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EC number: 696-364-9
CAS number: 133779-11-0
fate data of various alkyl-1,3 -diaminopropanes has been used for the
evaluation of the environmental fate of this category. The justification
for the read-across is based on the similarities in their chemical
structure, physico-chemical and environmental fate properties. All
alkyl-1,3-diaminopropanes under consideration consist of carbon,
hydrogen and nitrogen only. The basic structure includes a hydrocarbon
chain with a 1,3-propanediamine group at the end of the chain. Due to
the identical position of the functional diamine group and the identical
CH2-groups adjacent to the diamine group, no difference in chemical
reactivity is expected for the functional group. The only difference
consists of differing chain lengths and slight variations in the degree
of saturation in the alkyl chain. Since the majority of the alkyl chains
consist of C12 to C18-units, and the unsaturated part is mainly located
in the more central part of the alkyl chain, significant changes in
chemical behavior and/or reactivity is not to be expected.
-diaminopropanes are protonated under ambient conditions. This means
that they will sorb strongly to negatively charged surfaces like
glassware, soil and sediment constituents. For four different soils
Kd-values were observed ranging from 250 to 850 L/kg for N-C16 -18-alkyl
(even-numbered) propane-1,3-diamine (CAS no. 133779-11-0).
Biodegradation is considered to be the main removal mechanism of this
substance. The half-life in the different environmental compartments is
expected to be short. No measured data is available which quantifies the
half-life of diamines in soil or sediment. These values can therefore be
estimated as a worst-case based on the readily biodegradability and the
sorption data as determined in the sorption desorption test.
For14C-labelled hexadecylamine, a substance structurally strongly
related to the alkyl-1,3 -diaminopropanes, a half-life in three soils
was measured according to an OECD 307 test. Half-lives of 8.1 to 9.0
days were observed at 20 °C or recalculated to 12 °C (EUSES) a maximum
half-life in soil of 17 days. For octadecylamine a similar sorption was
observed as for octadecyl-1,3-diaminopropane. As both primary alkyl
amines and alkyl-1,3 -diaminopropanes (diamines) are readily
biodegradable and have a comparable sorption to soil and sediment, it is
considered reasonable to use an half-life of 17 days in soil and
sediment for the N-C12-14 alkyl-1,3 -diaminopropane risk assessment as
observed removal in a waste water treatment simulation test was 99.4%
for N-C16-18-alkyl (even-numbered) propane-1,3-diamine (CAS no.
133779-11-0) using specific chemical analyses (LC-MS/MS) during day 56
to 60 (n=5). In addition the sorption to sludge was measured and this
accounted for 4.1% of the total removal which means that 95.3% was
removed by biodegradation.
degradation rates for the exposure assessment
Degradation in water
Degradation in seawater
Degradation in sediment
Degradation in soil
have a short predicted half-life in air but because there are no
important releases into the atmosphere and volatilisation is expected to
be negligible, this removal mechanism is thought to be of low relevance.
Diamines do not contain hydrolysable covalent bonds. Cleavage of a
carbon-nitrogen bond under environmental conditions is only possible
with a carbonyl group adjacent to the nitrogen atom. Degradation of
diamines through hydrolysis is therefore not considered.
photolysis of diamines in air/water/soil will not occur, because it does
not absorb UV radiation above 290 nm. Photo transformation in
air/water/soil is therefore assumed to be negligible.
OECD 305 tests to assess the bioaccumulation are technically not
feasible with these strongly sorbing easily degradable substances.
Several attempts have been made which demonstrated that maintaining a
steady state exposure at the low aquatic concentrations required is
impossible. Furthermore, the route of exposure in a standard OECD 305
test is unrealistic for these substances because the substance will
either be sorbed or biodegraded. The bioaccumulation potential of
diamines was therefore assessed based on a measured log Kow. These log
Kow values were measured using the slow stirring method according to
OECD 123. This test was performed for amines, N-9 -octa-decenyl-,
(Z)-propane-1,3 -diamine (7173 -62 -8), N-hydrogenated C16 -18
-alkyl-(evennumbered)propane-1,3 -diamine (68603 -64 -5) and N-Alkyl
(C12 -C14) -1,3 -diaminopropane (90640 -43 -0) and resulted in log Kow
values of respectively 0.0, 1.5 and -0.6 indicating a low
bioaccumulation potential. The calculated log BCF using EPIsuite (v4.0)
are respectively 0.66, 0.5 and 0.5.
for the primary alkyl amine and ethoxylated(2EO)alkyl amines
biotransformation has been observed for C12 and C14 alkyldiamines in an
in-vitro biotransformation test using hepatic S9 subcellular fraction
indicating that bioaccumulation of diamines in fish is very unlikely.
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