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EC number: 231-609-1 | CAS number: 7651-02-7
- 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
Sediment toxicity
Administrative data
Link to relevant study record(s)
Description of key information
Two endobenthic organisms. the worm Lumbriculus variegatus and the abundant nematode Caenorhabditis elegans, were used to determine a potential sediment toxicity of C20/22 ATQ. These sediment data are used for read-across to the registration substance SAPDMA.
Key value for chemical safety assessment
- EC10, LC10 or NOEC for freshwater sediment:
- 62.5 mg/kg sediment dw
Additional information
READ-ACROSS JUSTIFICATION TO C20/22 ATQ
As shown in the Aquatic Endpoint Summary the ecotoxicity profile of the registration substance as well as the read-across substance C20/22 ATQ are similar. The PNEC freshwater based on chronic data for the registration substance is 7.1 µg/L and for C20/22 ATQ 13 µg/L which means that the difference is within the variability / uncertainty of biota and test regimes of different lab. It is therefore justified to assume that the toxicity profile for both substances with respect to benthic organisms is similar as well and the available sediment studies from C20/22 ATQ can be used for read-across to the registration substance as well. In addition it is important to note that the PNEC freshwater sediment derived from the sediment data of C20/22 ATQ is 1.25 mg/kg dw and the PNEC freshwater sediment based on the Equilibrium Partitioning Method 1.94 mg/kg dw.
TOXICITY TO BENTHIC ORGANISMS OF C20/22 ATQ
The worm Lumbriculus has a NOEC being slightly lower than the NOEC of the nematode (62.5 mg/kg dw. and 250 mg/kg dw.). The NOEC of the worm Lumbriculus variegatus of 62.5 mg/kg dw. is choosen as a basis for the PNEC freshwater sediment.
Hypothesis for the analogue approach
This read-across is based on the hypothesis that source and target substances have similar toxicological properties because
· they are manufactured from similar or identical precursors under similar conditions
· they share structuralsimilarities with common functional groups: quaternary amines, amides, and saturated fatty acid chains with comparable length
· the metabolism pathway leads to comparable products (amine backbone and long chain fatty acids) and non-common products predicted to have no toxicological effects (long chain fatty acids).
Therefore, read-across from the existing ecotoxicity (sediment and soil) and environmental fate studies on the source substance is considered as an appropriate adaptation to the standard information requirements of the REACH Regulation for the target substance, in accordance with the provisions of Annex XI, 1.5 of the REACH Regulation.
The justification of the proposed read-across approach is elaborated in the next chapters.
1. Substance Identity
The target substance Stearic acid 3-(dimethylaminopropyl)amide is manufactured from octadecanoic acid and N, N-dimethylpropylenediamine.
The source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides is a quaternary ammonium chloride derived from fatty alcohol.
Table 1: Substance identities
|
Target substance |
Source substance |
Stearic acid 3-(dimethylaminopropyl) amide |
Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides |
|
mono constituent substance |
UVCB |
|
IUPAC name |
N-[3-(dimethylamino)propyl]octa-decanamide |
n.a. |
EC number |
231-609-1 |
271-756-9 |
CAS number |
7651-02-7 |
68607-24-9 |
Chain length distribution |
< C16: < 1.6% C16: < 7% C18: > 88.9% > C18: < 2.5% |
Mainly C20 and C22; <C20 in smaller amounts; C22 = main constituent |
Figure 1: Molecular structures of the target substance Stearic acid 3-(dimethylaminopropyl) amide and the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides
2. Analogue approach justification
The read-across hypothesis is based on structural similarity of target and source substances. Based on available experimental data, including key physico-chemical properties and data from long-term aquatic ecotoxicity studies, the read-across strategy is supported by a similar ecotoxicological profile of the substances.
The respective reliable data (RL 1 or 2) are summarised in the table 2; robust study summaries are included in the Technical Dossier in the respective sections.
Ecotoxicological data are summarised in the data matrix.
2.1 Structural similarity
a. Structural similarity and functional groups (Table 1, Figure 1)
The target substance Stearic acid 3 -(dimethylaminopropyl)amide is manufactured from octadecanoic acid and N,N-dimethylpropylenediamine. It is composed of mainly C18 amides (> 89.8%) of DMAPA and small amounts of the C16 amide (<7%).
The source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides is a quaternary ammonium chloride derived from fatty alcohol. The general chemical structure is R-N(Me)3+ Cl-, whereas the alkyl chain R is variable for the main components C20 and C22 but also shorter and longer C-chains (in smaller amounts). The major constituent is the C22 derivative.
The target substance and the main constituent C22 ATQ of the source substance have a similar number of carbon atoms, are both cationic surfactants (see also 2.1.c) and are strongly sorbing to solids due to ionic interactions and van der Waals forces.
b. Common breakdown products
In principle, the amide-bond of the target substance can be cleaved abiotically but the half-life for the hydrolysis is >>100 years (US EPA Hydrowin Model).
The metabolism that is expected to occur is for the target substance Stearic acid 3-(dimethylaminopropyl)amidethehydrolysis of the amide-bond by amidases. Metabolism would result in free fatty acids and di- or trimethylaminopropylamine. The free fatty acids enter normal metabolic pathways (e.g. degradation by the mitochondrial beta-oxidation process) and are therefore indistinguishable from fatty acids from other sources.
The most likely metabolism of the second source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides is oxidation of the alkyl chain.
Both substances were shown to be readily and ultimately biodegradable in an OECD 301B CO2 Evolution test. In addition the microbial metabolic pathway is the same for both substances as in the first step the alkyl chain is cleaved from the nitrogen forming the corresponding aldehyde and ammonium compound. The aldehyde is then oxidized to the fatty acid which is subsequently degraded by beta oxidation (Kees van Ginkel, Handbook of Surfactants, Volume F, 1995).
c. Differences
Chain length:
The target substance contains mainly C18 chains, whereas the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides consists of mainly C22 chains. However, the overall number of carbon atoms is similar resulting in a comparable molecular weight. Nevertheless, the target substance is slightly more soluble in water and has a slightly lower log Kow due to the more hydrophilic amide function. Long-term ecotoxicity data on both substances however, show comparable effect levels. Thus, it is assumed, that the impact of this difference on toxicity to sediment dwelling and soil organisms is negligible.
Methylation/quaternation:
The source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides is methylated during the manufacturing process resulting in the quaternised ammonium ion.
Stearic acid 3-(dimethylaminopropyl)amide) on the other hand is not methylated during the manufacturing process. However, based on physicochemical data (pKa) it is concluded that at physiological relevant pH, the substance is mostly protonated similarly resulting in a positively charged ammonium ion.
Amide:
In contrast to the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides, the target substance Stearic acid 3-(dimethylaminopropyl)amide) contains a polar amide function which may be susceptible to enzymatic hydrolysis.
3. Physicochemical properties
Table 2: Physicochemical properties
|
Target substance |
Source substance |
Endpoints |
Stearic acid 3-(dimethylaminopropyl)amide |
Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides |
Molecular weight |
368.64 g/mol |
375.5 - 432.209 g/mol |
Physical state at 20°C / 1013 hPa |
Solid (paste) |
Solid |
Melting point |
OECD TG 102
67.4°C |
OECD TG 102
> 220 - < 240 °C |
Boiling point |
OECD TG 103
412.3°C |
n.a. |
Surface tension |
ISO 4311, plate method
37.86 mN/m at 25°C and 0.22 g/L |
OECD TG 115, plate method
47mN/m at 25°C and0.01g/L (pure C22) |
Water solubility |
ISO 4311, plate method
CMC = 220 mg/L at 25°C |
ISO 4311, plate method
CMC = 10 mg/L at 25°C and pHca. 5.4 (C22) |
Log Kow |
EU method A.8, calculation based on solubility in n-Octanol and water
log Kow: 2.01 at 20°C, pH7 |
EU method A.8, calculation based on solubility in n-Octanol and water
Log Kow: 3.29 at 20°C, pH ca. 5.4 |
Vapour pressure |
OECD TG 104
3.4E-08 Pa at 20°C |
OECD TG 104 7.0E-05 |
The physical state of both substances is solid. The surface tension, water solubility and log Kow are in a comparable range. The vapour pressure of both substances is very low.
The similar physic-chemical properties – especially surface activity, similar water solubility and partition coefficients – of the target and source substance support the read-across approach.
4. Comparison of data from environmental fate endpoints
Table 3: Data matrix: environmental fate
|
Target substance |
Source substance |
Endpoints |
Stearic acid 3-(dimethylaminopropyl)amide |
Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides |
Biodegradation: screening test |
OECD TG 301 B
readily biodegradable (88% after 28 d, >60% within the 10 d window) |
OECD TG 301 B
readily biodegradable (ca. 70% after 28 d, ca. 48% within the 10 d window) |
Biodegradation in soil: simulation testing |
No data, read-across |
OECD TG 307
DT50 of 23 to 41 days at 20°C in different soils |
Adsorption / desorption
|
No data, read-across |
OECD TG 106
Koc> 950 - < 516 000 L/kg Log Koc> 3 - < 5.7 |
The target substance is readily biodegradable in an OECD 301B CO2 Evolution test fulfilling the 10d window. CO2 evolution was 88% after 28d and has reached the pass level of 60% after 16d.
The source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides was readily biodegradable in a screening test, but failed the 10 d window criterion.
In an Aerobic transformation study in soil with 14C-C22 ATQ rapid degradation was observed. The DT50 for the three soils tested were 23.2, 24 and 41.4 d at 20°C. The Median for the 3 soils at 12 deg C is 45.5 d.
Sorption behaviour of the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides was measured in three different soils, one sediment and one secondary sludge. The Freundlich isotherms for the different matrices are non-linear (1/n < 1).
C22-Trimethylammonium Chloride adsorption isotherms could be described by the Freundlich equation. KFoc(ads) values were 19.8E03 L/kg (Cranfield 164 soil), 516E03 L/kg (Cranfield 277 soil), 52.8E03 L/kg (Cranfield 299 soil), 17.4E03 L/kg (SW sediment) and 0.95E03 L/kg (Tilburg sludge).
Overall, based on structural similarity, and comparable physico-chemical properties, the results of the environmental fate studies conducted with the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides can be used in a read-across approach for the target substance Stearic acid 3-(dimethylaminopropyl)amide.
5. Comparison of data from ecotoxicological endpoints
Table 4: Data matrix: ecotoxicity studies
|
Target substance |
Source substance |
Endpoints |
Stearic acid 3-(dimethylaminopropyl)amide |
Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides |
Short-term toxicity to fish |
OECD TG 203 Oncorhynchus mykiss; tapwater
96 h LC50 > 0.1 and <1 mg/L |
Not used in this read-across |
Long-term toxicity to fish |
OECD TG 212 Danio rerio; natural river water
9 d NOEC =0.1mg/L (abnormal behaviour) |
OECD TG 212 Danio rerio; natural river water
9 d NOEC =0.243mg/L (Hatch, Growth & Fry survival) |
Short-term toxicity to aquatic invertebrates |
OECD TG 202 Daphnia magna; natural river water
48 h EC50 =381µg/L (95% c.i.62.5 - 345 µg/L) |
Not used in this read-across |
Long-term toxicity to aquatic invertebrates |
OECD TG 211 Daphnia magna; natural river water
21 d NOEC =200µg/L (mortality) |
OECD TG 211 Daphnia magna; natural river water
21 d NOEC =128µg/L (reproduction) |
Toxicity to algae |
OECD TG 201 Desmodesmus subspicatus; natural river water
72 h EC50 =140 µg/L (95% c.i.130 – 154µg/L) 72h EC10 = 70.8 µg/L (95% c.i.62.7 – 78.7 µg/L) |
OECD TG 201 Desmodesmus subspicatus; natural river water
72 h EC50 =3.48mg/L (95% c.i.3.28 - 3.70 mg/L) 72 h EC10 =0.927mg/L (95% c.i.0.798-1.07 mg/L) |
sediment toxicity: long-term
|
No data, read-across |
OECD TG 225 Lumbriculus variegates 28 d EC50 =169mg/kg sediment dw (reproduction) 28 d NOEC =62.5mg/kg sediment dw (reproduction) |
|
|
Draft ISO/DIS 10872 Caenorhabditis elegans
96 h NOEC =250mg/kg sediment dw (mortaliy, fertility, reproduction, growth) |
toxicity to soil macroorganisms except arthropods: short-term |
No data, read-across |
OECD TG 207 Eisenia fetida
14 d NOEC =1 000 mg/kg soil dw (mortality, biomass, development) |
toxicity to soil macroorganisms except arthropods: long-term
|
No data, read-across |
OECD TG 222 Eisenia fetida
54 d NOEC =250mg/kg soil dw (eproduction, mortality and body weight) |
toxicity to terrestrial arthropods: long-term
|
No data, read-across |
ISO 11267 Folsomia candida
28 d NOEC =500mg/kg soil dw (mortality, reproduction) |
toxicity to soil microorganisms |
No data, read-across |
OECD TG 216 Soil microorganisms
28 d EC50 =76mg/kg soil dw (95% c.i.66.0 - 84.3mg/kg soil dw) (nitrate formation rate) 28 d EC10 =15mg/kg soil dw (95% c.i.12-38mg/kg soil dw) (nitrate formation rate) 28 d NOEC = 10 mg/kg soil dw (nitrate formation rate) |
The effect levels in the long-term studies with fish and daphnia were similar for the target substance Stearic acid 3-(dimethylaminopropyl)amide and the source substance Quaternary ammonium compounds, C20 -22 -alkyltrimethyl, chlorides, differing by a factor of 2.4 and 1.5, respectively. These ratios are well within the boundaries on variability / uncertainty accepted e. g. for reference substances.
The ratio for ErC10 (72h) for the target substance Stearic acid 3-(dimethylaminopropyl)amide and the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides is 12.9 and higher than expected. Nevertheless, variability within approx. one order of magnitude is not uncommon between different laboratories. Overall, based on structural similarity, comparable physico-chemical properties, and similar results in the long-term aquatic toxicity studies, the results of the ecotoxicity studies on sediment and soil organisms conducted with the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides are also valid forthe target substance Stearic acid 3-(dimethylaminopropyl)amide.The remaining uncertainty is addressed by applying the appropriate assessment factors.
6. Classification and labelling
Table 3: Classification and labelling for target and source substances
Classification Endpoints |
Target substance Stearic acid 3-(dimethylaminopropyl) amide |
Source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides |
Physical hazards |
No classification required |
No classification required |
Hazards to the aquatic environment: acute |
Aquatic Acute 1, M factor: 1 |
Aquatic Acute 1,M factor: 1 |
Hazards to the aquatic environment: chronic |
Aquatic Chronic 2 |
Aquatic Chronic 2 |
No classification is required for physical hazards for both, the target and the source substance.
The target substance as well as the source substance are classified as Aquatic Acute 1 with an M factor of 1 and as Aquatic Chronic 2. Neither substance is regarded as PBT or vPvB.
Classification with regard to human health effects is not relevant for this read-across approach, as only ecotoxicity and environmental fate endpoints are assessed.
7. Conclusion
The physico-chemical and structural similarities between of the source and the target substances as presented above support the read-across hypothesis. Adequate and reliable scientific information (similar results were obtained in the long-term aquatic toxicity studies, which are available for both, the target and the source substance) indicates that the source and target substances have similar ecotoxicity profiles.
Based on the available data it can be concluded that:
- the results of the environmental fate studies conducted with the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides can be used in a read-across approach forthe target substance Stearic acid 3-(dimethylaminopropyl)amide
- the ecotoxicity data for the sediment and soil compartment available for the source substance Quaternary ammonium compounds, C20-22-alkyltrimethyl, chlorides can be used in read-across to the target substance Stearic acid 3-(dimethylaminopropyl)amide. This approach is supported when comparing the PNEC sediment and PNEC soil with the respective PNECs derived with the Equilibrium partitioning method.
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.
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