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Partition coefficient

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Endpoint:
partition coefficient
Type of information:
experimental study
Adequacy of study:
key study
Study period:
From June 02, 2012 to August 21, 2012
Reliability:
1 (reliable without restriction)
Rationale for reliability incl. deficiencies:
guideline study
Qualifier:
according to
Guideline:
EU Method A.8 (Partition Coefficient)
Deviations:
no
Qualifier:
according to
Guideline:
EPA OPPTS 830.7570 (Partition Coefficient, n-octanol / H2O, Estimation by Liquid Chromatography)
Deviations:
no
GLP compliance:
yes
Remarks:
(OECD GLP)
Type of method:
other: Estimation method using the n-octanol solubility of the test substance and the critical micelle concentration
Partition coefficient type:
octanol-water
Key result
Type:
Pow
Partition coefficient:
> 1 000 000
Temp.:
20 °C
Remarks on result:
other: pH was not reported
Key result
Type:
log Pow
Partition coefficient:
> 6
Temp.:
20 °C
Remarks on result:
other: pH was not reported
Details on results:
After the stirring period, the test sample was clear and no undissolved test substance was observed. From this, it was concluded that the n-octanol solubility of C18-unsatd, diethanolamide at 20°C was > 1x103 g/L.

The Pow, calculated as the quotient of the n-octanol- and critical micelle concentration, is > 1x106. It corresponds with a log Pow value of > 6.
Conclusions:
Under the conditions of the study, the partition coefficient of the test substance was determined to be 1x10E6 at 20°C. This corresponds to a log Pow value of >6.
Executive summary:

A study was conducted to determine the partition coefficient of the test substance using an estimation method based on the n-octanol solubility and the critical micelle concentration according to EU and US EPA guidelines. Under the conditions of the study, the partition coefficient was determined to be 1x10E6 at 20°C. This corresponds to a log Pow value of >6 (Baltussen, 2017).

Endpoint:
partition coefficient
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
key study
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:
Data estimated by KOWWIN v 1.68 (EPIWEB v 4.1) which uses a valid estimation method; the test substance was found to fall in the applicability domain of this method and results are adequate for the purpose of classification and labeling and/or risk assessment.
Qualifier:
according to
Guideline:
other: REACH guidance on QSARs: Chapter R.6. QSARs and grouping of chemicals
Principles of method if other than guideline:
The logarithmic octanol-water partition coefficient (log Kow) was estimated by using KOWWIN v1.68 program of EPIWEB v 4.1.
Initially, using the KOWWIN v1.68 program, the values of the Kow was calculated for the individual components. The value of the Kow for amides, C18 (unsatd.), N,N-bis(hydroxyethyl) was finally calculated on a weighted-average basis using the mole fractions of the individual components.
Partition coefficient type:
octanol-water
Key result
Type:
log Pow
Partition coefficient:
5.51
Remarks on result:
other: weighted avergae value estimated using KOWWIN v.1.68 program of EPIWEB v.4.1
Details on results:
RESULT DETAILS:
1. C16: N,N-bis(hydroxyethyl) hexadecanamide

SMILES : O=C(N(CCO)CCO)CCCCCCCCCCCCCCC
MOL FOR: C20 H41 N1 O3
MOL WT : 343.55
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 1 | -CH3 [aliphatic carbon] | 0.5473 | 0.5473
Frag | 18 | -CH2- [aliphatic carbon] | 0.4911 | 8.8398
Frag | 2 | -OH [hydroxy, aliphatic attach] |-1.4086 | -2.8172
Frag | 1 | -N< [aliphatic attach] |-1.8323 | -1.8323
Frag | 1 | -C(=O)N [aliphatic attach] |-0.5236 | -0.5236
Factor| 1 | Multi-alcohol correction | 0.4064 | 0.4064
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 4.8494
2. C18: N,N-bis(hydroxyethyl) octadecanamide

SMILES : O=C(N(CCO)CCO)CCCCCCCCCCCCCCCCC
MOL FOR: C22 H45 N1 O3
MOL WT : 371.61
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 1 | -CH3 [aliphatic carbon] | 0.5473 | 0.5473
Frag | 20 | -CH2- [aliphatic carbon] | 0.4911 | 9.8220
Frag | 2 | -OH [hydroxy, aliphatic attach] |-1.4086 | -2.8172
Frag | 1 | -N< [aliphatic attach] |-1.8323 | -1.8323
Frag | 1 | -C(=O)N [aliphatic attach] |-0.5236 | -0.5236
Factor| 1 | Multi-alcohol correction | 0.4064 | 0.4064
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 5.8316
3. C18’: N,N-bis(hydroxyethyl) 9-octadecenamide

SMILES : O=C(N(CCO)CCO)CCCCCCCC=CCCCCCCCC
MOL FOR: C22 H43 N1 O3
MOL WT : 369.59
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 1 | -CH3 [aliphatic carbon] | 0.5473 | 0.5473
Frag | 18 | -CH2- [aliphatic carbon] | 0.4911 | 8.8398
Frag | 2 | =CH- or =C< [olefinc carbon] | 0.3836 | 0.7672
Frag | 2 | -OH [hydroxy, aliphatic attach] |-1.4086 | -2.8172
Frag | 1 | -N< [aliphatic attach] |-1.8323 | -1.8323
Frag | 1 | -C(=O)N [aliphatic attach] |-0.5236 | -0.5236
Factor| 1 | Multi-alcohol correction | 0.4064 | 0.4064
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 5.6166
4. C18’’: N,N-bis(hydroxyethyl) 3,9-octadecenamide

SMILES : O=C(N(CCO)CCO)CC=CCCCCC=CCCCCCCCC
MOL FOR: C22 H41 N1 O3
MOL WT : 367.58
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 1 | -CH3 [aliphatic carbon] | 0.5473 | 0.5473
Frag | 16 | -CH2- [aliphatic carbon] | 0.4911 | 7.8576
Frag | 4 | =CH- or =C< [olefinc carbon] | 0.3836 | 1.5344
Frag | 2 | -OH [hydroxy, aliphatic attach] |-1.4086 | -2.8172
Frag | 1 | -N< [aliphatic attach] |-1.8323 | -1.8323
Frag | 1 | -C(=O)N [aliphatic attach] |-0.5236 | -0.5236
Factor| 1 | Multi-alcohol correction | 0.4064 | 0.4064
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 5.4016
5. C18’’’: N,N-bis(hydroxyethyl) 3,9,11-octadecenamide

SMILES : O=C(N(CCO)CCO)CC=CCCCCC=CC=CCCCCCC
MOL FOR: C22 H39 N1 O3
MOL WT : 365.56
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 1 | -CH3 [aliphatic carbon] | 0.5473 | 0.5473
Frag | 14 | -CH2- [aliphatic carbon] | 0.4911 | 6.8754
Frag | 6 | =CH- or =C< [olefinc carbon] | 0.3836 | 2.3016
Frag | 2 | -OH [hydroxy, aliphatic attach] |-1.4086 | -2.8172
Frag | 1 | -N< [aliphatic attach] |-1.8323 | -1.8323
Frag | 1 | -C(=O)N [aliphatic attach] |-0.5236 | -0.5236
Factor| 1 | Multi-alcohol correction | 0.4064 | 0.4064
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 5.1866
6. C20: N,N-bis(hydroxyethyl) eicosanamide

SMILES : O=C(N(CCO)CCO)CCCCCCCCCCCCCCCCCCC
MOL FOR: C24 H49 N1 O3
MOL WT : 399.66
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 1 | -CH3 [aliphatic carbon] | 0.5473 | 0.5473
Frag | 22 | -CH2- [aliphatic carbon] | 0.4911 | 10.8042
Frag | 2 | -OH [hydroxy, aliphatic attach] |-1.4086 | -2.8172
Frag | 1 | -N< [aliphatic attach] |-1.8323 | -1.8323
Frag | 1 | -C(=O)N [aliphatic attach] |-0.5236 | -0.5236
Factor| 1 | Multi-alcohol correction | 0.4064 | 0.4064
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 6.8138
7. C22: N,N-bis(hydroxyethyl) docosanamide

SMILES : O=C(N(CCO)CCO)CCCCCCCCCCCCCCCCCCCCC
MOL FOR: C26 H53 N1 O3
MOL WT : 427.72
-------+-----+--------------------------------------------+---------+--------
TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE
-------+-----+--------------------------------------------+---------+--------
Frag | 1 | -CH3 [aliphatic carbon] | 0.5473 | 0.5473
Frag | 24 | -CH2- [aliphatic carbon] | 0.4911 | 11.7864
Frag | 2 | -OH [hydroxy, aliphatic attach] |-1.4086 | -2.8172
Frag | 1 | -N< [aliphatic attach] |-1.8323 | -1.8323
Frag | 1 | -C(=O)N [aliphatic attach] |-0.5236 | -0.5236
Factor| 1 | Multi-alcohol correction | 0.4064 | 0.4064
Const | | Equation Constant | | 0.2290
-------+-----+--------------------------------------------+---------+--------
Log Kow = 7.7960

Calculation Details

Alkyl chain

Mass fraction (mi)

Molecular weight (Mi, g/mol)

mi/Mi

Mole fraction Xi = (mi/Mi)/Σ(mi/Mi)

Estimated log Kow (Estimated from KOWWIN v 1.68)

log Kow of mole fraction (log Kow x Xi)

C16

0.04

343.55

0.000116431

4.29E-02

4.85

2.08E-01

C18

0.02

371.61

5.38199E-05

1.98E-02

5.83

1.16E-01

C18'

0.40

369.59

0.00108228

3.99E-01

5.62

2.24E+00

C18’'

0.38

367.58

0.001033789

3.81E-01

5.4

2.06E+00

C18’’'

0.12

365.56

0.000328263

1.21E-01

5.19

6.28E-01

C20

0.02

399.66

5.00425E-05

1.85E-02

6.81

1.26E-01

C22

0.02

427.72

4.67596E-05

1.72E-02

7.8

1.35E-01

 

∑1.00

 

∑0.002711386

∑1.00E+00

 

∑5.51

Conclusions:
The weighted average estimated log Kow was determined to be 5.51.
Executive summary:

The octanol-water partition coefficient of the test substance was estimated using the KOWWIN v 1.68 program of EPIWEB v 4.1. Using SMILES as the input parameter, the log Kow was calculated for the individual components. The overall log Kow value was calculated on a weighted-average basis using the mole fractions of the components. The weighted average estimated log Kow was 5.51 (US EPA, 2012).

Description of key information

A partition coefficient (log Kow)  > 6 was determined based on the n-octanol solubility and the critical micelle concentration according to EU Method A.8 and US Guideline EPA 830.7570 (Baltussen, 2017). A log Kow of 5.51 was estimated using the KOWWIN v 1.68 program of EPIWEB v 4.1 (US EPA, 2012). Unlike the experimental measurement technique, which is confounded by surface-activity or presence of other co-solutes, the calculation method generates a theoretical value of log Kow for single representative structures. Considering the potential errors associated with the experimental measurement and estimation in this case, the calculated value of log Kow has been judged to provide the most accurate and reliable value and will therefore be further used in this chemical safety assessment. 

Key value for chemical safety assessment

Log Kow (Log Pow):
5.51
at the temperature of:
20 °C

Additional information