1,4-Benzenediamine, N1-(1,4-dimethylpentyl)-

Adsorption / desorption

Administrative data

Endpoint:

adsorption / desorption

Remarks:

adsorption

Type of information:

experimental study

Adequacy of study:

key study

Study period:

21 May 1996 to 19 August 1996

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

other: GLP study conducted in accordance with a scentifically acceptable method with GLP certificate.

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

1996

Report date:

1996

Materials and methods

Test guideline

Qualifier:

no guideline followed

Principles of method if other than guideline:

The determination was carried out using an HPLC screening method. The procedure employed is that outlined in the draft "HPLC-Screening Method for the Determination of the Adsorption Coefficient on Soil - Comparison of Different Stationary Phases", W Kordel, J Stutte and G Kotthoff, Fraunhofer - Institut fur Umweltchemie and Okotoxikologie.

GLP compliance:

yes (incl. QA statement)

Type of method:

HPLC estimation method

Media:

soil/sewage sludge

Test material

Test material information

Constituent 1

Reference substance name:

N1-(5-methylhexan-2-yl)benzene-1,4-diamine

Cas Number:

63302-43-2

Molecular formula:

C13H22N2

IUPAC Name:

N1-(5-methylhexan-2-yl)benzene-1,4-diamine

Details on test material:

Sponsor's identification: TRAE
Description: Very dark purple solid block
Label: Distilled TRAE Y-775 Jan30, 96 Naugatuck Rhyang
Date received: 22 April 1996

Specific details on test material used for the study:

Details on properties of test surrogate or analogue material (migrated information):
Not applicable

Radiolabelling:

no

Study design

Test temperature:

No data

HPLC method

Details on study design: HPLC method:

Determination of retention time:
The sample, formamide and reference standard solutions were injected in duplicate using the following HPLC parameters:
Column: Zorbax CN (250 x 4.6 mm id)
Mobile phase: pH 4.55 : acetonitrile:0.06M potassium dihydrogen orthophosphate (50:50) adjusted to pH 4.55 using orthophosphoric acid
pH 8.78 : acetonitrile:water (50:50)
Flow rate: 1 ml/min
Injection volume: 25 ul
Wavelength: dead time and references - 210 nm, sample - 240 nm
Temperature: 22 + 2 degrees C

As it was expected that TRAE would show a mode of dissociation, the determination as carried out using mobile phases of varying pH in order to measure the retention of both associated and dissociated species.

Calibration
Organic reference standards were prepared in acetonitrile at the concentrations indicated.

Sample
An aliquot (0.0489 g) of test material was diluted to 100 ml with acetonitrile.

Dead time
The dead time was determined by measuring the retention time of a 224 mg/l solution of formamide (purity 99.5%*).

Construction of calibration curve:
A calibration curve was constructed from the retention time data of the formamide and reference standard solutions. The capacity factors (k), for
the reference standards were calculated.

Adsorption coefficient or sample:
Capacity factors were calculated from the retention time data. Log10 Koc values were then determined with reference to the calibration curves.

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:

271

Remarks on result:

other: At pH = 4.55

Adsorption coefficient 2

Type:

log Koc

Value:

2.43

Remarks on result:

other: At pH = 4.55

Adsorption coefficient 3

Type:

Koc

Value:

8 280

Remarks on result:

other: At pH = 8.78

Adsorption coefficient 4

Type:

log Koc

Value:

3.92

Remarks on result:

other: At pH = 8.78

Results: HPLC method

Details on results (HPLC method):

Dead time
The retention times determined for formamide are shown below:

pH 4.55
Retention time (min) for injection 1 and injection 2 = 2.661. Mean = 2.661

pH 8.78
Retention time (min) for injection 1 = 2.720, for injection 2: 2.723. Mean = 2.722

The retention times obtained for the calibration standards are detailed under any other information below.

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

The calibration curves are attached under background information below.

The retention times obtained for the calibration standards are shown below:

pH 4.55

Standard	Retention time (mins)
	Injection 1	Injection 2	Mean
Simazine	4.540	4.538	4.539
Monolinuron	5.644	5.636	5.640
Propazine	5.707	5.705	5.706
Monuron	4.752	4.752	4.752
Atrazine	5.067	5.054	5.061
Phenamiphos	6.153	6.131	6.142
Baytan	5.636	5.620	5.628
Linuron	6.674	6.662	6.668
Endosulfan alcohol	6.604	6.604	6.604
Disulfoton	10.737	10.695	10.716
Monceren	10.907	10.906	10.907
Fenoxaprop-ethyl	11.204	11.149	11.177
Alpha-endosulfan	12.539	12.514	12.527
Pentachloronitrobenzene	11.78	11.767	11.774
Cyfluthrin	23.325	23.145	23.235

pH 8.78

Standard	Retention time (mins)
	Injection 1	Injection 2	Mean
Simazine	4.451	4.453	4.452
Monolinuron	5.553	5.558	5.556
Propazine	5.603	5.604	5.604
Monuron	4.721	4.721	4.721
Atrazine	4.980	4.985	4.983
Phenamiphos	6.152	6.161	6.157
Baytan	5.637	5.646	5.642
Linuron	6.606	6.612	6.609
Endosulfanalcohol	6.749	6.748	6.749
Disulfoton	10.680	10.707	10.694
Monceren	11.127	11.135	11.131
Fenoxaprop-ethyl	11.378	11.394	11.386
Alpha-endosulfan	12.731	12.753	12.742
Pentachloronitrobenzene	12.081	12.093	12.087
Cyfluthrin	25.165	25.203	25.184

The capacity factors, k, for the above standards were determined from the retention times. The capacity factors are shown in the tables below together with the literature values for Log10 koc.

pH 4.55

Standard	Capacity factor k	Log10k	Log10Koc
Simazine	0.706	-0.151	1.77
Monolinuron	1.120	4.903E-02	1.78
Propazine	1.144	5.854E-02	1.94
Monuron	0.786	-0.105	1.99
Atrazine	0.902	4.492E-02	2.11
Phenamiphos	1.308	0.117	2.27
Baytan	1.115	4.727E-02	2.39
Linuron	1.506	0.178	2.62
Endosulfan-alcohol	1.482	0.171	2.99
Disulfoton	3.027	0.481	3.06
Monceren	3.099	0.491	3.53
Fenoxaprop-ethyl	3.200	0.505	3.87
Alpha-endosulfan	3.707	0.569	4.06
Pentachloronitrobenzene	3.424	0.535	4.29
Cyfluthrin	7.732	0.888	4.53

pH 8.78

Standard	Capacity factor k	Log10k	Log10Koc
Simazine	0.636	-0.197	1.77
Monolinuron	1.041	1.759E-02	1.78
Propazine	1.059	2.489E-02	1.94
Monuron	0.735	-0.134	1.99
Atrazine	0.831	-8.051E-02	2.11
Phenamiphos	1.262	0.101	2.27
Baytan	1.073	3.057E-02	2.39
Linuron	1.428	0.155	2.62
Endosulfan-alcohol	1.480	0.170	2.99
Disulfoton	2.929	0.467	3.06
Monceren	3.090	0.490	3.53
Fenoxaprop-ethyl	3.184	0.503	3.87
Alpha-endosulfan	3.682	0.566	4.06
Pentachloronitrobenzene	3.441	0.537	4.29
Cyfluthrin	8.254	0.917	4.53

Samples

The retention times of the test material are shown in the tables below:

pH 4.55

Injection	Retention time (mins)	Capacity Factor k	Log10k	Log10Koc
1	6.168	1.318	0.120	2.44
2	6.153	1.312	0.118	2.43

Mean Log10 Koc = 2.43

Koc = 271

pH 8.78

Injection	Retention time (mins)	Capacity Factor k	Log10k	Log10Koc
1	12.782	3.697	0.568	3.92
2	12.716	3.672	0.565	3.91

Mean Log10 Koc = 3.92

Koc = 8280

Applicant's summary and conclusion

Validity criteria fulfilled:

not specified

Conclusions:

The soil adsorption coefficient (Koc) values of the test substance are as follows:
pH 4.55: Koc = 271, Log10 Koc = 2.43
pH 8.78: Koc = 8280, Log10 Koc = 3.92

Executive summary:

The soil adsorption coefficient of the test substance was determined using a HPLC screening method.

As it was expected that TRAE would show a mode of dissociation, the determination as carried out using mobile phases of varying pH in order to measure the retention of both associated and dissociated species.

The soil adsorption coefficient (Koc) values of the test substance are as follows:

pH 4.55: Koc = 271, Log10 Koc = 2.43

pH 8.78: Koc = 8280, Log10 Koc = 3.92