The structural formula of glutaraldehyde is shown below. When dissolved in water, the active molecular forms which contain carboxyl
groups react with amino groups in proteins and polyhydroxy compounds common in
most microorganisms rendering control in water systems.
Chemically, the cell walls of bacteria contain a unique
protein which, specifically, is a combination often different amino acids. The
amino groups are typical organic bases and effective nucleophilic compounds.
Glutaraldehyde reacts with the proteins of the bacterial cell
wall and the proteins within the internal portions of the cell via a
nucleophilic substitution reaction. The reaction will be internal or external
depending upon the pH of the water.
Under alkaline water conditions,
glutaraldehyde reacts with the free (unprotonated) amino groups on the outside
of the cell wall. In doing so, glutaraldehyde cross-links and binds the amino
groups on the cell wall preventing the cell from functioning by inhibiting
nutrients from entering the cell and waste products from leaving the cell.
Under acidic conditions, the amino groups on the outside of the cell wall are positively charged
(or protonated). In this case, glutaraldehyde penetrates the cell, and once
inside, functions in the same manner as it does at high alkalinity,
cross-linking the free amino groups of the proteins.
Since all microbial enzymes utilized for energy production
are proteins or combinations of proteins, their structure becomes altered
through cross-linking, thus rendering them nonspecific and unreactive. In this
manner, glutaraldehyde functions as an enzyme poison, extremely reactive and
broad spectrum in scope.
Glutaraldehyde shows particular strength in controlling
sulfate-reducing bacteria. Published literature specifically points out the
combination of glutaraldehyde and isothiazolone as being very effective in the
control of this troublesome bacteria. Glutaraldehyde is also unaffected by oil
contamination, making it a popular toxicant in refinery and oil production
applications.
In reviewing the mode of microbiocidal action of
glutaraldehyde, it is evident that it shows efficacy over a wide pH range. The
ability of this material to work more rapidly at high pH makes it a popular
choice in alkaline industrial water systems.
One area where this material shows reduced activity is in
systems with high ammonia contamination. Since the toxic nature to
microorganisms is derived from its reaction with proteins that are amine based,
ammonia contamination ties up the active molecular form of
glutaraldehyde, making it unavailable for biofouling control.