Peroxides, their preparation process and use
AssigneeAkzo Nobel N.V.
InventorsAnna Gerdine Van De Bovenkamp-Bouwman, Joachim Willem J. Van Gendt, John Meijer, Bart Fischer, Andreas Herman Hogt
Life of this patent
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Abstract
The invention relates to a preparation process for making peroxy esters and peroxy carbonates, peroxy ester peroxy carbonates, mixed diperoxides, mixed diperoxy esters, and mixed diperoxy carbonates, and to specific monoperoxy esters, monoperoxy carbonates, mixed peroxides, mixed diperoxy esters, mixed diperoxy carbonates, peroxy ester peroxy carbonates, and mixtures thereof. The process involves the reaction of a type-3 ketone peroxide with a reactive carbonyl compound and optional subsequent reaction with an alkyl vinyl ether, acetal, halogen formate, or carboxylic acid anhydride.
Claims8
A process for the preparation of the mixed peroxy ester or mixed peroxy carbonate having the formula IV, with the oxygen in parentheses being absent for the peroxy ester and present for the peroxy carbonate:
- wherein R1, R2, R5, R6 and R7 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, or R1 and R2 form a C3-C12 cycloalkyl group, which alkyl groups may include linear or branched alkyl moieties, and each of R1, R2, R5, R6 and R7 may optionally be substituted with one or more groups selected from hydroxy, alkoxy, linear or branched alkyl, aryloxy, halogen, ester, carboxy, nitrile, and amido, R3 and R4 are independantly selected from the group consisting of C1-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, which groups may include linear or branched alkyl moieties, and each of R3 and R4 may optionally be substituted with one or more groups selected from hydroxy, alkoxy, linear or branched alkyl, aryloxy, halogen, ester, carboxy, nitrile, and amido,
- any pair of the optionally substituted R4, R5, R6 and R7 may form a ring, which process comprises the reaction of the corresponding monoperoxy ester or monoperoxy carbonate with the formula I, with the oxygen in the parentheses being absent for the monoperoxy ester and present for the monoperoxy carbonate:
- wherein R1, R2, and R3 have the identified meaning, with an alkyl vinyl ether with the formula Va or with an acetal with the formula Vb:
- wherein R4-R7 have the same meanings as given above, in the presence of a catalyst.
A process for the preparation of a mixed diperoxy ester and a peroxy ester peroxy carbonate having the formula VI, with the oxygen in parentheses being absent for the diperoxy ester and present for the peroxy ester peroxy carbonate:
- wherein R1 and R2 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, or R1 and R2 form a C3-C12 cycloalkyl group, which alkyl groups may include linear or branched alkyl moieties, and each of R1 and R2 may optionally be substituted with one or more groups selected from hydroxy, alkoxy, linear or branched alkyl, aryloxy, halogen, ester, carboxy, nitrile, and amido, and R3 and R8 are mutually different and independently selected from the group consisting of C1-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, which groups may include linear or branched alkyl moieties, and each of R3 and R8 may optionally be substituted with one or more groups selected from hydroxy, alkoxy, linear or branched alkyl, aryloxy, halogen, ester, carboxy, nitrile, and amido, in which process monoperoxy ester or monoperoxy carbonate with the formula I, with the oxygen in parentheses being absent for the monoperoxy ester and present for the monoperoxy carbonate:
- wherein R1, R2, and R3 have the same meanings as given above, is reacted with a carboxylic acid anhydride with the formula VII:
- in the presence of an acid catalyst.
A process for the preparation of a mixed diperoxy carbonate having the formula VIII:
- wherein R1 and R2 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, or R1 and R2 form a C3-C20 cycloalkyl group, which alkyl groups may include linear or branched alkyl moieties, and each of R1 and R2 may optionally be substituted with one or more groups selected from hydroxy, alkoxy, linear or branched alkyl, aryloxy, halogen, ester, carboxy, nitrile, and amido, and R3 and R9 are independently selected from the group consisting of C1-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 aralkyl, and C7-C20 alkaryl, which groups may include linear or branched alkyl moieties, and R3 and R9 may optionally be substituted with one or more group selected from hydroxy, alkoxy, linear or branched alkyl, aryloxy, halogen, ester, carboxy, nitrile, and amido, which process comprises the reaction of the monoperoxy carbonate with the formula I′:
- with a halogen formate with the formula III′:
- with the proviso that R9 is not identical with R3.
Dependencies are inferred from the claim text.