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EC number: 203-026-2 | CAS number: 102-36-3
- 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
Link to relevant study record(s)
- Endpoint:
- hydrolysis
- Type of information:
- other: expert statement based on an experimental study conducted with the closely related 4-chlorophenyl isocyanate (CAS 104-12-1)
- Adequacy of study:
- supporting study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: expert statement based on common reactivity of phenyl isocyanates and
- Justification for type of information:
- It is commonly known that phenyl isocyanates are prone to hydrolysis. The isocyanate carbon as excellent electrophile can easily be attacked by water as nucleophile. Adding water results in a carbamic acid, which is unstable. Carbamic acids quickly lose carbon dioxide to give an amine. (Clayden et. al, 2009)
- Executive summary:
Different scientific sources[1,2] describe the following hydrolysis mechanism for phenyl isocyanates: The isocyanate carbon as excellent electrophile can easily be attacked by water as nucleophile. Adding water results in a carbamic acid, which is unstable. Carbamic acids quickly lose carbon dioxide to give an amine.
Based on this process and due to the lack of data on hydrolysis properties, results from the hydrolysis study of the structural analogue 4-chlorophenyl isocyanate are used to describe the hydrolysis properties of 3,4-dichlorophenyl isocyanate. The chemical structures are closely related, the only difference consists in an additional chlorine substituent present in position 3 in the structure of 3,4-dichlorophenyl isocyanate.
For 3,4-dichlorophenyl isocyanate the fast hydrolysis towards the product 3,4-dichloronaniline (95-76-1) is to be expected.
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- supporting study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: Comparable to guideline study with acceptable restrictions
- Principles of method if other than guideline:
- Investigation on stability in aqueous test solutions.
Comparable to guideline study. - GLP compliance:
- no
- Radiolabelling:
- no
- Analytical monitoring:
- yes
- Details on sampling:
- Samples were taken for analysis in intervals of 0 hour to 70 hours after incubation.
- Buffers:
- buffer solution pH 7.0: 296.3 ml NaOH 0.1 mol/l + 500 ml NaH2PO4 0.1 mol/l adjusted to 1000 ml with deionised water
- Details on test conditions:
- The test compound (3 mg) was weighed in an Erlenmeyer flask and dissolved in 300 ml of buffer solution ph 7 at ambient temperature (about 25 °C) by means of an ultrasonic bath (10 min) in order to obtain a concentration of 10 mg(l. the liquid was examined visually for undissolved particles, but wasobviously clear.
After preparation, the test solutionwas exposed to a temperature of 25 +/- 0.1 °C in a thermostat. The test war performed in buffer solution pH 7. the test solution and the head space were saturated. The Erlenmeyer flask was irradiated with a lamp of 11 Watt. The intnensity of light, measured on the surface of the flask, was 8000 lux. - Duration:
- 70 h
- pH:
- 7
- Temp.:
- 25 °C
- Remarks:
- The test compound itself could not be detected by the HPLC method used.
- Transformation products:
- yes
- No.:
- #1
- Details on hydrolysis and appearance of transformation product(s):
- Vigourous agitation and ultrasonification for 10 min in order to dissolve 4-chlorophenyl isocyanate (target concentration 10 mg/l, 0.0651 mMol/l) leads to a rapid degradation of the test compound. More than 50 % of the original amount of the test compound has been converted to 4-chloroaniline (4.39 mg/l, 0.0344 mMol/l) at time 0.
- pH:
- 7
- Temp.:
- 25 °C
- DT50:
- 7.3 h
- Type:
- (pseudo-)first order (= half-life)
- Conclusions:
- There is no test on hydrolysis for 3,4-dichlorophenyl isocyanate available. Results from the hydrolysis study of the structural analogue 4-chlorophenyl isocyanate are used to describe the hydrolysis properties of 3,4-dichlorophenyl isocyanate.
A test was performed in order to examine the stability under conditions simulating those in the environment (pH 7, presence of light and air). The results show that 4-chlorophenyl isocyanate hydrolyses rapidly, forming CO2 and 4-chloroaniline as primary hydrolysis products. Assuming a kinetic function of first order, a half life period of 7.3 h can be calculated (Bayer Industry services, 2004). - Executive summary:
There is no test on hydrolysis for 3,4-dichlorophenyl isocyanate available. Results from the hydrolysis study of the structural analogue 4-chlorophenyl isocyanate are used to describe the hydrolysis properties of 3,4-dichlorophenyl isocyanate.
A test was performed in order to examine the stability under conditions simulating those in the environment (pH 7, presence of light and air). The results show that 4-chlorophenyl isocyanate hydrolyses rapidly, forming CO2 and 4-chloroaniline as primary hydrolysis products. Assuming a kinetic function of first order, a half life period of 7.3 h can be calculated (Bayer Industry services, 2004).
Referenceopen allclose all
After 70 h, the test was terminated. At this time, the test compound was completely converted to 4-chloroaniline. The concentration of 4-chloroaniline (0.0651 nMol) equalled the initial concentration of 4-chlorophenyl isocyanate (0.0687 mMol).
Description of key information
Hydrolysis is not a data requirement for an Art. 18 >1000 t/a registration. Data were included for this endpoint as supporting information for the endpoint water solubility and the aquatic toxicity.
Different scientific sources describe the following hydrolysis mechanism for phenyl isocyanates: The isocyanate carbon as excellent electrophile can easily be attacked by water as nucleophile. Adding water results in a carbamic acid, which is unstable. Carbamic acids quickly lose carbon dioxide to give an amine.
Based on this process and due to the lack of data on hydrolysis properties, results from the hydrolysis study of the structural analogue 4-chlorophenyl isocyanate are used to describe the hydrolysis properties of 3,4-dichlorophenyl isocyanate. The chemical structures are closely related, the only difference consists in an additional chlorine substituent present in position 3 in the structure of 3,4-dichlorophenyl isocyanate.
A test comparable to guideline study (investigation on stability in aqueous test solutions) was performed in order to examine the stability under conditions simulating those in the environment (pH 7, presence of light and air). The results show that 4-chlorophenyl isocyanate hydrolyses rapidly, forming CO2 and 4-chloroaniline as primary hydrolysis products. Assuming a kinetic function of first order, a half life period of 7.3 h can be calculated (Bayer Industry services, 2004).
For 3,4-dichlorophenyl isocyanate the fast hydrolysis towards the product 3,4-dichloronaniline (95-76-1) is to be expected.
For further details please refer to chapter 13.2.
Key value for chemical safety assessment
Additional information
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