Amines, C16-18 and C18-unsatd. alkyl, ethoxylated

Endpoint summary

Additional information

Primary fatty amine ethoxylates 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 three different soils soil/water distribution coefficients (Kd values) were observed ranging from: 2025 to 4639 L/kg. Biodegradation is considered to be the main removal mechanism of these substances as they are readily biodegradable. Some ready biodegradability tests may however been hampered by the biocidal activity of these substances.

The half-life in the different environmental compartments will influenced by the bioavailability of the substances. No data is available for the determination of the primary fatty amine ethoxylates in soil or sediment. In absence of half-life data in these compartments these can as a worst-case be estimated based on the readily biodegradability and the sorption data as determined in a sorption desorption test.

As an alternative also read-across from a similar substance may be applied. For 14C hexadecylamine a half-life in three soils was measured according to an OECD 307 test. Although this C16 amine is strongly sorbing to soil (median Kp soil of 3875 L/kg at lowest measured concentration), half-life’s of 8.14 to 8.98 days were observed at 20 °C. These values can be recalculated (EUSES) to 12 °C a maximum half-life in soil of 16.9 days. As both primary alkyl amines and primary alkyl amine ethoxylates (2EO) are readily biodegradable and structurally strongly related, it is considered acceptable to use a half-life of 17 days in soil and sediment for the primary fatty amine ethoxylates risk assessment as well.

The Table below summarizes half-lives derived through default values and a simulation study.

Table Summary of degradation rate constants in various (eco) systems based the ready biodegradability of primary fatty amine ethoxylates.

(Eco) system	Method	Half-life
Surface water (fresh)	TGD default value	15 days half-life
Surface water (fresh) sediment	Measured; read-across	17 days half-life (aerobic)
Marine water	TGD default value	50 days half-life
Marine water sediment	Read-across	57 days half-life
Soils	Measured; read-across	17 days half-life^a
Degradation in sewage treatment plants	Determined in simulation test (OECD 303A)	>99.999% total removal of parent  99.83% removal by biodegradation 0.16% removal via sorption

^aHalf-life of the fraction dissolved in the water phase is expected to in the order of a few days.

Primary fatty amine ethoxylates have a short predicted half-life in air but because there are no important releases into the atmosphere and volatilization is expected to be negligible, this removal mechanism is thought to be of low relevance.

Primary fatty amine ethoxylates 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 primary fatty amine ethoxylates through hydrolysis is therefore not considered.

Direct photolysis of primary fatty amine ethoxylates 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.

No measured BCF fish is available for the primary fatty amine ethoxylates.

Standard OECD 305 tests are technically not feasible with these strongly sorbing easily 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 biodegraded. The bioaccumulation potential of primary fatty amine ethoxylates was therefore assessed based on a measured log Kow. As indicated before, primary fatty amine ethoxylates are readily biodegradable and it is therefore unlikely that they will accumulate in the food chain. Since there is a measured log Kow value available this value is used to assess the bioaccumulation potential.

Three valid measured log Kow values are however available as presented in the table below.

Primary fatty amines ethoxylates	CAS number	Measured log Kow
2,2'-(C12-18 evennumbered alkyl imino) diethanol	71786-60-2	0.7
2,2'-(C16-18 (evennumbered) alkyl imino) diethanol	1218787-30-4	3.6
2,2’(octadec-9-enylimino) -bisethanol	25307-17-9	3.4

 

The highest log Kow is observed for 2,2'-(C16-18 (evennumbered) alkyl imino) diethanol (CAS no 1218787-30-4). For this product also the lowest CMC of 3.5 mg/L was observed. The measured log Kow value of 3.6 indicates a moderate bioaccumulation potential for narcotic substances. For polar narcotics like the primary fatty amine ethoxylates however there is only limited information on the relationship between log Kow and BCF.

The in vitro biotransformation of C₁₂to C₁₈alkyldiethanolamines was therefore tested according to a slightly adapted Cellzdirect/Invitrogen Hepatic Rainbow Trout S9 Incubation Protocol using testosterone as benchmark.

The results show that C₁₂– C₁₈ alkyldiethanol amines are quickly metabolized.

A summary of the mean observed biotransformation rates, the predicted whole body metabolism rate (K_met) and BioConcentration Factor (BCF) are presented in the Table below. The K_met and BCF values were estimated using a calculation spreadsheet obtained from John Nichols (USEPA, personal communication). The BCF is calculated assuming that the reduction in bioavailability in the test is functionally identical to the reduction in bioavailability in fish plasma (f_u= 1).

 

Table: Summary of data in relation to the bioaccumulation potential of alkyl diethanolamines.

Alkyl chain length	Measured Log Kow using OECD 123*	Slope of log transformed substrate depletion curve**	Estimated Partitioning based BCF(L/kg)	Estimated Kmet(1/day)	Estimated BCF with biotransformation (L/kg)
C12	1.58	-0.119 ± 0.034	1.9	12.4	1.7
C14	2.79	-0.103 ± 0.017	31	4.05	25
C16	4.4	-0.051 ± 0.012	1256	0.82	465
C18	3.8	-0.011 ± 0.005	315	0.30	272

*Paulson, 2010a, b and c      

** Negative values represent the decrease of the test substance

 

The observed rapid biotransformation of the C₁₂ to C₁₈ alkyldiethanol amines demonstrates that it will be very unlikely that these substances will accumulate in fish. This was confirmed by the calculated BCF values which where all below the CLP threshold value of 500 L/kg. It is therefore concluded that C₁₂ to C₁₈ alkyldiethanolamines have a low bioaccumulation potential and that an in vivo evaluation of the bioaccumulation potential by e.g. performing an OECD 305 bioaccumulation test is not expected to result in BCF values > 500 L/kg.

The weight evidence of each of the fate points (log Kow, metabolism, biodegradability, bioavailability, BCF model) of a substance separately is limited but when considered together it is justified to concluded that primary alkyl amine ethoxylates (2EO) will not accumulate in the food chain and have a low bioaccumulation potential.