Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-04-14
1997-04-15
Diamond, Alan D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
8107, 8101, 8111, 549330, 549513, 549523, 549524, 568 27, 568 28, 564298, C07B 3300, C07D32100, D21C 916
Patent
active
056211180
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB92/01879 filed Oct. 14, 1992.
This invention is concerned with a process for oxidising substrates susceptible to nucleophilic oxidation. More particularly, though not exclusively,. the present invention is concerned with a process for the preparation of dioxiranes by reacting a bicaroate (HSO.sub.5.sup.-), obtained from Caro's acid or monopersulphate with a ketone.
Murray et al, J. Org. Chem., Vol. 50, No. 16, 1985, pages 2847 to 2853, discloses a process for the in-situ preparation of dioxiranes by reacting, in a reaction zone, a bicaroate or monopersulphate with acetone. The bicaroate or monopersulphate is added dropwise to an acetone solution (i.e. to a liquid phase which is predominantly organic and potentially having a low flash point), and the dioxirane is produced in a liquid phase solution comprising a low concentration of dioxirane and excess of unreacted acetone. In other papers, such as by Adam et al in J Org Chem 1987, 52, 2800-2803, a carrier gas or reduced pressure is suggested as a means of stripping product from the reaction mixture.
It is an object of the present invention to provide a new or improved oxidation process for substrates susceptible to nucleophilic oxidation.
It is a further object of the present invention to provide a new or improved process for the preparation of a dioxirane.
In accordance with a first aspect of the present invention, there is provided a process for oxidising a substrate susceptible to nucleophilic oxidation by reacting, in a reaction zone, a bicaroate or monopersulphate solution with the substrate and the process is characterised in that the substrate is introduced into the reaction zone in a gaseous phase with a gaseous carrier, which is inert to nucleophilic oxidation, and the oxidised substrate so produced is extracted from the reaction zone in a gaseous phase with the inert gaseous carrier.
In accordance with a second aspect of the present invention, there is provided a process for the oxidation of a substrate susceptible to nucleophilic oxidation by reacting, in a reaction zone, a bicaroate or monopersulphate solution with the substrate and the process is characterised by in Step (a) neutralising an aqueous Caro's acid solution with at least an equimolar equivalent of base in at least two stages, by a process which comprises (1) reacting the Caro's acid with less than an equimolar equivalent of base to form a mixture of bicaroate and Caro's acid, (2) removing a proportion of the heat generated by the reaction of Step (a)(1) from the mixture formed in Step (a)(1), (3) reacting the mixture formed in Step (a)(2) with the remaining amount of base to form a final solution, which solution preferably has a pH of from 7 to 9, more preferably from 7.5 to 8.5; and
in Step (b) reacting said substrate with at least partially neutralised Caro's acid solution to form oxidised substrate when the solution has or attains an approximately neutral or alkaline pH.
Substrates suitable for oxidation by the process of the present invention will be apparent to those skilled in the art. Typically, such substrates include ketones, tertiary amines, sulphides and electrophilic olefins.
In accordance with a third aspect of the present invention, there is provided a process for the preparation of a dioxirane by reacting, in a reaction zone, a bicaroate or monopersulphate with a ketone and the process is characterised in that the ketone is introduced into the reaction zone in a gaseous phase with a gaseous carrier, inert to nucleophilic oxidation, and the dioxirane so produced is extracted from the reaction zone in a gaseous phase with the inert gaseous carrier.
In a fourth aspect, the present invention provides a process for the preparation of a dioxirane by reacting, in a reaction zone, a bicaroate or monopersulphate solution with a ketone characterised by in Step (a) neutralising an aqueous Caro's acid solution with at least an equimolar equivalent of base in at least two stages, by a process which comprises (1) reacting the Caro's acid with les
REFERENCES:
patent: 5087752 (1992-02-01), Murray et al.
Jones Craig W.
Sanderson William R.
Sankey John P.
Diamond Alan D.
Solvay Interox Limited
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