Green synthesis of methadone in eutectic solvent

2021 ◽  
pp. 1-12
Author(s):  
Robab Golzadeh ◽  
Mehrdad Mahkam ◽  
Ebrahim Rezaii ◽  
Leila Nazmi Miardan
Keyword(s):  
Hydrogen Bonding ◽  
Choline Chloride ◽  
The Other ◽  
Magnesium Bromide ◽  
Green Solvents ◽  
High Solubility ◽  
Partial Vapor Pressure ◽  
Ethyl Magnesium Bromide ◽  
New Generation ◽  
Thermal And Chemical Stability

Eutectic solvents (DES), have attracted much attention in the last decade. With the advantages of nonflammability, thermal and chemical stability, high solubility and partial vapor pressure, non-toxicity and reasonable prices, these solvents are suggested as useful solvents. On the other hand, the eutectic solvents developed by Abbott are the new generation of ionic liquids. The mixture of eutectics is from an ammonium salt and a hydrogen bonding compound such as urea, acid, amine, and non-toxic amines. Choline chloride and urea, are quite environmentally friendly and are known practically as green solvents. The purpose of the present research is to present the synthesis of diphenyl acetonitrile with 1-dimethylamino-2-chloropropane by a eutectic’s solvent. In addition, methadone is synthesized from the reaction of 2,2-Diphenyl-4-dimethylaminovaleronitrile with ethyl magnesium bromide in the presence of solvent eutectic, which is in optimal and environmentally compatible conditions and by principles of green chemistry.

The Use of Ionic Liquids in Refrigeration

2006 ◽  
Author(s):  
Mihir Sen ◽  
Samuel Paolucci
Keyword(s):  
Ionic Liquids ◽  
Room Temperature ◽  
High Heat ◽  
The Other ◽  
Refrigeration Cycle ◽  
Absorption Refrigeration ◽  
Transfer Coefficients ◽  
High Solubility ◽  
High Heat Capacity ◽  
Thermal And Chemical Stability

Ionic liquids are salts, usually with organic cations and inorganic anions, that are liquid at room temperature. There are a wide variety of ionic liquids that can be synthesized with different properties for different applications. They are generally non-volatile, non-toxic, and non-flammable with high heat capacity, high density, high thermal and chemical stability. We propose its use as an absorbent in an absorption refrigeration cycle. The refrigerant in this case would be a gas such as carbon dioxide. The present work deals with the desirable properties of ionic liquids for this application. For example, the absorbent must have a high solubility, and the heat and mass transfer coefficients of the absorbent-refrigerant solution must be large. The viscosity of the mixture, on the other hand, should not be so large as to make its pumping difficult.

The effect of cation concentration on the nitrogen splitting constant of nitroxide free radicals

1990 ◽  
Vol 55 (10) ◽  
pp. 2377-2380
Author(s):  
Hamza A. Hussain
Keyword(s):  
Hydrogen Peroxide ◽  
Hydrogen Bonding ◽  
Free Radicals ◽  
Esr Spectroscopy ◽  
The Other ◽  
Tetraethylammonium Bromide ◽  
Splitting Constant ◽  
The One ◽  
Positively Charged ◽  
Two Equilibria

Nitroxide free radicals prepared from diethylamine, piperidine and pyrrolidine by oxidation with hydrogen peroxide were studied by ESR spectroscopy. The changes in the 14N splitting constant (aN) caused by the addition of KBr or tetraethylammonium bromide were measured in dependence on the concentration of the ions. For diethylamine nitroxide and piperidine nitroxide, the results are discussed in terms of two equilibria: the one, involving the anion, is associated with a gain or loss of hydrogen bonds to the nitroxide oxygen atom, the other is associated with the formation of solvent shared units involving the cation, which results in changes in the hydrogen bonding strenght. The large increase in the aN value in the case of pyrrolidine nitroxide is explained in terms of an interaction from one side of the positively charged N atom; the increase in aN in the case of diethylamine and piperidine nitroxides is explained in terms of interactions with both sides of the positively charged N atom.

scholarly journals Doubly ionic hydrogen bond interactions within the choline chloride–urea deep eutectic solvent

2016 ◽  
Vol 18 (27) ◽  
pp. 18145-18160 ◽  
Author(s):  
Claire R. Ashworth ◽  
Richard P. Matthews ◽  
Tom Welton ◽  
Patricia A. Hunt
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Computational Analysis ◽  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Hydrogen Bond Interactions

Computational analysis indicates flexibility and diversity in the hydrogen bonding, but limited charge delocalisation, within the choline chloride–urea eutectic.

Structural preferences for the double bond position in some unsaturated 3,3-diphenylpyrrolidines

1970 ◽  
Vol 48 (23) ◽  
pp. 3742-3745 ◽  
Author(s):  
M. M. A. Hassan ◽  
A. F. Casy
Keyword(s):  
Double Bond ◽  
Methyl Iodide ◽  
Quaternary Salt ◽  
Double Bond Position ◽  
Magnesium Bromide ◽  
Free Base ◽  
Spectroscopic Evidence ◽  
Structural Preferences ◽  
Ethyl Magnesium Bromide ◽  
Sole Product

The reaction between 3,3-diphenyl-3-cyano-1-methylpropyl isocyanate and ethyl magnesium bromide leads to 2-ethyl-5-methyl-3,3-diphenyl-1-pyrroline rather than the isomeric 2-ethylidenepyrrolidine. The protonated N-methyl analogue (identical with a major metabolite of methadone) retains the 1-pyrroline structure, but the free base is a cis-trans mixture of the corresponding 2-ethylidenepyrrolidines; the cis Me/Ph isomer preponderates and is the sole product (obtained as a quaternary salt) when the mixture is treated with methyl iodide. 5-Methyl-2-methylene-3,3-diphenylpyrrolidine, a lower homologue of the methadone metabolite, isomerizes to a 1-pyrroline derivative when protonated or methylated. All structural conclusions are based on i.r. and p.m.r. spectroscopic evidence.

Green Synthesis of 2-thioxothiazolidin-4-one Derivatives in Deep Eutectic Solvents via Knoevenagel Condensation

2022 ◽  
Vol 19 ◽  
Author(s):  
Melita Lončarić ◽  
MAJA MOLNAR
Keyword(s):  
Chemical Synthesis ◽  
Green Synthesis ◽  
Environmental Pollution ◽  
Knoevenagel Condensation ◽  
Choline Chloride ◽  
Deep Eutectic Solvents ◽  
Model Reaction ◽  
Methods And Techniques ◽  
New Generation ◽  
Toxic Organic Solvents

Abstract: Recently, more and more researchers are resorting to green methods and techniques to avoid environmental pollution. Accordingly, many researchers have been working on the development of new green synthetic procedures trying to avoid the use of toxic organic solvents. A sustainable concept of green and environmentally friendly solvents in chemical synthesis nowadays encompasses a relatively new generation of solvents called deep eutectic solvents (DESs). DESs often have a dual role in the synthesis, acting as both, solvents and catalysts. In this study, DESs are used in the Knoevenagel synthesis of rhodanine derivatives, with no addition of conventional catalysts. A model reaction of rhodanine and salicylaldehyde was performed in 20 different DESs at 80 °C, in order to find the best solvent, which was further used for the synthesis of the series of desired compounds. A series of rhodanines was synthesized in choline chloride: acetamide (ChCl:acetamide) DES with good to excellent yields (51.4 – 99.7 %).

Synthesis of organophosphorus compounds using ionic liquids

2018 ◽  
Vol 34 (5) ◽  
pp. 727-740 ◽  
Author(s):  
Lavinia Macarie ◽  
Nicoleta Plesu ◽  
Smaranda Iliescu ◽  
Gheorghe Ilia
Keyword(s):  
Ionic Liquids ◽  
Organophosphorus Compounds ◽  
Inorganic Compounds ◽  
Green Solvents ◽  
High Solubility ◽  
Chemical Reagents ◽  
Reaction Media ◽  
Organophosphorus Chemistry ◽  
Synthesis Reactions ◽  
Toxic Organic Solvents

Abstract Organophosphorus chemistry was developed in the last decade by promoting the synthesis reactions using ionic liquids either as solvent or catalyst. Ionic liquids (ILs), the so-called “green solvents”, have gained interest in the synthesis of organophosphorus compounds as alternatives to flammable and toxic organic solvents and catalysts. ILs have beneficial properties because they provide high solubility for many organic and inorganic compounds or metal complexes, have no vapor pressure, and are reusable. Also, in some cases, they can enhance the reactivity of chemical reagents. In this review, we aimed at showing the synthesis of different organophosphorus compounds under green and mild conditions using ILs as reaction media or catalysts, according to a trend developed in the last years. A novel trend is to perform these syntheses under microwave irradiation conditions together with ILs as solvents and catalysts.

scholarly journals Two New Polyiodides in the 4,4´-Bipyridinium Diiodide/Iodine System

2012 ◽  
Vol 67 (1) ◽  
pp. 5-10
Author(s):  
Guido J. Reiss ◽  
Martin van Megen
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Complex I ◽  
The Other ◽  
Cyclic Dimer ◽  
Water Molecules ◽  
Spectroscopic Methods ◽  
Halogen Bonds ◽  
One Dimensional ◽  
Hydroiodic Acid

The reaction of bipyridine with hydroiodic acid in the presence of iodine gave two new polyiodide-containing salts best described as 4,4´-bipyridinium bis(triiodide), C10H10N2[I3]2, 1, and bis(4,4´-bipyridinium) diiodide bis(triiodide) tris(diiodine) solvate dihydrate, (C10H10N2)2I2[I3]2 · 3 I2 ·2H2O, 2. Both compounds have been structurally characterized by crystallographic and spectroscopic methods (Raman and IR). Compound 1 is composed of I3 − anions forming one-dimensional polymers connected by interionic halogen bonds. These chains run along [101] with one crystallographically independent triiodide anion aligned and the other triiodide anion perpendicular to the chain direction. There are no classical hydrogen bonds present in 1. The structure of 2 consists of a complex I144− anion, 4,4´-bipyridinium dications and hydrogen-bonded water molecules in the ratio of 1 : 2 : 2. The I144− polyiodide anion is best described as an adduct of two iodide and two triiodide anions and three diiodine molecules. Two 4,4´-bipyridinium cations and two water molecules form a cyclic dimer through N-H· · ·O hydrogen bonds. Only weak hydrogen bonding is found between these cyclic dimers and the polyiodide anions.

Trivalent chromium electrodeposition using a deep eutectic solvent

2018 ◽  
Vol 65 (5) ◽  
pp. 499-505 ◽  
Author(s):  
Vyacheslav Protsenko ◽  
Lina Bobrova ◽  
Felix Danilov
Keyword(s):  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Diffraction Method ◽  
Trivalent Chromium ◽  
Electrolytic Deposition ◽  
Active Dissolution ◽  
Plating Bath ◽  
Content Type ◽  
Chromium Plating ◽  
New Generation

Purpose This paper aims to investigate the electrolytic deposition of corrosion-resistant chromium coatings from a trivalent chromium plating bath based on deep eutectic solvent, a new generation of room temperature ionic liquids. Design/methodology/approach The electrolyte contained chromium (III) chloride, choline chloride and the additive of extra water. The surface morphology was estimated by means of SEM technique. The microstructure of as-deposited and annealed coatings was studied using X-ray diffraction method. The kinetics of the chromium electrodeposition and the corrosion electrochemical behavior of the coatings were investigated by cyclic voltammetry technique. Findings Chromium coatings with an amorphous type of microstructure are electroplated from this bath. Some carbon and oxygen are included in deposits obtained. The step-wise mechanism of the electrochemical reduction of Cr(III) ions to Cr(0) is detected. The current efficiency in this system sufficiently exceeds that typical of usual aqueous electrolytes. The coatings fabricated using plating bath based on deep eutectic solvent showed enhanced corrosion resistance in an acidic medium: there is no current peak of active dissolution in polarization curve and the corrosion potential shifts to more positive values as compared with “usual” chromium. Originality/value The electrodeposition of chromium coatings from an environmentally acceptable trivalent chromium electrolyte, a deep eutectic solvent containing chloride choline and extra water additive has been investigated for the first time.

A tetranuclear carbonyl fluoro rhenium(I) cluster, [Re(CO)3F]4,4H2O

1981 ◽  
Vol 34 (4) ◽  
pp. 737 ◽  
Author(s):  
E Horn ◽  
MR Snow
Keyword(s):  
Hydrogen Bonding ◽  
Title Compound ◽  
The Other ◽  
Water Molecules ◽  
Molecular Symmetry ◽  
Group 14 ◽  
Full Matrix ◽  
Abstraction Reaction ◽  
R Value ◽  
Silver Fluoride

The title compound has been prepared from Re(CO)5Br by a bromide-abstraction reaction with silver fluoride. It completes the series of known halide clusters of the type [Re(CO)3X]4 (where X = halide). The crystals are tetragonal, space group 14, with a 11.716(5), c 8.988(3) �, and Z 2. The structure was refined by full-matrix least-squares to an R value of 0.027 for 1380 observed reflections. The molecules are cubane-type clusters of Re(CO)3 groups at one set of corners interpenetrated with fluorine atoms at the other set. The clusters exhibit the molecular symmetry 43m. Each of the fluorine atoms is involved in μ3 type bridging with the rhenium atoms at an average bonding distance of 2.200(5) �. The clusters are held together by hydrogen bonding of fluoride to water molecules.

Polymorphs of phenazine hexacyanoferrate(II) hydrate: supramolecular isomerism in a 2D hydrogen-bonded network

2021 ◽  
Vol 77 (2) ◽  
pp. 211-218
Author(s):  
Ivica Cvrtila ◽  
Vladimir Stilinović
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
The Other ◽  
Two Dimensional ◽  
Structural Motifs ◽  
Supramolecular Isomerism ◽  
Other Hand ◽  
Π Stacking ◽  
Hydrogen Bonded

The crystal structures of two polymorphs of a phenazine hexacyanoferrate(II) salt/cocrystal, with the formula (Hphen)3[H2Fe(CN)6][H3Fe(CN)6]·2(phen)·2H2O, are reported. The polymorphs are comprised of (Hphen)2[H2Fe(CN)6] trimers and (Hphen)[(phen)2(H2O)2][H3Fe(CN)6] hexamers connected into two-dimensional (2D) hydrogen-bonded networks through strong hydrogen bonds between the [H2Fe(CN)6]2− and [H3Fe(CN)6]− anions. The layers are further connected by hydrogen bonds, as well as through π–π stacking of phenazine moieties. Aside from the identical 2D hydrogen-bonded networks, the two polymorphs share phenazine stacks comprising both protonated and neutral phenazine molecules. On the other hand, the polymorphs differ in the conformation, placement and orientation of the hydrogen-bonded trimers and hexamers within the hydrogen-bonded networks, which leads to different packing of the hydrogen-bonded layers, as well as to different hydrogen bonding between the layers. Thus, aside from an exceptional number of symmetry-independent units (nine in total), these two polymorphs show how robust structural motifs, such as charge-assisted hydrogen bonding or π-stacking, allow for different arrangements of the supramolecular units, resulting in polymorphism.

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