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EC number: 696-364-9
CAS number: 133779-11-0
Alkyl-1,3-diaminopropanes are in general poorly soluble in water and at
normal test concentrations toxic to the micro-organisms in the inoculum.
Silica gel may be added to reduce the exposure concentration and to
facilitate the slow release of the test substance. Under these
conditions, the substances are observed to be readily biodegradable in
closed bottle tests.
Diamines (alkyl-1,3-diaminopropanes) are well-known for their biocidal
properties and are expected to inhibit growth in ready biodegradability
tests carried out at “high” initial concentrations (van Ginkel, 1995).
Concentrations of 2 mg/L of the test substance are prescribed in the
closed bottle test, which is very low compared to the initial
concentrations used in other ready biodegradability tests. The closed
bottle test is therefore the superior ready biodegradability test for
alkyl-1,3-diaminopropanes. The result of many ready biodegradability
tests including the closed bottle test may not necessarily reflect the
true biodegradation potential of alkyl-1,3 -diaminopropanes due to the
toxicity. To minimize the biocidal effect, silica gel has been added to
closed bottle tests (see table below). Before the start of the test, the
test substance is sorbed onto silica. During the test period, the test
substance will slowly release from the silica and will be degraded. The
use of silica gel, allowed the demonstration of the ready
biodegradability of oleyl-1,3-diaminopropane, coco-1,3 -diaminopropane
and N-C16-18-alkyl-(evennumbered) C18 unsaturated-1,3-diaminopropane.
Most ready biodegradability test results with Diamines have been found
through investigations with Closed Bottle tests, (OECD 301D). The 10-day
time window has been ignored as a pass fail criterion as these
substances are UVCB's. Poor water solubility of Diamines and/or
adsorption of the substance onto solids do affect biodegradation
kinetics because of low desorption and dissolution rates of the test
substance. Dissolution and desorption rates in the tests do probably not
reflect these processes in the environment because concentrations used
in the tests are a few orders higher than the environmental
concentrations. The biodegradation curves of substances with a poor
water solubility and/or limited bioavailability due to adsorption
usually show a linear curve instead of the anticipated S-shaped curve
(logistic growth or growth with Monod).
Over the past decade, comprehensive knowledge has been gained on the
biodegradation mechanism of many fatty amine derivatives. All research
to date identifies a central cleavage of the fatty amine derivatives as
initial biodegradation step giving alkanals as intermediates (van
Ginkel, 1996; van Ginkel 2008). The central fission of the fatty amine
derivatives also results in the formation of hydrophilic degradation
products. Starting from an enrichment culture a bacterium capable of
degrading diamines with alkyl chains ranging from C10 to C18 was
isolated. Dodecylamine, dodecanoic acid, acetic acid and ß-alanine also
served as carbon and energy sources for the isolate. This bacterium was
not capable of utilizing 1,3-diaminopropane (Akzo Nobel unpublished
results). These results strongly indicate that bacteria capable of
degrading diamines catalyze a central fission resulting in the formation
of alkylamines and 3 -aminopropionaldehyde. 3-Aminopropionaldehyde is
further oxidized to ß-alanine. Alkylamines are converted into alkanals
(Yoshimura et al, 1980; van Ginkel et al, 2008). One microorganism is
therefore capable of degrading diamines with varying alkyl chain lengths.
Based on the broad substrate specificity of microorganisms
degrading diamines and fatty amine derivatives in general with respect
to the alkyl chain length it is unlikely that the biodegradability of
diamines differs significantly with varying alkyl chain lengths. Indeed,
the degradation observed in closed bottle tests with proper amounts of
silica gel were comparable for the diamines tested. The adequate ready
biodegradability test results in combination with scientific evidence
that a single micro-organism degrades all diamines lead to the
conclusion that all diamines are readily biodegradable. Typical members
of the family are given in the table below.
Table Typical members of the family of alkyl-1,3-diaminopropanes.
N-(C14-18and C16-18-unsaturated alkyl) propane-1,3 -diamine
N-(hydrogenated N-C16-18-alkyl-(evennumbered) propane-1,3 -diamine
Old CAS no: 68603-64-5
New CAS no: 133779 -11-0
N-C16-18-alkyl-(evennumbered) C18 unsaturatedpropane-1,3 -diamine
Old CAS no: 61791 -55 -7
New CAS no:1219010-04-4
Composition of N-C14 -18 and
N-C16-18-alkyl-(evennumbered) C18 unsaturated-alkyl chains are specified
by Karleskind (1996).
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