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EC number: 222-720-6 | CAS number: 3586-55-8
Concentrations (%) of the hydrolysis products of Mergal® V615 at 25°C obtained by13C‑NMR, quantified by external calibration
0.315% preparation of Mergal® V615 mixed in a 0.1 M aqueous borate buffer solution
Half-life was not calculated, but the hydrolysis DT50 and DT100 of Mergal® V615 are < 2 h. Complete release of formaldehyde and ethylene glycol had occurred at the initial analysis (1.98 h) and practically identical concentrations of the hydrolysis products were observed at all four subsequent measurements (4.02, 6.05, 8.08 and 24.05 h).
Under conditions representative of the uses of Mergal® V615 in PT06 and PT13 applications, the test substance was rapidly and completely hydrolysed. The hydrolysis products consisted of free formaldehyde and ethylene glycol only.
A non-guideline study of the hydrolysis of Mergal® V615 was conducted in an aqueous borate buffer system at a pH (8.5) and concentration (0.315%) both relevant to the use of the test substance as a preservative of in-can articles (PT06) and metal-working fluids (PT13). Hydrolysis products were identified and quantified by means of 13C NMR analysis, a non-destructive technique necessary to avoid the analysis itself influencing the hydrolysis.
Hydrolysis of MERGAL® V615 at 50°C
[μg / 10 mL]
Measured concentration [μg / 10 mL]
T = 0
T = 2.4 hours
T = 5 days
Dt values were not calculated. Plots of concentration versus time were not provided.
A GLP-compliant study of the hydrolysis of ‘MERGAL V615’ was conducted according to OECD No. 111 and EEC Directive 92/69, C.7, without deviation. Dilutions of test material in oxygen-free buffer solutions were incubated at pH 4, 7, and 9 at 50 °C for five days. Samples were taken for analysis at initiation (before incubation), 2.4 hours, and 120 hours, i.e., five days. Test substance content was determined by spectrophotometric analysis following derivatization.
The active substance in MERGAL® V615 is unstable to hydrolysis at pH 4, 7, and 9. At the initial analysis, almost all, i.e., 87 %, of the potential formaldehyde yield had already been released. After 2.4 hours the yield of free formaldehyde was more than 50%.
Concentration and hydrolysis values
At both pH values, the percentage of formaldehyde reached a plateau after 5-6 hours.
amounts of transformation products are determined in dependent of the concentration
# In the previous study 1 the apparent release of formaldehyde started later which was due to a less sensitive NMR probe head
Specification of the transformation products:
Amount of identified components contained in EGForm and in EGForm/D2O mixtures (study 2):
HO-CH2-O-CH2-O-CH2-CH2-OHb)asym. Dimethylol-ethylene glycol
HO-CH2-O-CH2-CH2-O-CH2-OHsymmetr. Dimethylol-ethylene glycol
HO-CH2-O-CH2-O- CH2-OHtrimer Formaldehyde-Hydrate2)
Sum of identified components
1) compounds in italics are provisional structure proposals 2) for summing up, formaldehyde contents calculated from the hydrates were used
The hydrolysis of EGForm was studied using 1H and 13C-NMR technique. The test substance was mixed with D2O to obtain a 1% solution at 20°C; pH values were adjusted to either 6.5 or 7.2 in study 1 and in a subsequent study (study 3) to pH 2, 4, 5.4, 7.1 and 8.9. The degree of hydrolysis was measured by detection of free formaldehyde via the 13C-NMR-spectra. In a further study, the individual constituents in EGForm were determined at different dilutions with D2O by applying the same technique.The individual constituents were identified via their characteristical chemical shifts, and quantified via the corresponding intensities.
In the first study, increasing amounts of formaldehyde were observedduring a reaction time of 14 hours, At both pH values, the amount of formaldehyde reached a plateau after 5-6 hours. Equilibrium between the reactants was observed: about 45-50% of formaldehyde content could be determined with respect to the initial weight of EGForm that is nearly the totally releasable formaldehyde (46.8%). Although, exact half-life times can not be calculated as the reaction is no pseudo first order, T1/2-values were estimated from the released formaldehyde in study 3. A clear effect of pH upon the estimated T1/2‑values was demonstrated. Thus T1/2-values were highest at pH 4 and most rapid hydrolysis was demonstrated at pH values >7. However, estimated values indicate a relatively fast hydrolysis (DT50< 1 hour) over the total pH range. The quantification of individual constituents of EGForm (study 2) showed increasing contents of the hydrolysis products ethylene glycol and formaldehyde in parallel to increasing the D2O content. Simultaneously, the content of methylolated ethylene glycols decreased.
Hydrolysis of the test substance was studied using 13C-NMR techniques and spectrophotometric analysis. The degree of hydrolysis was measured by detection of formaldehyde. During the reaction time, increasing amounts of formaldehyde were observed. At all pH values, the content of formaldehyde reached a plateau, an equilibrium between the reactants was observed.
The studies demonstrate the rapid hydrolysis. At large dilutions which are expected under environmental conditions (in wastewaters or surface waters) as well as in human body fluids, the test substance is expected to hydrolyse completely to formaldehyde and ethylene glycol.
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