Reaction products of 1H-Imidazole-1-ethanol, 4,5-dihydro-, 2-(C7-C9 odd-numbered alkyl) derivs. and sodium hydroxide and chloroacetic acid

Partition coefficient

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

partition coefficient

Type of information:

read-across from supporting substance (structural analogue or surrogate)

Adequacy of study:

key study

Justification for type of information:

The rationale to read across the data is attached in Section 13.

Reason / purpose for cross-reference:

read-across source

Type:

log Pow

Remarks on result:

other: See below

Details on results:

The water solubility of the substance at 20°C: > 1 x 10^3 g solids/L. The n-octanol solubility of the substance at 20°C: < 82 mg solids/L based on visual determination. Analysis however showed that at a nominal concentration of 530 mg solids/L, the surfactant part of the test substance still completely dissolved at the concentration of 408 mg/L

It is not considered possible to calculate a reliable estimate for the partition coefficient.

Conclusions:

It is not considered possible to calculate a reliable estimate for the partition coefficient with the estimation method.

Reference 2

Endpoint:

partition coefficient

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Study period:

28 Feb 2018 and 13 Apr 2018

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

results derived from a valid (Q)SAR model and falling into its applicability domain, with adequate and reliable documentation / justification

Justification for type of information:

REWOTERIC AM V is a multi-component mixture, the octanol/water partition coefficients of the components of REWOTERIC AM V are estimated using an accepted QSAR.

Qualifier:

no guideline available

Principles of method if other than guideline:

REWOTERIC AM V is a multi-component mixture, the octanol/water partition coefficients of the components of REWOTERIC AM V are estimated using an accepted QSAR.

GLP compliance:

no

Type of method:

other: See reamrk

Remarks:

QSAR estimation.

Partition coefficient type:

other: QSAR estimation

Key result

Type:

log Pow

Partition coefficient:

2.14

Temp.:

20 °C

pH:

7

Remarks on result:

other: See remark

Remarks:

This value is the highest estimate obtained for any of the 3 algorithms with ACD/Percepta for the neutral acid of N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) amino] ethyl] glycinate

Key result

Type:

log Pow

Partition coefficient:

3.21

Temp.:

20 °C

pH:

7

Remarks on result:

other: See remark.

Remarks:

This value is the highest estimate obtained for any of the 3 algorithms with ACD/Percepta for the neutral acid of N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) amino] ethyl] glycinate

Key result

Type:

log Pow

Partition coefficient:

2.25

Temp.:

20 °C

pH:

7

Remarks on result:

other: See remark

Remarks:

This value is the highest estimate obtained for any of the 3 algorithms with ACD/Percepta for N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) ethyl] amine

Key result

Type:

log Pow

Partition coefficient:

3.43

Temp.:

20 °C

pH:

7

Remarks on result:

other: See remark.

Remarks:

This value is the highest estimate obtained for any of the 3 algorithms with ACD/Percepta for N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) ethyl] amine.

Key result

Type:

log Pow

Partition coefficient:

-1

Temp.:

20 °C

pH:

7

Remarks on result:

other: See remark.

Remarks:

This value is the highest estimate obtained for any of the 3 algorithms with ACD/Percepta for (Hydroxyethyl)-N-(aminoethyl) glycinate

Key result

Type:

log Pow

Partition coefficient:

-0.78

Temp.:

20 °C

pH:

7

Remarks on result:

other: See remark

Remarks:

This value is the highest estimate obtained for any of the 3 algorithms with ACD/Percepta for Glycolic acid

Key result

Type:

log Pow

Partition coefficient:

1.91

Temp.:

20 °C

pH:

7

Remarks on result:

other:

Remarks:

This value is the highest estimate obtained for any of the 3 algorithms with ACD/Percepta for N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxooctyl]-2-aminoethyl) glycinate

Key result

Type:

log Pow

Partition coefficient:

2.98

Temp.:

20 °C

pH:

7

Remarks on result:

other: See remark.

Remarks:

This value is the highest estimate obtained for any of the 3 algorithms with ACD/Percepta for N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxodecyl]-2-aminoethyl) glycinate.

Details on results:

Please refer to "Any other information on results incl. tables".

The Table below provides the QSAR estimates for each of the three algorithms within ACD/Percepta for all organic components with the two main alkyl chains in REWOTERIC AM V. For references to Figures 1-6 mentioned in Table 1, please refer to the attached background material. The estimated logPow (highest value for any of the 3 algorithms within ACD/Percepta) are as follows:

N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) amino] ethyl] glycinate: logPow = 2.14

N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) amino] ethyl] glycinate: logPow = 3.21

N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) ethyl] amine: logPow = 2.25

N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) ethyl] amine: logPow = 3.43

(Hydroxyethyl)-N-(aminoethyl) glycinate: logPow = -1.00

Glycolic acid: logPow = -0.78

N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxooctyl]-2-aminoethyl) glycinate: logPow = 1.91

N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxodecyl]-2-aminoethyl) glycinate: logPow = 2.98

 

Table 1: Estimates for logPow of organic components in REWOTERIC AM V for each of the three algorithms within ACD/Percepta

Substance	LogP / Classic	LogP / Gals	Consensu LogP	Concentration water-free %
N-(2-hydroxyethyl)-N-[2-[(1- oxooctyl) amino] ethyl] glycinate (corresponding neutral acid: fig. 1)	2.14 ± 0.46	1.92	2.00	~59
N-(2-hydroxyethyl)-N-[2-[(1- oxodecyl) amino] ethyl] glycinate (corresponding neutral acid: fig. 2)	3.21 ± 0.46	3.17	3.19
N-(2-hydroxyethyl)-N-[2-[(1- oxooctyl) ethyl] amine(fig. 3)	1.40 ± 0.38	2.25	1.99	~6
N-(2-hydroxyethyl)-N-[2-[(1- oxodecyl) ethyl] amine	2.46 ± 0.38	3.43	3.16
(Hydroxyethyl)-N-(aminoethyl) glycinate(fig. 4)	-1.00±0.56	-1.55	-1.32	~4
Glycolic acid*(fig. 5)	-1.05±0.27	-0.78	-0.85	~4
N-Carboxymethyl-(N’-[2- hydroxyethyl]-N’-(1-oxooctyl]-2- aminoethyl) glycinate (fig. 6)	1.91 ± 0.50	1.63	1.75	~1
N-Carboxymethyl-(N’-[2- hydroxyethyl]-N’-(1-oxodecyl]-2- aminoethyl) glycinate	2.98 ± 0.50	2.85	2.90

Note: For references to Figures 1-6 please refer to the attached background material.

*References: Collander, R.; Acta Chem. Scand. 1951, 5, 774: logP: -1.11

Conclusions:

QSAR estimates for each of the three algorithms within ACD/Percepta for log Pow were obtained for all organic components with the two main alkyl chains in REWOTERIC AM V. The estimated logPow (highest value for any of the 3 algorithms within ACD/Percepta) are as follows:
N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) amino] ethyl] glycinate: logPow = 2.14
N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) amino] ethyl] glycinate: logPow = 3.21
N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) ethyl] amine: logPow = 2.25
N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) ethyl] amine: logPow = 3.43
(Hydroxyethyl)-N-(aminoethyl) glycinate: logPow = -1.00
Glycolic acid: logPow = -0.78
N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxooctyl]-2-aminoethyl) glycinate: logPow = 1.91
N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxodecyl]-2-aminoethyl) glycinate: logPow = 2.98

Executive summary:

QSAR estimates of LogPow for each of the three algorithms within ACD/Percepta were obtained for all organic components with the two main alkyl chains in REWOTERIC AM V. The estimated logPow (highest value for any of the 3 algorithms within ACD/Percepta) are as follows:

N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) amino] ethyl] glycinate: logPow = 2.14

N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) amino] ethyl] glycinate: logPow = 3.21

N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) ethyl] amine: logPow = 2.25

N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) ethyl] amine: logPow = 3.43

(Hydroxyethyl)-N-(aminoethyl) glycinate: logPow = -1.00

Glycolic acid: logPow = -0.78

N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxooctyl]-2-aminoethyl) glycinate: logPow = 1.91

N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxodecyl]-2-aminoethyl) glycinate: logPow = 2.98

Description of key information

Because of its extreme solubility in water, its lower solubility in octanol and because it is technically not possible to measure the logKow, it is considered justified to take a pragmatic approach for this substance and to derive a log Kow of -1 to use for the CSA, by concluding that it is assumed that the water solubility of the substance is 10 times higher than its n-octanol solubility. This log Kow of -1 is supported by a calculated log Kow  of –0.64 to -4.19 for a group of constituents obtained with KOWWIN.

Key value for chemical safety assessment

Log Kow (Log Pow):

3

at the temperature of:

20 °C

Additional information

As the substance is a UVCB, containing numerous surface active constituents and NaCl, it is expected that NaCl and the different surfactant constituents will behave differently in water and in octanol. So the standard test methods are not appropriate to measure the log Kow. It was considered justified to study the Kow by the estimation method, as all other methods were assessed to be not adequate; review of available methods:

HPLC method:

-Not suitable for surfactants and for switterionic substances

Flask method:

-Not suitable for surface active substances

-Not suitable for substances with many constituents

-Quantitative determination of the substance concentration in water and octanol is not possible

Calculation method:

-Not suitable as calculations are not possible for all constituents

-Not suitable for substances with many constituents, leading to a broad range with limited use

-Not suitable for salts

-Unreliable as it was shown that different calculation methods gave different results

Slow stirring method:

-Not suitable for substances with many constituents

-Quantitative determination of the substance concentration in water and octanol is not possible

Estimation method:

The estimation method is another alternative method cited in the guidance: Guidance on information requirements and chemical safety assessment -Chapter R.7a: Endpoint specific guidance. The estimation method is based on a separate measurement of the solubility in water and in octanol followed by the ratio of these measurements to estimate the Kow: Kow = [n-octanol] / [water]. On the basis of the conducted solubility tests in water and in octanol with the substance it was shown that:

-The water solubility of the substance is extremely high (>1000 g solids /L)

- The n-octanol solubility of the substance at 20°C is < 82 mg solids/L based on visual estimation (while surfactant constituents of the substance were found dissolved) (concluded based on results of analogues).

-The different constituents of the substance dissolve at different concentrations in n-octanol.

Also with the estimation method it is concluded that it is technically not possible to determine a reliable estimate of the log Kow for this complex and variable substance. Nevertheless the solubility in water was measured to be more than 1000000 mg/L and the solubility in octanol less than 82 mg/l (concluded based on results of analogues).

Owing to the relatively large hydrophilic part (amidoamine glycinate function), and the fact that the surfactant fraction is always under ionized form and in particular as a sodium salt form as manufactured, the solubility of the surfactant fraction in water was found to be very high and clearly above the solubility in n-octanol in the screening estimate.

Because of its extreme solubility in water, its lower solubility in octanol and because it is technically not possible to measure the logKow, it is considered justified to take a pragmatic approach for this substance and to derive a log Kow of -1 for the CSA, by concluding that it is pragmatically assumed that the water solubility of the substance is 10 times higher than its n-octanol solubility.

For difficult substances it is recommended to compare measured values with a calculated value. Therefore the log Kow for various potential constituents of the surfactant fraction was also calculated using the KOWWIN Program (v1.67) in the US EPA 2009 Estimation Programs Interface (EPI) SuiteTM for Microsoft® Windows, version 4.00. For this estimation the Nacl constituent was not taken into account. QSAR estimates of LogPow for each of the three algorithms within ACD/Percepta were obtained for all organic components with the two main alkyl chains in REWOTERIC AM V. The estimated logPow (highest value for any of the 3 algorithms within ACD/Percepta) are as follows:

N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) amino] ethyl] glycinate: logPow = 2.14

N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) amino] ethyl] glycinate: logPow = 3.21

N-(2-hydroxyethyl)-N-[2-[(1-oxooctyl) ethyl] amine: logPow = 2.25

N-(2-hydroxyethyl)-N-[2-[(1-oxodecyl) ethyl] amine: logPow = 3.43

(Hydroxyethyl)-N-(aminoethyl) glycinate: logPow = -1.00

Glycolic acid: logPow = -0.78

N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxooctyl]-2-aminoethyl) glycinate: logPow = 1.91

N-Carboxymethyl-(N’-[2-hydroxyethyl]-N’-(1-oxodecyl]-2-aminoethyl) glycinate: logPow = 2.98

Based on the complex and not totally defined composition of the substance which contains variable chain lengths with a higher proportion of C8 and C10 derivatives and a high concentration of NaCl and taking into account the tensio-active properties of the surfactant fraction and the fact that classical methods cannot be used, it is reasonable to assume a log Kow value of 3. This log Kow of 3 is justified on the basis of the experimental determined solubilities in water and in octanol, and on the basis of the calculated log Kow of 1.91 to 3.43 for the main part of the surfactant fraction obtained with KOWWIN.