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Adsorption / desorption

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Endpoint:
adsorption / desorption: screening
Remarks:
adsorption
Type of information:
(Q)SAR
Adequacy of study:
key study
Study period:
2016
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Accepted calculation method.
Justification for type of information:
QSAR prediction: migrated from IUCLID 5.6
Guideline:
other: REACH guidance QSARs R6, May/July 2008
Principles of method if other than guideline:
Estimation Program Interface EPI-Suite version 4.1: KOCWIN (v2.00) for the estimation of the organic carbon-normalized sorption coefficient for soil and sediment (Koc).
The Estimation Program Interface was developed by the US Environmental Agency's Office of Pollution Prevention and Toxics, and Syracuse Research Corporation (SRC). © 2000 - 2011 U.S. Environmental Protection Agency for EPI SuiteTM (Published online in January 2011).
GLP compliance:
no
Type of method:
other: Estimation
Media:
soil
Radiolabelling:
no
Type:
log Koc
Value:
3.72
Remarks on result:
other: calculation (logKow method)
Type:
log Koc
Value:
4.623
Remarks on result:
other: calculation (MCI method)
Phase system:
other: Koc
Type:
other: Koc
Value:
5 245 L/kg
Remarks on result:
other: calculation (logKow method)
Phase system:
other: Koc
Type:
other: Koc
Value:
42 010 L/kg
Remarks on result:
other: calculation (MCI method)

Validity of the model:

1. Defined Endpoint: Organic carbon partition coefficient, given as logarithmic Koc and Koc

2. Unambigous algorithm: The molecule is first classified as a polar substance. Based on structure of the molecule, the following fragments were applied: 2 Nitrogen to non-fused aromatic ring and 1 Nitrogen to Carbon (aliphatic). The number of times of the fragments that occurs in the structure of the substance applied by the program is verified. For estimation of logKoc according to the logKow method the estimated logKow of 5.17 as calculated by the program was used.

3. Applicable domain: With a molecular weight of 282.43 g/mol the substance is within the range of the training set (32 - 665 g/mole) as well as in the validation set (27 - 991 g/mole). Regarding the structure of N-(1,4-dimethylpentyl)-N'-phenylbenzene-1,4-diamine, the fragment descriptors found by the program are complete.

4a. Statistical characteristics (MCI method): N training set without corrections = 69; N training set with correction = 447; N validation set = 158; Correction coefficient of the total training set without corrections r² = 0.967; Correlation coefficient of the total training set with corrections r² = 0.900; Correlation coefficient of the total validation set r² = 0.850.

4b.Statistical characteristics (Kow method): N training set without corrections = 68; N training set with correction = 447; N validation set = 150; Correction coefficient of the total training set without corrections r² = 0.877; Correlation coefficient of the total training set with corrections r² = 0.855; Correlation coefficient of the total validation set r² = 0.778.

5. Mechanistic interpretation: Log Koc is estimated based on the likeliness of a substance for sorption to surfaces of soil/sediment particles. The log Koc is a physical inherent property used extensively to describe a chemical's likeliness to adsob to organic carbon.

Adequacy of prediction:

The result for N-(1,4-dimethylpentyl)-N'-phenylbenzene-1,4-diamine falls within the applicability domain described above and the estimation rules applied for the substance appears appropriate.

Validity criteria fulfilled:
not applicable
Conclusions:
The QSAR determination of the carbon partition coefficient for N-(1,4-dimethylpentyl)-N'-phenylbenzene-1,4-diamine using the model KOCWIN v2.00 included in the Estimation Program Interface (EPI) Suite v4.11 revealed values of 5245 L/kg (logKow method) and 42010 L/kg (MCI method) for the unaffected molecule of the substance as any decomposition (e.g. hydrolysis) of the substance is not taken into account by the program.
Executive summary:

The organic carbon partition coefficient (Koc) for N-(1,4-dimethylpentyl)-N'-phenylbenzene-1,4-diamine was predicted using the QSAR calculation of the Estimation Program Interface (EPI) Suite v 4.11. The Koc was estimated to be 5245 L/kg (logKow method), and 42010 L/kg (MCI method). The results relate to the unaffected molecule of the substance as any decomposition (e.g. hydrolysis) of the substance is not taken into account by the program.

Endpoint:
adsorption / desorption: screening
Remarks:
adsorption
Type of information:
(Q)SAR
Adequacy of study:
key study
Study period:
2016
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Accepted calculation method.
Justification for type of information:
QSAR prediction: migrated from IUCLID 5.6
Guideline:
other: REACH guidance QSARs R6, May/July 2008
Principles of method if other than guideline:
Estimation Program Interface EPI-Suite version 4.1: KOCWIN (v2.00) for the estimation of the organic carbon-normalized sorption coefficient for soil and sediment (Koc).
The Estimation Program Interface was developed by the US Environmental Agency's Office of Pollution Prevention and Toxics, and Syracuse Research Corporation (SRC). © 2000 - 2011 U.S. Environmental Protection Agency for EPI SuiteTM (Published online in January 2011).
GLP compliance:
no
Type of method:
other: Estimation
Media:
soil
Radiolabelling:
no
Type:
log Koc
Value:
2.61
Remarks on result:
other: calculation (logKow method)
Type:
log Koc
Value:
3
Remarks on result:
other: calculation (MCI method)
Phase system:
other: Koc
Type:
other: Koc
Value:
406 L/kg
Remarks on result:
other: calculation (logKow method)
Phase system:
other: Koc
Type:
other: Koc
Value:
1 061 L/kg
Remarks on result:
other: calculation (MCI method)

Validity of the model:

1. Defined Endpoint: Organic carbon partition coefficient, given as logarithmic Koc and Koc

2. Unambigous algorithm: The molecule is first classified as a polar substance. Based on structure of the molecule, the following fragments were applied: 2 Nitrogen to non-fused aromatic ring and 1 Aromatic Hydroxy (aromatic - OH). The number of times of the fragments that occurs in the structure of the substance applied by the program is verified. For estimation of logKoc according to the logKow method the estimated logKow of 2.46 as calculated by the program was used.

3. Applicable domain: With a molecular weight of 185.23 g/mol the substance is within the range of the training set (32 - 665 g/mole) as well as in the validation set (27 - 991 g/mole). Regarding the structure of N-(1,4-dimethylpentyl)-N'-phenylbenzene-1,4-diamine, the fragment descriptors found by the program are complete.

4a. Statistical characteristics (MCI method): N training set without corrections = 69; N training set with correction = 447; N validation set = 158; Correction coefficient of the total training set without corrections r² = 0.967; Correlation coefficient of the total training set with corrections r² = 0.900; Correlation coefficient of the total validation set r² = 0.850.

4b.Statistical characteristics (Kow method): N training set without corrections = 68; N training set with correction = 447; N validation set = 150; Correction coefficient of the total training set without corrections r² = 0.877; Correlation coefficient of the total training set with corrections r² = 0.855; Correlation coefficient of the total validation set r² = 0.778.

5. Mechanistic interpretation: Log Koc is estimated based on the likeliness of a substance for sorption to surfaces of soil/sediment particles. The log Koc is a physical inherent property used extensively to describe a chemical's likeliness to adsob to organic carbon.

Adequacy of prediction:

The result for 4 -Hydroxydiphenalamine falls within the applicability domain described above and the estimation rules applied for the substance appears appropriate.

Validity criteria fulfilled:
not applicable
Conclusions:
The QSAR determination of the carbon partition coefficient for 4 -Hydroxydiphenalamine using the model KOCWIN v2.00 included in the Estimation Program Interface (EPI) Suite v4.11 revealed values of 406 L/kg (logKow method) and 1061 L/kg (MCI method) for the unaffected molecule of the substance as any decomposition (e.g. hydrolysis) of the substance is not taken into account by the program.
Executive summary:

The organic carbon partition coefficient (Koc) for 4 -Hydroxydiphenalamine was predicted using QSAR calculation of the Estimation

Program Interface (EPI) Suite v 4.11. The Koc was estimated to be 406 L/kg (logKow method), and 1061 L/kg (MCI method). The results relate to the unaffected molecule of the substance as any decomposition (e.g. hydrolysis) of the substance is not taken into account by the program.

Description of key information

In accordance with column 2 of REACH Annex IX, the study does not need to be conducted as the substance is hydrolytically unstable, the half-life of 7PPD is 5.15 h.
However, the calculated low Koc values from 7PPD were used for the calculations of the PNECs for sediment and soil.

Key value for chemical safety assessment

Koc at 20 °C:
11 480

Additional information

N-(1,4-dimethylpentyl)-N'-phenylbenzene-1,4-diamine. For assessment, the value LogKoc = 4.06 was taken. It has to be taken into account, that the substance is hydrolytically unstable (half-life 5.15 h).

4-Hydroxydiphenylamine (CAS 122-37-2) was identified as the primary hydrolysis product. The Benzoquinoneimine-n-phenyl is the oxidized form of 4-hydroxydiphenylamine (Monsanto, 1986). The estimated LogKoc values for 4-hydroxydiphenylamine was 406 L/kg (logKow method), and 1061 L/kg(MCI method. (Currenta, 2016)

The physico-chemical properties of 4-hydroxydiphenylamine are different especially concerning the Koc value, it should be taken into account that this metabolite has a different behaviour in the environment.