1,2-dimethyl-3-propyl imidazolium bis((trifluoromethyl)sulfonyl)amide

Partition coefficient

Administrative data

Endpoint:

partition coefficient

Type of information:

experimental study

Adequacy of study:

key study

Study period:

06. SEP. 2018

Reliability:

1 (reliable without restriction)

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2018

Report date:

2018

Materials and methods

Test guideline

Test guideline 1

Qualifier:

according to guideline

Guideline:

OECD Guideline 117 (Partition Coefficient (n-octanol / water), HPLC Method)

Version / remarks:

13 April 2004

Deviations:

no

Test guideline 2

Qualifier:

according to guideline

Guideline:

other: Method A.24 "Partition Coefficient (N-OCTANOL/WATER), HIGH PERFORMANCE LIQUID CHROMATOGRAPHY (HPLC) METHOD

Version / remarks:

Commission Regulation (EU) 2016/266 of adopted 7 December 2015 amending Regu-lation EC No. 440/2008

Deviations:

no

Test guideline 3

Qualifier:

equivalent or similar to guideline

Guideline:

other: SOP 118 009 30 “Bestimmung des log POW (Verteilungskoeffizient n-Octanol/Wasser) mittels HPLC

Version / remarks:

edition 7 valid from 18. Sep. 2017

Deviations:

no

GLP compliance:

yes (incl. QA statement)

Remarks:

Landesamt für Umwelt Rheinland-Pfalz, Mainz, Germany

Type of method:

HPLC method

Partition coefficient type:

octanol-water

Test material

Test material information

Constituent 1

Reference substance name:

1,2-dimethyl-3-propyl imidazolium bis((trifluoromethyl)sulfonyl)amide

EC Number:

805-807-9

Cas Number:

169051-76-7

Molecular formula:

C10H15F6N3O4S2

IUPAC Name:

1,2-dimethyl-3-propyl imidazolium bis((trifluoromethyl)sulfonyl)amide

Test material form:

liquid

Details on test material:

Appearance : colorless oil
Composition: a base stock containing (C, 28.64; H, 3.61; F, 27.18; N, 10.02; O, 15.26; S, 15.29)
Molecular formula : C10H15F6N3O4S2
Molecular Weight : 419.12 g/mol
Purity >99% (purity determined by MNR)
Homogeneity : homogeneous

Specific details on test material used for the study:

SOURCE OF TEST MATERIAL
Batch no. L 16-0158
Expiry date: 26. Feb. 2030

STABILITY AND STORAGE CONDITIONS OF TEST MATERIAL
Stability : H2O: 96h; EtOH: 96h; acetone: 96h; CH3CN: 96h; DMSO: unknown
Solubility : H2O: > 1 g/L ; EtOH: > 1 g/L; acetone: > 1 g/L; CH3CN: < 0.1 g/L; DMSO: > 1 g/L
Storage : Room Temperature (20 ± 5°C)

TREATMENT OF TEST MATERIAL PRIOR TO TESTING
A solution of the test item was prepared by weighing 20.3 mg 1-Propyl-2,3-Dimethylimidazolium bis(trifluoromethanesulfonyl)imide into a 20 mL flask and filling up to 20.3 mL with the mobile phase. 0.1 mL of this solution were mixed with 0.9 mL mobile phase, resulting in a solution with a concentration of 100 mg/L which was used for the measurements.

Study design

Analytical method:

high-performance liquid chromatography

Results and discussion

Partition coefficient

Key result

Type:

log Pow

Partition coefficient:

ca. 2.369

Temp.:

25 °C

pH:

> 6 - < 7

Any other information on results incl. tables

Reference Items

The values for log k and log Pow of the reference items are presented in the following table:

Compound	log k	log Pow
2-Butanone	-0.6425	0.30
Benzyl alcohol	-0.4854	1.10
Acetophenone	-0.2800	1.70
Nitrobenzene	-0.1601	1.90
Benzene	0.0689	2.10
Toluene	0.2838	2.70
Naphthalene	0.4054	3.60

Dead time is 1.388 ± 0.005 minutes, with RSD (relative standard deviation) 0.383%.

The RSD of the retention times of the reference items lay all below 0.6 %.

Equation of the regression: log k = 0.3545 * log Pow – 0.7944 with a coefficient of determination r²= 0.9421

Test Item1-Propyl-2,3-Dimethylimidazolium bis(trifluoromethanesulfonyl)imide

I) Measurement Data

The retention times (RT) of the test item are presented in the following table:

Measurement	RT 1	RT 2
	min.	min.
Measurement 1	1.229	2.934
Measurement 2	1.229	2.928
Measurement 3	1.231	2.923
Mean	1.229	2.929
Standard Deviation	0.001	0.006

 

 Peak Areas Test Item

Measurement	Area Peak 1	Relative Area Peak 1	Area Peak 2	Relative Area Peak 2
	[mAU*min]	[%]	[mAU*min]	[%]
Measurement 1	1.1216	9.22	11.0454	90.78
Measurement 2	1.1103	9.13	11.0520	90.87
Measurement 3	1.1227	9.09	11.2311	90.91
Mean	1.1182	9.15	11.1095	90.85
Relative Standard Deviation [%]	0.61	0.73	0.95	0.07

 

II) Calculated Values

The calculated values are presented in the following table:

Capacity Factor, log Capacity Factor, log Pow Test Item Peaks

Peak	Measurement No.	k	log k	log Pow
1	1	-0.1148	n.c.*	n.c.*
	2	-0.1147	n.c.*	n.c.*
	3	-0.1134	n.c.*	n.c.*
	Mean	-	-	n.c.*
	Standard Deviation	-	-	n.c.*
2	1	1.1143	0.0470	2.373
	2	1.1099	0.0453	2.368
	3	1.1063	0.0439	2.364
	Mean	-	-	2.369
	Standard Deviation	-	-	0.004

*Not calculable, because k is negative. The retention time of peak 1 is lower than the retention time of thiourea, which was used for the determination of the dead time of the method. The log Pow of this peak is stated as < 0.3.

log Pow was calculated from the capacity factor as follows: log Pow= (log k + 0.7944) / 0.3545

Applicant's summary and conclusion

Conclusions:

Variations in the retention times of reference items and test item were very small, demonstrating a stable configuration of the HPLC column.
The correlation log k / Log Pow is acceptable: the coefficient of determination R2 was calculated as 0.9421. This value was considered as sufficiently high to use the calibration function for the determination of the log POW of the test item 1-Propyl-2,3-Dimethylimidazolium bis(trifluoromethanesulfonyl)imide.
Using the correlation log k / log Pow, the log Pow of the test item was calculated:
For peak 1 the calculation of the log Pow was not possible, because the retention time of the signal lay below the retention time of thiourea. So, the log Pow of peak 1 is stated as <0.3.
For peak 2 the log Pow was calculated as 2.369 ± 0.004.
Therefore, the log Pow of the test item 1-Propyl-2,3-Dimethylimidazolium bis(trifluoromethanesulfonyl)imide is stated of Peak 1 as < 0.3 and of Peak 2 as 2.4 at temperature of 25 ± 0.5 °C and a pH value of 6 - 7.
No observations were made which might cause doubts concerning the validity of the study outcome.

Executive summary:

The study was performed using a HPLC with a C18 column. Seven reference items with different retention times and thiourea for the determination of the dead time were used to produce a calibration curve, since retention time on hydrophobic columns and Pow are correlated. The reference items were chosen on behalf of the pre-test.

One vial was filled with the reference item mix and one vial with the test item solution. The vials were analysed using the HPLC with the program described below. First one injection from the solvent blank methanol/water 75/25 (%v/v) was made. Then three injections were measured from the reference item mix, three injections from the test item and again three injections from the reference item mix.

For each reference item, the capacity factor k was calculated from the retention time of thiourea and the retention time of the respective reference item.

A calibration function (log k versus log Pow, linear fit) was determined using the literature values for Pow of the reference items and the retention times in the six determinations.

The test item solution in mobile phase showed a chromatogram with two peaks.

With the calibration function log k versus log Pow, the corresponding log Pow values of the peaks were determined as:

Peak	Mean Area [mAU*min][1]	Rel. Area %	Mean Retention Time [min]	log Pow ±Stand. Dev
1	1.1182	9.15	1.229	< 0.3*
2	11.1095	90.85	2.929	2.369±0.004

*Not calculable, because K is negative. The retention time of peak 1 is lower than the retention time of thiourea, which was used for the determination of the dead time of the method. The log P_OW of this peak is stated as < 0.3.

 

Therefore, the log Pow of the test item 1-Propyl-2,3-Dimethylimidazolium bis(trifluoromethanesulfonyl)imide is stated of Peak 1 as < 0.3 and of Peak 2 as 2.4 at temperature of 25 ± 0.5 °C and a pH value of 6 - 7.

[1]mAU = milli absorbance units