Word Files
Reference for Downloading Educational Files
  2. Chemical - Petrochemical Engineering
  3. Utilization of new catalysts in the one-step synthesis of Novonagel

Utilization of new catalysts in the one-step synthesis of Novonagel

Number of pages: 108 File Format: word File Code: 31869
Year: 2013 University Degree: Master's degree Category: Chemical - Petrochemical Engineering
Tags/Keywords: Catalyst - Condensation reaction - destructibility - Green chemistry - Navonagle - One-step synthesis
  • Part of the Content
  • Contents & Resources

  • Summary of Utilization of new catalysts in the one-step synthesis of Novonagel

    Dissertation for receiving a master's degree (M.Sc)

    Trend: Organic Chemistry

    Abstract

    The formation of carbon-carbon bond is very important in organic chemistry. One of the reactions that lead to the formation of this bond is the Novnagel condensation reaction. The products of this reaction have wide applications, including in the pharmaceutical, paint, polymer and other industries. . . are.

    In this research, it has been tried to optimize the conditions for the Novnagel reaction in such a way that it matches the environmental considerations and the principles of green chemistry as much as possible. After optimizing the temperature and the amount of the catalyst and investigating the effect of the solvent, it was found that the best reaction conditions are obtained at 90°C, in the conditions without solvent and in the presence of Elserine amino acid as a catalyst. Finally, to prove the formation of products from different derivatives, HNMR, FT-IR and melting point tests were used.

    Introduction

    Development means planning for the society to reach from the current situation to a more favorable one, and sustainable development[1] means that it should be planned in such a way that future generations do not have problems in meeting their needs, national capitals do not fall in value and Don't harm the environment either.

    Green chemistry aims to achieve sustainable development at the level of human societies.

    Green chemistry guides chemists in the direction of expanding processes and products without pollution and risk. The synthesis of a chemical product requires a safe method and a suitable strategy in terms of production, consumption and health costs.

    Environmental pollution and the contribution of chemical reactions and chemists in this problem have caused scientists to seek to design methods that are as pollution-free as possible. Green chemistry deals with the classification and definition of principles to achieve this lofty goal.

    Green chemistry is a term that was first proposed by Paul Anastas. The brief definition of green chemistry is as follows: Innovation, design and application of chemical products and processes to reduce or eliminate the use and production of hazardous substances. [[i]]

    Green chemistry is a chemical philosophy that encourages the design of products and processes that reduce or eliminate the use or production of hazardous substances. and aims to prevent or reduce the pollution of resources.

    1.1 Principles of Green Chemistry

    Anastas and Warner set up a series of principles, which are known as the twelve principles of green chemistry, which clearly show the purpose of green chemistry. [[ii]] These principles are:

    Principle 1: Prevention

    Principle 2: Atomic saving

    Principle 3: Reducing the use of dangerous chemicals

    Principle 4: Design for safer chemicals

    Principle 5: Safer solvents and auxiliaries

    Principle 6: Design for energy efficiency

    Principle 7: Use of renewable reserves

    Principle 8: Reduction of derivatives

    Principle 9: Catalysts

    Principle 10: Design for destructibility

    Principle 11: Real-time analysis for pollution prevention

    Principle 12: Safer chemistry to prevent accidents

    Next, we will explain each of these principles

    1.1.1 Prevention

    Chemical reactions should be designed in such a way as to prevent the production of waste materials as much as possible. Decontamination of the environment is much more difficult and expensive than its prevention

    The consequences of ocean water pollution and ozone layer depletion will reach the whole world, for this reason, scientists in every field of science are always at the forefront of solving problems, and from a scientific point of view, prevention is always easier and less expensive than treatment.

    If a healthy, low-risk, safe method or reagent with less toxicity can be used to perform a reaction, scientific ethics dictates that a researcher must do this.

    For example, if there are no specific factors to perform the reaction, using low-risk, cheap, available materials is always preferable. The following order, as an example, indicates that it is better to use reagents that have less metal in their structure and produce less non-toxic byproducts:

    H2O2 > KMnO4> OsO4

    1.1.2 Atomic economy

    Synthetic methods should be designed in such a way that the atoms in the raw materials are used have the most participation in the reaction, in the final product. Therefore, if in a synthetic mechanism, the reaction efficiency is 100%, but the side product is also produced during the reaction, and some of the atoms of the reactants are not used in the product, such a reaction will not be desirable, but the state where all the primary atoms are present in the final product will be more desirable.

    Pericyclic reactions have the maximum atom saving because they do not introduce any atoms into the environment, this group of reactions are performed with 100% atom saving.

    Claisen rearrangement and Diels-Alder reaction are given below as examples of 100% atom saving reactions.

    1.1.3       Reducing the use of hazardous chemicals

    Synthetic methods should be designed so that the substances used and produced have less toxicity for human health and the environment or do not have any toxicity

    This principle promotes the use of reagents, intermediates, and the production of byproducts with less toxicity.

    Using reserves with less toxicity requires the development of renewable raw materials

    1.1.4 Designing for safer chemicals

    Chemical products should be designed to be less toxic while performing better and more effectively. Therefore, when the chemical industry makes a decision about the development and supply of a product, it should consider the environmental characteristics (reduction of toxicity, carcinogenicity, etc.) standard and check the common characteristics (vapor pressure, color, stability, etc.), in such a way that its transportation is low-risk and safe, its weighing is convenient and does not have explosive properties. It is safer to use water, alcohols, supercritical carbon dioxide or biodegradable surfactant solutions. These solvents are preferable to chlorinated solvents. Methodology [2] has a special place in the synthesis of organic substances because scientists in this field of research in chemistry reproduce and reproduce the required products by inventing and applying new, low-cost and safer conditions, so that if possible, old methods are not used. Therefore, the scientists and researchers of Roshiab [3] always seek to discover new methods that are safer, less expensive and more convenient. As much as possible, synthetic processes should be carried out at ambient pressure and temperature. Especially in the petrochemical and chemical production industries, when the temperature increases to carry out a chemical process, the cost of cooling systems also increases accordingly. In addition, to increase the temperature and heat, more energy and fuel are needed, which is also costly.

    Therefore, designing reactions with lower activation energy becomes necessary.

  • Contents & References of Utilization of new catalysts in the one-step synthesis of Novonagel

    List:

    1 Green Chemistry 1

    1.1 Principles of Green Chemistry 3

    1.1.1 Prevention 3

    1.1.2 Atom Saving 4

    1.1.3 Reducing the Use of Hazardous Chemicals 5

    1.1.4 Designing for Safer Chemicals 5

    1.1.5 Safer solvents and auxiliaries 5

    1.1.6 Design for energy efficiency 6

    1.1.7 Use of renewable resources 6

    1.1.8 Reduction of derivatives 7

    1.1.9 Catalysts 7

    1.1.10 Design for degradation Adaptability 9 1.1.11 Real-time analysis for pollution prevention 9 1.1.12 Safer chemistry for accident prevention 9 1.2 Efforts and achievements of green chemistry 10 1.2.1 Alternative fuels 10 1.2.2 Green and biodegradable plastics 11

    1.2.3 Redesign of chemical reactions 13

    1.2.4 Biological polystructures 13

    2 Novnagel reaction 15

    2.1 Conditions for carrying out the reaction 18

    2.2 Applications of Novnagel reaction 18

    2.3 Synthesis of disordered ring compounds 18

    3 Catalyst 26

    3.1 Types of catalysts 27

    3.1.1 Homogeneous catalyst 27

    3.1.2 Heterogeneous catalyst 28

    3.1.3 Biological catalysts 28

    3.2 Catalysts used for Novenagel reaction 28

    3.2.1 Amines and ammonium salts 28

    3.2.2 Lewis acids 29

    3.2.2.1 Titanium tetrachloride 29

    3.2.2.2 Cadmium iodide 29

    3.2.2.3 Zinc chloride 30

    3.2.3 Mineral solids and solid surfaces 30

    3.2.4 Alkali metal salts 30

    3.2.5 Phosphate catalysts 31

    3.2.5.1 Optimized natural phosphate 31

    3.2.5.2 Using phosphate complexes with Solid substrate 31

    3.2.5.3 AlPO4-Al2O3 catalyst 33

    3.2.5.4 Diammonium hydrogen phosphate 33

    3.2.6 Ionic liquids 35

    3.3 Carrying out the Novo Nagel reaction using microwave radiation 36

    4 Amino acid 37

    4.1 Importance and medical application of amino acids: 40

    4.2 Classification of amino acids 41

    4.2.1 Standard amino acids 42

    4.2.2 Rare protein amino acids 42

    4.2.3 Non-protein amino acids 43

    4.3 Classification of amino acids according to nutritional role 43

    4.3.1 Essential amino acids 43

    4.3.2 Non-essential amino acids 43

    4.4 Classification of amino acids according to chemical structure 44

    5 Experimental section 48

    5.1 Specifications of devices 49

    5.2 Chemicals 49

    5.3 Optimization of reaction temperature 50

    5.4 Optimization of catalyst amount 50

    5.5 Effect of solvent 51

    5.6 General method of synthesis of unsaturated derivatives 52

    5.7 Melting point measurement using capillary tube 53

    5.8 Synthesis of derivatives 54 5.8.1 Synthesis of ethyl 3-(4-chlorophenyl)-2-cyanoprop-2-enoate derivative 54 5.8.1.1 Nuclear magnetic resonance test results 54 5.8.1.2 FT-IR test results 56 5.8.2 Synthesis Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoate derivative 57 5.8.2.1 Nuclear magnetic resonance test results 57 5.8.2.2 FT-IR test results 61 5.8.3 Synthesis of ethyl 3-(2-methoxy phenyl)-2-cyanoprop-2-enoate derivative 62 5.8.3.1 Nuclear magnetic resonance test results 62

    5.8.4.2 FT-IR test results 71

    5.8.5 Synthesis of ethyl 3-(4-hydroxyphenyl)-2-cyanoprop-2-enoate derivative 72

    5.8.5.1 Nuclear magnetic resonance test results 72

    5.8.5.2 Review of FT-IR test results 76

    5.8.6 Synthesis of ethyl 3-(2-bromophenyl)-2-cyanoprop-2-enoate derivative 77

    5.8.6.1 Nuclear magnetic resonance test results 77

    5.8.6.2 Review of FT-IR test results 81

    5.8.7 Synthesis of (4-fluorobenzylidene)malononitrile derivative 82

    5.8.7.1 Nuclear magnetic resonance test results 82

    5.8.7.2 FT-IR test results 85

    5.8.8 Derivative synthesis8 Synthesis of (4-chlorobenzylidene) malononitrile derivative 86 5.8.8.1 Nuclear magnetic resonance test results 86 5.8.8.2 FT-IR test results 89 5.8.9 Synthesis of (4-bromobenzylidene) malononitrile derivative 90 5.8.9.1 Nuclear magnetic resonance test results 90 5.8.9.2 FT-IR test results 93 5.8.10 Synthesis of (4-methoxybenzylidene)malononitrile derivative 94 5.8.10.2 FT-IR test results 97 5.8.11 Synthesis of ethyl 3-(4-N,N-dimethylamino phenyl)-2-cyanoprop-2-enoate derivative 98 5.8.11.1 Nuclear magnetic resonance test results 98 5.8.11.2 FT-IR test results 102

    6 references 104

     

    Source:

    2001), 1108, 8.

    [[1]] Kim Y.H. etal, Bioconjugate Chem,(2001), 932, 12.

    [[1]]   Merrill L. etal, ChemMatters,(2003), 7,4.

    [[1]] Anastas P.T. Warner J.C., Green Chemistry: Theory and Practice, New York, Oxford University Press, (1998). Spangler F.W., Org Synth.(1955), 377,3.

    [[1]] Rand L. Swisher J.V. Cronin C.J., J. Org Chem.(1962), 3505,27.

    [[1]] Acher D.S. Hertler W.R., J. Am. Chem.Soc.(1962), 3370,84.

    [[1]]   Cardillo G. etal., Synth. Commun. (2003), 1578,33.

    [[1]] Tietze L.F. Beifuss U., In comprehensive organic synthesis, Vol. 2, Oxford, pergamon press, (1991).

    [[1]] Bigi F. etal, J. Org. Chem.,(1999), 1033,64.

    [[1]] Yu N. Aramini J.M. Germann M.W., Tetrahedron Lett.(2000), 6993,41.

    [[1]] Bigi F. etal, Green Chemistry,(2000), 3,2.

    [[1]] Tarlton E.J. Mc Donald S.F. Baltazzi E., J. Am. Chem. Soc.,(1960), 4389,82.

    [[1]] Kwak G. Fujiki M., Macromolecules,(2004), 2021,37.

    [[1]] Wright M.E. Mullick S., Macromolecules, (1992), 6045, 25.

    [[1]] Ryabukin S.V. et al., J. Comb. Chem.(2007), 1073,9.

    [[1]] Pizzirani D. Roberto M. Recantini M., Tetrahedron letters. (2007), 7120,48.

    [[1]] Alonso S.J. etal, Tetrahedron,(2007), 7120,63.

    [[1]] Barnes D.M.etal, Tetrahedron,(2006), 11311,62.

    [[1]] Karan J.J. Manian R.D.R.S. Raghunathan R., Tetrahedron letters,(2006), 2265,7.

    [[1]] Bhowmik P.K. Nedeltchev A.K. Han H., Tetrahedron letters,(2007), 5383,48.

    [[1]] Che M. Masure D.Chaquin P., j.Phys.Chem., (1993), 2022,97.

    [[1]] Knoevenagel E., Chem. Ber., (1896), 172,29.

    [[1]] Lehrent W., Synthesis, (1974), 667,1974.

    [[1]] Courtheyn D. Verhe R. DeKimpe N. deBuyck L. Schamp N., J.Org. Chem., (1981), 3236,46.

    [[1]] Prajapati D. Sandhu J.S., J. Chem. Soc. Perkin Trans. I,(1993),739.

    [[1]] Rao P.S. Venkataratnam R.V., Tetrahedron Lett.,(1991), 5821,32.

    [[1]] Moison H. Texier-Boullet F. Foucud A., Tetrahedron,(1987), 537,43.

    [[1]] CabelloJ.A. Campello J.M. Garcia A. Luna D. Marinas J.M., J. Org. Chem., (1984), 5195.49. SuzukiH., Tetrahedron Lett. (2003), 399,44.

    [[1]] Rand L. Haidukewych D. Dolinski R.J., J. Org. Chem., (1966), 1272.31. et al., Synth. Commun.,(1999), 1057,29.

    [[1]] Alahiane A. etal, Appl. Catal. A,(2001), 217,206.

    [[1]] Fraile J.M. etal, Green Chem., (2001), 271,3. J. Boukhari A. Holt E.M., Solid State Sci.,(1999), 373,1.

    [[1]] El-maadi A

Utilization of new catalysts in the one-step synthesis of Novonagel
How To Access The File
Related Contents:
Number of pages: 109 Category: Chemical - Petrochemical Engineering

Master's Thesis, Department of Chemistry, Organic Chemistry, Abstract An effective method for the synthesis of pyrido[3,2-d]pyrimidine derivatives from the three-component condensation of 6-aminouracil, 6-amino2-thiouracil or 6-amino-1,3-dimethyluracil with aryl aldehydes and malononitrile, a class of pyrido[3,2-d]pyrimidine derivatives in the presence of high performance basic ...

Number of pages: 137 Category: Chemical - Petrochemical Engineering

Dissertation for obtaining a master's degree M. Sc)) Department of Chemistry - Green Synthesis of Organic Chemistry 2-phenylimidazoles boiled using ionic liquid. Imidazoles are an important group of heterocyclic compounds that have various biological and medicinal activities such as anti-hypertensive, anti-cancer, anti-HIV, anti-bacterial and pain reliever. In this thesis, new ...

Number of pages: 116 Category: Chemical - Petrochemical Engineering

Dissertation to receive M.Sc. Field of organic chemistry abstract green synthesis of 2-phenyl oxazoles boiled using ionic liquid Oxazoles are an important group of heterocyclic compounds. They are the structural subunits of various natural active products and are valuable synthetic and pharmaceutical precursors. Oxazoles have antibacterial, antifungal, anti-inflammatory and ...

Number of pages: 91 Category: Chemical - Petrochemical Engineering

Dissertation for Master's Degree in Organic Chemistry Abstract: The new works carried out in this thesis include the condensation reaction of arylglyoxals prepared during the oxidation of acetophenones related to selenium dioxide with 1,2-diaminobenzene, 2,3-diaminomalonitrile, 2,3-diaminopyridine and 4-nitro-1,2-diaminobenzene in order to prepare quinoxalines and the ...

Number of pages: 86 Category: Chemical - Petrochemical Engineering

Master's Thesis in the field of Chemical Engineering Abstract Investigation of parameters affecting the production of alumina gel by sol-gel method Sol-gel method is one of the common methods that is widely used to produce different nanoparticles. In this method, a solution of initiators is mixed with water in the presence of a catalyst, and hydrolysis and polymerization ...

Number of pages: 103 Category: Chemical - Petrochemical Engineering

The thesis for obtaining a master's degree in the field of organic chemistry, abstract protection and deprotection of functional groups is one of the inevitable steps in the synthesis of multi-functional compounds. Selective protection of carbonyl groups is very important in modern organic chemistry. 1-Diacetates are one of the basic protective groups of the carbonyl functional ...

Number of pages: 93 Category: Chemical - Petrochemical Engineering

Dissertation for Master's degree (M.Sc.) Title abstract: One-step synthesis of new thiazole and bisthiazole derivatives with various connections. In this research, the synthesis of new thiazole derivatives and bisthiazoles with different connections was investigated by click chemistry and green chemistry methods. First, the synthesis of bisacetophenones (b3-a3) through

Number of pages: 121 Category: Chemical - Petrochemical Engineering

Master's thesis in the field of chemical nanoengineering Abstract The synthesis of silicon dioxide nanoparticles from silicon oil waste using the synthesis method of silicon dioxide nanoparticles [1] has many industrial applications. The industrial use of these particles in traditional fields as well as new fields is expanding, for which new applications are continuously found. ...

Number of pages: 80 Category: Chemical - Petrochemical Engineering

Dissertation for Master's Degree in Organic Chemistry. Summary of the research done in this thesis consists of two parts, the first part is the synthesis of the precursor of 4,5-dihydropyrrolo[1,2,3-hi]indole-1,2-dione (compound 1) and one-pot, three-component synthesis of new derivatives of spiro terecates in water-green solvent and in the presence of HMTA catalyst. The second ...

Number of pages: 103 Category: Chemical - Petrochemical Engineering

Dissertation for Master's Degree in Organic Chemistry Abstract of the research done in this thesis consists of two parts, the first part includes the one-pot synthesis of new spiro compounds using 4,5,5-trimethyl 4,5-dihydropyrrolo{1,2,3-hi}indole 1,2-dione with aromatic amines and vectors. The second part includes the synthesis of new derivatives of spiro compounds using ...