Registration Dossier
Registration Dossier
Data platform availability banner - registered substances factsheets
Please be aware that this old REACH registration data factsheet is no longer maintained; it remains frozen as of 19th May 2023.
The new ECHA CHEM database has been released by ECHA, and it now contains all REACH registration data. There are more details on the transition of ECHA's published data to ECHA CHEM here.
Diss Factsheets
Use of this information is subject to copyright laws and may require the permission of the owner of the information, as described in the ECHA Legal Notice.
EC number: 221-375-9 | CAS number: 3081-14-9
- 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
Endpoint summary
Administrative data
Description of key information
Additional information
Summary of ecotox data for the PPDs (parent compounds)
An overview
over the relevant ecotoxicological key data for the PPDs is given in the
following table.
Table: Results of all available ecotoxicity tests, except those with
reliability 3 (references are explained in the IUCLID dossier and in the
CSR)
6PPD |
7PPD |
77PD |
44PD |
||
short-term toxicity to fish |
96h-LC50 0.028 mg/L, MITI 1999 96h LC50 0.29 mg/L, (MITI 2001) 96h LC0 5 mg/L (Bayer 1984) |
96h LC50=0.3 mg/L, Monsanto 1983 96h LC50=0.42 mg/L, Monsanto 1983 96h LC50=0.4 mg/L, Monsanto 1981 |
96h-LC50 0.06 mg/L, Monsanto 1981 96h-LC50 0.14 mg/L (Monsanto 1981) |
0.24 mg/L (Monsanto 1981)
96h-LC50 0.368 mg/L (MITI 2010) |
|
long-term toxicity to fish |
NOEC 0.0037 mg/L, (MITI 2002) |
|
|
||
short-term toxicity to aquatic invertebrates |
48h-EC50 0.23 mg/L, (MITI 1999) 48h-EC50 0.51 mg/L, (Monsanto 1984) 48h-EC50 0.79 mg/L, (Monsanto 1984) 48h-EC50 0.82 mg/L, (Monsanto 1978) |
48h LC50=0.2 mg/L, 48h LC50=0.21 mg/L, Monsanto 1981
|
48h LC50 = 0.37 mg/L 48h LC50 = 1.7 mg/L |
EC50 0.54 mg/L (MITI 2010)
EC50 1.4 mg/L (Monsanto 1981) |
|
long-tem toxicity to aquatic invertebrates |
|
|
|
||
toxicity to aquatic algae and cyano bacteria |
72h-EC50 4.6 mg/L |
|
|
EC50 0.939 mg/L, NOEC 0.0958 mg/L (MITI 2010) |
|
* Study performed with 6QDI
Fish
Typical LC50 values in acute fish tests are in the range of 0.1 to 5 mg/L. Two results, one from a test with 6PPD and one from 77PD are the most sensitive ones (0.028, 0.06 mg/L). Selecting the results of these 2 tests for read-across represents the worst case and is therefore acceptable. The long-term fish test, performed with 6PPD yields a NOEC of 0.0037 mg/L. Typically, the ratio of the fish short-term and the long-term results (EC50/NOEC) is about 10 (Ahlers, J., 2006). Thus, this low NOEC-value is considered as conservative and read-across to the other PPDs including 77PD is justified.
Aquatic invertebrates
Short-term tests have been performed with each individual PPD yielding EC50-values in the range of 0.2 to 1.7 mg/L.
Indivual values from tests with 77PD (EC50 0.37 and 1.7 mg/L) and from
the study performed with 4-HDPA (EC50 0.69 mg/L) is within this range (Table below). This supports strongly the read-across approach for the long-term test performed with 4-HDPA also for 77PD although 4 -HDPA is not a hydrolysis product of 77PD but a similar substance. The NOEC of 0.028 mg/L is even more conservative considering the ratio of the daphnids short-term and long-term results (EC50/NOEC) of about 7 (Ahlers, J., 2006).
Aquatic algae and cyano bacteria
Studies are available with 44PD and from 6QDI, the oxidized form of 6PPD. The results (EC50 0.9 to 1.5 mg/L) show that algae are the least sensitive trophic level. The effect values of 4-HPDA (Table below) are n the same order of magnitude and thus read-across is justified..
Ecotoxicity of Degradation products
Due to the rapid hydrolysis, also the degradation products are evaluated concerning their effects in aquatic organisms. An overview over the relevant ecotoxicological key data for the degradation products (from hydrolysis and biodegradation reports) of the PPDs is given in the table below. 4 -HDPA and N-phenyl-p-benzoquinone monoimine are not hydrolysis products of 77PD but from 6PPD and 7PPD and thus also used for read-across.
Table: Results of ecotoxicity tests (references are explained in the IUCLID dossier and in the CSR); Green fields contain results of experimental tests.
4-HDPA CAS 122-37-2 |
N-Phenyl-p-benzoquinone monoimine CAS 2406-04-4 |
N-2-,5-Dimethylpentyl-p-aminophenol |
p-Benzo-quinone |
p-Hydro-quinone |
1,3-Dimethyl-butylamine or 1,4-Dimethyl-pentylamine |
|
short-term toxicity to fish |
LC50 12.7 mg/L calc. ECOSAR |
LC50 1.78 mg/L calc. ECOSAR |
LC50 2.1 mg/L calc. ECOSAR |
96h-LC50 0.045 mg/L (DeGraeve 1980) |
96h-LC50 0.17 mg/L (OECD 2002) (Wellens 1982) |
read-across with sec. Butylamine: LC50 <68 mg/L OECD 2011 |
read-across with n-Octylamine: LC50 5.19 mg/L OECD 2011 |
||||||
|
||||||
long-term toxicity to fish |
|
|
|
|
|
|
short-term toxicity to aquatic invertebrates |
EC50(48h) 0.69 mg/L (Currenta 2010) |
3.8 mg/L calc.ECOSAR |
1.4 mg/L calc.ECOSAR |
|
48h-EC50 0.134 mg/L (Crisinel 1994) |
read-across with sec. Butylamine: EC50 40 mg/L OECD 2011 |
48h-EC50 5.3 mg/L calc. ECOSAR |
read-across with n-Octylamine: EC50 1.9 mg/L |
|||||
OECD 2011 |
||||||
long-tem toxicity to aquatic invertebrates |
NOEC (21d) 0.028 mg/L Currenta 2010 |
|
|
NOEC0.0029 mg/L (ECHA dissemin.) |
|
|
|
||||||
toxicity to aquatic algae and cyano bacteria |
EC50 2.6 mg/L NOEC 0.23 mg/L, (Currenta 2010) |
51.1 mg/L calc.ECOSAR |
5.3 mg/L calc.ECOSAR |
|
3d-EC50 0.335 mg/L (OECD 2002) (Devillers 1990) |
read-across with sec. Butylamine: EC50 2.03 mg/L |
96h-EC50 23.4 mg/L calc.ECOSAR |
read-across with n-Octylamine: LC50 0.23 mg/L OECD 2011 |
Generally the effect values of the aliphatic amine components are higher and therefore covered by the ecotoxicity of the parent substances and the aromatic degradation products.
Fish
Obviously, fish is the most sensitive organism for the family of PPDs and their degradation products. The lowest effect value was found for p-hydroquinone (0.044 mg/L) which is rather similar to the values for p-benzoquinone (0.045 mg/L) and for 6PPD (0.028 mg/L).
For 4-HDPA and N-phenylbenzoquinone-imine only calculated values are available. The calculated values should be used only for a rough estimation due to the high uncertainty of the method. However they show a trend: The effect values of these three intermediate compounds to fish are at a higher level and there is no indication for a higher toxicity exceeding those for 6PPD or p-hydroquinone.
Aquatic invertebrates
The lowest effect value in acute tests was found for p-hydroquinone (0.134 mg/L) which is close to the values for the PPDs (0.2 to 1.9 mg/L) and 4-HDPA (0.69 mg/L).
For 4-HDPA, N-phenylbenzoquinone-imine and 1,4-dimethylpentyl-p-aminophenol, calculated values are available. For these calculated values, the same goes true as for the calculated values for fish: They should only be used only for a rough estimation due to the high uncertainty of the method. However they show a trend: The effect values of these three intermediate compounds to daphnids are at a higher level and there is no sign for a higher toxicity than found for the PPDs or their degradation products.
There is an indication of one long-term result (NOEC 0.0029 mg/L; expressed in 77PD equivalents 0.007 mg/L) from p-hydroquinone (ECHA dissemination tool). This effect value is even lower than the chronic value of 4-HDPA (NOEC 0.028 mg/L) and can therefore be considered as most the conservative one which should cover the whole range of PPDs. Using the NOEC value of 0.007 mg/L and the lowest acute value (0.134 mg/L), the ratio of the daphnids short-term to long-term results (EC50/NOEC) of about 19 is more conservative as the value of 7 (Ahlers, J., 2006).
Aquatic algae and cyano bacteria
Studies are available with p-hydroquinone and with 4-HDPA. The results show that algae are the least toxic trophic level.
Conclusion on ecotoxicityand selection of key values
Experimental and calculated values for the four PPDs and for six ecotxicological relevant degradation products were evaluated and the relevant lowest effect concentrations were taken as key values:
Table: Key values of ecotoxicological endpoints:
Read-across based on |
Key values |
||
short-term toxicity to fish |
6PPD |
LC50 0.028 mg/L |
|
long-term toxicity to fish |
6PPD |
NOEC 0.0037 mg/L |
|
short-term toxicity to aquatic invertebrates |
7PPD |
EC50 0.2 mg/L |
|
p-Hydroquinone |
EC50 0.134 mg/L |
||
|
|||
long-tem toxicity to aquatic invertebrates |
p-Hydroquinone |
NOEC 0.007 mg/L |
|
toxicity to aquatic algae and cyano bacteria |
p-Hydroquinone |
EC50 0.335 mg/L |
|
44PD |
NOEC 0.0958 mg/L |
Effects of Tyre wear particles (TWP)
Tyres typically contain about 1% of a PPD antioxidant. By abrasion of tyres, emission of TWPs to the environment occurs. Two studies with TWPs are available. One study for acute effects in auqatic organisms and one study for chronic effects in aquatic and benthic organisms have been performed (Marwood 2010, Marwood, 2011). The results are summarised in the following Table:
Type |
Effect values |
||
short-term toxicity to fish |
LC50 |
>10000 mg/LE |
|
long-term toxicity to fish |
EC0 |
>10000 mg/L |
|
short-term toxicity to aquatic invertebrates |
EC50 |
5000 mg/L |
|
long-tem toxicity to aquatic invertebrates |
EC10 |
>10000 mg/L |
|
toxicity to aquatic algae and cyano bacteria |
EC50 |
>10000 mg/L |
|
long-tem toxicity to sediment dwelling organisms (Hyalella Azteca) |
EC0 |
>10000 mg/L |
|
long-tem toxicity to sediment dwelling organisms (Chironomus tentans) |
EC10 |
10000 mg/L |
As a conclusion, no effects have been observed in any acute of chronic tests.
In parallel to the acute tests,TWP were incubated with moderately hard water at 44C for 72 h, and the resulting leachate was analyzed for select organic constituents.
(results of relevant materials of the PPD's)
Parameter | Leachate blank [mg/L] | TRWP Leachate [mg/L] |
N-(1,3-dimethylbutyl)-N'-phenylbenzene-1,4-diamine (6PPD) | < 1 | < 0.3 |
N-Isopropyl-N-phenyl-p-phenylenediamine (IPPD) |
< 1 | < 0.3 |
N,N'-Bis(1,4 -dimethylpentyl)-p-phenylenediamine (77PD) | 1.7 - 5* | <38 or (26 mg/L) |
*Detected but not quantifiable; range represents range of limit of detection and limit of quantification
Discussion of the leachate analytis:
• The authors measured the concentration of selected substances, which are typical constituents of TWP, in a leachate resulting of the incubation of TWP in water at 44°C for 72h. This data displays a realistic approach in describing the entry of TWP substances into the environment. Among others the concentration of 6PPD was measured which can be used due to the chemical similarity as read-across for 7PPD. A concentration < 0.3 mg/L for 6PPD was determined. As a conservative approach an actual concentration of 0.15 mg/L (half LOQ) is used for further assessment. A nominal concentration of 10000 mg/L TWP was applied into the study and as a concentration of 1% is assumed for 77PD (see above) the total nominal amount of the substance is 100 mg/L. Considering the measured concentration of the substance in the leachate of 0.15 mg/L in conclusion 0.15% of the substance is released into the environment (equals a factor of 0.0015). Therefore the predicted environmental concentration can be refined with this factor to display realistic environmental concentrations of the substance.
• The concentration of 77PD in the leachate of TWP was also measured in the study of Marwood (2011) but was not taken into consideration as this value seems not to be plausible. Two different concentration values for 77PD were reported, 26 mg/L and > 38 mg/L, that are contradictory. There is no explanation in the text dealing with this discrepancy. Further 77PD was detected in the leachate blank but could not be quantified. In conclusion the above mentioned discrepancies were the reason for omitting the measured values for 77PD as it is an artefact. This assumption is supported by the outcome of the ecotoxicity where an effect with 77PD would have been expected. It is assumed that the PPDs are used in the same concentration range in TWP and the water solubility of 6PPD and 77PD is very similar. Therefore the measured value for 6PPD, the leading substance for the PPD family, was also used for 77PD and 7PPD as read-across.
Toxicity to microorganisms:
A test with activated sludge with a duration fo 3 hours was performed according to the OECD Guideline 209. For 77PD an EC50 of 57 mg/L was observed (Bayer, 1989).
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.
Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.