Regioselective nitration of 2- and 4-nitrotoluenes over systems comprising nitric acid, an acid anhydride and a zeolite

Smith, Keith; Alotaibi, Mohammad Hayal; El‐Hiti, Gamal A.; Arabia, Saudi

doi:10.3998/ark.5550190.p008.788

Cited by 3 publications

(1 citation statement)

References 26 publications

(53 reference statements)

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“…Our research group has developed many processes for the production of valuable materials through regioselective aromatic substitution reactions over reusable solids such as zeolites [16][17][18][19]. The procedures allowed the production of paraor linear isomers in high yields in alkylation [20,21], acylation [22,23], methanesulphonylation [24], and nitration [25][26][27][28][29][30][31] of aromatic compounds. For example, remarkable regioselectivity was achieved in dialkylation of naphthalene with tert-butyl alcohol in cyclohexane over zeolite H-mordenite to produce 2,6-di-tert-butylnaphthalene in high yield (60%), along with 2,7-di-tert-butylnaphthalene and 2-tert-butylnaphthalene in 1% and 10% yields, respectively [21] and pure 2,6-di-tert-butylnaphthalene could be crystallised directly from the product mixture.…”

Section: Research Group Background In Selective Aromatic Substitution Reactionsmentioning

confidence: 99%

Development of Efficient and Selective Processes for the Synthesis of Commercially Important Chlorinated Phenols

Smith

El‐Hiti

2021

Organics

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para-Selective processes for the chlorination of phenols using sulphuryl chloride in the presence of various sulphur-containing catalysts have been successfully developed. Several chlorinated phenols, especially those derived by para-chlorination of phenol, ortho-cresol, meta-cresol, and meta-xylenol, are of significant commercial importance, but chlorination reactions of such phenols are not always as regioselective as would be desirable. We, therefore, undertook the challenge of developing suitable catalysts that might promote greater regioselectivity under conditions that might still be applicable for the commercial manufacture of products on a large scale. In this review, we chart our progress in this endeavour from early studies involving inorganic solids as potential catalysts, through the use of simple dialkyl sulphides, which were effective but unsuitable for commercial application, and through a variety of other types of sulphur compounds, to the eventual identification of particular poly(alkylene sulphide)s as very useful catalysts. When used in conjunction with a Lewis acid such as aluminium or ferric chloride as an activator, and with sulphuryl chloride as the reagent, quantitative yields of chlorophenols can be obtained with very high regioselectivity in the presence of tiny amounts of the polymeric sulphides, usually in solvent-free conditions (unless the phenol starting material is solid at temperatures even above about 50 °C). Notably, poly(alkylene sulphide)s containing longer spacer groups are particularly para-selective in the chlorination of m-cresol and m-xylenol, while, ones with shorter spacers are particularly para-selective in the chlorination of phenol, 2-chlorophenol, and o-cresol. Such chlorination processes result in some of the highest para/ortho ratios reported for the chlorination of phenols.

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Section: Research Group Background In Selective Aromatic Substitution Reactionsmentioning

confidence: 99%

Development of Efficient and Selective Processes for the Synthesis of Commercially Important Chlorinated Phenols

Smith

El‐Hiti

2021

Organics

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A Simple Process for the Synthesis of Novel Pyrazolyltriazole and Dihydropyrazolylthiazole Derivatives as Antimicrobial Agents

et al. 2017

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Organic Synthesis via Renewable Heterogeneous Nanocatalysts Based on Montmorillonite Clay

Al-Abayechi,

Al-Nayili,

Balakit

et al. 2024

COC

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Synthetic organic molecules are vital for human life, serving as medications, pesticides, dyes, and food additives. Organic synthesis provides routes for the production of these molecules. The traditional methods of organic synthesis require energy, solvents, time, and certain conditions based on the nature of the reactions. To address the issues associated with conventional processes, various environmentally friendly (green) methodologies have been developed. Catalysts are crucial in many chemical methods. Chemists aim to develop catalysts that are cost-effective, easy to recover, and can be synthesized with high catalytic activity and renewability. Natural montmorillonite clay is an ideal material for efficient catalysts since it satisfies all these requirements. This review focuses on the recent advances in the development of renewable nanocatalysts made from montmorillonite to be used for the synthesis of various organic compounds.

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Regioselective nitration of 2- and 4-nitrotoluenes over systems comprising nitric acid, an acid anhydride and a zeolite

Cited by 3 publications

References 26 publications

Development of Efficient and Selective Processes for the Synthesis of Commercially Important Chlorinated Phenols

Development of Efficient and Selective Processes for the Synthesis of Commercially Important Chlorinated Phenols

A Simple Process for the Synthesis of Novel Pyrazolyltriazole and Dihydropyrazolylthiazole Derivatives as Antimicrobial Agents

Organic Synthesis via Renewable Heterogeneous Nanocatalysts Based on Montmorillonite Clay

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