DOCSLIB.ORG

Annals of West University of Timisoara

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Annals of West University of Timisoara Annals of West University of Timisoara Series of Chemistry 22 (2) (2013) 57-66 THE SYNTHESIS OF SALICYLALDEHYDE VARYING DIFFERENT PARAMETERS Roxana Crişan, Dorina Modra West University of Timişoara, Faculty of Chemistry, Biology, Geography, Department of Biology-Chemistry, Pestalozzi Street, 16, Timişoara, 300115, Romania Received: 21 October 2013 Modified: 30 October 2013 Accepted: 8 November 2013 SUMMARY We tried to find the optimum conditions for salicylaldehyde synthesis. The influence of ratio of reactants, the solvent used, the time of synthesis, reaction temperature, steam entrainment method of the product from the reaction mixture were studied. Crude salicylaldehyde is processed, and purified by distillation, and then is physico-chemical characterized. Keywords: salicylaldehyde, 2-hydroxybenzaldehyde, ortho-hydroxybenzaldehyde INTRODUCTION Salicylaldehyde is called 2-hydroxybenzaldehyde and ortho-hydroxybenzaldehyde and is an organic compound with the formula C7H6O2. Part of the class hydroxy aromatic aldehydes, aromatic nucleus contains two functional groups: a hydroxyl and aldehyde one. This colorless liquid has a bitter almond odor at higher concentrations The natural oils found in Spiraea [Filipendula (Spiraea) ulmaria (Rosaceae)]. Sweet-smelling flowers containing salicylaldehyde and methyl salicylate, glycosides form. Was also identified as a component of the characteristic flavor of buckwheat. [1] Salicilaldehyde is used as an important intermediate in the chemical industry, in medicine. It is used in perfume, fragrances, dyes, pharmaceuticals, etc.[2] Salicylaldehyde and its derivatives can be used as preservatives in cosmetic products, [3] fragrances, essential oils in various biological applications. [4] antibacterial Her work is powerful enough to allow its use in very low concentrations. Also get in formulation of perfumes and fragrances. 57 C RIŞ AN R., M ODRA D. Salicylic aldehyde is an important intermediate in the manufacture of herbicides and pesticides. [5] Also, salicylaldehyde and its derivatives are used for various reactions for the production of polymers and fibers. Largest quantity is used in the manufacture of coumarin. Coumarin is a chemical used in soaps, flavors, fragrances and extensively in electroplating, as a leveling agent. [6] Salicylaldehyde and its derivatives are used in electroplating formulations. [6] Salicylic aldehyde is a precursor to aspirin [7]. Compounds derived from salicylaldehyde are also used in large quantities in various applications. Thus, salicylaldoxime branched alkyl chain are used as extraction agent in the separation and concentration operations in copper recovery. [8-10] Schiff bases may be used in the formation of ligands that are used as polymerization catalysts in a variety of industrial applications. Salicylaldehyde is an essential precursor for a variety of chelating agents, some of which are very important Transition metal complexes with Schiff ligand were very much studied in recent years because they are widely applied in many fields: biochemistry, analytical, etc. The ligands and metal complexes of Co(II), Ni(II), Cu(II), Zn(II) Cd(II), shows the antibacterial and antifungal activities. [11, 12] Salicylaldehyde with other aliphatic aldehydes (2-methylbutyraldehyde, hexanal, 3-metilbutraldehida, etc.) are used as additives in the cigarette. The main processes for manufacturing hydroxybenzaldehyde is based on the use of phenol as a raw material. One method consists in preparing the salicylaldehyde phenol and chloroform by heating with sodium hydroxide or potassium hydroxide in a Reimer-Tiemann reaction. In most cases, the yield of aldehyde is low and the reaction has the disadvantage that it uses excess chloroform and is expensive to recover and recycling it. [13] When the reaction is carried out in mixtures of organic solvents, salicylaldehyde is obtained in higher yields and, in addition, the amount of p-hydroxybenzaldehyde as an undesired product is drastically reduced. There are many methods for the synthesis of salicylaldehyde. [14] The current research and development trends in the synthesis of salicylaldehyde include formylation reactions of phenol in the presence of Sn ions, Mg, Li, etc. [15-17] Salicylaldehyde was synthesized by the reaction between formaldehyde and phenol in the presence of a complex of magnesium methoxide in an anhydrous medium. [6] An alternative method of synthesis involves the condensation of phenol with formaldehyde yielding hydroxybenzyl alcohol, which is oxidized to salicylaldehyde. [18, 19] Salicylaldehyde was obtained by electrolytic reduction of salicylic acid. 58 THE SYNTHESIS OF SALICYLALDEHYDE VARYING DIFFERENT PARAMETERS Salicylaldehyde was obtained with a purity of 96%, with a yield of 74%. [20] Must be found new efficient catalysts to improve the yield in salicilaldehyde, to obtain simple and efficient method for separating of products, to reduce costs. In this study, we synthesized salicylaldehyde from phenol and chloroform in the presence of sodium hydroxide and a mixture of solvents to determine the optimal conditions according to the variation of reaction parameters, conditions that lead to higher yields. MATERIALS AND METHODS For the synthesis, reagents that we used were: phenol (99%) (Sigma-Aldrich), chloroform (99%) (Sigma-Aldrich), sodium hydroxide (99.8%) (Merck), methanol (99.8%) (Sigma-Aldrich) and toluene (99%) (Sigma-Aldrich). The other substances and materials used are of analytical grade and used without special treatment. Refractive index is measured by Abbe refractometer. FT-IR spectra was determined with a Perkin Elmer FT-IR Spectrum 100. The chromatographic analysis was performed on a high performance liquid chromatograph (HPLC) (JASCO), detector model PDA MD-1510; separation and quantitation were made on Kromasil column, 250 mm × 4 mm (i.d) (5 μm particle size). The injection volume was 7.0 μL, with a flow rate of 1.0 ml/min and the run time was 10 minutes.The solvents and reagents used were toluenul (Sigma-Aldrich Chemical, Steinheim, Germany) and acetone (Merck, Germany). Phenol is heated with chloroform and NaOH. It works in the presence of a mixture of solvents. The reaction temperature of the mixture will be maintained for a period of time sufficient to ensure the largest possible conversion of reagents. Salicylaldehyde is then separated from the reaction mixture by adding water to the reaction mixture. Solvents are distilled off, and then acidified and salicylaldehyde was removed by steam entrainment. RESULTS DISCUSSION To determine the optimum conditions of synthesis the variation of various reaction parameters was studied, such as: the ratio of reactants, the solvent used, the time of synthesis, reaction temperature, steam entrainment method of the product from the reaction mixture. Influence of solvent Because some synthesis is performed in the presence of mixtures of solvents, we tried to find mixtures that will produce good returns. 59 C RIŞ AN R., M ODRA D. In the summaries have used three different solvent mixtures. Option I contains a mixture of methanol: toluene ratio of 1:1. Variant II contains a mixture of ethanol: toluene ratio of 1:1, and variant III a mixture of isopropanol: toluene ratio of 1:1. The amount of solvent used is 20% compared to the amount of phenol and chloroform used in the reaction It works with a molar ratio of phenol:chloroform 1:2, the reaction time used is 90 minutes. In the reaction sodium hydroxide is used in a proportion of 10% relative to the amount of phenol. The synthesis time is 1.5 hours. The results obtained are shown in Table I: Table I. Experimental data obtained Nr. crt. Solvent Yield [ % ] 1 H2O 54.5 2 Option I 60.2 3 Option II 50.9 4 Option III 49.1 Figure 1 playback performance variation depending on the mixture of solvents used. Figure 1. The variation of the yield depending on the reaction solvents It is observed from the experimental data that the best yield is obtained by working with Option I of solvent (methanol: toluene 1:1), the value is 60.2%. The other variants of solvents used gives yields around 50%. Temperature in the last two variants of the solvent was about 80-90º C and 65-68º C in Option I. In the synthesis were solvent is not used, the reaction temperature was 60-65º C. Following these synthesis, we agreed to find the best working conditions for obtaining high yields in anhydride salicylic version that uses a solvent mixture of ethanol: toluene. 60 THE SYNTHESIS OF SALICYLALDEHYDE VARYING DIFFERENT PARAMETERS The influence of the molar ratio of the reactants To determine the influence of the molar ratio of the reactants on the yield of the reaction, we have used different molar ratios of phenol: chloroform 1:1, 1:1.5, 1:2, 1:3. Temperature was 65-67º C. Synthesis time was 1 hour and 30 minutes, and sodium hydroxide was used in 10% of the quantity of phenol. It works in the presence of a solvent mixture of methanol: toluene, ratio 1:1. The amount of solvent used is 20% compared to the amount of phenol and chloroform used in the reaction. The results obtained are shown in Table II: Table II. Experimental data in the synthesis of salicylaldehyde Nr. crt. Molar ratio Yield [%] phenol:chloroform 1 1:1 20.6 2 1:1.5 54.1 3 1:2 60.2 4 1:3 63.5 In Figure 2 is represented on graph the variation of yield by different molar ratios of phenol: chloroform, used in synthesis. Figure 2 : Variation of yield on different molar ratios of phenol: chloroform From the graphical representation is found that the yield of salicylaldehyde increases with increasing molar ratio of reactants phenol: chloroform. It is also apparent that the increase in yield a molar ratio of phenol:chloroform 1:2 at a ratio of 1:3 is rather less than about 3%, it is better to work with lower molar ratio. This allows us to not use an excessive quantities of chloroform, which then must be recovered and purified Influence of synthesis time It works at different values of the reaction time to determine the best value for 61 C RIŞ AN R., M ODRA D.
Load more

Recommended publications
  • Cv1p0149.Pdf
    A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training in experimental organic chemistry. All hazardous materials should be handled using the standard procedures for work with chemicals described in references such as "Prudent Practices in the Laboratory" (The National Academies Press, Washington, D.C., 2011; the full text can be accessed free of charge at http://www.nap.edu/catalog.php?record_id=12654). All chemical waste should be disposed of in accordance with local regulations. For general guidelines for the management of chemical waste, see Chapter 8 of Prudent Practices. In some articles in Organic Syntheses, chemical-specific hazards are highlighted in red “Caution Notes” within a procedure. It is important to recognize that the absence of a caution note does not imply that no significant hazards are associated with the chemicals involved in that procedure. Prior to performing a reaction, a thorough risk assessment should be carried out that includes a review of the potential hazards associated with each chemical and experimental operation on the scale that is planned for the procedure. Guidelines for carrying out a risk assessment and for analyzing the hazards associated with chemicals can be found in Chapter 4 of Prudent Practices. The procedures described in Organic Syntheses are provided as published and are conducted at one's own risk. Organic Syntheses, Inc., its Editors, and its Board of Directors do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein.
    [Show full text]
  • Multicatalytic, Asymmetric Michael/Stetter Reaction Of
    Multicatalytic, asymmetric Michael/Stetter reaction SPECIAL FEATURE of salicylaldehydes and activated alkynes Claire M. Filloux, Stephen P. Lathrop, and Tomislav Rovis1 Department of Chemistry, Colorado State University, Fort Collins, CO 80523 Edited by David W. C. MacMillan, Princeton University, Princeton, NJ, and accepted by the Editorial Board May 30, 2010 (received for review March 22, 2010) We report the development of a multicatalytic, one-pot, asymmetric Ar Ar Michael/Stetter reaction between salicylaldehydes and electron- N H deficient alkynes. The cascade proceeds via amine-mediated OO 3 OTMS (20 mol %) Me HO Me Michael addition followed by an N-heterocyclic carbene-promoted Me Me 1 Ar = 3,5-(CF3)2C6H3 O intramolecular Stetter reaction. A variety of salicylaldehydes, dou- + O O BF4 N bly activated alkynes, and terminal, electrophilic allenes participate 2 Me 5 Me in a one-step or two-step protocol to give a variety of benzofura- NNC F 4a 6 5 One-Pot Two - Po t none products in moderate to good yields and good to excellent (10 mol %) 93% yield 46% yield NaOAc (10 mol %) 85:15:<1:<1 dr 5:1 dr enantioselectivities. The origin of enantioselectivity in the reaction 86% ee 58% ee CHCl3, 23 C is also explored; E∕Z geometry of the reaction intermediate as well as the presence of catalytic amounts of catechol additive are O found to influence reaction enantioselectivity. O Me * O Me ∣ ∣ catalysis organic synthesis tandem catalysis Me 6 ascade catalysis has garnered significant recent attention Scheme 1. Multicatalytic Michael/Benzoin cascade. Cfrom the synthetic community as a means to swiftly assemble CHEMISTRY complex molecules from simple starting materials with minimal benzofuranones.
    [Show full text]
  • Note to Users
    NOTE TO USERS This reproduction is the best copy available Synthetic Approaches to Coniochaetones A & B Leo James Patrick Martyn A thesis submitted in conformity with the requirements for the degree of Master of Science Graduate Department of Chemistry University of Toronto @ Copyright by Leo James Patrick Martyn 1999 National Library Bibliothèque nationale * of Canada du Canada Acquisitions and Acquisitions et Bibliographie Services seMces bibliographiques 395 Wellington Street 395, nie Wellington OltawaûN KIAW OnawaON K1AW Canada Canada The author has granted a non- L'auteur a accordé une licence non exclusive licence allowing the exclusive permettant à la National Library of Canada to Bibliothèque nationale du Canada de reproduce, loan, distribute or seU reproduire, prêter, distribuer ou copies of this thesis in microform, vendre des copies de cette thèse sous paper or electronic formats. la forme de microfiche/film, de reproduction sur papier ou sur format électronique. The author retains ownership of the L'auteur conserve la propriété du copyright in this thesis. Neither the droit d'auteur qui protège cette thèse. thesis nor substantial extracts fiom it Ni la thèse ni des extraits substantiels may be printed or otherwise de celle-ci ne doivent être imprimés reproduced without the author's ou autrement reproduits sans son permission. autorisation. Abstract Several routes to the synthesis of coniochaetones A and B, two natural products isolated from a liquid culture of Coniochaeta soccardoi,' were explored. Two different pathways which we believe will eventually lead to the synthesis of coniochaetones A and B have been focused upon. Utilizing a mode1 senes, key intermediates for each synthetic route have been synthesized and characterized.
    [Show full text]
  • Synthesis and Antidepressant Activity of Some New Coumarin Derivatives
    Scientia Pharmaceutica (Sci. Pharm.) 74, 193-216 (2005) O Osterreichische Apotheker-Verlagsgesellschafl m. b. H., Wien, Printed in Austria Synthesis and Antidepressant Activity of Some New Coumarin Derivatives Nehad A. Abdel-Latif Natural Compounds Department, National Research Centre, Dokki, Cairo, Egypt; E-mail: [email protected] Abstract The coumarin-3-cinnamoyl derivatives 2a-d were prepared via Claisen- Schmidt condensation of 3-acetylcoumarin 1 with different aromatic aldehydes. Cycloaddition reaction of 2b,e with guanidine and thiourea yielded the corresponding aminopyrmimidine 3a,b and thioxypyrimidine derivatives 4a,b, respectively. Compounds 4a,b were condensed with chloroacetic acid or 3- bromopropionic acid to yield coumarin 3-thiazolo-pyrimidine 5a,b and thiazinopyrimidine 6a,b derivatives, respectively. Compounds 4a,b were condensed with chloroacetic acid and aromatic aldehyde to yield the aryl methylene derivatives 7a,b which could be prepared directly by condensation of compounds 5a,b with aromatic aldehydes. Compounds 2a-e were condensed with malononitrile or ethyl cyano acetate in presence of ammonium acetate to yield cyanopyridine 8a,b and cyanopyridone 9a- d derivatives, respectively, which were prepared by condensation of 3- acetylcoumarin 1, malononitrile or ethylcyanoacetate and aromatic aldehydes in presence of ammonium acetate. Condensation of compounds 2a,b,e with o-phenylenediamine in refluxing ethanol led to the formation of 10a-c as intermediate, followed by cleavage by thermolysis to benzimidazole derivative 11 along with compounds 12a-c as mixture, which were obtained directly by fusion of a,&unsaturated ketones 2 with o- phenylene diamine at 200-220°C, while compound 11 could be prepared in pure form by fusion of 1 with o-phenylene diamine at the same temperature.
    [Show full text]
  • Part I: Synthesis of Functionalized Bile Acids Towards The
    PART I: SYNTHESIS OF FUNCTIONALIZED BILE ACIDS TOWARDS THE CONSTRUCTION OF STEROIDAL MACROCYCLES. PART II: EVALUATION AND EXPANSION OF A MODULAR CARD GAME FOR TEACHING ORGANIC CHEMISTRY A DISSERTATION IN Chemistry and Pharmaceutical Sciences Presented to the Faculty of the University of Missouri-Kansas City in partial fulfillment of the requirements for the degree DOCTOR OF PHILOSOPHY by CHRISTOPHER ANTON KNUDTSON B.S., Saint Louis University 2004 M.S., Kansas University 2011 Kansas City, Missouri 2019 © 2019 CHRISTOPHER ANTON KNUDTSON ALL RIGHTS RESERVED PART I: SYNTHESIS OF FUNCTIONALIZED BILE ACIDS TOWARDS THE CONSTRUCTION OF STEROIDAL MACROCYCLES. PART II: EVALUATION AND EXPANSION OF A MODULAR CARD GAME FOR TEACHING ORGANIC CHEMISTRY Christopher A. Knudtson, Candidate for the Doctor of Philosophy Degree University of Missouri-Kansas City, 2019 ABSTRACT In Part I, the synthesis of chenodeoxychoic acid (CDCA) derivatives towards the construction of unique chemical architectures are reported. Building on previously described methods, CDCA based macrocycles with inner cavities have been synthesized and characterized. Attempts toward oxa-Michael coupling of CDCA monomers to form sulfonate ester linked dimmers is described. CDCA was also functionalized with terminal alkynes (pentynyl, hexynyl, and heptynyl) and aryl iodide and cyclized to from the respective macrocycles. These have been coupled together via oxygen-free Sonogashira reaction conditions to form large barrel-like steroidal architectures. These structures were investigated by 1H NMR, 13 C NMR spectroscopy, and HR-MS, and MALDI-TOF spectroscopy. In part II a game to teach organic chemistry, ChemKarta was evaluated as a teaching tool. Analysis of an undergraduate class’s impressions of the game showed that Chemkarta was an easy to learn and enjoyable game, but the amount of information in the game could be overwhelming for some students.
    [Show full text]
  • Trusscore Chemical Resistance Chart
    Chemical Resistance Chart Table courtesy of JENSEN INERT PRODUCTS, INC. Resistance Material E = Excellent G = Good F = Fair PVC = Polyvinylchloride N = Not Recommended This information, based on experience to date, is believed to be reliable. It is intended as a guide for use at your own discretion and risk. All indications refer to room temperature. Chemical PVC Chemical PVC Acetaldehyde G Calcium Hypochlorite G Acetamide N Carbazole N Acetic Acid, 5% E Carbon Disulfide N Acetic Acid, 50% E Carbon Tetrachloride G Acetone E Chlorine E Aluminum Hydroxide E Chloroacetic Acid F Ammonia E Chloroform N Ammonium Hydroxide E Chromic Acid E Ammonium Oxalate E Citric Acid G n-Amyl Acetate F Cresol N Amyl Chloride N Cyclohexane G Aniline N Chemical PVC Chemical PVC Decalin E Benzaldehyde N o-Dichlorobenzene G Benzene N p-Dichlorobenzene N Benzoic Acid, Sat. E Diethyl Benzene N Benzyl Acetate F Diethyl Ether F Boric Acid E Diethyl Ketone N Bromine G Diethyl Malonate G Bromobenzene F Dimethyl Formamide F n-Butyl Acetate N sec-Butyl Alcohol G Chemical PVC Butyric Acid G Ether F Ethyl Acetate F Chemical PVC Ethyl Benzene N Nitric Acid, 50% G Ethyl Benzoate N Nitric Acid, 70% F Ethyl Butyrate N Nitrobenzene N Ethyl Chloride, Liquid N n-Octane F Ethyl Cyanoacetate NF Orange Oil F Ethyl Lactate F Ethylene Chloride N Chemical PVC Ethylene Glycol E Perchloric Acid G Ethylene Oxide F Perchloroethylene N Phenol, Crystals F Chemical PVC Phosphoric Acid, 1-5% E Fluorine N Phosphoric Acid, 85% E Formic Acid, 50% G Potassium Hydroxide E Formic Acid, 90-100% F Propane Gas E Fuel Oil E Propylene Glycol F Gasoline G Propylene Oxide F Glycerine E Chemical PVC Chemical PVC Resorcinol F n-Heptane F Salicylaldehyde F Hexane G Sulfuric Acid, 1-6% E Hydrochloric Acid, 1-5% E Sulfuric Acid, 20% E Hydrochloric Acid, 35% G Sulfuric Acid, 60% E Hydrofluoric Acid, 4% G Sulfuric Acid, 98% N Hydrofluoric Acid, 48% G Sulfur Dioxide, Liq.
    [Show full text]
  • United States Patent Office Patented Jan
    United States Patent Office Patented Jan. 23, 1968 1. 2 3,365,500 Therefore, from what information appears in the litera HYDROXYBENZALDEHYDE PROCESS ture, there would seem to be little advantage to be gained Donald F. Pontz, Midland, Mich., assignor to The Dow by using aqueous ethyl alcohol as a solvent in the prepara Chemical Company, Midland, Mich., a corporation of tion of Salicylaldehyde by this method. There is nothing Delaware to incline a chemist to investigate other alcoholic solvents No Drawing. Filed Jan. 21, 1964, Ser. No. 339,104 as the means by which improved results might be obtained. 5 Claims. (C. 260-600) Consequently, it is surprising and unexpected to find that aqueous methanol used as the solvent medium for the preparation of Salicylaldehyde by the Reimer-Tiemann ABSTRACT OF THE DISCLosURE 10 reaction provides both better combined yields of hy In the Reimer-Tiemann reaction wherein phenol is droxyaldehydes and sharply reduced tar formation as com reacted with chloroform and an alkali metal base to make pared to the results obtained by using either water or salicylaldehyde and p-hydroxybenzaldehyde, improved aqueous ethyl alcohol as the reaction solvent. By using yields of total aldehydes and decreased tar formation are as the Solvent aqueous methanol containing from about obtained when the reaction medium is aqueous methanol 5 10% to about 75% by weight of methanol, the yield of of 10-75 percent by weight concentration as compared Salicylaldehyde is at least as good as that obtained with to reactions run in water alone or in aqueous ethanol. The Water or aqueous ethyl alcohol and the yield of the improvement in total aldehyde yield is due principally to valuable p-hydroxybenzaldehyde is considerably better.
    [Show full text]
  • Fluorescent Iridium(III) Coumarin-Salicylaldehyde Schiff Base Compounds As Lysosome-Targeted Antitumor Agents
    Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is © The Royal Society of Chemistry 2020 Fluorescent Iridium(III) Coumarin-salicylaldehyde Schiff Base Compounds as Lysosome-Targeted antitumor agents Cong Liu, Xicheng Liu*, Xingxing Ge, Qinghui Wang, Lei Zhang, Wenjing Shang, Yue Zhang, XiangAi Yuan, Laijin Tian, Zhe Liu*, Jinmao You Institute of Anticancer Agents Development and Theranostic Application, The Key Laboratory of Life-Organic Analysis and Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China. *Corresponding authors (Email): [email protected] (X. C. Liu); [email protected] (Z. Liu) Supporting Information Experimental Section .....................................................................................................................2 Synthesis.........................................................................................................................................6 Figures S1-S16..........................................................................................................................7 Tables S1-S9...................................................................................................................................24 1 EXPERIMENTAL SECTION NMR Spectrum NMR spectra were acquired in 5 mm NMR tubes at 298 K on Bruker DPX 500 (1H NMR: 500.13 MHz; 13C NMR: 126 MHz; 19F NMR: 471 MHz) spectrometers. 1H NMR chemical shifts were internally referenced
    [Show full text]
  • Role of Nicotinamide and Salicylaldehyde on Some Growth Parameters in Wheat
    ©Verlag Ferdinand Berger & Söhne Ges.m.b.H., Horn, Austria, download unter www.biologiezentrum.at Phyton (Austria) Vol. 29 Fasc. 1 33-40 16. 5. 1989 Role of Nicotinamide and Salicylaldehyde on Some Growth Parameters in Wheat Youssef A. H. MOHAMED, Ahmed SHARAF EL-DIN & El-Sayed FODA With 3 Figures Received January 13, 1988 Key words: Nicotinamide, salicylaldehyde, growth, wheat, Triticum. Summary MOHAMED Y. A. H., SHARAF EL-DIN A. & FODA E. 1989. Role of nicotinamide and salicylaldehyde on some growth parameters in wheat. - Phyton (Austria) 29 (1): 33-40, with 3 figures. - English with German summary. The effect of 1(T4 and 1CT5 M nicotinamide and salicylaldehyde was shown in favour of the increase in root and shoot length. The area of the leaf in plants treated with nicotinamide increased and the width decreased. Salicylaldehyde exerted neu- tral effect on leaf. Both growth regulators increased the level of total soluble carbohydrates and total soluble proteins throughout the overall age of the plant and in the different plant organs. As a result of these growth regulators application, DNA quantities decreased in the root and stem and increased in the leaf, while inhibition of RNA synthesis was observed. Zusammenfassung MOHAMED Y. A. H., SHARAF EL-DIN A. & FODA E. 1989. Der Einfluß von Nikotinamid und Salicylaldehyd auf einige Wachstumsparameter bei Weizen. - Phyton (Austria) 29 (1): 33-40, mit 3 Figuren. - Englisch mit deutscher Zusammen- fassung. 10"4 und 10~5 M Nikotinamid und Salicylaldehyd begünstigten das Längen- wachstum von Wurzel und Sproß. Die Blattfläche nikotinamidbehandelter Pflanzen nahm zu, während deren Breite abnahm.
    [Show full text]
  • Synthetic and Meschanistic Studies of The
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by South East Academic Libraries System (SEALS) APPLICATIONS OF THE BAYLIS-HILLMAN REACTION IN THE SYNTHESIS OF COUMARIN DERIVATIVES A thesis submitted in fulfilment of the requirements for the degree DOCTOR OF PHILOSOPHY of RHODES UNIVERSITY by MUSILIYU AYODELE MUSA M.Sc (Lagos) Department of Chemistry Rhodes University Grahamstown January 2002 ABSTRACT The reaction of specially prepared salicylaldehyde benzyl ethers with the activated alkenes, methyl acrylate or acrylonitrile, in the presence of the catalyst, DABCO, has afforded Baylis-Hillman products, which have been subjected to conjugate addition with either piperidine or benzylamine. Hydrogenolysis of these conjugate addition products in the presence of a palladium-on-carbon catalyst has been shown to afford the corresponding 3-substituted coumarins, while treatment of O-benzylated Baylis- Hillman adducts with HCl or HI afforded the corresponding 3-(halomethyl)coumarins directly, in up to 94%. The 3-(halomethyl)coumarins have also been obtained in excellent yields (up to 98%) and even more conveniently, by treating the unprotected Baylis-Hillman products with HCl in a mixture of AcOH and Ac2O, obtained from tert-butyl acrylate and various salicylaldehydes. The generality of an established route to the synthesis of coumarins via an intramolecular Baylis-Hillman reaction, involving the use of salicylaldehyde acrylate esters in the presence of DABCO, has also been demonstrated. Reactions between the 3-(halomethyl)coumarins and various nitrogen and carbon nucleophiles have been shown to proceed with a high degree of regioselectivity at the exocyclic allylic centre to afford 3-substituted coumarin products.
    [Show full text]
  • Summary: Synthesis of Salicylaldehyde and Its Applications Twghs Kap Yan Directors’ College Introduction
    Summary: Synthesis of Salicylaldehyde and its Applications TWGHs Kap Yan Directors’ College Introduction Salicylaldehyde (SA) (C6H4CHO-2-OH) is a useful aromatic organic chemical. It is a common reactant for many synthesis, such as cyclic organic compounds like coumarin and organic ligand such as salan ligand. Salicylaldehyde is also crucial to our daily lives. In A. Ravin’s medical publication, it is mentioned that SA can be used for detection of ketonuria in medical treatment. It also serves as a chelating agent with heavy metal ions such as Copper(II) ion, which is applicable to colorimetric analysis of the concentration of heavy metal ions in water sample. SA is also a precursor in total synthesis of coumarin (C9H6O2), which is a white organic crystal with antibacterial activities. However, salicylaldehyde is not commonly stored in secondary schools’ laboratories. People can only buy a relatively large amount of salicylaldehyde with high price from chemical suppliers. In our research project, we used a simple one-pot reaction to synthesize salicylaldehyde from phenol (C6H5OH), sodium hydroxide (NaOH) and chloroform (CHCl3) which are available in school laboratory. The synthesis, separation and identification are carried under a normal secondary school laboratory without using advanced laboratory devices and apparatus. Meanwhile, several applications of salicylaldehyde were also investigated, for instance the synthesis of coumarin, metal complex chelation and the medical detection of ketonuria. Figure 1: Chemical structure of salicylaldehyde Figure 2: Appearance of salicylaldehyde Part 1: Synthesis By Reimer-Tiemann Reaction, phenol reacts with chloroform to form SA under refluxing for 1 hour in 65℃ water bath. This method is simple to carry out with a relatively high yield of SA obtained (~30%).
    [Show full text]
  • Bis(Salicylidene)Ethylenediamine(Salen) and Bis(Salicylidene)Ethylenediamine-Metal Complexes: from Structure to Biological Activity
    Journal of Analytical & Pharmaceutical Research Bis(Salicylidene)Ethylenediamine(Salen) and Bis(Salicylidene)Ethylenediamine-Metal Complexes: from Structure to Biological Activity Abstract Review Article Schiff bases and their metal complexes have occupied a central role in the Volume 3 Issue 6 - 2016 development of co-ordination chemistry as evidenced by the vast number, ease and flexibility of the synthetic procedure, diverse properties, and use as biologically active compounds as antitumor, antibacterial, antifungal and other miscellaneous Department of Industrial Chemistry, Ebonyi State University, biological applications. Many reports have demonstrated that Salen and Salen- Nigeria metal complexes are highly active against several diseases, including cancer. The thrust of this review work is to evaluate the structural nature of Salen and assess *Corresponding author: Felix Sunday Nworie, Department the biological applications thereof. of Industrial Chemistry, Ebonyi State University, PMB 053 Abakaliki, Ebonyi State, Nigeria, Tel: +2348034813342; Keywords: Schiff base; Salen; Metal salen; Biological applications; Structural Email: characterization Received: October 31, 2016 | Published: December 15, 2016 Abbreviations: C: Carbon; N: Nitrogen; DMSO: Dimethylsulphoxide; PXRD: Powder X-ray Diffractometer; the elimination of the hemiaminal (carbinolamine) hydroxyl SOD: Superoxide Dismutase; Cu: Copper; Zn: Zinc; Fe: Iron; groupconditions, (dehydration there is unavailabilitystep) [5]. of sufficient protons to catalyze Cr: Chromium; Mn:
    [Show full text]