17336-81-1

Basic information

• Product Name: Cyclohexanone, 2,2-dichloro-
• Synonyms: Cyclohexanone, 2,2-dichloro-
• CAS NO: 17336-81-1
• Molecular Formula: C₆H₈Cl₂O
• Molecular Weight: 0
• Mol File: 17336-81-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexanone, 2,2-dichloro-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2,2-dichloro-(17336-81-1)
• EPA Substance Registry System: Cyclohexanone, 2,2-dichloro-(17336-81-1)

Safety Data

• Hazardous Substances Data: 17336-81-1(Hazardous Substances Data)

Upstream product

• 822-87-7 2-Chlorocyclohexanone 
• 18709-01-8 cyclohexanone-2-carboxylic acid 
• 55949-64-9 1,6-Dichlor-7-oxabicyclo<4.1.0>heptan 
• 108-94-1 cyclohexanone 

Downstream Products

• 10557-33-2 cis-2,6-dichlorocyclohexanone 
• 6498-39-1 2-chlorocyclohex-2-en-1-ol 
• 3400-88-2 2-chlorocyclohex-2-en-1-one 
• 91446-60-5 2-chloro-cyclohex-2-enone-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

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Extending the haloform reaction to non-methyl ketones: Oxidative cleavage of cycloalkanones to dicarboxylic acids using sodium hypochlorite under phase transfer catalysis conditions

Cyclohexanone is readily oxidized to adipic, α,α-dichloroadipic, glutaric and succinic acids by sodium hypochlorite under phase transfer conditions. The selectivity is highly dependent on the pH of the reacting system. A consecutive chlorination-hydrolysis mechanism is proposed in which only cyclohexanone is a reactive substrate leading in parallel to the melange of oxidized products. Cyclooctanone and cyclopentanone are similarly oxidized.

Reactions of alicyclic ketones in carbon tetrachloride. II. Kinetics of the chlorination of 2-chlorocyclopentanone and 2-chlorocyclohexanone, catalyzed by hydrogen chloride

The kinetics of the direct chlorination of 2-chlorocyclopentanone (2-mccp) and 2-chlorocyclohexanone (2-mcch) in carbon tetrachloride, catalyzed by hydrogen chloride, were studied.Reaction products are all the possible 2,2-, 2,5-, and 2,6-dichloro compounds.The ratios depend on the concentrations of the monochloro compound and hydrogen chloride.Surprisingly, even at conversions of the monochloro compound as low as 2percent, 2,2,5-trichlorocyclopentanone and 2,2,6-trichlorocyclohexanone, respectively, are also formed.The chlorination of both monochloro ketones shows zero order in chlorine.The order in hydrogen chloride is 1.3.The order in 2-mccp and 2-mcch varies somewhat with the concentration of the ketone and was found to be roughly 1.7.The variation in reaction order is explained by a partial self-association of the ketones.The ketones act as substrates as well as basic catalysts in the rate-determining α- or α'-carbon deprotonation.General base catalysis is clearly demonstrated by a strong increase in the rate of chlorination of 2-mccp upon addition of cyclopentanone (cp) to the reaction mixture, which agrees with the mechanism as presented in a previous paper.Kinetic equations derived from the reaction models for the "separate" and "mixed" ketone chlorinations accurately describe the observed rates of the chlorination of 2-mccp and 2-mcch in the concentration range of 0.04 - 1.0 M.