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Reference
Endpoint:
adsorption / desorption: screening
Remarks:
adsorption
Type of information:
(Q)SAR
Adequacy of study:
key study
Study period:
2013
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification
Justification for type of information:
QSAR
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
Specific details on test material used for the study:
Values related to the pure substance.

'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' is a "multi constituent substance" consisting of benzyl 2-ethylhexyl adipate [CAS 58394-64-2], bis (2-ethylhexyl) adipate [CAS 103-23-1] and dibenzyl adipate [CAS 2451-84-5].
Calculations were performed for each constituent. For calculations based on the Log Kow method the corresponding log Kow was taken into account. The log Kow of each constituent is internally calculated by KOCWIN.

Constituent A:
Chemical name: benzyl 2-ethylhexyl adipate
SMILES: CCCCC(CC)COC(=O)CCCCC(=O)OCc1ccccc1
use descriptors applied in the model:
- molecular weight: 348.49 g/mole
- an estimated log Kow value of 6.46 was used

Constituent B:
Chemical name: bis (2-ethylhexyl) adipate
SMILES: O=C(OCC(CCCC)CC)CCCCC(=O)OCC(CCCC)CC
use descriptors applied in the model:
- molecular weight: 370.58 g/mole
- an estimated log Kow value of 8.12 was used

Constituent C:
Chemical name: dibenzyl adipate
SMILES: c1(COC(=O)CCCCC(=O)OCc2ccccc2)ccccc1
use descriptors applied in the model:
- molecular weight: 326.40 g/mole
- an estimated log Kow value of 4.80 was used
Radiolabelling:
no
Key result
Type:
log Koc
Value:
4.367 dimensionless
Remarks on result:
other: constituent A [benzyl 2-ethylhexyl adipate] (log Kow method)
Key result
Type:
log Koc
Value:
4.34 dimensionless
Remarks on result:
other: constituent A [benzyl 2-ethylhexyl adipate] (MCI method)
Key result
Type:
log Koc
Value:
5.285 dimensionless
Remarks on result:
other: constituent B [bis(2-ethylhexyl) adipate] (log Kow method)
Key result
Type:
log Koc
Value:
4.556 dimensionless
Remarks on result:
other: constituent B [bis(2-ethylhexyl) adipate] (MCI method)
Key result
Type:
log Koc
Value:
3.449 dimensionless
Remarks on result:
other: constituent C [dibenzyl adipate] (log Kow method)
Key result
Type:
log Koc
Value:
4.125 dimensionless
Remarks on result:
other: constituent C [dibenzyl adipate] (MCI method)
Phase system:
other: Koc
Type:
other: Koc
Value:
23 290 L/kg
Remarks on result:
other: constituent A [benzyl 2-ethylhexyl adipate] (log Kow method)
Phase system:
other: Koc
Type:
other: Koc
Value:
21 900 L/kg
Remarks on result:
other: constituent A [benzyl 2-ethylhexyl adipate] (MCI method)
Phase system:
other: Koc
Type:
other: Koc
Value:
192 900 L/kg
Remarks on result:
other: constituent B [bis(2-ethylhexyl) adipate] (log Kow method)
Phase system:
other: Koc
Type:
other: Koc
Value:
36 000 L/kg
Remarks on result:
other: constituent B [bis(2-ethylhexyl) adipate] (MCI method)
Phase system:
other: Koc
Type:
other: Koc
Value:
2 811 L/kg
Remarks on result:
other: constituent C [dibenzyl adipate] (log Kow method)
Phase system:
other: Koc
Type:
other: Koc
Value:
13 320 L/kg
Remarks on result:
other: constituent C [dibenzyl adipate] (MCI method)

'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' is a "multi constituent substance" consisting of benzyl 2-ethylhexyl adipate [CAS 58394-64-2], bis (2-ethylhexyl) adipate [CAS 103-23-1] and dibenzyl adipate [CAS 2451-84-5].

For each constituent of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' KOCWIN estimated the log Koc with two separate estimation methodologies. The estimations are based on the first-order Molecular Connectivity Index (MCI) and the log Kow (internally calculated by KOCWIN), respectively.

 

Validity of the model:

1. Defined Endpoint:

Organic carbon partition coefficient, given as logarithmic Koc and Koc

2. Unambigous algorithm:

Each constituent of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' is identified as a polar substance by the program.

Based on structure of the molecules, the following fragments were applied: 2 Ester (-C-CO-O-C-) or (HCO-O-C).

The number of times of the fragments that occurs in the structure of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' applied by the program is verified.

For estimation of log Koc according to the log Kow method the following internally calculated log Kow values were used:

constituent A [benzyl 2-ethylhexyl adipate]: log Kow 6.46

constituent B [bis(2-ethylhexyl) adipate]: log Kow 8.12

constituent C [dibenzyl adipate]: log Kow 4.80

3. Applicable domain:

With a molecular weights of 326.40 to 370.58 g/mole the constituents of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' are 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 all constituents, 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 (log 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: The 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.

6. Adequacy of prediction: The results for all constituents of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' falls within the applicability domain of the model and the applied estimating rules appear appropriate. Individual uncertainties for the investigated substances benzyl 2-ethylhexyl adipate and dibenzyl adipate are not available. Bis(2-ethylhexyl) adipate is located in the training dataset and listed in Appendix F (compounds Used for the Correction Fragment Regression).

Thus, the probability is high, that the structural fragments applied by the program for the substance of interest were appropriate.

For bis(2-ethylhexyl) adipate the residual, defined as the difference between the experimental log Koc value and the log Koc values predicted by the MCI- and log Kow-method, expressed as absolute value, is +0.37 for the MCI method, and +1.10 for the log Kow method.

The uncertainty can be stated due to the lack of information of the experimental study design, as the substance is poorly soluble in water. Further, the predicted log Kow for bis(2-ethylhexyl) adipate is 8.12. It is assumed that log Koc results predicted by the log Kow method are less accurate with increasing log Kow values, due to low level presence of compounds with higher log Kow values in the training set.

Regarding the predicted values for benzyl 2-ethylhexyl adipate and dibenzyl adipate it is considered that their uncertainty is in the same range as bis(2-ethylhexyl) adipate.

The prediction of organic carbon partition coefficients yields useful results for further evaluation.

Validity criteria fulfilled:
not applicable
Conclusions:
The organic carbon partition coefficient (log Koc) of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' was predicted using the Estimation Program Interface (EPI) Suite version 4.1.
'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' is a "multi constituent substance" consisting of benzyl 2-ethylhexyl adipate [CAS 58394-64-2], bis(2-ethylhexyl) adipate [CAS 103-23-1] and dibenzyl adipate [CAS 2451-84-5].
The estimation revealed values of 23290 L/kg (log Kow method) and 21900 L/kg (MCI method) for benzyl 2-ethylhexyl adipate, 2811 L/kg (log Kow method) and 13320 L/kg (MCI method) for dibenzyl adipate and 192900 L/kg (log Kow method) and 36000 L/kg (MCI method) for bis(2-ethylhexyl) adipate. All values indicate a potential for adsorption.
Executive summary:

The organic carbon partition coefficient (log Koc) of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' was predicted using the Estimation Program Interface (EPI) Suite version 4.1.

'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' is a "multi constituent substance" consisting of benzyl 2-ethylhexyl adipate [CAS 58394-64-2], bis(2-ethylhexyl) adipate [CAS 103-23-1] and dibenzyl adipate [CAS 2451-84-5].

For each constituent of the substance the program estimated the Koc with two separate estimation methodologies. The estimations are based on the first-order Molecular Connectivity Index (MCI) and the log Kow, which is internally calculated by the program, respectively.

 

For estimating Koc, based on the method on statistical relationships between Koc and the octanol/water partition coefficient (Kow) the following log Kow values were used:

 

constituent A [benzyl 2-ethylhexyl adipate]: log Kow 6.46

constituent B [bis(2-ethylhexyl) adipate]: log Kow 8.12

constituent C [dibenzyl adipate]: log Kow 4.80

 

Koc values in the range of 2811 to 192900 L/kg were obtained.

 

Moreover, calculations performed based upon the molecule structure using the molecular connectivity method (MCI method) yielded Koc values in the range of 13320 to 36000 L/kg.

 

The results for all constituents of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' falls within the applicability domain of the model and the applied estimating rules appear appropriate. Concerning uncertainties of estimation for the investigated substances, bis(2-ethylhexyl) adipate is located in the training dataset. Thus, the probability is high, that the structural fragments applied by the program for the substance of interest were appropriate.

For bis(2-ethylhexyl) adipate the residual, defined as the difference between the experimental log Koc value and the log Koc values predicted by the MCI- and log Kow-method, expressed as absolute value, is +0.37 for the MCI method, and +1.10 for the log Kow method.

The uncertainty can be stated due to the lack of information of the experimental study design, as bis(2-ethylhexyl) adipatee is poorly soluble in water.

Therefore, the experimentally determined log Koc for bis(2-ethylhexyl) adipate reported in the database of the program, cannot be used for hazard and risk assessment and the value is scored to be not assignable.

Further, the predicted log Kow for bis(2-ethylhexyl) adipate is 8.12. It is assumed that log Koc results predicted by the log Kow method are less accurate with increasing log Kow values, due to low level presence of compounds with higher log Kow values in the training set.

Regarding the predicted values for benzyl 2-ethylhexyl adipate and dibenzyl adipate it is considered that their uncertainty is in the same range as bis(2-ethylhexyl) adipate. Nevertheless, the predictions of the organic carbon partition coefficients yield useful results for further evaluation, indicating a potential for adsorption.

Description of key information

The organic carbon partition coefficient (log Koc) of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' was predicted using the Estimation Program Interface (EPI) Suite version 4.1.
'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' is a "multi constituent substance" consisting of benzyl 2-ethylhexyl adipate [CAS 58394-64-2], bis(2-ethylhexyl) adipate [CAS 103-23-1] and dibenzyl adipate [CAS 2451-84-5].



The estimation revealed values of


 


23290 L/kg (log Kow method) and 21900 L/kg (MCI method) for benzyl 2-ethylhexyl adipate (approx. 50% of the substance)


192900 L/kg (log Kow method) and 36000 L/kg (MCI method) for bis(2-ethylhexyl) adipate (approx. 30% of the substance)


2811 L/kg (log Kow method) and 13320 L/kg (MCI method) for dibenzyl adipate (approx. 20% of the substance)


 


All values indicate a potential for adsorption. The weighted mean value of the individual KOC calculated via the KOW method (based on the proportion of the constituent in relation to the multi constituent substance) was calculated as KOC = 70077 and used as key value for assessment.

Key value for chemical safety assessment

Koc at 20 °C:
70 077

Additional information

The organic carbon partition coefficient (log Koc) of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' was predicted using the Estimation Program Interface (EPI) Suite version 4.1.


'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' is a "multi constituent substance" consisting of benzyl 2-ethylhexyl adipate [CAS 58394-64-2], bis(2-ethylhexyl) adipate [CAS 103-23-1] and dibenzyl adipate [CAS 2451-84-5].


 


For each constituent of the substance the program estimated the Koc with two separate estimation methodologies. The estimations are based on the first-order Molecular Connectivity Index (MCI) and the log Kow, which is internally calculated by the program, respectively.


For estimating Koc, based on the method on statistical relationships between Koc and the octanol/water partition coefficient (Kow) the following log Kow values were used:


 


constituent A [benzyl 2-ethylhexyl adipate]: log Kow 6.46


constituent B [bis(2-ethylhexyl) adipate]: log Kow 8.12


constituent C [dibenzyl adipate]: log Kow 4.80


 


Koc values in the range of 2811 to 192900 L/kg were obtained.


 


Moreover, calculations performed based upon the molecule structure using the molecular connectivity method (MCI method) yielded Koc values in the range of 13320 to 36000 L/kg.


 


The results for all constituents of 'Reaction mass of benzyl 2-ethylhexyl adipate and bis(2-ethylhexyl) adipate and dibenzyl adipate' falls within the applicability domain of the model and the applied estimating rules appear appropriate. Concerning uncertainties of estimation for the investigated substances, bis(2-ethylhexyl) adipate is located in the training dataset. Thus, the probability is high, that the structural fragments applied by the program for the substance of interest were appropriate.


For bis(2-ethylhexyl) adipate the residual, defined as the difference between the experimental log Koc value and the log Koc values predicted by the MCI- and log Kow-method, expressed as absolute value, is +0.37 for the MCI method, and +1.10 for the log Kow method.


The uncertainty can be stated due to the lack of information of the experimental study design, as bis(2-ethylhexyl) adipate is poorly soluble in water.


Therefore, the experimentally determined log Koc for bis(2-ethylhexyl) adipate reported in the database of the program, cannot be used for hazard and risk assessment and the value is scored to be not assignable.


Further, the predicted log Kow for bis(2-ethylhexyl) adipate is 8.12. It is assumed that log Koc results predicted by the log Kow method are less accurate with increasing log Kow values, due to low level presence of compounds with higher log Kow values in the training set.


Regarding the predicted values for benzyl 2-ethylhexyl adipate and dibenzyl adipate it is considered that their uncertainty is in the same range as bis(2-ethylhexyl) adipate. Nevertheless, the predictions of the organic carbon partition coefficients yield useful results for further evaluation, indicating a potential for adsorption.