Ethanaminium, 2-hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-, esters with C16-18 and C18-unsatd. fatty acids, chlorides

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Study period:

15.12.2008-24.07.2009

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

Guideline:

OECD Guideline 106 (Adsorption - Desorption Using a Batch Equilibrium Method)

Version / remarks:

(2000)

Qualifier:

according to guideline

Guideline:

other: US-EPA Pesticide Assessment Guidelines, Subdivision N. Chemistry: Environmental fate. Section 163-1. Leaching and adsorption/desorption studies. 1982.

Qualifier:

according to guideline

Guideline:

other: Commission Directive 95/36/EC amending Council Directive 91/414/EEC. Annex I, Section 7.1.2. Adsorption and desorption. Official Journal of the European Communities no L172 (1995)

Qualifier:

according to guideline

Guideline:

EPA OPPTS 835.1110 (Activated Sludge Sorption Isotherm)

Version / remarks:

(1998)

GLP compliance:

yes (incl. QA statement)

Type of method:

batch equilibrium method

Media:

soil/sewage sludge

Specific details on test material used for the study:

- Name of test material (as cited in study report): MDEA-Esterquat (unlabelled); Ethanaminium, 2-hydroxy-N-(2-hydroxyethyl)-N,N- dimethyl-, esters with C16-18 and C18 unsaturated fatty acids, chlorides
- Physical state: white solid powder

- Name of test material (as cited in study report): [Me-14C] MDEA-Esterquat (labelled); [Me-14C] Ethanaminium, 2-hydroxy-N-(2-hydroxyethyl)-N,N- dimethyl-, esters with C16-18 and C18 unsaturated fatty acids, chlorides
- Specific activity (if radiolabelling): 530 MBq/g
- Locations of the label (if radiolabelling): Me-14C
- Storage condition of test material: in freezer (<=-15°C) in the dark

Radiolabelling:

yes

Test temperature:

20 +/-2°C

Analytical monitoring:

yes

Details on sampling:

- Concentrations:
adsorption/desorption kinetics: ca. 1 mg/L (stock solutions were prepared in ethanol)
adsorption/desorption isotherms: 0.02, 0.1, 0.5, 1, and 2 mg/L (stock solutions were prepared in ethanol)
- Sampling interval:
adsorption/desorption kinetics: adsorption: sampling was performed after 3, 6, and 26.5 h; desorption: sampling was performed after 3, 18.5, and 24 h
adsorption/desorption isotherms: sampling was performed after 2 h (each)
- Sample storage before analysis: no

Details on matrix:

COLLECTION AND STORAGE
- Geographic location:
a. Tillburg sludge: RWZI Tilburg-Noord, Tilburg, The Netherlands
b. Maaskant sludge: Waterschap de Maaskant, s'Hertogenbosch, The Netherlands
c. Speyer 2.2 soil (Speyer standard soil type 2.2): Rheinland-Pfalz/Hanhofen, Germany, 'Grosser Striet', Nr. 585
d. Speyer 2.3 soil (Speyer standard soil type 2.3): Rheinland-Pfalz/Offenbach, Germany, 'Im Bildgarten', Nr. 570
e. Speyer 6S soil (Speyer standard soil type 6S): Rheinland-Pfalz/Siebeldingen, Germany, 'In der unteren Hohnert', Nr. 3412
- Collection procedures:
a. Tillburg sludge: not reported
b. Maaskant sludge: not reported
c. Speyer 2.2 soil: received from Landwirtschaftliche Untersuchungs- und Forschungsanstalt Speyer, Obere Langgasse 40, 67346 Speyer, Germany
d. Speyer 2.3 soil: received from Landwirtschaftliche Untersuchungs- und Forschungsanstalt Speyer, Obere Langgasse 40, 67346 Speyer, Germany
e. Speyer 6S soil: received from Landwirtschaftliche Untersuchungs- und Forschungsanstalt Speyer, Obere Langgasse 40, 67346 Speyer, Germany
- Sampling depth (cm):
a. Tillburg sludge: not applicable
b. Maaskant sludge: not applicable
c. Speyer 2.2 soil: 0-20 cm
d. Speyer 2.3 soil: 0-20 cm
e. Speyer 6S soil: 0-20 cm
- Storage conditions:
a. Tillburg sludge (dried): ambient temperature
b. Maaskant sludge (dried): ambient temperature
c. Speyer 2.2 soil: refrigerated after receipt at NOTOX; ambient temperature after sieving/air drying
d. Speyer 2.3 soil: refrigerated after receipt at NOTOX; ambient temperature after sieving/air drying
e. Speyer 6S soil: refrigerated after receipt at NOTOX; ambient temperature after sieving/air drying
- Storage length:
a. Tillburg sludge: not reported
b. Maaskant sludge: not reported
c. Speyer 2.2 soil: at least 7 months
d. Speyer 2.3 soil: at least 7 months
e. Speyer 6S soil: at least 7 months
- Sludge preparation: After arrival at NOTOX, the sludges were allowed to settle at ambient temperature for at least 30 min. The water layers were separated as much as possible from the precipitated sludges and discarded. The sludges were centrifuged and the supernatant was decanted. The sludges were frozen at <=-75°C and subject to freeze-drying. After freeze-drying, the sludges were sieved over a 2 mm sieve and dried overnight in an oven at 103°C. The sludges were stored in closed containers at ambient temperature.
- Soil preparation (e.g.: 2 mm sieved; air dried etc.): the soils were air dried and sieved (2 mm)


PROPERTIES
-Sludge texture
a. Tillburg sludge (dry sludge): clay (70.6% organic matter; 41% organic carbon; particle size distribution: 66% fraction < 2 µm, 32% fraction 2 µm-50 µm, 2% fraction 50µm-2 mm)
- Soil/sludge taxonomic classification: clay
- Soil/sludge classification system: USDA
- pH (0.01 M CaCl2): 6.2
- organic carbon: 41%
- CEC (meq/100 g): 134
- Moisture content: 10.4%
b. Maaskant sludge (dry sludge): clay (74.0% organic matter; 43% organic carbon; particle size distribution: 76% fraction < 2 µm, 21% fraction 2 µm-50 µm, 3% fraction 50µm-2 mm)
- Soil/sludge taxonomic classification: clay
- Soil/sludge classification system: USDA
- pH (0.01 M CaCl2): 5.2
- organic carbon: %
- CEC (meq/100 g): 131
- Moisture content: 5.97%

- Soil texture
c. Speyer 2.2 soil: loamy sand
d. Speyer 2.3 soil: sandy loam
e. Speyer 6S soil: clay
- Horizon:
c. Speyer 2.2 soil: 0-20 cm
d. Speyer 2.3 soil: 0-20 cm
e. Speyer 6S soil: 0-20 cm
- Soil taxonomic classification:
c. Speyer 2.2 soil: loamy sand
d. Speyer 2.3 soil: sandy loam
e. Speyer 6S soil: clay
- Soil classification system: USDA
- pH:
c. Speyer 2.2 soil: 5.4 (CaCl2)
d. Speyer 2.3 soil: 6.4 (CaCl2)
e. Speyer 6S soil: 7.2 (CaCl2)
- Organic carbon (%):
c. Speyer 2.2 soil: 2.16% (organic matter: 3.72%)
d. Speyer 2.3 soil: 0.98% (organic matter: 1.69%)
e. Speyer 6S soil: 1.75% (organic matter: 3.02%)
- CEC (meq/100 g):
c. Speyer 2.2 soil: 10
d. Speyer 2.3 soil: 8
e. Speyer 6S soil: 22
- Carbonate as CaCO3: not reported
- Insoluble carbonates (%): not reported
- Extractable Cations (Ca, Mg, Na, K, H) (MEQ/100 g): not reported
- Special chemical/mineralogical features:
- Moisture content (%):
c. Speyer 2.2 soil: 0.94
d. Speyer 2.3 soil: 1.17
e. Speyer 6S soil: 3.72
- Bulk density (g/cm3): not reported
- Biomass (e.g. in mg microbial C/100 mg, CFU or other): not reported

Details on test conditions:

TEST CONDITIONS
- Buffer: no
- pH:
pH of supernatants after
a. the adsorption experiments: 5.6-6.7
b. desorption experiments: 5.9-6.4
pH of supernatants after
a. the adsorption isotherms experiments: 5.5-6.9
b. desorption isotherms experiments: 5.7-6.7

TEST SYSTEM
- Type, size and further details on reaction vessel: polypropylene containers (recovery> 100%) were used due to adsorption experiments (glass container recovery: 66-82%); size: not reported
- Water filtered (i.e. yes/no; type of size of filter used, if any): Milli-Q water was used in the tests
- Amount of soil/sediment/sludge and water per treatment (if simulation test): 0.09 g sludge/40.5 mL 0.01 M CaCl2 solution and 0.45 g soil/40.5 mL 0.01 M CaCl2 solution,
- Soil/sediment/sludge-water ratio (if simulation test): sludge/CaCl2 solution=1:500; soil/CaCl2 solution= 1:100 (based on additional testing)
- Number of reaction vessels/concentration: adsorption/desorption kinetics experiments: 2/1; adsorption/desorption isotherms: 2 each
- Measuring equipment: LSC: Packard TR-2800 (Perkin Elmer Life and Analytical Sciences, Boston, MA, USA); Oxidizer: OX-500 (R.J. Harvey, Zinsser Analytic, Frankfurt, Germany); TLC: 2 D-scanner: Instant Imager (Perkin Elmer Life and Analytical Sciences, Boston, MA, USA)
- Test performed in closed vessels due to significant volatility of test substance: not reported; the test substance, however, has a very low vapour pressure
- Test performed in open system: not reported; the test substance, however, has a very low vapour pressure
- Method of preparation of test solution: stock solutions were prepared in ethanol
- Are the residues from the adsorption phase used for desorption: yes

Sample No.:

#1

Duration:

3 h

Initial conc. measured:

1 other: mg/L

Temp.:

20 °C

Sample no.:

#1

Duration:

3 h

Conc. of adsorbed test mat.:

0.2 other: g/L

Temp.:

20 °C

Type:

Koc

Value:

20 225 L/kg

Type:

log Koc

Value:

4.3 dimensionless

Adsorption and desorption constants:

see below

Recovery of test material:

90-110% (exception Speyer 2.2 soil: 65%; due to the low recoveries the results for Speyer 2.2 soil were considered as not valid)

Concentration of test substance at end of adsorption equilibration period:

The amount of [Me-14C] MDEA-Esterquat adsorbed to sludges and soils after 3 h was approximately
a. 57% for Tilburg sludge
b. 20% for Maaskant sludge
c. 85% for Speyer 2.2 soil
d. 99% for Speyer 2.3 soil and
e. 99% for Speyer 6S

Concentration of test substance at end of desorption equilibration period:

The amount of [Me-14C] MDEA-Esterquat desorbed from the sludges and soils after 3 h was approximately
a. ca. 10% for Tilburg sludge
b. ca. 22% for Maaskant sludge
c. ca. 5% for Speyer 2.2 soil
d. ca. 2 % for Speyer 2.3 soil and
e. ca. 4% for Speyer 6S

Sample no.:

#1

Duration:

3 h

% Adsorption:

57

Sample no.:

#2

Duration:

3 h

% Adsorption:

20

Sample no.:

#3

Duration:

3 h

% Adsorption:

85

Sample no.:

#4

Duration:

3 h

% Adsorption:

99

Sample no.:

#5

Duration:

3 h

% Adsorption:

99

Sample no.:

#1

Duration:

3 h

% Desorption:

ca. 10

Sample no.:

#2

Duration:

3 h

% Desorption:

ca. 22

Sample no.:

#3

Duration:

3 h

% Desorption:

ca. 5

Sample no.:

#4

Duration:

3 h

% Desorption:

ca. 2

Sample no.:

#5

Duration:

3 h

% Desorption:

ca. 4

Transformation products:

yes

Details on results (Batch equilibrium method):

Main Tests
- Sample purity: >98%
- Weighed sludge/soil: sludge: 0.09 g; soil: 0.45 g
- Volume of CaCl2 solution: sludge: 40.5 mL; soil: 40.5 mL
- Initial test substance concentration: adsorption/desorption kinetics experiments: 9.23 mg/L (stock solution prepared in ethanol and diluted with CaCl2); adsorption/desorption isotherms experiments: 1751, 1013, 523, 112, 18.6 mg/L (stock solution prepared in ethanol and diluted with further ethanol; concentrations determined via LSC measurements)
- Test substance concentration in final solution: adsorption/desorption kinetics experiments: 1 mg/L; adsorption/desorption isotherms experiments: 0.02, 0.1, 0.5, 1, and 2 mg/L
- Analytical test substance concentration in final solution: adsorption/desorption kinetics experiments: not measuredadsorption/desorption isotherms experiments: 0.02, 0.1, 0.5, 1, and 2 mg/L (concentration of spike solution was measured by LSC)

MAIN TEST: PERFORMANCE
- Test material stability during adsorption/desorption phase: based on the results, the test substance proved to be not fully stable under the experimental conditions applied
- Experimental conditions maintained throughout the study: Yes
- Buffer/test substance interactions affecting sorption: no buffer used
- Further chemical interactions: not reported
- Buffer-catalyzed degradation of test substance: no buffer used
- Anomalies or problems encountered (if yes): not reported

TRANSFORMATION PRODUCTS
- Range of maximum concentrations in % of the applied amount: Based on the results, the test substance proved to be not fully stable under the experimental conditions applied. The degradation products were neither identified nor quantified.


RESIDUES
- Total unidentified radioactivity (range) of applied amount: not reported
- Extractable residues (% of applied amount at end of study period): not reported
- Non-extractable residues (% of applied amount at end of study period): not reported


VOLATILIZATION
- % of the applied radioactivity present as volatile organics at end of study: not reported

The adsorption/desorption of MDEA-Esterquat C16-18 and C18 unsatd.  was investigated in a study conducted according to OECD Guideline 106 (Adsorption - Desorption Using a Batch Equilibrium Method), US-EPA Pesticide Assessment Guidelines, Subdivision N. Chemistry: Environmental fate. Section 163-1. Leaching and adsorption/desorption studies; 1982), Commission Directive 95/36/EC amending Council Directive 91/414/EEC. Annex I, Section 7.1.2. Adsorption and desorption. Official Journal of the European Communities no L172 (1995), and EPA OPPTS 835.1110 (Activated Sludge Sorption Isotherm) using two sludges and three soils. The sludges were taken from wwtps treating predominantly domestic wastewater. The soils included a loamy sand (Speyer 2.2 soil), a sandy loam (Speyer 2.3 soil) and a clay (Speyer 6S). Adsorption/desorption kinetics were determined at a nominal initial concentration of approximately 1 mg/L. Adsorption and desorption isotherms were determined over a concentration range from approximately 0.02 to 2 mg/L. The adsorption/desorption experiments were carried out at 20 +/- 2°C in the dark on a roller mixer at a soil: 0.01 M CaCl2 solution ratio of 1:100 and a sludge:0.01 M CaCl2 solution ratio of 1:500. Adsorption equilibrium was reached at about 3 -6 hours. Desorption equilibrium was considered to be reached after 3 h, although no real equilibrium seemed to be reached with Masskant sludge. To minimise the effect of decomposition of the test substance on the final results, the isotherms experiment was carried out with a timeline of 2 h for adsorption and 2 h for desorption. More than 93% of the applied activity was recovered at the end of the adsorption and desorption phases, except in the case of Speyer 2.2 soil (65%). Therefore, the results for Speyer 2.2 soil are due to the low recoveries considered not valid. The adsorption/desorption isotherms of [Me-14C] MDEA-Esterquat C16-18 and C18 unsatd. and its degradation products could be described by the Freundlich equation. The Freundlich adsorption coefficients are summarized in the following table:

Adsorption coefficient determination during the isotherm

Test system	Kd (cm³/g)	Kdom (cm³/g)	Kdoc (cm³/g)	r²	Data points
Tilburg sludge	348	492	848	0.9902	10
Maaskant sludge	348	470	809	0.9857	10
Speyer 2.3 soil	4.46 x 10³	264 x 10³	455 x 10³	0.9203	8
Speyer 6S soil	9.38 x 10³	311 x 10³	536 x 10³	0.9693	10

*Speyer 2.2 soil is omitted in the table due to the low recoveries obtained and therefore these results were considered as not valid

During the stability test and the adsorption/desorption kinetic experiment it was found that [Me-14C] MDEA-Esterquat C16-18 and C18 unsatd.  was not fully stable under the experimental conditions based on TLC results. Therefore, the results described should be applied to [Me-14C] the test substance and its degradation products. A Koc=20225 was calculated as the geometric mean of the two sludges and the two soils whereas a Koc=828 was calculated as geometric mean for the two sludges and a Koc=494 x 10³ as geometric mean for the two soils. According to the classification of Blume & Ahlsdorf (1993), these results indicate a high sorption onto sludges and a very high sorption onto soil. As the test substance is readily biodegradable under aerobic conditions, highly biodegrable under anaerobic conditions and not fully stable in the presence of sludges and soils as could be shown during the adsorption/desorption study it can be assumed that both in sludges and soils degradation takes place and decreased the potential for geoaccumulation significantly.

Validity criteria fulfilled:

yes

Conclusions:

The adsorption/desorption of MDEA-Esterquat C16-18 and C18 unsatd. was investigated in a study conducted according to guideline. During the stability test and the adsorption/desorption kinetic experiment it was found that[Me-14C] MDEA-Esterquat was not fully stable under the experimental conditions based on TLC results. Therefore, the results described should be applied to [Me-14C] MDEA-Esterquat and its degradation products. A Koc=20225 was calculated as the geometric mean of the two sludges and the two soils whereas a Koc=828 was calculated as geometric mean for the two sludges and a Koc=494 x 10³ as geometric mean for the two soils.

Executive summary:

The adsorption/desorption of MDEA-Esterquat C16-18 and C18 unsatd. was investigated in a study conducted according to OECD Guideline 106 (Adsorption - Desorption Using a Batch Equilibrium Method), US-EPA Pesticide Assessment Guidelines, Subdivision N. Chemistry: Environmental fate. Section 163-1. Leaching and adsorption/desorption studies; 1982), Commission Directive 95/36/EC amending Council Directive 91/414/EEC. Annex I, Section 7.1.2. Adsorption and desorption. Official Journal of the European Communities no L172 (1995), and EPA OPPTS 835.1110 (Activated Sludge Sorption Isotherm) using two sludges and three soils. The sludges were taken from wwtps treating predominantly domestic wastewater. The soils included a loamy sand (Speyer 2.2 soil), a sandy loam (Speyer 2.3 soil) and a clay (Speyer 6S). During the stability test and the adsorption/desorption kinetic experiment it was found that [Me-14C] MDEA-Esterquat C16-18 and C18 unsatd. was not fully stable under the experimental conditions based on TLC results. Therefore, the results described should be applied to [Me-14C] MDEA-Esterquat C16-18 and C18 unsatd. and its degradation products. A Koc=20225 was calculated as the geometric mean of the two sludges and the two soils whereas a Koc=828 was calculated as geometric mean for the two sludges and a Koc=494 x 10³ as geometric mean for the two soils. According to the classification of Blume & Ahlsdorf (1993), these results indicate a high sorption onto sludges and a very high sorption onto soil. As MDEA-Esterquat C16-18 and C18 unsatd. is readily biodegradable under aerobic conditions, highly biodegrable under anaerobic conditions and not fully stable in the presence of sludges and soils as could be shown during the adsorption/desorption study it can be assumed that both in sludges and soils degradation takes place and decreased the potential for geoaccumulation significantly.

The study is considered as reliable without restriction and satisfies the requirements of the guideline.

Description of key information

Koc=20225 (geometric mean of the two sludges and the two soils)
Koc=828 (geometric mean for the two sludges)
Koc=494 x 10³ (geometric mean for the two soils)

Key value for chemical safety assessment

Koc at 20 °C:

20 225

Additional information

The adsorption/desorption of MDEA-Esterquat C16-18 and C18 unsatd. was investigated in a study conducted according to OECD Guideline 106 (Adsorption - Desorption Using a Batch Equilibrium Method), US-EPA Pesticide Assessment Guidelines, Subdivision N. Chemistry: Environmental fate. Section 163-1. Leaching and adsorption/desorption studies; 1982), Commission Directive 95/36/EC amending Council Directive 91/414/EEC. Annex I, Section 7.1.2. Adsorption and desorption. Official Journal of the European Communities no L172 (1995), and EPA OPPTS 835.1110 (Activated Sludge Sorption Isotherm) using two sludges and three soils. The sludges were taken from wwtps treating predominantly domestic wastewater. The soils included a loamy sand (Speyer 2.2 soil), a sandy loam (Speyer 2.3 soil) and a clay (Speyer 6S).During the stability test and the adsorption/desorption kinetic experiment it was found that [Me-14C] MDEA-Esterquat C16-18 and C18 unsatd. was not fully stable under the experimental conditionsbased on TLC results. Therefore, the results described should be applied to[Me-14C] MDEA-Esterquat C16-18 and C18 unsatd. and its degradation products. A Koc=20225 was calculated as the geometric mean of the two sludges and the two soils whereas a Koc=828 was calculated as geometric mean for the two sludges and a Koc=494 x 10³ as geometric mean for the two soils. According to the classification of Blume & Ahlsdorf (1993), these results indicate a high sorption onto sludges and a very high sorption onto soil. As MDEA-Esterquat C16-18 and C18 unsatd.  is readily biodegradable under aerobic conditions, highly biodegradable under anaerobic conditions and not fully stable in the presence of sludges and soils as could be shown during the adsorption/desorption study it can be assumed that both in sludges and soils degradation takes place and decreased the potential for geoaccumulation significantly.