Continuous nitration of alcohols in a Freon flow

Zharkov, Mikhail N.; Arabadzhi, Svetlana S.; Kuchurov, Ilya V.; Zlotin, Sergei G.

doi:10.1039/c9re00035f

Cited by 14 publications

(11 citation statements)

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“…Zlotin et al studied the nitration of alcohols under continuous flow conditions. 112 Dinitrogen pentoxide served as nitrating agent, and liquid 1,1,1,2-tetrafluoroethane (Freon R134a) as reaction medium. Freon R134a is an inert, non-flammable gas that has the potential to replace chlorinated solvents that are commonly utilized for nitration reactions with dinitrogen pentoxide.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Continuous Flow Upgrading of Selected C₂–C₆Platform Chemicals Derived from Biomass

et al. 2020

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The ever increasing industrial production of commodity and specialty chemicals inexorably depletes the finite primary fossil resources available on Earth. The forecast of population growth over the next 3 decades is a very strong incentive for the identification of alternative primary resources other than petro-based ones. In contrast with fossil resources, renewable biomass is a virtually inexhaustible reservoir of chemical building blocks. Shifting the current industrial paradigm from almost exclusively petro-based resources to alternative bio-based raw materials requires more than vibrant political messages; it requires a profound revision of the concepts and technologies on which industrial chemical processes rely. Only a small fraction of molecules extracted from biomass bears significant chemical and commercial potentials to be considered as ubiquitous chemical platforms upon which a new, bio-based industry can thrive. Owing to its inherent assets in terms of unique process experience, scalability, and reduced environmental footprint, flow chemistry arguably has a major role to play in this context. This review covers a selection of C2 to C6 bio-based chemical platforms with existing commercial markets including polyols (ethylene glycol, 1,2-propanediol, 1,3-propanediol, glycerol, 1,4-butanediol, xylitol, and sorbitol), furanoids (furfural and 5-hydroxymethylfurfural) and carboxylic acids (lactic acid, succinic acid, fumaric acid, malic acid, itaconic acid, and levulinic acid). The aim of this review is to illustrate the various aspects of upgrading bio-based platform molecules toward commodity or specialty chemicals using new process concepts that fall under the umbrella of continuous flow technology and that could change the future perspectives of biorefineries.

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Section: Chemical Reviewsmentioning

confidence: 99%

“…Figure 50. Zlotin's continuous process for the manufacture of nitroglycerine in liquid Freon R134a 112. …”

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Continuous Flow Upgrading of Selected C₂–C₆Platform Chemicals Derived from Biomass

et al. 2020

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“…DNP can be used in nitration reactions almost stoichiometrically, thus signicantly reducing the amounts of acidic wastes. 10,35,36 Moreover, their composition becomes more narrow. The Kyodai nitration protocol using NO 2 /O 3 mixtures, in which DNP can be in situ generated, also falls in this category of the nitration processes.…”

Section: Introductionmentioning

confidence: 99%

“…There are hardly any challenges in the TFE recycling since it is characterized by a relatively low saturated vapor pressure (0.6 MPa and 20 C). 35,54,56 Herein, we applied for the rst time the DNP/TFE nitrating system for the clean, effective, and safe preparation of nitroarenes.…”

Section: Introductionmentioning

confidence: 99%

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Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium

et al. 2021

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Overcoming Challenges in O‐Nitration: Selective Alcohol Nitration Deploying N,6‐Dinitrosaccharin and Lewis Acid Catalysis

Fernandes,

Valsamidou,

Katayev

2024

Angewandte Chemie

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Nitrate esters hold pivotal roles in pharmaceuticals, energetic materials, and atmospheric processes, motivating the development of efficient synthesis routes. Here, we present a novel catalytic method for the synthesis of nitrates via the direct O‐nitration of alcohols, addressing limitations of current traditional methods. Leveraging bench‐stable and recoverable N,6‐dinitrosaccharin reagent, our catalytic strategy employs magnesium triflate to achieve mild and selective O‐nitration of alcohols, offering broad substrate scope and unprecedented large functional group tolerance (e.g. alkenes, alkynes, carbonyls). DFT mechanistic studies reveal a dual role of the magnesium catalyst in the activation of both the nitrating reagent and the alcohol substrate. They also unveil a barrierless proton transfer upon formation of a widely‐accepted — yet elusive in solution — nitrooxonium ion intermediate. Overall, our work contributes to the development of mild, selective, and sustainable approaches to nitrates synthesis, with potential applications in drug discovery, materials science, and environmental chemistry.

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Continuous nitration of alcohols in a Freon flow

Abstract: The first ever installation for continuous nitration in a liquefied gas mobile phase was developed.

Cited by 14 publications

References 24 publications

Continuous Flow Upgrading of Selected C₂–C₆Platform Chemicals Derived from Biomass

Continuous Flow Upgrading of Selected C₂–C₆Platform Chemicals Derived from Biomass

Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium

Overcoming Challenges in O‐Nitration: Selective Alcohol Nitration Deploying N,6‐Dinitrosaccharin and Lewis Acid Catalysis

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Continuous nitration of alcohols in a Freon flow

Abstract: The first ever installation for continuous nitration in a liquefied gas mobile phase was developed.

Cited by 14 publications

References 24 publications

Continuous Flow Upgrading of Selected C2–C6Platform Chemicals Derived from Biomass

Continuous Flow Upgrading of Selected C2–C6Platform Chemicals Derived from Biomass

Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium

Overcoming Challenges in O‐Nitration: Selective Alcohol Nitration Deploying N,6‐Dinitrosaccharin and Lewis Acid Catalysis

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Continuous Flow Upgrading of Selected C₂–C₆Platform Chemicals Derived from Biomass

Continuous Flow Upgrading of Selected C₂–C₆Platform Chemicals Derived from Biomass