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Environmental fate & pathways

Hydrolysis

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Reference
Endpoint:
hydrolysis
Type of information:
calculation (if not (Q)SAR)
Adequacy of study:
key study
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
accepted calculation method
Justification for type of information:
Estimated data generated using the EPI Suite model developed by the USEPA.
Qualifier:
according to guideline
Guideline:
other: Modeling database
Principles of method if other than guideline:
HYDROWIN Program (v2.00) from EPI Suite estimation database
GLP compliance:
not specified
Specific details on test material used for the study:
- Name ( regulatory process): 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate

- Name of test material (as cited in study report): Acetamide, N- 3- bis 2-(acetyloxy)ethyl amino phenyl

- Molecular formula : C16H22N2O5

- Molecular weight : 322.359 g/mole

- Smiles notation : O=C(OCCN(c1cccc(NC(=O)C)c1)CCOC(=O)C)C
- InChl: 1S/C16H22N2O5/c1-12(19)17-15-5-4-6-16(11-15)18(7-9-22-13(2)20)8-10-23-14(3)21/h4-6,11H,7-10H2,1-3H3,(H,17,19)

- Substance type: Organic
-Physical state: white to off white coloured powder
Radiolabelling:
not specified
Analytical monitoring:
not specified
Estimation method (if used):
HYDROWIN v2.00
Transformation products:
not specified
Key result
pH:
7
Temp.:
25 °C
DT50:
3 950 yr
Type:
not specified
Remarks on result:
other: other details not available
Details on results:
The Hydrolysis half life of chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate at pH 7 is 3950 years at 25 oC temperature

HYDROWIN Program (v2.00) Results:

================================

SMILES : O=C(OCCN(c(cccc1NC(=O)C)c1)CCOC(=O)C)C

CHEM : Acetamide, N- 3- bis 2-(acetyloxy)ethyl amino phenyl -

MOL FOR: C16 H22 N2 O5

MOL WT : 322.36

--------------------------- HYDROWIN v2.00 Results ---------------------------

Hydrolyzable Function detected: Amides

-C-C(=O)-N-CWith

the exception of a few halogenated acetamides, most amides hydrolyze to acids extremely slowly at 25 degC and pH7 with half-lives measured in centuries. Electronegative groups on carbon or nitrogen greatly accelerate base catalyzed hydrolysis, but alkyl groups on nitrogen retard both acid and base catalyzed processes. No neutral hydrolysis is evident (Mabey and Mill, 1978). Selected amides half-lives include:

Half-Live (in years at 25C, pH7)

Acetamide 3950

Chloroacetamide 1.46

Dichloroacetamide 0.73

Trichloroacetamide 0.23

N-Methylacetamide 38000

Additional experimental amide data are available in the HYDRO on-line

User Guide (help file).

NOTE: Fragment(s) on this compound are NOT available from the fragment library. Substitute(s) have been used!!! Substitute R1, R2, R3,

or R4 fragments are marked with double astericks "**".

ESTER: R1-C(=O)-O-R2 R1: -CH3

** R2: -CH2-CH2-N(CH3)2

Kb hydrolysis at atom # 2: 1.601E-001 L/mol-sec

ESTER: R1-C(=O)-O-R2 R1: -CH3

** R2: -CH2-CH2-N(CH3)2

Kb hydrolysis at atom # 20: 1.601E-001 L/mol-sec

Total Kb for pH > 8 at 25 deg C : 3.203E-001 L/mol-sec

Kb Half-Life at pH 8: 25.047 days

Kb Half-Life at pH 7: 250.468 days

Validity criteria fulfilled:
not specified
Conclusions:
The hydrolysis half life at different pH and rate constant of test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate was estimated by EPI Suite ( HydroWin). The Half life estimated at pH 7 was 250.468 days and at pH 8 25.047 days at temperature 25 oC. The rate Constant at pH > 8 was 0.32 L/Mol/Sec at 25 oC.
Executive summary:

The hydrolysis half life at different pH and rate constant of test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1) was estimated by EPI  Suite (HydroWin). The Half life estimated at pH 7 was 250.468 days and at pH 8  25.047 days  at temperature 25 oC. The rate Constant at pH > 8 was 0.32 L/Mol/Sec  at 25 oC. Since, half life of hydrolysis of chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate is more than 10 days it shows negligible hydrolysis in water.

Description of key information

The hydrolysis half life at different pH and rate constant of test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1) was estimated by EPI  Suite (HydroWin). The Half life estimated at pH 7 was 250.468 days and at pH 8  25.047 days  at temperature 25 oC. The rate Constant at pH > 8 was 0.32 L/Mol/Sec  at 25 oC. Since, half life of hydrolysis of chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate is more than 10 days it shows negligible hydrolysis in water.

Key value for chemical safety assessment

Half-life for hydrolysis:
250.468 d
at the temperature of:
25 °C

Additional information

The hydrolysis half life at different pH and rate constant of test chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate ( CAS no. 27059 -08 -1) was estimated by EPI  Suite (HydroWin). The Half life estimated at pH 7 was 250.468 days and at pH 8  25.047 days  at temperature 25 oC. The rate Constant at pH > 8 was 0.32 L/Mol/Sec  at 25 oC. Since, half life of hydrolysis of chemical 2,2'-[(3-acetamidophenyl)imino]diethyl diacetate is more than 10 days it shows negligible hydrolysis in water.