Reaction products of 2-(chloromethyl)oxirane and glycerol

Biodegradation in water and sediment: simulation tests

Administrative data

Endpoint:

biodegradation in water: sediment simulation testing

Remarks:

& surface water testing

Data waiving:

study scientifically not necessary / other information available

Justification for data waiving:

other:

Cross-reference

Cross-reference 1

Reason / purpose for cross-reference:

data waiving: supporting information

Reference

Endpoint:

biodegradation in water: ready biodegradability

Type of information:

experimental study

Adequacy of study:

key study

Study period:

2013-01-21 - 2013-03-18

Reliability:

1 (reliable without restriction)

Rationale for reliability incl. deficiencies:

other: well-documented GLP guideline study

Qualifier:

according to guideline

Guideline:

OECD Guideline 301 F (Ready Biodegradability: Manometric Respirometry Test)

Qualifier:

according to guideline

Guideline:

EU Method C.4-D (Determination of the "Ready" Biodegradability - Manometric Respirometry Test)

Qualifier:

according to guideline

Guideline:

other: US EPA Draft OPPTS 835.3110 (Paragraph q)

GLP compliance:

yes (incl. QA statement)

Remarks:

Federal Office of Public Health, Swiss GLP Monitoring Authorities, Bern

Specific details on test material used for the study:

Details on properties of test surrogate or analogue material (migrated information):
No surrogate or analogue material was used.

Oxygen conditions:

aerobic

Inoculum or test system:

sewage, predominantly domestic, adapted

Details on inoculum:

- Source of inoculum/activated sludge: aerobic activated sludge from a wastewater treatment plant (ARA Ergolz II, Füllinsdorf, Switzerland) treating predominantly domestic sewage water
- Preparation: The sludge was washed twice with tap water by centrifugation and the supernatant liquid phase was decanted. A homogenized aliquot of the final sludge suspension was weighed, thereafter dried and the ratio of wet to dry weight was calculated
- Pretreatment: Holding period was 1 day before use at which the sludge was aerated at room temperature. The slugde was thoroughly mixed and diluted with test water to a concentration of 1 g/L (dry weight basis). Defined amounts were added to obtain a final concentration of 30 mg dry material / L.

Duration of test (contact time):

55 d

Initial conc.:

30 mg/L

Based on:

test mat.

Parameter followed for biodegradation estimation:

other: Biological Oxygen Demand (BOD) measurement

Details on study design:

TEST SYSTEM
- Culturing apparatus: The test flasks (500 mL reaction vessels, labeled with the necessary information to ensure mistakable identification) were incubated under continuous stirring in a SAPROMAT D12 (Voith GmbH, Heidenheim, Germany). Oxygen consumption was recorded manually by taking a daily reading at least on each working day.
- Electro-chemical analysis process: The biodegradation process consumes the dissolved oxygen in the test medium and generates CO2. The CO2 is adsorbed by soda lime, which results in a decrease of the total pressure in the aritight test flasks. The pressure drop is detected and converted into an electrical signal by means of an electrode type manometer. The consumed oxygen is replaced by electrolytically generated oxygen from a copper sulfate solution.
- Test duration: 55 days. In accordance with the testing guidelines the test was prolonged since the biodegradation curve of the test substance showed that biodegradation had started but the plateau had not been reached.
- Light conditions: Darkness
- Test temperature: 22 °C, maintained with a built-in thermostat and checked at least each working day
- pH: prior to test start, the pH was measured in each test flask before the addition of the activated sludge inoculum. At the end of incubation, the pH was measured again in each test flask.

TEST WATER
Analytical grade salts were dissolved in purified water to obtain the following stock solutions:
1) 8.50 g/L KH2PO4, 21.75 g/L K2HPO4, 33.40 g/L Na2HPO4 x 2H2O, 0.50 g/L NH4Cl (pH of this solution: 7.4)
2) 22.50 g/L MgSO4 x 7H2O
3) 36.40 g/L CaCl2 x 2H2O
4) 0.25 g/L FeCl3 x 6 H2O, stabilised with one drop of concentrated HCl per L
Final test water preparation: 10 mL of stock solution No. 1 and 1 mL of each stock solution 2, 3 and were combined and made up to 1000 mL with purified water. The pH was adjusted from 8.1 to 7.4 with a diluted hydrochloric acid solution.

TOXICITY CONTROL
- Composition: Test substance and reference substance
- Percent biodegradation: calculated based on the COD of the test substance and the ThOD of the reference substance
- Results: 47 % after 14 days, 54 % after 28 days and 60 % after 55 days
- Conclusion: The test substance had no inhibitory effect on activated sludge microorganisms at the tested concentration of 101 mg/L since biodegradation was > 25 % within 14 days.

Reference substance:

other: Sodium benzoate (99.7 % purity)

Preliminary study:

No preliminary study was performed. In accordance with the testing guidelines, the experiment was prolonged (55 instead of 28 days), since the biodegradation curve showed that biodegradation had started but the plateau had not been reached.

Test performance:

Neither unusual observations during the experiment nor any other information is available affecting the obtained results.

Parameter:

% degradation (DOC removal)

Value:

24

Sampling time:

55 d

Parameter:

% degradation (DOC removal)

Value:

13

Sampling time:

28 d

Details on results:

1,2,3-Propanetriol, glycidyl ethers was found to be biodegradable under the applied test conditions within 55 days. However, the pass level for ready biodegradability, i.e. biodegradation of at least 60 % of the COD in a 10-day window within the 28-day period of the experiment, was not reached.

Parameter:

COD

Value:

1.54 mg O2/g test mat.

Results with reference substance:

81 % after 14 days, 87 % after 28 days and 91 % at the end of the test (Day 55)

Table 2. Oxygen consumption in the test flasks

	Cumulative oxygen consumption [mg/L]
	Test item		Inoculum control		Procedure control		Toxicity control
Time	Replicate No.		Replicate No.		Replicate No.		Replicate No.
[days]	1	2	1	2	1	2	1
0	0	0	0	0	0	0	0
1	0	0	0	0	7	0	9
2	3	1	2	4	80	74	82
3	8	2	6	6	105	96	109
4	8	3	7	6	124	114	127
5	--	--	--	--	--	--	--
6	10	7	10	9	136	128	141
7	12	8	12	11	142	134	146
8	13	11	14	13	146	138	150
9	13	11	14	13	148	138	151
10	14	11	14	13	149	142	154
11	--	--	--	--	--	--	--
12	--	--	--	--	--	--	--
13	17	14	16	15	154	146	166
14	19	17	18	17	156	150	170
15	22	19	18	17	157	152	172
16	24	21	18	18	158	152	175
17	26	24	18	18	160	154	176
18	--	--	--	--	--	--	--
19	--	--	--	--	--	--	--
20	32	32	21	19	164	156	183
21	34	33	21	21	165	158	185
22	36	35	22	21	166	158	187
23	36	36	22	21	167	160	188
24	38	37	22	21	167	160	189
25	--	--	--	--	--	--	--
26	--	--	--	--	--	--	--
27	42	41	23	21	170	163	194
28	44	42	23	21	170	163	195
29	44	44	24	22	171	163	196
30	46	45	25	23	172	173	197
31	46	47	25	23	173	173	199
32	--	--	--	--	--	--	--
33	--	--	--	--	--	--	--
34	48	48	25	23	174	173	202
35	50	49	25	23	175	173	203
36	50	50	25	23	176	173	205
37	51	51	25	23	176	173	206
38	53	52	27	24	177	173	207
39	--	--	--	--	--	--	--
40	--	--	--	--	--	--	--
41	57	56	27	24	179	173	212
42	57	57	27	25	180	173	213
43	57	58	28	25	181	173	214
44	59	59	29	26	182	175	215
45	59	60	29	27	183	175	216
46	59	60	29	27	183	175	216
47	59	61	29	27	183	175	217
48	61	62	29	27	183	175	218
49	63	64	30	27	184	178	219
50	63	64	30	28	184	178	220
51	63	65	30	28	184	178	220
52	63	67	30	28	185	178	221
53	65	67	31	28	185	178	222
54	--	--	--	--	--	--	--
55	66	70	31	29	186	178	224

Validity criteria fulfilled:

yes

Remarks:

Validity criteria of the applied guideline are met.

Interpretation of results:

under test conditions no biodegradation observed

Conclusions:

The well-documented report describes a valid guideline study which was conducted under certificated GLP compliance. At Exposure Day 28 and at test end after 55 days, the mean biodegradation of 1,2,3-Propanetriol, glycidyl ethers amounted to 13 % and 24 % of the COD, respectively.

Executive summary:

The test substance 1,2,3-Propanetriol, glycidyl ethers was investigated for its ready biodegradability in a manometric respirometry test over 55 days according to the OECD Guideline 301 F, EU Method C.4‑D and US EPA Draft OPPTS 835.3110 (Paragraph (q)) (Eisner, 2013). In accordance with the testing guidelines the test was prolonged to 55 days since the biodegradation curve of the test item showed that biodegradation had started but the plateau had not been reached by Day 28. The percent biodegradation of the test item was calculated based on the chemical oxygen demand of 1.54 mg O2/mg test item. The biochemical oxygen demand (BOD) of 1,2,3-Propanetriol, glycidyl ethers in the test media increased from test start until test termination after 55 days. At Exposure Day 28 and at test end after 55 days, the mean biodegradation of 1,2,3-Propanetriol, glycidyl ethers amounted to 13 % and 24 % of the COD, respectively. Consequently, the test substance was considered as not readily biodegradable under the test conditions. The pass level for ready biodegradability, i.e. biodegradation of at least 60 % of the COD in a 10‑day window within the 28‑day period of the test, was not reached. In the toxicity control containing both1,2,3-Propanetriol, glycidyl ethers and the reference item sodium benzoate, the run of the curve of the oxygen consumption over the 55‑day exposure period was similar but significantly higher than the one of the two procedure controls, containing only the reference item. Within 14 days of exposure, biodegradation amounted to 47 % and reaching 60 % at the end of the test at Day 55. Thus, according to the test guidelines, the test item had no inhibitory effect on activated sludge microorganisms at the tested concentration of 101 mg/L because biodegradation in the toxicity control was > 25 % within 14 days. In the procedure controls, the reference item was degraded by an average of 81 % by Exposure Day 14, thus confirming suitability of the activated sludge. At Day 28, the reference item was degraded by an average of 87 % and by 91 % at the end of test (Day 55).

Cross-reference 2

Reason / purpose for cross-reference:

data waiving: supporting information

Reference

Endpoint:

partition coefficient

Type of information:

(Q)SAR

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Scientifically accepted calculation method.

Justification for type of information:

QSAR prediction

Principles of method if other than guideline:

KOWWIN v1.67 uses the chemical structure of a compound to predict the logarithmic octanol-water partition coefficient (logPow), which is calculated by determining LogPow contributions from individual molecular fragments and then summing up these contributions.

GLP compliance:

no

Remarks:

Not applicable.

Type of method:

other: QSAR prediction

Partition coefficient type:

octanol-water

Type:

log Pow

Partition coefficient:

-1.78

Remarks on result:

other: Main component with clorine

Type:

log Pow

Partition coefficient:

-1.94

Remarks on result:

other: Main component without chlorine

Details on results:

The single fragments were detected as: aliphatic carbons (-CH2 (8 times) and –CH (4 times)) with coefficients of 0.49 and 0.36, respectively. A hydroxy aliphatic attach (-OH) with a coefficient of -1.41 and 5 oxygen as aliphatic attachments (-O-) with coefficients of -1.25, each. The main component containing chlorine possesses furthermore a single coefficient of 0.31 for the –CL fragment.

Conclusions:

The study report describes a scientifically accepted calculation method for determination of the partition coefficient using the US-EPA software KOWWIN v1.67. No GLP criteria are applicable for the usage of this tool and the QSAR estimation is easily repeatable.

Executive summary:

The partition coefficient of the test substance was determined by the computer program KOWWIN v1.67 (EPIWIN software) by US-EPA (Chemservice S.A., 2011; prediction was performed by the data owner). This program uses the chemical structure of a compound to predict the logarithmic octanol-water partition coefficient (logPow). Structures are used in their SMILES notation. LogPow is calculated by determining LogPow contributions from individual molecular fragments and then summing up these contributions. The single fragments were detected as: aliphatic carbons (-CH2 (8 times) and –CH (4 times)) with coefficients of 0.49 and 0.36, respectively. A hydroxy aliphatic attach (-OH) with a coefficient of -1.41 and 5 oxygen as aliphatic attachments (-O-) with coefficients of -1.25, each. The main component containing chlorine possesses furthermore a single coefficient of 0.31 for the –CL fragment. As overall result, the partition coefficient of the substance was calculated to be -1.78 with and -1.94 without chlorine.

Cross-reference 3

Reason / purpose for cross-reference:

data waiving: supporting information

Reference

Endpoint:

adsorption / desorption

Remarks:

adsorption

Type of information:

(Q)SAR

Adequacy of study:

key study

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: Scientifically accepted calculation method

Justification for type of information:

QSAR prediction

Principles of method if other than guideline:

KOCWIN program (v4.10): scientifically accepted calculation method for soil adsorption estimation of organic chemicals. Two different models are used for this estimation: the Sabljic Molecular Connectivity Index (MCI) method as well as the so-called traditional method, which is based on the LogPow.

GLP compliance:

no

Remarks:

not applicable

Type of method:

other: QSAR estimation

Media:

soil

Analytical monitoring:

not required

Computational methods:

Using the computer tool KOCWIN v2.00 by US-EPA (EPIWIN) the organic-normalized sorption coefficient for soil (soil adsorption, Koc) can be estimated. The following two different models are used: Salbjic molecular connectivity method (MCI) and the traditional method, which is based on the logPow value of the substance. In general, the MCI method is taken more seriously into account, due to the fact that it includes improved correction factors.

Phase system:

other: Koc

Type:

other: Koc

Value:

0.203 L/kg

Remarks on result:

other: LogPow-based estimate (traditional method)

Phase system:

other: Koc

Type:

other: Koc

Value:

10 L/kg

Remarks on result:

other: MCI method, includes improved correction factors - most relevant

Validity criteria fulfilled:

yes

Remarks:

scientifically accepted calculation method

Conclusions:

The Koc of the substance 1,2,3-propanetriol, glycidyl ethers was calculated to be 10 L/kg using the MCI method of KOCWIN program (v4.10), whereby the traditional method reveals a value of 0.2034 L/kg. In general, the MCI method is taken more seriously into account, due to the fact that it includes improved correction factors.

Executive summary:

The prediction for soil adsorption property of the substance 1,2,3-propanetriol, glycidyl ethers was determined by the computer program KOCWIN v2.00 (EPIWIN software) by US-EPA (Chemservice GmbH, 2011). The program estimates the organic-normalized sorption coefficient for soil, which is designated as Koc. The following two models are used: the Salbjic molecular connectivity (MCI) method as well as the traditional method which is based on the logPow value of the substance. The MCI method is taken more seriously into account, due to the fact that is includes improved correction factors, resulting in a Koc value of 10 L/kg. The traditional method gives a value of 0.2034 L/kg.