Araştırma Makalesi
BibTex RIS Kaynak Göster

PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+

Yıl 2017, Cilt: 18 Sayı: 3, 720 - 732, 30.09.2017
https://doi.org/10.18038/aubtda.318087

Öz



In
this study,
tetramethylethylenedimine copper(II) complex (Cu(tmen)Cl2)
was synthesized and natural clay smectite and synthetic Dowex-50WX8

resin containing Cu(tmen)(OH)(OH2)+
were prepared via ion exchange process in aqueous solution. Dowex- and smectite-supported
Cu(tmen)(OH)(OH2)+ were used as a promoter in the
hydrolysis reactions of organophosphate compounds of diethyl-p-nitrophenyl
phosphate and p-nitrophenyl diphenyl phosphate at different pH values.
Scanning electron microscope attached
with energy dispersive X-ray dedector and surface area analyzer were used for
the characterization of the promoters. The efficiency of these promoters was
evaluated in accordance with pseudo-first-order and Michaelis-Menten enzyme
kinetic models. The amount of copper(II) complex in
Dowex-supported promoter was
higher than that of
smectite-supported one (1.36 mmol/g and 0.88 mmol/g, respectively) and the higher efficiency was
obtained when Dowex-supported promoter was employed in all of the hydrolysis
reactions. 222 and 114-fold increasing in pseudo-first-order rate constants
compared to the reactions without promoter were observed for the hydrolysis of diethyl-p-nitrophenyl
phosphate at pH 8.0 in the presence of Dowex-supported and smectite-supported promoters.




Kaynakça

  • Toy ADF, Walsh EN. Phosphorus Chemistry in Everyday Living. 2nd ed. Washington, DC, USA: American Chemical Society, 1987.
  • Morales-Rojas H, Moss RA. Phosphorolytic reactivity of o-iodosylcarboxylates and related nucleophile. Chem Rev 2002; 102: 2497-2521.
  • Quin LD. A Guide to Organophosphorus Chemistry. New York, NY, USA: Wiley, 2000.
  • Yang YC, Baker JA, Ward JR. Decontamination of chemical warfare agents. Chem Rev 1992; 92: 1729-1743.
  • Munro NB, Ambrose KR, Watson AP. Toxicity of the organophosphate chemical warfare agents GA, GB, and VX-implications for public protection. Environ Health Perspect 1994;102: 18-38.
  • Gallo MA, Lawryk NJ. Organic Phosphorus Pesticides. The Handbook of Pesticide Toxicology. San Diego, CA, USA: Academic Press, 1991.
  • Mersal GAM, Ibrahim MM. Solution studies of tris(2-benzylaminoethyl)amine complexes of zinc(II) and copper(II): The catalytic hydrolysis of toxic organophosphate. Cr Chim 2012; 15: 336-345.
  • Tafesse F. Hydrolysis of nerve agent simulants by synergistic effects of tetraminecobalt(III) and microemulsions. Inorg Chim Acta 1998; 269: 287-291.
  • Scrimin P, Ghirlanda G, Tecilla P, Moss RA. Comparative reactivities of phosphate ester cleavages by metallomicelles. Langmuir 1996; 12: 6235-6241.
  • Hafiz, AA. Metallosurfactants of Cu(II) and Fe(III) complexes as catalysts for the destruction of paraoxon. J Surfactants Deterg 2005; 8: 359-363. Hay RW, Govan N. The [CoN4(OH)(OH2)]2+ (N4 = trpn, cyclen and tren) promoted hydrolysis of the phosphotriester 2,4-dinitrophenyl diethyl phosphate. Transit Metal Chem 1998; 23: 721-725.
  • Moss RA, Alwis KW, Bizzigotti GO. Ortho-iodosobenzoate-catalyst for the micellar cleavage of activated esters and phosphates. J Am Chem Soc 1983; 105: 681-682.
  • Katritzky AR, Duell BL, Durst HD, Knier BL. Substituted o-iodoso- and o-iodoxybenzoic acids. Synthesis and catalytic activity in the hydrolysis of active phosphorus esters and related systems. J Org Chem 1988; 53: 3972-3978.
  • Mackay RA, Longo FR, Knier BL, Durst HD. Iodosobenzoate catalyzed hydrolysis of 4-nitrophenyl diphenyl phosphate in a CTAB microemulsion. J Phys Chem 1987; 91: 861-864.
  • Ford WT, Yu H. Rapid hydrolysis of p-nitrophenyl diphenyl phosphate catalyzed by o-iodosobenzoate in cationic latexes. Langmuir 1991; 7: 615-616.
  • Erdem M, Turk H. Preparation of cationic latexes with different length alkyl groups on their quaternary ammonium ions and their use as supports for IBA catalyst in the hydrolysis of PNPDPP. React Funct Polym 2008; 68: 321-331.
  • Bunton CA, Robinson LB. Micellar effects upon the reaction of p-nitrophenyl diphenyl phosphate with hydroxide and fluoride ions. J Org Chem 1969; 34: 773-780.
  • Manfredi AM, Willian D, Eduardo HW, Silva BV, Pinto AC, Souza BS, Nome F. Rapid cleavage of phosphate triesters by the oxime 2-(hydroxyimino)-N-phenyl-acetamide. J Phys Org Chem 2016; 29: 600-603.
  • Dumas DP, Caldwell SR, Wild JR, Raushel FM. Purification and properties of the phosphotriesterase from pseudomonas-diminuta. J Biol Chem 1989; 264: 19659-19665.
  • Chae MY, Postula JF, Raushel FM. Stereospecific enzymatic-hydrolysis of phosphorus-sulfur bonds in chiral organophosphate triesters. Bioorg Med Chem Lett 1994; 4: 1473-1478.
  • Yamazaki T, Yilmaz E, Mosbach K, Sode K. Towards the use of molecularly imprinted polymers containing imidazoles and bivalent metal complexes for the detection and degradation of organophosphotriester pesticides. Anal Chim Acta 2001; 435: 209-214.
  • Erdem M, Say R, Ersoz A, Denizli A, Turk H. Biomimicking, metal-chelating and surface-imprinted polymers for the degradation of pesticides. React Funct Polym 2010; 70: 238-243.
  • Hegg EL, Burstyn JN. Toward the development of metal-based synthetic nucleases and peptidases: a rationale and progress report in applying the principles of coordination chemistry. Coord Chem Rev 1998; 173: 133-165.
  • Courtney RC, Gustafson RL, Westerback SJ, Hyytiainen H, Chaberek SC, Martell AE. Metal chelate compounds as catalysts in the hydrolysis of isopropylmethylphosphonofluoridate and diisopropylphosphorofluoridate. J Am Chem Soc 1957; 79: 3030-3036.
  • Hartshorn CM, Deschamps JR, Singh A, Chang EL. Metal-chelator polymers as reactive adsorbents for organophosphate hydrolysis. React Funct Polym 2003; 55: 219-229.
  • Blacker NC, Findlay PH, Sherrington DC. Synthesis of Cu-II-complexed polymers and use as catalysts in the hydrolytic decontamination of Sarin nerve agent. Polym Advan Technol 2001; 12: 183-196.
  • Bukowski MR, Hile BL, Figurelli A, Hotham I, Maurer, MK. Insights into heterogeneous phosphodiester hydrolysis using a simple hydrogel-based copper(II)-imidazole catalyst. Inorg Chim Acta 2011; 370: 405-410.
  • Tafesse F. Hydrolysis of nerve agent simulants by synergistic effects of tetraminecobalt(III) and microemulsions. Inorg Chim Acta 1998; 269: 287-291.
Yıl 2017, Cilt: 18 Sayı: 3, 720 - 732, 30.09.2017
https://doi.org/10.18038/aubtda.318087

Öz

Kaynakça

  • Toy ADF, Walsh EN. Phosphorus Chemistry in Everyday Living. 2nd ed. Washington, DC, USA: American Chemical Society, 1987.
  • Morales-Rojas H, Moss RA. Phosphorolytic reactivity of o-iodosylcarboxylates and related nucleophile. Chem Rev 2002; 102: 2497-2521.
  • Quin LD. A Guide to Organophosphorus Chemistry. New York, NY, USA: Wiley, 2000.
  • Yang YC, Baker JA, Ward JR. Decontamination of chemical warfare agents. Chem Rev 1992; 92: 1729-1743.
  • Munro NB, Ambrose KR, Watson AP. Toxicity of the organophosphate chemical warfare agents GA, GB, and VX-implications for public protection. Environ Health Perspect 1994;102: 18-38.
  • Gallo MA, Lawryk NJ. Organic Phosphorus Pesticides. The Handbook of Pesticide Toxicology. San Diego, CA, USA: Academic Press, 1991.
  • Mersal GAM, Ibrahim MM. Solution studies of tris(2-benzylaminoethyl)amine complexes of zinc(II) and copper(II): The catalytic hydrolysis of toxic organophosphate. Cr Chim 2012; 15: 336-345.
  • Tafesse F. Hydrolysis of nerve agent simulants by synergistic effects of tetraminecobalt(III) and microemulsions. Inorg Chim Acta 1998; 269: 287-291.
  • Scrimin P, Ghirlanda G, Tecilla P, Moss RA. Comparative reactivities of phosphate ester cleavages by metallomicelles. Langmuir 1996; 12: 6235-6241.
  • Hafiz, AA. Metallosurfactants of Cu(II) and Fe(III) complexes as catalysts for the destruction of paraoxon. J Surfactants Deterg 2005; 8: 359-363. Hay RW, Govan N. The [CoN4(OH)(OH2)]2+ (N4 = trpn, cyclen and tren) promoted hydrolysis of the phosphotriester 2,4-dinitrophenyl diethyl phosphate. Transit Metal Chem 1998; 23: 721-725.
  • Moss RA, Alwis KW, Bizzigotti GO. Ortho-iodosobenzoate-catalyst for the micellar cleavage of activated esters and phosphates. J Am Chem Soc 1983; 105: 681-682.
  • Katritzky AR, Duell BL, Durst HD, Knier BL. Substituted o-iodoso- and o-iodoxybenzoic acids. Synthesis and catalytic activity in the hydrolysis of active phosphorus esters and related systems. J Org Chem 1988; 53: 3972-3978.
  • Mackay RA, Longo FR, Knier BL, Durst HD. Iodosobenzoate catalyzed hydrolysis of 4-nitrophenyl diphenyl phosphate in a CTAB microemulsion. J Phys Chem 1987; 91: 861-864.
  • Ford WT, Yu H. Rapid hydrolysis of p-nitrophenyl diphenyl phosphate catalyzed by o-iodosobenzoate in cationic latexes. Langmuir 1991; 7: 615-616.
  • Erdem M, Turk H. Preparation of cationic latexes with different length alkyl groups on their quaternary ammonium ions and their use as supports for IBA catalyst in the hydrolysis of PNPDPP. React Funct Polym 2008; 68: 321-331.
  • Bunton CA, Robinson LB. Micellar effects upon the reaction of p-nitrophenyl diphenyl phosphate with hydroxide and fluoride ions. J Org Chem 1969; 34: 773-780.
  • Manfredi AM, Willian D, Eduardo HW, Silva BV, Pinto AC, Souza BS, Nome F. Rapid cleavage of phosphate triesters by the oxime 2-(hydroxyimino)-N-phenyl-acetamide. J Phys Org Chem 2016; 29: 600-603.
  • Dumas DP, Caldwell SR, Wild JR, Raushel FM. Purification and properties of the phosphotriesterase from pseudomonas-diminuta. J Biol Chem 1989; 264: 19659-19665.
  • Chae MY, Postula JF, Raushel FM. Stereospecific enzymatic-hydrolysis of phosphorus-sulfur bonds in chiral organophosphate triesters. Bioorg Med Chem Lett 1994; 4: 1473-1478.
  • Yamazaki T, Yilmaz E, Mosbach K, Sode K. Towards the use of molecularly imprinted polymers containing imidazoles and bivalent metal complexes for the detection and degradation of organophosphotriester pesticides. Anal Chim Acta 2001; 435: 209-214.
  • Erdem M, Say R, Ersoz A, Denizli A, Turk H. Biomimicking, metal-chelating and surface-imprinted polymers for the degradation of pesticides. React Funct Polym 2010; 70: 238-243.
  • Hegg EL, Burstyn JN. Toward the development of metal-based synthetic nucleases and peptidases: a rationale and progress report in applying the principles of coordination chemistry. Coord Chem Rev 1998; 173: 133-165.
  • Courtney RC, Gustafson RL, Westerback SJ, Hyytiainen H, Chaberek SC, Martell AE. Metal chelate compounds as catalysts in the hydrolysis of isopropylmethylphosphonofluoridate and diisopropylphosphorofluoridate. J Am Chem Soc 1957; 79: 3030-3036.
  • Hartshorn CM, Deschamps JR, Singh A, Chang EL. Metal-chelator polymers as reactive adsorbents for organophosphate hydrolysis. React Funct Polym 2003; 55: 219-229.
  • Blacker NC, Findlay PH, Sherrington DC. Synthesis of Cu-II-complexed polymers and use as catalysts in the hydrolytic decontamination of Sarin nerve agent. Polym Advan Technol 2001; 12: 183-196.
  • Bukowski MR, Hile BL, Figurelli A, Hotham I, Maurer, MK. Insights into heterogeneous phosphodiester hydrolysis using a simple hydrogel-based copper(II)-imidazole catalyst. Inorg Chim Acta 2011; 370: 405-410.
  • Tafesse F. Hydrolysis of nerve agent simulants by synergistic effects of tetraminecobalt(III) and microemulsions. Inorg Chim Acta 1998; 269: 287-291.
Toplam 27 adet kaynakça vardır.

Ayrıntılar

Konular Mühendislik
Bölüm Araştırma Makalesi
Yazarlar

Murat Erdem

Yayımlanma Tarihi 30 Eylül 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 18 Sayı: 3

Kaynak Göster

APA Erdem, M. (2017). PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, 18(3), 720-732. https://doi.org/10.18038/aubtda.318087
AMA Erdem M. PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+. AUBTD-A. Eylül 2017;18(3):720-732. doi:10.18038/aubtda.318087
Chicago Erdem, Murat. “PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18, sy. 3 (Eylül 2017): 720-32. https://doi.org/10.18038/aubtda.318087.
EndNote Erdem M (01 Eylül 2017) PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18 3 720–732.
IEEE M. Erdem, “PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+”, AUBTD-A, c. 18, sy. 3, ss. 720–732, 2017, doi: 10.18038/aubtda.318087.
ISNAD Erdem, Murat. “PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering 18/3 (Eylül 2017), 720-732. https://doi.org/10.18038/aubtda.318087.
JAMA Erdem M. PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+. AUBTD-A. 2017;18:720–732.
MLA Erdem, Murat. “PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+”. Anadolu University Journal of Science and Technology A - Applied Sciences and Engineering, c. 18, sy. 3, 2017, ss. 720-32, doi:10.18038/aubtda.318087.
Vancouver Erdem M. PROMOTED HYDROLYSIS OF SOME ORGANOPHOSPHATE ESTERS USING SUPPORTED [Cu(tmen)OH(OH2)]+. AUBTD-A. 2017;18(3):720-32.