Oxidation of olefins with H2O2 catalyzed by gallium(III) nitrate and aluminum(III) nitrate in solution

Dalmo Mandelli; Yuriy N. Kozlov; Cezar A R da Silva; Wagner A. Carvalho; Paolo P. Pescarmona; Daniele de A Cella; Polyana T. de Paiva; Georgiy B. Shul'pin

doi:10.1016/j.molcata.2016.03.004

Oxidation of olefins with H₂O₂ catalyzed by gallium(III) nitrate and aluminum(III) nitrate in solution

Dalmo Mandelli, Yuriy N. Kozlov, Cezar A R da Silva, Wagner A. Carvalho, Paolo P. Pescarmona, Daniele de A Cella, Polyana T. de Paiva, Georgiy B. Shul'pin^*

^*Corresponding author for this work

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Abstract

Soluble gallium and aluminum nitrates (simple salts of non-transition metals) are good catalysts for the epoxidation of olefins (cyclooctene, dec-1-ene) including terpenes (carvone, limonene) with hydrogen peroxide in ethyl acetate or tetrahydrofurane (THF). Typically, the gallium salt is more efficient in comparison with the aluminum derivative. Products are formed in yields up to 93%, turnover numbers (TONs) attained 40. Addition of trifluoroacetic acid or pyrazine-2-carboxylic acid (PCA) accelerates the reaction and improves the yield. In striking contrast, added 2,2′-bipyridine or phenanthroline dramatically inhibit the oxidation.

Original language	English
Pages (from-to)	216-220
Number of pages	5
Journal	Journal of Molecular Catalysis A: Chemical
Volume	422
DOIs	https://doi.org/10.1016/j.molcata.2016.03.004
Publication status	Published - 2016

Keywords

Carvone
Epoxidation
Limonene
Olefins
Terpenes

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Oxidation of olefins with H2O2 catalyzed by gallium(III) nitrate and aluminum(III)Final publisher's version, 775 KBLicence: Taverne

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@article{346bd580d21747489be13d179b84b8f6,

title = "Oxidation of olefins with H2O2 catalyzed by gallium(III) nitrate and aluminum(III) nitrate in solution",

abstract = "Soluble gallium and aluminum nitrates (simple salts of non-transition metals) are good catalysts for the epoxidation of olefins (cyclooctene, dec-1-ene) including terpenes (carvone, limonene) with hydrogen peroxide in ethyl acetate or tetrahydrofurane (THF). Typically, the gallium salt is more efficient in comparison with the aluminum derivative. Products are formed in yields up to 93%, turnover numbers (TONs) attained 40. Addition of trifluoroacetic acid or pyrazine-2-carboxylic acid (PCA) accelerates the reaction and improves the yield. In striking contrast, added 2,2′-bipyridine or phenanthroline dramatically inhibit the oxidation.",

keywords = "Carvone, Epoxidation, Limonene, Olefins, Terpenes",

author = "Dalmo Mandelli and Kozlov, {Yuriy N.} and {da Silva}, {Cezar A R} and Carvalho, {Wagner A.} and Pescarmona, {Paolo P.} and Cella, {Daniele de A} and {de Paiva}, {Polyana T.} and Shul'pin, {Georgiy B.}",

year = "2016",

doi = "10.1016/j.molcata.2016.03.004",

language = "English",

volume = "422",

pages = "216--220",

journal = "Journal of Molecular Catalysis A: Chemical",

issn = "1381-1169",

}

TY - JOUR

T1 - Oxidation of olefins with H2O2 catalyzed by gallium(III) nitrate and aluminum(III) nitrate in solution

AU - Mandelli, Dalmo

AU - Kozlov, Yuriy N.

AU - da Silva, Cezar A R

AU - Carvalho, Wagner A.

AU - Pescarmona, Paolo P.

AU - Cella, Daniele de A

AU - de Paiva, Polyana T.

AU - Shul'pin, Georgiy B.

PY - 2016

Y1 - 2016

N2 - Soluble gallium and aluminum nitrates (simple salts of non-transition metals) are good catalysts for the epoxidation of olefins (cyclooctene, dec-1-ene) including terpenes (carvone, limonene) with hydrogen peroxide in ethyl acetate or tetrahydrofurane (THF). Typically, the gallium salt is more efficient in comparison with the aluminum derivative. Products are formed in yields up to 93%, turnover numbers (TONs) attained 40. Addition of trifluoroacetic acid or pyrazine-2-carboxylic acid (PCA) accelerates the reaction and improves the yield. In striking contrast, added 2,2′-bipyridine or phenanthroline dramatically inhibit the oxidation.

AB - Soluble gallium and aluminum nitrates (simple salts of non-transition metals) are good catalysts for the epoxidation of olefins (cyclooctene, dec-1-ene) including terpenes (carvone, limonene) with hydrogen peroxide in ethyl acetate or tetrahydrofurane (THF). Typically, the gallium salt is more efficient in comparison with the aluminum derivative. Products are formed in yields up to 93%, turnover numbers (TONs) attained 40. Addition of trifluoroacetic acid or pyrazine-2-carboxylic acid (PCA) accelerates the reaction and improves the yield. In striking contrast, added 2,2′-bipyridine or phenanthroline dramatically inhibit the oxidation.

KW - Carvone

KW - Epoxidation

KW - Limonene

KW - Olefins

KW - Terpenes

U2 - 10.1016/j.molcata.2016.03.004

DO - 10.1016/j.molcata.2016.03.004

M3 - Article

SN - 1381-1169

VL - 422

SP - 216

EP - 220

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

ER -