2-Propenoic acid, 2-[2-(ethenyloxy)ethoxy]ethyl ester

Adsorption / desorption

Link to relevant study record(s)

Reference

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Study period:

between March 28, 2006 and May 29, 2006

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

other: Study conducted to GLP and in compliance with agreed protocols, with no or minor deviations from standard test guidelines and/or minor methodological deficiencies, which do no effect the quality of the relevant results

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)

Remarks:

Date of inspection: April 2005 Date of Signature: November 2005

Type of method:

HPLC estimation method

Media:

soil

Radiolabelling:

no

Test temperature:

25°C

Details on study design: HPLC method:

For the estimation of the adsorption coefficient, the HPLC-method was used. Therefore, an analytical column packed with a commercially available, cyanopropyl solid phase containing lipophilic and polar moieties was used. A moderately polar stationary phase based on a silica matrix was used.

While passing through the column along with the mobile phase, the test item interacts with the stationary phase. As a result of partitioning between mobile and stationary phases, the test item is retarded. The dual composition of the stationary phase having polar and non-polar sites allows for interaction of polar and non-polar groups of a molecule in a similar way as is the case for organic matter in soil or sewage sludge matrices. This enables the relationship between the retention time on the column and the adsorption coefficient on organic matter to be established.

This method utilises a high performance liquid chromatograph with UV/VIS detector, reversed
phase column and an aqueous mobile phase.

Analytical monitoring:

yes

Details on sampling:

2-(2-Vinyloxyethoxy)ethyl acrylate (45.21 mg) was dissolved in acetonitrile (10 ml) to prepare
a stock solution of 4521 μg/ml. The stock solution (100 μl) was diluted with a solvent mixture
of water and methanol (45:55; v/v) to 10 ml to obtain a standard solution of 45.21 μg/ml. The
pH value of the test item solution was determined to be 6.9. This test item solution was
injected three times.

Stock solutions of the reference items were prepared as described:
10.27 mg of the isoproturon, 10.22 mg of the linuron, 10.39 mg of the 2,4-DDT, 10.56 mg of
the diclofop-methyl and 10.38 mg of the acetanilide were each dissolved in 10 ml of
methanol. 21.08 mg of the reference item pyrazophos were dissolved in 20 ml of methanol.
A combined reference solution was prepared by transferring 130 μl of the acetanilide stock
solution, 140 μl of the isoproturon stock solution, 75 μl of the linuron stock solution, 1000 μl of
the pyrazophos stock solution, 150 μl of the diclofop-methyl stock solution and 285 μl of the
2,4-DDT stock solution into one volumetric flask and diluting to a volume of 10 ml with a
solvent mixture of water and methanol (45:55; v/v). This reference solution was injected six
times.
Sodium nitrate (5.71 mg) was dissolved in 25 ml of methanol to obtain a stock solution. The
stock solution (100 μl) was diluted to 1 ml with a solvent mixture of water and methanol
(45:55; v/v). This sodium nitrate solution was injected twice for the determination of the dead
time of the HPLC system.

Computational methods:

Not applicable.

Type:

Koc

Value:

15

Temp.:

20 °C

Type:

log Koc

Value:

1.2

Temp.:

20 °C

Details on results (HPLC method):

Use drop down list:
- Retention times of reference substances used for calibration: see table 1 in attachment 1
- Details of fitted regression line (log k' vs. log Koc): see figure 4
- Graph of regression line attached: yes
- Average retention data for test substance: mean retention time has been given for the reference substances but not for the test substance.

Calibration
The retention times of formamide and the retention times, capacity factors (k) and log10 Koc values for the reference standards and test material are shown in tables 2 and 3

Statistics:

None stated.

The determination of the adsorption coefficient (KOC) of 2-(2-Vinyloxyethoxy)ethyl acrylate was performed according to the OECD Guideline for the Testing of Chemicals, No. 121, Estimation of the Adsorption Coefficient (KOC) on Soil and Sewage Sludge using High Performance Liquid Chromatography (HPLC), January, 2001 and the EC Directive 2001/59, C.19.

The test item solution was injected three times and the combined reference solution was injected six times. The log KOC of the test item was calculated using a regression curve (log k’ vs. log KOC) and was found to be 1.2 which is equal to KOC of 15. In the present study the reference items covered the range of log KOC 1.25 to log KOC 5.63.

A typical HPLC chromatogram of the reference standard mixture is shown in Figure 1. An HPLC chromatogram of the test item is shown in Figure 2. A typical chromatogram of the determination of the dead-time is given in Figure 3. The chromatography of the test item resulted in one main peak with a well-defined and reproducible retention time. The HPLC method was therefore considered to be suitable for the purpose of the study. Based on the chromatographic data, 2-(2-Vinyloxyethoxy)ethyl acrylate was considered to be stable during the test procedure.

The retention times of the individual measurements of the reference items, test item and the dead time are given in Table 1. The capacity factor (k’) was calculated for each reference item using the retention times. Log KOC was plotted versus log k for each component to obtain a regression curve (Table 2 and Figure 4).

The tabulated values represent rounded mean results, which were obtained by calculation using the exact raw data.

In conclusion, the log of the adsorption coefficient (KOC) of 2-(2-Vinyloxyethoxy)ethyl acrylate was estimated to be:

log KOC = 1.2 which is equal to a KOC value of 15 using the HPLC method. This value indicates that 2-(2-Vinyloxyethoxy)ethyl acrylate will not be adsorbed by organic carbon in soil. 2-(2-Vinyloxyethoxy)ethyl acrylate can be classified to be of very high mobility.

Validity criteria fulfilled:

not specified

Conclusions:

In conclusion, the log of the adsorption coefficient (KOC) of 2-(2-Vinyloxyethoxy)ethyl acrylate was estimated to be:
log KOC = 1.2 which is equal to a KOC value of 15 using the HPLC method. This value indicates that 2-(2-Vinyloxyethoxy)ethyl acrylate will not
be adsorbed by organic carbon in soil. 2-(2-Vinyloxyethoxy)ethyl acrylate can be classified to be of very high mobility.

Executive summary:

Method:

The determination of the adsorption coefficient (KOC) of 2-(2-Vinyloxyethoxy)ethyl acrylate was performed according to the OECD Guideline for the Testing of Chemicals, No. 121, Estimation of the Adsorption Coefficient (KOC) on Soil and Sewage Sludge using High Performance Liquid Chromatography (HPLC), January, 2001 and the EC Directive 2001/59, C.19.

Conclusion:

In conclusion, the log of the adsorption coefficient (KOC) of 2-(2-Vinyloxyethoxy)ethyl acrylate was estimated to be: log KOC = 1.2 which is equal to a KOC value of 15 using the HPLC method. This value indicates that 2-(2-Vinyloxyethoxy)ethyl acrylate will not be adsorbed by organic carbon in soil. 2-(2-Vinyloxyethoxy)ethyl acrylate can be classified to be of very high mobility.

Description of key information

The log of the adsorption coefficient (Koc) of 2-(2-Vinyloxyethoxy)ethyl acrylate was estimated to be log Koc = 1.2 which is equal to a Koc value of 15

Key value for chemical safety assessment

Koc at 20 °C:

15

Additional information

The results (LogKoc 1.2) indicate that 2-(2-Vinyloxyethoxy)ethyl acrylate will not be adsorbed by organic carbon in soil. 2-(2-Vinyloxyethoxy)ethyl acrylate can be classified to be of very high mobility.