Phosphororganische Antioxidantien. II. Kinetik und Mechanismus der Zersetzung von Alkylhydroperoxiden durch Esteramide der phosphorigen‐ und Phosphorsäure

Rüger, C.; Arnold, David; Schwetlick, K.

doi:10.1002/prac.19823240503

Cited by 8 publications

References 16 publications

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Phosphororganische Antioxidantien. III. Kinetik und Mechanismus der Cumylhydroperoxidzersetzung durch cyclische Phosphite

1984

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Organophosphorus Antioxidants. III. Kinetics and Mechanism of the Decomposition of Cumyl Hydroperoxide by Cyclic Phosphites The reaction mechanism of cyclic esters of phosphorous acids I to VIII with cumyl hydroperoxide has been studied kinetically by means of 31P n.m.r. spectroscopy, high performance liquid chromatography and iodometric titration. The five‐membered cyclic phosphites (I and II) react with cumyl hydroperoxide to give the corresponding phosphates (AI and AII) and cumyl alcohol. With more hydroperoxide or water they form the open chain phosphate esters (BI and BII) which decompose cumyl hydroperoxide catalytically giving phenol and acetone. Higher membered cyclic phosphites (III to VIII) react with cumyl hydroperoxide to give the corresponding phosphates and alcohol only. The mode of reaction depends on the hydrolysis behaviour of the cyclic phosphates (AI to A VIII). Only fivemembered cyclic phosphites which give easily hydrolyzable phosphates are able to decompose cumyl hydroperoxide catalytically. The nature of the exocyclic group in the phosphites has no influence on this behaviour. The kinetic parameters of the separate reaction steps are given. The ionic mechanism of hydroperoxide decomposition is accompanied by a homolytic one.

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Phosphororganische Antioxidantien. III. Kinetik und Mechanismus der Cumylhydroperoxidzersetzung durch cyclische Phosphite

1984

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Phosphororganische Antioxidatien. X [1]. Über die hydroperoxidzersetzende Wirkung von Phosphiten, Phosphoniten und Thiophosphiten

Köunig¹,

Habicher

Schwetlick

1989

J. Prakt. Chem.

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Organophosphorus Antioxidants. X. The Hydroperoxide Decomposing Action of Phosphites, Phosphonites and Thiophosphites The kinetics and mechanism of reactions of phosphites, phosphonites, thiophosphites and hydrogenphosphites with cumyl (CHP), t‐butyl (TBHP) and α‐tetralyl (THP) hydrogenperoxides has been studied by means of 31P‐n.m.r. spectroscopy, high performance liquid chromatography and iodometric titration. All three valent phosphorus compounds studied initially react with hydroperoxides stoichiometrically to give the corresponding PO products and alcohol. Some species are able to decompose cumyl hydroperoxide catalytically to form phenol and aceton. Acyloin phosphites decompose CHP catalytically after a stoichiometric reaction as thiophosphites do. Tetramethylpiperidinyl phosphites (“HALS‐phosphites”) react with hydroperoxides only stoichiometrically but with high velocity. Phosphonites react with hydroperoxides in the same way as the corresponding phosphites. Their reactivity, however, is much higher. Hydrogenphosphites are less reactive than phosphites in the reaction with hydroperoxides. They are able to act catalytically.

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phosphororganische Antioxidantien. XII. Synthesen und NMR-Spektren phosphororganischer Antioxidantien und verwandter Verbindungen

et al. 1992

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Organophosphorus Antioxidants. XII. Synthesis and N.M.R. Spectroscopy of Organophosphorus Antioxidants and Related Compounds The syntheses of various aliphatic, aromatic, sterically hindered, and cyclic organophosphorus compounds (phosphorous acid esters, ester chlorides and ester amides, hydrogen phosphites, phosphonates and phosphates) are reported, and general procedures for preparation are given. The compounds synthesized were investigated by means of 31P‐, 1H‐ and 13C‐n.m.r. spectroscopy, and the chemical shifts measured are listed.

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Phosphororganische Antioxidantien. II. Kinetik und Mechanismus der Zersetzung von Alkylhydroperoxiden durch Esteramide der phosphorigen‐ und Phosphorsäure

Cited by 8 publications

References 16 publications

Phosphororganische Antioxidantien. III. Kinetik und Mechanismus der Cumylhydroperoxidzersetzung durch cyclische Phosphite

Phosphororganische Antioxidantien. III. Kinetik und Mechanismus der Cumylhydroperoxidzersetzung durch cyclische Phosphite

Phosphororganische Antioxidatien. X [1]. Über die hydroperoxidzersetzende Wirkung von Phosphiten, Phosphoniten und Thiophosphiten

phosphororganische Antioxidantien. XII. Synthesen und NMR-Spektren phosphororganischer Antioxidantien und verwandter Verbindungen

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