATION

SECTION 17: REGULATORY STATUS

SECTION 18: OTHER NAMES AND SYNONYMS

SECTION 19: SUMMARY TABLE

SECTION 20: CRITICAL WARNINGS AND BEST PRACTICES

CRITICAL WARNINGS:

• Flammable solid (H228). Keep away from heat, sparks, open flames, and hot surfaces. No smoking.

• May cause an allergic skin reaction (H317). Skin sensitizer. Avoid skin contact.

• May cause respiratory irritation (H335). Avoid inhalation of dust.

• Releases formaldehyde under heat or acidic conditions. Formaldehyde is a sensitizer and potential carcinogen. Use with adequate ventilation.

• Dust may form explosive mixtures with air. Use explosion-proof equipment. Avoid dust generation.

• Incompatibilities: Keep away from strong acids (hydrolysis, formaldehyde release), strong oxidizing agents, and nitrating agents.

• Slightly hygroscopic. Protect from moisture.

• Food additive (E239): Use as food preservative is now banned or highly restricted in most jurisdictions. Verify local food regulations before any food contact use.

• Pharmaceutical use: Only pharmaceutical grade should be used for medicinal applications. Industrial grade must NOT be used for pharmaceutical purposes.

• Hygiene Requirement: Contaminated clothing should not be allowed out of the workplace.

• Storage Temperature: Keep below 30°C in a cool, dry, well-ventilated area.

BEST PRACTICE RECOMMENDATIONS:

• Phenolic Resin Curing: Use stabilized grade (10-15 parts per 100 parts resin) for novolac curing; Provides hardness, thermal resistance, and chemical resistance; Press at 150-180°C; HMTA releases formaldehyde under heat for crosslinking.

• Fuel Tablets: Use unstabilized grade; Press into tablets with optional binder (1-2 parts paraffin) for mechanical strength; Burn in well-ventilated area; Clean, hot, low-smoke flame.

• Rubber Vulcanization: Use stabilized grade (1-2 parts) as H-accelerator in SBR/BR compounds; Curing temperature ~150°C; Provides faster and more uniform crosslinking.

• Organic Synthesis: Use unstabilized grade for synthesis of pharmaceuticals, plastic intermediates, and explosives (RDX, HMX); Handle with appropriate safety precautions.

• Pharmaceutical Applications: Use pharmaceutical grade (methenamine hippurate/mandelate); Must meet USP/EP standards; Used as urinary antiseptic; Only pharmaceutical grade for medical use.

• Handling: Use in well-ventilated areas or under fume hoods; Avoid dust generation; Use explosion-proof equipment; Wear protective gloves, safety goggles, and appropriate respiratory protection; Ground/bond equipment to prevent static discharge.

• Personal Protective Equipment: Wear impermeable gloves (nitrile, neoprene), chemical safety goggles, full-face shield, protective clothing, and NIOSH-approved dust mask/respirator. Use explosion-proof equipment.

• Hygiene: Do not eat, drink, or smoke when using; Wash hands thoroughly after handling; Do not take contaminated working clothes home; Shower at the end of the work shift.

• Storage: Store in tightly closed, properly labeled containers in dry conditions; Keep below 30°C; Keep away from heat, ignition sources, acids, and oxidizing agents; Store in explosion-proof area; Ground/bond equipment.

• Spill Response: Avoid raising dust; Use explosion-proof vacuum equipment; Wear full PPE; Sweep spilled substance into covered containers; Do not allow to enter drains or waterways; Place in properly labeled closed containers; Use explosion-proof electrical equipment.

• Disposal: Dispose of in accordance with local, regional, and national regulations; Do not discharge into sewers or water sources; HMTA is regulated as flammable solid waste.

FORMALDEHYDE RELEASE WARNING:

HMTA releases formaldehyde under specific conditions:

• Acidic Conditions: Hydrolyzes to formaldehyde and ammonia

• Heating: Releases formaldehyde during curing reactions

• Health Risk: Formaldehyde is a known sensitizer and potential carcinogen

• Precaution: Use with adequate ventilation; Monitor formaldehyde levels; Use appropriate respiratory protection

FORMULATION EXAMPLES:

Phenolic Novolac Molding Compound:

• Novolac resin: 100 parts

• HMTA (stabilized): 10-15 parts (curing agent)

• Fillers (wood flour, minerals): 100-200 parts

• Lubricant: 1-2 parts

• Mix, mill, and press at 150-180°C; HMTA releases formaldehyde upon heating for crosslinking

Rubber Vulcanization (SBR/BR Compound):

• SBR 1502: 100 parts

• Carbon black: 50 parts

• Zinc oxide: 3 parts

• Stearic acid: 2 parts

• Sulfur: 2 parts

• HMTA (H-accelerator): 1-2 parts

• Typical curing temperature: 150°C; HMTA provides faster and more uniform crosslinking

Simple Fuel Tablet:

• HMTA (unstabilized): 100 parts

• Paraffin/binder (optional): 1-2 parts (for mechanical strength)

• Tablet press; Ignite in well-ventilated area

STABILIZED VS. UNSTABILIZED SELECTION GUIDE:

LEGAL DISCLAIMER:

The information provided in this document is based on our current knowledge and experience and is presented in good faith. However, as all conditions of use are beyond our control, this document does not constitute a binding specification or warranty. This Technical Data Sheet is for informational purposes only. Users are responsible for testing suitability for their own applications. For complete safety, storage, handling, transportation, waste, and regulatory compliance information, please refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier.