kilomentor

One key to imaginative and rugged chemical process development is extractive separations which are general for functional groups besides acids and bases. Many years ago now, a short paper was published which taught how to selectively extract only aldehydes. into water as areversible complex and thence isolate them.

This type of activity is known for aqueous sodium bisulfite and this newer method is compared with sodium bisulfite in the article. The method is more selective.Sodium bisulfite also forms adducts with methyl ketones and some cyclic ketones. The sodium bisulfite method seems to gibe problems with aldehydes that do not have some water solubility. The paper is: Shunsaku Ohta and Masao Okamoto, Chem. Pharm. Bull. 28(6) 1917-1919(1980). The abstract reads: An aqueous solution of sodium epsilon- amino-n-caproate can be used for efficient and simple separation of aldehydes, overcoming the difficulties associated with the sodium bisulfite method.

From my own experience the method works for aldehydes like in the examples, but I do not know how high a molecular weight can be transported effectively into the aqueous phase. Although the paper uses diisopropyl ether, I have used the more available and less peroxide prone diethyl ether. There are no later papers citing this paper,. It is as if the paper has been lost. There is also no hypothesized mechanism for the extraction. Personally, I think some kind of emulsion or microemulsion is formed from the imine from the aldehyde and the reagent which traps the aldehyde inside the emulsion particles dissolved in the aqueous phase.

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• Common Ground for Generic and Innovator Pharmaceutical Companies
• Biocatalytic Methods of Enantioselective Synthesis in Pharmaceutical Process Development
• Separation by Substantial Differences in Chemical Reactivity of the Same Nominal Functional Group.
• Sulfate Pharmaceutical Salts (reprint to remove comments)
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• The Complete Blog for the Preparation of Pharmaceutical Salts

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