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Send EmailGlutaral, Glutaraldehyde, Glutardialdehyde, Pentanedial, Pentane, 111-30-8
Glutaral / Glutardialdehyde / 1,5-Pentanedial / Pentane-1,5-dial
CAS Number: 111-30-8
EC Number: 203-856-5
| Property | Information |
|---|---|
| Chemical Name | Glutaraldehyde |
| Other Names | Glutaral, Glutardialdehyde, 1,5-Pentanedial, Glutaric Dialdehyde, Pentane-1,5-dial, Glutaric Aldehyde |
| Chemical Formula | C₅H₈O₂ (OHC(CH₂)₃CHO) |
| Molecular Weight | 100.12 g/mol |
| CAS Number | 111-30-8 |
| EC Number (EINECS) | 203-856-5 |
| Appearance | Colorless to pale yellow clear liquid |
| Odor | Pungent, characteristic aldehyde odor |
| Property | Value |
|---|---|
| Physical State (20°C) | Liquid |
| Appearance | Colorless to slightly yellow clear liquid |
| Odor | Pungent, sharp |
| Molecular Weight | 100.12 g/mol |
| Density (20°C) | 1.06 - 1.12 g/cm³ |
| Specific Gravity (20/20°C) | 1.06 - 1.12 |
| Melting Point / Freezing Point | -14°C (7°F) |
| Boiling Point | 187-189°C (decomposes) |
| Flash Point | Not applicable (noncombustible) |
| Vapor Pressure (20°C) | 17 mmHg |
| Vapor Density (air=1) | 3.38 |
| Solubility in Water | Miscible |
| Solubility in Organic Solvents | Miscible with ethanol, benzene, ether |
| pH (50% aqueous solution) | 3.0 - 5.0 |
| Refractive Index (nD25) | 1.43300 |
| Property | Information |
|---|---|
| Chemical Formula | C₅H₈O₂ |
| Molecular Weight | 100.12 g/mol |
| Chemical Class | Aliphatic dialdehyde |
| Functional Group | Two aldehyde groups (-CHO) (terminal positions) |
| Stability | Stable under normal conditions; polymerizes in water at alkaline pH |
| Reaction with Water | Miscible; polymerization occurs at alkaline pH via aldol condensation |
| Reaction with Alcohols | Hemiacetal/acetal formation |
| Reaction with Amines | Schiff base formation; crosslinking of proteins |
| Reaction with Proteins | Crosslinks lysine residues (amine-reactive homobifunctional crosslinker) |
| Incompatible Materials | Strong oxidizers, strong bases, amines (alkaline solutions react with alcohols, ketones, amines, hydrazines & proteins) |
Polymerization Reaction (Alkaline pH):
n OHC-(CH₂)₃-CHO —[OH⁻]—> α,β-unsaturated poly-glutaraldehyde (aldol condensation)
Protein Crosslinking (Schiff Base Formation):
R-NH₂ (protein lysine) + OHC-(CH₂)₃-CHO + H₂N-R' → R-N=CH-(CH₂)₃-CH=N-R' + 2 H₂O
| Method | Description |
|---|---|
| Dihydrofuran Synthesis (Industrial Standard) | 2,5-Dihydrofuran + H₂O → Glutaraldehyde |
| Acrolein Route | Acrolein + Vinyl Ether → Glutaraldehyde |
| Cyclopentadiene Route | Dicyclopentadiene → Glutaraldehyde (oxidation/hydrolysis) |
| Purification | Distillation under reduced pressure |
| Commercial Forms | 25%, 50% aqueous solutions (most common); technical grade |
Typical Commercial Concentrations:
| Grade | Concentration | Application |
|---|---|---|
| Low Concentration | 2-5% | Disinfection, sterilization |
| Technical Grade | 25% ± 0.5% | Industrial applications |
| High Concentration | 50% ± 0.5% | Crosslinking, fixation, synthesis |
| Form | Concentration | Description | Applications |
|---|---|---|---|
| Aqueous Solution | 25% w/w | Colorless liquid | General industrial, water treatment |
| Aqueous Solution | 50% w/w | Colorless to pale yellow liquid | Crosslinking, fixation, microscopy |
| Activated Solution | 2-3.4% (alkaline) | Buffered, pH 7.5-8.5 | Medical instrument sterilization |
| Technical Grade | 50% | Contains free formaldehyde <0.1% | Industrial synthesis |
Typical Specifications (50% Solution):
| Parameter | Specification | Test Method |
|---|---|---|
| Assay (GC) | 50% ± 0.5% | Gas Chromatography |
| Appearance | Clear, colorless to pale yellow | Visual |
| pH (25°C) | 3.0 - 5.0 | Potentiometric |
| Specific Gravity (20/20°C) | 1.12 - 1.13 | Hydrometer |
| Formaldehyde Content | Free (typically 0%) | Colorimetric |
| Heavy Metals (as Pb) | ≤ 10 ppm | ICP |
| Residue on Evaporation | ≤ 0.5% | Gravimetric |
| Application | Function |
|---|---|
| Endoscope Disinfection | High-level disinfectant (2-3.4% activated solution) |
| Dialyzer Sterilization | Reuse of hemodialysis equipment |
| Surgical Instrument Sterilization | Cold sterilization (cannot be heat-sterilized) |
| Respiratory Therapy Equipment | Disinfection of spirometry tubing, anesthesia equipment |
| Laparoscopic Instruments | Reuse of disposable plastic trocars |
| Application | Function |
|---|---|
| Electron Microscopy Fixative | Preserves cellular ultrastructure (standard fixative) |
| Tissue Fixation | Histology, immunohistochemistry |
| Cell Fixation | Before SDS-PAGE, staining, flow cytometry |
| Enzyme Immobilization | Crosslinks enzymes to solid supports |
| Protein Crosslinking | Amine-reactive homobifunctional crosslinker |
| Nucleic Acid Conjugation | Couples biotin hydrazides, fluorescent hydrazides to DNA |
| Application | Function |
|---|---|
| Chrome Tanning Auxiliary | Pretanning agent, crosslinking agent |
| Wet-Blue Tanning | Stabilizes collagen fibers |
| Leather Finishing | Improves physical properties |
| Application | Function |
|---|---|
| H₂S Scavenger | Removes hydrogen sulfide from oil & gas fields |
| Cooling Water Treatment | Biocide for slime control |
| Oilfield Injection Water | Bacterial control |
| Paper Mill Biocide | Slime control in pulp and paper processing |
| Application | Function |
|---|---|
| Poly(vinyl alcohol) Crosslinking | Gel formation, water resistance |
| Carboxymethyl Cellulose (CMC) Crosslinking | Viscosity modification |
| Cellulose Ethers Crosslinking | Water absorbency control |
| Gelatin Crosslinking | Hardening, stability improvement |
| Polyheptapeptide Crosslinking | Biomaterial applications |
| Application | Function |
|---|---|
| Pharmaceutical Intermediates | Synthesis of various drug compounds |
| Pesticide Intermediates | Agricultural chemical synthesis |
| Dye Intermediates | Synthetic dye production |
| Resin Intermediate | Polymer synthesis |
| Application | Function |
|---|---|
| Embalming Fluid | Tissue preservation (historical/educational) |
| Biological Specimen Preservation | Museum specimens, anatomical preparations |
| Application | Function |
|---|---|
| Viral Wart Treatment | Keratolytic agent (topical) |
| Marine Antifoulant | Prevents biofouling on ship hulls |
| Tissue Hardener | Histological preparations |
| Biocide in Adhesives | Preservative function |
| Parameter | Specification | Test Method |
|---|---|---|
| Assay (as C₅H₈O₂) | 50% ± 0.5% | GC |
| Appearance | Clear, colorless to pale yellow liquid | Visual |
| pH (50% solution) | 3.0 - 5.0 | ASTM E70 |
| Specific Gravity (20/20°C) | 1.12 - 1.13 | ASTM D891 |
| Refractive Index (nD25) | 1.43300 | Refractometry |
| Acidity (as Acetic Acid) | ≤ 0.5% | Titration |
| Residue on Evaporation | ≤ 0.5% | Gravimetric |
| Formaldehyde (Free) | ≤ 0.1% | Colorimetric |
| Heavy Metals (as Pb) | ≤ 10 ppm | ICP |
| Iron (Fe) | ≤ 5 ppm | ICP |
Low Concentration Grade Specifications (25% Solution):
| Parameter | Specification |
|---|---|
| Assay | 25% ± 0.5% |
| pH | 3.0 - 5.0 |
| Specific Gravity | ~1.06 |
| Parameter | Information |
|---|---|
| Storage Conditions | Cool (15-30°C), dry, well-ventilated area; protect from sunlight |
| Container Requirements | UN approved plastic drums (HDPE), tightly closed |
| Protect from | Strong oxidizers, strong bases, heat, freezing (freezing point -14°C) |
| Shelf Life | 6-12 months (unopened containers at room temperature) |
| Stability Note | Polymerizes at alkaline pH; stable at acidic pH (3-5) |
| Incompatible Materials | Strong oxidizers, strong bases, amines, alcohols (in alkaline conditions) |
| Packaging Options | 25 kg drum, 220 kg UN approved plastic drum, 1,100 kg IBC, 17,600 kg (FCL container) |
Handling Notes:
Store in tightly closed containers to prevent oxidation
Do not freeze (may cause phase separation; warm to room temperature and mix if frozen)
Alkaline solutions (activated glutaraldehyde) have reduced stability (14-28 days)
Use only in well-ventilated areas
Avoid contact with skin, eyes, and clothing
| Hazard Class | Category |
|---|---|
| Acute Toxicity (Oral) | Category 4 (H302) |
| Acute Toxicity (Inhalation) | Category 3 (H331) |
| Skin Corrosion/Irritation | Category 1 (H314) |
| Eye Damage | Category 1 (H318) |
| Skin Sensitization | Category 1 (H317) |
| Respiratory Sensitization | Category 1 (H334) |
| Acute Aquatic Toxicity | Category 1 (H400) |
| Chronic Aquatic Toxicity | Category 3 (H412) |
| Code | Statement |
|---|---|
| H302 | Harmful if swallowed |
| H314 | Causes severe skin burns and eye damage |
| H317 | May cause an allergic skin reaction |
| H318 | Causes serious eye damage |
| H331 | Toxic if inhaled |
| H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
| H400 | Very toxic to aquatic life |
| H412 | Harmful to aquatic life with long lasting effects |
| Code | Statement |
|---|---|
| P260 | Do not breathe mist/vapors/spray |
| P280 | Wear protective gloves, protective clothing, eye protection, face protection |
| P284 | Wear respiratory protection |
| P301+P330+P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting |
| P302+P352 | IF ON SKIN: Wash with plenty of water |
| P304+P340 | IF INHALED: Remove person to fresh air and keep comfortable for breathing |
| P305+P351+P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing |
| P310 | Immediately call a POISON CENTER or doctor |
| P342+P311 | If experiencing respiratory symptoms: Call a POISON CENTER or doctor |
| Parameter | Value |
|---|---|
| Oral LD50 (rat, 50% solution) | 2.38 mL/kg (approx. 2,500 mg/kg) |
| Dermal LD50 (rabbit, 50% solution) | 2.56 mL/kg (approx. 2,700 mg/kg) |
| Inhalation LC50 (rat) | Toxic if inhaled |
| Skin Corrosion | Causes severe burns |
| Eye Damage | Causes serious eye damage |
| Skin Sensitization | Yes – allergic skin reactions |
| Respiratory Sensitization | Yes – occupational asthma reported |
| Mutagenicity | Limited evidence |
| Carcinogenicity | Not classified as carcinogenic (IARC: Not listed) |
Health Effects:
| Exposure | Effect |
|---|---|
| Acute (Inhalation) | Respiratory tract irritation, coughing, wheezing, asthma-like symptoms, pulmonary edema |
| Acute (Skin Contact) | Severe burns, blistering, dermatitis, allergic contact dermatitis |
| Acute (Eye Contact) | Severe burns, corneal damage, potential blindness |
| Acute (Ingestion) | Severe gastrointestinal burns, nausea, vomiting |
| Chronic | Occupational asthma, contact dermatitis, respiratory sensitization |
Occupational Exposure Limits:
| Agency | Limit |
|---|---|
| NIOSH REL | Ceiling 0.2 ppm (0.8 mg/m³) |
| OSHA PEL | Not established |
| ACGIH TLV | Ceiling 0.1 ppm (proposed) |
| Exposure Route | Action |
|---|---|
| Inhalation | Remove to fresh air. Administer oxygen if breathing difficulty. Seek immediate medical attention. |
| Skin Contact | Remove contaminated clothing. Wash with soap and plenty of water for at least 15 minutes. Seek medical attention. |
| Eye Contact | Rinse immediately with plenty of water for at least 15 minutes. Remove contact lenses. Seek immediate medical attention. |
| Ingestion | Do NOT induce vomiting. Rinse mouth. Drink water. Seek immediate medical attention. |
| Parameter | Information |
|---|---|
| Fire Hazard | Noncombustible liquid |
| Extinguishing Media | Water spray, CO₂, dry chemical powder, alcohol-resistant foam |
| Special Hazards | Thermal decomposition produces toxic gases (CO, CO₂, aldehydes) |
| Protective Equipment | Self-contained breathing apparatus (SCBA), full protective clothing |
| Parameter | Information |
|---|---|
| Aquatic Toxicity | Very toxic to aquatic life (H400) |
| Persistence | Readily biodegradable |
| Bioaccumulation | Low potential |
| Mobility in Water | High (miscible) |
| Waste Disposal | Dispose according to local regulations. Deactivate with sodium bisulfite before disposal. |
| Parameter | Information |
|---|---|
| UN Number | 3265 |
| Hazard Class | 8 (Corrosive substance) |
| Packing Group | III |
| Proper Shipping Name | CORROSIVE LIQUID, ACIDIC, ORGANIC, N.O.S. (Glutaraldehyde) |
| Marine Pollutant | Yes |
| ADR/RID Label | 8 |
| EMS | F-A, S-B |
| Region | Status |
|---|---|
| EU | REACH registered; authorized for biocidal use |
| USA (TSCA) | Listed |
| Canada (DSL) | Listed |
| Australia (AICS) | Listed |
| Japan (ENCS) | Listed |
| Korea (KECL) | Listed |
| China (IECSC) | Listed |
FDA Compliance: Approved for use as sterilant for medical devices (510(k) cleared)
EPA Registration: Registered as antimicrobial pesticide
| Name |
|---|
| Glutaral |
| Glutardialdehyde |
| 1,5-Pentanedial |
| Pentane-1,5-dial |
| Glutaric Dialdehyde |
| Glutaric Aldehyde |
| Glutaric Acid Dialdehyde |
| 1,3-Diformylpropane |
Trade Names:
| Trademark | Manufacturer |
|---|---|
| Cidex | Johnson & Johnson |
| Glutarol | Dermal |
| Sonacide | Wyeth-Ayerst |
| Ucarcide | Union Carbide |
| Verucasep | Galen |
| Verutal | Stiefel |
Database Identifiers:
| Database | Identifier |
|---|---|
| CAS | 111-30-8 |
| EC | 203-856-5 |
| MDL | MFCD00007025 |
| PubChem CID | 3485 |
| RTECS | MA2450000 |
| UN | 3265 |
| Beilstein | 605390 |
| Industry | Applications | Typical Concentration |
|---|---|---|
| Healthcare | Endoscope sterilization, instrument disinfection | 2-3.4% (alkaline) |
| Research | Electron microscopy fixative, protein crosslinking | 2-25% |
| Leather | Tanning agent, chrome auxiliary | 25% |
| Oil & Gas | H₂S scavenger, biocide | 25-50% |
| Water Treatment | Cooling water biocide, slime control | 25% |
| Paper | Slime control, paper strength | 25% |
| Polymers | Crosslinking agent (PVA, CMC, gelatin) | 5-25% |
| Pharma | Pharmaceutical intermediate | 50% |
| Embalming | Tissue preservation | 5-25% |
Glutaraldehyde (C₅H₈O₂, CAS 111-30-8) is a colorless to pale yellow liquid with a pungent odor. It is an aliphatic dialdehyde that is fully miscible with water and organic solvents. As an amine-reactive homobifunctional crosslinker, it is widely used for protein crosslinking, tissue fixation in electron microscopy, and as a high-level disinfectant for medical instruments. The largest applications are medical device sterilization (~40%) followed by leather tanning, water treatment, and biological research.
| Property | Value |
|---|---|
| Appearance | Colorless to pale yellow liquid |
| Molecular Weight | 100.12 g/mol |
| Boiling Point | 187-189°C (decomposes) |
| Melting Point | -14°C |
| Density | 1.06-1.12 g/cm³ |
| Solubility | Miscible with water |
| pH (50% solution) | 3.0-5.0 |
| Primary Use | Sterilization, crosslinking, fixation |
| Industry | Applications |
|---|---|
| Healthcare | Endoscope sterilization, high-level disinfection |
| Biological Research | Electron microscopy fixative, protein crosslinking |
| Leather Tanning | Collagen crosslinking, chrome tanning auxiliary |
| Oil & Gas | H₂S scavenger, biocide for injection water |
| Water Treatment | Cooling water biocide, slime control |
| Polymers | Crosslinking agent for PVA, CMC, gelatin |
CORROSIVE: Causes severe skin burns and eye damage (H314)
TOXIC: Toxic if inhaled; harmful if swallowed (H331, H302)
SENSITIZER: May cause allergic skin and respiratory reactions (H317, H334)
ENVIRONMENTAL HAZARD: Very toxic to aquatic life (H400)
USE PPE: Chemical goggles, face shield, nitrile gloves, protective clothing
USE VENTILATION: Work in fume hood or well-ventilated area
NIOSH REL: Ceiling 0.2 ppm (0.8 mg/m³)
Activated Solutions: Alkaline solutions of glutaraldehyde (pH 7.5-8.5) are used for medical device sterilization but have limited stability (14-28 days). They react with alcohols, ketones, amines, and proteins.
Respiratory Sensitization: Occupational exposure to glutaraldehyde vapors is a recognized cause of occupational asthma. Use appropriate respiratory protection and ventilation.
Polymerization: Glutaraldehyde polymerizes at alkaline pH via aldol condensation. Store at acidic pH (3-5) for maximum stability.
Fixation Mechanism: As a homobifunctional crosslinker, glutaraldehyde crosslinks proteins through Schiff base formation with lysine residues. This property makes it irreplaceable for electron microscopy fixation.
Compatibility: Glutaraldehyde is incompatible with strong oxidizers and strong bases. Activated (alkaline) solutions react with alcohols and amines.
Deactivation: Before disposal, deactivate glutaraldehyde solutions with sodium bisulfite or sodium metabisulfite (1:1 molar ratio).