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EC number: 207-529-8 | CAS number: 479-27-6
- 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:
- From 05 April 2019 to 06 July 2020
- Reliability:
- 1 (reliable without restriction)
- Rationale for reliability incl. deficiencies:
- guideline study
Data source
Reference
- Reference Type:
- study report
- Title:
- Unnamed
- Year:
- 2 020
- Report date:
- 2020
Materials and methods
Test guidelineopen allclose all
- Qualifier:
- according to guideline
- Guideline:
- EU Method C.7 (Degradation: Abiotic Degradation: Hydrolysis as a Function of pH)
- Deviations:
- yes
- Remarks:
- All deviations stated as non-critical
- Qualifier:
- according to guideline
- Guideline:
- OECD Guideline 111 (Hydrolysis as a Function of pH)
- Deviations:
- yes
- Remarks:
- All deviations stated as non-critical
- GLP compliance:
- yes (incl. QA statement)
Test material
- Reference substance name:
- 1,8-naphthylenediamine
- EC Number:
- 207-529-8
- EC Name:
- 1,8-naphthylenediamine
- Cas Number:
- 479-27-6
- Molecular formula:
- C10H10N2
- IUPAC Name:
- naphthalene-1,8-diamine
- Reference substance name:
- 1,8-Naphthylendiamin
- IUPAC Name:
- 1,8-Naphthylendiamin
- Reference substance name:
- 1,8-Naphthylendiamin
- IUPAC Name:
- 1,8-Naphthylendiamin
- Details on test material:
- - Purity: 99.6 %
Constituent 1
Constituent 2
Constituent 3
- Specific details on test material used for the study:
- SOURCE OF TEST MATERIAL
- Source: Naoki Yamamoto, APIS & intermediates, API Corporation, 1-13-4 Uchi-kanda, Japan. Batch F71006
- Purity, 99.4%:
STABILITY AND STORAGE CONDITIONS OF TEST MATERIAL
- Storage condition of test material: Room temperature (20 ± 5°C), keep tightly closed and away from light, heat and all sources of ignition and oxidizing agents in a dry and well-ventilated area
- Homogeneous
- Stability: unknown
- Solubility <0.1 g/L water:
- Reactivity of the test material with the incubation material used (e.g. plastic ware): not known
TREATMENT OF TEST MATERIAL PRIOR TO TESTING
- The test item was ground finely before usage - Radiolabelling:
- no
Study design
- Analytical monitoring:
- yes
- Remarks:
- Analytical validation report VB17111002G926 is attached
- Details on sampling:
- - Sampling intervals for the parent (Tiers 1 and 2) and transformation products (Tier 3):
Tier 1 :
50.0 – 50.1 °C,
pH 4.0, 7.0 and 9.0
t=0h and t=120.5h (5d)
Tier 2:
12 °C - pH 4 - t=0, 21, 476, 575, 668 and 719 h
12 °C - pH 7 - t=0, 431, 530, 623, 694 and 790 h
12 °C - pH 9 - t=0, 139, 209, 360, 451, 550, 619, 669 and 714 h
25 °C - pH 4 - t=0, 164, 234, 476, 575, 668 and 719 h
25 °C - pH 7 - t=0, 340, 530, 603, 623, 649, 694 and 790 h
25 °C - pH 9 - t=0, 71.9, 115, 139, 169, 209, 285, 305, and 332 h
50 °C - pH 4 - t=0, 43.5,67.5, 73.6, 96.8, 140, 162, 194, 214, 234 and 310 h
50 °C - pH 7 - t=0, 117, 189, 333, 431, 530, 603, 623 and 694 h
50 °C - pH 9 - t=0, 23.5, 42.5, 48.6, 64.3, 71.8, 91.7, 116, 120 and 122 h
Tier 3 :
50 °C,
t=0h and t=5d for pH 9
t=0h and t=28d for pH 7
t=0h and t=10d for pH 4
- Sampling method: validation report VB17111002G926 (see attached)
- During hydrolysis turbidity in the samples occurred. Therefore, the following samples were centrifuged at 6000 rpm for 5 minutes:
Samples pH 4 at 50 °C with sampling times 213.5 h and 309.5 h. Samples pH 9 at 50 °C with sampling times 116.7 and 119.8 h. Samples pH 9 at 25 °C with sampling times 284.5, 304.5 and 331.5 h.
The supernatant of the centrifuged samples was used for the measurements.
Test item was filled up with hydrolysis buffer/water mixture 50/50 % (v/v) in a flask and treated with ultrasonic. These solutions with nominal concentration 380 mg/L were sterile filtered (with PTFE filters 0.2 µm pore size) into sterile vials.
The test vessels were then purged with sterile Argon to remove dissolved oxygen and then tightly closed with PTFE seals. The closed vials were incubated at a set temperature over a defined time period.
Samples were analysed before and after incubation - Buffers:
- - pH: 4
CH3COOH, 2 M 80 mL
CH3COONa 40 mL
Demineralised water ad 1000 mL
Final pH value, (adjusted with 2 M CH3COOH or 2 M NaOH) 4.0
- pH: 7
KH2PO4 8.7088 g
Demineralised water 500 mL
NaOH, 2 M 14.9 mL
Demineralised water ad 1000 mL
Final pH value, (adjusted with 2 M NaOH) 7.0
- pH: 9
H3BO3 3.0930 g
KCl 3.7296 g
Demineralised water 500 mL
NaOH, 2 M 10.75 mL
Demineralised water Ad 1000 mL
Final pH value, (adjusted with 2 M NaOH) 9.0 - Estimation method (if used):
- The concentration of 1,8-Diaminonaphthalene chip in the solution was determined using the following equation:
"c" _"measured" " [mg/L] =" "(Measured value - a)" /"b" * (100 % / QC Recovery Rate [%]) * dilution factor
with
a = intercept
b = slope
"QC recovery in %" = "measured concentration" /"nominal concentration" *100 %
QC Recovery rate is taken into account, if necessary.
Hydrolysis
Hydrolysis in % was calculated from the following equation:
"H = " ("1-" "c" _"t" /"c" _"0" )"*100%"
ct concentration at time t
c0 concentration at time 0
Kinetic Parameters
Hydrolysis refers to a reaction of a substance RX with water:
RX + H2O ROH + RX
Since H2O is present in great excess, kinetic usually can be considered as being first order. The corresponding equation for the rate of hydrolysis is calculated from:
rate = k * [RX]
A hydrolysis constant of pseudo-first order should be described as function of temperature. The rate constant kobs (k observed) at a defined pH and temperature is the mean of k at each time point t which is calculated using the following equation
"k" _"obs,i" "=" "1" /"t" "*ln" "c" _"0" /"c" _"t"
t time [h]
c0 concentration at time point 0 h
ct concentration at time point t
The half-life (t1/2) of the compound at a defined pH and temperature is calculated from:
"t" _"1/2" "=" "ln2" /"k" _"obs,i"
Calculation is performed using the Arrhenius equation, whose coefficients A and B are derived from the plot ln (k) vs. 1/T. Additionally, kobs was calculated as sum of acid catalysed, base catalysed and neutral hydrolysis:
kneutr hydrolysis rate at pH 7
kOH hydrolysis rate at pH 9
ln Ai intercept of each graph ln ki against 1/T
-Bi slope of each graph ln ki against 1/T
Ai exponential of ln Ai
T temperature in K
Slope and intercept for each pH were generated from linear regression of ln ki against 1/T:
ln ki = - Bi / T + ln Ai - Details on test conditions:
- Tier 1 concentrations
Duration of testopen allclose all
- Duration:
- 5 d
- pH:
- 9
- Temp.:
- 50 °C
- Initial conc. measured:
- 346 mg/L
- Remarks:
- Target dose of 380 mg/L represents a 91.0% recovery
- Duration:
- 5 d
- pH:
- 7
- Temp.:
- 50 °C
- Initial conc. measured:
- 368 mg/L
- Remarks:
- A target dose of 380 mg/L represents a 96.96% recovery
- Duration:
- 5 d
- pH:
- 4
- Temp.:
- 50 °C
- Initial conc. measured:
- 376 mg/L
- Remarks:
- A target dose of 380 mg/L represents a 99.05% recovery
- Number of replicates:
- 2
- Positive controls:
- no
- Negative controls:
- yes
Results and discussion
- Preliminary study:
- Tier 1 :
After five days (120.5 h) at 50 °C, the concentrations of the test item lay below 90% of the nominal start concentration at all three pH values. The test item was considered unstable and Tier 2 had to be conducted.
The highest decrease was at pH 9 with 81.2 %, whereas at pH 7 the decrease was only 14.5 %. - Test performance:
- Deviations from the study plan (and guideline) :
•Deviating from nominal temperature 50 ± 0.5 °C the lowest temperature was 48.4 °C for pH 7 due to a power failure. This was stated as uncritical, because deviation occurred for a short time only.
•Test duration was 33 d instead of 30 d for pH 7 hydrolysis buffer solutions at 12 °C and at 25 °C due to organizational reason. This was stated as uncritical, because the result is definite.
•For the evaluation at pH 4, 25°C only 2 points were used for evaluation, because only two sampling points lay in the range 10 – 90 % degradation. This was accepted, because otherwise the measurements of pH 4 could not have been used for further evaluation (calculations using the ARRHENIUS equation).
The deviations were signed and assessed by the study director on 07. Aug. 2019.
Additionally, the following deviation from the study plan was ascertained:
•Deviating from nominal temperature 50 ± 0.5 °C the temperature range was 49.7 – 50.8°C due to insufficient temperature control. This was stated as uncritical, because the deviation was small.
•Deviating from nominal temperature 50 ± 0.5 °C the lowest temperature was 47.4 °C for pH 4 (additional experiment) due to insufficient temperature control. This was stated as uncritical, because deviation occurred for a short time only.
•Deviating from the study plan for the preparation of some hydrolysis buffers instead of demineralised water, water with analytical grade was used due to an error. This was stated as uncritical, because the used water was analytical grade and therefore sufficient. - Transformation products:
- yes
Identity of transformation productsopen allclose all
- No.:
- #3
Reference
- Reference substance name:
- Unnamed
- IUPAC name:
- 2-Methyl-1H-perimidine
- CAS number:
- 5157-10-8
- Molecular formula:
- C12H10N2
- Molecular weight:
- 182.2
- SMILES notation:
- CC1=NC2=CC=CC3=C2C(=CC=C3)N1
- No.:
- #2
Reference
- Reference substance name:
- Unnamed
- IUPAC name:
- 1H-Perimidine
- CAS number:
- 204-02-4
- Molecular formula:
- C11H8N2
- Molecular weight:
- 168.2
- SMILES notation:
- C1=CC2=C3C(=C1)NC=NC3=CC=C2
- No.:
- #1
Reference
- Reference substance name:
- Unnamed
- IUPAC name:
- 1,1’-Hydrazonaphthyl-8,8’Diamine
- Molecular formula:
- C20H18N4
- Molecular weight:
- 314.4
- Details on hydrolysis and appearance of transformation product(s):
- Tier 3 - 50 °C for 5 days, pH 4, 7 and 9.
The content of one vial of each pH value was dissolved completely by addition of solvent. The clear solutions were measured with HPLC-UV-MS-MS using the same analytical method as for the HPLC-UV measurements.
The solutions, diluted after hydrolysis, were compared with freshly prepared test item solutions with nominal concentration 380 mg/L test item in the hydrolysis buffer/water mixtures (50/50 % (v/v)).
The relevant peaks were identified using the UV chromatograms. UV peaks were examined for their MS spectrum.
For the identification of degradation products > 10% of the original test item concentration, measurements with HPLC-UV-MS-MS, GC-MS and FT-IR were performed. Because sediment was formed after hydrolysis, test item solutions after hydrolysis were diluted with acetonitrile to give clear solutions for HPLC-UV-MS-MS measurements. Other flasks, containing test item solution after hydrolysis, were filtered and the residue was examined after dis-solution with GC-MS.
Substances, detected as degradation products, were similar for the three pH values.
The main substance in hydrolysed solutions was 1,8-Naphthalenediamine (the test substance) or a substance which shows very similar characteristics. Probably precipitation of the hydrated test item in dependence of pH, temperature and time occurred. This process was not reversible after ultrasonic treatment.
Several degradation products were detected with HPLC-UV-MS-MS and GC-MS. Products greater than 10%:
Only the presumed dehydration product 1,1’-Hydrazonaphthyl-8,8’Diamine (C20H18N4) was detected with UV signal higher than 10 % of the initial test item concentration. This was proposed by mass spectroscopy, but no analytical standard was available to confirm this assignment.
Products less than 10%:
1H-Perimidine (C11H8N2) was identified by comparison with a reference standard.
2-Methyl-1H-Perimidine was also suggested by mass spectroscopy, but no analytical standard was available to confirm this assignment.
The identity of other minor components were suggested by mass spectroscopy, but the proposed structures were considered to be implausible as hydrolysis products or were a reaction product with the acetone used for extraction.
A proposed hydrolysis pathway is attached.
Total recovery of test substance (in %)open allclose all
- % Recovery:
- 91
- pH:
- 9
- Temp.:
- 50 °C
- Duration:
- 0 h
- % Recovery:
- 96.96
- pH:
- 7
- Temp.:
- 50 °C
- Duration:
- 0 h
- % Recovery:
- 99.05
- pH:
- 4
- Temp.:
- 50 °C
- Duration:
- 0 h
Dissipation DT50 of parent compoundopen allclose all
- pH:
- 9
- Temp.:
- 12 °C
- Hydrolysis rate constant:
- 0.001 h-1
- DT50:
- 745.1 h
- St. dev.:
- 178
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 7
- Temp.:
- 12 °C
- Remarks on result:
- not determinable
- Remarks:
- Test item was stable under these conditions and so calculation of kinetic constants was not possible
- pH:
- 4
- Temp.:
- 12 °C
- Remarks on result:
- not determinable
- Remarks:
- Test item was stable under these conditions and so calculation of kinetic constants was not possible
- pH:
- 9
- Temp.:
- 25
- Hydrolysis rate constant:
- 0.003 h-1
- DT50:
- 202.1 h
- St. dev.:
- 64.5
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 7
- Temp.:
- 25 °C
- Remarks on result:
- not determinable
- Remarks:
- Test item was stable under these conditions and so calculation of kinetic constants was not possible
- pH:
- 4
- Temp.:
- 25 °C
- Hydrolysis rate constant:
- 0 h-1
- DT50:
- 3 791.6 h
- St. dev.:
- 549.6
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 9
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.014 h-1
- DT50:
- 48.7 h
- St. dev.:
- 10.1
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 7
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.002 h-1
- DT50:
- 450.2 h
- St. dev.:
- 104
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 4
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.004 h-1
- DT50:
- 189.5 h
- St. dev.:
- 93.5
- Type:
- (pseudo-)first order (= half-life)
- Details on results:
- Kinetic constants were not evaluated at 12 °C for pH 4 and pH 7 and at 25 °C for pH 7. The test item was stable under these conditions.
Because for pH 7 only one data point was evaluable (at 50°C), kobs at a temperature of 20 °C (293.15 K) was calculated using the ARRHENIUS equation based on the results of pH 4 and pH 9 only.
The hydrolysis constants obtained at 25 °C fit very well the ARRHENIUS equation, indicating that the reaction is indeed following pseudo-first order kinetics.
The hydrolysis mechanism is dependent from the pH value. The test item is most stable at pH 7 and most unstable at pH 9. Only at 50°C hydrolysis was determined over the test period at pH 7, whereas hydrolysis was determined at 12, 25 and 50°C for pH 9.
Using the ARRHENIUS equation, kobs and half-life of 1,8-Diaminonaphthalene chip at 20 °C (293.15 K) were calculated as:
kobs (293.15 K)= 0.002048 h-1
t1/2 (293.15 K) = 338.5 h
Applicant's summary and conclusion
- Validity criteria fulfilled:
- yes
- Conclusions:
- The hydrolysis of 1,8-Diaminonaphthalene chip was determined in three experiments (Tier 1, Tier 2 and Tier 3) according to the OECD 111 Guideline.
Tier 1
After five days (120.5 h), the concentrations of the test item lay below 90% of the start concentration at all three pH values (Tier 1) after incubation for 5 d at 50 °C. The test item was considered unstable and Tier 2 had to be conducted.
Tier 2
Evaluation of experiment 2 (Tier 2) showed temperature dependency of the hydrolysis.
Kinetic constants were not evaluated at 12 °C for pH 4 and pH 7 and at 25 °C for pH 7. The test item was stable under these conditions.
Using the experimentally determined kobs for each pH and temperature, temperature dependency was calculated.
Because for pH 7 only one data point was evaluable (at 50°C), kobs at a temperature of 20 °C (293.15 K) was calculated using the Arrhenius equation based on the results of pH 4 and pH 9 only. The hydrolysis constants obtained at 25 °C fit very well the Arrhenius equation, indicating that the reaction is indeed following pseudo-first order kinetics.
The hydrolysis mechanism is dependent from the pH value. The test item is most stable at pH 7 and most instable at pH 9. Only at 50°C hydrolysis was determined over the test period at pH 7, whereas hydrolysis was determined at 12, 25 and 50°C for pH 9.
Using the Arrhenius equation, kobs and half-life of 1,8-Diaminonaphthalene chip at 20 °C (293.15 K) were calculated as:
kobs (293.15 K)= 0.002048 h-1
t1/2 (293.15 K) = 338.5 h
Tier 3 - 50 °C for 5 days, pH 4, 7 and 9.
The solutions, diluted after hydrolysis, were compared with freshly prepared test item solutions with nominal concentration 380 mg/L test item in the hydrolysis buffer/water mixtures (50/50 % (v/v)).
The relevant peaks were identified using the UV chromatograms. UV peaks were examined for their MS spectrum.
For the identification of degradation products > 10% of the original test item concentration, measurements with HPLC-UV-MS-MS, GC-MS and FT-IR were performed.
Substances, detected as degradation products, were similar for the three pH values.
The main substance in hydrolysed solutions was 1,8-Naphthalenediamine (the test substance) or a substance which shows very similar characteristics.
Several degradation products were detected with HPLC-UV-MS-MS and GC-MS.
Products greater than 10%:
Only the presumed dehydration product 1,1’-Hydrazonaphthyl-8,8’Diamine (C20H18N4) was detected with UV signal higher than 10 % of the initial test item concentration. This was proposed by mass spectroscopy, but no analytical standard was available to confirm this assignment.
Products less than 10%:
1H-Perimidine (C11H8N2) was identified by comparison with a reference standard.
2-Methyl-1H-Perimidine (C12H10N2) was also suggested by mass spectroscopy, but no analytical standard was available to confirm this assignment.
A proposed hydrolysis pathway is attached. - Executive summary:
The hydrolysis of 1,8-Diaminonaphthalene chip was determined in three experiments (Tier 1, Tier 2 and Tier 3) according to the OECD 111 Guideline.
Tier 1
After five days (120.5 h), the concentrations of the test item lay below 90% of the start concentration at all three pH values (Tier 1) after incubation for 5 d at 50 °C. The test item was considered unstable and Tier 2 had to be conducted.
Tier 2
Evaluation of experiment 2 (Tier 2) showed temperature dependency of the hydrolysis.
Kinetic constants were not evaluated at 12 °C for pH 4 and pH 7 and at 25 °C for pH 7. The test item was stable under these conditions.
Using the experimentally determined kobs for each pH and temperature, temperature dependency was calculated.
Because for pH 7 only one data point was evaluable (at 50°C), kobs at a temperature of 20 °C (293.15 K) was calculated using the Arrhenius equation based on the results of pH 4 and pH 9 only. The hydrolysis constants obtained at 25 °C fit very well the Arrhenius equation, indicating that the reaction is indeed following pseudo-first order kinetics.
The hydrolysis mechanism is dependent from the pH value. The test item is most stable at pH 7 and most instable at pH 9. Only at 50°C hydrolysis was determined over the test period at pH 7, whereas hydrolysis was determined at 12, 25 and 50°C for pH 9.
Using the Arrhenius equation, kobs and half-life of 1,8-Diaminonaphthalene chip at 20 °C (293.15 K) were calculated as:
kobs (293.15 K)= 0.002048 h-1
t1/2 (293.15 K) = 338.5 h
Tier 3 - 50 °C for 5 days, pH 4, 7 and 9.
The solutions, diluted after hydrolysis, were compared with freshly prepared test item solutions with nominal concentration 380 mg/L test item in the hydrolysis buffer/water mixtures (50/50 % (v/v)).
The relevant peaks were identified using the UV chromatograms. UV peaks were examined for their MS spectrum.
For the identification of degradation products > 10% of the original test item concentration, measurements with HPLC-UV-MS-MS, GC-MS and FT-IR were performed.
Substances, detected as degradation products, were similar for the three pH values.
The main substance in hydrolysed solutions was 1,8-Naphthalenediamine (the test substance) or a substance which shows very similar characteristics.
Several degradation products were detected with HPLC-UV-MS-MS and GC-MS.Products greater than 10%:
Only the presumed dehydration product 1,1’-Hydrazonaphthyl-8,8’Diamine (C20H18N4) was detected with UV signal higher than 10 % of the initial test item concentration. This was proposed by mass spectroscopy, but no analytical standard was available to confirm this assignment.
Products less than 10%:
1H-Perimidine (C11H8N2) was identified by comparison with a reference standard.
2-Methyl-1H-Perimidine (C12H10N2) was also suggested by mass spectroscopy, but no analytical standard was available to confirm this assignment.
A proposed hydrolysis pathway is attached.
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