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EC number: 243-424-3 | CAS number: 19910-65-7
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
Hydrolysis
Administrative data
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Study period:
- Study initiation date: 23 January 2012 Study completion date: 16 May 2013
- Reliability:
- 1 (reliable without restriction)
- Rationale for reliability incl. deficiencies:
- guideline study
Data source
Reference
- Reference Type:
- study report
- Title:
- Unnamed
- Year:
- 2 013
- Report date:
- 2013
Materials and methods
Test guidelineopen allclose all
- Qualifier:
- according to guideline
- Guideline:
- OECD Guideline 111 (Hydrolysis as a Function of pH)
- Qualifier:
- according to guideline
- Guideline:
- EU Method C.7 (Degradation: Abiotic Degradation: Hydrolysis as a Function of pH)
- Qualifier:
- according to guideline
- Guideline:
- EPA OPPTS 835.2120 (Hydrolysis of Parent and Degradates as a Function of pH at 25°C)
- GLP compliance:
- yes (incl. QA statement)
Test material
- Reference substance name:
- Bis-sec-butyl peroxydicarbonate
- EC Number:
- 243-424-3
- EC Name:
- Bis-sec-butyl peroxydicarbonate
- Cas Number:
- 19910-65-7
- Molecular formula:
- C10H18O6
- IUPAC Name:
- 2-[({[(butan-2-yloxy)carbonyl]peroxy}carbonyl)oxy]butane
- Test material form:
- liquid
Constituent 1
- Specific details on test material used for the study:
- The specific details on the test material used for this study were as follows:
Description: clear, colourless liquid
Batch number: 08081B1901
Purity: 99.88%
Expiry I Retest Date: 30 May 2012
Storage Conditions: approximately -20 °C, in the dark - Radiolabelling:
- not specified
Study design
- Analytical monitoring:
- yes
- Remarks:
- HPLC
- Details on sampling:
- A plastic, 50 m L volumetric flask was partially filled with acetonitrile and 0.5 g of test item added. This was then diluted to volume with acetonitrile to give a stock solution at a concentration of 1 x 10^4 mg/L. An aliquot of stock solution (15 mL) was diluted to a total volume of 50 mL with acetonitrile to prepare a spike solution at a concentration of 3 x 10^3 mg/L.
Aliquots of the spike solution were then diluted by a factor of 100 using the appropriate buffer solutions, such that a sample solution concentration of 30 mg/L (3.0 x 10^-2 g/L) was achieved,
employing 1 % v/v acetonitrile co-solvent. Successful dissolution was confirmed by a Tyndall beam assessment.
The concentration of each solution did not exceed the lesser of 0.0 1 mol/L or half the estimated water solubility of the test item (7.3 x 10^-2 g/L, WSKOWWIN version 1.42, September 2010, ©
2000 U.S. Environmental Protection Agency).
The test solutions were split into multiple, individual vessels, with duplicate independent vessels being analyzed at each data point. The remaining test solution was also analyzed in duplicate to
provide initial timepoint data.
The solutions were shielded from light whilst maintained at the test temperature. - Buffers:
- See "Materials and Methods" section below.
Duration of testopen allclose all
- Duration:
- 7 h
- pH:
- 4
- Temp.:
- 25 °C
- Initial conc. measured:
- ca. 0.017 g/L
- Duration:
- 7 h
- pH:
- 7
- Temp.:
- 25 °C
- Initial conc. measured:
- ca. 0.031 g/L
- Duration:
- 5 h
- pH:
- 9
- Temp.:
- 25 °C
- Initial conc. measured:
- ca. 0.016 g/L
- Duration:
- 30 h
- pH:
- 4
- Temp.:
- 15 °C
- Initial conc. measured:
- ca. 0.016 g/L
- Duration:
- 30 h
- pH:
- 7
- Temp.:
- 15 °C
- Initial conc. measured:
- ca. 0.029 g/L
- Duration:
- 5 h
- pH:
- 9
- Temp.:
- 15 °C
- Initial conc. measured:
- ca. 0.026 g/L
- Duration:
- 5 h
- pH:
- 1.2
- Temp.:
- 37 °C
- Initial conc. measured:
- ca. 0.029 g/L
- Duration:
- 5 h
- pH:
- 4
- Temp.:
- 37 °C
- Initial conc. measured:
- ca. 0.015 g/L
- Duration:
- 5 h
- pH:
- 7
- Temp.:
- 37 °C
- Initial conc. measured:
- ca. 0.027 g/L
- Duration:
- 2 h
- pH:
- 9
- Temp.:
- 37 °C
- Initial conc. measured:
- ca. 0.023 g/L
- Number of replicates:
- 2 replicates per pH per temperature
- Positive controls:
- not specified
- Negative controls:
- not specified
Results and discussion
- Transformation products:
- yes
Identity of transformation products
- No.:
- #1
Reference
- Reference substance name:
- Unnamed
- IUPAC name:
- butan-2-ol
- Inventory number:
- InventoryMultipleMappingImpl [inventoryEntryValue=EC 201-158-5]
- CAS number:
- 78-92-2
Dissipation DT50 of parent compoundopen allclose all
- Key result
- pH:
- 1.2
- Temp.:
- 37 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 83 min
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 4
- Temp.:
- 15 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 6.22 h
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 4
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 2.05 h
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 4
- Temp.:
- 37 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 54 min
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 7
- Temp.:
- 15 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 8.37 h
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 7
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 3.83 h
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 7
- Temp.:
- 35 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 94 min
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 9
- Temp.:
- 15 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 100 min
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 9
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0 s-1
- DT50:
- 33 min
- Type:
- (pseudo-)first order (= half-life)
- Key result
- pH:
- 9
- Temp.:
- 37 °C
- Hydrolysis rate constant:
- 0.002 s-1
- DT50:
- 7 min
- Type:
- (pseudo-)first order (= half-life)
Any other information on results incl. tables
Testing at 25.0± 0.5 °C
Slope = -0. 147
kobs = 0.338 hour-1
= 9.38 x 10-5 second-1
t1/2 = 2.05 hours
pH 7 at 25.0 ± 0.5°C
Slope = -7.86 x 10-2
kobs= 0. 181 hour-1
= 5.03 x 10-5 second-1
t1/2 = 3.83 hours
pH 9 at 25.0 ± 0.5°C
Data beyond 1.50 hours incubation has been excluded from calculations due t o excessive fluctuation at the trace concentrations remaining. In addition, the 1.00 hour replicate A sample has been excluded from the final correlation due to inconsistency.
Slope = -0.553
kobs= 1.27 hour-1
= 3.54 x 10-4 second-1
t1/2 = 0.544 hours
= 33 minutes
pH 4 at 15.0 ± 0.5°C
Slope = -4.84 x 10-2
kobs= 0. 112 hour-1
= 3.10 x 10-5 second-1
t1/2= 6.22 hours
pH 7 at 15.0 ± 0.5°C
Slope = -3.60 x 10-2
kobs= 8.29 x 10-2 hour-1
= 2.30 x 10-5 second-1
t1/2= 8.37 hours
pH 9 at 15.0 ± 0.5°C
Slope = -0. 180
kobs= 0.414 hour-1
= 1.15 x 10-4 second-1
t1/2= 1.67 hours
= 100 minutes
pH 1.2 at 37.0 ± 0.5°C
Slope = -0.218
kobs= 0.503 hour-1
= 1.40 x 10-4second-1
t1/2= 1.38 hours
= 83 minutes
pH 4 at 37.0 ± 0.5°C
Slope = -0.332
kobs= 0.765 hour-1
= 2.12 x 10-4second-1
t1/2= 0.907 hours
= 54 minutes
pH 7 at 37.0 ± 0.5°C
Slope = -0.192
kobs= 0.442 hour-1
= 1.23 x 10-4second-1
t1/2= 1.57 hours
= 94 minutes
pH 9 at 37.0 ± 0.5°C
Slope = -2.61
kobs= 6.02 hour-1
= 1.67 x 10-3second-1
t1/2= 0.115 hours
= 7 minutes
On generation of an Arrhenius plot for each pH where 3 individual temperatures have been employed, a further estimation of the rate constant and estimated half-life at 25 °C of the test item can be obtained from the data set as a whole. This further data evaluation resulted in values as shown in the following table:
pH |
Rate constant (s-1) |
Estimated half-life at 25 °C |
4 |
8.22 x 10-5 |
2.34 hrs |
7 |
5.06 x 10-5 |
3.80 hrs |
9 |
3.89 x 10-4 |
30 mins |
As the test item could be readily predicted to hydrolyses, and to limit the influence of possible thermal degradation mechanisms, testing was initiated directly at 25 °C as opposed to performing a preliminary test at 50 °C. Testing was then performed at 15 °C, reducing the hydrolysis rate and also generating information beneficial to ecotoxicology assessments. For the final of the total of three individual temperatures differing by at least 10 °C required by the test guidelines, 37 °C was selected (as opposed to 35 °C) due to its value in assessing the influence of hydrolysis on mammalian toxicology studies.
The kinetics of the study have been determined to be consistent with that of a pseudo-first order reaction as the graphs of log10 concentration versus time were straight lines. Over the environmentally relevant pH range of 4 to 9, it was observed that the rate of hydrolysis increased with a move away from a neutral pH, but accelerated significantly under basic conditions.
Identification of Hydrolysis Products: Results
The sec-butanol concentrations are shown in the following table:
Sample |
Concentration (M) |
Hydrolyzed pH 4 sample solution |
2.52 x 10-4 |
Hydrolyzed pH 7 sample solution |
2.55 x 10-4 |
Hydrolyzed pH 9 sample solution |
2.53 x 10-4 |
Based on the test item molecular weight of 234.25 and an initial sample solution concentration of 3.00 x 10-2 g/L, this equates to an initial test item concentration of 1.27 x 10-4 M. The conversion rate for each hydrolyzed sample from test item to sec-butanol is subsequently summarized in the following table:
Sample |
Sec-Butanol Generation (M per M of test item) |
pH 4 |
1.97 |
pH 7 |
1.99 |
pH 9 |
1.97 |
This therefore confirmed hydrolysis of the test item to sec-butanol by both acidic and basic mechanisms, with essentially 100% mass balance for the initial sample solution concentration achieved.
The remaining central peroxydicarbonic acid was considered to degrade further, possibly through a series of highly unstable intermediates, to carbon dioxide under acidic conditions and potentially a mixture of carbon dioxide and oxygen under basic conditions.
Analysis was performed on completely hydrolyzed samples, as sec-butanol may potentially have been generated from any residual parent test item present by thermal decomposition during the
analytical technique employed.
Applicant's summary and conclusion
- Validity criteria fulfilled:
- yes
- Conclusions:
- The hydrolysis characteristics of the test item at pH 4, pH 7 and pH 9 have been evaluated at temperatures of 15.0± 0.5 °C, 25.0± 0.5 °C and 37.0± 0.5 °C. In addition, the hydrolysis characteristics of the test item under the physiologically relevant conditions of pH 1.2 at 37.0± 0.5 °C have also been evaluated. The results are summarized below:
At 15 ± 0.5 °C:
pH Rate constant (s^-1) Half-life
1.2 - -
4 3.10 x 10^-5 6.22 hrs
7 2.30 x 10^-5 8.37 hrs
9 1.15 x 10^-4 100 mins
At 25 ± 0.5 °C:
pH Rate constant (s^-1) Half-life
1.2 - -
4 9.38 x 10^-5 2.05 hrs
7 5.03 x 10^-5 3.83 hrs
9 3.54 x 10^-4 33 mins
At 37 ± 0.5 °C:
pH Rate constant (s^-1) Half-life
1.2 1.40 x 10^-4 83 mins
4 2.12 x 10^-4 54 mins
7 1.23 x 10^-4 94 mins
9 1.67 x 10^-3 7 mins
On generation of an Arrhenius plot for each pH where 3 individual temperatures have been employed, a further estimation of the rate constant and estimated half-life at 25 °C of the test item can be obtained from the data set as a whole. This further data evaluation resulted in values as shown below:
pH Rate constant (s^-1) Half-life
4 8.22 x 10^-5 2.34 hrs
7 5.06 x 10^-5 3.80 hrs
9 3.89 x 10^-4 30 mins
The test item has been positively identified to hydrolyze to sec-butanol by both acidic and basic mechanisms, with a mass balance/conversion factor of 2 moles of sec-butanol (actual experimental range 1.97 to 1.99) per mol of initial parent test item. The remaining central peroxydicarbonic acid was considered to degrade further, possibly through a series of highly
unstable intermediates, to carbon dioxide under acidic conditions and potentially a mixture of carbon dioxide and oxygen under basic conditions. - Executive summary:
The hydrolysis characteristics of Di-sec-butyl Peroxydicarbonate (CAS# 199 10-65-7), as a function of pH, have been determined.
Assessment of hydrolytic stability was carried out using a procedure designed to be compatible with Method C7 Abiotic Degradation, Hydrolysis as a Function of pH of Commission Regulation (EC) No 440/2008 of 30 May 2008, Method 1 1 1 of the OECD Guidelines for Testing of Chemicals, 13 April 2004 and Method 835.2 120 of the OPPTS Guidelines. The results of individual tests and specified test temperatures and pH's were as follows:
pH
15±0.5 °C
25.0±0.5 °C
37.0±0.5 °C
Rate constant (s-1)
Half-life
Rate constant (s-1)
Half-life
Rate constant (s-1)
Half-life
1.2
-
-
-
-
1.40 x 10-4
83 mins
4
3.10 x 10-5
6.22 hrs
9.38 x 10-5
2.05 hrs
2.12 x 10-4
54 mins
7
2.30 x 10-5
8.37 hrs
5.03 x 10-5
3.83 hrs
1.23 x 10-4
94 mins
9
1.15 x 10-4
100 mins
3.54 x 10-4
33 mins
1.67 x 10-3
7 mins
On generation of an Arrhenius plot for each pH where 3 individual temperatures have been employed, a further estimation of the rate constant and estimated half-life at 25 °C of the test item can be obtained from the data set as a whole. This further data evaluation resulted in values as shown in the following table:
pH
Rate constant (s-1)
Estimated half-life at 25 °C
4
8.22 x 10-5
2.34 hrs
7
5.06 x 10-5
3.80 hrs
9
3.89 x 10-4
30 mins
The test item has been positively identified to hydrolyze to sec-butanol by both acidic and basic mechanisms, with a mass balance/conversion factor of 2 moles of sec-butanol (actual experimental range 1.97 to 1.99) per mol of initial parent test item. The remaining central peroxydicarbonic acid was considered to degrade further, possibly through a series of highly unstable intermediates, to carbon dioxide under acidic conditions and potentially a mixture of carbon dioxide and oxygen under basic conditions.
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