Abstract
The epoxidation of turpentine (technical α-pinene), 3-carene, and limonene with aqueous hydrogen peroxide was studied in a new catalytic system employing manganese sulfate, salicylic acid, sodium bicarbonate, and acetonitrile, as a polar solvent. The proposed approach makes it possible to carry out a “chemical separation” of turpentine components, yielding valuable individual derivatives of monoterpenes without the need to isolate individual monoterpene reagents. Specific methods have been developed for the production of α-pinene epoxide, 3-carene epoxide, limonene diepoxide, as well as for two related compounds: 3-carene-5-one and 3-carene-2,5-dione.
Highlights
An epoxidation reaction is one of the important methods for the functionalization of terpenes, with established industrial applications
In our previous communication [34], we studied the epoxidation of β-pinene with hydrogen peroxide in a reaction mixture containing water, sodium bicarbonate, and manganese salts
We extended the application of our catalytic system to other monoterpenes: α-pinene 1, 3-carene
Summary
An epoxidation reaction is one of the important methods for the functionalization of terpenes, with established industrial applications. The most accessible natural monoterpenes are β-pinene, α-pinene 1, 3-carene 2, and limonene 3. The epoxides of these terpenes can be used for the synthesis of intermediates used in various fragrance, perfumery and pharmaceutical preparations [1,2], as well as in substances having a sweet taste [3]. Another promising use of α-pinene epoxide 4 is its transformation into pinocarveol and. One of the limonene epoxides has recently been used as a source of chirality in the synthesis of methylphosphonate oligonucleotides [6]
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