Extending the Haloform reaction to non-methyl ketones: Oxidative cleavage of cycloalkanones to dicarboxylic acids using sodium hypochlorite under Phase Transfer Catalysis conditions

Rothenberg, Gadi; Sasson, Yoel

doi:10.1016/0040-4020(96)00816-2

Cited by 15 publications

(3 citation statements)

References 21 publications

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“…Therefore, the reaction was carried out with 25 kHz ultrasound irradiation. The adipic acid was synthesized in 63 % from cyclohexanone oxidized by sodium hypochlorite under PTC (trioctylmethylammoniumc hloride) at 10 ºC within 24 h 15 . While in our system, sodium hypochlorite-oxidation reaction was given adipic acid from cyclohexanol in 94 % yields under ultrasound irradiation within 4 h at 18 ºC and without adding the PTC.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction seems to occur via a classic oxidative cleavage pathway 15 . The cyclohexanol was oxidized to cyclohexanone at first.…”

Section: Resultsmentioning

confidence: 99%

“…Sasson 15 reported the oxidative cleavage of cycloalkanones to dicarboxylic acids at 10 ºC using sodium hypochlorite under phase transfer catalysis conditions, but the reaction time was very long to 24 h 15 . In this paper we wish to report an efficient and practical procedure for the synthesis of adipic acid with the oxidation of cyclohexanol by sodium hypochlorite in water under ultrasound irradiation (Scheme-I).…”

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confidence: 99%

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Synthesis of Adipic Acid Catalyzed by Sodium Hypochlorite under Ultrasound Irradiation

Zhang¹,

Li²

2013

Asian J. Chem.

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Adipic acid is a most important organic synthetic intermediate and mainly used for synthetic fibers: nylon-66, other fields can also be widely used, for example polyurethane, synthetic resin, leather, polyester foam, plastic plasticizers, lubricants, food additives, adhesives, pesticides, dyes, spices, medicine 1. The adipic acid was synthesized usually by the oxidation of cyclohexene, cyclohexanol, cyclohexanone or a mixture of them or electro-oxidation of cyclohexanol 2,3 , with nitric acid, potassium permanganate, molecular oxygen, ozone as the oxidant. Hydrogen peroxide as a safe, gentle, clean, cheap and readily available oxidant, can replace traditional highpolluting oxidants in organic synthesis. But in these over procedures, the expensive and complex catalysts such as, peroxotungstates and peroxomolybdates 4 , ZSM-5 supported metal ions (M/ZSM-5) and N-hydroxyphthalimide (NHPI) 5 , heteropoly complexes 6 , a carbon supported platinum catalyst 7 , Ti-AlSBA15 catalysts 8 , manganese diimine catalysts 9 , Cosubstituted β-zeolites catalysts 10 , Iron-phthalocyanine on zeolite Y 11 , tungstic acid/acidic organic additive 12 , phosphotungstic acid 13 etc. have to be added in the system. Sodium hypochlorite also is a common oxidizing and chlorinating agent in various organic syntheses. Its solution is attractive as industrial oxidants, being cheap and containing a high percentage of available oxygen. Moreover, the salt solutions resulting from the reactions, are relatively harmless to the environment and can be electrolyticalty recycled 14. Ultrasound has increasingly been used in organic synthesis in the last four decades. A large number of organic reactions can be carried out in higher yields, shorter reaction time or milder conditions under ultrasound irradiation. Rothenberg and

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Section: Resultsmentioning

confidence: 99%

“…The reaction seems to occur via a classic oxidative cleavage pathway 15 . The cyclohexanol was oxidized to cyclohexanone at first.…”

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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