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EC number: 239-362-1 | CAS number: 15332-99-7
- Life Cycle description
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- Endpoint summary
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- Additional toxicological data
Hydrolysis
Administrative data
Link to relevant study record(s)
Description of key information
Hydrolysis half-lives: ≤0.3 h at pH 4, ≤0.4 h at pH 5, ≤6.6 h at pH 7 and ≤0.1 h at pH 9 and 20-25°C (QSAR)
Key value for chemical safety assessment
Additional information
The hydrolysis half-lives of the submission substance have been predicted using a validated QSAR estimation method. Hydrolysis half-lives are estimated to be ≤0.3 h at pH 4, ≤0.4 h at pH 5, ≤6.6 h at pH 7 and ≤0.1 h at pH 9 and 20-25°C. These values are indicative of the upper limit for the hydrolysis half-lives of the submission substance because:
- The carbon-carbon double bond in the isopropyloxy side-chain could weaken the Si-O bond electronically
- In addition, the carbon atom of the isopropenyloxy side-chain is sterically less hindering compared to isopropyloxy group
- Both of these effects are expected to speed up the hydrolysis rates of the submission substance.
Therefore, the result is considered to be reliable, sufficient to justify that the hydrolysis half-lives of the substance is <12 hours and are used for assessment purposes.
As the hydrolysis reaction may be acid or base-catalysed, the rate of reaction is expected to be slowest at around pH 7 and increase as the pH is raised or lowered. For an acid-base catalysed reaction in buffered solution, the measured rate constant is a linear combination of terms describing contributions from the uncatalysed reaction as well as catalysis by hydronium, hydroxide, and general acids or bases.
kobs= k0+ kH3O+[H3O+] + kOH-[OH-] + ka[acid] + kb[base]
At extremes of pH and under standard hydrolysis test conditions, it is reasonable to suggest that the rate of hydrolysis is dominated by either the hydronium or hydroxide catalysed mechanism.
Therefore, at low pH:
kobs≈kH3O+[H3O+]
At pH 4 [H3O+] = 10 -4 mol dm-3 and at pH 2 [H3O+] = 10 -2 mol dm-3; therefore, kobs at pH 2 should be approximately 100 times greater than kobs at pH 4.
The half-life of a substance at pH 2 is calculated based on:
t1/2(pH 2) = t1/2(pH 4) / 100
The calculated half-life of the substance at pH 2 and 20-25°C is therefore ≤0.003 h (approximately ≤11 seconds).
Reaction rate increases with temperature therefore hydrolysis will be faster at physiologically relevant temperatures compared to standard laboratory conditions. Under ideal conditions, hydrolysis rate can be recalculated according to the equation:
DT50(XºC) = DT50(T°C) * e(0.08.(T-X))
Where T = temperature for which data are available and X = target temperature.
Thus, for tris(isopropenyloxy)(vinyl)silane the hydrolysis half-life at 37.5ºC and pH 7 (relevant for lungs and blood) is approximately ≤2.4 hours. At 37.5ºC and pH 2 (relevant for conditions in the stomach following oral exposure), the half-life is approximately ≤4 seconds. However, it is not appropriate or necessary to attempt to predict accurately when the half-life is less than 5-10 seconds. As a worst-case it can therefore be considered that the half-life of the substance at pH 2 and 37.5°C is approximately 5 seconds.
The hydrolysis products in this case are vinylsilanetriol and propen-2-ol/acetone.
The hydrolysis data for substances used in this dossier for read-across purposes for other endpoints are now discussed.
Hydrolysis of the read-across substance trimethoxyvinylsilane (CAS No: 2768-02-7)
Data for the substance trimethoxyvinylsilane (CAS No: 2768-02-7) are read-across to the submission substance tris(isopropenyloxy)(vinyl)silane for some endpoints. The hydrolysis half-lives and the hydrolysis products of the two substances are relevant for this read-across.
Trimethoxyvinylsilane has measured half-lives of <10 minutes, <2.4 h and <10 minutes at pH 4, pH 7 and pH 9 and 50°C in a preliminary study according to OECD 111. Also, it has predicted half-lives at 20-25ºC of 0.04 h (2 minutes) at pH 4, 0.1 h at pH 5 and 7, and 0.004 h (14 seconds) at pH 9. In a secondary source to which reliability could not be assigned, half-lives of 0.24 h at pH 7 and 0.58 h at pH 4 and 23°C were reported for trimethoxyvinylsialne.
The half-lives at pH 2 and 25°C, at pH 7 and 37.5°C and at pH 2 and 37.5°C may be calculated based on the predicted half-lives in the same way as for the registration substance above. This gives a half-life of 0.0004 h (approximately 1 second) at pH 2 and 25°C. However, it is likely that factors such as diffusion become rate-determining when the half-life is less than 5-10 seconds. As a worst-case it can therefore be considered that the half-life of trimethoxyvinylsilane at pH 2 and room temperature is approximately 5 seconds.
At pH 7 and 37.5°C (relevant for lungs and blood) and at 37.5ºC and pH 5.5 (relevant for dermal exposure), the half-life is approximately 0.04 hours (2 minutes),at 37.5ºC and pH 2 (relevant for conditions in the stomach following oral exposure), it is not appropriate to apply any further correction for temperature to the limit value and the hydrolysis half -life is therefore approximately 5 seconds
The hydrolysis products are vinylsilanetriol and methanol.
Hydrolysis of the read-across substance tris(2-methoxyethoxy)vinylsilane (CAS No: 1067-53-4)
Data for the substance tris(2-methoxyethoxy)vinylsilane (CAS No: 1067-53-4) are read-across to the submission substance tris(isopropenyloxy)(vinyl)silane for some endpoints. The hydrolysis half-lives and the hydrolysis products of the two substances are relevant for this read-across.
Tris(2-methoxyethoxy)(vinyl)silane has measured hydrolysis half-lives of 1.6 minutes at pH 4, 61.5 minutes at pH 7 and 0.94 minutes at pH 9 and 25°C were obtained for the substance in accordance with OECD 111 and in compliance with GLP. In order to determine the effect of temperature on hydrolysis rate of the submission substance, additional experiment was conducted at both pH 4 and pH 9 and 10°C and 35°C. At 10°C, hydrolysis half-life values of 3.3 minutes at pH 4 and 3.7 minutes at pH 9 were obtained. Similarly, at 35°C, hydrolysis half-lives of 0.96 minutes at pH 4 and 0.43 minutes at pH 9 were obtained
The hydrolysis products are vinylsilanetriol and 2-methoxyethanol.
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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