Glutaraldehyde

Description

Glutaraldehyde is a dialdehyde and a reduced form of the corresponding diacid, glutaric acid. It was mentioned (as “trimethylene aldehyde”) in the chemical literature as early as 1908, when Russian chemists N. J. Demjanow* and K. Fortunatow synthesized it via the chromic oxide oxidation of 1,5-pentanediol (“trimethylene carbinol”).
Other ways to prepare glutaraldehyde include acidification of 2-methoxy- or 2-ethoxy-3,4-dihydro-2H-pyran and tungstic acid–catalyzed hydrogen peroxide oxidation of cyclopentene.
Because of its highly reactive aldehyde groups, glutaraldehyde is too unstable to store in its pure form. The article of commerce is usually a 25% or 50% aqueous solution; but it is also sold in methanol solution. As the hazard information table shows, it is toxic and must be handled carefully.
Glutaraldehyde’s many uses include sterilizing medical equipment, tanning leather, cross-linking polymers, and acting as a fixative in biochemical procedures. It?has even been tried as an ingredient in hair treatments, such as “permanent” waves.
Additional information about glutaraldehyde applications can be found on the ScienceDirect information page.

Description

Glutaraldehyde is a well-known sensitizer among cleaners and health workers. It is also found in X-ray developers products.

Chemical properties

Glutaraldehyde is a colorless liquid with a pungent odor, which readily changes to a glossy polymer. The Odor Threshold is 0.04 ppm (NY) and 0.2 ppm (NJ). It is miscible in water and organic solvents. Glutaraldehyde may be incompatible with strong oxidizers and strong bases. It should be noted that alkaline solutions containing glutaraldehyde may react with alcohol, ketones, amines, hydrazines, and proteins.

The Uses of Glutaraldehyde

Glutaraldehyde is used as a cold sterilizingdisinfectant, as fixatives for tissues, in tanning,and in cross-linking proteins.

The Uses of Glutaraldehyde

glutaral (glutardialdehyde) is a broad-spectrum preservative that can cause skin irritation. This is an amino acid occurring in green sugar beets.

The Uses of Glutaraldehyde

Glutaraldehyde (Symbol GTA; glutaric dialdehyde, 1,5-pentanedial, glutaral) is commonly used in the medical industry in cold sterilization and in the X-ray development process. It can also be encountered in the leather industry as a tanning ingredient and in mortuary workers. There are no reports which indicate that glutaraldehyde is a naturally occurring compound. Cidex and Acusol, 2% buffered solutions, use this aldehyde as an active ingredient. Sodium bicarbonate is required to activate the solution, which then has a shelf life of 1–2 weeks. Despite health hazards involved with its use, glutaraldehyde is one of the most effective biocides used. It is particularly effective against bacteria and viruses, including the human immunodeficiency virus.

The Uses of Glutaraldehyde

Glutaraldehyde is used to disinfect medical and dental equipment. Glutaraldehyde is also used for industrial water treatment and as a preservative.

Definition

ChEBI: A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.

What are the applications of Application

Glutaraldehyde solution, 50% w/w is an amine-reactive homobifunctional crosslinker

What are the applications of Application

Glutaraldehyde solution, 70% w/w is A homobifunctional crosslinker suitable as a fixative for electron microscopy

What are the applications of Application

Glutaraldehyde solution, 25% w/w is a protein cross-linking agent

Synthesis Reference(s)

Tetrahedron, 48, p. 3503, 1992 DOI: 10.1016/S0040-4020(01)88489-1

General Description

Light yellow liquid. Mixes with water.

Air & Water Reactions

Polymerizes in the presence of water.

Reactivity Profile

GLUTARALDEHYDE may discolor on exposure to air. Pentanedial polymerizes on heating. Pentanedial is incompatible with strong oxidizing agents. Pentanedial polymerizes in the presence of water.

Health Hazard

Glutaraldehyde is a strong irritant to the nose,eyes, and skin. In rabbits, 250 μg and 500 mg in 24 hours produced severe irritation in theeyes and skin, respectively. The corrosiveeffect on human skin of 6 mg over 3 dayswas severe. However, the acute toxicity ofglutaraldehyde by the oral and dermal routesis low to mild. Ohsumi and Kuroki (1988)determined that the symptoms of acute toxicityof this compound were less severethan those of formaldehyde. But the restraintof growth was more pronounced in micetreated with glutaraldehyde. An oral LD50value of 1300 mg/kg was reported for mice.Inhalation of this compound can cause upperrespiratory tract irritation, headache, and nervousness.Mice exposed at 33 ppm showedsymptoms of hepatitis.

Fire Hazard

Literature sources indicate that Pentanedial is nonflammable.

Flammability and Explosibility

Non flammable

Biochem/physiol Actions

Glutaraldehyde is an effective protein crosslinker and finds application in techniques like enzyme immobilisation microscopy, histochemistry and cytochemistry. It exists in different forms under acidic or neutral conditions. It is a biocide widely used as a disinfectant in hospitals and industries and is toxic to aquatic organisms. Its allergic nature leads to hypersensitivity reactions. Contact of glutaraldehyde vapors in endoscopy contributes to Colitis.

Contact allergens

Glutaraldehyde is a well-know sensitizer in cleaners and health workers. It can also be found in X-ray developers or in cosmetics.

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by inhalation, skin contact, and subcutaneous routes. Experimental teratogenic and reproductive effects. A severe eye and human skin irritant. Mutation data reported. When heated to decomp osition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Potential Exposure

Glutaraldehyde is used in leather tanning; in embalming fluids; as a germicide; as a cross-linking agent for protein and polyhydroxy materi als; as a fixative for tissues; and as an intermediate. Buffered solutions are used as antimicrobial agents in hospitals.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Likely impurities are oxidation products-acids, semialdehydes and polymers. It can be purified by repeated washing with activated charcoal (Norit) followed by vacuum filtration, using 15-20g charcoal/100mL of glutaraldehyde solution. Distil it at 60-65o/15mm, discarding the first 5-10%, then dilute with an equal volume of freshly distilled water at 70-75o, using magnetic stirring under nitrogen. The solution is stored at low temperature (3-4o), in a tightly stoppered container, and protected from light. Standardise by titration with hydroxylamine. [Anderson J Histochem Cytochem 15 652 1967, Beilstein 1 IV 3659.]

Incompatibilities

Water contact forms a polymer solution. A strong reducing agent. Incompatible with strong acids; caustics, ammonia, amines, and strong oxidizers. Note: Alkaline solutions of glutaraldehyde (i.e., activated glutar aldehyde) react with alcohol, ketones, amines, hydrazines, and proteins.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinera tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.