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  3. Synthesis of ethylene diamine tetraacetic acid and its impact on industrial wastewater treatment

Synthesis of ethylene diamine tetraacetic acid and its impact on industrial wastewater treatment

Number of pages: 63 File Format: word File Code: 31768
Year: 2014 University Degree: Master's degree Category: Biology - Environment
Tags/Keywords: cyanide - EDTA - Ethylenediaminetetraacetic acid - FTIR - icp - Industrial effluents - Monochloroacetic acid - synthesis - Synthesis of ethylenediamine - Wastewater treatment
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  • Summary of Synthesis of ethylene diamine tetraacetic acid and its impact on industrial wastewater treatment

    Academic thesis for receiving a master's degree in chemical engineering, environmental orientation

    Abstract:

    Ethylenediaminetetraacetic acid, due to its ability to solubilize and deactivate metal ions by forming a complex in the aqueous environment, has many applications, especially as a chelating agent. It has allocated iron fertilizer. The synthesis of this material is done in different ways. In this research, the synthesis of this material was done in three ways, and the possibility of converting the raffinite of the Sarcheshme copper complex into a chelated iron liquid fertilizer with EDTA was also investigated. In the first method, EDTA was produced from the reaction of ethylenediamine, monochloroacetic acid and sodium carbonate. In the second method, the alkaline cyanomethylation of ethylenediamine was performed in the presence of formaldehyde and sodium cyanide, and in the third method, the cyanomethylation and hydrolysis steps were performed in two separate steps. The efficiency of these three methods reached 60%, 80% and 91% respectively. Infrared spectroscopy (FTIR) data also confirmed the chemical analysis characteristics of the product. It should be noted that the first method has a low efficiency compared to the other two methods, but it does not have the risks of using cyanide. The second method, despite the good efficiency, is accompanied by numerous side reactions and this reduces the purity and quality of the product. In the third method, by performing the synthesis in two steps, a pure product is obtained, but it should be noted that cyanide can be very dangerous and deadly. To identify and measure the elements in raffinite, Inductively Coupled Plasma (ICP) analysis was performed. The concentration of all heavy elements except arsenic was below the permissible limit. Also, the infrared spectroscopy data confirmed the formation of the Fe-EDTA complex in the raffinite solution. rtl;">Introduction

    Ethylenediaminetetraacetic acid [1] (EDTA) or N, 'N- 1,2-Ethandilbis] N-(carboxymethyl) glycine [2][as a chelating agent [3] has the ability to form a stable and water-soluble complex with alkaline earth metals and heavy metals. This substance belongs to the family of amino polycarboxylic acids[4]. As a six-toothed ligand [5], it encloses the metal ion through four carboxyl groups and two amino groups and forms a stable structure [1]. Figure 1-1 shows the chemical structure of the EDTA molecule and Figure 1-2 shows the structure of the EDTA complex with a metal ion [2, 3].

    Manz [6] first introduced EDTA as a substitute for citric acid that was used in the textile and dyeing industries in an effort to reduce German foreign imports. He used ethylene diamine, monochloroacetic acid and sodium carbonate to synthesize EDTA and registered this method in his name, but this method has a low yield. In the following years, other methods based on the use of ethylene diamine, formaldehyde, cyanide salts and hydrogen cyanide were introduced, which have high efficiency and purity for the synthesis of EDTA [4]. In the following chapters, various methods of EDTA synthesis will be discussed in detail.

    EDTA is used for many purposes due to its ability to solubilize and deactivate metal ions by forming a complex in aqueous medium. For example, in the field of fertilization, nutrients used by plants, such as iron, zinc, manganese and copper, are added to chemical fertilizers in a chelated form with EDTA salts to prevent precipitation with anions in the soil. The conversion of these metal ions from the cationic form to the anionic form increases their mobility in the soil and increases their absorption by plants [1, 5]. It is very important. However, this material is not produced in Iran. Therefore, Iran is an importer of this material. In this project, the aim is to investigate and compare different methods of EDTA synthesis, to know the advantages and disadvantages of these methods and to achieve its domestic production.Although achieving this goal due to the toxicity of the raw materials requires advanced and accurate equipment and taking into account various conditions and factors from an industrial point of view, nevertheless, the laboratory investigation of this project can be of great help in understanding the issue and the production of this valuable material. This solution is rich in iron and poor in copper. Converting this wastewater into liquid fertilizer containing iron with the help of EDTA and reusing it in the field of agriculture can be important from an environmental and economic point of view. The first chapter includes introductions to the chosen topic, research objectives and outlines. The second chapter includes the theoretical basics of research, including the introduction of EDTA, the methods of EDTA synthesis, its applications, and so on. is The third chapter includes a review of past works in the field of methods used for EDTA synthesis. The fourth chapter includes the description of the methods used for the synthesis of EDTA in this thesis, the production of liquid fertilizer and the equipment used. In the fifth chapter, the results and analysis of the spectra obtained and finally in the sixth chapter, the conclusions and suggestions are given. rtl;"> 

    2-1-Introduction

    In this chapter, the physical and chemical properties of EDTA, its applications, and the methods of synthesis of this substance are presented first. In the following, plant nutrients, chemical fertilizers and the reason for the importance of chelating agents in them are briefly discussed. Considering that one of the goals of this project is to investigate the possibility of converting the raffinite returned to the heap of Sarchesmeh copper complex into liquid fertilizer, the description of how to produce this liquid during the process of hydrometallurgy [9] copper extraction [10] is discussed. Finally, the methods of product investigation and analysis are presented.

    2-2-Introduction of physical and chemical properties of EDTA

    EDTA is a crystalline solid, white in color, odorless and tasteless. This substance is insoluble in water, alcohols and organic solvents and in mineral acids and alkaline solutions such as sodium hydroxide, sodium carbonate and ammonia. EDTA can exist in the form of alkali metal salts, the most important of which are disodium and tetrasodium EDTA salts. These salts have the ability to dissolve in water]6.\

    Abstract:

    Ethylene diamine tetraacetic acid (EDTA), with the ability of solubilizing as well as inactivating the metal ions through complex formation, has several applications especially in the field of Fe-chelate fertilizers. There are various ways to synthesize EDTA. In this study, EDTA was synthesized using three methods and the possibility of conversion of raffinate solution of Sarchshmeh copper complex to the iron-chelate fertilizer by EDTA was also studied. In the first method, EDTA was synthesized from ethylenediamine, monochloroacetic acid and caustic soda. The second method was based on the alkaline cyanomethylation of ethylene diamine in the presence of cyanide ions and formaldehyde. In the third method, the cyanomethylation and hydrolysis were carried out in two separate steps. The yields of the first, second and third methods were 60%, 80% and 91%, respectively. Fourier Transform Infrared spectroscopy (FTIR) data confirmed the chemical analysis characteristics of the products. It should be mentioned that the first method offers low yield. However, it does not have the dangers of using cyanide. Regarding the second method, although its yield is high enough, the quality and purity of the product is affected by the numerous side reactions. The third method, with the two separate stages, results in a pure form of EDTA. However, it should be noted that the cyanide is very deadly and hazardous. The Inductively Coupled Plasma (ICP) analysis was done for detection and determination of the elements in the raffinate.

  • Contents & References of Synthesis of ethylene diamine tetraacetic acid and its impact on industrial wastewater treatment

    List:

    Chapter One: Introduction. 1

    1-1-Introduction 2

    1-2- The purpose of the research 3

    1-3-Outlines 4

    Chapter Two: Theoretical foundations of the research. 5

    2-1-Introduction 5

    2-2- Introduction of physical and chemical properties of EDTA 6

    2-2-1 Introduction of physical properties of EDTA. 6

    2-2-2-Introducing the chemical properties of EDTA. 7

    2-3-Uses of EDTA 11

    2-4- Introduction of EDTA synthesis methods 15

    2-4-1- Synthesis of EDTA with ethylene diamine, monochloroacetic acid and sodium carbonate. 15

    2-4-2-one-step synthesis of EDTA with ethylenediamine, formaldehyde and sodium cyanide. 15

    2-4-3- two-step synthesis of EDTA with ethylenediamine, formaldehyde and hydrogen cyanide. 16

    2-4-4- preparation of EDTA salts. 17

    2-5 - Elements needed in plant nutrition 17

    2-5-1- The role of iron in plants and its deficiency symptoms. 17

    2-5-2- Causes of iron deficiency. 18

    2-5-3- Eliminate iron deficiency in plants. 19

    2-5-4- The role of synthetic iron chelates as iron carriers in plants. 19

    2-6-General copper production methods 21

    2-6-1-Hydrometallurgy. 21

    2-6-2-1-Copper solvent extraction steps in the hydrometallurgy process. 21

    2-6-2-2-Leaching stage. 22

    2-6-2-3-step of solvent extraction. 23

    2-7- Methods of investigation and analysis of raw materials and products 23

    2-7-1-Infrared Spectroscopy (FTIR) 23

    2-7-2-Inductively Coupled Plasma (ICP) 24

    Chapter 3: Review of previous works. 25

    Chapter Four: Materials, necessary equipment and work methods. 30

    4-1-EDTA synthesis 31

    4-1-1-materials necessary for EDTA synthesis. 31

    4-1-2- Necessary equipment for EDTA synthesis. 31

    4-1-3- working procedure for EDTA synthesis. 31

    4-1-3-1-synthesis of EDTA from monochloroacetic acid pathway. 31

    4-1-3-2-EDTA synthesis using sodium cyanide in one step. 33

    4-1-3-3-EDTA synthesis using sodium cyanide in two steps. 36

    4-2- Formation of metal complex with EDTA 38

    4-2-1- Chemicals used. 38

    4-2-2- Equipment used. 38

    4-2-3- Working method 38

    4-2-3-1-Preparation of disodium EDTA salt. 38

    4-2-3-2- preparation of liquid iron fertilizer from raffinite. 39

    Chapter five: discussion and results. 40

    5-1- Interpretation of the results of the device analysis obtained from the synthesized EDTA 41

    5-1-1- Interpretation of the FTIR spectrum of EDTA synthesized from the monochloroacetic acid route. 41

    5-1-2- Interpretation of FTIR spectrum of EDTA synthesized from one-step route (stoichiometric values ??for formaldehyde and sodium cyanide) 42

    5-1-3- Interpretation of FTIR spectrum of EDTA synthesized from one-step route (additional values ??for formaldehyde and sodium cyanide) 43

    5-1-4- Interpretation of FTIR spectrum Related to EDTA synthesized from a two-step route. 44

    5-2-Efficiency calculation 45

    5-2-1-Efficiency calculation for EDTA synthesized from monochloroacetic acid route. 45

    5-2-2- Calculation of yield for EDTA synthesized from one-step route. 46

    5-2-3- Calculation of yield for EDTA synthesized from two-step route. 47

    5-3- Interpretation of ICP analysis result related to raffinite solution 47

    5-4- Interpretation of FTIR spectrum results related to the formation of metal complex with EDTA in raffinite solution 50

    Sixth chapter: conclusion and future perspective. 53

    References. 56

     

    Source:

    [1] J. Roger Hart, W. Gerhartz, F. Ullmann, "Ethylenediaminetetraacetic Acid and Related Chelating Agents" in Ullmann's Encyclopedia of Industrial Chemistry, Vol 12, Fifth Edition, Massachusetts, Wiley-VCH, 585-591, (1987).

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    [3] S. A. Abo Farha, N.A. Badawy, A.A. El-Bayaa, and S.E. Garamon, "The Effect of Chelating Agent on the Separation of Some Metal Ions from Binary Mixture Solution by Cation-Exchange Resin", Nature and Science, 8(10),16-25, (2010).

    [4] R. L. Myers, "The 100 Most Important Chemical Compounds: A Reference Guide", London, Greenwood Press, 124-126, (2007).

    [5] V. Gowariker, V. N. Krishnamurthy, S. Gowariker, M. Dhanorkar, K. Paranjape, "The Fertilizer Encyclopedia", New Jersey, John Weily & Sons, 137-138,. Paranjape, "The Fertilizer Encyclopedia", New Jersey, John Weily & Sons, 137-138, (2009).

    [6] K. L. Cheng, K. Ueno, T. Imamura, "Handbook of Organic Analytical Reagents", Second Edition, Florida, CRC Press, 259-263, (1992).

    [7] J. Kenkel, "Analytical Chemistry for Technicians", Third Edition, Florida, CRC Press, 120-122, (1988) Springer Science, 327-329, (2005) Pulping Chemistry, Japan TAPPI, (1999).

    [12] T. E. Furia, "Handbook of Food Additives", Second Edition, Florida, CRC Press, 271-294. (1977)

    [15] S. M. Khopkar, "Basic Concepts Of Analytical Chemistry", New Dehli, New Age International (P) Limited, 75-77, (1988).

    [16] F. C. Bersworth, N. Verona, "Aliphatic Polycarboxylic Amino Acids & Process of Making Same", US Patent Office, (1946).

    [17] J. H. Nashua, J. T. Miford, C. Johnson, "Method for the Manufacture of the Disodium Salt of Ethylene Diamine Tetraacetic Acid", Us Patent Office (1971).

    [18] S. Tisdale, and Nelson, Fertilizers and Soil Fertility, translated by Jafar Malkouti, Abdul Hossein Raazi Hamdani, Tehran, University Publishing Center, (1370).

    [19] W. D. C. Schenkeveld, E. J. M. Temminghoff, "The Effectiveness of Fe Chelates in Mending and Preventing Iron Chlorosis in Soil Grown Soybean Plants", in: Hany. E. S., Edited. Soybean Physiology and Biochemistry, 83-108, (2011).

    [20] S. Cesco, M. Nikolic, V. Romheld, Z. Varanini, R. Pinton, "Uptake of Fe from Soluble Fe-Humate Complexes by Cucumber and Barley Plants", Journal of. Plants and Soil, 241, 121-128, (2002).

    [21] A. Alvarez-Fernandez, P. Garcia-Lavina, C. Fidalgo, J. Abadia, A. Abadia, "Foliar Fertilization To Control Iron Chlorosis In Pear (Pyrus Communis L.) Trees", Journal of. Plants and Soil, 263, 5-15, (2004).

    [22] R. Fernandez-Escobar, D. Barranco, M. Benlloch, "Overcoming Iron Chlorosis In Olive And Peach Trees Using A Low-Pressure Trunk-Injection Method", Journal Of Hortscience, 28(3), 192-194, (1993). Y. Chen, Ph. Barak, "Iron Nutrition of Plants in Calcareous Soils", the Netherlands, Kluwer Academic Publishers, 35, 217-238 (1982).

    [24] L. L. Barton, G. Abadia, "Iron Nutrition in Plants and Rhizospheric Microorganisms", the Netherlands, Springer, 103-107, (2006).

    [25] T. g. Biswas, V.J. Davenport, copper extraction techniques, translated by Hossein Faraji, Tehran, University Publishing Center, (2007).

    [26] R. S. Forgan, "Mct_Redbook: Solvent Extraction Reagents and Applications", USA, Cognis Corporation, (2007). D. Field, S. Sternahl, J. Ar. Kalman, "The Application of Spectroscopy in Organic Chemistry", translated by Issa Yavari, Tehran, University Science Publishing, (1385).

    [28] A. Montase, "Inductively Coupled Plasma Mass Spectrometry", Canada, Wiley-VCH, (1998).

    [29] F. Munz, "Polyamino Carboxylic Acids & Process of Making Same", US Patent Office, (1938).

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