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Elements Of Chemical Reaction Engineering

Innovative catalysis in Michael addition reactions for C-X bond formation

Chiral N-heterocyclic carbenes (NHCs) have been recently established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. The underlying HOMO-raising acti...

A Bifunctional N-Heterocyclic Carbene as a Noncovalent Organocatalyst for Enantioselective Aza-Michael Addition Reactions

Biodiesels as renewable fuels are important in approaching low-carbon transportation. One critical challenge associated with biodiesel production is the utilization of crude glycerol, an abundant waste byproduct from which glycerol can be obtained via refinement, to maximize economic and environmental benefits. Efforts on crude glycerol and glycerol utilization include direct use (e.g., combustion fuels) and indirect use (e.g., reformation for value-added chemicals). Among different approaches, the direct use as fuels and fuel additives is straightforward and affordable. Recently, significant progress has been made to understand their combustion performance and explore new applications, including fuel additives for reducing emissions and improving the combustion performance of traditional fuels, and fuel for combustion synthesis of valuable materials. The current review discusses these achievements and future outlook on using crude glycerol and glycerol as fuels and fuel additives for combustion applications. Overall, crude glycerol can achieve high-efficiency combustion with the improved design, but ash deposition is still the main challenge. Fortunately, integrating crude glycerol with solid fuels could mitigate ash issues and improve the combustion performance of low-rank solid fuels. In contrast, glycerol is an oxygenated fuel additive for lowering NOx emissions. Furthermore, glycerol is capable as a fuel in combustion material synthesis for manufacturing the raw materials for catalysts, sensors, and battery applications. 

Crude glycerol and glycerol as fuels and fuel additives in combustion applications

The ability of lipases to display activity beyond their physiological reactions, so-called “catalytic promiscuity”, has gained increasing interest in the last two decades as an important tool for expanding the application of these enzymes in organic synthesis. Some lipases have been shown to be effective in catalyzing a variety of C-C bond formation reactions and most of the investigations have been directed to the optimization of the products yield through a careful tuning of the experimental parameters. Despite the fact that new stereogenic carbons are formed in many of the tested reactions, the target products have been often obtained in racemic form and examples of an efficient asymmetric induction by the used lipases are quite limited. The aim of this review, mainly focused on those lipase-catalyzed promiscuous reactions in which optically active products have been obtained, is to offer a current state of art together with a perspective in this field of asymmetric synthesis.

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Stereoselective Promiscuous Reactions Catalyzed by Lipases

Benzylidene malononitrile find applications in pharmaceutical industries, pharmacology, biotech, specialty chemicals, perfumery, and for fluorescence-based assay to determine methane and is produced by polluting routes. Hydrotalcites (HT) have been very effective as solid bases in different reactions and their properties can be changed by using different synthetic methods. In this work, the effect of additional metal in the synthesis of Al-Mg hydrotalcite was systematically studied to prepare Ti-Al-Mg (Ti modified hydrotalcite) and Zn-Al-Mg HT (Zn modified hydrotalcite) using combustion method with glycine as well as glycerol as a fuel. All synthesized catalysts were evaluated in Knoevenagel condensation of benzaldehyde with malononitrile to give benzylidene malononitrile. The catalysts were completely characterized by SEM, EDXS, $$\text {N}_{2}$$
 Adsorption, $$\text {CO}_{2}$$
 -TPD and $$\text {NH}_{3}$$
 -TPD and XRD techniques. Ti-Al-Mg hydrotalcite using glycine as a fuel was found to be the most active, selective and reusable catalyst. Langmuir-Hinshelwood-Hougen-Watson (LHHW) model was used to establish the reaction mechanism and kinetics. All species were weakly adsorbed leading to the second order power law model. Using mole ratio of 1:3 of benzaldehyde to malononitrile with ethyl acetate as a solvent and $$2.5 \times 10^{-4}$$
  g/
 $$\text {cm}^{3}$$
 catalyst loading, 67.1% conversion of benzaldehyde and 97.6% selectivity to benzylidene malononitrile were achieved in 4 h at 60 
 $${^{\circ }}$$
 C. The apparent activation energy was 10.01 kcal/mol. The process is green. Ti-Al-Mg and Zn-Al-Mg hydrotalcites were prepared using combustion method with glycine and glycerol as fuel and used in the Knoevenagel condensation of benzaldehyde with malononitrile to give benzylidene malononitrile. Ti-Al-Mg hydrotalcite (glycine) was the most active, selective and reusable catalyst.

/pdf/clean-synthesis-of-benzylidenemalononitrile-by-knoevenagel-aaw8s1nfzz.pdf

Clean synthesis of benzylidenemalononitrile by Knoevenagel condensation of benzaldehyde and malononitrile: effect of combustion fuel on activity and selectivity of Ti-hydrotalcite and Zn-hydrotalcite catalysts

The activity and selectivity of hydrotalcites (HTs) can be suitably enhanced by the addition of different metal oxides. Zinc and titanium are prospective candidates for such a modification. Transesterification of dimethyl terephthalate (DMT) with ethylene glycol (EG) using basic catalysts is an industrially important process for the production of bis(2-hydroxyethyl)terephthalate (BHET). BHET is a precursor for polyethylene terephthalate (PET) which is used in production of films, fibers, and molding materials. As against use of polluting liquid bases, solid bases could be employed. In the current work, transesterification of DMT with EG was studied over modified HT base catalysts wherein the HT was activated with the addition of zinc and titanium. These catalysts were prepared by the combustion synthesis using different fuels. The modified HT using Zn and Ti were well characterized by scanning electron microscopy, energy-dispersive X-ray spectrometry, Brunauer-Emmett-Teller surface area analyzer, temperature-programmed desorption, and X-ray diffraction. Effects of several parameters on the rate of reaction and conversion of the limiting reagent were investigated. Zinc-modified HT using glycine as fuel (Zn-HT-glycine) was found to be the most selective, active, and reusable catalyst. The Langmuir-Hinshelwood-Hougen-Watson model was used to establish the reaction mechanism and kinetics. All species were weakly adsorbed leading to a second-order kinetics. Using a mole ratio of 1:2 of DMT to EG and 0.05 g/cm3 Zn-HT-glycine loading resulted in to 64.1% conversion of DMT and 96.1% selectivity to BHET in 4 h at 180 °C. The apparent activation energy was 9.64 kcal/mol. The catalyst was robust and reusable.

Zn- and Ti-Modified Hydrotalcites for Transesterification of Dimethyl Terephthalate with Ethylene Glycol: Effect of the Metal Oxide and Catalyst Synthesis Method.

Porous Crosslinked Co3O4 Nanoflakes Synthesized at different pH Media for Electrochemically Charge Storage Applications

Green synthesis of 2,3-oxybutyl malononitrile viamichael reaction of methyl vinyl ketone with malononitrile over titania and zinc loaded hydrotalcite catalysts

Amarsinh L. Jadhav

Papers

Innovative catalysis in Michael addition reactions for C-X bond formation

Clean synthesis of benzylidenemalononitrile by Knoevenagel condensation of benzaldehyde and malononitrile: effect of combustion fuel on activity and selectivity of Ti-hydrotalcite and Zn-hydrotalcite catalysts

Zn- and Ti-Modified Hydrotalcites for Transesterification of Dimethyl Terephthalate with Ethylene Glycol: Effect of the Metal Oxide and Catalyst Synthesis Method.

Porous Crosslinked Co3O4 Nanoflakes Synthesized at different pH Media for Electrochemically Charge Storage Applications

Green synthesis of 2,3-oxybutyl malononitrile viamichael reaction of methyl vinyl ketone with malononitrile over titania and zinc loaded hydrotalcite catalysts