3-amino-N,N-dimethylpropan-1-aminium 2-C10-13-alkyl benzenesulfonate

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:

2017-05-15 to 2017-08-11

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:

The number of soils which were used deviates from the guideline recommendation in the guideline as three soils were used instead of the recommended five soils. The Freundlich isotherms were not determined and the adsorption / desorption behavior was investigated based on one test item concentration. These deviations from the guideline were on request of the sponsor.

Samples were centrifuged < 3000 g if glass vessels had to be used. Higher centrifugation forces would have been
destructive to these vials.
The indirect method was used for the anionic and the cationic component, although the mass balance was partly < 90%. The test item was not completely extractable from aged soil samples.

Deviations:

yes

Remarks:

see above at "Version / remarks"

Qualifier:

according to guideline

Guideline:

other: Council Regulation (EC) No. 440/2008, Method C.18 (2008)

GLP compliance:

yes (incl. QA statement)

Type of method:

batch equilibrium method

Media:

soil

Radiolabelling:

no

Test temperature:

Nominal: 20 ± 2 °C

Analytical monitoring:

yes

Details on sampling:

Test Procedure:

Test vessels:
50 mL disposable centrifugation tubes or 120 mL disposable glass bottles

Concentration for adsorption / desorption:
Due to different adsorption behavior and with regard to the respective limits of quantification, Tier 2 was performed experiments at two concentrations:
For C10-, C11- and C12- alkylbenzene sulfonic acid: 5.0 mg/L
For N,N-dimethyl-1,3-propanediamine: 6.0 mg/L

Stock solutions:
Stock solutions of 10 g/L ACAR16015 in 25 mL methanol were prepared. 0.1 volume-% of these stock solutions, related to the volume of the aqueous phase inthe soil suspensions, was used for spiking.

Preparation of the soil samples (conditioning):
The soils were weighed into the test vessels and an appropriate volume of 0.01 M CaCl2 solution was added.
After agitation overnight (12 h minimum), the samples were used for adsorption experiments.

Preparation of the samples for adsorption:
The soil samples were conditioned as described above. 0.1 volume-% of the stock solutions, related to the volume of the experiments aqueous phase in the soil suspensions was added in order to obtain the required test concentrations. Afterwards, the samples were agitated.

Preparation of the samples for desorption experiments:
Test vessels from the adsorption experiments were used for this purpose. After completion of the adsorption experiments the test vessels were centrifuged, weighed and the supernatant was replaced by fresh CaCl2 solution. Then the test vessels were agitated again to investigate the desorption behavior of the test item.


Preparation of samples:
The soil suspensions in disposable glass bottles (soil / solution ratio for analysis 1:100) were centrifuged at 3000 rpm (2504 g) and the soil suspensions in centrifugation tubes (soil / solution ratios 1:5 and 1:30) at 4000 rpm (3345 g) after agitation to separate the phases, followed by analysing the concentration of the main components of Benzenesulfonic acid, C10-13-alkyl derivs., compds with N,N-dimethyl-1, 3-propanediamine in the aqueous phase by LC-MS/MS. For analysis of the soil, the aqueous phase was decanted and the soil was extracted. Extracts were also analysed by LC-MS/MS.

Replicates:
All samples were prepared in duplicate.


CONTROLS:
CaCl2 solution was conditioned as described above, followed by separation of the aqueous phase by centrifugation. Then the aqueous phase was fortified according to the concentrations used for the test item samples to verify the stability of the test item in the aqueous phase under test conditions. The samples were agitated as long as the test item sample with the longest agitation period.

Replicates Duplicates


BLANK:
Blank samples were prepared for all soils as described for the test item samples but without fortification with the test item. The samples were agitated as longas the samples with the longest agitation period.

Replicates:
Duplicates (Tier 1), single (Tier 2, Tier 3)


Sample Preparation:

Dilution medium:
Methanol / matrix-conditioned CaCl2 solution (0.01 M) (50:50) containing 0.1% formic acid

Standards:
Stock solutions of 10 g/L of the test item in methanol were prepared and were diluted to calibration standards.
At least 6 calibration standards in the range of 100 to 1000 µg/L were prepared using dilution medium for the quantification of C10-C13 alkylbenzene sulfonic acid.
At least 6 calibration standards in the range of 20 to 500 µg/L were prepared using dilution medium for the quantification of N,N-dimethyl-1,3-propanediamine.

Aqueous phase:
Samples in glass bottles were centrifuged at 3000 rpm (2504 g) for 5 min. Samples in centrifugation tubes were centrifuged at 4000 rpm (3345 g) for 5 min. An aliquot of each aqueous sample was stabilised by dilution with methanol containing 0.2% formic acid (factor 2). Samples were diluted to calibration range with dilution medium, if necessary.

Test vessel extraction:
The test vessels were extracted after removal of the soil by adding 5 mL dilution medium and shaking the test vessels for 10 min. Extracts were measured after filtration using disposable syringe filter.

Soil extraction - ASE:
The soil was extracted by using an accelerated solvent extractor (ASE) for investigation of the sorbed anionic and cationic component. After decantation of the aqueous phase, the soil was used for extraction. Each sample was extracted after addition of 2 g magnesium chloride hexahydrate and 4 g silica gel with 2-propanol : HPLC water (50 : 50). For parameters of the extraction method see below. Extracts were transferred quantitatively into a 100 mL measuring flask and filled up with
2-propanol : HPLC water (50 : 50). Aliquots were diluted with the extract of a blank sample to calibration range.

Parameters of the ASE method:
Preheat: 1 min
Heat: 6 min
Static: 10 min
Flush: 50 % (v/v)
Purge: 90 sec
Cycles: 3
Pressure: 1500 psi
Temperature:125 °C
Solvent: 2-propanol : HPLC water (50 : 50)

Soil extraction – Sodium hydroxide:
The basic extraction method was used for investigation of the sorbed cationic component. After decantation of the aqueous phase, the soil was extracted with 10 mL aqueous sodium hydroxide solution 0.1 mol/L : acetonitrile (50 : 50) for 30 min at 70 °C. The extraction was repeated twice, the extracts were transferred quantitatively into a 50 mL measuring flask and filled up to the mark with the extraction medium. Aliquots were diluted with the extract of a blank sample to calibration range.

Samples for method validation:
Samples were prepared as described above (‘Preparation of the soil samples (conditioning)’). The aqueous phases were decanted and spiked with test item at 1 x LOQ level. Additional aqueous phase conditioned with LUFA soil 2.4 was spiked with test item at 10 x LOQ level. Blank samples were prepared accordingly but without spiking with test item. All samples were diluted with methanol containing 0.2% formic acid by factor 2. The samples of 10 x LOQ level were additionally diluted with dilution medium by factor 2 to calibration range for analysis of C10-, C11- and C12- alkylbenzene sulfonic acid.

Sample storage:
All samples were stored at room temperature prior and after analysis. The stability of calibration standards and samples after dilution with acetonitrile was confirmed during method development (non-GLP).

Matrix no.:

#2

Matrix type:

loamy sand

% Clay:

8.5

% Silt:

11.3

% Sand:

80.2

% Org. carbon:

1.47

pH:

>= 6.8 - <= 7.2

CEC:

7.6 other: mval/100 g

Matrix no.:

#3

Matrix type:

other: silty sand

% Clay:

0.412

% Silt:

8.6

% Sand:

29.3

% Org. carbon:

62.1

pH:

>= 6.8 - <= 7.5

CEC:

4.9 other: mval/100 g

Matrix no.:

#4

Matrix type:

clay loam

% Clay:

25.2

% Silt:

42.3

% Sand:

32.6

% Org. carbon:

1.74

pH:

>= 6.9 - <= 7.6

CEC:

22 other: mval/100 g

Details on matrix:

Relevant Characteristics of Soils for Adsorption / Desorption
Soil Parameter
LUFA 2.2 LUFA 2.3 LUFA 2.4
Soil type (LUFA Soils)1) Loamy sand Silty sand Clayey loam
pH (0.01 M CaCl2)2) soil/solution ratio 1:5 6.8 7.5 7.6
pH (0.01 M CaCl2)2) soil/solution ratio 1:30 6.8 6.8 7.4
pH (0.01 M CaCl2)2) soil/solution ratio 1:100 7.2 6.9 6.9
Organic Carbon [%]3) 1.47 0.412 1.74
Clay (< 0.002 mm) [%]3) 8.5 8.6 25.2
Silt (0.002-0.063 mm) [%]3) 11.3 29.3 42.3
Sand (0.063-2 mm) [%]3) 80.2 62.1 32.6
Cation exchange capacity [mval/100 g] 3) 7.6 4.9 22
1) according to German DIN
2) determined during the course of the study
3) determined externally at AGROLAB GMBH (non-GLP)

Reason for the selection:
The content of organic carbon of the selected soils differ significantly. These matrices are suitable for the conduction of the study because all parameters with impact on the adsorption / desorption behavior of a chemical substance differ significantly (organic carbon, clay content, cation exchange capacity and soil texture).

Origin of soils:
Landwirtschaftliche Untersuchungs- und Forschungsanstalt LUFA Speyer, Obere Langgasse 40, 67346 Speyer, Germany


 
Date of receipt:
LUFA 2.2 (batch: F2.24016): 2016-10-24
LUFA 2.3 (batch: F2.34116): 2016-10-24
LUFA 2.4 (batch: F2.44116): 2016-10-24

Storage at test facility:
Room temperature, in closed containers

Expiry date:
According to test facility standard operation procedure, the expiry date was set to five years after receipt of the soils.
LUFA 2.2 (batch: F2.24016): 2021-10-24
LUFA 2.3 (batch: F2.34116): 2021-10-24
LUFA 2.4 (batch: F2.44116): 2021-10-24

Characterization date:
The soils were characterized in relation to their organic carbon content and cation exchange capacity externally at Agrolab GmbH.
LUFA 2.2 (batch: F2.24016): from 2017-02-14 to 2017-02-21
LUFA 2.3 (batch: F2.34116): from 2017-02-14 to 2017-02-21
LUFA 2.4 (batch: F2.44116): from 2017-02-14 to 2017-02-21

CaCl2 solution:
Deionised water was used to prepare the CaCl2 solution (0.01 M).

Soil / Solution ratio:
Due to different adoption behavior of active ingredients, Tier 2 was performed with soil / solution ratios:

For C10-, C11- and C12- alkylbenzene sulfonic acid: 1:30 and 1:5
For N,N-dimethyl-1,3-propanediamine: 1:100

Agitation:
By horizontal shaker at 150 rpm or by overhead shaker. Frequency was adjusted to avoid sedimentation of soil particles during equilibration.

Details on test conditions:

CaCl2 solution:
Deionised water was used to prepare the CaCl2 solution (0.01 M).

Soil / Solution ratio:
Due to different adoption behavior of active ingredients, Tier 2 was performed with soil / solution ratios:
For C10-, C11- and C12- alkylbenzene sulfonic acid: 1:30 and 1:5
For N,N-dimethyl-1,3-propanediamine: 1:100

Agitation:
By horizontal shaker at 150 rpm or by overhead shaker. Frequency was adjusted to avoid sedimentation of soil particles during equilibration.

Test temperature:
20 +/- 2 °C 

Key result

Sample No.:

#1

Type:

Kd

Value:

65 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:5

% Org. carbon:

1.47

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#1

Type:

Koc

Value:

4 407 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:5

% Org. carbon:

1.47

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#1

Type:

other: Kdes

Value:

211 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:5

% Org. carbon:

1.47

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#2

Type:

Kd

Value:

6 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#2

Type:

Koc

Value:

1 462 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#2

Type:

other: Kdes

Value:

33 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#3

Type:

Kd

Value:

179 L/kg

pH:

7.6

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio

% Org. carbon:

1.74

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#3

Type:

Koc

Value:

10 278 L/kg

pH:

7.6

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:5

% Org. carbon:

1.74

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#3

Type:

other: Kdes

Value:

194 L/kg

pH:

7.6

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:5

% Org. carbon:

1.74

Remarks on result:

other: C10-alkylbenzene sulfonic acid

Key result

Sample No.:

#4

Type:

Koc

Value:

175 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:5

% Org. carbon:

1.47

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#4

Type:

Koc

Value:

11 915 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:5

% Org. carbon:

1.47

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#4

Type:

other: Kdes

Value:

187 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:5

% Org. carbon:

1.47

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#5

Type:

Kd

Value:

13 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#5

Type:

Koc

Value:

3 138 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#5

Type:

other: Kdes

Value:

51 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#6

Type:

Kd

Value:

85 L/kg

pH:

7.4

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:30

% Org. carbon:

1.74

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#6

Type:

Koc

Value:

4 862 L/kg

pH:

7.4

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:30

% Org. carbon:

1.74

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#6

Type:

other: Kdes

Value:

984 L/kg

pH:

7.4

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:30

% Org. carbon:

1.74

Remarks on result:

other: C11-alkylbenzene sulfonic acid

Key result

Sample No.:

#7

Type:

Kd

Value:

93 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:30

% Org. carbon:

1.47

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#7

Type:

Koc

Value:

6 298 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:30

% Org. carbon:

1.47

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#7

Type:

other: Kdes

Value:

939 L/kg

pH:

6.8

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:30

% Org. carbon:

1.47

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#8

Type:

Kd

Value:

27 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#8

Type:

Koc

Value:

6 627 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#8

Type:

other: Kdes

Value:

79 L/kg

pH:

7.5

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:5

% Org. carbon:

0.412

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#9

Type:

Kd

Value:

193 L/kg

pH:

7.4

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:30

% Org. carbon:

1.74

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#9

Type:

Koc

Value:

11 087 L/kg

pH:

7.4

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:30

% Org. carbon:

1.74

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#9

Type:

other: Kdes

Value:

1 034 L/kg

pH:

7.4

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:30

% Org. carbon:

1.74

Remarks on result:

other: C12-alkylbenzene sulfonic acid

Key result

Sample No.:

#10

Type:

Kd

Value:

143 L/kg

pH:

7.2

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:100

% Org. carbon:

1.47

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Key result

Sample No.:

#10

Type:

Koc

Value:

9 695 L/kg

pH:

7.2

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:100

% Org. carbon:

1.47

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Key result

Sample No.:

#10

Type:

other: Kdes

Value:

326 L/kg

pH:

7.2

Temp.:

20 °C

Matrix:

LUFA 2.2 soil/solution ratio 1:100

% Org. carbon:

1.47

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Key result

Sample No.:

#11

Type:

Kd

Value:

205 L/kg

pH:

6.9

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:100

% Org. carbon:

0.412

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Key result

Sample No.:

#11

Type:

Koc

Value:

49 859 L/kg

pH:

6.9

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:100

% Org. carbon:

0.412

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Key result

Sample No.:

#11

Type:

other: Kdes

Value:

443 L/kg

pH:

6.9

Temp.:

20 °C

Matrix:

LUFA 2.3 soil/solution ratio 1:100

% Org. carbon:

0.412

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Key result

Sample No.:

#12

Type:

Kd

Value:

515 L/kg

pH:

6.9

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:100

% Org. carbon:

1.74

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Key result

Sample No.:

#12

Type:

Koc

Value:

29 590 L/kg

pH:

6.9

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:100

% Org. carbon:

1.74

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Key result

Sample No.:

#12

Type:

other: Kdes

Value:

889 L/kg

pH:

6.9

Temp.:

20 °C

Matrix:

LUFA 2.4 soil/solution ratio 1:100

% Org. carbon:

1.74

Remarks on result:

other: N,N-dimethyl-1,3-propanediamine

Results– Temperature, Dry Weights, pH Values

Temperature

The temperature was in the range of 20 ± 2 °C during the course of the study.

Dry Weights

The dry weight of each solid matrix was determined.

 

Soil Dry Weights

Mean values (n = 3)

	Soil type
	LUFA 2.2	LUFA 2.3	LUFA 2.4
soil dry weight [%]	92.3	96.1	90.4

 

 pH Values

The pH values of the aqueous media of the test systems were measured before and after equilibration with the corresponding soils and after addition of the test item. Results are shown in the following table.

 

pH Values of the Aqueous Media

Soil / solution ratios 1:5, 1:30 and 1:100

Soil / solution ratio 1:5	Soil type
	LUFA 2.2	LUFA 2.3	LUFA 2.4
0.01 M CaCl2	8.4	8.4	8.4
after soil contact	6.8	7.5	7.6
after addition of the test item	6.5	6.9	7.8
Soil / solution ratio 1:30	Soil type
	LUFA 2.2	LUFA 2.3	LUFA 2.4
0.01 M CaCl2	7.2	7.2	7.2
after soil contact	6.8	6.8	7.4
after addition of the test item	7.0	6.9	7.5
Soil / solution ratio 1:100	Soil type
	LUFA 2.2	LUFA 2.3	LUFA 2.4
0.01 M CaCl2	6.3	6.3	6.3
after soil contact	7.2	6.9	6.9
after addition of the test item	7.0	7.0	6.9

Results –C10-C13 alkylbenzene sulfonic acid

Results of Tier 1 -C10-C13 alkylbenzene sulfonic acid

During Tier 1 experiments have been conducted to find the optimal matrix / solution ratio for each matrix. Therefore, the amount adsorbed at equilibrium was determined. In addition, test item stability was demonstrated by measuring test item control samples with conditioned CaCl₂ solution but without soil during the experiments. The mass balance and the test vessel adsorption was evaluated.

 

 

 Adsorption Experiments -C10-C13 alkylbenzene sulfonic acid

Experiments have been conducted in LUFA soils 2.2 and 2.4 using a soil / solution ratio of 1:20 and 1:40. Samples were taken after 24 and 48 hours and the aqueous phase was analysed. C10-, C11- and C12- alkylbenzene sulfonic acid were analysed for the anionic component of the test item, C10-C13 alkylbenzene sulfonic acid. The alkylbenzene sulfonic acids showed increasing adsorption with increasing alkyl chain lengths. The determined adsorption values are shown in the tables below. With regard to these results, a soil solution ratio of 1:30 and an agitation time of 48 h were selected for Tier 2 experiments.

Tier 1:LUFA 2.2 Soil / Solution Ratios 1:20 and 1:40 -
C10-C13 alkylbenzene sulfonic acid

Soil / Solution Ratio	Applied concentration, test item [mg/L]	Sampling point [h]	Adsorption C10 alkyl benzene sulfonic acid[%]	Adsorption C11 alkyl benzene sulfonic acid[%]	Adsorption C12 alkyl benzene sulfonic acid[%]
1:20	6.25	24	32	61	85
		48	40	65	86
1:40	6.25	24	30	52	72
		48	26	50	73

 

 Tier 1:LUFA 2.4 Soil / Solution Ratios 1:20 and 1:40 -
C10-C13 alkylbenzene sulfonic acid

Soil / Solution Ratio	Applied concentration, test item [mg/L]	Sampling point [h]	Adsorption C10 alkyl benzene sulfonic acid[%]	Adsorption C11 alkyl benzene sulfonic acid[%]	Adsorption C12 alkyl benzene sulfonic acid[%]
1:20	6.25	24	36	63	85
		48	53	74	90
1:40	6.25	24	25	43	68
		48	24	46	72

 

Test Item Stability in the Aqueous Phase-C10-C13 alkylbenzene sulfonic acid

The stability of the component C10-C13 alkylbenzene sulfonic acidwas verified by the recovery rates of test item control samples (84% to 113% related to the nominal concentration after 48 h). The test item control samples were prepared by conditioning 0.01 M CaCl₂ solution with soil. After separation of the phases, the aqueous phase was spiked with the test item. The recovery rates obtained are shown in the tables below.

 

Tier 1:Test Item Control Samples LUFA 2.2 -C10-C13 alkylbenzene sulfonic acid

Soil / Solution Ratio	Applied concentration, test item [mg/L]	Sampling point [h]	Recovery Rate C10 alkyl benzene sulfonic acid[%]	Recovery Rate C11 alkyl benzene sulfonic acid[%]	Recovery Rate C12 alkyl benzene sulfonic acid[%]
1:20	6.25	24	111	114	101
		48	113	104	95
1:40	6.25	24	92	93	90
		48	88	88	84

 

 Tier 1:Test Item Control Samples LUFA 2.4 -C10-C13 alkylbenzene sulfonic acid

Soil / Solution Ratio	Applied concentration, test item [mg/L]	Sampling point [h]	Recovery Rate C10 alkyl benzene sulfonic acid[%]	Recovery Rate C11 alkyl benzene sulfonic acid[%]	Recovery Rate C12 alkyl benzene sulfonic acid[%]
1:20	6.25	24	90	94	90
		48	89	89	85
1:40	6.25	24	101	97	92
		48	90	95	86

 

 

Mass Balance and Test Vessel Adsorption -C10-C13 alkylbenzene sulfonic acid

To determine the mass balance after 48 h and the test vessel adsorption, samples with a soil / solution ratio of 1:20 were used. The soil was extracted by using accelerated solvent extraction (ASE) and the test vessels were extracted after removal of the soil. The parental mass balance was ≥ 87% for LUFA 2.2 and ≥ 84% for LUFA 2.4. For aged samples, no higher recoveries could be obtained. Although the mass balance was below 90%, the indirect method was used during Tier 2 by calculating the mass in the solid phase at each sampling point from the measured concentration in the aqueous phase, as test item stability has been confirmed by test item control samples. The recovery rates and mass balance are presented in the tables below.

The test vessel adsorption for C10-C13 alkylbenzene sulfonic acid was negligible (≤ 1.9%) and therefore not determined during Tier 2.

 

 Tier 1:Mass Balance LUFA 2.2 soil -C10-C13 alkylbenzene sulfonic acid
soil / solution ratio 1:20, applied test item concentration: 6250 µg/L, n=2

	Sampling point [h]	Recovery rate from aqueous phase [%]	Recovery rate from test vessel [%]	Recovery rate from solid phase [%]	Mass balance^1) [%]
Adsorption C10 alkyl benzene sulfonic acid[%]	48	60	0.8	32	93
Adsorption C11 alkyl benzene sulfonic acid[%]	48	35	1.7	54	91
Adsorption C12 alkyl benzene sulfonic acid[%]	48	14	1.9	71	87

1)          Sum of aqueous phase, solid phase and test vessel

 

Tier 1:Mass Balance LUFA 2.4 soil -C10-C13 alkylbenzene sulfonic acid
soil / solution ratio 1:20, applied test item concentration: 6250 µg/L, n=2

	Sampling point [h]	Recovery rate from aqueous phase [%]	Recovery rate from test vessel [%]	Recovery rate from solid phase [%]	Mass balance^1) [%]
Adsorption C10 alkyl benzene sulfonic acid[%]	48	55	0.3	29	84
Adsorption C11 alkyl benzene sulfonic acid[%]	48	33	0.6	51	85
Adsorption C12 alkyl benzene sulfonic acid[%]	48	16	1.0	71	88

1)          Sum of aqueous phase, solid phase and test vessel

Tier 2:Adsorption Kinetics -C10-C13 alkylbenzene sulfonic acid

The determination for adsorption kinetics was performed with a nominal test item concentration of 5.00 mg/L. This concentration was selected with regard to the LOQ of the analytical method. Two different soil / solution ratios were used for adsorption experiments, 1:5 and 1:30. Results are shown in the tables below for the respective alkylbenzene sulfonic acid. Dependent on the alkyl chain-length and the soil type, either the samples with the soil / solution ratio 1:5 or the samples of 1:30 were used for evaluation. Samples were agitated for 48 h and samples of the aqueous phase were measured at defined sampling points. In addition, test item control samples were analysed. The percentage of adsorption and recovery rate for the test item control are given after 48 h and this sampling was used to calculate the distribution coefficients K_d and the corresponding organic carbon normalized distribution coefficients K_OC.

 

Measured Amounts in Aqueous Phase, Calculated Amount for Solid Matrices, Percent of Adsorption and Distribution Coefficients K_d and K_OC for C10 alkylbenzene sulfonic acid

Applied test item concentration: 5000 µg/L, n = 2
equilibration time: 48 h

Soil type	msoil [g]	Vaq [mL]	m^adss[µg]	Kd [mL/g]	KOC [mL/g]	Adsorption [%]	Recovery Control [%]^1)
LUFA 2.2	3.69	20	92.3	65	4407	92	113
LUFA 2.3	3.84	20	53.7	6	1462	54	97
LUFA 2.4	3.62	20	97.0	179	10278	97	94

m_soil          = used amount of soil (dry weight)

V_aq            = used volume of aqueous phase

m^ads_s         = amount adsorbed to soil

1)               = recovery related to initially measured (0 h) concentration

2)               = ½ LOQ was used for calculations since measured concentration was below the lowest
  calibration standard

 

 Measured Amounts in Aqueous Phase, Calculated Amount for Solid Matrices, Percent of Adsorption and Distribution Coefficients K_d and K_OC for C11 alkylbenzene sulfonic acid

Applied test item concentration: 5000 µg/L, n = 2
equilibration time: 48 h

Soil type	msoil [g]	Vaq [mL]	m^adss[µg]	Kd [mL/g]	KOC [mL/g]	Adsorption [%]	Recovery Control [%]^1)
LUFA 2.2	3.69	20	97.0	175	11915	97	98
LUFA 2.3	3.84	20	71.3	13	3138	71	97
LUFA 2.4	0.904	30	108	85	4862	72	92

m_soil          = used amount of soil (dry weight)

V_aq            = used volume of aqueous phase

m^ads_s         = amount adsorbed to soil

1)               = recovery related to initially measured (0 h) concentration

2)               = ½ LOQ was used for calculations since measured concentration was below the lowest
  calibration standard

Measured Amounts in Aqueous Phase, Calculated Amount for Solid Matrices, Percent of Adsorption and Distribution Coefficients K_d and K_OC for C12 alkylbenzene sulfonic acid

Applied test item concentration: 5000 µg/L, n = 2
equilibration time: 48 h

Soil type	msoil [g]	Vaq [mL]	m^adss[µg]	Kd [mL/g]	KOC [mL/g]	Adsorption [%]	Recovery Control [%]^1)
LUFA 2.2	0.923	30	111	93	6298	74	81
LUFA 2.3	3.84	20	84.0	27	6627	84	88
LUFA 2.4	0.904	30	128	193	11087	85	94

m_soil          = used amount of soil (dry weight)

V_aq            = used volume of aqueous phase

m^ads_s         = amount adsorbed to soil

1)               = recovery related to initially measured (0 h) concentration

 

Tier 3: Desorption Kinetics-C10-C13 alkylbenzene sulfonic acid

The desorption behavior of the test item was determined after 48 h adsorption. The following tables show the desorption coefficient K_des. Since the desorption coefficient is higher than the adsorption coefficient K_d, the test item adsorption is assumed to be not completely reversible. As the concentration of the analytes was partly below the LOQ, desorption and K_des had to be calculated with ½ LOQ. Calculated values are marked.

 

Percent of Desorption and Desorption Coefficient K_des for
C10 alkylbenzene sulfonic acid

Applied test item concentration: 5000 µg/L, n = 2

Soil Type	msoil[g]	Vaq[mL]	m^desaq(eq) [µg]	m^adss(eq) [µg]	Kdes[mL/g]	Desorption [%]
LUFA 2.2^1)	3.69	20	2.31	92.3	211	3
LUFA 2.3	3.84	20	7.24	53.7	33	13
LUFA 2.4^1)	3.62	20	2.69	97.0	194	3

m_soil          = used amount of soil (dry weight)

V_aq            = used volume of aqueous phase

m^des_aq        = amount of test item measured in the aqueous phase after desorption step

(without entrained water)

m^ads_s          = amount of test item adsorbed to soil at equilibrium

1)               = measured values at 48 h were below LOQ, endpoints were calculated with ½ LOQ

 

Percent of Desorption and Desorption Coefficient K_des for
C11 alkylbenzene sulfonic acid

Applied test item concentration: 5000 µg/L, n = 2

Soil Type	msoil[g]	Vaq[mL]	m^desaq(eq) [µg]	m^adss(eq) [µg]	Kdes[mL/g]	Desorption [%]
LUFA 2.2^1)	3.69	20	2.73	97.0	187	3
LUFA 2.3	3.84	20	6.62	71.3	51	9
LUFA 2.4^1)	0.904	30	3.51	108	984	3

m_soil          = used amount of soil (dry weight)

V_aq            = used volume of aqueous phase

m^des_aq        = amount of test item measured in the aqueous phase after desorption step

(without entrained water)

m^ads_s          = amount of test item adsorbed to soil at equilibrium

1)               = measured values at 48 h were below LOQ, endpoints were calculated with ½ LOQ

 

Percent of Desorption and Desorption Coefficient K_des for
C12 alkylbenzene sulfonic acid

Applied test item concentration: 5000 µg/L, n = 2

Soil type	msoil[g]	Vaq[mL]	m^desaq(eq) [µg]	m^adss(eq) [µg]	Kdes[mL/g]	Desorption [%]
LUFA 2.2^1)	0.923	30	3.71	111	939	3
LUFA 2.3	3.84	20	5.18	84.0	79	6
LUFA 2.4^1)	0.904	30	3.98	128	1034	3

m_soil          = used amount of soil (dry weight)

V_aq            = used volume of aqueous phase

m^des_aq        = amount of test item measured in the aqueous phase after desorption step

(without entrained water)

m^ads_s          = amount of test item adsorbed to soil at equilibrium

1)               = measured values at 48 h were below LOQ, endpoints were calculated with ½ LOQ

 

The respective figures of the desorption kinetics show that the desorption equilibrium is not reached after 48 h. This effect is apparently related to the chemical composition of the test item or can be related to the specific properties of this component of the test item. The concentration of the analytes in the aqueous phase and the calculated desorption decrease over time (until concentration was below LOQ for some soils). As test item stability was confirmed by test item control samples during Tier 1 and Tier 2, the results can be explained by ongoing adsorption of the alkylbenzene sulfonic acids after renewal of the aqueous phase.

Discussion of the Results for C10-C13 alkylbenzene sulfonic acid

The experiments for adsorption and desorption kinetics showed that the adsorption of the alkylbenzene sulfonic acids to the soil particles takes place slowly. The adsorption equilibrium was not reached for each analysed compound using a soil / solution ratio of 1:30. As recommended by the guideline, evaluation of phenomena which lead to the steady decrease of the test item concentration in the aqueous phase was conducted.

 

As the results of the test item control samples measured during Tier 2 neither indicated depletion of the test item in the aqueous phase by adsorption processes on test vessels nor by degradation processes, the test item was considered to be stable in the test system over 48 h.

 

The impactof soil parameters on the adsorption / desorption behavior of a chemical substance was considered by the selection of soils which differ significantly in their composition and physical properties. The soil type apparently does not affect the achievement of the adsorption equilibrium and the ionisation of the alkylbenzene sulfonates is not affected by the pH value in the study range from 5.0 to 7.5.

 

To investigate the agitation time which is necessary to reach the adsorption equilibrium and to verify if an agitation time longer than 48 h (as recommended by the guideline) is applicable for the anionic compound, additional experiments have been conducted over a period of 168 h. The soil / solution ratio of 1:30 was used, as measured concentrations below the LOQ should be avoided. The results are summarized in the table below. Whereas the adsorption increased over time, the recovery rate for test item control samples decreased for the aqueous phase. At the same time, increasing test vessel adsorption was determined. The adsorption increased until the concentration in the aqueous phase was below the LOQ of the analytical method without showing an adsorption equilibrium in 168 h. Thus, longer agitation times than recommended by the guideline do not result in a definitive adsorption equilibrium and are therefore not applicable for this test item.

 

A higher soil / solution of 1:5 was used to obtain the adsorption equilibrium faster and these experiments were used for evaluation of the adsorption in suspensions of some soils.

 

 

 Additional Experiment – Agitation Time 168 h

Applied test item concentration: 5000 µg/L, soil /solution ratio: 1:30

C10 alkylbenzene sulfonic acid
Sampling	24 h		48 h		72 h		96 h		168 h
Soil Type	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]
LUFA 2.2	29	n.d.	44	n.d.	56	105	71	104	85	101 (3^1))
LUFA 2.3	9	n.d.	12	n.d.	18	105	23	102	42	100 (3^1))
LUFA 2.4	33	n.d.	49	n.d.	69	98	79	97	95	96 (3^1))
C11 alkylbenzene sulfonic acid
Sampling	24 h		48 h		72 h		96 h		168 h
Soil Type	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]
LUFA 2.2	54	n.d.	66	n.d.	70	94	84	89	94	76 (10^1))
LUFA 2.3	21	n.d.	28	n.d.	36	94	44	96	57	79 (12^1))
LUFA 2.4	56	n.d.	68	n.d.	83	91	89	90	97	81 (10^1))
C12 alkylbenzene sulfonic acid
Sampling	24 h		48 h		72 h		96 h		168 h
Soil Type	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]	Ads [%]	Control [%]
LUFA 2.2	68	n.d.	78	n.d.	82	75	92	70	96	55 (28^1))
LUFA 2.3	45	n.d.	57	n.d.	56	75	65	85	77	51 (27^1))
LUFA 2.4	79	n.d.	83	n.d.	90	72	94	82	97	56 (29^1))

Ads              = adsorption calculated from concentration in aqueous phase, mean value of two replicates

Control        = recovery rate of the test item control sample related to nominal concentration, mean value of two

                       replicates

n.d.              = not determined

1)                  = test vessel adsorption [%]

 

With regard to the results obtained during the experiments over 168 h, a higher soil / solution ratio of 1:5 was chosen to accelerate the adsorption process. Inappropriately, high soil / solution ratios also enhance the test item depletion in the aqueous phase with the disadvantage that the certainty in thedetermination of the remaining test item concentration decreases. Measured concentrations were partly below the LOQ of the analytical method.

 

It is considered that the steady decrease of the test item in the aqueous phase is related to its chemical composition and the presence of the diamine which can work as a bridge between negative charges. To provide plausible values for K_d and K_OC, data have been calculated for the best suitable soil / solution ratio (1:5 or 1:30) for each analyte regarding the degree of adsorption on the one hand and the measured concentrations on the other hand.

Results –N,N-dimethyl-1,3-propanediamine

Results of Tier 1 -N,N-dimethyl-1,3-propanediamine

During Tier 1, experiments have been conducted to find the optimal matrix / solution ratio and the time to reach equilibrium for each matrix. Therefore, the amount adsorbed at equilibrium was determined. In addition, test item stability was demonstrated by measuring test item control samples with conditioned CaCl₂ solution but without soil during the experiments. The mass balance was evaluated.

 

 

Adsorption Experiments -N,N-dimethyl-1,3-propanediamine

Experiments have been conducted in LUFA soils 2.2 and 2.4 using a soil / solution ratio of 1:20 and 1:40. Samples were taken after 24 and 48 hours and the concentration of N,N-dimethyl-1,3-propanediamine was analysed in the aqueous phase. As the adsorption was high, measured concentrations were partly below the LOQ. Test item control samples (aqueous medium conditioned with soil, separated and spiked with the test item) showed stability of N,N-dimethyl-1,3-propanediamine in the test system.The determined adsorption values are shown in the table below. With regard to these results, a soil solution ratio of 1:100 and an agitation time of 24 h was selected for Tier 2 experiments.

 

Tier 1:Adsorption with Soil / Solution Ratios 1:20 and 1:40 -
N,N-dimethyl-1,3-propanediamine

Soil / solution ratio	Applied concentration, test item [mg/L]	Sampling point [h]	Adsorption in LUFA 2.2 [%]	Adsorption in LUFA 2.4 [%]
1:20	6.25	24	93	98
		48	98	99
1:40	6.25	24	90	95
		48	92	98

 

 

Test Item Stability in the Aqueous Phase -N,N-dimethyl-1,3-propanediamine

The stability of the cationic component N,N-dimethyl-1,3-propanediamine was verified by the recovery rates of test item control samples (98% to 107% related to the nominal concentration after 48 h) in soil-conditioned 0.01 M CaCl₂ solution. The determined values are shown in the table below.

 

 Tier 1:Test Item Control Samples -N,N-dimethyl-1,3-propanediamine

Soil / solution ratio	Applied concentration, test item [mg/L]	Sampling point [h]	Recovery rate LUFA 2.2[%]	Recovery rate LUFA 2.4[%]
1:20	6.25	24	109	104
		48	100	102
1:40	6.25	24	103	103
		48	107	98

 

Mass Balance and Test Vessel Adsorption -N,N-dimethyl-1,3-propanediamine

During preliminary investigations prior to the start of the study the extraction efficiency of the test item was evaluated by extraction of aged as well as freshly spiked soil samples. The soil was extracted with formic acid or trifluoroacetic acid at room temperature (three extraction steps for each method with ultrasonic treatment) resulting in a poor extraction efficiency. In addition, the soil was extracted by using ASE as described above for C10-C13 alkylbenzene sulfonic acid resulting in negligible recovery of N,N-dimethyl-1,3-propanediamine.

The highest extraction efficiency was obtained after basic extraction at higher temperatures To determine the mass balance after 48 h and the test vessel adsorption during Tier 1, samples with a soil / solution ratio of 1:20 were used. The soil was extracted with sodium hydroxide at 70 °C. The parental mass balance was 28% for LUFA 2.2 and 18% for LUFA 2.4. Although the basic extraction resulted in the highest recovery, the recovery of the cationic component of the test item was still insufficient to fulfil the mass balance requirements of the guideline. Though the mass balance was below 90%, due to strong adsorption of the analyte to soil and bad extraction efficiency, the stability of the component could be confirmed by the results of the test item control samples in conditioned 0.01 M CaCl₂ solution. Therefore, the indirect method was used during Tier 2 by calculating the mass in the solid phase at each sampling point from the measured concentration in the aqueous phase.

 

Adsorption to the test vessel was negligible and test vessel adsorption was therefore not evaluated during Tier 2.

 Tier 1:Mass Balance -N,N-dimethyl-1,3-propanediamine
soil / solution ratio 1:20, applied test item concentration: 6250 µg/L, n=2

	Sampling point [h]	Recovery rate from aqueous phase [%]	Recovery rate from test vessel [%]	Recovery rate from solid phase [%]	Mass balance^1) [%]
Recovery rate in LUFA 2.2 [%]	48	2	0	26	28
Recovery rate in LUFA 2.4 [%]	48	1	0	18	18

1)          Sum of aqueous phase, solid phase and test vessel

 

Tier 2:Adsorption Kinetics -N,N-dimethyl-1,3-propanediamine

The determination for adsorption kinetics was performed with a nominal test item concentration of 6.00 mg/L at a soil / solution ratio of 1:100. This concentration was selected with regard to the LOQ of the analytical method. Results are shown in the table below. Samples were agitated for 24 h and samples of the aqueous phase were measured at defined sampling points and the percentage of adsorption is given at adsorption equilibrium (LUFA 2.2 after 6 h, LUFA 2.3 and 2.4 after 24 h). In addition, test item control samples were analysed after 24 h. N,N-dimethyl-1,3-propanediamine adsorbs strongly to the soils.

 

Time to Reach Adsorption Equilibrium, Measured Amounts in Aqueous Phase, Calculated Amount for Solid Matrices, Percent of Adsorption and Distribution Coefficients K_d and K_OC for N,N-dimethyl-1,3-propanediamine

Applied test item concentration: 6000 µg/L, n = 2
agitation time: 24 h

Soil type	msoil [g]	Vaq [mL]	teq [h]	m^adss [µg]	Kd [mL/g]	KOC [mL/g]	Adsorption [%]	Recovery Control [%]^1)
LUFA 2.2	0.923	100	6	341	143	9695	57	104
LUFA 2.3	0.961	100	24	398	205	49859	66	97
LUFA 2.4	0.904	100	24	494	515	29590	82	105

m_soil          = used amount of soil (dry weight)

V_aq            = used volume of aqueous phase

t_eq              = time to reach adsorption equilibrium

m^ads_s         = amount adsorbed to soil

1)               = recovery related to initially measured (0 h) concentration

Tier 3: Desorption Kinetics -N,N-dimethyl-1,3-propanediamine

The desorption behavior of the test item was determined after 24 h adsorption. The table below shows the desorption coefficient K_des. Since the desorption coefficient is higher than the adsorption coefficient K_d, the test item adsorption is assumed to be not completely reversible.

 

Time to Reach Desorption Equilibrium, Percent of Desorption and Desorption Coefficient K_des for N,N-dimethyl-1,3-propanediamine

Applied test item concentration: 6000 µg/L, n = 2

Soil Type	msoil [g]	Vaq [mL]	teq [h]	m^desaq(eq) [µg]	m^adss(eq) [µg]	Kdes [mL/g]	Desorption [%]
LUFA 2.2	0.923	100	6	85.0	341	326	25
LUFA 2.3	0.961	100	24	75.7	398	443	19
LUFA 2.4	0.904	100	24	54.7	494	889	11

m_soil          = used amount of soil (dry weight)

V_aq            = used volume of aqueous phase

t_eq            = time to reach desorption equilibrium

m^des_aq        = amount of test item measured in the aqueous phase after desorption step

(without entrained water)

m^ads_s          = amount of test item adsorbed to soil at equilibrium

 

Validity criteria fulfilled:

yes

Conclusions:

Valid study performed according to the guidelines under GLP conditions using slightly adapted conditions

Executive summary:

The adsorption / desorption behavior of the test item Benzenesulfonic acid, C10-13-alkyl derivs., compds with N,N-dimethyl-1, 3-propanediamine (batch no.2629-89-10) was investigated in three different soils according to OECD guideline 106 and EC C.18. Distribution coefficients K_d and organic carbon normalized distribution coefficients K_OC were determined with a single concentration and the desorption behavior / reversibility of the adsorption from the soils was investigated. The test item consists of two components, C10-C13 alkylbenzene sulfonic acid(anionic component) and N,N-dimethyl-1,3-propanediamine(cationic component). Partitioning of both components was evaluated during this study.

 

For the anionic component, C10-C13 alkylbenzene sulfonic acid, three analytes were detected. Experiments have been conducted in LUFA soils 2.2, 2.3 and 2.4 with soil / solution ratios 1:5 and 1:30 as the adsorption is dependent on the soil type and the alkyl chain-length and increases with increasing chain-length. A concentration of 5.00 mg/L was used and the endpoints were calculated after 48 h agitation (time to reach equilibrium). The table below shows the determined distribution coefficients K_d and the corresponding organic carbon normalized distribution coefficients K_OC. Furthermore, the mobility of the test item in the investigated matrices was classified according to McCall et al.(1980) and the desorption coefficient K_des is presented in the summarizing table. The adsorption was determined to be not completely reversible.

 

Summarized Endpoints-C10-C13 alkylbenzene sulfonic acid

Mobility according to McCall et al.(1980): K_OC 0 – 50 very high, K_OC 50 – 150 high, K_OC 150 – 500 medium, K_OC 500 – 2000 low, K_OC 2000 – 5000 slight, K_OC > 5000 immobile

Soil type	Soil / solution ratio	Kd[mL/g]	KOC[mL/g]	Kdes[mL/g]	Mobility according to McCall et al.
	C10-alkylbenzene sulfonic acid
LUFA 2.2	1:5	65	4407	211	slight
LUFA 2.3	1:5	6	1462	33	low
LUFA 2.4	1:5	179	10278	194	immobile
	C11-alkylbenzene sulfonic acid
LUFA 2.2	1:5	175	11915	187	immobile
LUFA 2.3	1:5	13	3138	51	slight
LUFA 2.4	1:30	85	4862	984	slight
	C12-alkylbenzene sulfonic acid
LUFA 2.2	1:30	93	6298	939	immobile
LUFA 2.3	1:5	27	6627	79	immobile
LUFA 2.4	1:30	193	11087	1034	immobile

For the anionic compound, because MS is used for quantification the sorption of the three main constituent (C10, 11 and 12) on these soils were measured. The sorption of the three constituents on these three soils are presented in the table above and the mean of the sorption on the three soils is used for risk assessment. To be able to calculate the mean information on the content of the three constituents is needed.

The content of C10 in the anionic product is 20.8%

The content of C11 in the anionic product is 42.8%

The content of C12 in the anionic product is 29.9%

 

Mean Koc = ((0.208*4407 + 0.428*11915 + 0.299*6298) + (0.208*1462 + 0.428*3138 + 0.299*6627) + (0.208*10278 + 0.428*4862 + 0.299*11087))/3

Mean Koc = ((7899.378) + (3628.633) + (7533.773))/3 = 6353.9 L/kg

 

Thus for the anionic compound of the salt, the mean Koc is 6353.9 L/kg

The cationic component N,N-dimethyl-1,3-propanediamine showed strong adsorption to the soils. All experiments were conducted with a nominal concentration of 6.00 mg/L with agitation for 24 h and a soil / solution ratio of 1:100. N,N-dimethyl-1,3-propanediamine is immobile in all tested soils with irreversible adsorption.The table below shows the determined distribution coefficients K_d and the correspondingorganic carbon normalized distribution coefficients K_OC. Furthermore, the mobility of the test item in the investigated matrices was classified according to McCall et al.(1980) and the desorption coefficient K_des is shown.

Summarized Endpoints -N,N-dimethyl-1,3-propanediamine

Mobility according to McCall et al.(1980): K_OC 0 – 50 very high, K_OC 50 – 150 high, K_OC 150 – 500 medium, K_OC 500 – 2000 low, K_OC 2000 – 5000 slight, K_OC > 5000 immobile

Soil type	Soil / solution ratio	t (eq) [h]	Kd [mL/g]	KOC [mL/g]	Kdes[mL/g]	Mobility according to McCallet al.
	N,N-dimethyl-1,3-propanediamine
LUFA 2.2	1:100	6	143	9695	326	immobile
LUFA 2.3	1:100	24	205	49859	443	immobile
LUFA 2.4	1:100	24	515	29590	889	immobile

t_eq           = time to reach adsorption equilibrium

For the cationic compound, the mean Kd is 287.7 L/kg (mean of 143, 205 and 515 L/Kg). For the cationic product the Koc will not be used.

For the cationic product the normalization of the sorption constant to the organic carbon content of the soil is considered wrong. Instead of the Koc the Kd will be used as ethylene diamine will only sorb based on ionic interaction and not via hydrophobic interaction with the organic matter fraction in the soils.

In risk assessment Kd’s can as easily be used as the Koc.

Description of key information

In the sorption/desorption study the sorption of Benzenesulfonic acid, C10-13-alkyl derivs., compds with N,N-dimethyl-1, 3-propanediamine to three soils has been evaluated; Lufa 2.2, 2.3 and 2.4. The test substance is a salt which consists of an anionic (Benzenesulfonic acid, C10 -13 -alkyl derivs) and a cationic part (N,N-dimethyl-1, 3-propanediamine).

The anionic part consists of different constituents where the C10, 11 and 12 are the main constituents.

 

For the anionic compound, because MS is used for quantification the sorption of the three main constituent (C10, 11 and 12) on these soils were measured. The sorption of the three constituents on these three soils are presented table 1 and the mean of the sorption on the three soils is used for risk assessment. To be able to calculate the mean information on the content of the three constituents is needed.

The content of C10 in the anionic product is 20.8%

The content of C11 in the anionic product is 42.8%

The content of C12 in the anionic product is 29.9%

 

Mean Koc = ((0.208*4407 + 0.428*11915 + 0.299*6298) + (0.208*1462 + 0.428*3138 + 0.299*6627) + (0.208*10278 + 0.428*4862 + 0.299*11087))/3

Mean Koc = ((7899.378) + (3628.633) + (7533.773))/3 = 6353.9 L/kg

 

Thus for the anionic compound of the salt, the mean Koc is 6353.9 L/kg

 

For the cationic compound, the mean Kd is 287.7 L/kg (mean of 143, 205 and 515 L/Kg). For the cationic product the Koc will not be used.

For the cationic product the normalization of the sorption constant to the organic carbon content of the soil is considered wrong. Instead of the Koc the Kd will be used as ethylene diamine will only sorb based on ionic interaction and not via hydrophobic interaction with the organic matter fraction in the soils.

In risk assessment Kd’s can as easily be used as the Koc.

Key value for chemical safety assessment

Koc at 20 °C:

6 353.9

Other adsorption coefficients

Type:

other: Kd of the cationic part of the salt

Value in L/kg:

287.7

at the temperature of:

20 °C

Additional information

The adsorption / desorption behavior of the test item Benzenesulfonic acid, C10-13-alkyl derivs., compds with N,N-dimethyl-1, 3-propanediamine was investigatedin three different soils according to OECD guideline 106 and EC C.18. Distribution coefficients K_d and organic carbon normalized distribution coefficients K_OC were determined with a single concentration and the desorption behavior / reversibility of the adsorption from the soils was investigated. The test item consists of two components, C10-C13 alkylbenzene sulfonic acid(anionic component) and N,N-dimethyl-1,3-propanediamine (cationic component). Partitioning of both components in the presence of each other was evaluated during this study.

 

For the anionic component, C10-C13 alkylbenzene sulfonic acid, three analytes were detected. Experiments have been conducted in LUFA soils 2.2, 2.3 and 2.4 with soil / solution ratios 1:5 and 1:30 as the adsorption is dependent on the soil type and the alkyl chain-length and increases with increasing chain-length. A concentration of 5.00 mg/L was used and the endpoints were calculated after 48 h agitation (time to reach equilibrium). The table below shows the determined distribution coefficients K_d and the corresponding organic carbon normalized distribution coefficients K_OC. Furthermore, the mobility of the test item in the investigated matrices was classified according to McCallet al.(1980) and the desorption coefficient K_des is presented in the summarizing table. The adsorption was determined to be not completely reversible.

Summarized Endpoints-C10-C13 alkylbenzene sulfonic acid

Mobility according to McCallet al.(1980): K_OC 0 – 50 very high, K_OC 50 – 150 high, K_OC 150 – 500 medium, K_OC 500 – 2000 low, K_OC 2000 – 5000 slight, K_OC > 5000 immobile

Soil type	Soil / solution ratio	Kd[mL/g]	KOC[mL/g]	Kdes[mL/g]	Mobility according to McCallet al.
	C10-alkylbenzene sulfonic acid
LUFA 2.2	1:5	65	4407	211	slight
LUFA 2.3	1:5	6	1462	33	low
LUFA 2.4	1:5	179	10278	194	immobile
	C11-alkylbenzene sulfonic acid
LUFA 2.2	1:5	175	11915	187	immobile
LUFA 2.3	1:5	13	3138	51	slight
LUFA 2.4	1:30	85	4862	984	slight
	C12-alkylbenzene sulfonic acid
LUFA 2.2	1:30	93	6298	939	immobile
LUFA 2.3	1:5	27	6627	79	immobile
LUFA 2.4	1:30	193	11087	1034	immobile

For the anionic compound, because MS is used for quantification the sorption of the three main constituent (C10, 11 and 12) on these soils were measured. The sorption of the three constituents on these three soils are presented in the table above and the mean of the sorption on the three soils is used for risk assessment. To be able to calculate the mean, information on the content of the three constituents is needed.

The content of C10 in the anionic product is 20.8%

The content of C11 in the anionic product is 42.8%

The content of C12 in the anionic product is 29.9%

 

Mean Koc = ((0.208*4407 + 0.428*11915 + 0.299*6298) + (0.208*1462 + 0.428*3138 + 0.299*6627) + (0.208*10278 + 0.428*4862 + 0.299*11087))/3

Mean Koc = ((7899.378) + (3628.633) + (7533.773))/3 = 6353.9 L/kg

 

Thus for the anionic compound of the salt, the mean Koc is 6353.9 L/kg

The cationic component N,N-dimethyl-1,3 -propanediamine showed strong adsorption to the soils. All experiments were conducted with a nominal concentration of 6.00 mg/L with agitation for 24 h and a soil / solution ratio of 1:100. N,N-dimethyl-1,3-propanediamine is immobile in all tested soils with irreversible adsorption. The table below shows the determined distribution coefficients K_d and the corresponding organic carbon normalized distribution coefficients K_OC. Furthermore, the mobility of the test item in the investigated matrices was classified according to McCallet al.(1980) and the desorption coefficient K_des is shown.

Summarized Endpoints -N,N-dimethyl-1,3-propanediamine

Mobility according to McCallet al.(1980):K_OC 0 – 50 very high, K_OC 50 – 150 high, K_OC 150 – 500 medium, K_OC 500 – 2000 low, K_OC 2000 – 5000 slight, K_OC > 5000 immobile

Soil type	Soil / solution ratio	t (eq) [h]	Kd [mL/g]	KOC [mL/g]	Kdes[mL/g]	Mobility according to McCallet al.
	N,N-dimethyl-1,3-propanediamine
LUFA 2.2	1:100	6	143	9695	326	immobile
LUFA 2.3	1:100	24	205	49859	443	immobile
LUFA 2.4	1:100	24	515	29590	889	immobile

t_eq           = time to reach adsorption equilibrium

For the cationic compound, the mean Kd is 287.7 L/kg (mean of 143, 205 and 515 L/Kg). For the cationic product the Koc will not be used.

For the cationic product the normalization of the sorption constant to the organic carbon content of the soil is considered wrong. Instead of the Koc the Kd will be used as ethylene diamine will only sorb based on ionic interaction and not via hydrophobic interaction with the organic matter fraction in the soils.

In risk assessment Kd’s can as easily be used as the Koc.

[LogKoc: 3.803]