Reaction mass of (3E)-1,1,1,2,2,3,4,5,6,6,7,7,7-tridecafluoro-5-methoxyhept-3-ene and (2E)-1,1,1,2,3,4,5,5,6,6,7,7,7-tridecafluoro-4-methoxyhept-2-ene and (3E)-1,1,1,2,2,4,5,5,6,6,7,7,7-tridecafluoro-3-methoxyhept-3-ene

Adsorption / desorption

Administrative data

Endpoint:

adsorption / desorption: screening

Type of information:

experimental study

Adequacy of study:

key study

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2012

Report date:

2012

Materials and methods

Test guideline

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

Remarks:

The study was conducted according to the guideline in effect at the time of study conduct.

GLP compliance:

yes

Type of method:

HPLC estimation method

Media:

soil/sewage sludge

Test material

Test material information

Constituent 1

Reference substance name:

(2E)-1,1,1,2,3,4,5,5,6,6,7,7,7-tridecafluoro-4-methoxyhept-2-ene; (3E)-1,1,1,2,2,3,4,5,6,6,7,7,7-tridecafluoro-5-methoxyhept-3-ene; (3E)-1,1,1,2,2,4,5,5,6,6,7,7,7-tridecafluoro-3-methoxyhept-3-ene

EC Number:

700-755-2

Molecular formula:

C8H3F13O

IUPAC Name:

(2E)-1,1,1,2,3,4,5,5,6,6,7,7,7-tridecafluoro-4-methoxyhept-2-ene; (3E)-1,1,1,2,2,3,4,5,6,6,7,7,7-tridecafluoro-5-methoxyhept-3-ene; (3E)-1,1,1,2,2,4,5,5,6,6,7,7,7-tridecafluoro-3-methoxyhept-3-ene

Details on test material:

- Purity: 99.3%

Radiolabelling:

no

Study design

Test temperature:

Column Temperature: 40°C

HPLC method

Details on study design: HPLC method:

The reference standards used included acetanilide, benzamide, 4-nitrobenzamide, aniline, 2,5-dichloroaniline, benzoic acid phenyl ester (BAPE), phenanthrene, and dichlorodiphenyltrichloroethane (DDT). Urea was employed as a reference standard for the determination of chromatographic dwell time (t0). All reference standards were stored at normal room temperature.

Stock solutions of each reference standard were prepared by dissolving the individual reference standard in methanol. Aliquots of the stock solutions were diluted in methanol:water 55%:45% to prepare individual reference standard solutions and 3 reference standard mixtures, each containing 3 reference standards. Combinations of reference standards in the reference standard mixtures were determined to minimize interferences based on chromatographic retention. The size of the aliquot from each stock solution was determined to provide adequate peak height for detection and determination of retention time of each component. A stock solution of the test substance was prepared in methanol and further diluted with methanol:water 55%:45% to obtain a test substance solution at a concentration appropriate for detection and determination of its retention time.

Each individual reference standard solution was injected singly to establish the retention time for the specific reference substance. Each reference standard mixture was injected in triplicate, prior to and after injection of the test substance matrix blank (methanol: water 59%:41%) and the test substance solution, to establish retention times for the specific substances for use in the Koc determination. Both the test substance solution and the test substance matrix blank were injected in triplicate to determine the retention times for the test substance by high performance chromatography employing a commercial chromatographic column packed with a cyanopropyl stationary phase.

The following instrument conditions were used:
LC Instrument: Agilent 1100 HPLC
Software: ChemStation software
Column: Agilent Zorbax SB-CN 2.1 x 100 mm with 3.5 µm particle size
Mobile Phase: A: 55% methanol/45% HPLC grade water; B: not used
HPLC Isocratic conditions : Time: 0 minutes; A: 100.0%; B: 0.00%; Time: 20 minutes; A: 100.0%; B: 0.00%
Flow Rate: 0.250 mL/min
Column Temperature: 40°C
Injection Volume: 5.0 µL
Detector: Diode Array: Wavelenght = 201 nm; Bandwith = 8 nm
Stop Time: 20 min

The capacity factor, k’, was calculated for each reference standard and the test substance based on its retention time (tr) and the dwell time for the chromatographic system (t0) employing urea as an unretained compound using the following equation:

k’ =(tr – t0)/t0

Correlation plots were generated by plotting the log k’ value for each reference standard versus the reference log Koc values for soil or sewage sludge for each compound. The best fit correlation equations were generated by linear regression employing reference log Koc data for soil and sewage sludge.

Stable retention times were observed for all reference standards prior to and after analysis of the test solution indicating stable chromatographic operation throughout the study.

The log k’ value for the test substance was employed, along wit the slope and intercept from the equation for the correlation plot to determine log Koc for the test substance using the following equation:

Log Koc (test substance) = (Log k’(test substance) – intercept)/slope

Results and discussion

Adsorption coefficient

Adsorption coefficient 1

Type:

log Koc

Value:

4.43

Temp.:

40 °C

Remarks on result:

other: sewage sludge

Adsorption coefficient 2

Type:

log Koc

Value:

4.5

Temp.:

40 °C

Remarks on result:

other: soil

Results: HPLC method

Details on results (HPLC method):

Average retention times for the reference substances were 1.11 min for urea, 1.47 min for acetanilide, 1.33 min for benzamide, 1.44 min for 4-nitrobenzamide, 1.44 min for aniline, 2.09 min for 2,5-dichloroaniline, 2.91 min for BAPE, 4.69 min for phenanthrene, and 11.7 min for DDT.

Chromatographic analysis of the test substance resulted in a single major chromatographic peak at a mean retention time of 5.71 minutes. Chromatographic resolution of the isomers is not expected under the conditions of the Koc determination. A minor peak, also attributable to the test substance, eluted at 2.77 minutes with an average peak area percent of 3.82% based on peak areas attributable to the test substance. This peak is treated as an impurity in the test substance for this study and no Koc value is reported.

Applicant's summary and conclusion

Validity criteria fulfilled:

yes

Remarks:

This study and the conclusions which are drawn from it fulfill the quality criteria (validity, reliability, repeatability).

Conclusions:

log Koc for sewage sludge was 4.43
log Koc for soil was 4.50

Executive summary:

A study was undertaken to provide data with respect to the adsorption coefficient (K_oc) on soil and sludge for the test substance. Results generated in the study are based on the correlation between the K_oc on soil or sludge and retention time by high-performance liquid chromatography employing a cyanopropyl stationary phase. Employing the correlation data for reference standards and the log k’ value for the primary chromatographic peak related to the test substance, a K_oc value of 31600 (log K_oc = 4.50) was obtained for the test substance on soil. A K_oc value for 26900 (log K_oc = 4.43) was obtained for the test substance on sewage sludge.