Investigations of the structure and reactions of the intermediate in the chlorination of resorcinol

Journal Article · Wed Sep 01 00:00:00 EDT 1993 · Environmental Toxicology and Chemistry; (United States)

DOI:https://doi.org/10.1002/etc.5620120914· OSTI ID:5600574

Heasley, V L; Anderson, M E; Combes, D S; Elias, D S; Gardner, J T; Hernandez, M L; Moreland, R J; Shellhamer, D F ^[1]

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1. Point Loma Nazarene College, San Diego, CA (United States). Dept. of Chemistry

The investigation reported here describes an attempt to establish the structure of the intermediate that undergoes ring-opening in the chlorination of resorcinol and its chloro-derivatives in a nucleophilic solvent such as H[sub 2]O or CH[sub 3]OH. The evidence suggests that the pentachloride and not the tetrachloride is the intermediate that reacts with the nucleophiles. Chlorination reactions were conducted in Ch[sub 3]OH/H[sub 2]O. The structures of the early-generation products from incorporation of CH[sub 3]OH were sufficiently stable to be characterized. These products implicated the pentachloride. Resorcinol, di- and trichlororesorcinol, and the pentachloride gave the same products. The mechanisms of the ring-opening and the reactions leading to the products are described in detail. The assumption is made that the same or similar reactions are involved in the aqueous chlorination of resorcinol, but that decarboxylation and solvolysis reactions rapidly degrade the products immediately following ring-opening.

• OSTI ID: 5600574
• Journal Information: Environmental Toxicology and Chemistry; (United States), Vol. 12:9; ISSN 0730-7268
• Country of Publication: United States
• Language: English

Related Subjects

54 ENVIRONMENTAL SCIENCES
RESORCINOL
CHLORINATION
AQUEOUS SOLUTIONS
DECARBOXYLATION
DRINKING WATER
STRUCTURE-ACTIVITY RELATIONSHIPS
AROMATICS
CHEMICAL REACTIONS
DEVELOPERS
DISPERSIONS
HALOGENATION
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
MIXTURES
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
PHENOLS
POLYPHENOLS
SOLUTIONS
WATER
540220* - Environment
Terrestrial- Chemicals Monitoring & Transport- (1990-)