Registration Dossier
Registration Dossier
Data platform availability banner - registered substances factsheets
Please be aware that this old REACH registration data factsheet is no longer maintained; it remains frozen as of 19th May 2023.
The new ECHA CHEM database has been released by ECHA, and it now contains all REACH registration data. There are more details on the transition of ECHA's published data to ECHA CHEM here.
Diss Factsheets
Use of this information is subject to copyright laws and may require the permission of the owner of the information, as described in the ECHA Legal Notice.
EC number: 203-870-1 | CAS number: 111-44-4
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
Hydrolysis
Administrative data
Link to relevant study record(s)
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- key study
- Study period:
- From 01-aug-2016 to 16-feb-2017
- Reliability:
- 1 (reliable without restriction)
- Rationale for reliability incl. deficiencies:
- guideline study
- Qualifier:
- according to guideline
- Guideline:
- OECD Guideline 111 (Hydrolysis as a Function of pH)
- Deviations:
- no
- GLP compliance:
- yes (incl. QA statement)
- Specific details on test material used for the study:
- TEST MATERIAL:
- Name (as cited): 2,2’-Dichlorodiethyl ether
- Putiry: 99.76%
SOURCE OF TEST MATERIAL
- Source and lot/batch No.of test material: batch n°20150706
- Expiration date of the lot/batch: 27 June 2017
- Purity test date: not specified
STABILITY AND STORAGE CONDITIONS OF TEST MATERIAL
- Storage condition of test material: Controlled room temperature (15-25 °C, below 70 RH%), protected from light
TREATMENT OF TEST MATERIAL PRIOR TO TESTING
- Treatment of test material prior to testing: no treatment - Radiolabelling:
- no
- Analytical monitoring:
- yes
- Buffers:
- - pH: 4.0; 7.0; 9.0
- Composition of buffer:
pH 4.0: 1 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Potassium hydrogen phthalate was diluted to 500 mL with ultra-pure water
pH 7.0: 74 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Potassium dihydrogen phosphate was diluted to 500 mL with ultra-pure water
pH 9.0: 53.5 mL 0.2 M Sodium hydroxide and 125 mL 0.2 M Boric acid and Potassium chloride was diluted to 500 mL with ultra-pure water - Details on test conditions:
- TEST SYSTEM
- Measures taken to avoid photolytic effects: incubated in the dark
- Test system: closed screw cap tubes
TEST MEDIUM
- Kind and purity of water: steriel ultra-pure water
- Concentration of test substance: 0.005 M test item concentration in each buffer
INCUBATION
- Temperature:: 50°C
-Duration: 5 days - Duration:
- 5 d
- pH:
- 4
- Temp.:
- 50 °C
- Initial conc. measured:
- 0.005 mol/L
- Duration:
- 5 d
- pH:
- 7
- Temp.:
- 50 °C
- Initial conc. measured:
- 0.005 mol/L
- Duration:
- 5 d
- pH:
- 9
- Temp.:
- 50 °C
- Initial conc. measured:
- 0.005 mol/L
- Number of replicates:
- 5 replicates for each pH buffer
- Positive controls:
- no
- Negative controls:
- no
- Statistical methods:
- Not applicable
- Preliminary study:
- Preliminary Test/Tier 1
Sample solutions at pH 4, 7 and 9 were maintained at 50.0 ± 0.5 °C for a period of 5 days. Results from the Preliminary Test/Tier 1 showed it was not necessary to undertake further testing at pH 4, pH 7 and pH 9. - Transformation products:
- not measured
- Details on hydrolysis and appearance of transformation product(s):
- No data
- % Recovery:
- 97
- St. dev.:
- 1.6
- pH:
- 4
- Temp.:
- 50 °C
- Duration:
- 5 d
- Remarks on result:
- hydrolytically stable based on preliminary test
- % Recovery:
- 97.6
- St. dev.:
- 3.2
- pH:
- 7
- Temp.:
- 50 °C
- Duration:
- 5 d
- Remarks on result:
- hydrolytically stable based on preliminary test
- % Recovery:
- 99
- St. dev.:
- 2.3
- pH:
- 9
- Temp.:
- 50 °C
- Duration:
- 5 d
- Remarks on result:
- hydrolytically stable based on preliminary test
- Key result
- pH:
- 4
- Temp.:
- 50 °C
- DT50:
- 113.8 d
- Key result
- pH:
- 7
- Temp.:
- 50 °C
- DT50:
- 142.7 d
- Key result
- pH:
- 9
- Temp.:
- 50 °C
- DT50:
- 344.8 d
- Other kinetic parameters:
- No data
- Validity criteria fulfilled:
- yes
- Conclusions:
- Following a 5 days incubation period, Bis(2-chloroethyl) ether recovery was 97.0, 97.6 and 99.0% at pH 4.0, 7.0 and 9.0 at 50°C, respectively.
- Executive summary:
An hydrolysis study was conducted to evaluate the stability of Bis(2-chloroethyl) ether based on OECD Guideline No. 111 under GLP. The test item was incubated at a concentration of 0.005M for 5 days in the dark at 50°C, and at pH 4.0, 7.0 and 9.0. The samples were analyzed using GC-FID prior or after the 5 days incubation at 50°C and the % recovey was calculated. The percentage recovery was 97.0, 97.6 and 99% at pH 4.0, 7.0 and 9.0, respectively. Accordingly, Bis(2-chloroethyl) ether is considered to be stable at pH 4.0, 7.0 and 9.0.
The data from this study are considered reliable without restriction (Reliability 1).
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- supporting study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- data from handbook or collection of data
- Specific details on test material used for the study:
- TEST MATERIAL
Test material (as cited): Bis(2-chloroethyl) ether
Purity: not specified - Radiolabelling:
- not specified
- Analytical monitoring:
- not specified
- Temp.:
- 100 °C
- Hydrolysis rate constant:
- 0 min-1
- DT50:
- ca. 32 d
- Type:
- not specified
- Remarks on result:
- other: in aqueous dioxane
- Conclusions:
- Bis(2-chlorethyl) ether showed a half-life of 32 days following hydrolysis testing at 100°C. Allowing for a factor of two decrease in rate constant for each 10°C decrement, the half-life is calculated as 22 years (or 256 times slower) at 20°C.
- Executive summary:
The data on hydrolysis of Bis(2-chloroethyl) ether originate from a collection of data published by US EPA (Mabey et al., 1982). U.S. EPA reports are subjected to a formal review process. It is thus assumed that a variety of data sources have been consulted, that the test methodology and identity of the test substance has been evaluated, and that a reliable and representative value for the endpoint has been selected. Accordingly, this data was assigned a reliability score of 2.
A hydrolysis rate constant of 1.5 x 10-5 min-1 has been reported for Bis(2-chloroethyl) ether in aqueous dioxane at 100°C (Bohme & Sell, 1948). This rate constant corresponds to a half-life of 32 days. Allowing for a factor of two decrease in rate constant for each 10°C decrement, the half-life is calculated as 22 years (or 256 times slower) at 20°C. This rate constant is much slower than expected based on a simple analogy to ethyl chloride where a half-life of 38 days is predicted at pH 7 and 25°C (Mabey & Mill, 1978).
The relatively slow hydrolysis rate of Bis(2-chloroethyl) ether compared with ethyl chloride is suggested to be due to the effect on the adjacent carbon of the -OCH2CH2Cl group. Data have been obtained which show that aqueous solvolysis of 2-methoxyethyl iodide at 60°C is 6.4 x 10-3 times the rate of ethyl iodide under the same reaction conditions (Streitwieser, 1962). Assuming that this 6.4 x 10-3 factor holds for the chloroaliphatic compounds as well as for the iodo compounds, the 38 day half-life of ethyl chloride can be used to obtain a half-life of 16 years for Bis(2-chloroethyl) ether. This estimate of the half-life is in fair agreement with the 22 year half-life calculated from the aqueous dioxane solvent data.
Accordingly, Bis(2 -chloroethyl) ether is considered to show a slow hydrolysis rate under environmentally relevant conditions.
- Endpoint:
- hydrolysis
- Type of information:
- experimental study
- Adequacy of study:
- supporting study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- study well documented, meets generally accepted scientific principles, acceptable for assessment
- Qualifier:
- no guideline followed
- Principles of method if other than guideline:
- 2mL pyrex bulbs were filled Bis(2-chloroethyl) ether diluted in MilliQ water (resistivity: 16 MΩ/cm) at pH 6.9. The bulbs were sealed and placed in a thermostatic oil bath at various temperature ranging from 80-95°C. The bulbs were protected from light to prevent photolysis. At regular intervals (duration of incubation not stated), Bis(2-chloroethyl) ether and its degradation products were analysed using GC.
- GLP compliance:
- not specified
- Specific details on test material used for the study:
- Purity: not specified
- Radiolabelling:
- no
- Analytical monitoring:
- yes
- Remarks:
- GC method
- Details on sampling:
- - Sampling intervals for the parent/transformation products: not specified
- Sample storage conditions before analysis: not specified - Buffers:
- No data- pH:
- Type and final molarity of buffer: no data
- Composition of buffer: no data - Details on test conditions:
- No data
- Number of replicates:
- No specified
- Positive controls:
- not specified
- Negative controls:
- not specified
- Transformation products:
- yes
- No.:
- #1
- No.:
- #2
- Details on hydrolysis and appearance of transformation product(s):
- No data
- pH:
- 6.9
- Temp.:
- 80 °C
- DT50:
- 189 h
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 6.9
- Temp.:
- 85 °C
- DT50:
- 109 h
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 6.9
- Temp.:
- 90 °C
- DT50:
- 64 h
- Type:
- (pseudo-)first order (= half-life)
- pH:
- 6.9
- Temp.:
- 95
- DT50:
- 44 h
- Type:
- (pseudo-)first order (= half-life)
- Other kinetic parameters:
- From Arrhenius' law, the activation energy was estimated at 108.3 KJ/mole.
- Validity criteria fulfilled:
- yes
- Conclusions:
- The half-life of Bis(2-chloroethyl) ether in distilled water at pH 6.9 was determined to be 44, 64, 109 and 189 hours at 95, 90, 85 and 80°C, respectively.
- Executive summary:
In this published study, the hydrolysis of Bis(2-chloroethyl) ether in distilled water (pH 6.9) was studied at various temperatures. Samples were added to pyrex bulbs and incubated in a thermostatic oil bath protected from light (to avoid photolysis). Quantification of Bis(2-chloroethyl) ether and its degradation product was obtained using a GC-FID system. The half-life of Bis(2-chloroethyl) ether in distilled water at pH 6.9 was determined to be 44, 64, 109 and 189 hours at 95, 90, 85 and 80°C, respectively. These data were used to extrapolate the half-life of Bis(2-chloroethyl) ether at lower temperatures. This approach suggests that the half-life of the test substance is 202 years at 10°C and 22 years at 25°C. The main degradation products following hydrolysis are 1,4-Dioxane and HCl.
The methdological details of this study are provided in sufficient details. In addition, the data have been subject to peer-review. Accordingly, a relibaility score of 2 has been assigned.
Referenceopen allclose all
The samples were analyzed using GC-FID prior or after the 5 days incubation at 50°C and the % recovey was calculated. The results are as follows:
pH | % recovery |
4.0 | 97.0 +/- 1.6 |
7.0 | 97.6 +/- 3.2 |
9.0 | 99.0 +/- 2.3 |
Description of key information
In a study based on OECD Guideline No. 111, Bis(2-chloroethyl) ether was found to be stable at pH 4.0, 7.0 and 9.0. The test item was incubated at a concentration of 0.005M for 5 days in the dark at 50°C. The samples were analyzed using GC-FID prior or after the 5 days incubation and the % recovey was calculated. Whatever the pH considered (4-9), the percentage recovery was at least 97%. Accordingly, hydrolysis at environmental pH is considered to be very limited. The mean estimated half-life was 200.4 days at pH ranfing from 4 to 9.
Key value for chemical safety assessment
- Half-life for hydrolysis:
- 200.4 d
- at the temperature of:
- 50 °C
Additional information
Three studies on the hydrolysis of Bis(2-chloroethyl ether) are available.
An hydrolysis study was conducted to evaluate the stability of Bis(2-chloroethyl) ether based on OECD Guideline No. 111 under GLP. The test item was incubated at a concentration of 0.005M for 5 days in the dark at 50°C, and at pH 4.0, 7.0 and 9.0. The samples were analyzed using GC-FID prior or after the 5 days incubation at 50°C and the % recovey was calculated. The percentage recovery was 97.0, 97.6 and 99% at pH 4.0, 7.0 and 9.0, respectively. Accordingly, Bis(2-chloroethyl) ether is considered to be stable at pH 4.0, 7.0 and 9.0. The data from this study are considered reliable without restriction (Reliability 1).
In the databook entitled "Aquatic Fate Porcess Data for Organic Priority Pollutants" published by U.S. EPA (Mabey et al., 1982), a hydrolysis rate constant of 1.5 x 10-5min-1has been reported for Bis(2-chloroethyl) ether in aqueous dioxane at 100°C (Bohme & Sell, 1948). This rate constant corresponds to a half-life of 32 days. Allowing for a factor of two decrease in rate constant for each 10°C decrement, the half-life is calculated as 22 years (or 256 times slower) at 20°C. This rate constant is much slower than expected based on a simple analogy to ethyl chloride where a half-life of 38 days is predicted at pH 7 and 25°C (Mabey & Mill, 1978). The relatively slow hydrolysis rate of Bis(2-chloroethyl) ether compared with ethyl chloride is suggested to be due to the effect on the adjacent carbon of the -OCH2CH2Cl group. Data have been obtained which show that aqueous solvolysis of 2-methoxyethyl iodide at 60°C is 6.4 x 10-3times the rate of ethyl iodide under the same reaction conditions (Streitwieser, 1962). Assuming that this 6.4 x 10-3factor holds for the chloroaliphatic compounds as well as for the iodo compounds, the 38 day half-life of ethyl chloride can be used to obtain a half-life of 16 years for Bis(2-chloroethyl) ether. This estimate of the half-life is in fair agreement with the 22 year half-life calculated from the aqueous dioxane solvent data. U.S. EPA reports are subjected to a formal review process. It is thus assumed that a variety of data sources have been consulted, that the test methodology and identity of the test substance has been evaluated, and that a reliable and representative value for the endpoint has been selected. Accordingly, this data was assigned a reliability score of 2.
In a published study by Milano et al. (Environ. Technol. Lett., 1989, 10:291-300), the hydrolysis of Bis(2-chloroethyl) ether in distilled water (pH 6.9) was studied at various temperatures. Samples were added to pyrex bulbs and incubated in a thermostatic oil bath protected from light (to avoid photolysis). Quantification of Bis(2-chloroethyl) ether and its degradation product was obtained using a GC-FID system. The half-life of Bis(2-chloroethyl) ether in distilled water at pH 6.9 was determined to be 44, 64, 109 and 189 hours at 95, 90, 85 and 80°C, respectively. These data were used to extrapolate the half-life of Bis(2-chloroethyl) ether at lower temperatures. This approach suggests that the half-life of the test substance is 202 years at 10°C and 22 years at 25°C. The main degradation products following hydrolysis are 1,4-Dioxane and HCl. The methdological details of this study are provided in sufficient details. In addition, the data have been subject to peer-review. Accordingly, a relibaility score of 2 has been assigned.
Based on an overall assessment of available data, Bis(2-chloroethyl) ether is assumed to exhibit a slow hydrolysis rate under environmentally relevant conditions.
Information on Registered Substances comes from registration dossiers which have been assigned a registration number. The assignment of a registration number does however not guarantee that the information in the dossier is correct or that the dossier is compliant with Regulation (EC) No 1907/2006 (the REACH Regulation). This information has not been reviewed or verified by the Agency or any other authority. The content is subject to change without prior notice.
Reproduction or further distribution of this information may be subject to copyright protection. Use of the information without obtaining the permission from the owner(s) of the respective information might violate the rights of the owner.