Acetophenone

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

Test material information

Constituent 1

Reference substance name:

Acetophenone

EC Number:

202-708-7

EC Name:

Acetophenone

Cas Number:

98-86-2

Molecular formula:

C8H8O

IUPAC Name:

1-phenylethanone

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).