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Environmental fate & pathways

Adsorption / desorption

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Link to relevant study record(s)

Reference
Endpoint:
adsorption / desorption, other
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. It is considered appropriate to read across from information on these two substances to DTO_DETA.
Reason / purpose for cross-reference:
read-across source
Reason / purpose for cross-reference:
read-across: supporting information
Reason / purpose for cross-reference:
read-across: supporting information
Reason / purpose for cross-reference:
read-across: supporting information
Reason / purpose for cross-reference:
read-across: supporting information
Reason / purpose for cross-reference:
read-across: supporting information
Reason / purpose for cross-reference:
read-across: supporting information
Reason / purpose for cross-reference:
read-across: supporting information
Key result
Type:
Kd
Value:
47 000
Temp.:
20 °C
% Org. carbon:
2.16
Remarks on result:
other: Key read-across data from an experimental study on Tall oil diethylenetriamine imidazoline
Type:
Koc
Value:
> 28 164 - < 231 739
Remarks on result:
other: Supporting data based on calculation on Kow
Type:
Koc
Value:
5 357
Remarks on result:
other: Supporting data based on (Q)SAR estimation on Rosin
Type:
Koc
Value:
41.83
Remarks on result:
other: Supporting data based on (Q)SAR estimation on Resin acids and Rosin acids, sodium salts
Type:
Koc
Value:
41.83
Remarks on result:
other: Supporting data based on (Q)SAR estimation on Resin acids and Rosin acids, potassium salts
Type:
Koc
Value:
7.514
Remarks on result:
other: Supporting data based on (Q)SAR estimation on Resin acids and Rosin acids, magnesium salts
Type:
Koc
Value:
30.5
Remarks on result:
other: Supporting data based on (Q)SAR estimation on Resin acids and Rosin acids, zinc salts
Type:
Koc
Value:
135.4
Remarks on result:
other: Supporting data based on (Q)SAR estimation on Resin acids and Rosin acids, calcium salts
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. It is considered appropriate to read across from information on these two substances to DTO_DETA.

Imidazoline DETA

Due to the cationic surface-active properties of tall oil poly ethyleneamine based imidazolines, these substances will adsorb strongly onto the solid phase of soil and sediments. The substance can adsorb both onto the organic fraction and, dependent on the chemical composition, onto the surface of the mineral phase, where sodium and potassium ions can be exchanged against the alkyl ammonium ion. The determination of a Koc from log Kow is not opportune, because the common equations for Koc derivation are not valid for both ionic and surface active substances.

 

The adsorption behaviour DETA based tall oil poly ethyleneamine imidazolines was studied in batch equilibrium experiments according to a refined OECD 106 (Farnback, 2010). In both studies three soils were used, encompassing a range of clay and organic matter. The test substance adsorbed partially onto the container walls which was considered for the determination of the adsorption coefficients. Adsorption kinetics was determined by measurements at different sampling times (up to 24 h), equilibrium was reached after 24 hours but after 3 hours there was only a limited difference observed. Desorption occurred to a lesser extent than adsorption. The tables below present a summary of the most important soil properties and observed partitioning constants for both imidazolines.

Overview of sorption test results of Tall oil diethylenetriamine imidazoline (CAS No 68442-97-7)

 Soil  Clay (%)  Silt (%)  Sand (%)  CEC (meq/100g)  pH  OrgC (%)  Caq (ug/l)  Kd (104cm3/g)  Koc (106cm3/g)
 Speyer 2.2  6.4  12.2  81.4  10 5.4   2.16  4.2  4.7  2
 Eurosoil 4  20.3  75.7  4.1  17.3  6.8  1.31  10  1.9  1.4
 Speyer 6S  42.1  36  21.9 22   7.2  1.75  1.6 15   7.8

From the data it can be observed that the sorption onto Speyer 6S is much higher than to Speyer 2.2 despite of the higher organic matter content in the Speyer 2.2 soil. This can be explained that ionic interactions play a more important role than hydrophobic partitioning with organic matter. Alkyl ammonium ions can interact with the surface of mineral particles or with negative charges of humic substances. The influence of the chain length on the sorption behaviour is therefore expected to be less important only for the hydrophobic interaction with the organic matter in the soil or sediment some influence of the alkylchain length is anticipated. 

 

The number of soils which was used in this test deviates from the recommendation in OECD guideline 106 (2000) in that three soils were used instead of the recommended five soils. In addition the partitioning to soil is not based on a Freundlich isotherm but evaluated based on only one test concentration. These deviations is based on results of earlier adsorption desorption tests with cationic surfactants. The ammonium ions will interact with the negative surface of mineral particles or with negative charges of humic substances. The ionic interactions play a more important role than hydrophobic partitioning with organic matter. The log Koc is therefore considered as a poor predictor of the partitioning behaviour of cationic surfactants in the environment. These earlier results showed that using three soils with at least one loamy sand and a clay soil, can give as much information as using the full number of soils. These earlier tests also revealed that only rarely linear adsorption isotherms were obtained for cationic surfactants and that extrapolation to lower concentrations based on these non-linear isotherms leads to unrealistic results (e.g. RAR primary fatty amines Oct. 2008). According to the Danish EPA (2004) a more reliable method of extrapolation to lower concentrations, is to use the data originating from the lowest measured concentration and to assume that the coefficient remains constant at lower concentrations. The test as described is therefore performed using only one concentration which is as low as reasonably possible in relation to the detection limit.

The initial concentration used for the determination of the soil partitioning constant was 10.2 mg/L (1.9 mg/l for the individual components). The observed aquatic equilibrium concentrations in the experiment range from 1.6 to 10 µg/L. For the prediction of the partitioning of the alkyl polyethylene imidazolines in soil, sediment and suspended matter not the Kd based on organic matter (Koc) will used but the uncorrected Kd because the relation between the organic matter concentration and the sorption observed alone is not sufficient. Research sponsored by APAG CEFIC is currently performed at (UFZ, K.U. Goss, S. Droge) and (IRAS, J. Hermens) to improve the knowledge on bioavailability and partitioning to soil and sediment.

 

Because there is no principal difference between soil and sediments considering the sorption properties and because for cationic surfactants the degree of sorption is not related to the organic carbon content, the value for soil will also be used for sediment and suspended particles. For sludge which consists mainly of organic matter the sorption data as observed for soil is not considered to be representative.

Despite of that mainly for practical reasons (e.g. in the exposure models) a Koc is calculated from this Kd applying the non-hydrophobics QSAR according to the (TGD, 2003). This Koc of 940000 L/kg can be used to predict the sorption in other compartments than soil and sediment. In the table below the distribution constants used in this assessment is summarized:

Distribution constants:

Kp soil   47000 L/kg  Ksoil-water  28200 m3/m3
 Kp susp  94000 L/kg  Ksusp-water  23500 m3/m3
 Kp sed  47000 L/kg  Ksed-water  23500 m3/m3

With a Kpsusp of 94498 L/kg and a concentration of 15 mg/L suspended matter in surface waters, the adsorbed fraction is calculated as 59%.

The relevant emission factors to water and STP sludge as determined in the CAS test have been used in the assessment:

 

In STP

(From CAS test)

 

Fstp.water 0.001

Fstp.sludge 0.0004

Fstp.degr 0.9995

Removal from water >99.999%

 

USES 2.1.2 as incorporated in Chesar was used for the environmental assessment. Due to the restricted possibilities in Chesar, in some cases the modelling results do not accurately reflect the actual situation and where possible some adjustments were made.

 

A waste water treatment simulation test (CAS test) is available. This test shows a removal of 99.999% is achieved in a waste water treatment plant. This removal is mainly due to biodegradation (99.95 %) and additionally a small percentage (0.04%) goes to sludge. The Kp values for solids-water in raw, settled, activated and effluent sewage sludge were adjusted in such a way that the results for removal to sludge in the STP as modelled by EUSES (and therefore Chesar) match the test results as found in the CAS test.

Rosins

No measured data are available for adsorption / desorption for any members of the rosin category. Koc values have been calculated for member substances using the US EPA's KOCWIN model, based on Kow. The substances all fall within the domain of the model and the calculated values are therefore considered suitable for use for this endpoint. Calculated Koc values range from 7.514 to 231739 L/kg (log Koc 0.8759 to 5.37).

Description of key information

Imidazoline DETA
Refined sorption/desorption tests according to OECD 106 have been performed with DETA based tall oil imidazoline. The test resulted in equilibrium constants (Kd's) of 47000, 19000 and 150000 L/kg for loamy sand, silt and clay soil for the DETA based imidazoline. As risk assessment purposes sorption the Kd of loamy sand (Speyer 2.2) for DETA of 47000 L/kg will be used as realistic worst-case.
As there is no direct relationship with the sorption behaviour of the substance and the organic carbon content of the soil because other soil properties like the Cation Exchange Capacity and the pH are maybe even more important to predict the sorption behaviour, no Koc's are given. Despite this, for practical reasons a Koc is calculated from this Kd by applying the non-hydrophobics QSAR according to the (TGD, 2003). This Koc can be used to predict the sorption in other compartments than soil and sediment. Because there is no direct relationship of the sorption with the organic matter content in the soil, there is no principal difference between soil and sediments on respect to the sorption properties. Therefore the same sorption Kd is considered to be acceptable for both soil and sediment.

Rosins
Calculated log Koc values for members of the rosin category range from 0.8759 to 5.37.
Rather than select a Koc for the individual substances, the Koc for use in the risk assessment will be derived from an experimentally derived Koc for Tall oil reaction products with diethylenetriamine.

Key value for chemical safety assessment

Koc at 20 °C:
944 980

Other adsorption coefficients

Type:
log Kp (solids-water in soil)
Value in L/kg:
4.67
at the temperature of:
20 °C

Other adsorption coefficients

Type:
log Kp (solids-water in sediment)
Value in L/kg:
4.67
at the temperature of:
20 °C

Other adsorption coefficients

Type:
log Kp (solids-water in suspended matter)
Value in L/kg:
4.97
at the temperature of:
20 °C

Other adsorption coefficients

Type:
log Kp (solids-water in raw sewage sludge)
Value in L/kg:
12
at the temperature of:
20 °C

Other adsorption coefficients

Type:
log Kp (solids-water in settled sewage sludge)
Value in L/kg:
12
at the temperature of:
20 °C

Other adsorption coefficients

Type:
log Kp (solids-water in activated sewage sludge)
Value in L/kg:
12
at the temperature of:
20 °C

Other adsorption coefficients

Type:
log Kp (solids-water in effluent sewage sludge)
Value in L/kg:
12
at the temperature of:
20 °C

Additional information

Imidazoline DETA

Due to the cationic surface-active properties of tall oil poly ethyleneamine based imidazolines, these substances will adsorb strongly onto the solid phase of soil and sediments. The substance can adsorb both onto the organic fraction and, dependent on the chemical composition, onto the surface of the mineral phase, where sodium and potassium ions can be exchanged against the alkyl ammonium ion. The determination of a Koc from log Kow is not opportune, because the common equations for Koc derivation are not valid for both ionic and surface active substances.

 

The adsorption behaviour DETA based tall oil poly ethyleneamine imidazolines was studied in batch equilibrium experiments according to a refined OECD 106 (Farnback, 2010). In both studies three soils were used, encompassing a range of clay and organic matter. The test substance adsorbed partially onto the container walls which was considered for the determination of the adsorption coefficients. Adsorption kinetics was determined by measurements at different sampling times (up to 24 h), equilibrium was reached after 24 hours but after 3 hours there was only a limited difference observed. Desorption occurred to a lesser extent than adsorption. The tables below present a summary of the most important soil properties and observed partitioning constants for both imidazolines.

Overview of sorption test results of Tall oil diethylenetriamine imidazoline (CAS No 68442-97-7)

 Soil  Clay (%)  Silt (%)  Sand (%)  CEC (meq/100g)  pH  OrgC (%)  Caq (ug/l)  Kd (104cm3/g)  Koc (106cm3/g)
 Speyer 2.2  6.4  12.2  81.4  10 5.4   2.16  4.2  4.7  2
 Eurosoil 4  20.3  75.7  4.1  17.3  6.8  1.31  10  1.9  1.4
 Speyer 6S  42.1  36  21.9 22   7.2  1.75  1.6 15   7.8

From the data it can be observed that the sorption onto Speyer 6S is much higher than to Speyer 2.2 despite of the higher organic matter content in the Speyer 2.2 soil. This can be explained that ionic interactions play a more important role than hydrophobic partitioning with organic matter. Alkyl ammonium ions can interact with the surface of mineral particles or with negative charges of humic substances. The influence of the chain length on the sorption behaviour is therefore expected to be less important only for the hydrophobic interaction with the organic matter in the soil or sediment some influence of the alkylchain length is anticipated. 

 

The number of soils which was used in this test deviates from the recommendation in OECD guideline 106 (2000) in that three soils were used instead of the recommended five soils. In addition the partitioning to soil is not based on a Freundlich isotherm but evaluated based on only one test concentration. These deviations is based on results of earlier adsorption desorption tests with cationic surfactants. The ammonium ions will interact with the negative surface of mineral particles or with negative charges of humic substances. The ionic interactions play a more important role than hydrophobic partitioning with organic matter. The log Koc is therefore considered as a poor predictor of the partitioning behaviour of cationic surfactants in the environment. These earlier results showed that using three soils with at least one loamy sand and a clay soil, can give as much information as using the full number of soils. These earlier tests also revealed that only rarely linear adsorption isotherms were obtained for cationic surfactants and that extrapolation to lower concentrations based on these non-linear isotherms leads to unrealistic results (e.g. RAR primary fatty amines Oct. 2008). According to the Danish EPA (2004) a more reliable method of extrapolation to lower concentrations, is to use the data originating from the lowest measured concentration and to assume that the coefficient remains constant at lower concentrations. The test as described is therefore performed using only one concentration which is as low as reasonably possible in relation to the detection limit.

The initial concentration used for the determination of the soil partitioning constant was 10.2 mg/L (1.9 mg/l for the individual components). The observed aquatic equilibrium concentrations in the experiment range from 1.6 to 10 µg/L. For the prediction of the partitioning of the alkyl polyethylene imidazolines in soil, sediment and suspended matter not the Kd based on organic matter (Koc) will used but the uncorrected Kd because the relation between the organic matter concentration and the sorption observed alone is not sufficient. Research sponsored by APAG CEFIC is currently performed at (UFZ, K.U. Goss, S. Droge) and (IRAS, J. Hermens) to improve the knowledge on bioavailability and partitioning to soil and sediment.

 

Because there is no principal difference between soil and sediments considering the sorption properties and because for cationic surfactants the degree of sorption is not related to the organic carbon content, the value for soil will also be used for sediment and suspended particles. For sludge which consists mainly of organic matter the sorption data as observed for soil is not considered to be representative.

Despite of that mainly for practical reasons (e.g. in the exposure models) a Koc is calculated from this Kd applying the non-hydrophobics QSAR according to the (TGD, 2003). This Koc of 940000 L/kg can be used to predict the sorption in other compartments than soil and sediment. In the table below the distribution constants used in this assessment is summarized:

Distribution constants:

Kp soil   47000 L/kg  Ksoil-water  28200 m3/m3
 Kp susp  94000 L/kg  Ksusp-water  23500 m3/m3
 Kp sed  47000 L/kg  Ksed-water  23500 m3/m3

With a Kpsusp of 94498 L/kg and a concentration of 15 mg/L suspended matter in surface waters, the adsorbed fraction is calculated as 59%.

The relevant emission factors to water and STP sludge as determined in the CAS test have been used in the assessment:

 

In STP

(From CAS test)

 

Fstp.water 0.001

Fstp.sludge 0.0004

Fstp.degr 0.9995

Removal from water >99.999%

 

EUSES 2.1.2 as incorporated in Chesar was used for the environmental assessment. Due to the restricted possibilities in Chesar, in some cases the modelling results do not accurately reflect the actual situation and where possible some adjustments were made.

 

A waste water treatment simulation test (CAS test) is available. This test shows a removal of 99.999% is achieved in a waste water treatment plant. This removal is mainly due to biodegradation (99.95 %) and additionally a small percentage (0.04%) goes to sludge. The Kp values for solids-water in raw, settled, activated and effluent sewage sludge were adjusted in such a way that the results for removal to sludge in the STP as modelled by EUSES (and therefore Chesar) match the test results as found in the CAS test.

Rosins

No measured data are available for adsorption / desorption for any members of the rosin category. Koc values have been calculated for member substances using the USEPA's KOCWIN model, based on Kow. The substances all fall within the domain of the model and the calculated values are therefore considered suitable for use for this endpoint. Calculated Koc values range from 7.514 to 231739 L/kg (log Koc 0.8759 to 5.37).

[LogKoc: 20.0]