Environmental chemistry of phosphonates

Water Research

Volumn 37, Issue 11, 2003, Pages 2533-2546

  Nowack, Bernd ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Adsorption; Chelating agents; Degradation; Heavy metals; Phosphonates; Speciation

Indexed keywords

CHELATION; COMPLEXATION; ENVIRONMENTAL ENGINEERING; PHOTODEGRADATION; WASTEWATER;

COMPLEXING AGENTS;

PHOSPHORUS COMPOUNDS;

1,2 DIAMINOETHANETETRAKIS(METHYLENEPHOSPHONIC ACID); CALCIUM DERIVATIVE; CHELATING AGENT; DIETHYLENETRIAMINEPENTAKIS(METHYLENEPHOSPHONIC ACID); ETIDRONIC ACID; FERRIC ION; INDUSTRIAL CHEMICAL; MAGNESIUM DERIVATIVE; MAGNESIUM ION; NITRILOTRIS(METHYLENEPHOSPHONIC ACID); OXYGEN; PHOSPHONIC ACID DERIVATIVE; PHOSPHONOBUTANE TRICARBOXYLIC ACID; UNCLASSIFIED DRUG;

CHELATION; HEAVY MEDIUM SUSPENSION; PHOSPHATE; WASTEWATER;

ADSORPTION; ANALYTIC METHOD; BIODEGRADATION; CONCENTRATION (PARAMETERS); DISSOLUTION; ENVIRONMENTAL IMPACT; MOLECULAR STABILITY; NONHUMAN; OXIDATION; PHOTODEGRADATION; PRECIPITATION; PRIORITY JOURNAL; REVIEW; SURFACE PROPERTY; WASTE WATER MANAGEMENT; WATER CONTAMINATION; WATER TREATMENT;

EID: 0038739203     PISSN: 00431354     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0043-1354(03)00079-4     Document Type: Review

References (115)

1. Means J.L., Alexander C.A. The environmental biogeochemistry of chelating agents and recommendations for the disposal of chelated radioactive wastes. Nucl Chem Waste Manage. 2:1981;183-196.
2. Wolf K, Gilbert PA. EDTA - Ethylenediaminetetraacetic acid. In: Hutzinger O (Ed.), The Handbook of Environmental Chemistry, vol. 3, Part F. Berlin, Heidelberg: Springer, 1992. p. 243-59.
3. Bucheli-Witschel M., Egli T. Environmental fate and microbial degradation of aminopolycarboxylic acids. FEMS Microbiol Rew. 25:2001;69-106.
4. Knepper T.P., Weil H. Study on the entry of synthetic chelating agents and compounds exhibiting complexing properties into the aquatic environment. Vom Wasser. 97:2001;193-232.
5. Nowack B. Environmental chemistry of aminopolycarboxylate chelating agents. Environ Sci Technol. 36:2002;4009-4016.
6. Gledhill WE, Feijtel TCJ. Environmental properties and safety assessment of organic phosphonates used for detergent and water treatment applications. In: Hutzinger O, editor. The handbook of environmental chemistry, vol. 3, Part F. Berlin, Heidelberg: Springer, 1992, pp. 261-85.
7. Jaworska J., van Genderen-takken H., Hanstveit A., van de Plasche E., Feijtel T. Environmental risk assessment of phosphonates, used in domestic laundry and cleaning agents in the Netherlands. Chemosphere. 47:2002;655-665.
8. Atkinson D. Toxicological properties of glyphosate - a summary. Atkinson D. The herbicide glyphosate. 1985;127-133 Butterworths, London.
9. Franz J.E., Mao M.K., Sikorski J.A. Glyphosate. a unique global herbicide ACS Monogr. 189:1997;653.
10. Stalikas C.D., Konidari C.N. Analytical methods to determine phosphonic and amino acid group-containing pesticides. J Chromatogr A. 907:2001;1-19.
11. de Klerk J.M.H., van Dijk A., van het Schip A.D., Zonnenberg B.A., van Rijk P.P. Pharmacokinetics of rhenium-186 after administration of rhenium-186-HEDP to patients with bone metastases. J Nucl Med. 33:1992;646-651.
12. Popov K., Rönkkömäki H., Lajunen L.H.J. Critical evaluation of stability constants of phosphonic acids. Pure Appl Chem. 73:2001;1641-1677.
13. Müller B. ChemEQL, 2.0 A program to calculate chemical speciation, equilibria, titrations, dissolution, precipitation, adsorption, simple kinetics, px-py diagrams. EAWAG/ ETH, 1996.
14. Fleisch H. Bisphosphonates. a new class of drugs in diseases of bone and calcium metabolism Recent Results Cancer Res. 116:1989;1-28.
15. May H.B., Nijs H., Godecharles V. Phosphonates. Multifunctional ingredients for laundry detergents. Household Pers Prod Ind. 23:1986;50-54.
16. Davenport B, DeBoo A, Dubois F, Kishi A. CEH report: chelating agents. SRI Consulting, Menlo Park, CA, USA, 2000.
17. van Hullebusch E., Chazal P.M., Deluchat V. Influence of phosphonic acids and EDTA on bacterial copper toxocity. Toxicol Environ Chem. 82:2002;75-91.
18. Huber L. Investigations about the biological degradability and fish toxicity of 2 organic chelating agents on phosphonic acid basis (ATMP and HEDP). Tenside Deterg. 12:1975;316-322.
19. Schöberl P.H. Ecologically relevant data of non-tenside components in washing and cleaning agents. Tenside Surfactants Deterg. 25:1988;99-107.
20. Steber J., Wierich P. Properties of hydroxyethane diphosphonate affecting its environmental fate. degradability, sludge adsorption, mobility in soils, and bioconcentration Chemosphere. 15:1986;929-945.
21. Steber J., Wierich P. Properties of aminotris(methylenephosphonate) affecting its environmental fate. degradability, sludge adsorption, mobility in soils, and bioconcentration Chemosphere. 16:1987;1323-1337.
22. Calvin G., Long P.H., Stitzel K.A., Anderson R.L., Balmbra R.R., Bruce R.D., Bhatt A., Miller P.M., Broadmeadow A. Ethyelenediaminetetra(methylenephosphonic acid) - genotoxicity, biodistribution, and subchronic toxicity in rats. Food Chem Toxicol. 26:1988;601-610.
23. Francis M.D., Centner R.L. The development of diphosphonates as significant health care products. J Chem Educ. 55:1978;760-766.
24. Weiss J., Hägele G. Ion-chromatographic analysis of inorganic and organic complexing agents. Fresenius Z Anal Chem. 328:1987;46-50.
25. Tschäbunin G., Fischer P., Schwedt G. On the analysis of polymethylenephosphonic acids. I. A systematic survey of the ion chromatography of organophosphonic acids. Fresenius Z Anal Chem. 333:1989;111-116.
26. Tschäbunin G., Fischer P., Schwedt G. On the analysis of polymethylenephosphonic acids. II. A systematic survey of post-column derivatization in ion chromatography. Fresenius Z Anal Chem. 333:1989;117-122.
27. Vaeth E., Sladek P., Kenar K. Ion chromatography of polyphosphates and phosphonates. Fresenius Z Anal Chem. 329:1987;584-589.
28. Tewari K.M.J., van Stroe-Bieze S.A.M. Analysis of amine-containing phosphonates in detergent powders by anion-exchange chromatography with pulsed amperometric detection. J Chromatogr A. 771:1997;155-161.
29. Thompson R., Grinberg N., Perpall H., Bicker G., Tway P. Separation of organophosphonates by ion chromatography with indirect photometric detection. J Liquid Chromatogr. 17:1994;2511-2531.
30. Shamsi S.A., Danielson N.D. Ribonucleotide electrolytes for capillary electrophoresis of polyphosphates and polyphosphonates with indirect photometric detection. Anal Chem. 67:1995;1845-1852.
31. Klinger J., Sacher F., Brauch H-.J., Maier D. Determination of organic phosphonates in aqueous samples using liquid chromatography/ particle-beam mass spectrometry. Acta Hydrochim Hydrobiol. 25:1997;79-86.
32. Nowack B. Determination of phosphonates in natural waters by ion-pair high performance liquid chromatography. J Chromatogr A. 773:1997;139-146.
33. Nowack B., Stone A.T. Degradation of Nitrilotris(methylenephosphonic acid) and related (amino)phosphonate chelating agents in the presence of manganese and molecular oxygen. Environ Sci Technol. 34:2000;4759-4765.
34. Nowack B. Determination of phosphonic acid breakdown products by high performance liquid chromatography after derivatization. J Chromatogr A. 942:2002;185-190.
35. Ammann A.A. Determination of strong binding chelators and their metal complexes by anion-exchange chromatography and inductively coupled plasma mass spectrometry. J Chromatogr A. 947:2002;205-216.
36. Ammann A.A. Speciation of heavy metals in environmental water by ion chromatography coupled to ICP-MS. Anal Bioanal Chem. 372:2002;448-452.
37. Frigge E., Jackwerth E. Preconcentration and determination of organophosphonic acids. application to natural waters Anal Chim Acta. 254:1991;63-73.
38. Nowack B. Behavior of phosphonates in wastewater treatment plants of Switzerland. Water Res. 32:1998;1271-1279.
39. Nowack B. Aminopolyphosphonate removal during wastewater treatment. Water Res. 36:2002;4636-4642.
40. Stone AT, Knight MA, Nowack B. Speciation and chemical reactions of phosphonate chelating agents in aqueous media. In: Lipnick RL, Mason RP, Phillips ML, Pittman CU, editors. Chemicals in the environment: fate, impacts and remediation, ACS Symposium Series No. 806. Washington, DC: American Chemical Society, 2001. p. 59-94.
41. Xyla A.G., Mikroyannidis J., Koutsoukos P.G. The inhibition of calcium carbonate precipitation in aqueous media by organophosphorous compounds. J Colloid Interface Sci. 153:1992;537-551.
42. Fischer K. Sorption of chelating agents (HEDP and NTA) onto mineral phases and sediments in aquatic model systems, Part I. sorption onto clay minerals Chemosphere. 22:1991;15-27.
43. Morillo E., Undabeytia T., Maqueda C. Adsorption of glyphosate on the clay mineral montmorillonite. effect of Cu(II) in solution and adsorbed on the mineral Environ Sci Technol. 31:1997;3588-3592.
44. 3/water interface. J Colloid Interface Sci. 175:1995;230-238.
45. Laiti E., Öhmann L-.O. Acid/ base properties and phenylphosphonic acid complexation at the boehmite/ water interface. J Colloid Interface Sci. 183:1996;441-452.
46. Liu Y., Yu L., Guo J. Adsorption of PBTCA on alumina surfaces and its influence on the fractal characteristics of sediments. J Colloid Interface Sci. 227:2000;164-170.
47. Day G.M., Hart B.T., McKelvie I.D., Beckett R. Influence of natural organic matter on the sorption of biocides onto goethite, II. Glyphosate. Environ Technol. 18:1997;781-794.
48. Nowack B., Stone A.T. Adsorption of phosphonates onto the goethite-water interface. J Colloid Interface Sci. 214:1999;20-30.
49. Nowack B., Stone A.T. Influence of metals on the adsorption of phosphonates onto goethite. Environ Sci Technol. 3:1999;3627-3633.
50. Jung A., Bisaz S., Fleisch H. The binding of pyrophosphate and two diphosphonates by hydroxyapatite crystals. Calcif Tissue Res. 11:1973;269-280.
51. 153Sm-EDTMP on calcium hydroxyapatite. Int J Radiat Appl Instrum Part A. 39:1988;495-499.
52. Black S.N., Bromley L.A., Davey R.J., Dobbs B., Rout J.E. Interactions at the organic/inorganic interface. binding motifs for phosphonates at the surface of barite crystals J Chem Soc Faraday Trans. 87:1991;3409-3414.
53. Horstmann B., Grohmann A. Investigations into the biodegradability of phosphonates. Vom Wasser. 70:1988;163-178.
54. Fischer K. Sorption of chelating agents (HEDP and NTA) onto mineral phases and sediments in aquatic model systems. Part II: Sorption onto sediments and sewage sludges. Chemosphere. 24:1992;51-62.
55. Held S. Th environmental behavior of chelating agents on phosphomic acid basis. Textilveredlung. 24:1989;394-398.
56. Nowack B., Lützenkirchen J., Behra P., Sigg L. Modeling the adsorption of metal-EDTA complexes onto oxides. Environ Sci Technol. 30:1996;2397-2405.
57. Stumm W. Reactivity at the mineral-water interface. dissolution and inhibition Colloids Surf A. 120:1997;143-166.
58. Davis J.A., Kent D.B., Rea B.A., Maest A.S., Garabedian S.P. Influence of redox environment and aqueous speciation on metal transport in groundwater. Brown D.S. 1993;223-273 Lewis Publishers, editor, Metals in groundwater. Boca Raton.
59. Jardine P.M., Jacobs G.K., O'Dell J.D. Unsaturated transport processes in undisturbed heterogeneous porous media. II. Co-contaminants Soil Sci Soc Am J. 57:1993;954-962.
60. 3 and remobilization of heavy metals. results from laboratory experiments and field trials Vom Wasser. 63:1984;63-78.
61. Bordas F., Bourg A.C.M. Effect of complexing agents (EDTA and ATMP) on the remobilization of heavy metals from a polluted river sediment. Aquat Geochem. 4:1998;201-214.
62. Lacour S., Deluchat V., Bollinger J.C., Serpaud B. Complexation of trivalent cations (Al(III), Cr(III), Fe(III)) with two phosphonic acids in the pH range of fresh waters. Talanta. 46:1998;999-1009.
63. Müller G., Förstner U. Experimental mobilization of copper and zinc from aquatic sediments by some polyphosphate substitutes in detergents. Z Wasser Abwasser Forsch. 9:1976;150-152.
64. Browning F.H., Fogler H.S. Effect of synthesis parameters on the properties of calcium phosphonate precipitates. Langmuir. 11:1995;4143-4152.
65. Gerbino AJ.Quantifying the retention, release of polyphosphonates in oil and gas producing formations using surface complexation and precipitation theory. Dissertation, Rice University, Texas, 1996.
66. Samakaev R.K., Dyatlova N.M., Dytyuk L.T. The solubility in water of the nitrilotrimethylenephosphonates of the group II elements. Russ J Inorg Chem. 29:1984;1819-1820.
67. Oddo J.E., Tomson M.B. The solubility and stoichiometry of calcium-diethylenetriaminepenta(methylene phosphonate) at 70°C in brine solutions at 4.7 and 5.0 pH. Appl Geochem. 5:1990;527-532.
68. Kan A.T., Oddo J.E., Tomson M.B. Formation of two calcium diethylenetriaminepentakis(methylene phosphonic acid) precipitates and their physical chemical properties. Langmuir. 10:1994;1450-1455.
69. Pairat R., Sumeath C., Browning F.H., Fogler H.S. Precipitation and dissolution of calcium-ATMP precipitates for the inhibition of scale formation in porous media. Langmuir. 13(1):1997;791-1798.
70. Browning F.H., Fogler H.S. Effect of precipitating conditions on the formation of calcium-HEDP precipitates. Langmuir. 12:1996;5231-5238.
71. Friedfeld S.J., He S., Tomson M.B. The temperature and ionic strength dependence of the solubility product constant of ferrous phosphonate. Langmuir. 14:1998;3698-3703.
72. Zholnin A.V., Zudov V.G., Leitsin V.A., Nosova R.L., Smirnov E.N. Preparation of the iron complex of nitrilotrimethylenephosphonic acid from zinc-production wastes. J Appl Chem USSR. 63:1990;751-754.
73. Deluchat V., Serpaud B., Caullet C., Bollinger J-.C. Protonation and complexation constants of 1-hydroxyethane-1,1′-diphosphonic acid (HEDP) with divalent cations. a study of insoluble complexes of HEDP with Pb(II) and Cd(II) Phosphorous Sulfur Silicon. 104:1995;81-92.
74. Gratz A.J., Hillner P.E. Poisoning of calcite growth viewed in the atomic force microscope (AFM). J Cryst Growth. 129:1993;789-793.
75. Gal J-.Y., Bollinger J.C., Tolosa H., Gache N. Calcium carbonate solubility. a reappraisal of scale formation and inhibition Talanta. 43:1996;497-1509.
76. Benton W.J., Collins I.R., Grimsey I.M., Parkinson G.M., Rodger S.A. Nucleation, growth and inhibition of barium sulfate-controlled modification with organic and inorganic additives. Faraday Discuss. 95:1993;281-297.
77. Davis R.V., Carter P.W., Kamrath M.A., Johnson D.A., Reed P.E. The use of modern methods in the development of calcium carbonate inhibitors for cooling water systems. Amjad Z. Mineral scale formation and inhibition. 1995;33-46 Plenum Press, New York.
78. Zieba A., Stehuraman G., Perez F., Nancollas G.H., Cameron D. Influence of organic phosphonates on hydroxyapatite crystal growth kinetics. Langmuir. 12:1996;2853-2858.
79. Horstmann B., Grohmann A. The influence of phosphonates on phosphate elimination. Part 1. 1-hydroxyethane-1,1-diphosphonic acid (HEDP) Z Wasser Abwasser Forsch. 17:1984;177-181.
80. Horstmann B., Grohmann A. The influence of phosphonates on phosphate elimination. Part 2. 2-phosphono-butane-1,2,4-tricarbonic acid (PBTC), aminotri(methylenephosphonic acid) (ATMP) and ethylenediamintetra(methylenephosphonic acid) (EDTMP) Z Wasser Abwasser Forsch. 19:1986;236-240.
81. Huang J., Chen R. An overview of recent advances on the synthesis and biological activity of α-aminophosphonic acid derivatives. Heteroatom Chem. 11:2000;480-492.
82. Horiguchi M., Kandatsu M. Isolation of 2-aminoethane phosphonic acid from rumen protozoa. Nature. 184:1959;901-902.
83. Wanner B.L. Molecular genetics of carbon-phosphorous bond cleavage in bacteria. Biodegradation. 5:1994;175-184.
84. McMullan G., Quinn J.P. The utilization of aminoalkylphosphonic acids as sole nitrogen source by an environmental bacterial isolate. Lett Appl Microbiol. 17:1993;135-138.
85. Schowanek D., Verstraete W. Phosphonate utilization by bacterial cutures and enrichments from environmental samples. Appl Environ Microbiol. 56:1990;895-903.
86. Raschke H., Rast H-.G., Kleinstück R., Sicius H., Wischer D. Utilization of 2-phosphonobutane-1,2,3-tricarboxylic acid as source of phosphorous by environmental bacterial isolates. Chemosphere. 29:1994;81-88.
87. Schowanek D., Verstraete W. Phosphonate utilization by bactaria in the presence of alternative phosphorous sources. Biodegradation. 1:1990;45-53.
88. Bolton H., Girvin D.C. Effect of adsorption on the biodegradation of nitrilotriacetate by Chelatobacter heintzii. Environ Sci Technol. 30:1996;2057-2065.
89. Zaranyika M.F., Nyandoro M.G. Degradation of glyphosate in the aquatic environment. an enzymatic kinetic model that takes into account microbial degradation of both free and coloidal (or sediment) particle adsorbed glyphosate J Agric Food Chem. 41:1993;838-842.
90. Nörtemann B. Biodegradation of EDTA. Appl Microbiol Biotechnol. 51:1999;751-759.
91. Kari F.G., Giger W. Modeling the photochemical degradation of EDTA in the River Glatt. Environ Sci Technol. 29:1995;2814-2827.
92. Fischer K. Distribution and elimination of HEDP in aquatic test systems. Water Res. 27:1993;85-493.
93. Matthijs E., De Oude N.T., Bolte M., Lemaire J. Photodegradation of ferric ethylenediaminetetra(methylenephosphonic acid) (EDTMP) in aqueous solution. Water Res. 23:1989;845-851.
94. Lockhart H.B., Blakeley R.V. Aerobic photodegradation of X(N) chelates of ethylenedinitrilotetraacetate (EDTA). implications for natural waters Environ Lett. 9:1975;19-31.
95. Nowack B., Baumann U. Biodegradation of the photolysis products of Fe(III)EDTA. Acta Hydrochim Hydrobiol. 26:1998;104-108.
96. Martell A.E., Motekaitis R.J., Fried A.R., Wilson J.S., MacMillan D.T. Thermal decomposition of EDTA, NTA, and nitrilotrimethylenephosphonic acid in aqueous solution. Can J Chem. 53:1975;3471-3476.
97. Kaslina N.A., Polyakova I.A., Kessenikh A.V., Zhadanov B.V., Rudomino M.V., Churilina N.V., Kabachnik M.I. Thermal decomposition of nitrilotrimethylenephosphonic acid in aqueous solution. J Gen Chem USSR. 55:1985;472-475.
98. Tschäbunin G., Fischer P., Schwedt G. On the analysis of polymethylenephosphonic acids. III. Stability of ethylenediaminetetramethylenephosphonic acod (EDTMP) in aqueous solution. Fresenius Z Anal Chem. 333:1989;123-128.
99. Schowanek D., Verstraete W. Hydrolysis and free radical mediated degradation of phosphonates. J Environ Qual. 20:1991;769-776.
100. Nowack B., Stone A.T. Heterogeneous and homogeneous oxidation of nitrilotrismethylenephoshonate (NTMP) in the presence of oxygen and manganese (II, III). J Phys Chem B. 106:2002;6227-6233.
101. Klinger J., Sacher F., Brauch H.J., Maier D., Worch E. Behavior of phosphonic acids during drinking water treatment. Vom Wasser. 91:1998;15-27.
102. Gilbert E., Hoffmann-Glewe S. Ozonation of ethylenediaminetetraacetate (EDTA) in aqueous solution, influence of pH value and metal ions. Water Res. 24:1990;39-44.
103. Klinger J., Lang M., Sacher F., Brauch H.J., Maier D., Worch E. Formation of glyphosate and AMPA during ozonation of waters containing ethylenediaminetetra(methylenephosphonic acid). Ozone Sci Eng. 20:1998;99-110.
104. Deluchat V., Bollinger J.C., Serpaud B., Caullet C. Divalent cations speciation with three phosphonate ligands in the pH-range of natural waters. Talanta. 44:1997;897-907.
105. Lacour S., Deluchat V., Bollinger J.C., Serpaud B. Influence of carbonate and calcium ions on the phosphonate complexation with Cu, Zn, Cd and Ni in fresh waters. an evaluation of thermodynamic constants and a chemical model Environ Technol. 20:1999;249-257.
106. Margerum D.W. Exchange reactions of multidentate ligand complexes. Rec Chem Prog. 24:1963;237-251.
107. Xue H.B., Sigg L., Kari F.G. Speciation of EDTA in natural waters. exchange kinetics of FeEDTA in river water Environ Sci Technol. 29:1995;59-68.
108. Deluchat-Antony V., Bollinger J.C., Serpaud B., Caullet C. Influence of some washing powder components on copper(II) and calcium(II) complexation with fulvic acids. Int J Environ Anal Chem. 68:1998;123-135.
109. Sigg L., Xue H.B. Metal speciation. concepts, analysis and effects Stumm W. Chemistry of aquatic systems: local and global perspectives. 1994;153-181 ECSC, EEC, EAEC, Brussels, Luxembourg.
110. Nowack B., Xue H.B., Sigg L. Influence of natural and anthropogenic ligands on metal transport during infiltration of river water to groundwater. Environ Sci Technol. 31:1997;866-872.
111. Rizkalla E.N. Metal chelates of phosphonate-containing ligands. Rev Inorg Chem. 5:1983;223-304.
112. Nowack B., Kari F.G., Hilger S.U., Sigg L. Determination of adsorbed and dissolved EDTA-species in natural waters. Anal Chem. 68:1996;561-566.
113. Nirel P.M., Pardo P.E., Landry J.C., Revaclier R. Method for EDTA speciation determination. application to sewage treatment plant effluents Water Res. 32:1998;3615-3620.
114. Bedsworth W.W., Sedlak D.L. Determination of metal complexes of ethylenediaminetetraacetate in the presence of organic matter by high-performance liquid chromatography. J Chromatogr A. 905:2001;157-162.
115. Metzner G. Behavior of organic chelating agents on phosphonic acid basis in wastewater treatment plants. Beitr Abwasser Fisch Flussbiol. 44:1990;323-336.