reaction mass of 2-[[1-(chloromethyl)-2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxy]ethoxy]methyl]oxirane and cis-1,4-bis[(2,3-epoxypropoxy)methyl]cyclohexane and trans-1,4-bis[(2,3-epoxypropoxy)methyl]cyclohexane

Water solubility

Administrative data

Endpoint:

water solubility

Type of information:

experimental study

Adequacy of study:

key study

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

Qualifier:

according to guideline

Guideline:

EPA OPPTS 830.7840 (Water Solubility)

GLP compliance:

no

Other quality assurance:

ISO/IEC 17025 (General requirements for the competence of testing and calibration laboratories)

Type of method:

flask method

Test material

Test material information

Constituent 1

Reference substance name:

2-[[1-(chloromethyl)-2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxy]ethoxy]methyl]oxirane

Molecular formula:

C17H29ClO5

IUPAC Name:

2-[[1-(chloromethyl)-2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxy]ethoxy]methyl]oxirane

Constituent 2

Reference substance name:

cis-1,4-bis[(2,3-epoxypropoxy)methyl]cyclohexane

Cas Number:

1197197-64-0

Molecular formula:

C14H26O4

IUPAC Name:

cis-1,4-bis[(2,3-epoxypropoxy)methyl]cyclohexane

Constituent 3

Reference substance name:

trans-1,4-bis[(2,3-epoxypropoxy)methyl]cyclohexane

Cas Number:

158307-92-7

Molecular formula:

C14H26O4

IUPAC Name:

trans-1,4-bis[(2,3-epoxypropoxy)methyl]cyclohexane

impurity 1

Reference substance name:

[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methanol

Molecular formula:

C11H20O3

IUPAC Name:

[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methanol

impurity 2

Reference substance name:

[4-[[3-chloro-2-(oxiran-2-ylmethoxy)propoxy]methyl]cyclohexyl]methanol

Molecular formula:

C14H25ClO4

IUPAC Name:

[4-[[3-chloro-2-(oxiran-2-ylmethoxy)propoxy]methyl]cyclohexyl]methanol

impurity 3

Reference substance name:

2-[[3-chloro-2-[[4-[[3-chloro-2-(oxiran-2-ylmethoxy)propoxy]methyl]cyclohexyl]methoxy]propoxy]methyl]oxirane

Molecular formula:

C20H34Cl2O6

IUPAC Name:

2-[[3-chloro-2-[[4-[[3-chloro-2-(oxiran-2-ylmethoxy)propoxy]methyl]cyclohexyl]methoxy]propoxy]methyl]oxirane

impurity 4

Specific details on test material used for the study:

- lot/batch No.of test material:TN17-0446-1/1
- Expiration date of the lot/batch:12/10/2022

Results and discussion

Water solubility

Water solubility 1

Key result

Water solubility:

10.2 g/L

Conc. based on:

other: for the primary component 1,4-Bis[(2,3-epoxypropoxy)methyl]cyclohexane (EMC)

Incubation duration:

3 d

Temp.:

22.5 °C

pH:

ca. 6

Water solubility 2

Key result

Water solubility:

0.703 g/L

Conc. based on:

other: for 1,4-Bis[(2,3-epoxypropoxy)methyl] cyclohexane + epichlorohydrin (EMCECH)

Incubation duration:

3 d

Temp.:

22.5 °C

pH:

ca. 6

Details on results:

MTDID 51951 consists of two primary components: 1,4-bis[(2,3-epoxypropoxy) methyl] cyclohexane (EMC) and 1,4-bis[(2,3-epoxypropoxy)methyl] cyclohexane + epichlorohydrin (EMCECH). The water saturation equilibrium (maximal water solubility) values for EMC and EMCECH were achieved after 1 day of incubation and were maintained over 3 days. The intra-day average water solubility of EMC were 10.5 g/L, 10.1 g/L and 10.0 g/L for day 1, 2, and 3, respectively. The intra-day average water solubility of EMCECH were 0.743 g/L, 0.668 g/L and 0.698 g/L for day 1, 2, and 3, respectively. The overall water solubility was 10.2 g/L (RSD% = 2.6%) for EMC; the overall water solubility was 0.703 g/L (RSD% = 5.3%) for EMCECH.

Any other information on results incl. tables

Table 1: Summary of Water Saturation Concentrations (g/L) of EMC at Ambient Temperature

 

Samples	Time point 1 (day 1)	Time point 2 (day 2)	Time point 3 ( day 3)
Sample 1, Rep 1	12.5	9.83	9.55
Sample 1, Rep 2	10.0	9.60	10.3
Sample 1, Rep 3	10.1	9.63	9.87
Sample 1 Average (RSD%)	10.9 (13%)	9.69 (1.3%)	9.91 (3.8%)
Sample 2, Rep 1	10.1	11.8	10.3
Sample 2, Rep 2	10.0	10.4	10.4
Sample 2, Rep 3	9.85	9.85	10.2
Sample 2 Average (RSD%)	10.0 (1.3%)	10.7 (9.4%)	10.3 (1.0%)
Sample 3, Rep 1	12.1	9.77	9.75
Sample 3, Rep 2	10.0	9.93	9.67
Sample 3, Rep 3	9.88	10.0	9.97
Sample 3 Average (RSD%)	10.7 (12%)	9.90 (1.2%)	9.80 (1.6%)
Intra-day Average (g/L)	10.5	10.1	10.0
Intra-day RSD%	4.4%	5.2%	2.6%
Overall Average (g/L)				10.2
Overall RSD %				2.6%

 

 Table 2: Summary of Water Saturation Concentrations (g/L) of EMCECH at Ambient Temperature

 

Samples	Time point 1 (day 1)	Time point 2 (day 2)	Time point 3 ( day 3)
Sample 1, Rep 1	2.12 ^a	0.650	0.679
Sample 1, Rep 2	0.783	0.648	0.711
Sample 1, Rep 3	0.745	0.646	0.673
Sample 1 Average (RSD%)	0.764 (5% RPD)	0.648 (0.31%)	0.688 (3.0%)
Sample 2, Rep 1	0.703	1.82 ^a	0.931
Sample 2, Rep 2	0.676	0.741	0.703
Sample 2, Rep 3	0.734	0.653	0.698
Sample 2 Average (RSD%)	0.704 (4.1%)	0.697 (13% RPD)	0.777 (17%)
Sample 3, Rep 1	2.15 ^a	0.670	0.630
Sample 3, Rep 2	0.833	0.662	0.614
Sample 3, Rep 3	0.689	0.649	0.644
Sample 3 Average (RSD%)	0.761 (19% RPD)	0.660 (1.6%)	0.629 (2.4%)
Intra-day Average (g/L)	0.743	0.668	0.698
Intra-day RSD%	4.5	3.8	11
Overall Average (g/L)				0.703
Overall RSD %				5.3%

 a.      Data were outliers based on Q-Test and were not used for the calculation.

 

 

 

Applicant's summary and conclusion

Conclusions:

The measured water solubilities for the two MTDID 51951 primary constituents EMC and EMCECH were 10.2 g/L (RSD 2.6%) and 0.703 g/L (RSD 5.3%), respectively.

Executive summary:

The water solubility of MTDID 51951 was determined according to the U.S. EPA guidance document OPPTS 830.7840 “Water Solubility: Column Elution Method; Shake Flask Method”.

Triplicate samples were prepared by adding 0.8 g of test substance to the bottom of a test vial, then 2.0 mL of Milli-Q™ water was added to each vial. Samples were then incubated in a shaker at a setting of 100 revolutions per minute (RPM) and approximately 30 °C and for three incubation time points (1, 2, and 3 days). At the end of each time point, the vials were removed from the incubator, and placed at room temperature out of direct light for approximately 24 hours to equilibrate. The vials were then centrifuged. Triplicate aliquots of aqueous phase were removed, diluted in methanol, and analyzed via LC/MS/MS.

MTDID 51951 consists of two primary components: 1,4-bis[(2,3-epoxypropoxy)methyl] cyclohexane (EMC) and 1,4-bis[(2,3-epoxypropoxy)methyl] cyclohexane + epichlorohydrin (EMCECH). The water saturation equilibrium (maximal water solubility) values for EMC and EMCECH were achieved after 1 day of incubation and were maintained over 3 days. The overall water solubility was 10.2 g/L (RSD% = 2.6%) for EMC; the overall water solubility was 0.703 g/L (RSD% = 5.3%) for EMCECH.

This is a guideline study. Although it was not conducted under GLP, the study was well documented, and achieved good accuracy and precision. Therefore, it is considered reliable without restrictions and a key study.