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Glutaraldehyde

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Glutaraldehyde

Glutaraldehyde
Skeletal formula of glutaraldehyde
Ball-and-stick model of the glutaraldehyde molecule
Names
IUPAC name
Pentane-1,5-dial
Other names
Pentanedial, Glutardialdehyde, Glutaric acid dialdehyde, Glutaric aldehyde, Glutaric dialdehyde, 1,5-Pentanedial
Identifiers
 Y
ChemSpider  Y
DrugBank  Y
Jmol-3D images Image
KEGG  Y
PubChem
UNII  Y
Properties
C5H8O2
Molar mass 100.117
Appearance Clear liquid
Odor pungent[1]
Density 1.06 g/mL
Melting point −14 °C (7 °F; 259 K)
Boiling point 187 °C (369 °F; 460 K)
Miscible, reacts
Vapor pressure 17 mmHg (20°C)[1]
Hazards
Flash point noncombustible[1]
US health exposure limits (NIOSH):
PEL (Permissible)
none[1]
REL (Recommended)
C 0.2 ppm (0.8 mg/m3)[1]
N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Glutaraldehyde is an industrial water treatment and as a preservative. It is mainly available as an aqueous solution, and in these solutions the aldehyde groups are hydrated.[2]

Contents

  • Production and structure 1
  • Uses 2
    • Sterilisation 2.1
    • Fixative 2.2
    • Wart treatment 2.3
    • Hydraulic fracturing (fracking) fluid 2.4
    • Aquariums with plants 2.5
  • Safety 3
  • References 4
  • External links 5

Production and structure

Glutaraldehyde is produced industrially by the oxidation of cyclopentene and by the Diels-Alder reaction of acrolein and methyl vinyl ether followed by hydrolysis.[2]

Like other dialdehydes (e.g., glyoxal), it does not exist as the dialdehyde but as the hydrate. These hydrates adopt several equilibrating species.[3]

Monomeric glutaraldehyde can polymerize by aldol condensation reaction yielding alpha, beta-unsaturated poly-glutaraldehyde. This reaction usually occurs at alkaline pH values.

Uses

Sterilisation

A glutaraldehyde solution of 0.1% to 1.0% concentration may be used for system disinfection and as a preservative for long term storage. It is a sterilant, killing

  • National Pollutant Inventory - Glutaraldehyde Fact Sheet
  • National Institute for Occupational Safety and Health - Glutaraldehyde
  • NIST WebBook
  • Glutaraldehyde at OpenWetWare (the life science wiki)

External links

  1. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0301".  
  2. ^ a b Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber (2005), "Aldehydes, Aliphatic",  
  3. ^ Whipple Earl B., Ruta Michael (1974). "Structure of Aqueous Glutaraldehyde". J. Org. Chem 39: 1666–1668.  
  4. ^ HCC lecture notes, 15: Control of microrganisms
  5. ^ Karnovsky, M.J. (1965). A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. Journal of Cell Biology 27: 137A–138A
  6. ^ Boostrix prescribing information, ©2009, GlaxoSmithKline
  7. ^ NHS Choices: Glutarol
  8. ^ Morgantown Utility Board. "Fracking Fluid Additives - Fracking Fluid MSDS's". . Links to documents, including Alpha 1427 Material Safety Data Sheet
  9. ^ "Material Safety Data Sheet, Flourish Excel" (PDF). Archived from the original (PDF) on 13 May 2013. Retrieved 25 August 2014. 
  10. ^ Canadian Centre for Occupational Health and Safety (CCOHS) (a federal government site) > OSH Answers > Diseases, Disorders & Injuries > Asthma Document last updated on February 8, 2005
  11. ^ Toxicology and Carcinogenesis Studies of Glutaraldehyde

References

As a strong sterilant, glutaraldehyde is toxic and a strong irritant.[10] There is no evidence of carcinogenic activity.[11]

Safety

Glutaraldehyde is an ingredient in a product for freshwater aquariums as a source of bioavailable organic carbon used by aquatic plants.[9]

Aquariums with plants

Glutaraldehyde is a component of hydraulic fracturing "fracking" fluid. It is included in the additive called Alpha 1427, as a biocide.[8] Bacterial growth can impair the production of oil and gas wells, and can be introduced into the formation from various sources including the source water, proppant, and polymer used in the hydraulic fracturing process. Glutaraldehyde is pumped as a liquid additive with the fracturing fluid to reduce or eliminate this source of formation and fracture conductivity damage.

Hydraulic fracturing (fracking) fluid

A solution of glutaraldehyde, typically of 10% w/w, is sold under various trade names to remove common and plantar warts. It is said to inactivate viruses and bacteria, and to dry the skin, facilitating physical removal of the wart.[7] Trade names include Diswart Solution and Glutarol.

Wart treatment

In a related application, glutaraldehyde is sometimes employed in the tanning of leather.

Another application for treatment of proteins with glutaraldehyde is the inactivation of bacterial toxins to create toxoid vaccines, e.g., the pertussis (whooping cough) toxoid component in the Boostrix Tdap vaccine produced by GlaxoSmithKline.[6]

Glutaraldehyde is used in biochemistry applications as an amine-reactive homobifunctional membrane lipids. Fixation is usually followed by dehydration of the tissue in ethanol or acetone, followed by embedding in an epoxy resin or acrylic resin.

Fixative

[4]

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