Ethylene bis[1,3-dihydro-1,3-dioxoisobenzofuran-5-carboxylate]

Partition coefficient

Administrative data

Endpoint:

partition coefficient

Type of information:

experimental study

Adequacy of study:

key study

Study period:

Experimental starting date: 26 October 2017 Experimental completion date: 07 March 2018

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

guideline study

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2018

Materials and methods

Test guideline

Qualifier:

according to guideline

Guideline:

OECD Guideline 117 (Partition Coefficient (n-octanol / water), HPLC Method)

GLP compliance:

yes (incl. QA statement)

Type of method:

HPLC method

Partition coefficient type:

octanol-water

Test material

Test material information

Constituent 1

Reference substance name:

Ethylene bis[1,3-dihydro-1,3-dioxoisobenzofuran-5-carboxylate]

EC Number:

217-062-1

EC Name:

Ethylene bis[1,3-dihydro-1,3-dioxoisobenzofuran-5-carboxylate]

Cas Number:

1732-96-3

Molecular formula:

C20H10O10

IUPAC Name:

2-(1,3-dioxo-1,3-dihydro-2-benzofuran-5-carbonyloxy)ethyl 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxylate

impurity 1

Reference substance name:

Benzene-1,2,4-tricarboxylic acid 1,2-anhydride

EC Number:

209-008-0

EC Name:

Benzene-1,2,4-tricarboxylic acid 1,2-anhydride

Cas Number:

552-30-7

Molecular formula:

C9H4O5

IUPAC Name:

Benzene-1,2,4-tricarboxylic acid 1,2-anhydride

impurity 2

Reference substance name:

not assignable

IUPAC Name:

not assignable

Specific details on test material used for the study:

Identification: RIKACID TMEG-500
CAS No.: 1732-96-3
Chemical name: Ethylene bis[1,3-dihydro-1,3-dioxoisobenzofuran-5-carboxylate]
Appearance/physical state: cream colored powder
Batch: 5259
Purity: 81.1%
Expiry date: 24 April 2018
Storage conditions: room temperature, in the dark

Study design

Analytical method:

high-performance liquid chromatography

Results and discussion

Partition coefficient

Type:

log Pow

Partition coefficient:

3.33

Temp.:

30 °C

pH:

1.5

Details on results:

Preliminary Estimate
The log10 Pow was calculated to be 3.47.

Definitive Test Calibration
Mean log10 Pow: 3.33
Partition coefficient: 2.11 x 10^3




 

Any other information on results incl. tables

Calibration

 

The retention times of the dead time and the retention times, capacity factors (k') and log₁₀ P_owvalues for the reference standards are shown in the following tables. 

Dead time	Retention Time (mins)		Mean Retention Time (mins)
	Injection 1	Injection 2
Thiourea	1.273	1.273	1.273

 

Standard	Retention Time (mins)			Capacity Factor (k')	Log10k'	Log10Pow
	Injection 1	Injection 2	Mean
2-Butanone	1.691	1.696	1.693	0.330	-0.481	0.3
Benzyl alcohol	1.808	1.808	1.808	0.420	-0.377	1.1
Benzene	4.417	4.417	4.417	2.469	0.393	2.1
Toluene	6.788	6.788	6.788	4.332	0.637	2.7
Naphthalene	10.160	10.165	10.163	6.983	0.844	3.6
Phenanthrene	24.553	24.553	24.553	18.286	1.262	4.5

 

Partition coefficient of sample

 

The retention times, capacity factor and log₁₀P_owvalue determined for the sample are shown in the following table:

Injection	Retention Time (mins)	Capacity Factor (k')	Log10k'	Log10Pow
1	9.106	6.153	0.789	3.33
2	9.106	6.153	0.789	3.33

Mean log₁₀P_ow: 3.33
Partition coefficient:  2.11 x 10³

 Discussion

Although the parent test item contained no dissociating functional groups, the mobile phase was strongly acidified in order to minimize hydrolysis of the test item’s acid anhydride functional groups, which is typically a base catalyzed reaction. Despite this precautionary step, reactivity of the test item within the mobile phase remained evident. In addition to the major peak eluting at approximately 9 minutes, which was attributed to the parent test item and used for quantification of the partition coefficient, further, earlier eluting, more hydrophilic peaks were observed, which were attributed to the hydrolysis products of the test item.

During development of the analytical method for the determination, on preparation of a test item sample solution in mobile phase, as opposed to acetonitrile, only proposed hydrolysis product peaks were observed on analysis. This fully supported the instability of the test item in even a strongly acidified mobile phase. 

 

Applicant's summary and conclusion

Conclusions:

The partition coefficient of the test item has been determined to be 2.11 x 10^3, log10 Pow 3.33.

Executive summary:

Partition Coefficient (n-Octanol/water). 2.11 x 10³, log₁₀P_ow 3.33, determined using an HPLC method designed to be compatible with Method A.8 Partition Coefficient of Commission Regulation (EC) No 440/2008 of 30 May 2008andMethod 117 of the OECD Guidelines for Testing of Chemicals, 13 April 2004.