WO2000054881A1 - Ameliorations relatives a des agents complexants - Google Patents

Ameliorations relatives a des agents complexants Download PDF

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Publication number
WO2000054881A1
WO2000054881A1 PCT/GB2000/000962 GB0000962W WO0054881A1 WO 2000054881 A1 WO2000054881 A1 WO 2000054881A1 GB 0000962 W GB0000962 W GB 0000962W WO 0054881 A1 WO0054881 A1 WO 0054881A1
Authority
WO
WIPO (PCT)
Prior art keywords
complexant
anion
cation
binding site
crown
Prior art date
Application number
PCT/GB2000/000962
Other languages
English (en)
Inventor
James Darcy Mckinney
Paul Beer
Peter Hopkins
Original Assignee
British Nuclear Fuels Plc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by British Nuclear Fuels Plc filed Critical British Nuclear Fuels Plc
Priority to JP2000604946A priority Critical patent/JP2002539177A/ja
Priority to EP00907874A priority patent/EP1161299A1/fr
Priority to AU29336/00A priority patent/AU2933600A/en
Publication of WO2000054881A1 publication Critical patent/WO2000054881A1/fr

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/26—Treatment of water, waste water, or sewage by extraction
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/68—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water
    • C02F1/683—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water by addition of complex-forming compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
    • G—PHYSICS
    • G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
    • G21F—PROTECTION AGAINST X-RADIATION, GAMMA RADIATION, CORPUSCULAR RADIATION OR PARTICLE BOMBARDMENT; TREATING RADIOACTIVELY CONTAMINATED MATERIAL; DECONTAMINATION ARRANGEMENTS THEREFOR
    • G21F9/00—Treating radioactively contaminated material; Decontamination arrangements therefor
    • G21F9/04—Treating liquids
    • G21F9/06—Processing
    • G21F9/12—Processing by absorption; by adsorption; by ion-exchange
    • G21F9/125—Processing by absorption; by adsorption; by ion-exchange by solvent extraction

Definitions

  • the present invention relates to a complexant for compiexing an anion, particularly, but not exclusively, a pertechnetate anion.
  • the invention also relates to the extraction of an anion from a liquid medium, particularly, but not exclusively, it relates to the extraction of a pertechnetate anion.
  • a complexant for forming a complex with an anion having at least one cation binding site and, when said at least one cation binding site is occupied by a cation, at least one anion binding site.
  • the complexant may be selective for a particular anion, i.e. the complexant may preferentially complex the particular anion from a liquid medium containing a number of different anions.
  • the complexant may preferentially complex the particular anion from a liquid medium containing a number of different anions.
  • the complexant is effective for compiexing tetrahedral oxoanions for example, chro ate, Cr(-V ⁇ , pertechnetate, Tc0 4 " , perrhenate, ReCN and perchlorate.
  • the complexant is particularly effective for compiexing chromate, CrO.-N " and pertechnetate, Tc0 4 " .
  • the invention thus enables the selective complexation of pertechnetate and/or chromate.
  • the complexant has a plurality of cation binding sites and, when said cation binding sites are occupied by cations, at least one anion binding site.
  • the complexant has a plurality of cation binding sites, in use, preferably all cation binding sites are occupied by cations.
  • the complexant has a plurality of cation binding sites, typically the complexant has, when said cation binding sites are occupied by cations, one anion binding site.
  • the cation may come from the same liquid medium as the anion, thus making use of cations which may be co-present in the liquid medium for compiexing and/or extracting the anion.
  • the complexant is preferably multipodal, each leg providing a cation binding site.
  • leg means an elongate group capable of ligating the anion.
  • the complexant is preferably tripodal, i.e. comprising three legs .
  • the complex is preferably multidentate, each leg proving a coordination site for the anion.
  • the cation binding site preferably is located towards the outer end of the leg, the outer end being that end opposite to the end where the legs are joined. Most preferably the site is located at the outer end of the leg.
  • the multipodal structure typically defines a space or cavity between the legs and in the complex the anion may occupy the space or cavity defined, as shown schematically in Figure 3.
  • each leg further comprises a group which assists formation of the complex.
  • Preferred such groups include amino, ammonium, urea, thio urea, and guanidinium moieties.
  • the hydrogen may participate advantageously in hydrogen bonding to the anion, thus enhancing formation of the complex.
  • Reference herein to an amino group includes reference to a quaternary ammonium ion group.
  • x is 2.
  • all three groups Yi, Y 2 and Y 3 each comprise a crown ether group.
  • a more preferred complexant comprises C ? H 4 for R l f R 2 and R 3 and amidebenzo-15-crown-5 for Yi, Y 2 and Y 3 as shown in Figure 2.
  • the complexants shown in Figures 1 and 2 are especially effective selective for chromate and pertechnetate.
  • the cation may comprise sodium, potassium or caesium for example.
  • the cation binding site preferably comprises a crown ether.
  • crown ether includes crown ether derivatives, for example, amidebenzo crown ethers.
  • 15-crown-5 is preferred for binding sodium and 21-crown-7 is preferred for caesium.
  • the invention may provide a single method for extracting both TcCN and Cs + simultaneously from a waste stream.
  • the complexant is soluble in a wide range of organic solvents.
  • the solubility of the complexant in solvents such as odourless kerosene (OK) may be increased by the addition of hydrocarbon substituents to the complexant, for example to the crown ether groups .
  • a method of extracting an anion from a liquid medium comprising: providing a complexant according to the first aspect of the invention; causing at least one cation to occupy said at least one cation binding site; forming a complex between the resultant cation-bound complexant and the anion; and separating the complex from the liquid medium.
  • the method of extraction is effective for the extraction of tetrahedral oxoanions, for example chromate, Cr0 4 2" , pertechnetate, TcCN , perrhenate, ReCN and perchlorate.
  • the method is particularly effective for extracting chromate, Cr0 4 2" and pertechnetate, Tc0 4 " .
  • the cation may comprise sodium, potassium or caesium for example .
  • the cation may come from the same liquid medium, thus making use of cations which may be co-present in the liquid medium for extracting the anion.
  • the invention may provide, for example, a single method for extracting both Tc0 4 " and Cs + simultaneously from a waste stream.
  • Figure 1 shows a preferred complexant according to the present invention
  • Figure 2 shows a more preferred complexant according to the present invention
  • Figure 3 shows a schematic mechanism for anion extraction using the present invention
  • Figure 4 shows a reaction scheme for synthesising a complexant
  • Figure 5 shows a graph for technetium extraction using different concentrations of complexant
  • Figure 6 shows a schematic set-up for a liquid membrane experiment .
  • the compound tren is reacted with the carboxybenzo- crown compound 1 in the presence of S0C1 2 to form the complexant .
  • the amount of L in the organic phase varied between 1 and 10 equivalents w.r.t. pertechnetate. 2ml of each phase were shaken together at 20 deg C at 800rpm. 0.1ml samples of the aqueous phase were removed and made up to 1ml with water at lh, 2h and 24h. The final organic phase was separated from the aqueous layer and studied using 99Tc nmr.
  • An acceptor phase consisting of H0 was separated from a donor phase consisting of simulated waste as described in Example 2 by a glass divider. Communication of the two phases was through a liquid membrane of lxlOexp-3 M L in dichloromethane , where L is as defined above.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Hydrology & Water Resources (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • General Engineering & Computer Science (AREA)
  • High Energy & Nuclear Physics (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention porte sur un agent complexant qui permet de complexer un anion, et plus particulièrement mais sans exclusive un anion pertéchnétate. L'agent complexant comporte au moins un site de liaison cationique et, lorsque ce site de liaison cationique est occupé par un cation, au moins un site de liaison anionique. Cette invention concerne également l'extraction d'un anion dans un milieu liquide à l'aide dudit agent complexant.
PCT/GB2000/000962 1999-03-16 2000-03-15 Ameliorations relatives a des agents complexants WO2000054881A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2000604946A JP2002539177A (ja) 1999-03-16 2000-03-15 錯形成物質における改良
EP00907874A EP1161299A1 (fr) 1999-03-16 2000-03-15 Ameliorations relatives a des agents complexants
AU29336/00A AU2933600A (en) 1999-03-16 2000-03-15 Improvements in and relating to complexants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9905867.9A GB9905867D0 (en) 1999-03-16 1999-03-16 A method of anion extraction
GB9905867.9 1999-03-16

Publications (1)

Publication Number Publication Date
WO2000054881A1 true WO2000054881A1 (fr) 2000-09-21

Family

ID=10849609

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2000/000962 WO2000054881A1 (fr) 1999-03-16 2000-03-15 Ameliorations relatives a des agents complexants

Country Status (5)

Country Link
EP (1) EP1161299A1 (fr)
JP (1) JP2002539177A (fr)
AU (1) AU2933600A (fr)
GB (1) GB9905867D0 (fr)
WO (1) WO2000054881A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5028402A (en) * 1988-06-16 1991-07-02 Cogema Compagnie General Des Matieres Nucleaires Process for separating by means of crown ethers the uranium and plutonium present in an aqueous medium resulting from the reprocessing of irradiated nuclear fuels
US5405601A (en) * 1993-07-02 1995-04-11 Mallinckrodt Medical Inc. Functionalized tripodal ligands for imaging applications
US5443731A (en) * 1994-07-21 1995-08-22 The United States Of America As Represented By The United States Department Of Energy Process for extracting technetium from alkaline solutions
WO1997037995A1 (fr) * 1996-04-05 1997-10-16 Board Of Regents, The University Of Texas System Calixpyrroles, calixpyridinopyrroles et calixpyridines
WO1998039288A1 (fr) * 1997-03-07 1998-09-11 Nycomed Amersham Plc Imines polydentes et leurs complexes metalliques

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5028402A (en) * 1988-06-16 1991-07-02 Cogema Compagnie General Des Matieres Nucleaires Process for separating by means of crown ethers the uranium and plutonium present in an aqueous medium resulting from the reprocessing of irradiated nuclear fuels
US5405601A (en) * 1993-07-02 1995-04-11 Mallinckrodt Medical Inc. Functionalized tripodal ligands for imaging applications
US5443731A (en) * 1994-07-21 1995-08-22 The United States Of America As Represented By The United States Department Of Energy Process for extracting technetium from alkaline solutions
WO1997037995A1 (fr) * 1996-04-05 1997-10-16 Board Of Regents, The University Of Texas System Calixpyrroles, calixpyridinopyrroles et calixpyridines
WO1998039288A1 (fr) * 1997-03-07 1998-09-11 Nycomed Amersham Plc Imines polydentes et leurs complexes metalliques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
P.D. BEER: "The synthesis of novel schiff base bis- and tris-crown ether ligands containing recognition sites for alkali and transition metal guest cations", POLYHEDRON, vol. 7, no. 21, 1988, pages 2649 - 2653, XP000921403 *

Also Published As

Publication number Publication date
JP2002539177A (ja) 2002-11-19
AU2933600A (en) 2000-10-04
GB9905867D0 (en) 1999-05-05
EP1161299A1 (fr) 2001-12-12

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