4-nitrobenzenesulphonyl chloride

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:

2017-11-21 to 2017-11-21

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

Media:

other: HPLC column

Specific details on test material used for the study:

SOURCE OF TEST MATERIAL
- Source and lot/batch No.of test material: M16LB4523
- Expiration date of the lot/batch: 2018-02-09 (retest date)
- Purity test date: 2017-11-29 (certificate of analysis release date)

STABILITY AND STORAGE CONDITIONS OF TEST MATERIAL
- Storage condition of test material: At room temperature

Radiolabelling:

no

Test temperature:

Column temperature 35°C ± 1°C.

Details on study design: HPLC method:

EQUIPMENT
- Apparatus: Acquity UPLC system (Waters, Milford, MA, USA)
- Type: Acquity UPLC TUV detector (Waters)
- Type, material and dimension of analytical (guard) column: Acquity UPLC HSS Cyano, 100 mm x 2.1 mm i.d., dp = 1.8 µm (Waters)
- Detection: 210 nm (UV)
- Column temperature: 35°C ± 1°C

MOBILE PHASES
- Type: 55/45 (v/v) methanol/water
- Solutes for dissolving test and reference substances:
* Solution of the unretained compound:
A 5.0 g/L stock solution of formamide (99.2%, [75-12-7], Alfa Aesar, Karlsruhe, Germany) in methanol was used. The stock solution was diluted to obtain an end solution of 55/45 (v/v) methanol/water.
The formamide blank solution was 55/45 (v/v) methanol/water.
* Reference substance solutions:
Stock solutions of the reference substances at concentrations of approximately 1 g/L in methanol or acetonitrile were used. The stock solutions were diluted to obtain an end solution of 55/45 (v/v) methanol/water.
The blank solution for the mixture of reference substances was 55/45 (v/v) methanol/water.
* Test solution:
A 1000 mg/L stock solution of the test item was prepared in acetonitrile. The stock solution was 100-times diluted to obtain an end solution of 55/45 (v/v) methanol/water. The final concentration of the test item solution was 10.0 mg/L.
The test item blank solution was 55/45 (v/v) methanol/water.
An additional dilution of the stock solution was prepared in acetonitrile at concentration level 50 mg/L, to see whether the peaks determined are test item or its degradation products.

REFERENCE SUBSTANCES
- Identity: combined reference solution containing Acetanilide, Monuron, 2,5-Dichloroaniline, Napthalene, Benzoic acid phenylester, Fenthion, Phenanthrene and 4,4'-DDT

DETERMINATION OF RETENTION TIMES
- Quantity of test substance introduced in the column: 10 mg/L.
- Quantity of reference substances: 1 g/L in methanol or acetonitrile
- Intervals of calibration: no data

REPETITIONS
- Number of determinations: 2 times (test item solution and reference substance), 1 time (blank solution)

EVALUATION
- Calculation of capacity factors k': from retention time of reference items, the test item, and then on-sorbed chemical item
- Determination of the log Koc value: a correlation of log k' versus log Koc of the reference items is plotted using linear regression - the log k' value of the test item is then used to calculate its log Koc value

Key result

Type:

log Koc

Value:

< 1.26 dimensionless

pH:

7

Remarks on result:

other: peak 1 (degradation product)

Key result

Type:

log Koc

Value:

1.83 dimensionless

pH:

7

Remarks on result:

other: peak 2 (degradation product)

Key result

Type:

Koc

Value:

< 18 dimensionless

pH:

7

Remarks on result:

other: peak 1 (degradation product)

Key result

Type:

Koc

Value:

67 dimensionless

pH:

7

Remarks on result:

other: peak 2 (degradation product)

Details on results (HPLC method):

- Retention times (tr,1 and tr,2) of reference substances used for calibration:
* Formamide (t=0):
tr,1: 0.686 min; tr,2: 0.686 min
* Acetanilide:
tr,1: 0.910 min.; tr,2: 0.912 min.
* Monuron:
tr,1: 1.125 min.; tr,2: 1.127 min.
* 2,5-Dichloroaniline:
tr,1: 1.281; tr,2: 1.284 min.
* Naphthalene:
tr,1: 1.495 min.; tr,2: 1.499 min.
* Benzoic acid phenylester:
tr,1: 1.769 min; tr,2: 1.776 min.
* Fenthion:
tr,1: 2.380 min.; tr,2: 2.393 min.
* Phenanthrene:
tr,1: 2.629 min; tr,2: 2.642 min.
* 4,4'-DDT:
tr,1: 6.572 min; tr,2: 6.620 min.

- Details of fitted regression line (log k' vs. log Koc): log k’ = 0.322 x log Koc – 0.818 (r = 0.98, n = 16)
- Average retention data for test substance:
* peak 1: 0.400 min
* peak 2: 1.089 min
- Koc test substance:
* peak 1: < 18
* peak 2: 67

Transformation products:

not measured

Calculation of pK_avalues

As the nitro group could not be correctly defined in Pallas, no calculation result could be reported. .Therefore, the UPLC analysis was performed at neutral pH.

Validity criteria fulfilled:

yes

Conclusions:

The HPLC method using soil-adsorption-reference data was applied for the determination of the adsorption coefficient (Koc) of JNJ-39722280-AAA (4-nitrobenzene-1-sulfonyl chloride).
In the chromatogram of the test solution, two peaks were observed. Comparing it to the chromatogram in acetonitrile, it was concluded that both peaks were degradation products of the test item.
The mean log Koc of the main degradation products of 4-nitrobenzene-1-sulfonyl chloride at neutral pH were determined to be <1.26 and 1.83, peak 1 and peak 2 respectively using the HPLC estimation method according to OECD guideline 121. The results of the test can be considered reliable without restriction.

Description of key information

This endpoint is covered with a GLP-study (Reingruber, 2018) performed according to standard test guideline OECD 121. The mean log Koc of the main degradation products of 4-nitrobenzene-1-sulfonyl chloride were determined to be <1.26 and 1.83, peak 1 and peak 2, respectively, using the HPLC estimation method. The partition coefficients in soil, sediment, suspended matter and raw sewage sludge were calculated from the Koc value and the fraction of organic carbon in the compartment as stipulated in the ECHA guidance Chapter 16 - Table R.16-11.

The log Kow of the second peak (log kow = 1.83) was considered as key value for the safety assessment

Key value for chemical safety assessment

Koc at 20 °C:

67