Tall oil, reaction products with diethylenetriamine

Biodegradation in water and sediment: simulation tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: sewage treatment simulation testing

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

key study

Justification for type of information:

It is considered appropriate to address the biodegradation in water and sediment simulation tests data requirement for DTO_DETA by read-across to an available study on Tall oil, reaction products with N-(2-aminoethyl)piperazine.
Tall oil, reaction products with N-(2-aminoethyl)piperazine is structurally related and of similar composition to AAI_DETA, a main component of DTO_DETA, with the only difference being the amine to which the fatty acid components are reacted with. Tall oil, reaction products with N-(2-aminoethyl)piperazine contains a mixture of components, including monoamide, diamide and imidazoline (mono-, di and tri-condensate) structures. The substance therefore has common functional groups based on the amine, amide and imidazoline moieties, and is therefore considered structurally related to AAI_DETA.
A key simulation study is available for Tall oil, reaction products with N-(2-aminoethyl)piperazine, and given the comparable biodegradation pathways of fatty amine derivatives i.e. oxidation of the alkyl chain (primary degradation) and bioavailability, it is considered appropriate to read across from this study to DTO_DETA. Rosins (the other main DTO_DETA component) are readily biodegradable and thus simulation data are not necessary.

Reason / purpose for cross-reference:

read-across source

% Degr.:

89

St. dev.:

1

Parameter:

DOC removal

Remarks on result:

other: mean removal percentage from day 34 to 48 (15 measurements)

% Degr.:

> 99.999

Parameter:

other: test mat analysis/using octadecenyl amide of N-(2-aminoethyl)piperazine as representative component

Remarks on result:

other: analysed in effluent of test unit from day 44 to 48

Transformation products:

no

NPOC concentrations in the effluent of the control and test unit and the calculated removal percentages of tall oil, reaction products with N-(2 -aminoethyl)piperazine.The data in grey part of the table are used to calculate the biodegradation percentage.

Time (days)	NPOC (mg/L)		Removal (%)
	Control	Test
-4	13.7	11.3
-2	12.1	11.6
2	9.5	9.0	101
0	10.8	17.9	81
6	11.0	17.2	83
9	11.7	19.5	79
13	12.7	17.6	87
16	13.9	18.5	87
20	12.7	17.4	87
23	8.3	15.4	81
27	9.7	17.2	80
30	7.5	14.9	80
34	9.1	14.6	85
35	12.0	15.3	91
36	10.3	16.0	84
37	12.7	14.9	94
38	10.2	16.4	83
39	10.9	14.4	90
40	11.0	15.1	89
41	10.5	14.9	88
42	11.4	15.0	90
43	13.0	17.1	89
44	12.1	17.6	85
45	13.9	17.1	91
46	12.8	17.2	88
47	12.6	16.7	89
48	13.7	18.4	87

Concentrations of tall oil, reaction products with N-(2 -aminoethyl)piperazine measured in the effluent and mixed liquid suspended solids (adsorption onto sludge) and removal percentages from the influent and by adsorption onto sludge, respectively.

Time (days)	Concentration (μg/L)	Removal (%)
	Effluent
44	<0.014	>99.999
45	<0.014	>99.999
46	<0.014	>99.999
47	<0.014	>99.999
48	<0.014	>99.999
Time (days)	Concentration (mg/L)	Removal (%)
	Mixed liquid suspended solids
47	0.88	0.044
48	0.80	0.040

Validity criteria fulfilled:

yes

Remarks:

COD removal in the control unit at Day 14 and day 48 of 90 and 92% resp. The ammonium and nitrite concentrations in the control effluent at Day 14 were <2.5 and <2.0 mg/L. These results demonstrate that the test is valid

Conclusions:

The CAS test demonstrates that tall oil, reaction products with N-(2-aminoethyl)piperazine biodegrade almost completely in properly operating conventional biological wastewater treatment plants. Tall oil, reaction products with N-(2-aminoethyl)piperazine is primarily removed by biodegradation 89±1% NPOC removal, determined in effluent samles from test unit during 15 days from day 34 to 48 (These organic carbon removal percentages in excess of the pass level of 80% indicate that the test substance is completely removed) >99.999% removal of test substance calculated with specific analysis in effluent samples taken from day 44-48 0.04-0.044 % removal of test substance by adsorption onto sludge, calculated with specific analysis in sludge samples taken on day 47 and 48.

Test performed under GLP according guidelines with a few accpetable (minor) deviations, meeting all validity criteria.

Executive summary:

It is considered appropriate to address the biodegradation in water and sediment simulation tests data requirement for DTO_DETA by read-across to an available study on Tall oil, reaction products with N-(2-aminoethyl)piperazine.

Tall oil, reaction products with N-(2-aminoethyl)piperazine is structurally related and of similar composition to AAI_DETA, a main component of DTO_DETA, with the only difference being the amine to which the fatty acid components are reacted with. Tall oil, reaction products with N-(2-aminoethyl)piperazine contains a mixture of components, including monoamide, diamide and imidazoline (mono-, di and tri-condensate) structures. The substance therefore has common functional groups based on the amine, amide and imidazoline moieties, and is therefore considered structurally related to AAI_DETA. A key simulation study is available for Tall oil, reaction products with N-(2-aminoethyl)piperazine, and given the comparable biodegradation pathways of fatty amine derivatives i.e. oxidation of the alkyl chain (primary degradation) and bioavailability, it is considered appropriate to read across from this study to DTO_DETA. Rosins (the other main DTO_DETA component) are readily biodegradable and thus simulation data are not necessary.

The continuous activated sludge (CAS) test was performed according to ISO Guidelines, and in compliance with the OECD principles of Good Laboratory Practice. Tall oil, reaction products with N-(2-aminoethyl)piperazine were exposed to micro-organisms maintained by addition of domestic wastewater in the CAS test. Tall oil, reaction products with N-(2-aminoethyl)piperazine were spiked at a nominal influent concentration of 50 mg/L (36.5 mg/L carbon; calculated) for a period of 48 days and included a control fed with domestic wastewater only. The immediate high removal percentages can be attributed to adsorption and probably biodegradation. The mean removal percentage of tall oil, reaction products with N-(2-aminoethyl)piperazine calculated over 15 measurements obtained from day 34 to 48 of the test was 89 +/-1% (95% confidence interval). These organic carbon removal percentages in excess of the pass level of 80% indicate that the test substance is completely removed. An accurate assessment of the removal of tall oil, reaction products with N-(2- aminoethyl)piperazine was established with specific analyses. The method (LCMS/ MS) for the determination of tall oil, reaction products with N-(2- aminoethyl)piperazine was satisfactory with regard to the linearity, repeatability of the injections, limit of quantification (LOQ), recovery and specificity. The mean removal percentage of tall oil, reaction products with N-(2-aminoethyl)piperazine in the test unit was assessed with the specific analysis from day 44 to 48 was >99.999% using octadecenyl amide of N-(2-aminoethyl)piperazine as representative component. These analyses demonstrate that the removal of tall oil, reaction products with N-(2-aminoethyl)piperazine is complete. Tall oil, reaction products with N-(2-aminoethyl)piperazine concentrations in the sludge of the reactor sampled on days 47 and 48 were 0.88 and 0.80 mg/L. The mean removal percentage of tall oil, reaction products with N-(2-aminoethyl)piperazine from the influent through adsorption onto sludge assessed in two samples was therefore 0.04 -0.044%. This percentage demonstrates that tall oil, reaction products with N-(2-aminoethyl)piperazine are almost completely removed by biodegradation. The CAS test demonstrates that tall oil, reaction products with N- (2-aminoethyl)piperazine almost completely removed from the wastewater by biodegradation in conventional biological wastewater treatment plants.

Description of key information

Imidazoline DETA

Chemically related fatty amine derivatives as for instance oleyl bis(2 -hydroxyethyl)amine (AkzoNobel 2010a), and tall oil, reaction products with N-(2 -aminoethyl)piperazine (AkzoNobel 2010b) have been assessed in CAS tests. Comparable biodegradation pathways of fatty amine derivatives i.e. oxidation of the alkyl hain (primary degradation) and the bioavailability are the keys to justification of the use of read-across of the results obtained CAS unit fed with domestic wastewater.

Rosins

For Rosins simulation data are not necessary as they are readily biodegradable.

Additional information

Imidazoline DETA

The Kpsed was determined as 47000 L/kg. The suggested maximum half-life for a readily degradable substance with a Kpsed in the range >10000 L/kg is 30000 days (at 12 ºC). These values are considered as extremely conservative but in the absence of measured data will be used in the exposure assessment as a worst-case. The half-life of the bioavailable fraction of tall oil diethylenetriamine imidazolinein the water phase of sediments is expected to be in the order of a few days, which is based on experiments with dialkyldimethylammonium salts (van Ginkel et al, 2003).

 

Biological wastewater treatment

Tall oil diethylenetriamine imidazoline has not been tested in the continuously-fed activated sludge (CAS) test. However, the fate of the chemically strongly related fatty amine derivative tall oil, reaction products with N-(2-aminoethyl)piperazine (AkzoNobel 2010a) has been assessed in a CAS test. Comparable biodegradation pathways of fatty amine derivatives i.e. oxidation of the alkyl chain (primary degradation) and the bioavailability are the keys to justification of the use of read-across of the results obtained CAS unit fed with domestic wastewater. Removal percentages of the parent compounds from the influent and removal by biodegradation in the CAS units are given below.

Surfactant	Removal from wastewater (%)	Removal by biodegradation (%)
Tall oil, reaction products with N-(2-aminoethyl)piperazine(CAS no92062-17-4)	>99.999	99.96

The removal of tall oil diethylenetriamine imidazoline from wastewater in biological wastewater systems through read-across is assumed to be >99.999%. The removal by biodegradation in biological wastewater treatment is expected to be >99.8

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