(2-cyano-1-methylethyl)dodecylethylsulphonium tetrafluoroborate(1-)

Water solubility

Link to relevant study record(s)

Reference

Reference 1

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

disregarded due to major methodological deficiencies

Study period:

2016-07-11 to 2016-07-16

Reliability:

3 (not reliable)

Rationale for reliability incl. deficiencies:

unsuitable test system

Remarks:

Test substance rapidly hydrolyze at neutral pH. Test was conducted at the pH 2 and is not relevant to the environmental condition.

Qualifier:

according to guideline

Guideline:

EPA OPPTS 830.7840 (Water Solubility)

GLP compliance:

yes

Type of method:

flask method

Specific details on test material used for the study:

SOURCE OF TEST MATERIAL
- Source and lot/batch No.of test material:605803
- Expiration date of the lot/batch:October 23, 2016
- structure components:
2-Cyano-1-methylethyl-dodecylethyl sulfonium cation: 77.5%
Tetrafluoroborate anion: 22.5%

Water solubility:

1 010 mg/L

Conc. based on:

other:

Remarks:

concentration was determined by summing the measured anion and cation results.

Incubation duration:

> 1 - <= 3 d

Temp.:

22 °C

pH:

2

Remarks on result:

other: The saturated MTDID 15670 solution has pH approximately 2.

Details on results:

The MTDID 15670 sulfonium cation and tetrafluoroborate anion concentrations were measured individually in the aqueous phase on each of the 3 days of incubation. Solubility for MTDID 15670 was determined by summing the results for both components.

MTDID 15670 cation hydrolyze rapidly at neutral pH. The cation analysis samples were diluted with 0.1% aqueous acedic acid. The pH of MTDID 15670 saturated solutions were approximately 2. The measured average sulfonium cation concentrations were 743 mg/L (RSD 7.2%, n=9) for day 1, 640 mg/L (RSD 4.3%, n=9) for day 2, and 554 mg/L (RSD 6.6%, n=9) for day 3. The inter-day (3 days) average sulfonium cation concentration was 646 mg/L (RSD 15%).

MTDID 15670 anion analysis samples were diluted with water. The measured average tetrafluoroborate anion concentrations were 335 mg/L (RSD 3.9%, n=9) for day 1, 352 mg/L (RSD 0.16%, n=9) for day 2, and 397 mg/L (RSD 4.3%, n=9) for day 3. The inter-day average tetrafluoroborate anion concentration was 361 mg/L (RSD 8.9%).

The average inter-day MTDID 15670 solubility concentration was determined to be 1010 mg/L (RSD 6.4%). However, the molar ratio of solubilized anion to solubilized cation increased over time, from 1.55 at day 1, 1.89 at day 2, to 2.47 at day 3. The overall molar ratio of solubilized anion to solubilized cation was 1.97 (RSD 24%). The reasons for this change were unclear at the time of the experiment.

Table 3 Summary of water solubility results for MTDID 15670

Samples	Average MTDID 15670 Cation Conc. (mg/L)	Average MTDID 15670 anion Conc. (mg/L)	Average MTDID 15670 Conc. (mg/L)^(a)	Anion-to-Cation Molar Ratio
Time point 1 (Day 1)	743	335	1080	1.55
Time point 2 (Day 2)	640	352	993	1.89
Time point 3 (Day 3)	554	397	951	2.47
Inter-Day Average	646	361	1010	1.97
Inter-Day  RSD%	15%	8.9%	6.4%	24%

 (a)     MTDID 15670 concentration was determined by summing the measured anion and cation results.

Conclusions:

MTDID 15670 rapidly hydrolyze at neutral pH. Test was conducted at the pH 2 and is not relevant to the environmental condition.

Executive summary:

The water solubility of MTDID 15670 was determined in glass vessels at ambient temperature (22± 2°C) according to the shake flask method described in U.S EPA guidance document OPPTS 830.7840“Water Solubility: Column Elution Method; Shake Flask Method”, and was consistent with OECD Guideline 105 for Testing of Chemicals “Water Solubility”.

Triplicate samples of MTDID 15670 were added to water in excess of its solubility and incubated in glass test vessels out of direct light for 3 days (timepoints 1, 2, 3). Upon removal from the incubator, the samples were placed at ambient temperature (22 ± 2 °C) out of direct light for greater than 24 hours to equilibrate. Then, triplicate aliquots of each sample were removed from the aqueous phase and diluted using aqueous 0.1% acetic acid for MTDID 15670 cation analysis. Aliquots of test samples were similarly prepared by dilution with water for the MTDID 15670 anion and the diluted samples were analyzed by LC/MS/MS.

MTDID 15670 contains a sulfonium cation and a tetrafluoroborate anion components. The MTDID 15670 sulfonium cation and tetrafluoroborate anion concentrations were measured individually in the aqueous phase on each of the 3 days of incubation. Solubility for MTDID 15670 was determined by summing the results for both components. The inter-day (3 days) average sulfonium cation concentration was 646 mg/L (RSD 15%) and the inter-day average tetrafluoroborate anion concentration was 361 mg/L (RSD 8.9%). The average inter-day MTDID 15670 solubility concentration was determined to be 1010 mg/L (RSD 6.4%). This was the maximum solubility attainable at pH 2. However, the molar ratio of solubilized anion to solubilized cation increased over time, from 1.55 at day 1, 1.89 at day 2, to 2.47 at day 3, even though the cation samples were diluted in 0.1% acetic acid. The reason for this change was unclear.

MTDID 15670 rapidly hydrolyze at neutral pH. Although this is a guideline study conducted under GLP compliance, the cation analysis was conducted at the pH 2 and is not relevant to the environmental condition. Consequently, this study is considered not reliable due to unsuitable test system.

Reference 2

Endpoint:

water solubility

Type of information:

not specified

Remarks:

value from SDS

Adequacy of study:

other information

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

documentation insufficient for assessment

Qualifier:

no guideline followed

GLP compliance:

no

Key result

Water solubility:

> 60 g/L

Conclusions:

The water solubility of MTDID 15670 is > 60 g/L (temperature not reported).

Executive summary:

The water solubility of MTDID 15670 is > 60 g/L. Only the result was reported on the MSDS and no information about the temperature or method used was provided; therefore the reliability of the data is not assignable.

Reference 3

Endpoint:

water solubility

Type of information:

not specified

Remarks:

value from handbook

Adequacy of study:

other information

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

documentation insufficient for assessment

Remarks:

experimental value from a handbook

Qualifier:

no guideline available

GLP compliance:

not specified

Type of method:

other: method unknown

Key result

Water solubility:

25 000 mg/L

Temp.:

25 °C

Conclusions:

Crotononitrile is a hydrolysis product of MTDID 15670. It has a reported experimental water solubility of 25000 mg/L at 25 °C.

Executive summary:

Crotononitrile is a hydrolysis product of MTDID 15670. The water solubility of crotononitrile was reported to be 25000 mg/L at 25 °C. Only the result was reported and no information about the test method was provided; therefore the reliability of the data is not assignable.

Reference 4

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

supporting study

Study period:

1993

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

study well documented, meets generally accepted scientific principles, acceptable for assessment

Qualifier:

no guideline followed

Principles of method if other than guideline:

Water solubility were analyzed using the standard additions method. Water and an organic were brought into equilibrium at a given temperature in a thermostatically controlled water bath. Samples of each layer were removed with a syringe for analysis.

GLP compliance:

no

Type of method:

other:

Specific details on test material used for the study:

Crotononitrile purity 99.9%

Water solubility:

3 other: mass %

Conc. based on:

test mat.

Temp.:

20 °C

Table 1. Mutual solubility of Crotononitrile and water

Temp (°C)	Solubility of Crotononitrile in water (mass wt%)	Solubility of water in Crotononitrile (mass wt%)
0	3.23	1.55
10.0	3.17	2.09
20.0	3.00	2.53
30.0	2.99	2.78
40.0	3.04	3.24
50.0	3.16	3.97
60.0	3.24	4.48
70.0	3.68	5.02
80.0	4.39	5.97
90.0	4.19	6.55

 

Conclusions:

The solubility of crotononitrile in water was measured to be 3% wt% at 20 °C.

Executive summary:

Mutual solubilities of crotononitrile in water was measured from 0 to 90 °C. Water and the nitriles were brought into equilibrium at a given temperature in a thermostatically controlled water bath. The incubation period was not reported. Samples from each of the water and the nitrile layer were removed with a syringe for analysis using the standard additions method with a gas chromatography with thermal conductivity detector.

The solubility of crotononitrile in water was measured to be 3% wt% at 20 °C.

This study was not conducted according to test guideline nor under GLP. However, it was well documented and met generally accepted scientific principles. Therefore, it is reliable with restriction and acceptable for assessment.

Reference 5

Endpoint:

water solubility

Type of information:

(Q)SAR

Adequacy of study:

supporting study

Study period:

2018-05-22 to 2018-05-25

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:

QMRF and QPRF attached

Qualifier:

according to guideline

Guideline:

other: Guidance on information requirements and chemical safety assessment: Chapter R.6: QSARs and grouping of chemicals

Deviations:

no

GLP compliance:

no

Remarks:

QSAR model

Type of method:

other: calculation method (fragments) WATERNT v1.01 as implemented through EPI Suite v4.11

Specific details on test material used for the study:

For Hydrolysis product of MTDID 15670:
Chemical name: Dodecyl ethyl sulfide
CAS# N/A
SMILES: S(CCCCCCCCCCCC)CC

Key result

Water solubility:

0.027 mg/L

Conc. based on:

test mat.

Temp.:

25 °C

Conclusions:

Dodecyl ethyl sulfide is a hydrolysis product of MTDID 15670. Dodecyl ethyl sulfide has an estimated water solubility of 0.027 mg/L at 25 °C using WATERNT v1.01 as implemented through EPISuite v4.11.

Executive summary:

Dodecyl ethyl sulfide is identified as one of the hydrolysis products of MTDID 15670. The water solubility of dodecyl ethyl sulfide was estimated to be 0.027 mg/L at 25 °C using the WATRENT v1.01QSAR as implemented through EPI Suite v4.11. The software is an accepted, valid model for estimation of water solubility. The structure of dodecyl ethyl sulfide is within the parametric domain of the model (molecular weight, maximum number of structural fragments per structure, predicted water solubility). The use of this QSAR to predict water solubility for dodecyl ethyl sulfide was deemed to be applicable and reliable based on representation of analogous substances within the training set and performance statistics (a correlation coefficient (r^2) of 0.992, a standard deviation of 0.272, and an absolute mean error of 0.228) derived from a comparison of experimental and estimated log WS (mole/L) for 13 representative analogous substances.

This study is classified as an acceptable QSAR and satisfies the requirements for water solubility study. It is pertinent to the fate and effect of MTDID 15670 and may be used for risk analysis, classification and labelling, and PBT analysis.

Reference 6

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

supporting study

Reliability:

4 (not assignable)

Rationale for reliability incl. deficiencies:

secondary literature

Remarks:

result reported in IUCLID Dataset, but no details provided

Key result

Water solubility:

4.4 g/L

Temp.:

20 °C

pH:

3 - 4

Details on results:

No details regarding the result were provided.

Conclusions:

Potassium tetrafluoroborate has a water solubility of 4.4 g/L at 20 °C, as reported in an IUCLID Dataset.

Executive summary:

Potassium tetrafluoroborate has a water solubility of 4.4 g/L at 20 °C, as reported in an IUCLID Dataset. Tetrafluoroborate is the anion of MTDID 15670, which is released upon dissociation. No details regarding this data were available, therefore its reliability is not assignable.

Reference 7

Endpoint:

water solubility

Data waiving:

study scientifically not necessary / other information available

Justification for data waiving:

the study does not need to be conducted because the substance is hydrolytically unstable at pH 4, 7 and 9 (half-life less than 12 hours)

Reason / purpose for cross-reference:

data waiving: supporting information

Description of key information

Experimental measurement of water solubility for MTDID 15670 is not required due to its dissociation in water and rapid hydrolysis. The identified dissociation and hydrolysis products have water solubility values of  4.4 g/L (pH 3 - 4) at 20 °C, 3 wt% at 20 °C, and 0.027 mg/L at 25 °C for potassium tetrafluoroborate, crotonitrile, and dodecyl ethyl sulfide, respectively.

Additional information

The water solubility of MTDID 15670 was determined according to the U.S EPA guidance document OPPTS 830.7840“Water Solubility: Column Elution Method; Shake Flask Method”. A maximum solubility of 1010 mg/L (RSD 6.4%) was obtained at pH 2. As this is not relevant to the environmental condition, this study is considered not reliable (Klimisch 3) and a disregarded study due to unsuitable test system. Another water solubility value of > 60 g/L was reported on a Safety Data Sheet. This data has no information about the test temperature or method, and is considered insufficient for assessment (Klimisch 4) and disregarded data.

MTDID 15670 dissociates in water to an organic sulfonium (cation) component and an inorganic tetrafluoroborate (BF4(-) anion) component. The cation hydrolyzes to crotononitrile and dodecyl ethyl sulfide with a hydrolytic half-life of 2.08 hours at pH 7 and 4 °C, and 4.59 hours at pH 4 and 50 °C.  As such, experimental measurement of water solubility under section 7.7 is not required. However, the water solubilities of the hydrolysis products are pertinent to the fate of MTDID 15670 and may be used for risk analysis, classification and labelling, and PBT analysis.

A water solubility of 4.4 g/L at 20 °C for potassium tetrafluoroborate was reported in an IUCLID Dataset.

Crotononitrile has a measured water solubility of 3% wt% at 20 °C, obtained from a published research journal. This study was well documented and met generally accepted scientific principles. Therefore, it is considered reliable with restriction (Klimisch 2) and a supporting study. A water solubility value of 25000 mg/L at 25 °C was also reported for crotononitrile on a public handbook. Only the result was reported and no information about the test method was provided, therefore the reliability of the data is not assignable (Klimisch 4).

The water solubility of dodecyl ethyl sulfide was estimated using the using WATERNT v1.01 as implemented through EPISuitev4.11. The software is an accepted, valid model for estimation of water solubility. Dodecyl ethyl sulfide has an estimated water solubility of 0.027 mg/L at 25 °C. This study is classified as an acceptable QSAR and satisfy the requirements for water solubility study and is a supporting study.