A mixture of: 7,9,9-trimethyl-3,14-dioxa-4,13-dioxo-5,12-diazahexadecane-1,16-diylprop-2-enoate; 7,7,9-trimethyl-3,14-dioxa-4,13-dioxo-5,12-diazahexadecan-1,16-diylprop-2-enoate

Adsorption / desorption

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

adsorption / desorption: screening

Type of information:

calculation (if not (Q)SAR)

Adequacy of study:

supporting study

Study period:

2009

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

other: The Koc value was estimated by calculation using the software KOCWIN v 2.00.

Qualifier:

according to guideline

Guideline:

other: KOCWIN v 2.00

Deviations:

not applicable

GLP compliance:

no

Type of method:

other: calculated (KOCWIN v 2.0)

Test temperature:

not applicable

Analytical monitoring:

not required

Computational methods:

- Adsorption coefficient per organic carbon (Koc): calculated using the software KOCWIN v 2.00

Key result

Type:

log Koc

Value:

3.262 dimensionless

Remarks on result:

other: for Constituent 1 and Constituent 2

Details on results (HPLC method):

not applicable

Adsorption and desorption constants:

not applicable

Recovery of test material:

not applicable

Concentration of test substance at end of adsorption equilibration period:

not applicable

Concentration of test substance at end of desorption equilibration period:

not applicable

Transformation products:

not specified

Details on results (Batch equilibrium method):

see below

Constituent 1:

SMILES : C=CC(=O)(OCCOC(=O)(NCCC(CC((=O)(OCCOC(=O)(C=C)))(C)C)C))

CHEM  :#41137-63-7

MOL FOR: C21 H34 N2 O8

MOL WT : 442.51

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

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 14.591

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 8.2059

        Fragment Correction(s):

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

                 2  Carbamate (N-CO-O) or (N-CO-S) ....... : -1.9203

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

        Corrected Log Koc .................................. : 3.2662

 

                        Estimated Koc: 1846 L/kg  <===========

Constituent 2:

SMILES : C=CC(=O)(OCCOC(=O)((CC(CCNC(=O)(OCCOC(=O)(C=C)))(C)C)C))

CHEM  :#67910-48-9

MOL FOR: C21 H34 N2 O8

MOL WT : 442.51

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

 

 Koc Estimate from MCI:

 ---------------------

        First Order Molecular Connectivity Index ........... : 14.591

        Non-Corrected Log Koc (0.5213 MCI + 0.60) .......... : 8.2059

        Fragment Correction(s):

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

                 2  Carbamate (N-CO-O) or (N-CO-S) ....... : -1.9203

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

        Corrected Log Koc .................................. : 3.2662

 

                        Estimated Koc: 1846 L/kg

Validity criteria fulfilled:

yes

Conclusions:

Under the study conditions, the estimated log Koc for the constituents 1 and 2 was 3.2662.

Executive summary:

A study was conducted to determine adsorption / desorption partition coefficient using QSAR modelling by KOCWIN v 2.0. Under the study conditions, the estimated log Koc for the constituents 1 and 2 was 3.2662 (US EPA, 2014).

Reference 2

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Study period:

From August 25, 2011 to August 29, 2011

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Qualifier:

according to guideline

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

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. QA statement)

Type of method:

HPLC estimation method

Radiolabelling:

no

Test temperature:

35°C +/- 1°C

Details on study design: HPLC method:

Analytical conditions
Instrument: Alliance Separation Module 2695 (Waters, Milford, MA, USA)
Detector: Dual λ Absorbance Detector 2487 (Waters)
Column: Hypersil BDS-CN, 150 mm x 4.6 mm i.d., dp = 5 µm (Thermo Fisher Scientific, Waltham, MA, USA)
Column temperature: 35°C +/- 1°C

Mobile phase: 30/70 (v/v) methanol/water
Flow: 1 ml/min
Injection volume: 10 µl
UV detection: 210 nm

Preparation of the solutions
All solutions containing the test substance were protected from light.

Solution of the unretained compound: A 4.81 g/l stock solution of formamide (99.8%, CAS Number: 75-12-7, Acros Organics, Geel, Belgium) in methanol was used. The stock solution was diluted to obtain an end solution of 30/70 (v/v) /water.
The formamide blank solution was 30/70 (v/v) methanol/water.

Reference substance solutions: Stock solutions of the reference substances at concentrations of approximately 7 g/l in methanol were used. The stock solutions were diluted to obtain an end solution of 30/70 (v/v) methanol/water.
The blank solution for the mixture of reference substances was 30/70 (v/v) methanol/water.
See also Table below.

Test solution: A 6804 mg/l stock solution of the test substance was prepared in methanol. The stock solution was diluted to obtain an end solution of 30/70 (v/v) methanol/water. The final concentration of the test substance solution was 129 mg/l.
The test substance blank solution was 30/70 (v/v) methanol/water.

Injections: The reference substance and test substance solutions were injected in duplicate. Blank solutions were analysed by single injection.

Details on test conditions:

According to the guidelines, the determination of the Koc for test substances that are ionized for at least 10% within pH 5.5 to 7.5 should be performed with both the ionized and non-ionized form. Therefore, the pK, values of the test substance were calculated using the Perrin calculation method (pKalc 5.0, module in Pallas 3.0, CompuDrug International San Francisco, USA). Based on the calculations, the HPLC analysis was performed at neutral pH.

Solutions of reference substances with known log Koc values based on soil adsorption data and the test substance were analysed. The capacity factor (k') of each compound was calculated from its retention time. The log k' values of the references substances were plotted against the known log Koc values. A linear regression program was used to calculate the calibration curve. Linear regression analysis was performed using the least squares method. The coefficient of correlation (r) was calculated. The log Kc, value for the test substance was calculated by substituting its mean log k' in the calibration curve. The value of log K,,, obtained from duplicate measurements was within ± 0.25 log units.

Key result

Sample No.:

#1

Type:

log Koc

Value:

3.22 dimensionless

pH:

7

Temp.:

35 °C

Remarks on result:

other: major compound

Key result

Sample No.:

#2

Type:

log Koc

Value:

0.48 dimensionless

pH:

7

Temp.:

35 °C

Remarks on result:

other: Impurity II

Key result

Sample No.:

#3

Type:

log Koc

Value:

2.42 dimensionless

pH:

7

Temp.:

35 °C

Remarks on result:

other: Impurity V

Key result

Sample No.:

#4

Type:

log Koc

Value:

3.54 dimensionless

pH:

7

Temp.:

35 °C

Remarks on result:

other: Impurity VII

Details on results (HPLC method):

Calculation of pKa values: No pKa values for acidic and basic groups in the molecular structure of the test substance in the logarithm range of 0 - 14 were calculated.

Determination of the Koc:
In the chromatogram of the test solution, one major peak and several small test substance peaks were observed.
The equation of the regression line was: log k’ = 0.509 x log Koc – 0.911 (r = 0.957, n = 14).

The K_ocand log K_ocvalue of the test substance and impurities at neutral pH was:

 

	Koc	log Koc	Area %
Impurity I	3.0	0.48	6.7
Impurity II	2.7´10^2	2.42	1.2
Major compound	1.7´10^3	3.22	90
Impurity III	3.5´10^3	3.54	1.3

Validity criteria fulfilled:

yes

Conclusions:

Under the study conditions, the Koc and log Koc values of the test substance and three impurities with peak areas > 1 % were determined by the HPLC method based on soil-adsorption-reference data. The values obtained are following: Impurity I: Koc=3.0; log Koc=0.48; Impurity II: Koc=2.7 x 10^2; log Koc=2.42; Major compound: Koc=1.7 x 10^3; log Koc=3.22; Impurity III: Koc=3.5 x 10^32; log Koc=3.54.

Executive summary:

A study was conducted to determine the adsorption coefficient of the test substance on soil and on sewage sludge using high performance liquid chromatography (HPLC) according to OECD Guideline 121 and EU Method C.19, in compliance with GLP. Under the study conditions, the Koc and log Koc values of the test substance and three impurities with peak areas > 1 % were determined by the HPLC method based on soil-adsorption-reference data. The values obtained are following: Impurity I: Koc=3.0; log Koc=0.48; Impurity II: Koc=2.7 x 10E2; log Koc=2.42; Major compound: Koc=1.7 x 10E3; log Koc=3.22; Impurity III: Koc=3.5 x 10E3; log Koc=3.54. Under the test conditions, the adsorption coefficient of the substance was determined to be log Koc = 3.22 (Koc = 1700) (Baltussen, 2011).

Key value for chemical safety assessment

Koc at 20 °C:

1 700

Additional information

Study 1:

A study was conducted to determine the adsorption coefficient of the test substance on soil and on sewage sludge using high performance liquid chromatography (HPLC) according to OECD Guideline 121 and EU Method C.19, in compliance with GLP. Under the study conditions, the Koc and log Koc values of the test substance and three impurities with peak areas > 1 % were determined by the HPLC method based on soil-adsorption-reference data. The values obtained are following: Impurity I: Koc=3.0; log Koc=0.48; Impurity II: Koc=2.7 x 10E2; log Koc=2.42; Major compound: Koc=1.7 x 10E3; log Koc=3.22; Impurity III: Koc=3.5 x 10E3; log Koc=3.54. Under the test conditions, the adsorption coefficient of the substance was determined to be log Koc = 3.22 (Koc = 1700) (Baltussen, 2011).

 

Study 2:

A study was conducted to determine adsorption / desorption partition coefficient using QSAR modelling by KOCWIN v 2.0. Under the study conditions, the estimated log Koc for the constituents 1 and 2 was 3.2662 (US EPA, 2014).