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Sustainable Conversion of Carbon Dioxide: An Integrated Review of Catalysis and Life Cycle Assessment

CO2 conversion covers a wide range of possible application areas from fuels to bulk and commodity chemicals and even to specialty products with biological activity such as pharmaceuticals. In the present review, we discuss selected examples in these areas in a combined analysis of the state-of-the-art of synthetic methodologies and processes with their life cycle assessment. Thereby, we attempted to assess the potential to reduce the environmental footprint in these application fields relative to the current petrochemical value chain. This analysis and discussion differs significantly from a viewpoint on CO2 utilization as a measure for global CO2 mitigation. Whereas the latter focuses on reducing the end-of-pipe problem “CO2 emissions” from todays’ industries, the approach taken here tries to identify opportunities by exploiting a novel feedstock that avoids the utilization of fossil resource in transition toward more sustainable future production. Thus, the motivation to develop CO2-based chemistry does not depend primarily on the absolute amount of CO2 emissions that can be remediated by a single technology. Rather, CO2-based chemistry is stimulated by the significance of the relative improvement in carbon balance and other critical factors defining the environmental impact of chemical production in all relevant sectors in accord with the principles of green chemistry.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H317NO – PubChem

 

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Synthesis of Ethylene Glycol from Syngas via Oxidative Double Carbonylation of Ethanol to Diethyl Oxalate and Its Subsequent Hydrogenation

This work reports a novel sustainable two-step method for the synthesis of ethylene glycol (EG) using syngas. In the first step, diethyl oxalate was selectively synthesized via oxidative double carbonylation of ethanol and carbon monoxide (CO) using a ligand-free, recyclable Pd/C catalyst. In the second step, the diethyl oxalate produced underwent subsequent hydrogenation using [2-(di-tert-butylphosphinomethyl)-6-(diethylaminomethyl)pyridine]ruthenium(II) chlorocarbonyl hydride to get EG and ethanol. Thus, the generated ethanol can be recycled back to the first step for double carbonylation. This method gives a sustainable route to manufacture EG using carbon monoxide and hydrogen.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H957NO – PubChem

 

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Cinchona Alkaloid Catalyzed Sulfa-Michael Addition Reactions Leading to Enantiopure beta-Functionalized Cysteines

Sulfa-Michael additions to alpha,beta-unsaturated N-acylated oxazolidin-2-ones and related alpha,beta-unsaturated alpha-amino acid derivatives have been enantioselectively catalyzed by Cinchona alkaloids functionalized with a hydrogen bond donating group at the C6? position. The series of Cinchona alkaloids includes known C6? (thio)urea and sulfonamide derivatives and several novel species with a benzimidazole, squaramide or a benzamide group at the C6? position. The sulfonamides were especially suited as bifunctional organocatalysts as they gave the products in very good diastereoselectivity and high enantioselectivity. In particular, the C6? sulfonamides catalyzed the reaction with the alpha,beta-unsaturated alpha-amino acid derivatives to afford the products in a diastereomeric ratio as good as 93:7, with the major isomer being formed in an ee of up to 99%. The products of the organocatalytic sulfa-Michael addition to alpha,beta-unsaturated alpha-amino acid derivatives were subsequently converted in high yields to enantiopure beta-functionalized cysteines suitable for native chemical ligation.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H370NO – PubChem

 

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Base-promoted aminoethylation of thiols with 2-oxazolidinones: A simple synthesis of 2-aminoethyl sulfides

A simple synthesis of 2-aminoethyl sulfides using a base-promoted reaction of 2-oxazolidinones with thiols is described. An application of this method to the synthesis of chiral 2-aminoethyl sulfides and sulfur-containing heterocyclic compounds is also presented.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H640NO – PubChem

 

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Rhodium(II)-catalyzed c-h functionalization of electron-deficient methyl groups

Enantioselective C-H functionalization of relatively electron-deficient methyl sites was achieved with the combination of 2,2,2-trichloroethyl aryldiazoacetates and tetrakis(triarylcyclopropanecarboxylate) dirhodium catalysts. The substrate scope of the transformation was relatively broad, and C-H functionalization products were furnished with excellent levels of enantioselectivity. As a strategic reaction, crotonate derivatives give 1,6-dicarbonyl compounds, which are useful for further diversification.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H531NO – PubChem

 

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Expanding the scope of the acyl-type radical addition reactions promoted by SmI2

N-Acyl oxazolidinones of simple carboxylic acids and amino acids were observed to undergo successful SmI2-promoted couplings with substituted acrylamides and acrylates, affording a variety of functionalized gamma-ketoamides and -esters with yields attaining 85%. As many of these reductive couplings were previously found to be ineffective employing the corresponding 4-pyridylthio esters, the applicability of this methodology has been substantially improved. The methodology has been adapted to prepare structures related to two potent aspartate protease inhibitors, the renin inhibitor aliskiren, and the gamma-secretase inhibitor L-685,458. Finally, a convenient two-step procedure for the preparation of N-acyl oxazolidinones of N-protected amino acids, which provides consistently good yields of the corresponding imide, has been devised.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H680NO – PubChem

 

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Biarylpyrazolyl oxadiazole as potent, selective, orally bioavailable cannabinoid-1 receptor antagonists for the treatment of obesity

Since the CB1 cannabinoid receptor antagonist 1 (SR141716, rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. In the present study, biarylpyrazole analogues based on a pyrazole core coupled with 1,3,4-oxadiazole were synthesized and tested for CB1 receptor binding affinity. Thorough SAR studies to optimize pyrazole substituents as well as 1,3,4-oxadiazole ring led to several novel CB1 antagonists with IC50 ? 1 nM for the CB1 receptor binding. Among these analogues, we identified 2-(4-((1H-1,2,4-triazol- 1-yl)methyl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl) -5-(1-(trifluoromethyl)cyclopropyl)-1,3,4-oxadiazole 43c as a promising precandidate for the development as an antiobesity agent.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1031NO – PubChem

 

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ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS

Described herein are compounds that are antagonists of PGD2 receptors. Also described are pharmaceutical compositions and medicaments that include the antagonists of PGD2 receptors described herein, as well as methods of using such antagonists of PGD2 receptors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other PGD2-dependent or PGD2-mediated conditions or diseases.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H127NO – PubChem

 

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Palladium(II)-Catalyzed Amidation of Alkenes

PdCl2(MeCN)2 catalyzes amidation of electron-deficient alkenes leading to enamides, where cyclic carbamates are more reactive than cyclic amides as nucleophiles.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H618NO – PubChem

 

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Thermal Degradation of Morpholine in CO2 Post-combustion Capture

Aqueous monoethanolamine (MEA) has been used as benchmark solvent in CO2 capture systems due to its fast absorption kinetics, high cyclic capacity and low cost. However, operational challenges make MEA potentially less attractive, and therefore; there has been a high demand to develop new solvent systems, such as morpholine (MOR). Accordingly, in this work, thermal degradation studies using MEA or MOR have been conducted under stripper conditions in a post-combustion CO2 capture system to identify operational challenges associated with amines degradation. The comparison of MEA and MOR degradation shows that MOR is more thermally stable when compared with MEA in the presence of CO2 at stripper operating conditions studied here. Initial test results identified 1-(2-Hydroxyethyl)-2-imidazolidinone as thermal degradation of MEA, but they were not observed for MOR. Published by Elsevier Ltd.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H867NO – PubChem