Registration Dossier

Environmental fate & pathways

Additional information on environmental fate and behaviour

Administrative data

Endpoint:
additional information on environmental fate and behaviour
Type of information:
experimental study
Adequacy of study:
other information
Reliability:
2 (reliable with restrictions)
Rationale for reliability incl. deficiencies:
other: study documented in sufficient detail

Data source

Reference
Reference Type:
publication
Title:
Molecular probe techniques for the identification of reductants in sediments: Evidence for reduction of 2-chloroacetophenone by hydride transfer.
Author:
Smolen JM, Weber EJ, and Tratnyek PG
Year:
1999
Bibliographic source:
Environ Sci Technol 33, 440-445

Materials and methods

Principles of method if other than guideline:
The reduction of 2-chloroacetophenone was examined in anoxic sediment slurries from both freshwater and marine sources.
GLP compliance:
not specified

Test material

Constituent 1
Chemical structure
Reference substance name:
Acetophenone
EC Number:
202-708-7
EC Name:
Acetophenone
Cas Number:
98-86-2
Molecular formula:
C8H8O
IUPAC Name:
1-phenylethan-1-one
Details on test material:
- Name of test material (as cited in study report): acetophenone
- Substance type: aromatic ketone
- Physical state: liquid (mp: ca. 20°C)
- Analytical purity: >97%
- Impurities (identity and concentrations): not reported

Results and discussion

Any other information on results incl. tables

The reduction of 2-chloroacetophenone (2 -CAP) was examined in anoxic sediment slurries from both freshwater and marine sources. Two reduction pathways of 2 -CAP were assumed:

a. hydride transfer to produce 2 -chloro-1 -phenyl ethanol and

b. electron transfer to produce acetophenone and subsequently sec.-phenylethyl alcohol.

Using freshwater sediment, 50% (fresh water pond, Cherokee Park) and 20% (Rock Creek) acetophenone was produced from 2 -CAP. In both marine sediments a 20% conversion each (Young's Bay and Institute Marsh) of 2 -CAP to acetophenone was observed. Acetophenone itself was further transformed by electron transfer to sec.-phenylethyl alcohol. Based on the observations made during temperature studies (conversion increased with increasing temperature), the authors concluded that the transformation of 2 -CAP to acetophenone and sec.-phenylethyl alcohol occurred mainly via abiotic reactions (metallocoenzyms).

Applicant's summary and conclusion

Conclusions:
In tests conducted using freshwater and marine sediments and anaerobic conditions, 2-CAP was transformed via electron transfer to acetophenone and subsequently to sec.-phenylethyl alcohol as could be determined via HPLC and GC/MS. Based on the temperature studies, the conversion of 2-CAP to acetophenone and subsequently sec.-phenylethyl alcohol occured via abiotic reactions (metallocoenzyms).
Executive summary:

The reduction of 2-chloroacetophenone (2 -CAP) was examined in anoxic sediment slurries from both freshwater and marine sources. Two reduction pathways of 2 -CAP were assumed:

a. hydride transfer to produce 2 -chloro-1 -phenyl ethanol and

b. electron transfer to produce acetophenone and subsequently sec.-phenylethyl alcohol.

Using freshwater sediment, 50% (fresh water pond, Cherokee Park) and 20% (Rock Creek) acetophenone was produced from 2 -CAP. In both marine sediments a 20% conversion each (Young's Bay and Institute Marsh) of 2 -CAP to acetophenone was observed. Acetophenone itself was further transformed by electron transfer to sec.-phenylethyl alcohol. Based on the observations made during temperature studies (conversion increased with increasing temperature), the authors concluded that the transformation of 2 -CAP to acetophenone and sec.-phenylethyl alcohol occurred mainly via abiotic reactions (metallocoenzyms).