N,N'-ethylenebis[N-acetylacetamide]

Hydrolysis

Administrative data

Endpoint:

hydrolysis

Type of information:

experimental study

Adequacy of study:

key study

Study period:

May 2002

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: see 'Remark'

Remarks:

The test was not performed according to OECD Guideline and GLP. However, the test design reflects the basic principles of OECD Guideline 111 and is the most appropriate for this substance as it mimics its use conditions. Also, a laboratory quality control system was in place.

Cross-reference

Reason / purpose for cross-reference:

reference to same study

Data source

Reference

Reference Type:

study report

Title:

Unnamed

Year:

2002

Report date:

2002

Materials and methods

Test guideline

Qualifier:

no guideline followed

Principles of method if other than guideline:

Perhydrolysis: 1.5 g of a persalt, 1.0 g disodium carbonate and 0.3 g sodium disilicate (3NaG) were stirred in 1 litre tap water at room temperature (approx. 20°C). To that suspension 0.54 g Peractive AC white (92 % TAED) were added. At each time interval 20 ml of the suspension were withdrawn and acidified with c = 0.5 mol/l sulphuric acid to stop the reaction. After addition of 10 ml acetonitrile/methanol (1/1) to improve the solubility of TAED and of the perhydrolysis products the volume was made up to 100 ml with tap water. The solution was filtered through a 0.2 µm membrane filter and injected into the HPLC instrument.

Hydrolysis: Same procedure as perhydrolysis but without persalt

GLP compliance:

no

Test material

Test material information

Constituent 1

Reference substance name:

N,N'-ethylenebis[N-acetylacetamide]

EC Number:

234-123-8

EC Name:

N,N'-ethylenebis[N-acetylacetamide]

Cas Number:

10543-57-4

Molecular formula:

C10H16N2O4

IUPAC Name:

N,N'-ethylenebis[N-acetylacetamide]

Details on test material:

- Name of test material (as cited in study report): Peractive AC white
- Physical state: granule
- Composition of test material, percentage of components: TAED granule with 92% active content and carboxy methyl cellulose as granulating
auxiliary
- Lot/batch No.: DEADG5M003

Specific details on test material used for the study:

Details on properties of test surrogate or analogue material (migrated information):
not applicable

Radiolabelling:

no

Study design

Analytical monitoring:

yes

Details on sampling:

- Sampling intervals for the parent/transformation products:

Perhydrolysis: sampling after 5, 10, 20, 30, 60 and 120 minutes
Hydrolysis: sampling after 5, 10, 20, 30, 60, 120 minutes, 3 h, 4 h, 5 h, 6 h,
7 h, 8 h, 9 h and 24 h

- Sampling method:

Perhydrolysis and Hydrolysis: At the soecified time intervals 20 ml of the
suspension were withdrawn and acidified with c = 0.5 mol/l sulphuric
acid to stop the reaction. After addition of 10 ml acetonitrile/methanol (1/1)
to improve the solubility of TAED and of the perhydrolysis products the
volume was made up to 100 ml with tap water. The solution was filtered
through a 0.2 µm membrane filter and injected into the HPLC instrument.

- Sampling intervals/times for pH measurements:

Perhydrolysis: sampling after 5, 10, 20, 30, 60 and 120 minutes
Hydrolysis: sampling after 5, 10, 20, 30, 60, 120 minutes, 3 h, 4 h, 5 h, 6 h,
7 h, 8 h, 9 h and 24 h

- Other observation, if any (e.g.: precipitation, color change etc.):

Appearance of the solution before addition of Peractive AC white: Turbid,
contains undissolved particles

Buffers:

no buffer was used, only tap water

Estimation method (if used):

Estimation of disappearance time (DT50) was determined by reading from the log c versus time curve of the reaction.

Details on test conditions:

TEST SYSTEM
- Type, material and volume of test flasks, other equipment used: measuring glas flasks

TEST MEDIUM
- Kind and purity of water: tap water
- Preparation of test medium:
1.5 g sodium perborate monohydrate (perhydrolysis test only), 1.0 g disodium carbonate
and 0.3 sodium disilicate (3NaG) were stirred in 1 litre tap water at room
temperature (approx. 20°C). To that suspension were 0.54 g Peractive AC white
(92 % TAED) added.

Duration of test

Duration:

24 h

Initial conc. measured:

ca. 499 mg/L

Number of replicates:

One replicate per time point for Perhydrolysis
One replicate per time point for Hydrolysis

Positive controls:

no

Negative controls:

no

Statistical methods:

For Perhydrolysis: degradation kinetics with calculation of rate constant and half-life according to OECD 111
For Hydrolysis: Determination of DT50 by graphical analysis

Results and discussion

Preliminary study:

no preliminary study was performed

Transformation products:

yes

Identity of transformation products

Identity of transformation products 1

No.:

#1

Reference

Reference substance name:

Unnamed

IUPAC name:

tri acetyl ethylene diamine (TriAED)

Identifier:

common name

Identity:

tri acetyl ethylene diamine (TriAED)

Identity of transformation products 2

No.:

#2

Reference

Reference substance name:

Unnamed

IUPAC name:

di acetyl ethylene diamine (DAED)

Identifier:

common name

Identity:

di acetyl ethylene diamine (DAED)

Details on hydrolysis and appearance of transformation product(s):

Perhydrolysis: The perhydrolysis of TAED can be regarded as pseudo-first order reaction. The rate constant k(obs) was 0.0038 s-1 and the half-life t(0.5) 184 s (calculated according to OECD 111 (12 May 1981).

Hydrolysis: The hydrolysis of TAED is a complex reaction. Neither pseudo-first order nor second order fitting could be applied. The rate constant was
therefore not calculated. The disappearance time DT(50) was 19 min (determined by reading from the log c versus time curve of the reaction)

(for further details see "remarks on results including tables and figures")

Total recovery of test substance (in %)

% Recovery:

> 88 - <= 112

pH:

10

Temp.:

21 °C

Duration:

> 0.08 - <= 24 h

Dissipation DT50 of parent compound

Dissipation DT50 of parent compound 1

pH:

10

Temp.:

21 °C

DT50:

19 min

Type:

other: DT50 was determined by reading from the log c versus time curve of the reaction

Remarks on result:

other: Hydrolysis rate constant could not be calculated, as neither pseudo-first order nor second order fitting could be applied.

Dissipation DT50 of parent compound 2

pH:

9

Temp.:

21 °C

DT50:

3.2 h

Remarks on result:

other: DT50 calc. from pH 10 Hydrolysis results

Dissipation DT50 of parent compound 3

pH:

7

Temp.:

21 °C

DT50:

13 d

Remarks on result:

other: DT50 calc. from pH 10 Hydrolysis result

Dissipation DT50 of parent compound 4

pH:

10

Temp.:

23 °C

Hydrolysis rate constant:

ca. 0.23 min-1

DT50:

ca. 3 min

Type:

(pseudo-)first order (= half-life)

Remarks on result:

other: Values for Perhydrolysis i.e. in the presence of sodium perborate monohydrate

Details on results:

see "remarks on results including tables and figures

Any other information on results incl. tables

Perhydrolysis

	TAED content		TriAED content		DAED content		recovery rate
	mg/l	mmol/l	mg/l	mmol/l	mg/l	mmol/l	%
sample weight t =    5 min t =  10 min t =  20 min t =  30 min t =  60 min t = 120 min	499 161 37 6 <1 <1 <1	2.19  0.70 0.16 0.02 <0.01 <0.01 <0.01	-- 22 8 <1 <1 <1 <1	-- 0.12 0.04 <0.01 <0.01 <0.01 <0.01	-- 185 353 368 362 365 363	-- 1.29 2.45 2.56 2.51 2.54 2.52	-- 96 121 118 115 116 115

TriAED = triacetyl ethylene diamine

DAED = diacetyl ethylene diamine

Hydrolysis

	TAED content		TriAED content		DAED content		recovery rate
	mg/l	mmol/l	mg/l	mmol/l	mg/l	mmol/l	%
sample weight t =    5 min t =  10 min t =  20 min t =  30 min t =  60 min t = 120 min t =    3 h t =    4 h t =    5 h t =    6 h t =    7 h t =    8 h t =    9 h t =  24 h	499 373 343 271 211 107 37 16 8 4 3 <1 <1 <1 <1	2.19 2.59 2.38 1.88 1.47 0.74 0.25 0.11 0.06 0.03 0.02 <0.01 <0.01 <0.01 <0.01	-- 43 78 139 181 217 179 146 123 96 65 46 32 25 2	-- 0.23 0.42 0.75 0.97 1.17 0.96 0.78 0.66 0.51 0.35 0.25 0.17 0.13 0.01	-- 8 10 24 34 81 151 197 235 262 279 292 311 310 352	-- 0.05 0.07 0.16 0.24 0.56 1.05 1.36 1.63 1.82 1.94 2.03 2.16 2.15 2.44	-- 88 91 96 98 101 99 101 106 107 105 104 107 105 112

TriAED = triacetyl ethylene diamine

DAED = diacetyl ethylene diamine

pH and temperature

	Perhydrolysis		Hydrolysis
	pH	temp.	ph	temp.
t =    5 min t =  10 min t =  20 min t =  30 min t =  60 min t = 120 min t =    3 h t =    4 h t =    5 h t =    6 h t =    7 h t =    8 h t =    9 h t =  24 h	10.2 10.1 10.0 10.0 10.0 10.0 -- -- -- -- -- -- -- --	23.0 23.0 23.0 22.9 22.9 22.9 -- -- -- -- -- -- -- --	10.6 10.6 10.5 10.4 10.3 10.2 10.1 10.1 10.1 10.0 10.0 10.0 10.0 9.7	20.5 20.6 20.6 20.7 20.9 21.4 21.8 22.0 22.4 22.5 22.8 23.0 23.2 19.8

Applicant's summary and conclusion

Validity criteria fulfilled:

yes

Executive summary:

Hydrolysis of TAED was examined at pH 10 (0.54 g Peractive AC white (92 % TAED) in 1 L tap water containing 1.0 g disodium carbonate and 0.3 sodium disilicate) at room temperature (appr. 21°C). The results show that hydrolysis does neither follow 1^stnor 2^ndorder kinetic. Thus, the determined first half-life of 0.3 hours will decrease over time.

Perhydrolysis was studied under the conditions similar to the washing process (at pH 10 in the presence of perborate, disodium carbonate, sodium disilicate) at room temperature (appr. 23°C). TAED hydrolyzed rapidly with a half-live of 3 minutes (1^storder kinetic).

The initial hydrolysis product was triacetyl ethylenediamine which was further hydrolyzed to diacetyl ethylenediamine.