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EC number: 268-776-5 | CAS number: 68140-14-7
- 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
Hydrolysis
Administrative data
Link to relevant study record(s)
- Endpoint:
- hydrolysis
- Type of information:
- read-across from supporting substance (structural analogue or surrogate)
- Adequacy of study:
- key study
- Justification for type of information:
- It is considered appropriate to address the hydrolysis data requirement for DTO_DETA by read-across to an available study on AAI_TEPA.
AAI_TEPA is structurally related and of similar composition to AAI_DETA, a main component of DTO_DETA, with the only difference being the amine to which the fatty acid components are reacted with. AAI_TEPA contains a mixture of components, including monoamide, diamide and imidazoline (mono-, di and tri-condensate) structures. The substance therefore has common functional groups based on the amine, amide and imidazoline moieties, and is therefore considered structurally related to AAI_DETA.
For Rosins (the other main DTO_DETA component) no hydrolysis data is available. However, as Rosins are classified as readily biodegradable, information on hydrolysis is not required according to REACH Annex VIII. As such, it is judged that the hydrolysis data available for AAI_TEPA alone are sufficient to fulfil the DTO_DETA requirement for data on hydrolysis. - Reason / purpose for cross-reference:
- read-across source
- Preliminary study:
- pH 4
Measured Conc. Conc. Conc. corrected
Sample Nominal T conc. T=0 T measured Extracted total Hydrolysis Hydrolysis
(µg/L) (hrs) (µg/L) (hrs) (µg/L) (µg/L) (µg/L) (%) (%)
M339 8827 0 5043 120 1,1 14,0 15,1 100,0 99,8
M361 8827 0 5276 120 92,3 2184,2 2276,5 98,2 74,2
M434 8827 0 4984 120 3786,5 59,4 3846,0 24,0 56,4
M452 8827 0 4648 120 4388,3 991,3 5379,6 5,6 39,1
M460 8827 0 5007 120 4123,6 37,8 4161,4 17,6 52,9
pH 7
Measured Conc. Conc. Conc. corrected
Sample Nominal T conc. T=0 T measured extracted total Hydrolysis Hydrolysis
(µg/L) (hrs) (µg/L) (hrs) (µg/L) (µg/L) (µg/L) (%) (%)
M339 8827 0 3820 120 0,0 0,3 0,3 100,0 100,0
M361 8827 0 7613 120 7,9 68,1 76,0 99,9 99,1
M434 8827 0 6294 120 372,4 11,9 384,3 94,1 95,6
M452 8827 0 6161 120 7438,1 3365,7 10803,8 -20,7 -22,4
M460 8827 0 6375 120 684,6 7,6 692,2 89,3 92,2
pH 9
Measured corrected
Sample Nominal T conc. T=0 T Measured Extracted Total Hydrolysis Hydrolysis
(µg/L) (hrs) (µg/L) (hrs) (µg/L) (µg/L) (µg/L) (%) (%)
M339 8827 0 4179 120 0,0 0,1 0,1 100,0 100,0
M361 8827 0 4893 120 29,5 15,0 44,5 99,4 99,5
M434 8827 0 5103 120 11,1 3,2 14,3 99,8 99,8
M452 8827 0 4246 120 60,9 73,8 134,7 98,6 98,5
M460 8827 0 4754 120 94,4 16,3 110,6 98,0 98,7 - Test performance:
- Hydrolysis of test substance was determined for 5 different molar masses: 339, 361 434, 452 and 460, all being part of the composition of the test substance. Thereby the absorbance of the test substance to the wall of the test vessel was determined and used for correction of the results
- Transformation products:
- not specified
- No.:
- #1
- pH:
- 4
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.12 h-1
- DT50:
- 5.7 h
- St. dev.:
- 0.06
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 7
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 0.59 h-1
- DT50:
- 1.2 h
- St. dev.:
- 0.03
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 9
- Temp.:
- 50 °C
- Hydrolysis rate constant:
- 1.12 h-1
- DT50:
- 0.6 h
- St. dev.:
- 0.01
- Type:
- (pseudo-)first order (= half-life)
- Details on results:
- TEST CONDITIONS
- pH, sterility, temperature, and other experimental conditions maintained throughout the study: Yes
- Anomalies or problems encountered (if yes): no
MAJOR TRANSFORMATION PRODUCTS
At pH5:
- Range of maximum concentrations in % of the applied amount and day(s) of incubation when observed:
- Range of maximum concentrations in % of the applied amount at end of study period:
on the - the and -th day of incubation, respectively. At the end of the study period, the corresponding concentrations were - and -- % of the applied amount, respectively.
At pH7:
- Range of maximum concentrations in % of the applied amount and day(s) of incubation when observed:
- Range of maximum concentrations in % of the applied amount at end of study period:
on the - the and -th day of incubation, respectively. At the end of the study period, the corresponding concentrations were - and -- % of the applied amount, respectively.
At pH9:
- Range of maximum concentrations in % of the applied amount and day(s) of incubation when observed:
- Range of maximum concentrations in % of the applied amount at end of study period:
on the - the and -th day of incubation, respectively. At the end of the study period, the corresponding concentrations were - and -- % of the applied amount, respectively.
MINOR TRANSFORMATION PRODUCTS
Maximum concentrations in % of the applied amount
- at pH5:
- at pH7:
- at pH9:
MINERALISATION (distinguish between dark and irradiated samples)
- % of applied radioactivity present as CO2 at end of study:
PATHWAYS OF HYDROLYSIS
- Description of pathwayS:
- Figures of chemical structures attached: Yes
SUPPLEMENTARY EXPERIMENT (if any): RESULTS: - Validity criteria fulfilled:
- yes
- Conclusions:
- The M339 component, representing the most condensed and main fraction of the test substance, showed hydrolysis at all pH values and at all temperatures, hydrolysis rate increased at higher temperatures and at higher pH values. The hydrolysis rate observed at a pH value of 7 and 9 was more or less equal.
- Executive summary:
It is considered appropriate to address the hydrolysis data requirement for DTO_DETA by read-across to an available study on AAI_TEPA. AAI_TEPA is structurally related and of similar composition to AAI_DETA, a main component of DTO_DETA, with the only difference being the amine to which the fatty acid components are reacted with. AAI_TEPA contains a mixture of components, including monoamide, diamide and imidazoline (mono-, di and tri-condensate) structures. The substance therefore has common functional groups based on the amine, amide and imidazoline moieties, and is therefore considered structurally related to AAI_DETA. For Rosins (the other main DTO_DETA component) no hydrolysis data is available. However, as Rosins are classified as readily biodegradable, information on hydrolysis is not required according to REACH Annex VIII. As such, it is judged that the hydrolysis data available for AAI_TEPA alone are sufficient to fulfil the DTO_DETA requirement for data on hydrolysis.
The rate of hydrolysis of Tall oil, reaction products with tetraethylenepentamine (Redicote 404) was determined at 20°C, 30°C and 50°C and at the pH values of 4, 7 and 9 in agreement with OECD guideline 111.For the most condensed fraction of Redicote 404, TEPA tall oil diimidazolinewith molar mass M339, hydrolysis was observed at all tested pH values and temperatures. For TEPA tall oil diimidazolinethe half life(t½) at a temperature of 25°C could be calculated for all testedpH valuesusing the Arrhenius relationship.
At pH 4 the half-lives (t½) for the M339 component of Redicote 404 at a temperature of 20, 30 and 50°C were observed to be 371 hours, 47.5 hours and 5.7 hours respectively. Using the Arrhenius relationship a t½at 25°C was calculated of 136 hours.
At pH 7 the half-lives (t½) for the M339 component ofRedicote 404 at a temperature of 20, 30 and 50°C were observed to be 16.3 hours, 5.6 hours and 1.2 hours respectively. Using the Arrhenius relationship a t½at 25°C was calculated of 9.6 hours.
At pH 9 the half-lives (t½) for the M339 component ofRedicote 404at a temperature of 20, 30 and 50°C were observed to be 19.5 hours, 5.6 hours and 0.6 hours respectively. Using the Arrhenius relationship a t½at 25°C was calculated of 10.3 hours.
For two intermediate hydrolysis products of Redicote 404 the half-lives have been determined. Using specified time periods for the half life determination of TEPA tall oil monoimidazoline (M434) and TEPA tall oil monoamide (M452) the following results were calculated.
M434
M452
pH
Temp.
t½
Time period
t½
Time period
°C
(hr.)
(hr.)
4
20
156 days
162.5-720
79 days
262-720
30
39 days
6-144
44 days
6-144
50
54.0 hr.
2-24
66.6 hr.
2.24
7
20
158 hr.
1-48.5
28 days
1-48.5
30
Infinite
2-24
Infinite
2-24
50
13.5 hr.
0.5-4
29.1 hr.
0.5-4
9
20
141 hr.
7-75
7487 days
7-75
30
10.7 hr.
2-24
52.4 hr.
2-24
50
5.8 hr.
0.5-3
Infinite
0.5-3
Reference
50 degrees
Kobs | t1/2 | AVG t1/2 | St.dev. t1/2 | |||
slope | (hrs-1) | (hrs) | (hrs) | (hrs) | ||
pH 4 | series 1 | -0,0522 | 0,12 | 5,77 | 5,7 | 0,06 |
series 2 | -0,0529 | 0,12 | 5,69 | |||
pH 7 | series 1 | -0,2498 | 0,58 | 1,21 | 1,2 | 0,03 |
series 2 | -0,2604 | 0,60 | 1,16 | |||
pH 9 | series 1 | -0,4905 | 1,13 | 0,61 | 0,6 | 0,01 |
series 2 | -0,4811 | 1,11 | 0,63 | |||
30 degrees
Kobs | t1/2 | AVG t1/2 | St.dev. t1/2 | |||
slope | (hrs-1) | (hrs) | (hrs) | (hrs) | ||
pH 4 | series 1 | -0.0064 | 0.01 | 46.89 | 47.5 | 0.89 |
series 2 | -0.0063 | 0.01 | 48.14 | |||
pH 7 | series 1 | -0.0543 | 0.12 | 5.55 | 5.6 | 0.12 |
series 2 | -0.0526 | 0.12 | 5.72 | |||
pH 9 | series 1 | -0.0543 | 0.12 | 5.55 | 5.6 | 0.05 |
series 2 | -0.0536 | 0.12 | 5.62 | |||
20 degrees
Kobs | t1/2 | AVG t1/2 | St.dev. t1/2 | |||
slope | (hrs-1) | (hrs) | (hrs) | (hrs) | ||
pH 4 | series 1 | -0.0008 | 0.002 | 358.89 | 371 | 17.0 |
series 2 | -0.0008 | 0.002 | 382.87 | |||
pH 7 | series 1 | -0.0192 | 0.04 | 15.70 | 16.3 | 0.79 |
series 2 | -0.0179 | 0.04 | 16.82 | |||
pH 9 | series 1 | -0.0167 | 0.04 | 17.97 | 19.5 | 2.12 |
series 2 | -0.0144 | 0.03 | 20.97 | |||
Description of key information
Imidazoline DETA
The 1/2 life of 28 days at 20 degrees for tall oil diethyenetriamine imidazoline is read across from the hydrolysis data from a similar substance i.e. a TEPA based imidazoline. The read across of this realistic worst case 1/2 life is considered justified also taking the biodegradation data into account.
Rosins
Rosins are readily biodegradable, therefore hydrolysis data are not needed.
The half life for DETA imidazoline is used as the key value for tall oil reaction products eith diethylenetriamine as a worst case.
Key value for chemical safety assessment
- Half-life for hydrolysis:
- 28 d
- at the temperature of:
- 20 °C
Additional information
Imidazoline DETA
The imidazoline ring(s) of tall oil diethylenetriamine imidazoline most likely undergo(es) hydrolysis under alkaline, neutral and acidic conditions (Akzo Nobel 2010; Watts, 1990). A hydrolysis rate of an imidazoline has been measured using a Tetraethylene pentamine based imidazoline. For this imidazoline a number of hydrolysis rates were measured as the imidazolines are in general a mixture of imidazolines and amides (non ring closed imidazolines). The tetraethylene pentamine based imidazoline contains even di-imidazolines. The shortest half-lifes of 16.3 h at 20°C were found under neutral conditions for the hydrolysis of the first imidazoline ring of the di-imidazoline. For the next step in the hydrolysis degradation route i.e. the hydrolysis of the amide by which the alkyl chain is detached a half-life of 158 h at 20°C was derived. This second reaction step is considered to be representative of the hydrolysis of the DETA based imidazoline as this is also a monoimidazoline. The next step in hydrolysis degradation route would be the opening of the second imidazoline and here a half life of 28 days at 20°C is derived. The order in which these last two hydrolysis reactions take place is not completely clear. When considering the biodegradation half-life of the DETA based imidazoline and the shape of the degradation curve it seems that a hydrolysis step is here a rate determining step. For read-across from the source chemical (TEPA based imidazoline) to the target chemical (DETA based imidazoline) the use of worst-case half-life of 28 days at 20°C is considered to be justified also taking the biodegradation half-life into account.
Rosins
No hydrolysis data are available for the rosins. However, as Rosins are classified as readily biodegradable, information on hydrolysis is not required.
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