Reaction product of 2-(2-aminoethoxy)ethanol and 2,2',2''-nitrilotriethanol and heptanoic acid and isononanoic acid

Partition coefficient

Administrative data

Endpoint:

partition coefficient

Type of information:

experimental study

Adequacy of study:

key study

Study period:

2018-05-01 to 2018-06-26

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

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:

EU Method A.8 (Partition Coefficient - Shake Flask Method)

Test guideline 2

Qualifier:

according to guideline

Guideline:

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

GLP compliance:

yes (incl. QA statement)

Type of method:

HPLC method

Partition coefficient type:

octanol-water

Test material

Test material information

Constituent 1

Reference substance name:

Reaction product of 2-(2-aminoethoxy)ethanol and 2,2',2''-nitrilotriethanol and heptanoic acid and isononanoic acid

EC Number:

946-979-6

Molecular formula:

N(C2H4OH)3 / NH2(C2H4OC2H4OH) / C6H13COOH / C8H17COOH or N(C2H4OH)3.C6H13COOH / N(C2H4OH)3.C8H17COOH / NH2(C2H4OC2H4OH).C6H13COOH / NH2(C2H4OC2H4OH).C8H17COOH .

IUPAC Name:

Reaction product of 2-(2-aminoethoxy)ethanol and 2,2',2''-nitrilotriethanol and heptanoic acid and isononanoic acid

Test material form:

liquid: viscous

Details on test material:

Test Substance Name: Reaction product of 2-(2-aminoethoxy)ethanol and 2,2',2''-nitrilotriethanol and heptanoic acid and isononanoic acid.
Product Name/Synonym: "Aminseifen".
EG number: 944-618-7.
Batch number: 2018-02 2023-02 03.
Purity of this sample/batchis: ~99,4% (contains ~0,6% water).
Description: liquid, viscous, light yellow up to brown.
Expiry date: February 2023.

Study design

Analytical method:

high-performance liquid chromatography

Results and discussion

Partition coefficient

Key result

Type:

log Pow

Partition coefficient:

>= 0 - <= 2.66

Temp.:

20 °C

Remarks on result:

other: Log Pow = <0 – 2.66 .

Any other information on results incl. tables

Estimation of partition coefficient:

Solvent	Mass of sample (mg)	Solvent volume (ml)	Predicted solubility (g/L)	Log P	Analysis method
Water	> 1010	1	> 1010	Not determined	See comments
Octanol	> 1002	1	> 1002	Not determined	See comments

Estimated log Pow = Not determined.

Comment: As the test item is multi-component, and fully miscible in both water and octanol, testing using the standard shake flask method would not be possible. It was decided to try and determine the partition coefficient for each component using the HPLC method. A calibration graph is generated using the retention time of reference materials with known Log Pow values.

It is recommended that the test materials are run in a non-ionised form. Due to the basic nature of the 2-(2-aminoethoxy)ethanol and the 2,2’,2’’-nitrilotriethanol, it was not possible to use a pH value for the mobile phase that would maintain these products in a nonionised form and not be detrimental to the HPLC column. Consequently the analysis was run using acidic conditions that would allow the acids present to be in a non-ionised form.

At the time of testing it was not possible to obtain a marker for the isononanoic acid. It is thought that given the data obtained, the peak having a retention time of 5.66 minutes possibly corresponds to that of isononanoic acid.

An HPLC method was developed and a calibration curve was generated by plotting the mean Log K value of reference materials against their Log Pow values. The followingreference materials were used:

Retention time: Thiourea 0.87; Acetanilide 1.33; Acetophenone 2.56; Toluene 6.84; Ethyl benzene 11.42; Isopropyl benzene 18.13.

N.B. Thiourea is traditionally used to obtain the retention of a non-retained product.

The retention times were also obtained for the following reference markers:

Retention time: 2-(2-aminoethoxy)ethanol 0.83; 2,2’,2’’-nitrilotriethanol (Triethanolamine) 1.37; heptanoic acid 3.12.

N.B. The retention times for the 2-(2-aminoethoxy)ethanol and 2,2’,2’’-nitrilotriethanol were slightly less than that for the non-retained peak (thiourea). This would imply that the Log Pow values for these products, under acidic conditions, is less than zero. The HPLC partition coefficient method is suitable for Log Pow values in the range 0 to 6.

The following retention times were obtained for the four main peaks in the supplied test material. The Log Pow values were calculated using the calibration curve.

		Retention time	Log Pow
Peak 1	2-(2-aminoethoxy)ethanol and 2,2’,2’’-nitrilotriethanol	0.83	<0
Peak 2	Unknown	1.37	1.00
Peak 3	heptanoic acid	3.12	2.10
Peak 4	Thought to be isononanoic acid	5.66	2.66

In an ideal situation it would be possible to have reference material with known Log Pow values that are similar to the products being tested. However as the test material contains components having both acidic or basic functionalities, this was not possible. Consequently the test was run against neutral materials under acidic conditions. It should be noted that the resultant Log Pow values are only applicable to the test material under acidic conditions.

Applicant's summary and conclusion

Conclusions:

The partition coefficient (log Pow) at 20°C of the test substance is <0 – 2.66.

Executive summary:

Partition coefficient (log Pow, 20°C): <0 – 2.66.