Searching for novel reusable biomass-derived solvents: furfuryl alcohol/water azeotrope as a medium for waste-minimised copper-catalysed azide–alkyne cycloaddition

2016 ◽  
Vol 18 (23) ◽  
pp. 6380-6386 ◽  
Author(s):  
Dace Rasina ◽  
Aurora Lombi ◽  
Stefano Santoro ◽  
Francesco Ferlin ◽  
Luigi Vaccaro
Keyword(s):  
Organic Chemistry ◽  
Click Chemistry ◽  
Furfuryl Alcohol ◽  
Reaction Medium ◽  
Alcohol Water ◽  
Water Azeotrope

Herein we report the first application of the furfuryl alcohol/water azeotrope as a sustainable and easily recoverable reaction medium for organic chemistry. As first applicantion we have defined a waste-oinimized protocol for click-chemistry synthesi of 1,2,3-triazoles.

A waste-minimized protocol for copper-catalyzed Ullmann-type reaction in a biomass derived furfuryl alcohol/water azeotrope

2018 ◽  
Vol 20 (7) ◽  
pp. 1634-1639 ◽  
Author(s):  
Francesco Ferlin ◽  
Valeria Trombettoni ◽  
Lorenzo Luciani ◽  
Soliver Fusi ◽  
Oriana Piermatti ◽  
...  
Keyword(s):  
Furfuryl Alcohol ◽  
Bidentate Ligand ◽  
Aryl Halides ◽  
Aliphatic Amines ◽  
Type Reaction ◽  
Alcohol Water ◽  
Water Azeotrope

We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines.

Reactivity and selectivity under microwaves in organic chemistry. Relation with medium effects and reaction mechanisms

2001 ◽  
Vol 73 (1) ◽  
pp. 161-166 ◽  
Author(s):  
André Loupy ◽  
Laurence Perreux ◽  
Marion Liagre ◽  
Karine Burle ◽  
Michel Moneuse
Keyword(s):  
Organic Chemistry ◽  
Reaction Mechanisms ◽  
Reaction Medium ◽  
Solvent Free ◽  
Microwave Activation ◽  
Medium Effects ◽  
Specific Effects ◽  
Solvent Free Conditions

Typical applications of solvent-free conditions and microwave activation are described. Non-purely thermal specific effects are evidenced and discussed in terms of reaction medium and mechanisms, taking into account the variations in polarity of the systems.

Ethenesulfonyl Fluoride (ESF) and Its Derivatives in SuFEx Click Chemistry and More

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 673-687 ◽  
Author(s):  
Yan-Ping Meng ◽  
Shi-Meng Wang ◽  
Wan-Yin Fang ◽  
Zhi-Zhong Xie ◽  
Jing Leng ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Click Chemistry ◽  
Exchange Reaction ◽  
Organic Synthesis ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
Click Reaction ◽  
Chemical Properties ◽  
Chemical Transformations ◽  
Absolute Reliability

The sulfur(VI) fluoride exchange reaction (SuFEx), developed by Sharpless and co-workers in 2014, is a new category of click reaction that creates molecular connections with absolute reliability and unprecedented efficiency through a sulfur(VI) hub. Ethenesulfonyl fluoride (ESF), as one of the most important sulfur(VI) hubs, exhibits extraordinary reactivity in SuFEx click chemistry and organic synthesis. This review summarizes the chemical properties and applications of ESF in click chemistry, organic chemistry, materials science, medicinal chemistry and in many other fields related to organic synthesis.1 Introduction2 Chemical Transformations of ESF3 Chemical Transformations of 2-Arylethenesulfonyl Fluorides4 Novel SuFEx Reagents Derived from ESF5 Applications of ESF Derivatives in Medicinal Chemistry6 Applications of ESF Derivatives in Materials Science7 Conclusion

scholarly journals Synthesis of tetraalkyl thiuram disulfides using different oxidants in recycling solvent mixture

2012 ◽  
Vol 18 (1) ◽  
pp. 73-81 ◽  
Author(s):  
Milutin Milosavljevic ◽  
Aleksandar Marinkovic ◽  
Jelena Markovic ◽  
Danijela Brkovic ◽  
Milan Milosavljevic
Keyword(s):  
Isopropyl Alcohol ◽  
Level Structure ◽  
Reaction Medium ◽  
Solvent Mixture ◽  
Azeotropic Mixture ◽  
Water Mixture ◽  
Alcohol Water ◽  
High Yields ◽  
Industrial Level ◽  
Laboratory Synthesis

A new optimized laboratory synthesis of tetraalkyl thiuram disulfides, starting from dialkyl amines and carbon disulfide in presence of three oxidants (hydrogen peroxide, potassium peroxodisulfate and sodium hypochlorite) and appropriate reaction medium: two mixtures of isopropyl alcohol - water used in two consecutive syntheses, was presented in this work. First synthesis was performed in a recycled azeotropic mixture of isopropyl alcohol - water 87.7% - 12.3%, and second in a filtrate obtained after first synthesis, which was a mixture of isopropyl alcohol - water 70.4% - 29.6%. After the second synthesis and filtration, recycled azeotropic mixture isopropyl alcohol - water 87.7% - 12.3% was regenerated from the filtrate by rectification. Considering this, the technology for beneficial use of recycling isopropyl alcohol - water mixture as reaction medium for tetraalkyl thiuram disulfides synthesis was developed. Such concept contributes to extraordinary economical benefit of implemented optimal laboratory synthesis at semi-industrial level. High yields of tetraalkyl thiuram disulfides syntheses were obtained at both laboratory and semiindustrial level. Structure and purity of synthesized compounds were confirmed by elemental analysis, as well as FTIR, 1H and 13C NMR, and MS spectral data.

Methods to improve flux during alcohol/water azeotrope separation by vapor permeation

1992 ◽  
Vol 68 (3) ◽  
pp. 229-239 ◽  
Author(s):  
A.E. Jansen ◽  
W.F. Versteeg ◽  
B. van Engelenburg ◽  
J.H. Hanemaaijer ◽  
B.Ph. ter Meulen
Keyword(s):  
Vapor Permeation ◽  
Alcohol Water ◽  
Water Azeotrope

Illuminating a Path for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

Synlett ◽  
2021 ◽  
Author(s):  
Bruce H. Lipshutz
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Reaction Medium ◽  
Base Metals ◽  
Bottom Line ◽  
Reactive Metal ◽  
Metal Chemistry ◽  
The Past ◽  
Environmentally Responsible ◽  
Petroleum Reserves

AbstractA personalized account is presented describing some of the stories behind the scenes in efforts to convert organic chemistry into a more sustainable discipline. These are part of a group ‘crusade’ started almost 15 years ago aimed at providing technologies illustrative of how key reactions used today can be ‘faster, better, cheaper’ when run in recyclable water. Hence, the option now exists to do organic synthesis in a far more environmentally responsible fashion. By contrast, most of organic chemistry developed over the past 200 years that relies on organic solvents continues to generate enormous amounts of pollution, while depleting finite petroleum reserves and our supplies of many precious and base metals. Making the switch to water, Nature’s chosen reaction medium, akin to that in which bio-catalysis is typically performed, is inevitable.1 The Story Begins: A Different Type of Prejudice2 Are We up to the Challenge? Too Late Now…3 ‘Impossible’ Reactive Metal Chemistry in Water4 Didn’t I Once Say: ‘It’s All about the Ligand’?5 What Happens When Our Supply of Palladium Runs Out?6 What Are the Implications from These Tales for Today and Tomorrow?7 What Is the ‘Broader Impact’ of This Work?8 The Bottom Line…

scholarly journals Green Synthesis of Privileged Benzimidazole Scaffolds Using Active Deep Eutectic Solvent

Molecules ◽  
2019 ◽  
Vol 24 (16) ◽  
pp. 2885 ◽  
Author(s):  
Maria Luisa Di Gioia ◽  
Roberta Cassano ◽  
Paola Costanzo ◽  
Natividad Herrera Cano ◽  
Loredana Maiuolo ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Pharmaceutical Industry ◽  
Deep Eutectic Solvent ◽  
Reaction Medium ◽  
Building Blocks ◽  
Synthetic Methods ◽  
Benzimidazole Derivatives ◽  
The Face ◽  
Analgesic Activities ◽  
Work Up

The exploitation and use of alternative synthetic methods, in the face of classical procedures that do not conform to the ethics of green chemistry, represent an ever-present problem in the pharmaceutical industry. The procedures for the synthesis of benzimidazoles have become a focus in synthetic organic chemistry, as they are building blocks of strong interest for the development of compounds with pharmacological activity. Various benzimidazole derivatives exhibit important activities such as antimicrobial, antiviral, anti-inflammatory, and analgesic activities, and some of the already synthesized compounds have found very strong applications in medicine praxis. Here we report a selective and sustainable method for the synthesis of 1,2-disubstituted or 2-substituted benzimidazoles, starting from o-phenylenediamine in the presence of different aldehydes. The use of deep eutectic solvent (DES), both as reaction medium and reagent without any external solvent, provides advantages in terms of yields as well as in the work up procedure of the reaction.

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