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EC number: 940-123-5 | CAS number: 866889-74-9
- 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
No experimental terrestrial toxicity data are available for C16-18 DMAPA amidoamine. However, studies with the read-across substance C20/22ATQ are available. A justification for read-across is given below.
Toxicity to soil macroorganisms except arthropods
Effects of C20/22ATQ on mortality, biomass and reproduction of the earthworm species Eisenia fetida (Savigny) were determined according to the guidelines DIN ISO 11268-2 (1998), OECD 222 (2004) and BBA (1994). The study was conducted under static conditions over 8 weeks with three different application rates of 250 – 500 - 1000 mg/kg soil dry weight (DW), which were thoroughly mixed with artificial soil containing 10 % peat. Four replicates per control and test item concentration were examined. Replicates contained 10 test organisms with an individual weight of 0.30 to 0.60 g each.
After 28 days no significant mortality and no significant pathological symptoms or changes in the behaviour of adult earthworms were observed at all tested substance concentrations compared to the control. However, compared to the control the increase in body weight of the adult earthworms was significantly reduced at the highest test item concentration of 1000 mg/kg soil dry weight. After further four weeks the reproduction rate (average number of juveniles) came to 420 in the untreated control group and ranged between 211 and 391 in the test item groups. Compared to the control the reproduction was significantly reduced at the test item concentrations of 500 and 1000 mg/kg soil DW.
Under the conditions of this study, C20/22 ATQ had significant effects on biomass and reproduction of adult earthworms at the test item concentrations of 500 and 1000 mg/kg soil DW.
The No Observed Effect Concentration of C20/22 ATQ with respect to mortality, biomass and reproduction of Eisenia fetida was observed after 8 weeks of exposure to artificial soil (containing 10 % peat) at the application rate of 250 mg/kg soil DW.
The acute effects of C22-trimethylammonium chloride on the earthworm Eisenia fetida (Savigny 1826) were determined according to the OECD Guideline 207 and DIN ISO 11268-1 The study was conducted with the nominal concentration of 1000 mg test substance/kg soil dry weight (DW) over a time of 14 days. 40 test organisms with an individual weight between 0.30 - 0.60 g, divided into four replicates, were tested per concentration and control in artificial soil as described by the guideline. No significant mortality was observed at the limit test item concentration 1000 mg test substance/kg soil DW after 14 days of exposure. No pathological symptoms or changes in behaviour of the earthworms were seen neither in the control group nor in the tested limit concentration. Mean body weight loss during the study was below 20% in both groups and thus, biologically not significant.
Toxicity to terrestrial arthropods
The effects of C20/22 ATQ on the reproduction of Folsomia candida in artificial soilwere examined in a laboratory study. The study was carried out based on ISO 11267 (1999) and OECD Draft (2008).
The aim of the test was to determine the effects of the test item on the reproduction of Folsomia candida in artificial soil by cutaneous and alimentary uptake. The test item C20/22 ATQ was incorporated once into artificial soil with the test item concentrations 62.5 – 125 - 250 – 500 – 1000 mg/kg DW. The control was artificial soil without the test or reference item. Additionally a solvent control was tested. Folsomia candida (12 days old) were placed into artificial soil. For the control and solvent control 8 replicates and for the test item 5 replicates were tested. In each replicate 10 juveniles were inserted. During exposure springtails were fed with granulated dry yeast. After 28 days, mortality and reproduction were assessed.
Test item |
C20/22 ATQ |
|
Test object |
Folsomia candida |
|
Exposure |
Artificial soil |
|
Adult mortality |
Reproduction |
|
LOEC [mg/kg DW] |
1000 |
1000 |
NOEC [mg/kg DW] |
500 |
500 |
LD50/ EC50[mg/kg DW] |
> 1000 |
> 1000 |
The validity of the study was evaluated according to ISO 11267 (1999) and OECD Draft (2008). Control mortality should be 20 %. In this study the mean control mortality (pooled controls) was 13.8 %. The reproduction rate should be >/=100 instars per control replicate. In this study the reproduction rate was between 245 and 670 instars per control replicate (pooled control).The coefficient of variation of the reproduction rate in the control should be 30.0 %. In this study the coefficient of variation in the pooled controls was 25 %.Thus, this study was considered to be valid.
Toxicity to soil microorganisms
C20/22 ATQ was tested in a Nitrogen Transformation Testaccording to OECD Guideline 216.
After 7 days of exposure the EC25-value for inhibition of the nitrate-N formation rate in soil was 22.0 mg/kg soil dry weight. After 7 days the inhibition of nitrate transformation was below 50 % at all test item concentrations resulting in an EC50-value > 500 mg/kg soil dry weight. The NOEC for nitrate transformation in soil on day 7 was determined to be 12.8 mg/kg soil dry weight.
After 14 days of exposure the EC25-value for inhibition of the nitrate-N formation rate in soil was 32 mg/kg soil dry weight. The EC50 for inhibition of the nitrate transformation was determined to be at 176 mg/kg soil dry weight. The NOEC for nitrate transformation in soil on day 14 was set at 12.8 mg/kg soil dry weight.
After 28 days of exposure the following EC-values for inhibition of the nitrate-N formation rate were determined: EC12.5: 16.6 mg/kg soil dry weight, EC25: 49.5 mg/kg soil dry weight, EC50: 76.0 mg/kg soil dry weight. The NOEC for nitrate transformation in soil on day 28 was set 12.8 mg/kg soil dry weight.
Toxicity to terrestrial plants
From read-across acute and chronic earthworm, chronic collembola and a soil microorganism study is available which means that 2 out of 3 trophic levels of the soil compartment are well covered with soil microorganism being the most sensitive endpoint (NOEC 28 d 10 mg/kg dw). Based on this comprehensive data set a terrestrial plant toxicity study is not warranted.
1. Read-across hypothesis and justification
This read-across is based on the hypothesis that source and target substances have similar ecotoxicological properties because
· they are manufactured from similar resp. identical precursors under similar conditions
· 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).
· of their structural similarities: target and source substances are comprised of a hydrophobic (alkyl) and hydrophilic (positively charged ammonium) part; due to theses structural elements they form micelles and have surface active properties.
· of their similar molecular weight, physicochemical properties and similar ecotoxicological profile in aquatic tests
Therefore, read-across from the existing ecotoxicological studies on the source substances is considered as an appropriate adaptation to the standard information requirements of Annex VII 9.1.1, 9.1.2, 9.2.1, Annex VIII 9.1.3, 9.1.4, Annex IX 9.1.5, 9.1.6, 9.2.1, and 9.4 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.
2. Justification for read-across
2.1 Substance Identity
Table 1: Substance identities
|
Source substances |
Target substance |
|
Stearic acid 3-(dimethylaminopropyl)amide |
N,N,N-trimethyl-C20-22-(even numbered)-alkyl-1-aminium chloride; C20/22- alkyltrimethylammonium chloride (C20/22 ATQ) |
C16-18 DMAPA amidoamine |
|
Substance type |
mono constituent substance |
UVCB |
UVCB |
CAS number |
7651-02-7 |
68607-24-9 |
|
EC number |
231-609-1 |
271-756-9 |
|
Chain length distribution |
< C16: < 1.6% C16: < 7% C18: > 89.8% > C18: < 1.6% |
C16: <1% C18: ca. 4% C20: ca. 12% C22: ca. 82% C24: ca. 1% |
C14: <= 5 % C16: 25-35 % C18: >= 61 % |
DMAPA |
<0.002% |
N/A |
<=0.01% |
2.1 Substance Identity
Substance descriptions
The target substance C16-18 DMAPA amidoamine is a UVCB substance manufactured from saturated C16-18 fatty acids and N, N-dimethylpropylenediamine (DMAPA). It is composed of C16 and C18 amides of DMAPA, with C18 being the larger part (>/= 61%)
The source 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 C20/22 ATQ is manufactured from behenyl alcohol and dimethylamine, resulting in the corresponding tertiary amine dimethylalkylamine. In step two, the dimethylalkylamine is treated with methylchloride at elevated pressure to form the quaternary ammonium chloride.
2.2 Common breakdown products
The source substance Stearic acid 3-(dimethylaminopropyl)amide is the main component of the UVCB target substance C16-18 DMAPA amidoamine. The only difference is the chain length distribution: the target substance also contains a significant amount of the C16 amide.
This is not considered to be of relevance for metabolism.Both substances are amides which after resorption may be hydrolysed by amidases resulting in free fatty acids and DMAPA. The carboxylic acids then are further degraded by the mitochondrial beta-oxidation process (for details see common text books on biochemistry). The fatty acids enter normal metabolic pathways and are therefore indistinguishable from fatty acids from other sources including diet. The amine compounds are not expected to be further metabolised, but excreted via the urine mainly unchanged.
As no ecotoxicological data are available for the target substance C16-18 DMAPA amidoamine, but only its main constituent Stearic acid 3-(dimethylaminopropyl)amide, comparison of ecotoxicological data of the second source substance C20/22 ATQ is only possible to the latter. However, as explained above, the small amount of additional C16 is not expected to have any relevant influence on toxicity.
Both, target and source substances are cationic surfactants and are strongly sorbing to solids due to ionic interactions and van der Waals forces. Both substances are also 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 oxidised to the fatty acid which is subsequently degraded by beta oxidation (Kees van Ginkel, Handbook of Surfactants, Volume F, 1995).
2.3 Common structural elements
Target and source substances are comprised of a hydrophobic (alkyl) and hydrophilic (positively charged ammonium) part. Due to theses structural elements they form micelles and have surface active properties.
2.4 Differences
The slight differences in fatty acid chain length (higher percentage of C16 in the target substance vs. corresponding higher percentage C18 in the source substance) are not considered to be of relevance for ecotoxicity.
C16-18 DMAPA amidoamine as well as Stearic acid 3-(dimethylaminopropyl)amide are protonated to a large degree at environmentally relevant pH. Whereas C20/22 ATQ is a quaternary ammonium chloride. This difference is not considered to be of ecotoxicological relevance.
C16-18 DMAPA amidoamine as well as Stearic acid 3-(dimethylaminopropyl)amide on the one side contain DMAPA as amine-backbone; C20/22 ATQ on the other side is based on dimethylamine as amine-backbone. However, as it is shown in the aquatic toxicity tests with Stearic acid 3-(dimethylaminopropyl)amide and C20/22 ATQ, this has no big influence on ecotoxicity.
3. Physicochemical properties:
Table 2: Physicochemical properties
|
Source substances |
Target substance |
|
Endpoints |
Stearic acid 3-(dimethylaminopropyl) amide |
C20/22 ATQ |
C16-18 DMAPA amidoamine |
Molecular weight [g/mol] |
368.64 |
ca. 400 |
340.59 - 368.64 |
Physical state at 20°C / 1013 hPa |
Solid (paste) |
Solid |
Solid (waxy) |
Melting point |
67.4°C |
Decomposition at 220-240°C |
41.8°C |
Boiling point |
412.3°C |
Decomposition |
320.5°C |
Surface tension |
37.86 mN/m at 0.22 g/L |
47.0 mN/m at 0.01 g/L |
26.7 mN/m at 0.027 g/L |
Water solubility |
10 mg/L at 20°C |
10 mg/L at 25°C |
3.65 mg/L at 23°C |
Log Kow |
2.01 at 20°C, pH7 |
3.29 at 20°C |
2.01 at 20°C, pH7; read-across from Stearic acid 3-(dimethylaminopropyl) amide |
Vapour pressure |
3.4E-08 Pa at 20°C |
7E-05 Pa at 20°C |
3.4E-08 Pa at 20°C; read-across from Stearic acid 3-(dimethylaminopropyl) amide |
Adsorption / desorption |
no data (read-across from C20/22-ATQ) |
log Koc = 3 – 5.7 (batch equilibrium method) |
log Koc = 7.8-8.0 at 25°C (HPLC method) |
As demonstrated in the table above, the source substances have a similar physicochemical profile compared to the target substance. The substances are cationic surfactants and are strongly sorbing to solids due to ionic interactions and van der Waals forces.
4. Comparison of data from ecotoxicological endpoints
5.1 Ecotoxicity data of the target and source substances
Cationic surfactants sorb strongly to negatively charged surfaces like glass or biota. In order to avoid sorption to the glass of the test vessel and on the test organism well characterised river was used as aquatic medium to allow reliable test results.
Table 4: Ecotoxicological profiles for the source substances Stearic acid 3-(dimethylaminopropyl)amide and C20/22 ATQ, and the target substance C16-18 DMAPA amidoamine
|
Source substances |
|
Target substance |
Endpoints |
Stearic acid 3-(dimethylaminopropyl)amide |
C20/22 ATQ |
C16-18 DMAPA amidoamine |
Short-term toxicity to fish |
96 h LC50 >0.1 - <1 mg/L(nominal) |
96 h LC50 = 3.5 mg/L (meas., geom.. mean) |
No data; read-across |
Long-term toxicity to fish |
9 d NOEC(behaviour) = 0.1 mg/L (nominal) |
9 d NOEC = 0.24 mg/L (meas., geom.. mean) |
No data; read-across |
Short-term toxicity to aquatic invertebrates |
48 h EC50 = 381 µg/L (nominal) |
48 h EC50 = 1.39 mg/L (nominal) |
No data; read-across |
Long-term toxicity to aquatic invertebrates |
21 d NOEC(mortality) = 200 µg/L (nominal); 21 d EC10 (mortality) =200 µg/L (nominal) |
21 d NOEC = 128 µg/L |
No data; read-across |
Toxicity to aquatic algae and cyanobacteria |
72 h EC50 = 140 µg/L (nominal); 72 h EC10 = 71 µg/L (nominal) |
72 h EC50 = 3.48 mg/L (meas., geom. mean); 72 h EC10 = 0.78 mg/L (meas., geom. mean) |
No data; read-across |
Toxicity to microorganisms |
3 h EC50 >100 - < 1000 mg/L; 3 h NOEC = 100 mg/L |
3 h EC50 >100 - < 1000 mg/L; 3 h NOEC = 100 mg/L |
No data; read-across |
Biodegradation in water; screening |
readily biodegradable |
readily biodegradable |
readily biodegradable |
Toxicity to soil macroorganisms except arthropods (earthworm) |
No data |
54 d NOEC(reproduction, mortality,body weight) = 250mg/kg soil dw
14 d NOEC(mortality, biomass, development) = 1000 mg/kg soil dw |
No data; read-across |
Toxicity to terrestrial arthropods (Collembola) |
No data |
28 d NOEC(mortality, reproduction) = 500 mg/kg soil dw;
28 d LD50 > 1000 mg/kg soil dw |
No data; read-across |
Toxicity to soil microorganisms |
No data |
28 d EC50 = 76 mg/kg soil dw; 28 d EC10 = 15 mg/kg soil dw; 28 d NOEC = 10 mg/kg soil dw |
No data; read-across |
No experimental ecotoxicity data are available for the target substance C16-18 DMAPA amidoamine. However, as demonstrated above,Stearic acid 3-(dimethylaminopropyl)amide is the main constituent of the target substance. Thus, aquatic toxicity data of the source substance Stearic acid 3-(dimethylaminopropyl)amide are considered to be relevant also for the target substance C16-18 DMAPA amidoamine.
Terrestrial ecotoxicity data are available for the source substance C20/22 ATQ. Based on the close similarity of Stearic acid 3-(dimethylaminopropyl)amide and the target substance C16-18 DMAPA amidoamine, also the read-across from C20/22 ATQ is justified:
The substances are readily and ultimately biodegradable. 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 oxidised to the fatty acid which is subsequently degraded by beta oxidation (Kees van Ginkel, Handbook of Surfactants, Volume F, 1995).
In the following table the river water test results for Stearic acid 3-(dimethylaminopropyl) amide and C20/22 ATQ are given.
|
|
Stearic acid 3-(dimethylaminopropyl) amide |
C20/22 ATQ |
Ratio highest:lowest value |
Chronic fish OECD 212 River water test |
NOEC repro (9d) |
0.1 mg/L |
0.24 mg/L |
2.4 |
Chronic daphnia OECD 211River water test |
NOEC repro (21d) |
0.2 mg/L |
0.13 mg/L |
1.5 |
Algae OECD 201River water |
ErC10 (72h) |
0.07 mg/L |
0.93 mg/L |
13.2 |
Algae OECD 201Reconstituted water |
ErC10 (72h) |
0.2 mg/L |
0.93 mg/L(RW) |
4.7 |
The ecotoxicity ratios for Chronic fish and Chronic daphnia is 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 Stearic acid 3-(dimethylaminopropyl) amide and C20/22 ATQ is 12.9 and much higher than expected. But from the tertiary alkyl dimethylamines (see above) it is known that the algae ecotoxicity in river water is sometimes higher than in reconstituted water. When comparing the Stearic acid 3-(dimethylaminopropyl) amide algae ErC10 (72h) in reconstituted water with the algae value for C20/22 ATQ river water the ratio for the endpoint drops from 12.9 to 4.5. The value 4.5 is well within the range for variability / uncertainty acceptable for algae test (3 standard deviations). The PNEC freshwater and marine for Stearic acid 3-(dimethylaminopropyl) amide is derived from the ErC10 (72h) river water algae test of 0.07 mg/L whereas the PNEC freshwater and marine for C20/22 ATQ is derived from the NOEC repro (21d) daphnia of 0.13 mg/L. The ratio between these two NOEC is 0.13/0.07=1.9 and well acceptable with respect to uncertainty / variability of test results.
Based on these data as well as on similar physicochemical properties and on the similar toxicological profile the read-across approach for long-term toxicity as well as terrestrial toxicity is considered to be appropriate. The available data are comparable for source and target substance, supporting the validity of the grouping approach.
5.3 Quality of the experimental data of the analogues:
Aquatic toxicity:
The source substance Stearic acid 3-(dimethylaminopropyl)amide has been tested in reliable (RL1) GLP-compliant studies according to OECD TG 201 and 202, and a reliable (RL2) study according to OECD TG 203 for short-term toxicity as well as reliable (RL1) GLP-compliant studies according to OECD TG 211 and 212 for long-term toxicity.
The source substance C20/22 ATQ has been tested in reliable (RL1) GLP-compliant studies according to OECD TG 201, 202 and 203 for short-term toxicity as well as reliable (RL1) GLP-compliant studies according to OECD TG 211 and 212 for long-term toxicity.
Terrestrial toxicity:
The source substance C20/22 ATQ has been tested in reliable (RL1) GLP-compliant studies according to OECD TG 207, 216, 222 and ISO 11267.
The available data from the source chemical are sufficiently reliable to justify the read-across approach.
5.4 Classification and labelling
Concerning environmental effects, the source substance Stearic acid 3-(dimethylaminopropyl)amide is classified as Aquatic Acute 1 (M-factor = 1) and Aquatic Chronic 2. The source substance C20/22 ATQ is classified as Aquatic Acute 1 (M-factor = 1).
Based on read-across, the target substance C16-18 DMAPA amidoamine is classified as Aquatic Acute 1 (M-factor = 1) and Aquatic Chronic 2.
The substances are neither PBT nor vP/vB substances.
6. Conclusion
The structural and physicochemical similarities between the source and the target substances and the similarities in their breakdown products presented above support the read-across hypothesis. Adequate and reliable scientific information indicates that the source and target substances and their subsequent degradation products have similar toxicity profiles.
As demonstrated, Stearic acid 3-(dimethylaminopropyl)amide is the main constituent of the target substance C16-18 DMAPA amidoamine.
Based on close the relationship the results from aquatic, sediment and terrestrial toxicity data obtained with the source substances Stearic acid 3-(dimethylaminopropyl) amide and C20/22 ATQ are also relevant for the target substance C16-18 DMAPA amidoamine.
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