Commenced in January 2007
Frequency: Monthly
Edition: International
Paper Count: 12

Green Chemistry Related Abstracts

12 Characterization of Pectinase from Local Microorganisms to Support Industry Based Green Chemistry

Authors: Sasangka Prasetyawan, Anna Roosdiana, Diah Mardiana, Suratmo

Abstract:

Pectinase are enzymes that hydrolyze pectin compounds. The use of this enzyme is primarily to reduce the viscosity of the beverage thus simplifying the purification process. Pectinase activity influenced by microbial sources . Exploration of two types of microbes that Aspergillus spp. and Bacillus spp. pectinase give different performance, but the use of local strain is still not widely studied. The aim of this research is exploration of pectinase from A. niger and B. firmus include production conditions and characterization. Bacillus firmus incubated and shaken at a speed of 200 rpm at pH variation (5, 6, 7, 8, 9, 10), temperature (30, 35, 40, 45, 50) °C and incubation time (6, 12, 18, 24, 30, 36 ) hours. Media was centrifuged at 3000 rpm, pectinase enzyme activity determined. Enzyme production by A. niger determined to variations in temperature and pH were similar to B. firmus, but the variation of the incubation time was 24, 48, 72, 96, 120 hours. Pectinase crude extract was further purified by precipitation using ammonium sulfate saturation in fraction 0-20 %, 20-40 %, 40-60 %, 60-80 %, then dialyzed. Determination of optimum conditions pectinase activity performed by measuring the variation of enzyme activity on pH (4, 6, 7, 8, 10), temperature (30, 35, 40, 45, 50) °C, and the incubation time (10, 20, 30, 40, 50) minutes . Determination of kinetic parameters of pectinase enzyme reaction carried out by measuring the rate of enzyme reactions at the optimum conditions, but the variation of the concentration of substrate (pectin 0.1 % , 0.2 % , 0.3 % , 0.4 % , 0.5 % ). The results showed that the optimum conditions of production of pectinase from B. firmus achieved at pH 7-8.0, 40-50 ⁰C temperature and fermentation time 18 hours. Purification of pectinase showed the highest purity in the 40-80 % ammonium sulfate fraction. Character pectinase obtained : the optimum working conditions of A. niger pectinase at pH 5 , while pectinase from B. firmus at pH 7, temperature and optimum incubation time showed the same value, namely the temperature of 50 ⁰C and incubation time of 30 minutes. The presence of metal ions can affect the activity of pectinase , the concentration of Zn 2 + , Pb 2 + , Ca 2 + and K + and 2 mM Mg 2 + above 6 mM inhibit the activity of pectinase .

Keywords: Green Chemistry, Aspergillus niger, pectinase, Bacillus firmus

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11 Glycerol-Based Bio-Solvents for Organic Synthesis

Authors: Dorith Tavor, Adi Wolfson

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In the past two decades a variety of green solvents have been proposed, including water, ionic liquids, fluorous solvents, and supercritical fluids. However, their implementation in industrial processes is still limited due to their tedious and non-sustainable synthesis, lack of experimental data and familiarity, as well as operational restrictions and high cost. Several years ago we presented, for the first time, the use of glycerol-based solvents as alternative sustainable reaction mediums in both catalytic and non-catalytic organic synthesis. Glycerol is the main by-product from the conversion of oils and fats in oleochemical production. Moreover, in the past decade, its price has substantially decreased due to an increase in supply from the production and use of fatty acid derivatives in the food, cosmetics, and drugs industries and in biofuel synthesis, i.e., biodiesel. The renewable origin, beneficial physicochemical properties and reusability of glycerol-based solvents, enabled improved product yield and selectivity as well as easy product separation and catalyst recycling. Furthermore, their high boiling point and polarity make them perfect candidates for non-conventional heating and mixing techniques such as ultrasound- and microwave-assisted reactions. Finally, in some reactions, such as catalytic transfer-hydrogenation or transesterification, they can also be used simultaneously as both solvent and reactant. In our ongoing efforts to design a viable protocol that will facilitate the acceptance of glycerol and its derivatives as sustainable solvents, pure glycerol and glycerol triacetate (triacetin) as well as various glycerol-triacetin mixtures were tested as sustainable solvents in several representative organic reactions, such as nucleophilic substitution of benzyl chloride to benzyl acetate, Suzuki-Miyaura cross-coupling of iodobenzene and phenylboronic acid, baker’s yeast reduction of ketones, and transfer hydrogenation of olefins. It was found that reaction performance was affected by the glycerol to triacetin ratio, as the solubility of the substrates in the solvent determined product yield. Thereby, employing optimal glycerol to triacetin ratio resulted in maximum product yield. In addition, using glycerol-based solvents enabled easy and successful separation of the products and recycling of the catalysts.

Keywords: Green Chemistry, Sustainability, Catalysis, glycerol

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10 Nano-Zinc Oxide: A Powerful and Recyclable Catalyst for Chemospecific Synthesis of Dicoumarols Based on Aryl Glyoxals

Authors: F. Jafari, S. GharehzadehShirazi, S. Khodabakhshi

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An efficient, simple, and environmentally benign procedure for the one-pot synthesis of dicoumarols was reported. The reaction entails the condensation of aryl glyoxals and 4-hydroxyxoumarin in the presence of catalytic amount of zinc oxide nanoparticles (ZnO NPs) as recyclable catalyst in aqueous media. High product yields and use of clean conditions are important factors of green chemistry.Part of our continued interest to achieve high atom economic reactions by the use safe catalysts. The reaction mixture was refluxed with catalytic amount (3 mol%) of zinc oxide nanoparticles.Reducing the amount of toxic waste and byproducts arising from chemical reactions is an important issue in the context of green chemistry. In comparison with commonly organic solvents, the aqueous media is cheaper and more environmentally friendly. Avoiding the use of organic solvents is an important way to prevent waste in chemical processes. In the context of green and sustainable chemistry, one ofthe most promising approaches is the use of water as the reaction media. In recent years, there has been increasing recognition that water is an attractive media for manyorganic reactions. Using water continues to attract wide attention among synthetic chemists in the design of new synthetic methods.

Keywords: Green Chemistry, Catalyst, zinc oxide, dicoumarol, aryl glyoxal

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9 Sulfonic Acid Functionalized Ionic Liquid in Combinatorial Approach: A Recyclable and Water Tolerant-Acidic Catalyst for Friedlander Quinoline Synthesis

Authors: Jafar Akbari

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Quinolines are very important compounds partially because of their pharmacological properties which include wide applications in medicinal chemistry. notable among them are antimalarial drugs, anti-inflammatory agents, antiasthamatic, antibacterial, antihypertensive, and tyrosine kinase inhibiting agents. Despite quinoline usage in pharmaceutical and other industries, comparatively few methods for their preparation have been reported.The Friedlander annulation is one of the simplest and most straightforward methods for the synthesis of poly substituted quinolines. Although, modified methods employing lewis or br¢nsted acids have been reported for the synthesis of quinolines, the development of water stable acidic catalyst for quinoline synthesis is quite desirable. One of the most remarkable features of ionic liquids is that the yields can be optimized by changing the anions or the cations. Recently, sulfonic acid functionalized ionic liquids were used as solvent-catalyst for several organic reactions. We herein report the one pot domino approach for the synthesis of quinoline derivatives in Friedlander manner using TSIL as a catalyst. These ILs are miscible in water, and their homogeneous system is readily separated from the reaction product, combining advantages of both homogeneous and heterogeneous catalysis. In this reaction, the catalyst plays a dual role; it ensures an effective condensation and cyclization of 2-aminoaryl ketone with second carbonyl group and it also promotes the aromatization to the final product. Various types of quinolines from 2-aminoaryl ketones and β-ketoesters/ketones were prepared in 85-98% yields using the catalytic system of SO3-H functionalized ionic liquid/H2O. More importantly, the catalyst could be easily recycled for five times without loss of much activity.

Keywords: Green Chemistry, ionic liquid, antimalarial drugs, quinolines

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8 An Approach to Improve Pre University Students' Responsible Environmental Behaviour through Science Writing Heuristic in Malaysia

Authors: Sheila Shamuganathan, Mageswary Karpudewan

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This study investigated the effectiveness of green chemistry integrated with Science Writing Heuristic (SWH) in enhancing matriculation students’ responsible environmental behaviour. For this purpose 207 matriculation students were randomly assigned into experimental (N=118) and control (N=89) group. For the experimental group the chemistry concepts were taught using the instructional approach of green chemistry integrated with Science Writing Heuristic (SWH) while for the control group the same content was taught using green chemistry. The data was analysed using ANCOVA and findings obtained from the quantitative analysis reveals that there is significant changes in responsible environmental behaviour (F 1,204) = 32.13 (ηp² = 0.14) which favours the experimental group. The responses of the qualitative data obtained from an interview with the experimental group also further strengthen and indicated a significant improvement in responsible environmental behaviour. The outcome of the study suggests that using green chemistry integrated with Science Writing Heuristic (SWH) could be an alternative approach to improve students’ responsible environmental behaviour towards the environment.

Keywords: Green Chemistry, Laboratory, science writing heuristic, pro environmental behaviour

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7 Naturally Occurring Chemicals in Biopesticides' Resistance Control through Molecular Topology

Authors: Riccardo Zanni, Maria Galvez-Llompart, Ramon Garcia-Domenech, Jorge Galvez

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Biopesticides, such as naturally occurring chemicals, pheromones, fungi, bacteria and insect predators are often a winning choice in crop protection because of their environmental friendly profile. They are considered to have lower toxicity than traditional pesticides. After almost a century of pesticides use, resistances to traditional insecticides are wide spread, while those to bioinsecticides have raised less attention, and resistance management is frequently neglected. This seems to be a crucial mistake since resistances have already occurred for many marketed biopesticides. With an eye to the future, we present here a selection of new natural occurring chemicals as potential bioinsecticides. The molecules were selected using a consolidated mathematical paradigm called molecular topology. Several QSAR equations were depicted and subsequently applied for the virtual screening of hundred thousands molecules of natural origin, which resulted in the selection of new potential bioinsecticides. The most innovative aspect of this work does not only reside in the importance of the identification of new molecules overcoming biopesticides’ resistances, but on the possibility to promote shared knowledge in the field of green chemistry through this unique in silico discipline named molecular topology.

Keywords: Green Chemistry, QSAR, biopesticide, molecular topology

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6 Preparation of MgO Nanoparticles by Green Methods

Authors: Maryam Sabbaghan, Pegah Sofalgar

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Over the past few decades, a significant amount of research activities in the chemical community has been directed towards green synthesis. This area of chemistry has received extensive attention because of environmentally benign processes as well as economically viable. In this article, the MgO nanoparticles were prepared by different methods in the present of ionic liquids. A wide range of Magnesium oxide particle sizes within the nanometer scale is obtained by these methods. The structure of these MgO particles was studied by using X-ray diffraction (XRD), Infrared spectroscopy (IR), and scanning electron microscopy (SEM). It was found that the formation of nanoparticle could involve the role of performed 'nucleus' and used template to control the growth rate of nucleuses. The crystallite size of the MgO products was in a range from 31 to 77 nm.

Keywords: Nanoparticles, Green Chemistry, MgO, ionic liquid

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5 Synthesis of 5-Substituted 1H-Tetrazoles in Deep Eutectic Solvent

Authors: Swapnil A. Padvi, Dipak S. Dalal

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The chemistry of tetrazoles has been grown tremendously in the past few years because tetrazoles are important and useful class of heterocyclic compounds which have a widespread application such as anticancer, antimicrobial, analgesics, antibacterial, antifungal, antihypertensive, and anti-allergic drugs in medicinal chemistry. Furthermore, tetrazoles have application in material sciences as explosives, rocket propellants, and in information recording systems. In addition to this, they have a wide range of application in coordination chemistry as a ligand. Deep eutectic solvents (DES) have emerged over the current decade as a novel class of green reaction media and applied in various fields of sciences because of their unique physical and chemical properties similar to the ionic liquids such as low vapor pressure, non-volatility, high thermal stability and recyclability. In addition, the reactants of DES are cheaply available, low-toxic, and biodegradable, which makes them predominantly required for large-scale applications effectively in industrial production. Herein we report the [2+3] cycloaddition reaction of organic nitriles with sodium azide affords the corresponding 5-substituted 1H-tetrazoles in six different types of choline chloride based deep eutectic solvents under mild reaction condition. Choline chloride: ZnCl2 (1:2) showed the best results for the synthesis of 5-substituted 1 H-tetrazoles. This method reduces the disadvantages such as: the use of toxic metals and expensive reagents, drastic reaction conditions and the presence of dangerous hydrazoic acid. The approach provides environment-friendly, short reaction times, good to excellent yields; safe process and simple workup make this method an attractive and useful contribution to present green organic synthesis of 5-substituted-1H-tetrazoles. All synthesized compounds were characterized by IR, 1H NMR, 13C NMR and Mass spectroscopy. DES can be recovered and reused three times with very little loss in activity.

Keywords: Green Chemistry, Click Chemistry, deep eutectic solvent, choline chloride, tetrazoles

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4 H₆P₂W₁₈O₆₂.14H₂O Catalyzed Synthesis of α-Aminophosphonates from Amino Acids Esters

Authors: Sarra Boughaba

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α-aminophosphonates have found a wide range of applications in organic and medicinal chemistry; they are considered as pharmacological agents, anti-inflammatory antitumor agents, and antibiotics. A number of procedures have been developed for their synthesis. However, many of these methods suffer from some disadvantages such as long reaction times, environmental pollution, utilization of organic solvents, and expensive catalysts. In the past few years, heteropolyacids have received great attention as environmentally benign catalysts for organic synthetic processes, they possess unique physicochemical properties, such as super-acidity, high thermal and chemical stability, ability to accept and release electrons and high proton mobility, and the possibility of varying their acidity and oxidizing potential. In this context, an efficient and eco-friendly protocol has been described for the synthesis of α-aminophosphonates via one pot, three component reaction catalyzed by H₆P₂W₁₈O₆₂.14H₂O as reusable catalyst, by condensation of amino acids esters, various aromatic aldehydes and triethylphosphite under solvent-free conditions, the corresponding α-aminophosphonates were formed in good yields as racemic or diastereomericmixture. All the new products were systematically characterized by IR, MS, and ¹H, ¹³C-³¹P-NMR analyses. This method offers advantages such as simplicity workup with the green aspects by avoiding expensive catalysts and toxic solvents, good yields, short reaction times.

Keywords: Green Chemistry, α-aminophosphonates, H₆P₂W₁₈O₆₂.14H₂O catalyst, amino acids esters

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3 Mitigating Biofouling on Reverse Osmosis Membranes: Applying Greener Preservatives to Biofilm Treatment

Authors: Anna Curtin, Matthew Thibodeau, Heather Buckley

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Water scarcity is characterized by a lack of access to clean and affordable drinking water, as well as water for hygienic and economic needs. The amount of people effected by water scarcity is expected to increase in the coming years due to climate change, population growth, and pollution, amongst other things. In response, scientists are pursuing cost effective drinking water treatment methods, often with a focus on alternative water sources. Desalination of seawater via reverse osmosis is one promising alternative method. Desalination of seawater via reverse osmosis, however, is limited significantly by biofouling of the filtration membrane. Biofouling is the buildup of microorganisms in a biofilm at the water-membrane interface. It clogs the membrane, decreasing the efficiency of filtration, consequently increasing operational and maintenance costs. Although effective, existing chemical treatment methods can damage the membrane, decreasing the lifespan of the membrane; create antibiotic resistance; and cause harm to humans and the environment if they pass through the membrane into the permeate. The current project focuses on applying safer preservatives used in home and personal care products to RO membranes to investigate the biofouling treatment efficacy. Currently, many of these safer preservatives have only been tested on cells in planktonic phase in suspension cultures, not on cells in biofilms. The results of suspension culture tests are not applicable to biofouling scenarios because organisms in planktonic phase in suspension cultures exhibit different morphological, chemical, and metabolic characteristics than those in a biofilm. Testing antifoulant efficacy of safer preservatives on biofilms will provide more applicable results to biofouling on RO membranes. To do this, biofilms will be grown on 96-well-plates and minimum inhibitory concentrations (MIC90) and log-reductions will be calculated for various safer preservatives. Results from these tests will be used to guide doses for tests of safer preservatives in a bench-scale RO system.

Keywords: Green Chemistry, Antimicrobial, Reverse osmosis, Biofouling, preservatives, safer alternative

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2 Green, Smooth and Easy Electrochemical Synthesis of N-Protected Indole Derivatives

Authors: Sarah Fahad Alajmi, Tamer Ezzat Youssef

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Here, we report a simple method for the direct conversion of 6-Nitro-1H-indole into N-substituted indoles via electrochemical dehydrogenative reaction with halogenated reagents under strongly basic conditions through N–R bond formation. The N-protected indoles have been prepared under moderate and scalable electrolytic conditions. The conduct of the reactions was performed in a simple divided cell under constant current without oxidizing reagents or transition-metal catalysts. The synthesized products have been characterized via UV/Vis spectrophotometry, 1H-NMR, and FTIR spectroscopy. A possible reaction mechanism is discussed based on the N-protective products. This methodology could be applied to the synthesis of various biologically active N-substituted indole derivatives.

Keywords: Green Chemistry, heteroaromatic, organic electrosynthesis

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1 Green Electrochemical Nitration of Bioactive Compounds: Biological Evaluation with Molecular Modelling

Authors: Sara Torabi, Sadegh Khazalpour, Mahdi Jamshidi

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Nitro aromatic compounds are valuable materials because of their applications in the preparation of chemical intermediates for the synthesis of dyes, plastics, perfumes, energetic materials, and pharmaceuticals. Chemical and electrochemical procedures are reported for nitration of aromatic compounds. Flavonoid derivatives are present in many vegetables and fruits and are constituent of many common pharmaceuticals and dietary supplements. Electrochemistry provides very versatile means for the electrosynthesis, mechanistic and kinetic studies. To the best of our knowledge, and despite the importance of these compounds in numerous scientific fields, there are no reports on the electrochemical nitration of Quercetin derivatives. Herein, we describe a green electrochemical synthesis of a nitro compound. In this work, electrochemical oxidation of Quercetin has been studied in the presence of nitrite ion as a nucleophile in acetate buffer solution (c = 0.2 M, pH = 6.0), by means of cyclic voltammetry and controlled-potential coulometry. The results indicate the participation of produced o-benzoquinones in Michael reaction with nitrite ion (in the divided cell) to form the corresponding nitro diol (EC mechanism). The purity of product and characterization was done using ¹H NMR, ¹³C NMR, FTIR spectroscopic techniques. The presented strategies use a water/ethanol mixture as solvent. Ethanol as cosolvent was also used in the previous studies because of its low cost, safety, easy availability, recyclability, bioproductability, and biodegradability. These strategies represent a one-pot and facile process for the synthesis of nitro compound in high yield and purity under green conditions.

Keywords: Green Chemistry, Molecular Docking, Cyclic Voltammetry, electrochemical synthesis

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