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Journal Science Intensive Technologies №3 for 2013 г.
Article in number:
Preparation ethylenediamine derivatives, containing propionic groups under conditions of template synthesis
Authors:
O.N. Podmareva, N.V. Tsirul-nikova, Y.P. Krysin, E.S. Dernovaya
Abstract:
Under conditions oftemplate synthesis in the presence of CaO has managed to change the direction of reaction carboxyalkylation of ethylenediaminemonochloroacetic (MCA) and mono-3-chloropropionic (MCP) acids and to stop this process at an intermediate stage of the formation of derivatives of ethylenediamine incomplete degree of substitution with carboxylic groups of protons - ethylenediamine-N, N\'-diacetic (sym.EDDA) and ethylenediamine-N, N\'-dipropionic (sym.EDDP) acids, respectively. Apart from sym.EDDA was identified ethylenediamine-N-monoaceticacid (EDMA) from the reaction mixture. The participation of MCP in the side reactions, including reaction of elimination MCP to acrylic acid, explains the low yield sym.EDDP (≈ 40%). It was also interesting to study the process of interaction between ethylenediamine and product of elimination MCP - acrylic acid, under conditions oftemplate synthesis. In the presence of Cu2+ ions was obtained an unexpected result - the simultaneous formation sym.EDDP in the form of its copper complex and ethylenediamine-N-mono-3-propionic acid (EDMP). The template synthesis, as a result of which were obtained two different by nature products, was described for the first time. Undescribed before EDMP was separate in the form of sulfate and characterized by physicochemical methods.
Pages: 16-23
References
  1. Mashkovskijj M.D. Lekarstvennye sredstva. M.: Novaja volna. 2010. S. 1216.
  2. Djatlova N.M., Temkina V.JA., Kolpakova I.D.Kompleksony. M.: KHimija. 1970. S. 416.
  3. Patent RU 2307828 C1 20071010. Sposob poluchenija ehtilendiamin-N,N?-dipropionovojj kisloty digidrokhlorida / N.V. Cirulnikova, M.A.Tarasova. 2007.
  4. Cirulnikova N.V., CHicherina G.P., Fetisova T.S. Karboksialkilirovanie ehtilendiamina beta-khlorpropionovojj kislotojj. Novyjj sposob poluchenija ehtilendiamin-N,N\'-di i ehtilendiamin-N,N,N\',N\'-tetrapropionovykh kislot // ZHurnal obshhejj khimii. 2010. T. 80. № 3. S. 515-516.
  5. Patent RU 2308448 C1 20071020. Sposob poluchenija ehtilendiamin-N,N,N\',N\'-tetrapropionovojj kisloty / N.V. Cirulnikova, G.P. CHicherina. 2007.
  6. Watson M.J., Pesterfield L.L., Dahl D.B. Synthesis and characterization of polyaminopolycarboxylic acid analogs of EDTA and their transition metal complexes // Western Kentucky University. 2005. R. 13-17.
  7. Zhadanov B.V., Tsirul-nikova N.V., Polyakova I.A.Synthesis of new complexons. N-Hydroxy-α,α?-iminodipropionic and N-hydroxyiminodiacetic acid // Zeitschrift fuer naturforschung, Teil B: anogranische chemie, organische chemie. 1986. V. 41B. № 3. R. 359-362.
  8. Ewin G., Hill J.O. A thermometric titrimetric study of the complexation of alkaline earth metals by linear poly(aminocarboxylic) acids // Journal of the Chemical Society. 1983. V. 5. P. 865-868.
  9. Neudachina L.K., Yatluk Y.G., Baranova N.V. Synthesis and physicochemical properties of chelating sorbents containing functional groups of N-aryl-3-aminopropionic acids // Russian Chemical Bulletin. 2006. V. 55. № 5. R. 828-834
  10. Asano T., Yabusaki K., Wang P., Iwasaki A.Determination of lead(II) in fly ash leachate using a newly developed simple spectrophotometric method // Spectrochim. Acta, Part A: Molecular and Biomolecular Spectroscopy. 2010. V. 75A. № 2. P. 819-824.
  11. Narita M., Hino M., Takuba T., Tatsumi N. Analogues of ethylenediaminetetraacetic acid and sodium fluoride as anticoagulants // Osaka City Med. J. 2000. V. 46. № l. P. 71-87.
  12. Vesna M.D., Verica V.G., Gordana P.V., Vladimir T., Olivera K., Slobodanka S., Tibor J.S., Srećko R.T.Stereospecific ligands and their complexes. IV: Synthesis, characterization and cytotoxicity of novel platinum(IV) complexes with ethylenediamine-N,N′-di-S,S-2-propanoate and halogenido ligands: Crystal structure of s-cis-[Pt(S,S-eddp)Cl2]·4H2O and uns-cis-[Pt(S,S-eddp)Br2] // Polyhedron. 2010. V. 29. № 8. P. 1933-1938.
  13. Sanja R.G., Rosario A.V., José M.P., Miguel A.F., Carlos A., Ysmael A., Tibor J.S., Francisco G.Synthesis, characterization, interaction with DNA and cytotoxicity of the new potential antitumour drug cis-K[Ru(eddp)Cl2] // Journal of Inorganic Biochemistry. 2003. V. 97. № 2. P. 215-220.
  14. Sakurai H., Kojima Y., Yoshikawa Y., Kawabe K., Yasui H.Antidiabetic vanadium(IV) and zinc(II) complexes // Coordination Chemistry Reviews. 2002. V. 226. R. 187-198.
  15. Kawabe K., Tadokoro M., Hirotsu K., Yanagihara N., Kojima Y.Syntheses and crystal structures of oxovanadium(IV) complexes with N,N\'-ethylenebis(amino acids) // Inorganica Chimica Acta. 2000. V. 305. R. 172-183.
  16. Mori M., Gahwiler B.H., Gerber U. β-Alanine and taurine as endogenous agonists at glycine receptors in rat hippocampus in vitro // Journal of Physiology. 2002. V. 539. № 1. R. 191-200.
  17. Temkina V.Ya., Tsirul-nikova N.V., Demina N.P.Carbokyalkilation of aliphatic amines with monochloracetic acid in the presence of alkaline-earth and transition metals // Tezisydokl. VI Mezhdunar. konf. poorganicheskomusintezu. M. 1986. A-383.
  18. Badea M., Olar R., Marinescu D., Vasile G., Jurca B., Madalan A.M., Andruh M. A. Michael-type reaction between acrylato ions and ethylenediamine coordinated to Ni(II). Synthesis, crystal structure and magnetic properties of [Ni2(EDDP)2(H2O)2]·2H2O (H2EDDP = ethylenediamine-N,N-dipropionic acid) // Inorganic Chemistry Communications. 2009. V. 12. № 6. P. 555-557.
  19. Bruker Programs APEX II, version 2.0-1; SAINT, version 7.23A; SADABS, version 2004/1; XPREP, version 2005/2; SHELXTL, version 6.1. Bruker AXS Inc., Madison, WI, USA, 2005.