Reaction products of tetrabromophthalic anhydride with 2,2'-oxydiethanol and methyloxirane

Additional information on environmental fate and behaviour

Administrative data

Endpoint:

additional information on environmental fate and behaviour

Type of information:

calculation (if not (Q)SAR)

Remarks:

Migrated phrase: estimated by calculation

Adequacy of study:

key study

Study period:

November 2009

Reliability:

2 (reliable with restrictions)

Rationale for reliability incl. deficiencies:

other: The registered material is a UVCB substance. Protperties were estimated for the reference substances, 2056-635-2. Estimtion method (EPI Suite) recommended by IUCLID Guidance Documents.

Data source

Reference

Reference Type:

other: software program

Title:

Estimation Programs Interface (EPI) Suite™ v3.20 for Microsoft® Windows,

Author:

Anonymous

Bibliographic source:

U.S. Environmental Protection Agency, Washington, DC, U.S.A.http://www.epa.gov/opptintr/exposure/pubs/episuite.htm.

Materials and methods

Test guideline

Qualifier:

no guideline followed

Principles of method if other than guideline:

Properties of the Reference Substance were modeled using EPI Suite v3.20.

GLP compliance:

no

Type of study / information:

Environmental Fate and Distribution Properties of the Reference Substance were modeled using EPI Suite v3.20.

Test material

Test material information

Constituent 1

Reference substance name:

2-(2-hydroxyethoxy)ethyl 2-hydroxypropyl 3,4,5,6-tetrabromophthalate

EC Number:

243-885-0

EC Name:

2-(2-hydroxyethoxy)ethyl 2-hydroxypropyl 3,4,5,6-tetrabromophthalate

Cas Number:

20566-35-2

Molecular formula:

C15H15Br4O7 (one ring component) C8 H2 Br4 O4 . C4 H10 O3 . C3 H8 O2 Unspecified reaction product of the three components

IUPAC Name:

2-(2-hydroxyethoxy)ethyl 2-hydroxypropyl 3,4,5,6-tetrabromophthalate

Details on test material:

Modeling was based on the Reference Substance (CASRN 20566-35-2).

Results and discussion

Any other information on results incl. tables

Reference Substance Modeling Results

The modeling (Table 1) indicates that soil is the most important compartment with respect to the environmental distribution of the Reference Substance. Fast aerobic biodegradation in soil is not expected based on the STP modeling, however, anaerobic biodegradation may be possible. If applicable to soil, these results suggest the Reference Substance would not biodegrade in the upper aerobic soil levels, but may biodegrade in lower anaerobic levels or in other soil regions where anaerobic conditions exist. Further, hydrolysis is expected with half-lives of 1.363 and 13.69 days at pH 8 and 7, respectively. Thus, the moisture content in or on soils may allow abiotic degradation, which would proceed at faster rates than biological degradation. The low adsorption coefficient (10) indicates binding to soil will be low and thus should not affect biotic or abiotic degradation. 

The modeling indicates that water is the second most important environmental compartment with respect to distribution of the Reference Substance. However, hydrolysis should substantially impact any water concentrations. Predicted hydrolysis products of the Reference Substance are tetrabromophthalic acid and alcohols. 

TABLE 1. Environmental Fate Parameters for the Reference Substance using EPI Suite,

Parameter	Estimation Program	Result
5.1 Stability
Photodegradation in Air	AOP v1.92	Overall OH rate constant: 30.5163 E-12 cm3/molecule-sec Half-life: 0.351 days (12-hr day; 1.5E6 OH/cm3) Hlaf-life: 4.206 hours
Hydrolysis	HYDROWIN v1.67	Model used substitutes (**) for estimation.  Ester: R1-C(=O)-O-R2. **R1: -Phenyl [3 fragments] meta:-Br, para:-Br, meta:-Br. **R2: -CH2-CH#. Ortho-postion fragments on phenyl ring not considered. Kb hydrolysis at atom#10: 4.315E+000 L/mol-sec Ester: R1-C(=O)-O-R2.  **R1:-Phenyl [2 fragments] para:-Br, meta:-Br. **R2:-CH2-CH2-O-CH3. Ortho-postion fragments on phenyl ring not considered. Kb hydrolysis at atom#18: 1.57E+000 L/mol-sec Total Kb for pH>8 at 25 deg C: 5.886+000 L/mol-sec Kb Half-life at pH8: 1.363 days Kb half-life at pH 7: 13.629 days
Photodegradation in Water	No Estimate	----
Photodegradation in Soil	No Estimate	----
5.2 Biodegradation
Water	LEVEL III Fugacity Model using Biowin Ulitmate, AOPwin	Half-life: 1440 hours
Water and Sediment	LEVEL III Fugacity Model using Biowin Ulitmate, AOPwin	Half-life in sediment: 1.296E+004 hours
Soil	LEVEL III Fugacity Model using Biowin Ulitmate, AOPwin	Half-life: 2880 hours This estimate is in accordance with measured values obtained for a structural analog, 1,2-Benzenedicarboxylic acid, 3,4,5,6-tetrabromo-, bis(2-ethylhexyl) ester (CASRN 26040-51-7).
Mode of Degradation in Actual Use	STP Fugacity Model BIOWIN (v4.10)	Primary sludge: 12.96%, Waste Sludge 9.73%, Total Biodegradation 0.26%, Total Removal 22.95%, Final Water Effluent 77.05% Linear Model: Does Not Biodegrade Fast Non-Linear Model: Does Not Biodegrade Fast Ultimate Biodegradation Timeframe: Months Primary Biodegradation Timeframe: Weeks MITI Liner Model: Biodegrades Fast MITI Non-Linear Model: Does Not Biodegrade Fast Anaerobic Model: Biodegrades Fast Ready Biodegradation Prediction: NO
5.3 Bioaccumulation
Aquatic/Sediment Organisms	BCF v2.17	Estimated Log BCF=1.596 BCF=39.42
Terrestrial Organisms	No Estimate	----
5.4 Transport and Distribution
Adsorption/ Desorption	PCKOCWIN v1.66	10
Henry’s Law Constant, 25°C	HENRY v3.10	2.23E-021 atm-m3/mole 9.12E-20 unitless
Distribution Modeling	LEVEL III Fugacity Model	Emissions of 1000 kg/hr to air, water and soil Air: 0.000458%, half-life 8.41 hr Water: 8.72%, half-life 1.44E3 hr (NOTE: this half-life does not take into account the predicted hydrolysis; See HYDROLYSIS) Soil: 89.6%, half-life 2.88E003 hr Sediment: 1.72%, half-life 1.3E004
Other Distribution Data	KOAWIN v1.10 AEROWINv1.00 Volatilization from Water	Log Koa (octanol/air): 17.781 Koa (octanol/air): 6.035E+017 Sorption to aerosols at25°C: Kp (particle/gas partition coef.) 5.91E+003 m3/ug (Mackay model); 1.48E+005 m3/ug (Octanol/air model); Fraction sorbed to airborne particulates (phi): 1 (Junge-Pankow, Mackay, and Octanol/air models) Half life: 6.1x10+8 years (River); 6.6x10+9 years (Lake)

Table 2. Environmental Fate Parameters for Tetrabromophthalic Acid using EPI Suite, v3.20.

Parameter	Estimation Program	Result
5.1 Stability
Photodegradation in Air	AOP v1.92	Overall OH rate constant: 1.0464 E-012 cm3/molecule-sec Half-life: 10.222 days (12-hr day; 1.5E6 OH/cm3)
Hydrolysis	HYDROWIN v1.67	Program cannot estimate for this structure.
Photodegradation in Water	No Estimate	----
Photodegradation in Soil	No Estimate	----
5.2 Biodegradation
Water	LEVEL III Fugacity Model using Biowin Ulitmate, AOPwin	Half-life: 1440 hours
Water and Sediment	LEVEL III Fugacity Model using Biowin Ulitmate, AOPwin	Half-life in sediment: 1.296E+004 hours
Soil	LEVEL III Fugacity Model using Biowin Ulitmate, AOPwin	Half-life: 2880 hours
Mode of Degradation in Actual Use	STP Fugacity Model BIOWIN (v4.10)	Primary sludge: 37.88%, Waste Sludge 24.21%, Total Biodegradation 0.57%, Total Removal 62.65%, Final Water Effluent 37.35% Linear Model: Does Not Biodegrade Fast Non-Linear Model: Does Not Biodegrade Fast Ultimate Biodegradation Timeframe: Months Primary Biodegradation Timeframe: Weeks-Months MITI Liner Model: Biodegrades Fast MITI Non-Linear Model: Does Not Biodegrade Fast Anaerobic Model: Biodegrades Fast Ready Biodegradation Prediction: NO
5.3 Bioaccumulation
Aquatic/Sediment Organisms	BCF v2.17	Estimated Log BCF=0.500 BCF=3.162
Terrestrial Organisms	No Estimate	----
5.4 Transport and Distribution
Adsorption/ Desorption	PCKOCWIN v1.66	557.3 Koc may vary with pH
Henry’s Law Constant, 25°C	HENRY v3.10	1.17E-014 atm-m3/mole 4.79E-013 unitless
Distribution Modeling	LEVEL III Fugacity Model	Emissions of 1000 kg/hr to air, water and soil Air: 5.34E-007%, half-life 245 hr Water: 7.362%, half-life 1.44E+03 hr Soil: 82.8%, half-life 2.88E+03 hr Sediment: 9.381%, half-life 1.3E+04
Other Distribution Data	KOAWIN v1.10 AEROWINv1.00 Volatilization from Water	Log Koa (octanol/air): 16.278 Koa (octanol/air): 1.897E+016 Sorption to aerosols at25°C: Kp (particle/gas partition coef.) 0.183 m3/ug (Mackay model); 4.66E+003m3/ug (Octanol/air model); Fraction sorbed to airborne particulates (phi): 0.869 Junge-Pankow, 0.936 Mackay, and 1 Octanol/air models. Half life: 1.253x10+007 years (River); 1.367x10+008 years (Lake)

Applicant's summary and conclusion

Conclusions:

The modeling (Table 1) indicates that soil is the most important compartment with respect to the environmental distribution of the Reference Substance. Fast aerobic biodegradation in soil is not expected based on the STP modeling, however, anaerobic biodegradation may be possible. If applicable to soil, these results suggest the Reference Substance would not biodegrade in the upper aerobic soil levels, but may biodegrade in lower anaerobic levels or in other soil regions where anaerobic conditions exist. Further, hydrolysis is expected with half-lives of 1.363 and 13.69 days at pH 8 and 7, respectively. Thus, the moisture content in or on soils may allow abiotic degradation, which would proceed at faster rates than biological degradation. The low adsorption coefficient (10) indicates binding to soil will be low and thus should not affect biotic or abiotic degradation. 

The modeling indicates that water is the second most important environmental compartment with respect to distribution of the Reference Substance. However, hydrolysis should substantially impact any water concentrations. Predicted hydrolysis products of the Reference Substance are tetrabromophthalic acid and alcohols. 

Executive summary:

The modeling (Table 1) indicates that soil is the most important compartment with respect to the environmental distribution of the Reference Substance. Fast aerobic biodegradation in soil is not expected based on the STP modeling, however, anaerobic biodegradation may be possible. If applicable to soil, these results suggest the Reference Substance would not biodegrade in the upper aerobic soil levels, but may biodegrade in lower anaerobic levels or in other soil regions where anaerobic conditions exist. Further, hydrolysis is expected with half-lives of 1.363 and 13.69 days at pH 8 and 7, respectively. Thus, the moisture content in or on soils may allow abiotic degradation, which would proceed at faster rates than biological degradation. The low adsorption coefficient (10) indicates binding to soil will be low and thus should not affect biotic or abiotic degradation. 

The modeling indicates that water is the second most important environmental compartment with respect to distribution of the Reference Substance. However, hydrolysis should substantially impact any water concentrations. Predicted hydrolysis products of the Reference Substance are tetrabromophthalic acid and alcohols.