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EC number: 629-765-4
CAS number: 1226892-44-9
polyethylene amine imidazolines are for the main fraction protonated
under ambient conditions. This means that they will sorb strongly to
negatively charged surfaces like glassware, soil and sediment
constituents. For both DETA and PEPA based Imidazoline, Kd values were
observed ranging from: 19022 to 165846 L/kg for three different types of
combination with biodegradation is considered to be the main removal
mechanism of these substances. The hydrolysis test results of
the TEPA based imidazoline (CAS no1226892-45-0) showed
that the half-life of the first hydrolysis step (hydrolysis of the first imidazoline)
was 371, 16.3 and 19.5
hours at 20¿
at respectively pH 4, 7 and 9. The half-lifes for the second step (hydrolysis
of the amide) was 3744, 158 and 141 hours at 20 °C at respectively pH
4, 7 and 9. The half-lifes for the third step (hydrolysis of the second imidazoline)
was 1896, 672 and 1.8 * 10^5 hours at 20 °C at respectively pH 4, 7 and
9. Under environmental conditions the detachtment of the alkylchain and hydrolysis
of the imidazoline is considered to reduce the activity of the parent substance.
A half-life of 672 hours is therefore considered to be representative for
the hydrolysis of TEPA based imidazoline. A similar half-life in water is
considered to be applicable for the hydrolysis of the other imidazolines in
indicates that imidazolines are quickly hydrolyzed to the amidoamine
which is then biodegraded. The DETA
based amidoamine/imidazolines is completely metabolized to CO2, H2O and
NO3, for the amidoamine/imidazolines based on longer ethyleneamines no
degradation of the polyethyleneamines has been observed so these are
degraded to CO2, H2O and the polyethyleneamine which is used as starting
material in the production.
The half-life based
on biodegradation in the different environmental compartments may be
influenced by the bioavailability of the substances. But hydrolysis will not
be limited by the bioavailability of the substance. The half-life of the
parent substance will be short due to the fast hydrolysis in dependent of
the compartment as long as water is available. The half-life of the
product of the hydrolysis reaction i.e
the amidoamine, can probably best be evaluated based on its
biodegradation half-life. Based on the biodegradation curves obtained
for the DETA and PEPA based imidazoline, half-life’s of <30 days (at 20°C)
are observed if the remaining polyethylene amine is excluded from the
equiation. Therefore the half-life of 672 hours (or 28 days) is used
for risk assessment purposes. For read-across the other compartments than
water a safety factor of 2 is applied for precautionary reasons.
The Table below
summarizes half-lives derived through default values and a simulation
of degradation rate constants in various (eco) systems based the
inherent biodegradability of alkyl amidoamines/imidazolines.
Surface water (fresh)
Based on hydrolysis data
Surface water (fresh) sediment
Based on hydrolysis data and an assessment factor of 2
Based on hydrolysis data
amidoamines/imidazolines 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.
amidoamines/imidazolines contain hydrolysable covalent bonds and the
rate of hydrolysis was measured for a TEPA based imidazoline. Cleavage
of a carbon-nitrogen bond under environmental conditions is only
possible with a carbonyl group adjacent to the nitrogen atom.
photolysis of Alkyl amidoamines/imidazolines in air/water/soil will most
likely not occur, because it does not absorb UV radiation above 290 nm.
Photo transformation in air/water/soil is therefore assumed to be
negligible. Daylight might however influence the rate of hydrolysis.
Standard OECD 305
tests are technically not feasible with these strongly sorbing
degradable substances. In addition is the route of exposure in a
standard OECD 305 test unrealistic for these substances because the
substance will either be sorbed or degraded. The bioaccumulation
potential of amidoamines/imidazolines was therefore assessed based on a
measured log Kow. As indicated before, imidazolines are hydrolyzed and
consequently biodegraded and it is therefore unlikely that they will
accumulate in the food chain. The log Kow value as observed for the DETA
based imidazoline can be considered as a worst-case as lower log Kow
values are calculated for substances with a higher number of amines in
the structure. Based on this log Kow value of 2.2, the calculated log
BCF is 1.24 (BCF = 17.4; EpiSuite v4.0).
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