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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 1
Qualifier:
according to
Guideline:
other: Modeling database
Principles of method if other than guideline:
KOCWIN Program (v2.00)
GLP compliance:
not specified
Type of method:
other: estimation
Media:
soil
Test material information:
Composition 1
Specific details on test material used for the study:
- Name ( regulatory process): 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate

- Name of test material (as cited in study report): Acetamide, N- 3- bis 2-(acetyloxy)ethyl amino phenyl

- Molecular formula : C16H22N2O5

- Molecular weight : 322.359 g/mole

- Smiles notation : O=C(OCCN(c1cccc(NC(=O)C)c1)CCOC(=O)C)C
- InChl: 1S/C16H22N2O5/c1-12(19)17-15-5-4-6-16(11-15)18(7-9-22-13(2)20)8-10-23-14(3)21/h4-6,11H,7-10H2,1-3H3,(H,17,19)

- Substance type: Organic
-Physical state: white to off white coloured powder
Radiolabelling:
not specified
Test temperature:
25 deg C
Analytical monitoring:
not specified
Type:
Koc
Value:
15.11 L/kg
Temp.:
25 °C
Remarks on result:
other: Estimated via MCI method log Koc= 1.179
Transformation products:
not specified

KOCWIN Program (v2.00) Results:

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

SMILES : O=C(OCCN(c(cccc1NC(=O)C)c1)CCOC(=O)C)C

CHEM : Acetamide, N- 3- bis 2-(acetyloxy)ethyl amino phenyl -

MOL FOR: C16 H22 N2 O5

MOL WT : 322.36

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

Koc Estimate from MCI:

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

First Order Molecular Connectivity Index ........... : 10.880

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 6.2715

Fragment Correction(s):

2 Nitrogen to non-fused aromatic ring ... : -1.0450

1 N-CO-C (aliphatic carbon) ............ : -1.0277

2 Nitrogen to Carbon (aliphatic) (-N-C).. : -0.4255

2 Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -2.5939

Corrected Log Koc .................................. : 1.1794

Estimated Koc: 15.11 L/kg <===========

Validity criteria fulfilled:
not specified
Conclusions:
The Soil Adsorption Coefficient i.e Koc value of 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (CAS No: 27059-08-1) was estimated using EPI suite KOCWIN Program (v2.00) program as Koc 15.11 L/kg (log Koc=1.179) by means of MCI method at 25 deg.C. This Koc value indicates that the substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate has a negligible sorption to soil and sediment and therefore have rapid migration potential to groundwater.
Executive summary:

The Soil Adsorption Coefficient i.e Koc value of 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (CAS No: 27059-08-1) was estimated using EPI suite KOCWIN Program (v2.00) program as Koc 15.11 L/kg (log Koc=1.179)  by means of MCI method at 25 deg.C. This Koc value indicates that the substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate has a negligible sorption to soil and sediment and therefore have rapid migration potential to groundwater.

Description of key information

The Soil Adsorption Coefficient i.e Koc value of 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (CAS No: 27059-08-1) was estimated using EPI suite KOCWIN Program (v2.00) program as Koc 15.11 L/kg (log Koc=1.179)  by means of MCI method at 25 deg.C. This Koc value indicates that the substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate  has a negligible sorption to soil and sediment and therefore have rapid migration potential to groundwater.

Key value for chemical safety assessment

Koc at 20 °C:
15.11
Log Koc at 20 °C:
1.179

Additional information

Many studies have been carried out to predict to Adsorption coefficient i.e., Koc Value of target chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (CAS No: 27059-08-1) the results of different prediction studies are summarized below.

 

The Soil Adsorption Coefficient i.e Koc value of 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (CAS No: 27059-08-1) was estimated using Estimation programe interface (EPI suite, 2017) KOCWIN Program (v2.00) as Koc 15.11 L/kg (log Koc=1.179)  by means of MCI method at 25 deg.C. This Koc value indicates that the substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate  has a negligible sorption to soil and sediment and therefore have rapid migration potential to groundwater.

 

Another prediction study done using (ACD (Advanced Chemistry Development)/I-Lab predictive module, 2017) by Adsorption Coefficient module (v12.1.0.50374) program.The Soil Adsorption Coefficient i.e Koc value of test substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate  was estimated  at different pH as Koc 1 dimensionless (log Koc= 0) at pH range 1-2, Koc 4.66 dimensionless( log koc=0.7) at pH 3, Koc range from 32.1 to 104 dimensionless( log koc range=1.5-2.0) at pH 4 -14. By considering log Koc values at pH 6, 7 and 8 indicate that the 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate has a low sorption to soil and sediment and therefore have moderate to low migration potential to groundwater.

 

Next study was done by using Sci Finder database ( American chemical society (ACS) 2017). Soil Adsorption coeeficient was estimated for the test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -17 -3) was in range 1-7.70 ( log koc range =0-0.88) at pH 1 -3 and temperature 25 oC  and  at pH 4-14 Koc value range from 53.0-179 ( log Koc range= 1.72-2.25)  and temperature 25 °C. These Koc values at pH 6, 7 and 8 and temperature 25 °C indicate that the test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate has low sorption to soil and sediment and therefore have moderate migration potential to groundwater.

 

Another prediction done by using the Chemspider - ACD/PhysChem Suite 2017.Soil Adsorption/Mobility study was conducted for the test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (CAS No: 27059-08-1) to estimate its Koc value at pH 5.5 and pH 7.4. The adsorption coefficient i.e Koc value of test substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate at pH 5.5 was estimated to be 120.33 ( log koc=2.080) and pH 7.4 was estimated to be 129.35 (log koc=2.111).These Koc value at pH 5.5 and pH 7.4 indicates that the test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate as low sorption to soil and sediment and therefore have moderate migration potential to groundwater.

 

One more prediction done from CompTox Chemistry Dashboard using OPERA (OPEn (quantitative) structure-activity Relationship Application)  V1.02 model in which calculation based on PaDEL descriptors (calculate molecular descriptors and fingerprints of chemical)  the adsorption coefficient i.e KOC for test substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (CAS no.27059 -08 -1) was estimated to be 248 L/kg (log Koc = 2.394) .The predicted KOC result based on the 5 OECD principles. Thus based on the result it is concluded that the test substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate has a low sorption to soil and sediment and therefore have moderate migration potential to ground water.

 

On the basis of above studies overall results for target chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate (from EPI suite, ACD labs,SciFinder, ChemSpider database and CompTox Chemistry Dashboard,2017), it can be concluded that the Koc value of test substance 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ranges from 15.11 -179 ( log Koc= 1.17 -2.252) indicating that the test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate has a low sorption to soil and sediment and therefore have moderate migration potential to groundwater.