Butylidenebis[2-tert-butyl-5-methyl-p-phenylene]-P,P,P',P'-tetratridecylbis(phosphine)

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

key study

Study period:

2018

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:

OECD Guideline 111 (Hydrolysis as a Function of pH)

GLP compliance:

yes

Test material

Test material information

Constituent 1

Reference substance name:

Butylidenebis[2-tert-butyl-5-methyl-p-phenylene]-P,P,P',P'-tetratridecylbis(phosphine)

EC Number:

235-841-4

EC Name:

Butylidenebis[2-tert-butyl-5-methyl-p-phenylene]-P,P,P',P'-tetratridecylbis(phosphine)

Cas Number:

13003-12-8

Molecular formula:

C78H144O6P2

IUPAC Name:

4-[2-(4-{[bis(tridecyloxy)phosphanyl]oxy}-5-tert-butyl-2-methylphenyl)pentyl]-5-methyl-2-(propan-2-yl)phenyl ditridecyl phosphite

Test material form:

liquid

Specific details on test material used for the study:

Lot No.: 352Y7, Purity = 99.9%. The test material and BBMC were provided by the study sponsor via Chang Chun Petrochemical Co., (CAS No.: 85-60-9, Lot No.: 307Z7, Purity = 99.12%) and was received on 8 January 2018 and stored at room temperature.

Radiolabelling:

no

Study design

Analytical monitoring:

yes

Details on sampling:

The sampling was conducted on 6,6'-di-tert-butyl-4,4'-butylidenedi-m-cresol (BBMC), which is a hydrolysis product.

Duration of test

Duration:

7 d

pH:

7

Temp.:

20 °C

Number of replicates:

3

Positive controls:

no

Negative controls:

no

Results and discussion

Transformation products:

yes

Identity of transformation products

No.:

#1

Reference

Reference substance name:

Unnamed

IUPAC name:

6,6'-di-tert-butyl-4,4'-butylidenedi-m-cresol

Inventory number:

InventoryMultipleMappingImpl [inventoryEntryValue=EC 201-618-5]

CAS number:

85-60-9

Molecular formula:

C26H38O2

Dissipation DT50 of parent compound

pH:

7

Temp.:

20 °C

DT50:

< 68.5 h

Type:

other: BBMC Recovery

Any other information on results incl. tables

Based upon chromatographic peak area counts of BBMC standard solutions, a calibration standard curve (Figure 1) was constructed to determine BBMC concentrations in buffer samples. The calculated BBMC concentrations in 0.05 - 1.00 mg/L standard solutions based on the calibration standard curve were within ±15% of nominal concentrations. However, the base-line resolved peak shape of the 0.05 mg/L BBMC standard solution was not smooth (Appendix I). Therefore, the LOQ for BBMC was estimated to be approximately 0.10 mg/L, equivalent to the concentration of 0.10 mg/L calibration standard which also demonstrated a smooth base-line resolved chromatographic peak (Appendix I). Taking into consideration a dilution factor (2 ×) during sample processing and a correction factor (3.24 ×) for mol% (molecular weight of DP-1/BBMC = 3.24), it was estimated that a test concentration of at least ~6.5 mg/L DP-1 in buffer solution would be necessary to quantify BBMC equivalent to at least 10 mol% applied DP-1 to each test vessel containing a buffer solution. 

 

Figure 2 presents the results of DP-1 hydrolysis over 68.5 hours. BBMC was detected in all samples. For time zero samples, BBMC was about 4.17 mol% in buffer containing DP-1 loaded silica gel and 3.47 mol% in buffer directly mixed with DP-1 stock solution. The presence of BBMC in time zero samples is likely due to the impurity or background level of BBMC in DP-1 test substance. For directly mixing samples, BBMC was increased slightly to 6.07 mol% over 68.5 hours, indicating very little (~ 2.6 mol%) BBMC was released from DP-1. In contrast, BBMC was increased to 35.1 mol% over 68.5 hours, a net increase of ~ 30.9 mol%, suggesting that DP-1 was partially hydrolyzed to BBMC facilitated by silica gel dispersion.  

 

Conclusions

 

• An HPLC method was established to quantify BBMC with a LOQ of 0.10 mg/L in standard solution.
• Based upon the LOQ and the sample preparation scheme, a DP-1 test concentration (~ 6.5 mg/L) was identified, which ensured that the hydrolysis of 90 mol% of DP-1 dosed to the test vessels could be tracked analytically.
• DP-1 was partially hydrolyzed in neutral buffer (pH = 7.0) to BBMC over 68.5 hours, with a net yield of approx. 30.9% mol%.
• Further experiments are needed to obtain detailed kinetic data for DP-1 hydrolysis with silica gel dispersion method.

 

Applicant's summary and conclusion

Conclusions:

The test material hydrolyzes based on the formation of BBMC in the testing solutation.

Executive summary:

The test material hydrolyzes based on the formation of BBMC in the testing solutation.