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EC number: 214-317-9 | CAS number: 1120-71-4
- 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:
- experimental study
- Adequacy of study:
- supporting study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: see 'Remark'
- Remarks:
- A full test according to OECD 111 with fixed pH-values was performed. Unfortunately, it is not possible to fix the pH-values by buffering over the test time because as soon as the substance is mixed with the test water the pH decreases extremly. This pH-shift is likely due to hydrolysis of 1,3-propanesultone forming hydroxypropansulfonic acid, CAS 15909-83-8 due to hydrolytically induced ring cleavage. The preliminary results from the cancelled OECD 111 test are given below.Although unexpected problems occured and the study had to be cancelled the preliminary results are in line with theoretical assumptions on the hydrolysis of the substance. Hence, the results can be used to assess the hydrolytical stability of 1,3-propanesultone.
- Qualifier:
- according to guideline
- Guideline:
- OECD Guideline 111 (Hydrolysis as a Function of pH)
- GLP compliance:
- yes
- Radiolabelling:
- no
- Analytical monitoring:
- yes
- Buffers:
- - pH 4: (Bern Kraft; Citric acid, sodium chloride, sodium hydroxide)
-pH 7: (Bern Kraft;phosphate mixture)
-pH 9. (Pre-testBern Kraft; boric acid, potassium chloride, sodium hydroxide); tiethylamine hydrochloride, tris(hydrolxymethyl)aminomethande - Positive controls:
- no
- Negative controls:
- no
- Preliminary study:
- Pre-Test at 50°C:
The test item was completely hydrolysed at t1/2 <2 (estimated) at pH4, pH7 and pH 9 - Test performance:
- 0.52 - 0.63 g (pre-test: 1.03 - 1.37 g) of the test item exactly
weighed were dissolved in 50 ml (pre-test: 100 ml) of buffer
pH 4 or pH 9 (pre-test: buffer pH 4, pH 7 or pH 9). The buffer
solutions were fumigated with nitrogen prior to the application.
Considering the molar mass of the test item with 122.14 g/mol,
the concentrations of test item in the resulting solutions
correspond to - 0.1 mol/1.
Individual results
Test
pH 4 (3.7 -1.6)*
pH 7 (6.5 - 2.9)*
pH 9 (8.5 - 3.5)*
pH 4 (4.0 - 1.9)*
pH 4 (4.0- 1.9)*
pH 9 (8.8 - 1.3)*
pH value
pH4
pH 7
pH 9
T
[OC]
The buffer solutions of the pre-tests at 50°C were analyzed
immediately and after approx. 4h of storage. The absorbance
found analyzing the buffer solutions after storage was below
the limit of detection (corresponds to < 10 % of the start
concentration of the test item). The further tests were carried
out using a tempered CaFrcuvette and the I R signal at
1338 cm-1 was measured continuously by IR spectroscopy with
transmittance. - Details on hydrolysis and appearance of transformation product(s):
- - Formation and decline of each transformation product during test: CAS 15909-83-8, 3-hydroxy-1-propanesulfonic acid is supposed to be the product of hydrolysis due to hydrolytic ring cleavage of the parent compound. The product of hydrolysis is supposed to be hydrolytically stable as it does no contain labile functional groups.
- Pathways for transformation: hydrolytic ring cleavage of the parent compound - pH:
- 9
- Temp.:
- 21.3 °C
- DT50:
- 27.7 h
- Type:
- (pseudo-)first order (= half-life)
- Remarks on result:
- other: Decrease of pH from 8.8 to 1.3 at the end of the test. Hence, is is assumed that the DT50 would be lower if the pH value of 4 could have been fixed for the whole test period.
- Details on results:
- TEST CONDITIONS
- pH, sterility, temperature, and other experimental conditions maintained throughout the study: No
- Anomalies or problems encountered (if yes): Due to the hydrolytic ring cleavage of the parent compound 1,3-propanesultone and the subsequent formation of 3-hydroxy-1-propansulfonic acid the pH decreased rapidly in all test solutions. No buffer was found strong enough to maintain a constant pH-value over the test period (tested for pH4, pH7 and pH9). - Executive summary:
1,3 -propanesultone hydrolyses rapidly forming the strong acid 3 -hydroxy-1-propanesulfonic acid which leads to a strong pH-shift in the test solution.
- Endpoint:
- hydrolysis
- Type of information:
- other: Expert statement
- Adequacy of study:
- key study
- Reliability:
- 1 (reliable without restriction)
- Principles of method if other than guideline:
- Expert statement
- Transformation products:
- not measured
- Remarks on result:
- other: expert statement: rapid hydrolysis
Referenceopen allclose all
The pH shift in the test solutions might also indicate the speed of hydrolysis. At pH 7 the whole buffer was converted after approx. 20 hours while at pH 9 the buffer was converted after approx. 150 minutes. As both test solutions contained comparable amounts of buffer and test substance it can be concluded, that the substance was fully hydrolysed after these times.
pH value |
Tempeature [°C] |
T1/2 [h] |
pH 4 (4.0 – 1.9)* |
19.4 |
(about 29) |
pH 4 (4.0 – 1.9)* |
30.3 |
(about 5) |
pH 9 (8.80 – 1.3)* |
21.3 |
(about 28) |
*first value in brackets measured at test start, second values measured at test end
The decrease of the pH to lower pH values was investigated more precisely. Therefore two mixtures with approx.0.9 g of test item in 75 ml of buffer (pH 7 and pH 9) were made.
pH 7 |
pH 9 |
||
time [min] |
pH |
time [min] |
pH |
0 |
6.94 |
0 |
8.92 |
5 |
6.90 |
5 |
8.84 |
10 |
6.86 |
10 |
8.75 |
15 |
6.80 |
15 |
8.65 |
20 |
6.74 |
20 |
8.50 |
30 |
6.60 |
30 |
8.38 |
40 |
6.46 |
40 |
8.17 |
50 |
6.35 |
50 |
8.09 |
60 |
6.23 |
60 |
8.00 |
90 |
5.93 |
90 |
7.60 |
120 |
5.72 |
120 |
6.71 |
180 |
5.22 |
150 |
2.71 |
210 |
5.04 |
180 |
2.17 |
240 |
4.86 |
210 |
2.11 |
270 |
4.68 |
240 |
2.04 |
300 |
4.53 |
270 |
1.95 |
330 |
4.38 |
1020 |
1.40 |
360 |
4.24 |
|
|
390 |
.409 |
|
|
1230 |
2.20 |
|
|
1260 |
2.16 |
|
Due to the remarkable differences of the pH each measured between start and end of every test, further investigations as reported above and calculations therefrom were not sensible and therefore omitted. So the half-lives for 20°C and 25°C cannot be calculated.
A hydrolysis study is available. The study indicated that 1,3-propopanesultone is hydrolytically instable and decomposed to the 3-hydroxypropanesulfonic acid as hydrolysis product. In the Tier I study, the parent substance was not detectable after approx. 4 hours respectively at 50 °C under pH 4, 7 and 9. The Tier 2 study was conducted in the pH 4 buffer at two temperatures (20 °C and 30°C) and in the pH 9 buffer at one temperature (20°C).
3-hydroxypropanesulfonic acid is a strong acid, which acidity excessed the buffering capacity of neutral basic buffers used in the study. An additional pH declination test indicated that pH values of the buffers dropped down one hour later and up to 2 at approx. after 20 hours (pH 7) and 2.5 hours (pH 9). For this reason, the hydrolysis rate and hydrolytic half-lives set out below were estimated based on assuming of a first-order reaction and ignoring pH decline. The results were suggested for informative purpose only.
Test* |
Temp. (°C) |
kobs(h-1) |
kobsMean (h-1) |
t1/2(h) |
t1/2mean (h) |
pH 4 (4.0 – 1.9) |
19.4 |
0.0240519 |
- |
approx. 29 |
|
pH 4 (4.0 – 1.9) |
30.3 |
0.1316376 |
- |
approx. 5 |
|
pH 9 (8.8 – 1.3) |
21.3 |
0.0250349 |
- |
approx. 28 |
|
*the values in brackets referred to the measured pH values at the start and the end of the tests.
Mori (1971) studied the mechanism and reactivity of hydrolysis of aliphatic sulfonate esters and five- and six membered sultones, including 1,4-butanesultone, as well as a linear sultone. The kinetic constants of a previous study (Mori, 1971b) with 1,3-Propoanesultone and 1,4-butanesultone in water at pH 7 and ionic strength of 0.5 were reported as set out in the table below:
Test substance |
K1x 107(sec-1) |
Ea(Kcal/mol) |
ΔS≠ |
1,3-Propoanesultone |
215 |
20.4±.01* |
-13.8* (at 40°C) |
1,4-butanesultone |
5.67 |
20.0 |
- 20.0 |
*Bordwell (1959)
It is showed that the ration of relative reaction rates of the five-membered and 6-membered sultones in water at pH 7 is 37:1, implied the relative rate via BAL1-E1 mechanism, as the relationship between logK1and pH was consistent, and Ea values were the same.
Consequently, the study demonstrates that the hydrolysis of aliphatic sulfonate esters proceeded substantially by BAL1-E1 reaction via cleavage of C-O bond, the contribution aliphatic ring structure to the reactivity is very low, and the reactivity seemed to be controlled essentially by the entropy term (ΔS≠). The hydrolysis kinetic study indicated that the first-order reaction took place in water, but in a mixture system consisting of an aprotic solvent and water (65% of acetone-35% water), a sharp increase of hydrolytic rate was observed at pH > 7, this implied that an SN2_E2 reaction occurring in an extent way, although the BAL1-E1 reaction predominated.
In conclusion, 1,3-propoanesultone is considered to undergo rapid hydrolysis in water, forming the strong acid 3-hydroxypropanesulfonic acid. Predictably, the hydrolysis in water follows a first-order reaction and proceeds substantially by BAL1-E1 reaction via cleavage of C-O bond.
Reference:
Mori, A.; Nagayama, M.; Mandai, H. (1971a).Bul. Chem. Soc. Japan, 44(6):1669-1672
Mori, A.; Nagayama, M.; Mandai, H. (1971a).ibid., 74, 715
Bordwell, F.G.; Osborne, C.E.; Chapman R.D.; (1959) J. Amer. Chem. Soc., 81, 2698Description of key information
1,3-propanesultone hydrolyses rapidly under environmental conditions.
Key value for chemical safety assessment
Additional information
1,3-Propanesultone is considered to undergo rapidly hydrolysis in water, forming the strong acid 3-hydroxypropanesulfonic acid. Predictably, the hydrolysis in water follows a firs-order reaction and proceeds substantially by BAL1-E1 reaction via cleavage of C-O bond. The available guideline study according to OECD 111 indicated that 1,3-propanesultone hydrolyses rapidly forming the strong acid
, 3-hydroxypropanesulfonic acid which leads to a strong pH-shift in the test solution.
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