Catalytic Activity of Polymer Anchored Cu-tren Complex in the Oxidation of 2,6-Di-<i>t</i>-butyl Phenol

El‐Hamshary, Hany; Al-Sigeny, Samia; Ibrahim, Mohamed M.

doi:10.1080/10601320903539249

Cited by 9 publications

(5 citation statements)

References 37 publications

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“…Cu II acetate showed a noted exception; it did not require the addition of base, it was active without any base being added and the yield did not change much even after addition of the optimized 10 mol% NaOH. Based on the literature evidences suggesting the deprotonation of OH is the first step [190,206] it seems Cu due to its higher Lewis acidic nature is able to deprotonate the phenolic OH through interaction with the phenol oxygen.…”

Section: Oxidative Coupling Of 2-aminophenol (Oap)mentioning

confidence: 99%

“…H 2 O 2 or t BuOOH as oxidant to give two different oxidation products 3,3 -5,5 -tetra-tertbutyldiphenoquinone (DPQ) and 2,6-di-tert-butylbenzoquinone (BQ) [190,191]. Among the 3d-transition metals, there are more examples of copper [185,186,190,192] and cobalt salts and complexes [188,[193][194][195][196][197][198][199][200][201][202] as catalysts but use of iron and manganese are relatively less [76,187,203]. Organic ligands have also been found to be effective catalyst to form DPQ as major product [204].…”

Section: Oxidative Coupling Of 2-aminophenol (Oap)mentioning

confidence: 99%

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Investigation of 3d-transition metal acetates in the oxidation of substituted dioxolene and phenols

Dey

Mukherjee

2015

Journal of Molecular Catalysis A: Chemical

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Section: Oxidative Coupling Of 2-aminophenol (Oap)mentioning

confidence: 99%

Section: Oxidative Coupling Of 2-aminophenol (Oap)mentioning

confidence: 99%

Investigation of 3d-transition metal acetates in the oxidation of substituted dioxolene and phenols

Dey

Mukherjee

2015

Journal of Molecular Catalysis A: Chemical

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“… (a) Tris(2‐aminoethyl)amine copper (II) complex (Cu(II)‐tren complex); (b) quaternized poly(styrene‐ co ‐dimethylaminoethyl methacrylate); (c) quaternized poly(methyl methacrylate‐ co ‐dimethylaminoethyl methacrylate) …”

Section: Methods Of Alkyl‐14‐benzoquinones Preparationmentioning

confidence: 99%

Alkyl‐1,4‐Benzoquinones – From Synthesis to Application

2016

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Alkyl-1,4-benzoquinones (ABQs) such as 2,3-, 2,5-and 2,6-dimethyl-and 2,6-di-tert-butyl-1,4-benzoquinones are versatile building blocks and also have many others applications known for this type of compounds. Nowadays the requirements of environmental safety necessitate revising preparation processes of such compounds and searching for alternative synthesis ways. Until recently, there have been many efforts to develop sustainable green processes. However, the efficiency of proposed methods differs significantly. For this reason, in this review we would like to outline a variety of chemical properties of ABQs in order to show their great potential as chemical precursors, to describe some interesting applications of ABQs and then to give description of existing ABQ synthesis procedures developed in the last few decades. The review summarizes advances in liquid-phase selective oxidation of alkylphenols with molecular oxygen, hydrogen peroxide, and t-butyl hydroperoxide by using both homogeneous and heterogeneous catalysts. Consideration of old methods for ABQ synthesis is of interest for understanding the evolution of preferences in the field and for comparing the efficiency of methods.Benzoquinones are a versatile class of compounds possessing several sites of potential reactivity, viz. C = C and C = O. Owing to this feature, they may enter into various reactions such as amination, acylation, alkylation and arylation as well as cycloaddition, changing and modifying their structures. [3] Let us give some examples below.Nair et al. demonstrated that zwitterionic species generated by adding cyclohexyl isocyanide [4] or isoquinoline [5] to dimethyl acetylenedicarboxylate can react with C = O bond of quinones, giving iminolactones [Reaction (1)] and derivatives of isoquinoline [Reaction (2)].

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“…The oxidation of DTBP to DPQ is a relatively wellknown reaction, 11 and it is precisely for this reason that it is an excellent candidate for the following proof-of-concept studies. On the other hand, published examples of this transformation occurring in water are few 12,13 and do not involve catalytic surfactants, but rather transition metal catalysts dissolved within the micelle. 12 Slight modifications to published procedures were used to obtain the long chain N-alkyliminodiacetic acids (H 2 C n IDA, where n = 10, 12, 14).…”

mentioning

confidence: 99%

“…As the oxidant concentration was increased, the amount of DPQ decreased, suggesting perhaps the formation of the over-oxidized benzoquinone (BQ) derivative. [11][12][13] When the identical larger-scale reaction was performed with 10 equiv. H 2 O 2 , the residue isolated by extraction displayed a product distribution of 85% DPQ and 7% BQ by NMR, with an additional 8% DTBP remaining unreacted.…”

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confidence: 99%

Oxidative C–C coupling of 2,6-di-tert-butylphenol in aqueous media via catalytically active molybdate surfactants

2013

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Long-chain N-alkyliminodiacetatomolybdate catalytic surfactants can be incorporated within a CTAB micellar solution and have shown catalytic activity for the oxidation of 2,6-di-tert-butylphenol to the corresponding diphenoquinone in aqueous media. Scheme 1 Synthesis of molybdate surfactants. † Electronic supplementary information (ESI) available: Experimental details regarding synthesis of Na 2 MoO 3 C 12 IDA, determination of the CMC, catalysis conditions and measurement of DPQ. See

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Catalytic Activity of Polymer Anchored Cu-tren Complex in the Oxidation of 2,6-Di-t-butyl Phenol

Cited by 9 publications

References 37 publications

Investigation of 3d-transition metal acetates in the oxidation of substituted dioxolene and phenols

Investigation of 3d-transition metal acetates in the oxidation of substituted dioxolene and phenols

Alkyl‐1,4‐Benzoquinones – From Synthesis to Application

Oxidative C–C coupling of 2,6-di-tert-butylphenol in aqueous media via catalytically active molybdate surfactants

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