Adipic Acid Dihydrazide, Adipyl Hydrazide, Adipohydrazide, Hexanedioic Acid Dihydrazide, ADH, 1071-93-8
ADIPIC ACID DIHYDRAZIDE (ADH)
CAS Number: 1071-93-8
EC Number (EINECS): 213-999-5
Molecular Formula: C₆H₁₄N₄O₂
Molecular Weight: 174.20 g/mol
Chemical Class: Dihydrazide (dicarboxylic acid derivative)
SECTION 1: PRODUCT IDENTIFICATION AND CHEMICAL IDENTITY
| Parameter |
Description |
| Chemical Name (IUPAC) |
Hexanedioic acid dihydrazide |
| Other Names |
Adipic Acid Dihydrazide, Adipohydrazide, Adipohydrazide, Adipyl Hydrazide, Hexanedioic Acid Dihydrazide, ADH |
| CAS Number |
1071-93-8 |
| EC Number (EINECS) |
213-999-5 |
| Molecular Formula |
C₆H₁₄N₄O₂ |
| Molecular Weight |
174.20 g/mol |
| Chemical Class |
Dihydrazide (dicarboxylic acid derivative) |
| Structure |
H₂NNHCO-(CH₂)₄-CONHNH₂ |
| Appearance |
White to off-white crystalline powder |
| Odor |
Mild characteristic |
SECTION 2: PHYSICAL AND CHEMICAL PROPERTIES
| Property |
Value / Range |
| Molecular Formula |
C₆H₁₄N₄O₂ |
| Molecular Weight |
174.20 g/mol |
| Appearance |
White to off-white crystalline powder |
| Odor |
Mild characteristic |
| Melting Point |
~180-183°C (decomposes) |
| Density |
~1.2 g/cm³ |
| Water Solubility (20°C) |
Slightly soluble (~1-2 g/L) |
| Water Solubility (Hot) |
Significantly increases |
| Organic Solvent Solubility |
Soluble in ethanol, methanol, DMSO; insoluble in ether, benzene, chloroform |
| pH (1% aqueous) |
~7-8 (neutral to slightly basic) |
| Flash Point |
~200°C |
| Thermal Decomposition |
> 180°C releases nitrogen oxides (NOₓ) and CO₂ |
| pKa |
~3.0-3.5 |
SECTION 3: SOLUBILITY PROFILE
| Solvent |
Solubility |
Condition |
| Water |
Slightly soluble (~1-2 g/L) |
20°C |
| Water (Hot) |
Soluble (significant increase) |
> 60°C |
| Ethanol |
Soluble |
- |
| Methanol |
Soluble |
- |
| DMSO |
Soluble |
- |
| Acetone |
Partially soluble |
- |
| Ethyl Acetate |
Insoluble |
- |
| Ether |
Insoluble |
- |
| Benzene |
Insoluble |
- |
| Chloroform |
Insoluble |
- |
Critical Note: ADH has low solubility in water at room temperature, but solubility increases significantly with temperature. This property facilitates its use in water-based systems.
SECTION 4: CHEMICAL PROPERTIES AND REACTIONS
| Property |
Description |
| Chemical Class |
Dihydrazide (dicarboxylic acid derivative) |
| Functional Groups |
Two hydrazide groups (-CONHNH₂) |
| Reactivity |
High; reacts with aldehydes and ketones for crosslinking |
| Aldehyde/Ketone Reaction |
Forms Schiff bases (hydrazones) |
| Crosslinking |
Forms network structures in polymers and coatings |
| Thermal Decomposition |
> 180°C releases nitrogen oxides (NOₓ) and CO₂ |
| Hydrolysis |
Hydrolyzes in acidic/basic media to hydrazine and adipic acid |
| Oxidation |
Reacts with oxidizing agents |
4.1. Key Reactions
| Reaction Type |
Description |
| Schiff Base Formation |
With aldehydes/ketones → Hydrazones (crosslinking) |
| Network Formation |
As crosslinker in polymers |
| Epoxy Hardening |
Curing agent for epoxy resins |
| Hydrazide-Azide Conversion |
Intermediate in organic synthesis |
| Hydrolysis |
Acid/base → Hydrazine + Adipic acid |
| Coordination Bonding |
Forms complexes with metal ions |
SECTION 5: MAJOR APPLICATIONS AND END-USES
5.1. Water-Based Coatings and Emulsions (Most Important Application)
| Application |
Function |
Suitability |
| Acrylic Emulsions |
Crosslinker, durability enhancer |
High |
| Water-Based Paints |
Chemical and mechanical resistance enhancer |
High |
| Coatings |
Water and chemical resistance |
High |
5.2. Epoxy Resins
| Application |
Function |
Suitability |
| Epoxy Hardener |
Curing agent |
High |
| Epoxy Modification |
Flexibility and toughness enhancer |
High |
5.3. Adhesives
| Application |
Function |
Suitability |
| Adhesive Formulations |
Chemical stability and bonding strength enhancer |
High |
| Heat-Curing Adhesives |
Crosslinker |
High |
5.4. Textile Processing
| Application |
Function |
Suitability |
| Fabric Coatings |
Abrasion resistance enhancer |
High |
| Textile Auxiliaries |
Durability and stability provider |
High |
5.5. Paper and Polymer Coatings
| Application |
Function |
Suitability |
| Paper Coatings |
Water and chemical resistance |
High |
| Polymer Coatings |
Protective barrier former |
High |
5.6. Specialty Applications
| Application |
Function |
Suitability |
| Organic Synthesis |
As intermediate |
High |
| Polymer Science |
As crosslinker |
High |
| Pigment Dispersions |
As stabilizer |
Moderate |
SECTION 6: INDUSTRY SUITABILITY MATRIX
| Industry |
Suitability |
Explanation |
| Coatings / Paints |
High |
Crosslinker in water-based acrylic emulsions |
| Epoxy Resins |
High |
Hardener and modification agent |
| Adhesives |
High |
Chemical stability and bonding strength enhancer |
| Textiles |
High |
Fabric abrasion resistance enhancer |
| Paper / Packaging |
High |
Water and chemical resistance |
| Polymer Science |
High |
Crosslinker |
| Pharmaceuticals |
Limited |
Potential as intermediate |
| Cosmetics |
Not suitable |
No cosmetic use |
| Food |
Not suitable |
Not approved as food additive |
SECTION 7: OTHER NAMES AND IDENTIFIERS
| Type |
Name / Description |
| IUPAC Name |
Hexanedioic acid dihydrazide |
| Commercial Names |
ADH, Adipohydrazide |
| Synonyms |
Adipic Acid Dihydrazide, Adipyl Hydrazide, Hexanedioic Acid Dihydrazide, Adipohydrazide |
| CAS Number |
1071-93-8 |
| EC Number |
213-999-5 |
| HS Code |
29280090 |
SECTION 8: PRODUCTION METHOD
| Parameter |
Description |
| Method |
Adipic acid + Hydrazine → Adipic Acid Dihydrazide |
| Reaction |
HOOC-(CH₂)₄-COOH + 2 N₂H₄ → H₂NNHCO-(CH₂)₄-CONHNH₂ + 2 H₂O |
| Conditions |
Temperature controlled, anhydrous medium |
| Purification |
Crystallization |
| Purity |
≥ 98% (typical commercial) |
SECTION 9: TOXICOLOGY AND HEALTH EFFECTS
| Parameter |
Value / Description |
| GHS Classification |
Warning |
| Hazard Statements |
H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation) |
| Precautionary Statements |
P261 (Avoid breathing dust), P280 (Wear protective gloves/eye protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water) |
| Oral LD50 (Rat) |
> 5,000 mg/kg (low toxicity) |
| Skin Irritation |
Mild irritant |
| Eye Irritation |
Mild irritant |
| Skin Sensitization |
No data |
| Mutagenicity |
Negative (Ames test) |
| Carcinogenicity |
Not classified |
| Target Organs |
Skin, eyes, respiratory system |
SECTION 10: ECOTOXICOLOGY AND ENVIRONMENTAL BEHAVIOR
| Parameter |
Value / Description |
| Biodegradability |
Potentially biodegradable |
| Bioaccumulation Potential |
Low |
| Water Solubility |
Low-moderate |
| Water Hazard Class (WGK Germany) |
WGK 2 (hazardous to water) |
Ecotoxicological Summary: Limited ecotoxicological data for ADH is available. Due to its low toxicity profile and hydrazide structure, it has potential for biodegradability.
SECTION 11: SAFETY AND STORAGE
| Parameter |
Information |
| Storage Conditions |
Cool, dry, well-ventilated area |
| Temperature |
Room temperature (15 - 30°C) |
| Container |
Tightly closed, inert containers (PE bags, fiber drums) |
| Materials to Avoid |
Strong oxidizers, acids, high heat, moisture |
| Shelf Life |
24 months (under recommended conditions) |
| Packaging |
25 kg bags, fiber drums |
SECTION 12: TRANSPORT INFORMATION
| Parameter |
Information |
| UN Number |
Not regulated (not classified as dangerous goods) |
| Hazard Class |
Not applicable |
| Packing Group |
Not applicable |
| Proper Shipping Name |
Adipic Acid Dihydrazide |
| ADR/RID |
Not regulated |
| IMDG Code |
Not regulated |
| IATA (Air) |
Not regulated |
| Marine Pollutant |
No |
SECTION 13: FIRE-FIGHTING MEASURES
| Parameter |
Information |
| Fire Hazard |
Combustible dust |
| Extinguishing Media |
Water fog, CO₂, dry chemical, foam |
| Special Hazards |
When heated, releases nitrogen oxides (NOₓ), CO₂ |
| Decomposition Products |
Nitrogen oxides (NOₓ), CO₂ |
| Protective Equipment |
Self-contained breathing apparatus (SCBA), full protective clothing |
SECTION 14: ACCIDENTAL RELEASE AND CLEANUP
| Parameter |
Information |
| Personal Protection |
Gloves, safety goggles, dust mask |
| Ventilation |
Increase ventilation |
| Cleanup Methods |
Sweep while preventing dust formation; collect in sealed containers |
| Environmental Precautions |
Prevent entry into drains |
| Waste Disposal |
According to local regulations |
SECTION 15: FIRST AID MEASURES
| Exposure Route |
Action |
| Inhalation |
Move to fresh air. Seek medical attention if symptoms persist. |
| Skin Contact |
Remove contaminated clothing. Wash with soap and plenty of water. |
| Eye Contact |
Rinse with plenty of water for at least 15 minutes. Seek medical attention if irritation persists. |
| Ingestion |
Do NOT induce vomiting. Drink plenty of water. Seek medical attention. |
SECTION 16: REGULATORY INFORMATION
| Region / Authority |
Status |
| EU REACH |
Registered |
| Turkey KKDİK |
Registration required |
| USA TSCA |
Listed |
| EINECS |
213-999-5 |
SECTION 17: SUMMARY AND CRITICAL WARNINGS
Product Summary
| Parameter |
Value |
| Product |
Adipic Acid Dihydrazide (ADH) |
| CAS |
1071-93-8 |
| Appearance |
White to off-white crystalline powder |
| Melting Point |
180-183°C |
| Water Solubility |
Slightly soluble (increases with temperature) |
| Key Industries |
Coatings, epoxy resins, adhesives, textiles |
CRITICAL WARNINGS
-
Crosslinker for Water-Based Systems: ADH is an effective crosslinker for water-based acrylic emulsions, paints, and coatings. It reacts with aldehydes and ketones to form network structures, providing durability and chemical resistance.
-
Epoxy Hardener: Used as a curing agent for epoxy resins. Offers flexibility and toughness advantages compared to alternative hardeners.
-
Water Solubility: ADH has low solubility in water at room temperature (~1-2 g/L) but solubility increases significantly with temperature. This enables its use in water-based systems.
-
Bifunctional Structure: Contains two hydrazide groups, maximizing crosslinking and network-forming capacity. High crosslinking capacity provides long-term stability in coatings and adhesives.
-
Usage Conditions: Due to low water solubility, formulation may require solvent addition or temperature adjustment. Typically used as a solution or dispersion.
-
Hydrazide Reactivity: Hydrazide groups show high reactivity with aldehydes and ketones. This enables rapid and effective crosslinking in coating and adhesive formulations.
-
Limited Applications: Not approved for direct use in food, cosmetics, or pharmaceutical industries. Use only in technical and industrial applications.
-
Thermal Stability: Stable up to 180°C, decomposes above this temperature releasing nitrogen oxides (NOₓ) and CO₂. Appropriate protective equipment required in case of fire.
IMPORTANT DISCLAIMER: This Technical Data Sheet (TDS) is for informational purposes only and is based on available technical data. The user is solely responsible for determining the product's suitability for their specific application and for complying with all applicable local, national, and international regulations. For complete safety, storage, handling, transportation, disposal, and regulatory compliance information, always refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Users are responsible for testing the product in their own processes and applications. All local, national, and international regulations must be followed when working with Adipic Acid Dihydrazide.
