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Physical & Chemical properties

Water solubility

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Endpoint:
water solubility
Type of information:
(Q)SAR
Adequacy of study:
key study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: Meets generally accepted scientific standards, well documented and acceptable for assessment
Justification for type of information:
QSAR prediction: migrated from IUCLID 5.6
Qualifier:
according to
Guideline:
other: No data
Deviations:
not applicable
Principles of method if other than guideline:
Water Sol from Kow (WSKOW) v 1.41 accessed via Epiweb v 4.0
GLP compliance:
no
Type of method:
other: Prediction
Specific details on test material used for the study:
2-(diphenylphosphino)benzoic acid; CAS: 17261-28-8; SMILES: O=C(O)c(c(P(c(cccc1)c1)c(cccc2)c2)ccc3)c3
Key result
Water solubility:
0.39 mg/L
Conc. based on:
test mat.
Temp.:
25 °C
pH:
7
Remarks on result:
other: QSAR prediction
Water solubility:
1.4 mg/L
Conc. based on:
test mat.
Temp.:
25 °C
pH:
7
Remarks on result:
other: QSAR prediction
Details on results:
Using the US EPA EPIWIN software, the test material was estimated to have a water solubility ranging from 0.39 to 1.4 mg/L at 25°C.

Equation used to make Water Solubility estimates with WSKOWWIN:

Log S (mol/L) = 0.796 - 0.854 log kow - 0.00728 MW + Correction (used when Melting Point NOT available).

Corrections:

Acid, aromatic 0.00

Fragment Description used to make water solubility estimates with WATERNT:

                 Water Sol (v1.01 est): 0.38594 mg/L

 

SMILES : O=C(O)c(c(P(c(cccc1)c1)c(cccc2)c2)ccc3)c3

CHEM  :

MOL FOR: C19 H15 O2 P1

MOL WT : 306.30

-------+-----+--------------------------------------------+----------+---------

 TYPE | NUM |   WATER SOLUBILITY FRAGMENT DESCRIPTION  | COEFF  | VALUE 

-------+-----+--------------------------------------------+----------+---------

 Frag | 14 | Aromatic Carbon (C-H type)              |-0.3359  | -4.7021

 Frag | 1 | -COOH  [acid, aromatic attach]          | 0.0568  | 0.0568

 Frag | 4 | Aromatic Carbon (C-substituent type)    |-0.5400  | -2.1598

 Frag | 1 | >P- [phosphine type]                    | 0.0000  | 0.0000

 Factor| 1 | Ring reaction ->  ortho to aromatic acid | 0.6563  | 0.6563

 Const |    | Equation Constant                        |         | 0.2492

-------+-----+--------------------------------------------+----------+---------

                             Log Water Sol (moles/L) at 25 dec C =  -5.8996

                             Water Solubility (mg/L) at 25 dec C = 0.38594

Conclusions:
Using the US EPA EPIWIN software, the test material was estimated to have a water solubility ranging from 0.39 to 1.4 mg/L at 25°C.

Interpretation of results (migrated information): slightly soluble (0.1-100 mg/L)
Executive summary:

An estimation of the water solubility of 2-(diphenylphosphino)benzoic acid was performed using the specialised chemical estimation software, WSKOWWIN, version 1.42 © 2000 and WATERNT v1.01 developed by the US Environmental Protection Agency (part of the EPISUITE software package). The software was validated with reference substances which had common or similar functional groups present as the test material.

Using the US EPA EPIWIN software, the test material was estimated to have a water solubility ranging from 0.39 to 1.4 mg/L at 25°C.

Endpoint:
water solubility
Type of information:
experimental study
Adequacy of study:
supporting study
Study period:
2018
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
comparable to guideline study with acceptable restrictions
Justification for type of information:
Experimental water solubility study
Qualifier:
equivalent or similar to
Guideline:
OECD Guideline 105 (Water Solubility)
Deviations:
no
Principles of method if other than guideline:
Flask method.

Definitive Test

Two identical Water Accommodated Fractions (WAFs) were prepared for SHOP Ligand at loading rates of 1 and 5 mg/L pre-determined from the preliminary visual observation studies. The WAFs were prepared in 2L conical flasks with glass/PTFE taps at the base and sealed with a ground glass stopper. The sample was dosed into the WAF vessels as follows:

• SHOP Ligand test sample (2 mg and 20 mg) was added directly as a fine powder to the test vessels before adding de-ionised water (2L).

The WAF’s were then stirred under ambient laboratory conditions using a PTFE coated magnetic stirrer at 250 rpm. After stirring periods of 24, 48, 72, 96 and 240 hours the WAFs were left to settle for one hour by stopping the stirring and sub-samples were taken for LC-MS and LC-UV analysis. Sampling of the WAFs was carried out via the sample tap positioned at the base of the conical flask to prevent any contamination of the WAF samples with the test substance. The first 50 ml was discarded. A blank water-only WAF was set-up in parallel. Samples taken from WAFs were analysed with and without centrifugation. Centrifugation was carried out using a 15 ml PP tube with HDPE cap for 15 minutes at a speed of 4400 rpm. After centrifugation 1 ml of sample was removed from the top with a glass pipette and discarded. The sample to be used for LC-MS or LC-UV analysis were taken from the water column in the middle of the PP tube. The bottom fraction of the sample was discarded.
GLP compliance:
no
Other quality assurance:
ISO/IEC 17025 (General requirements for the competence of testing and calibration laboratories)
Type of method:
flask method
Specific details on test material used for the study:
2-(diphenylphosphino)benzoic acid; CAS: 17261-28-8
Water solubility:
ca. 0.39 mg/L
Conc. based on:
test mat. (dissolved fraction)
Loading of aqueous phase:
1 mg/L
Incubation duration:
ca. 240 h
Temp.:
20 °C
pH:
ca. 7
Water solubility:
ca. 1 mg/L
Conc. based on:
test mat. (dissolved fraction)
Loading of aqueous phase:
5 mg/L
Incubation duration:
ca. 240 h
Temp.:
20 °C
pH:
7
Details on results:
Using the OECD 105 flask method (with LC-UV analysis), the water solubility of SHOP Ligand was observed to be in the range of 0.4-1.0 mg/L after stirring for 240h (10d) at a temperature of 20 (±2) °C, which is in excellent agreement with the computational predicted values of 0.39 – 1.4 mg/L using WSKOWWIN and WATERNT models from the US EPA EPISuite software package, respectively.
Conclusions:
Using the OECD 105 flask method (with LC-UV analysis), the water solubility of SHOP Ligand was observed to be in the range of 0.4-1.0 mg/L after stirring for 240h (10d) at a temperature of 20 (±2) °C, which is in excellent agreement with the computational predicted values of 0.39 – 1.4 mg/L using WSKOWWIN and WATERNT models from the US EPA EPISuite software package, respectively.
Executive summary:

Two identical Water Accommodated Fractions (WAFs) were prepared for SHOP Ligand at loading rates of 1 and 5 mg/L pre-determined from the preliminary visual observation studies.  The WAFs were prepared in 2L conical flasks with glass/PTFE taps at the base and sealed with a ground glass stopper. The sample was dosed into the WAF vessels as follows:

•       SHOP Ligand test sample (2 mg and 20 mg) was added directly as a fine powder to the test vessels before adding de-ionised water (2L).

The WAF’s were then stirred under ambient laboratory conditions using a PTFE coated magnetic stirrer at 250 rpm. After stirring periods of 24, 48, 72, 96 and 240 hours the WAFs were left to settle for one hour by stopping the stirring and sub-samples were taken for LC-UV and TOC analysis. Sampling of the WAFs was carried out via the sample tap positioned at the base of the conical flask to prevent any contamination of the WAF samples with the test substance. The first 50 ml was discarded. A blank water-only WAF was set-up in parallel. Samples taken from WAFs which were left stirring for 72h and 96h were analysed with and without centrifugation. WAF samples that were left stirring for 24 and 48h were analysed directly without centrifugation. Centrifugation was carried out using a 15 ml PP tube with HDPE cap for 15 minutes at a speed of 4400 rpm. After centrifugation 1 ml of sample was removed from the top with a glass pipette and discarded. The 96h WAF sample was also subjected to aeration to assess the influence of oxidation on the solubility of the SHOP Ligand (via transformation to the more soluble SHOP ligand oxide by-product) The sample to be used for LC-UV and TOC analysis was taken from the water column in the middle of the PP tube. The bottom fraction of the sample was discarded.

Using the OECD 105 flask method (with LC-UV analysis), the water solubility of SHOP Ligand was observed to be in the range of 0.4-1.0 mg/L after stirring for 240h (10d) at a temperature of 20 (±2) °C, which is in excellent agreement with the computational predicted values of 0.39 – 1.4 mg/L using WSKOWWIN and WATERNT models from the US EPA EPISuite software package, respectively.

Description of key information

An estimation of the water solubility of 2-(diphenylphosphino)benzoic acid was performed using the specialised chemical estimation software, WSKOWWIN, version 1.42 © 2000 and WATERNT v1.01 developed by the US Environmental Protection Agency (part of the EPISUITE software package). The software was validated with reference substances which had common or similar functional groups present as the test material.

Using the US EPA EPIWIN software, the test material was estimated to have a water solubility ranging from 0.39 to 1.4 mg/L at 25°C.

Key value for chemical safety assessment

Water solubility:
0.39 mg/L
at the temperature of:
25 °C

Additional information

Experimental water solubility data to be added once available from STCA