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Endpoint:
adsorption / desorption: screening
Type of information:
experimental study
Adequacy of study:
key study
Study period:
17 May 2013 - 26 June 2013
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
guideline study
Qualifier:
according to
Guideline:
OECD Guideline 121 (Estimation of the Adsorption Coefficient (Koc) on Soil and on Sewage Sludge using High Performance Liquid Chromatography (HPLC))
Deviations:
no
Qualifier:
according to
Guideline:
EU Method C.19 (Estimation of the Adsorption Coefficient (KOC) on Soil and Sewage Sludge Using High Performance Liquid Chromatography (HPLC))
Deviations:
no
GLP compliance:
yes (incl. certificate)
Type of method:
HPLC estimation method
Media:
soil/sewage sludge
Radiolabelling:
no
Test temperature:
30 deg C
Details on study design: HPLC method:
EQUIPMENT
- Apparatus: Agilent Technologies 1100 incorporating autosampler Polymer Laboratories Evaporative Light Scattering Detector 2100 (ELSD)
- Type, material and dimension of analytical column: Waters XSelect HSS cyano 5 |im (150 x 4.6 mm id)
- Injection volume: 5 uL
- Detection system: Polymer Laboratories Evaporative Light Scattering Detector 2100 (ELSD); UV detector
- ELSD parameters: Nebulizer temperature 40 deg C; Evaporator temperature 80 deg C; Gas flow 10. SLM
- UV detector wavelength: dead time and reference standards: 210 nm

MOBILE PHASES
- Type: Methanol: water (55:45 v/v), flow rate 1.0 mL/min. The mobile phase was ramped to 100 % methanol shortly after the elution of the last reference
standard to elute the highly retained test item components. This was carried out for the sample and sample blank injections only.
- Experiments with additives carried out on separate columns: no
- pH: 7.1
- Solutes for dissolving test and reference substances: Methanol

DETERMINATION OF DEAD TIME
- Method: The dead time was determined by measuring the retention time of formamide (purity*: 99.94%) at 820 mg/L in methanol:water (55:45 v/v).

REFERENCE SUBSTANCES
- Identity: Acetanilide; phenol; atrazine; isoproturon; triadimenol; linuron; naphthalene; endosulfan-diol; fenthion; alpha-endosulfan; phenanthrene, diclofop-methyl; DDT

DETERMINATION OF RETENTION TIMES
- Quantity of test substance introduced in the column: 3.01 ug
- Quantity of reference substances: 0.5 ug


REPETITIONS
- Number of determinations: 2

EVALUATION
- Calculation of capacity factors k': k' = tr-t0/t0; where tr = retention time (min) and t0 = dead time (min)
- Calculation of retention times:
- Determination of the log Koc value: LogKoc = Logk'-A/B; where A = intercept of the calibration curve and B = slope of calibration curve
Type:
Koc
Value:
> 427 000 L/kg
Temp.:
30 °C
Type:
log Koc
Value:
> 5.63 dimensionless
Temp.:
30 °C
Details on results (HPLC method):
- Retention times of reference substances used for calibration: see tables attached
- Details of fitted regression line (log k' vs. log Koc): y = 0.3358x-0.7231; R2 = 0.9291
- Graph of regression line attached: yes
- Average retention data for test substance: Retention time 34.250 & 34.300 mins.

The main components of the test item had no dissociation constants within the environmentally relevant pH range and therefore, the test item was tested at an approximately neutral mobile phase.

As the slope of the calibration curve for the reference standards showed good first order correlation and as the retention times between duplicate injections for each solution were consistent, the HPLC method was considered valid for the determination of adsorption

coefficient. Based on the chromatographic data, the test item was considered to be stable during the test procedure.

Validity criteria fulfilled:
not applicable
Conclusions:
The adsorption coefficient (Koc) of the test item has been determined to be greater than 4.27E05, logKoc >5.63.
Executive summary:

Test System

The determination was carried out using the HPLC screening method, designed to be compatible with Method CI9 Adsorption Coefficient of Commission Regulation (EC) No 440/2008 of 30 May 2008 and Method 121 of the OECD Guidelines for Testing of Chemicals, 22 January 2001.

The test utilized a high performance liquid chromatograph. A commercially available cyanopropyl reverse phase HPLC column containing lipophilic and polar moieties was used.

Conclusion

The adsorption coefficient (Koc) of the test item has been determined to be greater than 4.27E05, logKoc >5.63.

Endpoint:
adsorption / desorption: screening
Type of information:
experimental study
Adequacy of study:
supporting study
Study period:
2008-08-28 to 2008-12-04
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: see 'Remark'
Remarks:
GLP - Guideline study, tested with the source substance Ester reaction products of fatty acid, C5-10, pentaerythritol and dipentaerythritol. In accordance to the ECHA guidance document “Practical guide 6: How to report read-across and categories (March 2010)”, the reliability was changed from RL1 to RL2 to reflect the fact that this study was conducted on a read-across substance.
Qualifier:
according to
Guideline:
OECD Guideline 121 (Estimation of the Adsorption Coefficient (Koc) on Soil and on Sewage Sludge using High Performance Liquid Chromatography (HPLC))
GLP compliance:
yes (incl. certificate)
Type of method:
HPLC estimation method
Media:
soil
Specific details on test material used for the study:
Details on properties of test surrogate or analogue material (migrated information):
The justification for read-across is presented in Section 13 Assessment reports- Read-across justification.
Radiolabelling:
no
Test temperature:
25 °C
Details on study design: HPLC method:
EQUIPMENT
- Apparatus: HPLC-UV
- Type: Hewlett Packard 1050 Liquid Chromatograph
- Type, material and dimension of analytical (guard) column: Hypersil CPS (25 cm x 4.6 mm internal diameter)
- Detection system: UV detector

MOBILE PHASES
- Type: Acetonitrile : water (55:45 v/v)
- Experiments with additives carried out on separate columns: no
- pH: no data
- Solutes for dissolving test and reference substances: HPLC mobile phase

DETERMINATION OF DEAD TIME
- Method: by inert substances which are not retained by the column (formamide)

REFERENCE SUBSTANCES
- Identity: Acetanilide, Nitrobenzene, Naphthalene, 2-Methylnaphthalene, Anthracene, DDT

DETERMINATION OF RETENTION TIMES
- Quantity of test substance introduced in the column: 100 µL
- Quantity of reference substances: 20 µL
- Intervals of calibration: no data

REPETITIONS
- Number of determinations: duplicate

EVALUATION
- Calculation of capacity factors k': k = t'r / t0 = (tr - t0)/t0
- Calculation of retention times: true retention time obtained by subtracting deadtime, or t0 of I.D.S. from measured retention time of sample or reference.
- Determination of the log Koc value: log Koc = 4.99 log10k + 5.58
Type:
log Koc
Value:
4 - 7
Temp.:
25 °C

HPLC determination og log10Koc for the test item

Sample

Component

tr(minutes)

k

log10k

log10Koc

Standard Run A (t0= 3.177 minutes)

Acetanilide

3.548

0.117

-0.933

1.3

Nitrobenzene

3.959

0.246

-0.609

2.4

Naphthalene

4.360

0.372

-0.429

2.8

2-Methylnaphthalene

4.521

0.423

-0.374

3.9

Anthracene

4.852

0.527

-0.278

4.4

DDT

6.105

0.922

-0.035

5.6

Sample A (t0= 3.228 minutes)

Test item

5.0 – 9.5

0.549 – 1.943

-0.267 – 0.288

4.3 – 7.0

Sample B (t0= 3.245 minutes)

Test item

5.0 – 9.5

0.541 – 1.928

-0.267 – 0.285

4.3 – 7.0

Standard Run B (t0= 3.166 minutes)

Acetanilide

3.537

0.117

-0.931

1.3

Nitrobenzene

3.948

0.247

-0.607

2.4

Naphthalene

4.350

0.374

-0.427

2.8

2-Methyl-naphthalene

4.511

0.425

-0.372

3.9

Anthracene

4.842

0.529

-0.276

4.4

DDT

6.097

0.926

-0.033

5.6

Linear regression (based on mean of standard runs A and B)

log10Koc = 4.99 log10k + 5.58

Endpoint:
adsorption / desorption: screening
Type of information:
other: Expert statement
Adequacy of study:
supporting study
Study period:
1997/07/09
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Expert statement (test technically not feasible)
Qualifier:
according to
Guideline:
OECD Guideline 106 (Adsorption - Desorption Using a Batch Equilibrium Method)
Principles of method if other than guideline:
Only expert statement, test technically not feasible.
GLP compliance:
yes
Media:
sediment
Specific details on test material used for the study:
Details on properties of test surrogate or analogue material (migrated information):
The justification for read-across is presented in Section 13 Assessment reports- Read-across justification.
Analytical monitoring:
yes
Type:
other: Determination was not possible

According to the OECD guideline for testing of chemicals no. 106 (Screening version): “Adsorption/Desorption”, adopted May 12, 1981, the method as described is not applicable to substances which are not soluble in water to an extent which can be measured analytically. Since it was not possible to develop an analytical method that was selective and sensitive enough to measure concentrations of the test substance in aqueous samples accurately, the adsorption/desorption study can not be performed with this test substance.

Endpoint:
adsorption / desorption: screening
Remarks:
adsorption
Type of information:
(Q)SAR
Adequacy of study:
supporting study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Scientifically acceptable calculation
Principles of method if other than guideline:
KOCWIN v2.00
GLP compliance:
no
Type of method:
other: estimated by calculation
Media:
soil
Specific details on test material used for the study:
Details on properties of test surrogate or analogue material (migrated information):
The justification for read-across is presented in Section 13 Assessment reports- Read-across justification.
Analytical monitoring:
no
Type:
log Koc
Value:
6.679
Remarks on result:
other: C30 H56 O6, calculation based on log Kow
Type:
log Koc
Value:
7.089
Remarks on result:
other: C30 H56 O6, MCI method
Type:
log Koc
Value:
8.311
Remarks on result:
other: C36 H68 O6, calculation based on log Kow
Type:
log Koc
Value:
8.653
Remarks on result:
other: C36 H68 O6, MCI method

In order to covering the range of chain length of the test substance, the calculation was realised with smiles-codes for the shortest and longest chain length.

KOCWIN Program (v2.00) Results:

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

SMILES : O=C(OCC(CC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC)CCCCCCC

CHEM  :

MOL FOR: C30 H56 O6

MOL WT : 512.78

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

 

Koc Estimate from MCI:

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

First Order Molecular Connectivity Index ........... : 17.424

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 9.6830

Fragment Correction(s):

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

Corrected Log Koc .................................. : 7.0891

 

Estimated Koc: 1.228e+007 L/kg  <===========

 

Koc Estimate from Log Kow:

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

Log Kow (Kowwin estimate) ......................... : 10.64

Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 6.8104

Fragment Correction(s):

2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312

Corrected Log Koc .................................. : 6.6792

 

Estimated Koc: 4.778e+006 L/kg  <===========

KOCWIN Program (v2.00) Results:

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

SMILES : O=C(OCC(CC)(COC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC)CCCCCCCCC

CHEM  :

MOL FOR: C36 H68 O6

MOL WT : 596.94

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

 

Koc Estimate from MCI:

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

First Order Molecular Connectivity Index ........... : 20.424

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 11.2469

Fragment Correction(s):

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

Corrected Log Koc .................................. : 8.6530

 

Estimated Koc: 4.498e+008 L/kg  <===========

 

Koc Estimate from Log Kow:

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

Log Kow (Kowwin estimate) ......................... : 13.59

Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 8.4421

Fragment Correction(s):

2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312

Corrected Log Koc .................................. : 8.3109

 

Estimated Koc: 2.046e+008 L/kg  <===========

 

Endpoint:
adsorption / desorption: screening
Type of information:
(Q)SAR
Adequacy of study:
supporting study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Scientifically acceptable calculation
Principles of method if other than guideline:
KOCWIN v2.00
GLP compliance:
no
Type of method:
other: estimated by calculation
Media:
soil
Specific details on test material used for the study:
Details on properties of test surrogate or analogue material (migrated information):
There is no specific data on the substance. Read-across to the physico-chemical properties of Hexanoic acid, 3,5,5-trimethyl-, 1,1'-[2-ethyl-2-[[(3,5,5-trimethyl-1-oxohexyl)oxy]methyl]-1,3-propanediyl] ester (EC 613-848-7, CAS65870-94-2) is applicable based on the similarity in structure and physico-chemical properties.
The justification for read-across is presented in Section 13 Assessment reports- Read-across justification.
Radiolabelling:
no
Analytical monitoring:
no
Type:
log Koc
Value:
7.188
Remarks on result:
other: calculation based on log Kow
Type:
log Koc
Value:
7.152
Remarks on result:
other: MCI method

KOCWIN Program (v2.00) Results:

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

SMILES : C(CC)(COC(=O)CC(C)CC(C)(C)(C))(COC(=O)CC(C)CC(C)(C)(C))(COC(=O)CC(C)C

C(C)(C)(C))

CHEM  : Hexanoic acid, 3,5,5-trimethyl-, 1,1'-[2-ethyl-2-[[(3,5,5-trimethyl-1

-oxohexyl)oxy]methyl]-1,3-propanediyl] ester

MOL FOR: C33 H62 O6

MOL WT : 554.86

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

 

Koc Estimate from MCI:

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

First Order Molecular Connectivity Index ........... : 17.545

Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 9.7460

Fragment Correction(s):

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

Corrected Log Koc .................................. : 7.1521

 

Estimated Koc: 1.419e+007 L/kg  <===========

 

Koc Estimate from Log Kow:

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

Log Kow (Kowwin estimate) ......................... : 11.56

Non-Corrected Log Koc (0.55313 logKow + 0.9251) .... : 7.3193

Fragment Correction(s):

2  Ester (-C-CO-O-C-) or (HCO-O-C) ...... : -0.1312

Corrected Log Koc .................................. : 7.1881

 

Estimated Koc: 1.542e+007 L/kg  <===========

Endpoint:
adsorption / desorption: screening
Type of information:
read-across from supporting substance (structural analogue or surrogate)
Adequacy of study:
key study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: analogue substance
Justification for type of information:
Investigation of adsorption/desorption is not required because available data indicate that structural variation does not influence test results or adverse effect profile (see read-across and category justifications attached in Section 13).
Reason / purpose:
read-across source
Type:
Koc
Value:
> 427 000 L/kg
Temp.:
30 °C
Type:
log Koc
Value:
5.63 dimensionless
Temp.:
30 °C

Description of key information

There is a high adsorption of the test item to soil and sediment particles (Estimated log Koc >5.63).

Key value for chemical safety assessment

Additional information

One reliable study is available. In this study (Fox, 2013) performed under GLP, the adsorption coefficient of the test item was determined using the HPLC Screening method, according to OECD TG 121 and EC Method C19.The test utilized a high performance liquid chromatograph. A commercially available cyanopropyl reverse phase HPLC column containing lipophilic and polar moieties was used. The adsorption coefficient (Koc) of the test item has been determined to be greater than 4.27 x 10E05, LogKoc >5.63.

 

The experimental result is supported by an estimation using KOCWIN v2.00 with smiles notation. Log Koc values of 7.1881 (estimate from log Kow) and 7.1521 (estimate with MCI method) were calculated for the substance indicating a high adsorption potential.

 

The Log Kow of the substance is > 9.4 which supports the high estimated Log Koc value.

 

Read-across to the environmental fate properties of Decanoic acid, ester with 2-ethyl-2-(hydroxymethyl)-1,3-propanediol octanoate (EC 234-392-1, CAS 11138-60-6)) and its analogues is applicable based on the similarity in structure and physico-chemical properties. The justification for read-across is presented in Section 13 Assessment reports- Read-across justification.

 

The result for EC 613 -848 -7 is supported by the read-across to data on Ester reaction products of fatty acid, C5-10, pentaerythritol and dipentaerythritol, where a log Koc of 4 - 7 was established in a guideline study according to OECD 121 under GLP conditions.

Furthermore, testing on the read-across substance Fatty acids, C14-18 and C18-unsatd., branched and linear, esters with trimethylolpropane (CAS 85005-23-8) indicated that a study may not be technically feasible due to the low water solubility.