1,2-Ethanediamine, N-{3-(trimethoxysilyl)propyl}-,N-{(ethenylphenyl)methyl}derivate,hydrochlorides

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption, other

Remarks:

adsorption

Type of information:

(Q)SAR

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model, but not (completely) falling into its applicability domain, with adequate and reliable documentation / justification

Remarks:

The substance is not fully compliant with the applicability domain of the model. However, this calculation is used in a weight of evidence approach, in accordance to the REACh Regulation (EC) No 1907/2006, Annex XI General rules for adaptation of the standard testing regime set out in Annexes VII to X, 1.2. It is adequately documented and justified: the prediction is evaluated on the basis of the model performance on similar substances. For more details see section `overall remarks, attachments´.

Justification for type of information:

1. SOFTWARE
ChemProp(TM) Main Module 6.6, Public OSIRIS Edition

2. MODEL (incl. version number)
Franco, Fu & Trapp (Partitioning, soil sorption coefficient, Koc), ionizable substances, acids and bases

3. SMILES OR OTHER IDENTIFIERS USED AS INPUT FOR THE MODEL
See “Test material information”

4. SCIENTIFIC VALIDITY OF THE (Q)SAR MODEL
See attached information on the model provided by the developer. Further information on the OECD criteria as outlined by the applicant is provided below under "Any other information of materials and methods incl. tables"

5. APPLICABILITY DOMAIN
See attached information and information as provided in "Any other information on results incl. tables".

6. ADEQUACY OF THE RESULT
See assessment of adequacy as outlined in the "Overall remarks, attachments" section.

Qualifier:

according to guideline

Version / remarks:

REACH Guidance on QSARs R.6

Principles of method if other than guideline:

- Software tool(s) used including version: ChemProp v6.6
- Model(s) used: Franco, Fu & Trapp
Full reference and details of the used formulas can be found in:
1. Franco A, Fu W, Trapp S 2009. Influence of soil pH on the sorption of ionizable chemicals: Modeling advances. Environ. Toxicol. Chem. 28: 458-464.
2. Franco A, Trapp S 2008. Estimation of the soil-water partition coefficient normalized to organic carbon for ionizable organic chemicals. Environ. Toxicol. Chem. 27: 1995-2004.
- Model description: see field 'attached justification' and 'any other information on material and methods'
- Justification of QSAR prediction: see field 'Justification for type of information', 'Attached justification' and/or 'overall remarks'

GLP compliance:

no

Type of method:

other: calculation

Media:

soil

Details on test conditions:

BASIS FOR CALCULATION OF Koc:
- Estimation software: ChemProp v6.5, Franco and Trapp 2008 model for bases

- Log Kow used:
N-[3-(trihydroxysilyl)propyl]ethylenediamine monohydrochloride: -5.3
(2-aminoethyl)[(4 -vinylphenyl)methyl][3 -(trihydroxysilyl)propyl] amine hydrochloride: -2.06
N-[3-(trihydroxysilyl)propyl]-N'-(4 -vinylbenzyl)-1,2-ethanediamine hydrochloride: -2.14
N-[3-(trihydroxysilyl)propyl]-N,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride: 1.01
N-[3-(trihydroxysilyl)propyl]-N’,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride: 0.68
N-[3-(trihydroxysilyl)propyl]-N,N’,N'-tri(vinylbenzyl)-1,2- ethanediamine hydrochloride: 3.83

- pKa used:
N-[3-(trihydroxysilyl)propyl]ethylenediamine monohydrochloride:
(2-aminoethyl)[(4 -vinylphenyl)methyl][3 -(trihydroxysilyl)propyl] amine hydrochloride:
N-[3-(trihydroxysilyl)propyl]-N'-(4 -vinylbenzyl)-1,2-ethanediamine hydrochloride:
N-[3-(trihydroxysilyl)propyl]-N,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride:
N-[3-(trihydroxysilyl)propyl]-N’,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride:
N-[3-(trihydroxysilyl)propyl]-N,N’,N'-tri(vinylbenzyl)-1,2- ethanediamine hydrochloride:

- pH: 4, 5.8, 7, 9

Type:

log Koc

Value:

0.235 dimensionless

pH:

4

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]ethylenediamine monohydrochloride

Type:

log Koc

Value:

0.5 dimensionless

pH:

4.5

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]ethylenediamine monohydrochloride

Type:

log Koc

Value:

0.465 dimensionless

pH:

7

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]ethylenediamine monohydrochloride

Type:

log Koc

Value:

0.004 dimensionless

pH:

9

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]ethylenediamine monohydrochloride

Type:

log Koc

Value:

0.745 dimensionless

pH:

4

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

(2-aminoethyl)[(4 -vinylphenyl)methyl][3 -(trihydroxysilyl)propyl] amine hydrochloride

Type:

log Koc

Value:

1.67 dimensionless

pH:

4.5

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

(2-aminoethyl)[(4 -vinylphenyl)methyl][3 -(trihydroxysilyl)propyl] amine hydrochloride

Type:

log Koc

Value:

1.369 dimensionless

pH:

7

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

(2-aminoethyl)[(4 -vinylphenyl)methyl][3 -(trihydroxysilyl)propyl] amine hydrochloride

Type:

log Koc

Value:

0.954 dimensionless

pH:

9

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

(2-aminoethyl)[(4 -vinylphenyl)methyl][3 -(trihydroxysilyl)propyl] amine hydrochloride

Type:

log Koc

Value:

0.779 dimensionless

pH:

4

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N'-(4 -vinylbenzyl)-1,2-ethanediamine hydrochloride

Type:

log Koc

Value:

1.62 dimensionless

pH:

4.5

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N'-(4 -vinylbenzyl)-1,2-ethanediamine hydrochloride

Type:

log Koc

Value:

1.181 dimensionless

pH:

7

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N'-(4 -vinylbenzyl)-1,2-ethanediamine hydrochloride

Type:

log Koc

Value:

0.914 dimensionless

pH:

9

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N'-(4 -vinylbenzyl)-1,2-ethanediamine hydrochloride

Type:

log Koc

Value:

2.321 dimensionless

pH:

4

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

3.13 dimensionless

pH:

4.5

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

2.347 dimensionless

pH:

7

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

2.078 dimensionless

pH:

9

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

2.392 dimensionless

pH:

4

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N’,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

2.61 dimensionless

pH:

4.5

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N’,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

1.968 dimensionless

pH:

7

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N’,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

1.952 dimensionless

pH:

9

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N’,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

2.82 dimensionless

pH:

4

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N,N’,N'-tri(vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

2.93 dimensionless

pH:

4.5

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N,N’,N'-tri(vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

3.116 dimensionless

pH:

7

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N,N’,N'-tri(vinylbenzyl)-1,2- ethanediamine hydrochloride

Type:

log Koc

Value:

3.117 dimensionless

pH:

9

% Org. carbon:

5

Remarks on result:

other: based on eq. 1 (bases)

Remarks:

N-[3-(trihydroxysilyl)propyl]-N,N’,N'-tri(vinylbenzyl)-1,2- ethanediamine hydrochloride

Table 1: Input parameters log Kow, pKa and pH and resulted Koc/log Koc values for the hydrolysis products of each constituent of the substance.

			Koc log Koc at pH:
Constituent	log Kow	pka	4	4.50	7	9
N-[3-(trihydroxysilyl)propyl]ethylenediamine monohydrochloride	-5.3	8.05	1.720 0.235	3.162 0.5	2.917 0.465	0.99 -0.004
(2-aminoethyl)[(4 -vinylphenyl)methyl][3 -(trihydroxysilyl)propyl] amine hydrochloride	-2.06	6.8	5.554 0.745	46.774 1.67	23.402 1.369	8.994 0.954
N-[3-(trihydroxysilyl)propyl]-N'-(4 -vinylbenzyl)-1,2-ethanediamine hydrochloride	-2.14	6.42	6.009 0.779	41.687 1.62	15.184 1.181	8.198 0.914
N-[3-(trihydroxysilyl)propyl]-N,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride:	1.01	5.95	209.58 2.321	1348.963 3.13	222.431 2.347	119.636 2.078
N-[3-(trihydroxysilyl)propyl]-N’,N'-di(4-vinylbenzyl)-1,2- ethanediamine hydrochloride	0.68	4.89	246.43 2.392	407.380 2.61	92.918 1.968	89.489 1.952
N-[3-(trihydroxysilyl)propyl]-N,N’,N'-tri(vinylbenzyl)-1,2- ethanediamine hydrochloride	3.83	4.62	661.10 2.820	891.138 2.93	1306.147 3.116	1309.450 3.117

For detailed information on the results please refer to the attached report.

Validity criteria fulfilled:

not applicable

Description of key information

1,2-Ethanediamine, N-{3-(trihydroxysilyl)propyl}-,N-{(ethenylphenyl)methyl}derivate, hydrochlorides: log Koc: 0.465 - 3.116 at pH 7

Key value for chemical safety assessment

Koc at 20 °C:

2.917

Additional information

1,2-Ethanediamine, N-{3-(trimethoxysilyl)propyl}-,N-{(ethenylphenyl)methyl}derivate, hydrochlorides (CAS 171869-89-9) hydrolyses in contact with water to the corresponding hydrolysis products 1,2-Ethanediamine, N-{3-(trihydroxysilyl)propyl}-,N-{(ethenylphenyl)methyl}derivate, hydrochlorides and methanol. 

Since all constituents of the substance are hydrolytically unstable further information on the adsorption behavior of the hydrolysis products was collected by an appropriate calculation method. Considering the ionizing properties of the compounds, the adsorption potential has been calculated using Franco and Trapp ‘s expressions (2008) on estimation of the organic carbon-water partitioning coefficient of ionisable organic substances. The model is incorporated in the ChemProp v6.6 software. The log Koc was calculated for the hydrolysis products of all constituents of the substance for pH 4, 4.5, 7 and 9. The log Koc for pH 4.5 was retrieved using the pH dependent soil sorption coefficient model for bases incorporated in the ChemProp software. The log Koc for 4, 7 and 9 was calculated manually with the equation given by the ChemProp model for bases (based on Franco & Trapp, 2008) since the software does not consider other pH than 4.5.

The following equation was used for Koc calculation as suggested by the authors:

Koc =Φn x 10^{0.37xlogPn+1.70}+Φion x 10^{pKa^0.65xf^0.14}

Where:

Φn = 1/(1+10^(pH-pKa))

Pn: Kow of the neutral molecule (EpiWin)

pKa: 4.62 – 8.05 depending on the constituent (calculated with SPARC v4.6)

Φion = 1- Φn

f: Ratio of concentration in octanol to total concentration: Kow (overall)/(Kow (overall) + 1)

 

Based on these calculations the log Koc values of the hydrolysis products range between 0.235 - 2.820 at pH 4; 0.5 and 2.93 at pH 4.5; 0.465 and 3.116 at pH 7 as well as -0.004 and 3.117 at pH 9. These values indicate the low to moderate adsorption potential of the incurred substances in soils and sediments.

According to the Guidance on Information Requirements and Chemical Safety Assessment, Chapter R.7.1.8.5 the log Pn value for the ionized molecule determined around the default pH of 7 is considered more relevant for chemical safety assessment. Therefore the log Koc values calculated for pH 7 were considered as key values for the calculation of PNECs. The Koc value for which the lowest PNEC was derived (worst case scenario for soil/sediment microorganisms) was used as key Koc value (Koc of 2.917).