Tall oil, reaction products with diethylenetriamine

Biodegradation in water: screening tests

Link to relevant study record(s)

Reference

Endpoint:

biodegradation in water: ready biodegradability

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 data requirements for DTO_DETA by read-across to the available studies on the main components of DTO-DETA: AAI_DETA and Rosin.
DTO_DETA and AAI_DETA are each a mixture of constituents which include monoamide, diamide, residual amine and imidazoline (mono-, di- and tri-condensate) chemical structures. The substances therefore have common functional groups based on amide, amine and imidazoline moieties and are sufficiently similar in terms of chemical structure to support a read-across approach.
DTO_DETA contains comparatively lower levels of imidazolines and higher levels of resin acids than AAI_DETA and therefore consideration of data for resin acids is also considered necessary. The main resin acid in DTO_DETA is abietic acid, but abietic acid derivatives and other acids, such as pimaric acid, are also found in notable quantities, and the resin acids collectively are known as ‘rosin’. DTO_DETA contains upto 25% unreacted rosin, and taking into account the compositional information available for the rosin in DTO_DETA and Rosin (CAS# 8050-09-07, EC# 232-475-7), the latter was considered appropriate for read-across to DTO_DETA. Ready biodegradabilty studies are available for both substances and it is considered appropriate to read across from these studies to DTO_DETA.

Reason / purpose for cross-reference:

read-across source

Reason / purpose for cross-reference:

read-across source

Reason / purpose for cross-reference:

read-across source

Key result

Parameter:

% degradation (O2 consumption)

Value:

24

Sampling time:

28 d

Remarks on result:

other: DETA imidazoline - 61% after 60 days

Parameter:

% degradation (O2 consumption)

Value:

71

Sampling time:

28

Remarks on result:

other: Rosins 1999a

Parameter:

% degradation (O2 consumption)

Value:

71

Sampling time:

28

Remarks on result:

other: Rosins 1999b

Tall oil diethylenetriamine imidazoline

Oxygen consumption (mg/L) and the percentages biodegradation of the test substance, Tall oil diethylenetriamine imidazoline (BOD/COD) and sodium acetate (BOD/ThOD) in the Closed Bottle test.

Time (days)	Oxygen consumption (mg/L)		Biodegradation (%)
	Test substance	Acetate	Test substance	Acetate
0	0.0	0.0	0	0
7	0.1	4.6	2	85
14	0.3	4.7	6	87
21	0.6		11
28	1.3		24
42	2.7		50
60	3.3		61

Rosins (Akzo Nobel 1999a)

Oxygen Consumption (mg/L) and Biodegradation of Na Salt of Gum Rosin (BOD/COD) and Sodium Acetate (BOD/ThOD) in the Closed Bottle Test

Time (days)	Oxygen Consumption (mg/L)		Biodegradation (%)
	Test	Acetate	Test	Acetate
0	0,0	0,0	0	0
1	0,8		15
2	1,6		31
3	1,7		33
4	1,8		35
5	2,0		38
7	2,6	3,2	50	59
10	3,3		63
12	3,5		67
14	3,5	3,7	67	69
17	3,7		71
19	3,7		71
21	3,7		71
24	3,8		73
28	3,7		71

Rosins (Akzo Nobel 1999b)

Oxygen Consumption (mg/L) and Biodegradation of Na Salt of Tall Oil Rosin (BOD/COD) and Sodium Acetate (BOD/ThOD) in the Closed Bottle Test

Time (days)	Oxygen Consumption (mg/L)		Biodegradation (%)
	Test	Acetate	Test	Acetate
0	0.0	0.0	0	0
1	0.7		13
2	1.5		28
3	1.6		30
4	1.9		36
5	2.1		40
7	2.6	3.2	49	59
10	3.2		60
12	3.4		64
14	3.4	3.7	64	69
17	3.6		68
19	3.6		68
21	3.6		68
24	3.8		72
28	3.7		71

Validity criteria fulfilled:

yes

Interpretation of results:

inherently biodegradable

Conclusions:

Tall oil diethylenetriamine imidazoline
Test performed under GLP according guidelines with (minor) acceptable deviations, meeting all validity criteria.
Tall oil diethylenetriamine imidazoline was biodegraded 24% at day 28 in the Closed Bottle test. This test substance should therefore not be classified as readily biodegradable. In the prolonged Closed Bottle test tall oil diethylenetriamine imidazoline was biodegraded 61% at day 60. The biodegradation reached at the day 60 of the test demonstrates that this test substance is not persistent.

Rosins (Akzo Nobel 1999a)
The test substance exhibited 15% degradation at day 1 and 63% degradation at day 10 thereby meeting the 60% degradation within a 10 day window criterion to be considered readily biodegradable. 71% degradation was observed at test termination on day 28.

Rosins (Akzo Nobel 1999b)
The test substance exhibited 13% degradation at day 1 and 60% degradation at day 10 thereby meeting the 60% degradation within a 10 day window criterion to be considered readily biodegradable. 71% degradation was observed at test termination on day 28.

Executive summary:

It is considered appropriate to address the data requirements for DTO_DETA by read-across to the available studies on the main components of DTO_DETA: AAI_DETA and Rosin. DTO_DETA and AAI_DETA are each a mixture of constituents which include monoamide, diamide, residual amine and imidazoline (mono-, di- and tri-condensate) chemical structures. The substances therefore have common functional groups based on amide, amine and imidazoline moieties and are sufficiently similar in terms of chemical structure to support a read-across approach. DTO_DETA contains comparatively lower levels of imidazolines and higher levels of resin acids than AAI_DETA and therefore consideration of data for resin acids is also considered necessary. The main resin acid in DTO_DETA is abietic acid, but abietic acid derivatives and other acids, such as pimaric acid, are also found in notable quantities, and the resin acids collectively are known as ‘rosin’. DTO_DETA contains upto 25% unreacted rosin, and taking into account the compositional information available for the rosin in DTO_DETA and Rosin (CAS# 8050-09-07, EC# 232-475-7), the latter was considered appropriate for read-across to DTO_DETA. Ready biodegradabilty studies are available for both substances and it is considered appropriate to read across from these studies to DTO_DETA.

Tall oil diethylenetriamine imidazoline

In order to assess the biotic degradation, a ready biodegradability test was performed which allows the biodegradability to be measured in an aerobic aqueous medium. The ready biodegradability was determined in the Closed Bottle test performed according to slightly modified OECD, EU and ISO Test Guidelines, and in compliance with the OECD principles of Good Laboratory Practice. The test was prolonged because the pass level was not reached at Day 28. Tall oil diethylenetriamine imidazoline in the presence of silica gel did not cause a reduction in the endogenous respiration. The test substance is therefore considered to be non-inhibitory to the inoculum. Tall oil diethylenetriamine imidazoline was biodegraded 24% at day 28 in the Closed Bottle test. This test substance should therefore not be classified as readily biodegradable. In the prolonged Closed Bottle test tall oil diethylenetriamine imidazoline was biodegraded 61% at day 60. The biodegradation reached at the day 60 of the test demonstrates that this test substance is not persistent. The test is valid as shown by an endogenous respiration of 1.4 mg/L and by the total mineralization of the reference compound, sodium acetate. Sodium acetate was degraded 87% of its theoretical oxygen demand after 14 days. Finally, the most important criterion was met by oxygen concentrations >0.5 mg/L in all bottles during the test period.

Rosins (Akzo Nobel 1999a)

In order to assess the biotic degradation, a ready biodegradability test was performed which allows the biodegradability to be measured in an aerobic aqueous medium, The ready biodegradability was determined in the Closed Bottle test performed according to slightly modified OECD, EEC and ISO Test Guidelines, and in compliance with the OECD principles of Good Laboratory Practice.

Rosin is a poorly soluble substance in water. Prior to the intitiation of this study the sample of gum rosin was converted to the sodium salt of gum rosin through adjustment of the pH to 11.3 using NaOH and stirring at 75C for one hour. The resultant sodium salt of gum rosin was biodegraded 71% at day 28 in the Closed Bottle test and meeting the 60% degradation within the 10 day window criterion. Hence this compound should be classified as readily biodegradable.

The test is valid as shown by an endogenous respiration of 1.6 mg/L at day 28 and by the total mineralization of the reference compound, sodium acetate. Sodium acetate was degraded 69% of its theoretical oxygen demand after 14 days. Finally, the most important criterion was met by oxygen concentrations >0.5 mg/L in all bottles during the test period.

Rosins (Akzo Nobel 1999b)

In order to assess the biotic degradation, a ready biodegradability test was performed which allows the biodegradability to be measured in an aerobic aqueous medium, The ready biodegradability was determined in the Closed Bottle test performed according to slightly modified OECD, EEC and ISO Test Guidelines, and in compliance with the OECD principles of Good Laboratory Practice.

Tall Oil Rosin is a poorly soluble substance in water. Prior to the intitiation of this study the sample of tall oil rosin was converted to the sodium salt of tall oil rosin through adjustment of the pH to 11.3 using NaOH and stirring at 75C for one hour. The resultant sodium salt of tall oil rosin was biodegraded 71% at day 28 in the Closed Bottle test and meeting the 60% degradation within the 10 day window criterion. Hence this compound should be classified as readily biodegradable. The test is valid as shown by an endogenous respiration of 1.6 mg/L at day 28 and by the total mineralization of the reference compound, sodium acetate. Sodium acetate was degraded 69% of its theoretical oxygen demand after 14 days. Finally, the most important criterion was met by oxygen concentrations >0.5 mg/L in all bottles during the test period.

Description of key information

Imidazoline DETA
Tall oil diethylenetriamine imidazoline is considered not persistent as >60% degradation is observed after 60 days in a prolonged ready test. The substance is therefore considered inherently biodegradable.

Rosins
Substances in the category Rosin, Hydrogenated rosin and their salts are considered readily biodegradable.
On the basis of the available data on the read across substances the substance is considered inherently biodegradable.

Key value for chemical safety assessment

Biodegradation in water:

inherently biodegradable

Type of water:

freshwater

Additional information

Imidazoline DETA

Tall oil diethylenetriamine imidazoline may be biocidal to micro-organisms and consequently inhibitory in all ready biodegradability tests. Reduction of the toxicity of fatty amine derivatives in ready biodegradability tests has therefore been achieved through the addition silica gel (van Ginkel et al, 2008). For toxic substances, the specified high test substance concentrations in ready biodegradability tests are controversial because substances are present in the environment in the sub μg/L range.Tall oil diethylenetriamine imidazoline tested in the presence of silica gel was biodegraded 24% at day 28 in the Closed Bottle test. In the prolonged Closed Bottle test tall oil diethylenetriamine imidazoline was biodegraded 61% at day 60 (Akzo Nobel, 2010). The bio­degradation reached at the day 60 demonstrates that tall oil diethylenetriamine imidazoline is ultimately biodegradable and not persistent. In another Closed Bottle test a biodegradation percentage of 17 was reached at day 28 (Arkema, 2009). Complete (ultimate) degradation of tall oil diethylenetriamine imidazoline was also found in a semi continuously fed activated sludge (SCAS) test (van Ginkel et al, 2010). In this test removal percentages of organic carbon of >90% were achieved. Complete degradation of tall oil diethylenetriamine imidazoline can also be concluded from the ready biodegradability of fatty acids and diethylenetriamine formed upon hydrolysis (Popp, 1977; van Ginkel et al 1995). 

Rosins

All of the members of this category are UVCB substances that are ionizable and many exhibit low solubility. They are inherently difficult to test for many environmental parameters. A number of biodegradation studies have been performed on these substances with varying results. Highly variable results are believed to be due to solubility and bioavailability issues as well as ionization effects caused by slight differences in pH of the media utilized in the studies.

 

A number of reliable studies are available for members of this category that indicate that substances in the category are readily biodegradable, meeting the 10-day window. Studies are available for Resin acids and rosin acids, magnesium salts (Harlan Laboratories, 2010b) and Resin acids and rosin acids, calcium zinc salts (Harlan Laboratories, 2010a) that determine these substances to be readily biodegradable. In addition a study is available for Rosin (Akzo Nobel, 1999a). During sample preparation in this study the sample was mixed with NaOH and heated to 75°C, this would convert the test item to Resin acids and rosin acids, sodium salts, another category member. This study determined the test item to be readily biodegradable. A study is available for Tall oil rosin, considered equivalent to Rosin, (Akzo Nobel, 1999b). During sample preparation the test item in this study is also believed to convert to Tall oil rosin, sodium salts, considered equivalent to Resin acids and rosin acids, sodium salts. The test item was determined to be readily biodegradable.

 

A number of studies are available that indicate the substances are readily biodegradable, but not meeting the 10-day window. However, as these substances are complex UVCBs, the 10 day window criterion does not apply and these substances are also considered to be readily biodegradable. Studies with this result are available for Rosin (Wildlife International 1998) and Hydrogenated rosin, potassium salts (Harlan Laboratories, 2010e).

 

An enhanced biodegradation study is available for Rosin (Harlan Laboratories, 2010c). This study used modifications for a poorly soluble substance; these were larger test vessels and an increased amount of biomass. The substance was determined to be readily biodegradable under the conditions of the test. Due to the modifications to the study design this study is used as a supporting study only.

An inherent biodegradation study is available for Resin acids and rosin acids, potassium salts (Inveresk Research, 2002a,b). This indicates that the substance is inherently biodegradable.

 

A number of tests with Rosin (Notox (1988a), Laboratory for Applied Biology (1992), Harlan Labratories (2010d)), Hydrogenated rosin (Inveresk Research (2002a,b), Notox (1988b)), Rosin, reaction products with formaldehyde (Safepharm Laboratories, 1993) and Hydrogenated rosin potassium salts (Eastman 2004), determined that the test items did not meet the strict ready biodegradability criteria under the conditions of the test.

 

Due to the stringent test conditions in biodegradation studies, ECHA's Guidance on Information Requirements and Chemical Safety Assessments R7b: Endpoint specific guidance recommends that consistent positive results should supersede negative results. As a number of reliable studies are available for different members of this category indicating that the substances are readily biodegradable, members of the category Rosin, Hydrogenated rosin and their salts are considered readily biodegradable.