Substituted N-hydroxyphthalimides as oxidation catalysts

Novikova, Katerina V.; Kompanets, M. O.; Kushch, О. V.; Kobzev, S. P.; Khliestov, M. M.; Opeida, I. A.

doi:10.1007/s11144-011-0289-0

Cited by 22 publications

(12 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This study complements the papers published thus far on the oxidation of isopropylarenes in the presence of NHPI [6][7][8][9][10][11][12] with respect to the range of the influence of temperature and the electron-donating substituents (methoxy, phenyl) on the course of the reaction as well as catalyst recovery and air application. The oxidation of hydrocarbons 2, 4 and 7 in the presence of NHPI to hydroperoxides are reported for the first time.…”

Section: Introductionsupporting

confidence: 64%

“…The oxidation processes of isopropylaromatic hydrocarbons to hydroperoxides, as recently shown, can be catalyzed by N-hydroxyphthalimide (NHPI) [4][5][6][7][8][9][10][11] as well as its derivatives [12]. Literature data concerning the NHPI-catalyzed oxidation of isopropylarenes are collected in Table 1.…”

Section: Introductionmentioning

confidence: 99%

“…Novikova et al [12] compared the oxidation of cumene in the presence of NHPI and their derivatives: 4-tert-butyl-and 4-carboxyl-N-hydroxypthalimide, N,Ndihydroxypyromellitimide, N-acetoxyphthalimide and N-methoxyphthalimide. They observed that the catalytic activities of the studied catalyst decreased with the increase of the BDE values of the NO-H.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

Orlińska

Zawadiak

2013

Reac Kinet Mech Cat

View full text Add to dashboard Cite

The oxidations of cumene, 4-isopropylbiphenyl, 1-methoxy-4-(1-methylethyl)benzene, 2-isopropylnaphthalene, 2-methoxy-6-(1-methylethyl)naphthalene, 2,6-diisopropylnaphthalene and 4,4 0 -diisopropylbiphenyl to the corresponding hydroperoxides with oxygen, at 60°C, in the presence of N-hydroxyphthalimide (NHPI) and AIBN have been performed. Process inhibition was observed at temperatures above 60°C resulting in lower conversion. A favorable effect of electron-donating substituents (methoxy, phenyl) on the reaction rate were described. NHPI was separated from the cumene oxidation product and recycled 5 times. It has been demonstrated that oxygen can be replaced by air.

show abstract

Section: Introductionsupporting

confidence: 64%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

Orlińska

Zawadiak

2013

Reac Kinet Mech Cat

View full text Add to dashboard Cite

show abstract

“…Unlike initiator radicals involved only in the initial stages of the radical-chain process, the PINO radical takes part in the propagation stage (see Scheme ) and its structure has a significant impact on the oxidation process. For example, the introduction of various electron-withdrawing or -donor substituents into the benzene ring affects the persistence and reactivity of PINO radicals . Nevertheless, as far as we know, a systematic study of the influence of the PINO radicals’ structure on their persistence has not been carried out.…”

Section: Introductionmentioning

confidence: 99%

Kinetics of N-oxyl Radicals’ Decay

et al. 2020

View full text Add to dashboard Cite

N-oxyl radicals of various structures were generated by oxidation of corresponding N-hydroxy compounds with iodobenzene diacetate, [bis(trifluoroacetoxy)]iodobenzene, and ammonium cerium(IV) nitrate in acetonitrile. The decay rate of N-oxyl radicals follows first-order kinetics and depends on the structure of N-oxyl radicals, reaction conditions, and the nature of the solvent and oxidant. The values of the self-decay constants change within 1.4 × 10 −4 s −1 for the 3,4,5,6-tetraphenylphthalimide-N-oxyl radical to 1.4 × 10 −2 s −1 for the 1-benzotriazole-N-oxyl radical. It was shown that the rate constants of the phthalimide-N-oxyl radicalsʼ self-decay with different electron-withdrawing or -donor substituents in the benzene ring are higher than that of the unsubstituted phthalimide-N-oxyl radical in most cases. The solvent effect on the process of phthalimide-N-oxyl radical self-decomposition was investigated. The dependence of the rate constants on the Gutmann donor numbers was shown.

show abstract

“…However, Lanzalunga et al has shown that the rate of oxidation of 1-(4methoxyphenyl)ethanol is possible to increase by introducing electron-withdrawing substituents in NHPI aryl ring, and therefore, the reactivity order parallels the increase of OH BDE in the substituted NHPIs [19]. The effect of the electron-withdrawing substituents on the aromatic ring of NHPI and the stability of the transition state after hydrogen abstraction reaction by the PINO radical was also discussed by others [20][21][22]. After getting positive effects by using the fluorinated alkyl chain in NHPI, our next aim was to investigate the catalytic activity of another lipophilic NHPI derivative by introducing four electronegative fluorine atoms directly in the aryl ring of NHPI.…”

Section: Egyptian Journal Of Chemistrymentioning

confidence: 99%

An Efficient Method for the Catalytic Aerobic Oxidation of Cycloalkanes using 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI)

Guha

Ishii

2021

Egypt. J. Chem.

View full text Add to dashboard Cite

N-Hydroxyphthalimide (NHPI) is known to be an effective catalyst for the oxidation of hydrocarbons. The catalytic activity of NHPI derivatives is generally increased by introducing an electron-withdrawing group on the benzene ring. In a previous report, two NHPI derivatives containing fluorinated alkyl chain were prepared and their catalytic activity was investigated in the oxidation of cycloalkanes. It was found that the fluorinated NHPI derivatives showed better yields for the oxidation reaction. As a continuation of our work with fluorinated NHPI derivatives, our next aim was to investigate the catalytic activity of the NHPI derivatives by introducing fluorine atoms in the benzene ring of NHPI. In the present research, 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI) is prepared and its catalytic activity has been investigated in the oxidation of two different cycloalkanes for the first time. It has been found that F4-NHPI showed higher catalytic efficiency compared with that of the parent NHPI catalyst in the present reactions. The presence of a fluorinated solvent and an additive was also found to accelerate the oxidation.

show abstract

Substituted N-hydroxyphthalimides as oxidation catalysts

Cited by 22 publications

References 23 publications

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide

Kinetics of N-oxyl Radicals’ Decay

An Efficient Method for the Catalytic Aerobic Oxidation of Cycloalkanes using 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI)

Contact Info

Product

Resources

About