Cyrene as a green solvent in the pharmaceutical industry

Adaka, Ifeyinwa C.; Uzor, Philip F.

doi:10.1016/b978-0-12-821885-3.00001-3

Cited by 5 publications

(4 citation statements)

References 17 publications

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“…In this field, the selection of the extracting organic solvent is a key point as it should fulfil the following principles: i) be immiscible with DES ; ii) be effective in the extraction of the organic products; and iii) present a favourable sustainable footprint. Taking into account all these points, the biomass derived solvent cyrene was selected as an ideal extracting solvent in our recycling protocol as it accomplishes all the aforementioned principles [49] . For the first three cycles, we observed quantitative conversions of the internal alkyne 3a into benzil ( 4a ) after 24 h of reaction at 110 °C and under air.…”

Section: Resultsmentioning

confidence: 99%

Fe^III‐Based Eutectic Mixtures as Multi‐task and Reusable Reaction Media for Efficient and Selective Conversion of Alkynes into Carbonyl Compounds

Ramos‐Martín

Ríos‐Lombardía

González‐Sabín

et al. 2023

Chemistry A European J

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An efficient, simple and general protocol for the selective hydration of terminal alkynes into the corresponding methyl ketones was developed by using a cheap, easy‐to‐synthesise and sustainable Fe(III)‐based eutectic mixture [FeCl3·6H2O/Gly (3:1)] as both promoter and solvent for the hydration reaction, working: i) under mild (45 ºC) and bench type reaction conditions (air); and ii) in the absence of ligands, co‐catalysts, co‐solvents or toxic, non‐abundant and expensive noble transition metals (Au, Ru, Pd). When the final methyl ketones are solid/insoluble in the eutectic mixture, the hydration reaction takes place in 30 minutes and the obtained methyl ketones can be isolated just by simple decantation of the liquid Fe(III)‐DES, allowing the direct isolation of the desired ketones without VOC solvents. By using this straightforward and simple isolation protocol, we have been able to recycle our Fe(III)‐based eutectic mixture system up to 8 consecutive times. Furthermore, our Fe(III)‐eutectic mixture is able to promote the selective and efficient formal oxidation of internal alkynes into 1,2‐diketones, being the system recycled up to 3 consecutive times. Preliminary investigations on a possible mechanism for the oxidation of the internal alkynes seems to indicate that it proceeds through the formation of the corresponding methyl ketones and α‐chloroketones

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Section: Resultsmentioning

confidence: 99%

Fe^III‐Based Eutectic Mixtures as Multi‐task and Reusable Reaction Media for Efficient and Selective Conversion of Alkynes into Carbonyl Compounds

Ramos‐Martín

Ríos‐Lombardía

González‐Sabín

et al. 2023

Chemistry A European J

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“…In addition, the specific equipment necessary for supercritical CO 2 applications will limit its widespread use. Dihydrolevoglucosenone (DLG) is a dipolar aprotic bio-based solvent obtained from cellulose [36,37], commercially known as Cyrene TM , and has been introduced as a new "green" solvent marketed specifically as an alternative to solvents such as DMF or NMP, which are particularly interesting for CROP of POx. It is reported that DLG is safe to handle, environmentally friendly, highly stable towards oxidation, yet degrades into water and carbon dioxide [27,38].…”

Section: Introductionmentioning

confidence: 99%

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

Borova¹,

Luxenhofer²

2023

Beilstein J. Org. Chem.

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For about the last ten years, poly(2-oxazoline)s have attracted significant attention as potential material for biomedical applications in, e.g., drug delivery systems, tissue engineering and more. Commonly, the synthesis of poly(2-oxazoline)s involves problematic organic solvents that are not ideal from a safety and sustainability point of view. In this study, we investigated the cationic ring-opening polymerization of 2-ethyl-2-oxazoline and 2-butyl-2-oxazoline using a variety of initiators in the recently commercialized "green" solvent dihydrolevoglucosenone (DLG). Detailed 1H NMR spectroscopic analysis was performed to understand the influence of the temperature and concentration on the polymerization process. Size exclusion chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry were performed to determine the molar mass of the resulting polymers. Our work shows clearly that the solvent is not inert under the conditions typically used for the cationic ring-opening polymerization, as evidenced by side products and limited control over the polymerization. However, we could establish that the use of the 2-ethyl-3-methyl-2-oxazolinium triflate salt as an initiator at 60 °C results in polymers with a relatively narrow molar mass distribution and a reasonable control over the polymerization process. Further work will be necessary to establish whether a living polymerization can be achieved by additional adjustments.

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“…In recent years there has been growing interest in exploring solubility and partitioning properties of various compounds. A special attention should be paid for pharmaceuticals and nutraceuticals in green solvents such as ionic liquids [ 28 , 29 , 30 , 31 , 32 ], bio-based solvents including natural deep eutectic solvents (NADES) [ 33 , 34 , 35 , 36 , 37 , 38 , 39 ] and some environmentally friendly synthetic organic solvents, such as ethanol or DMSO and their organic-organic and organic-aqueous mixtures [ 40 , 41 , 42 , 43 ]. The application of multicomponent solvents containing water are interesting because it is possible to replace the environmentally hazardous pure organic solvent with less harmful aqueous mixtures.…”

Section: Introductionmentioning

confidence: 99%

New Screening Protocol for Effective Green Solvents Selection of Benzamide, Salicylamide and Ethenzamide

et al. 2022

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New protocol for screening efficient and environmentally friendly solvents was proposed and experimentally verified. The guidance for solvent selection comes from computed solubility via COSMO-RS approach. Furthermore, solute-solvent affinities computed using advanced quantum chemistry level were used as a rationale for observed solvents ranking. The screening protocol pointed out that 4-formylomorpholine (4FM) is an attractive solubilizer compared to commonly used aprotic solvents such as DMSO and DMF. This was tested experimentally by measuring the solubility of the title compounds in aqueous binary mixtures in the temperature range between 298.15 K and 313.15 K. Additional measurements were also performed for aqueous binary mixtures of DMSO and DMF. It has been found that the solubility of studied aromatic amides is very high and quite similar in all three aprotic solvents. For most aqueous binary mixtures, a significant decrease in solubility with a decrease in the organic fraction is observed, indicating that all systems can be regarded as efficient solvent-anti-solvent pairs. In the case of salicylamide dissolved in aqueous-4FM binary mixtures, a strong synergistic effect has been found leading to the highest solubility for 0.6 mole fraction of 4-FM.

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Cyrene as a green solvent in the pharmaceutical industry

Cited by 5 publications

References 17 publications

Fe^III‐Based Eutectic Mixtures as Multi‐task and Reusable Reaction Media for Efficient and Selective Conversion of Alkynes into Carbonyl Compounds

Fe^III‐Based Eutectic Mixtures as Multi‐task and Reusable Reaction Media for Efficient and Selective Conversion of Alkynes into Carbonyl Compounds

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

New Screening Protocol for Effective Green Solvents Selection of Benzamide, Salicylamide and Ethenzamide

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Cyrene as a green solvent in the pharmaceutical industry

Cited by 5 publications

References 17 publications

FeIII‐Based Eutectic Mixtures as Multi‐task and Reusable Reaction Media for Efficient and Selective Conversion of Alkynes into Carbonyl Compounds

FeIII‐Based Eutectic Mixtures as Multi‐task and Reusable Reaction Media for Efficient and Selective Conversion of Alkynes into Carbonyl Compounds

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

New Screening Protocol for Effective Green Solvents Selection of Benzamide, Salicylamide and Ethenzamide

Contact Info

Product

Resources

About

Fe^III‐Based Eutectic Mixtures as Multi‐task and Reusable Reaction Media for Efficient and Selective Conversion of Alkynes into Carbonyl Compounds

Fe^III‐Based Eutectic Mixtures as Multi‐task and Reusable Reaction Media for Efficient and Selective Conversion of Alkynes into Carbonyl Compounds