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Adsorption / desorption

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Reference
Endpoint:
adsorption / desorption
Remarks:
adsorption
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
weight of evidence
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
accepted calculation method
Justification for type of information:
Data is from computational model developed by USEPA
Reference:
Composition 0
Qualifier:
according to
Guideline:
other: Modeling database
Principles of method if other than guideline:
Prediction done using KOCWIN Program (v2.00)
GLP compliance:
not specified
Type of method:
other: MCI Method
Media:
soil
Test material information:
Composition 1
Specific details on test material used for the study:
- Name of test material (IUPAC name): 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid
- Molecular formula: C17H14N2O8S2
- Molecular weight: 438.4356 g/mol
- Smiles notation: c1cc(cc(c1)N)C(=O)Nc2ccc(c3c2c(cc(c3)S(=O)(=O)O)O)S(=O)(=O)O
-InChl:1S/C17H14N2O8S2/c18-10-3-1-2-9(6-10)17(21)19-13-4-5-15(29(25,26)27)12-7-11(28(22,23)24)8-14(20)16(12)13/h1-8,20H,18H2,(H,19,21)(H,22,23,24)(H,25,26,27)
- Substance type: Organic
Radiolabelling:
not specified
Test temperature:
25 deg.C
Analytical monitoring:
not specified
Key result
Type:
Koc
Value:
2 231 L/kg
Temp.:
25 °C
Remarks on result:
other: Log Koc= 3.3484 (estimated by MCI method)
Transformation products:
not specified

KOCWIN Program (v2.00) Results:

==============================

SMILES : c1cc(cc(c1)N)C(=O)Nc2ccc(c3c2c(cc(c3)S(=O)(=O)O)O)S(=O)(=O)O

CHEM : 1,4-Benzenediamine, 2-chloro-, sulfate

MOL FOR: C17 H14 N2 O8 S2

Koc may be sensitive to pH!

--------------------------- KOCWIN v2.00 Results ---------------------------

Koc Estimate from MCI:

---------------------

First Order Molecular Connectivity Index ........... : 13.375

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 7.5722

Fragment Correction(s):

1 Nitrogen to non-fused aromatic ring ... : -0.5225

1 Misc (C=O) Group (aliphatic attach).... : -1.6047

1 Sulfonic acid (-S(=O)-OH) ............. : -2.0000

1 Aromatic Hydroxy (aromatic-OH) ....... : -0.0966

Corrected Log Koc .................................. : 3.3484

Estimated Koc: 2231 L/kg <===========

Validity criteria fulfilled:
not specified
Conclusions:
The Soil Adsorption Coefficient i.e. Koc value of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) was estimated using EPI suite KOCWIN Program (v2.00) as 2231 L/kg (log Koc= 3.3484) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid has moderate sorption to soil and therefore have slow migration potential to ground water.
Executive summary:

The Soil Adsorption Coefficient i.e. Koc value of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) was estimated using EPI suite KOCWIN Program (v2.00) as 2231 L/kg (log Koc= 3.3484) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid has moderate sorption to soil and therefore have slow migration potential to ground water.

Description of key information

The Soil Adsorption Coefficient i.e. Koc value of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) was estimated using EPI suite KOCWIN Program (v2.00) as 2231 L/kg (log Koc= 3.3484) by means of MCI method at 25 deg. C. This log Koc value indicates that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid has moderate sorption to soil and therefore have slow migration potential to ground water.

Key value for chemical safety assessment

Koc at 20 °C:
2 231

Additional information

One predicted data study of target chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) and two experimental studies of its structurally similar red across chemical are summarized below for Adsorption endpoint.

 

In predicted data study the Soil Adsorption Coefficient i.e. Koc value of test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) was estimated using Estimation Program Interface (EPI suite, 2017) KOCWIN Program (v2.00) as 2231 L/kg (log Koc= 3.3484) by means of MCI method at 25 deg. C.

 

Next weight of evidence study was experimental study done for read across chemical from journal of J. Environ. Eng. Manage., 17(1), 29-38 (2007) in this study the adsorption of Acid Red 1 on organoclay is dominated by ion exchange process. The Freundlich and Langmuir adsorption isotherm constants of Acid Red 1 on organoclay are as follows: Acid Red 1 adsorption on organoclay the coefficients for fitting are 0.995 < rL2 < 0.997 and 0.573 < rF2 < 0.751. It can be seen that the Langmuir model yields a much better fit than the Freundlich model when the r2 values are compared. The affinity parameter, KL, and its reciprocal indicate that the adsorption capacity of Acid Red 1 on organoclay is highly perceptible to changes in temperature. The Q max values indicate that Acid Red 1 possesses higher adsorption capacity at lower temperature.

 

Last weight of evidence study was also experimental study done for another read across chemical disodium 5-amino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate (CAS No. 3567-66-6) from UERL laboratory (2016) in this study the adsorption coefficient Koc in soil and in sewage sludge disodium 5-amino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate (CAS No. 3567-66-6) was determined by the Reverse Phase High Performance Liquid Chromatographic method. The reference substances were chosen according to estimated Koc range of the test substance and generalized calibration graph was prepared. The reference substances were Phenol, Aniline, Nitrobenzene, naphthalene, Phenanthrene and DDT were chosen having Koc value ranging from 1.32 to 5.63. The Log Koc value of read across chemical disodium 5-amino-4-hydroxy-3-(phenylazo)naphthalene-2,7-disulphonate was determined to be 3.679 dimensionless at 25°C. Based on the value of log Koc it is concluded that this read across chemical has strong sorption to soil and sediments and therefore has slow migration potential to ground water.

On the basis of all the study mentioned above it is concluded that test chemical 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-1,7-disulphonic acid (CAS No. 70239-77-9) has moderate to strong sorption to soil and sediment therefore it has slow migration potential to ground water.

[LogKoc: 3.3484]