Benzenamine, 3,3'-[[1,1'-biphenyl]-4,4'-diylbis(oxy)]bis-

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:

other: The test followed the guidelines given in EU Method C.19 and OECD Method 121 with no deviation.

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2008

Report date:

2008

Materials and methods

Test guideline

Test guideline 1

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

Test guideline 2

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:

The Department of Health of the Government of the United Kingdom

Type of method:

HPLC estimation method

Media:

soil

Test material

Test material information

Constituent 1

Reference substance name:

3-{[4'-(3-aminophenoxy)-[1,1'-biphenyl]-4-yl]oxy}aniline

EC Number:

700-102-1

Cas Number:

105112-76-3

Molecular formula:

C24H20N2O2

IUPAC Name:

3-{[4'-(3-aminophenoxy)-[1,1'-biphenyl]-4-yl]oxy}aniline

Details on test material:

- Name of test material (as cited in study report): 3,3-(4,4-biphenylendioxy)dianiline
- Physical state: Off-white powder
- Analytical purity: > 99 %
- Lot/batch No.: 20070501
- Expiration date of the lot/batch: 30 April 2008
- Storage condition of test material: Room temperature
- Other: Date of receipt 28 August 2007

Study design

Test temperature:

25 °C

HPLC method

Details on study design: HPLC method:

EQUIPMENT
- Apparatus: HPLC
- Type: Hewlett Packard 1050 Liquid Chromatograph
- Type, material and dimension of analytical (guard) column: Hypersil CPS (25cm x 4.6 mm internal diameter)
- Detection system: UV set at 210 nm


MOBILE PHASES
- Type: Methanol:buffer solution (55:45 v/v), where phosphate and borate buffer solutions were employed for th pH 3 and pH 9 tests respectively
- Experiments with additives carried out on separate columns: no
- pH: 3 and 9
- 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: 52 mg/L in HPLC mobile phase containing also formamide with a concentration of 259 mg/L
- Quantity of reference substances: Acetanilide (13.1 mg/L), Nitrobenzene (15.0 mg/L), Naphthalene (4.35 mg/L), 2-Methylnaphthalene (5.37 mg/L), Anthracene (11.8 mg/L), DDT (13.0 mg/L)
- Intervals of calibration: not reported


REPETITIONS
- Number of determinations:
pH 3 test: duplicate bracketed by DDT samples
pH 9 test: duplicate bracketed by reference samples


EVALUATION
- Calculation of capacity factors k': k = (tmeasure - tformamide)/tformamide
- Calculation of retention times: true retention time obtained by subtracting deadtime of internal deadtime standard (formamide) from measured retention time of sample or reference
- Determination of the log Koc value: Interpolation from mean calibration curve given by log10Koc = 3.49log10k + 4.01

Batch equilibrium or other method

Details on sampling:

not applicable

Details on matrix:

not applicable

Details on test conditions:

not applicable

Computational methods:

not applicable

Results and discussion

Adsorption coefficient

Adsorption coefficient 1

Type:

Koc

Value:

251 188

Adsorption coefficient 2

Type:

log Koc

Value:

5.4

Results: HPLC method

Details on results (HPLC method):

- Retention times of reference substances used for calibration: see Table 2
- Details of fitted regression line (log k' vs. log Koc): log10Koc = 3.49log10k + 4.01
- Graph of regression line attached
- Average retention data for test substance: see Table 2

Results: Batch equilibrium or other method

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

Details on results (Batch equilibrium method):

not applicable

Statistics:

not applicable

Any other information on results incl. tables

Table 2: HPLC determination of log10Koc for 3,3-(4,4-biphenylenedioxy)dianiline at pH9

Sample	Substance	tr (min)	k	kog10k	log10Koc
Standard run A	Acetanilide	3.606	0.148	-0.83	1.3
(t0 = 3.141 min)	Nitrobenzene	4.167	0.327	-0.486	2.4
	Naphthalene	5.046	0.606	-0.217	2.8
	2-Methylnaphthalene	5.598	0.782	-0.107	3.9
	Anthracene	7.384	1.351	0.131	4.4
	DDT	11.485	2.656	0.424	5.6
Sample A	Test substance	11.069	2.525	0.402	5.4
(t0 = 3.140 min)
Sample B	Test substance	11.063	2.521	0.402	5.4
(t0 = 3.142 min)
Standard run B	Acetanilide	3.603	0.148	-0.83	1.3
(t0 = 3.139 min)	Nitrobenzene	4.163	0.326	-0.486	2.4
	Naphthalene	5.041	0.606	-0.218	2.8
	2-Methylnaphthalene	5.592	0.781	-0.107	3.9
	Anthracene	7.374	1.349	0.13	4.4
	DDT	11.461	2.651	0.423	5.6

Applicant's summary and conclusion

Validity criteria fulfilled:

yes

Conclusions:

The test substance 3,3-(4,4-biphenylenedioxy)dianiline was found to have log10Koc values of greater 5.6 at pH 3 (highest value for DDT, test substance had higher retention time) and of 5.4 at pH 9.

Executive summary:

The sorption behaviour of 3,3'-[biphenyl-4,4'-diylbis(oxy)]dianiline was tested with the HPLC method according to OECD Guideline No. 121 (Sydney et al. 2008). The tests were performed at pH 3 and pH 9 conditions. Such conditions were obtained by using methanol:buffer solutions (55:45% v/v) as the mobile phase in HPLC, where phosphate and borate buffer solutions were employed for the pH 3 and pH 9 tests, respectively. A limit test was performed only at pH 3 as initial testing had indicated that the retention time of the test substance was greater than that of the highest available reference material, DDT. Thus, it was indicated that the log10 KOC value was greater than 5.6 at pH 3. The adsorption coefficient of the test substance at pH 9 was determined from the capacity factor k by interpolation from the mean calibration curve obtained with an inert deadtime standard (formamide) and six reference substances with known log10 KOC values. A value for the log10 KOC for 3,3'-[biphenyl-4,4'-diylbis(oxy)]dianiline of 5.4 at pH 9 was obtained from the mean calibration curve produced by two tests.