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Environmental fate & pathways

Hydrolysis

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Reference
Endpoint:
hydrolysis
Type of information:
other: Review
Adequacy of study:
weight of evidence
Reliability:
4 (not assignable)
Rationale for reliability incl. deficiencies:
secondary literature
Qualifier:
no guideline followed
Version / remarks:
Review
Principles of method if other than guideline:
This paper is a review.
Preliminary study:
Nitrosodiphenylamine is expected to be stable in water.
Transformation products:
no
Key result
Remarks on result:
other: hydrolytically stable
Executive summary:

Quoting the review: "Nitrosamines, in general, are hydrolytically stable at ambient environmental conditions and are reported to be hydrolyzed only at elevated temperatures in strongly acidic solutions (Fieser and Fieser 1956). Tate and Alexander (1975) reported no hydrolytic degradation of dimethylnitrosamine in their Lake Cayuga water samples over the observation period of 3.5 months. Since acid-catalyzed hydrolysis involves protonation of one of the nitrogen atoms, diphenylnitrosamine should be similarly stable to hydrolysis."

References:

Fieser L.F., Fieser M., 1956. Organic chemistry, 3rd edition. D.C. Health and Co., Boston. 1112p.

Tale R.L., Alexander M., 1975. Stability of nitrosamines in samples of lake water, soil and sewage. J. Natl. Cancer Inst. 54(2), 327 -330.

Description of key information

N-nitroso-N-phenylaniline is not expected to undergo hydrolysis under relevant environmental conditions of temperature and pH. Quoting the review included as a weight of evidence: "Nitrosamines, in general, are hydrolytically stable at ambient environmental conditions and are reported to be hydrolyzed only at elevated temperatures in strongly acidic solutions (Fieser and Fieser 1956). Tate and Alexander (1975) reported no hydrolytic degradation of dimethylnitrosamine in their Lake Cayuga water samples over the observation period of 3.5 months. Since acid-catalyzed hydrolysis involves protonation of one of the nitrogen atoms, diphenylnitrosamine should be similarly stable to hydrolysis."

References:

Fieser L.F., Fieser M., 1956. Organic chemistry, 3rd edition. D.C. Health and Co., Boston. 1112p.

Tale R.L., Alexander M., 1975. Stability of nitrosamines in samples of lake water, soil and sewage. J. Natl. Cancer Inst. 54(2), 327 -330.

Key value for chemical safety assessment

Additional information