Reactions of chlorine with selected aromatic models of aquatic humic material

Journal Article · Thu Jan 31 23:00:00 EST 1980 · Environ. Sci. Technol.; (United States)

DOI:https://doi.org/10.1021/es60162a012· OSTI ID:5676228

Norwood, D L; Johnson, J D; Christman, R F; Hass, J R; Bobenrieth, M J

A series of compounds designed to model the monomeric components of aquatic humic material was reacted with aqueous chlorine at pH 7. Chloroform production and chlorine demand were measured for each compound over varied time periods. All compounds studied produced measurable amounts of chloroform with resorcinol derivatives showing the greatest yields. In addition, the chlorination reactions of resorcinol and 3-methoxy-4-hydroxycinnamic acid were studied in depth with gas chromatography/mass spectrometry (GC/MS). The resorcinol reaction was found to proceed through several chlorinated intermediates, of which the most abundant was 3,5,5-trichlorocyclopent-3-ene-1,2-dione, to chloroform and chlorinated acids. Chlorination of the cinnamic acid derivative produced chlorinated substitution products and chlorophenols, which broke down upon further reaction to chloroacetic acids.

• Research Organization: Univ. of North Carolina, Chapel Hill
• OSTI ID: 5676228
• Journal Information: Environ. Sci. Technol.; (United States), Journal Name: Environ. Sci. Technol.; (United States) Vol. 14:2; ISSN ESTHA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AROMATICS
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
CHLORINATION
CINNAMIC ACID
DEVELOPERS
GROUND WATER
HALOGENATION
HUMIC ACIDS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
MONOCARBOXYLIC ACIDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
PHENOLS
POLYPHENOLS
RESORCINOL
WATER