WO2009109754A1 - Procédé de nettoyage - Google Patents

Procédé de nettoyage Download PDF

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Publication number
WO2009109754A1
WO2009109754A1 PCT/GB2009/000602 GB2009000602W WO2009109754A1 WO 2009109754 A1 WO2009109754 A1 WO 2009109754A1 GB 2009000602 W GB2009000602 W GB 2009000602W WO 2009109754 A1 WO2009109754 A1 WO 2009109754A1
Authority
WO
WIPO (PCT)
Prior art keywords
perfluorinated
solvent
phosphine
metal
integer
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/GB2009/000602
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English (en)
Inventor
Robert James Baker
Helen Victoria Ogilvie
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nottingham Trent University
Original Assignee
Nottingham Trent University
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 Nottingham Trent University filed Critical Nottingham Trent University
Publication of WO2009109754A1 publication Critical patent/WO2009109754A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • G21F9/28—Treating solids
    • G21F9/30—Processing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0203—Solvent extraction of solids with a supercritical fluid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B08—CLEANING
    • B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
    • B08B7/00—Cleaning by methods not provided for in a single other subclass or a single group in this subclass
    • B08B7/0021—Cleaning by methods not provided for in a single other subclass or a single group in this subclass by liquid gases or supercritical fluids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B09—DISPOSAL OF SOLID WASTE; RECLAMATION OF CONTAMINATED SOIL
    • B09C—RECLAMATION OF CONTAMINATED SOIL
    • B09C1/00—Reclamation of contaminated soil
    • B09C1/02—Extraction using liquids, e.g. washing, leaching, flotation
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/36—Organic compounds containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
    • C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
    • C22B3/26—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds
    • C22B3/40—Mixtures
    • C22B3/408—Mixtures using a mixture of phosphorus-based acid derivatives of different types
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B7/00—Working up raw materials other than ores, e.g. scrap, to produce non-ferrous metals and compounds thereof; Methods of a general interest or applied to the winning of more than two metals
    • C22B7/006—Wet processes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06F—LAUNDERING, DRYING, IRONING, PRESSING OR FOLDING TEXTILE ARTICLES
    • D06F43/00—Dry-cleaning apparatus or methods using volatile solvents
    • D06F43/007—Dry cleaning methods
    • 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
    • G21F9/28—Treating solids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/12—Soft surfaces, e.g. textile
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/20—Industrial or commercial equipment, e.g. reactors, tubes or engines
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P10/00—Technologies related to metal processing
    • Y02P10/20—Recycling

Definitions

  • the invention relates to methods for extracting metals, for example metal contaminants, comprising the use of a liquid solvent or supercritical solvent, in combination with a perfluorinated phosphine.
  • the invention also relates to the combination of a supercritical solvent with a perfluorinated phosphine, and to novel and inventive perfluorinated phosphines.
  • Heavy metal contamination is a more conventional problem faced by many areas of the UK, especially those that have been heavily industrialised in the past but where these industries have moved on or closed down.
  • production of household batteries has left a serious contamination issue of toxic metals such as mercury, cadmium and lead for brown field sites across the UK, which hampers regeneration of the land.
  • toxic metals such as mercury, cadmium and lead for brown field sites across the UK, which hampers regeneration of the land. 5
  • the mean concentration of cadmium in industrial herbage was more than three times that found in urban or rural herbage 6 - this can constitute a pathway into the food chain.
  • a further concern for potential cadmium contamination is that mobile phone batteries contain cadmium, and there are ca. IS million mobile phones discarded every year into landfill sites in the UK, although new WEEE regulations will probably reduce this risk.
  • Chromium contamination is another area of concern and this can arise from such diverse manufacturing processes as the production of photocopy machines to chrome-plating to textile dyes. In the United States, chromium is present in two thirds of the 1,591 sites that are on the National Cleanup Priority list (as of2001). 8
  • Such prior processes have utilised, for example, trialkyl phosphate, triaryl phosphate, trialkylphosphine oxide, triarylphosphine oxide, beta-diketones to chelate metal contaminants.
  • chelators having improved properties. For example, a number of the chelators have selectivity for heavy metals, allowing heavy metals to be selectively removed. This means that problem contaminants, such as mercury, may be selectively removed from, for example soil, whilst still leaving useful metals, such as calcium or magnesium, in the soil.
  • JP 2000087013 discloses phosphate ester containing water and oil repellent compositions utilising a perfiuorinated phosphine oxide.
  • JP 11343416 similarly discloses perfluoroalkyl phosphate ester salts, which are used to treat silicone resin powders in the production of cosmetics.
  • Perfiuorinated alkyl phosphates have also been used to disperse metallic metal powder in magnetic paint (JP 62250937).
  • the invention provides a method for extracting a metal comprising exposing a metal- containing material to (i) a liquid solvent or supercritical solvent, in combination with (ii) a perfiuorinated phosphine.
  • the perfiuorinated phosphine acts as a chelator and binds to one or more metals within the material to remove it from the material.
  • the phosphine is particularly useful for use in combination with a supercritical solvent, such as carbon dioxide.
  • supercritical solvents are solvents that are at temperatures and pressures beyond their critical points.
  • the critical pressure of a substance is the highest pressure at which the substance can exist as a true liquid, no matter what the temperature.
  • gases at supercritical conditions are nearly as dense as some liquids due to the extreme temperature and pressure. This makes these gases ideal as solvents.
  • Carbon dioxide is especially useful as a supercritical fluid. The reason for the popularity of carbon dioxide is that it has critical points as low as approximately 31 0 C and 74 bar.
  • other solvents, including other supercritical solvents could also be used.
  • water can also act as a supercritical solvent, though at much higher temperatures (37.4°C and 222.3 bar).
  • Other supercritical solvents include xenon and ethane.
  • the phosphine may also be useful with more conventional organic and inorganic solvents, such as water or alcohols.
  • Organohalides for example alkyl halides and alkyl furans, such as chloro- or fluoro-forms may also be used.
  • Preferred solvents include dichloromethane, and perfluorinated organohalide solvents, such as perfluorohexane, perfluorocyclohexane, perfluoro(butyltetrahydroruran) or perfluoro- methylcyclohexane. Liquid (sub-critical) CO 2 may also be used.
  • Such solvents are generally known in the art
  • Perfluorinated solvents have many similar properties to many supercritical solvents such as ScCO 2 . For example they have low polarity compared to many solvents such as water or ionic liquids . They also have relatively high volatility compared to many solvents. See for example Clark LH & Tavener S.T. Org. Process. Res. Dev (2007), VoI 11, 149-155. Phosphine complexes have been previously demonstrated have similar solubility in fluorous and ScCO 2 solvents (Stribany R. T. and Gorun S.M. J Organometal. Chem. (1999), VoI 579, 217-221.
  • supercritical solvents are especially useful because they can be readily removed from the phosphine (for example when bound to metal), via evaporation. The evaporated supercritical solvent can then be recycled for re-use.
  • the perfluorinated phosphine is a perfluorinated phosphine oxide or perfluorinated phosphine sulphide.
  • the perfluorinated phosphine has a general formula: I, II or HI;
  • each of groups Rl, R2, R3, R4, R5, R6, R7, R8, R9 and RlO are independently selectable and are branched, straight or cyclic fluorocarbon groups, optionally comprising one or more alkyl moieties, preferably having the general formula CF 3 (CF2) ⁇ (CH2)ni, wherein one or more adjacent groups may be joined to form one or more rings where;
  • n is preferably 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. Most preferably m may be 2 or 3.
  • n maybe any integer from 0-20, but is most preferably 3, 5, 7, 9 or 11, or 7 or less, or 5 or less.
  • each of Rl, R3 and R2; R4, R5, R6 and R7; and R8, R9 and RlO are the same.
  • Two or more adjacent groups may form a ring, such as CsFn or two fused rings, such
  • X is preferably oxygen or sulphur, most preferably oxygen.
  • the compound may have a formula I
  • the compound may have a formula II, where n is 7 or less and X is O
  • phosphine sulphides (for example those shown in equation 5 below) have been found to be especially selective for the extraction of mercury and cadmium.
  • Y may be any suitable linker group. However it is preferably an alkyl, especially a straight chain alkyl. Preferably the alkyl contains between 1 and 6 carbon atoms, most preferably 2 carbon atoms.
  • the method may also comprise exposing the metal containing material to an oxidising agent, such as a mineral acid or nitric acid. Exposing the material to an oxidising agent may help to release contaminating metal from the material.
  • an oxidising agent such as a mineral acid or nitric acid. Exposing the material to an oxidising agent may help to release contaminating metal from the material.
  • the metal containing material is selected from soil or other contaminated material. It also includes laboratory waste, such as clothing or other waste, and includes the cleansing of laboratory utensils such as laboratory equipment and surfaces.
  • the metal is selected from one or more of cadmium, strontium, plutonium, uranium, lead, mercury, chromium, arsenic, antimony, tellurium, polonium, germanium and salts thereof.
  • the method preferably includes separating the solvent from the perfluorinated phosphine and recycling the solvent.
  • the metal-perfluorinated phosphine complex left may then be cleaned, for example by the treatment with an acid, to leave cleaned perfluorinated phosphine for re-use, and recovered metal, for example in the form of a metal salt.
  • Metal salt may then be disposed of or re-used for other purposes.
  • a second aspect of the invention also provides the combination of (i) a supercritical solvent and (ii) a perfluorinated phosphine.
  • the perfluorinated phosphine and/or the supercritical solvent is preferably as defined according to any of the first aspect of the invention.
  • the combination is preferably coordinated to a metal selected from one or more of cadmium, strontium, plutonium, uranium, lead, mercury chromium, arsenic, antimony, tellurium, polonium, germanium and salts thereof.
  • Further aspect of the invention provides a perfluorinated phosphine selected from:
  • the perfluorinated phosphine is utilised in the method according to the first aspect of the invention or is used in combination with the supercritical solvent according to the second aspect of the invention.
  • Figure 2 shows a summary of the different methods that may be used to produce examples of the phosphine ligands that may be used in the invention.
  • Rf refers to a perfluorine group, such as CF 3 (CF2)n, where n is an integer of 1-20, for example as defined above.
  • Figure 3 shows (a) UV/vis spectra of the compound, uranyl acetate and the uranyl complex; (b) IR spectrum of the ligand and the uranyl complex.
  • Figure 4 shows that plot of the absorbance at 352nm vs ligand concentration.
  • Figure 5 shows 31 P MMR spectra of (a) lead nitrate (b) Bu 2 Sn(OMe) 2 in CD 3 OD.
  • the radioisotopes 90 Sr(NO 3 I 2 and 133 Ba(NOs) 2 were purchased from Amersham International, Uranyl Nitrate from BDH and 59 FeCl 3 from Perkin Elmer. FC-72 was obtained from Acota and distilled before use. All other materials were obtained from Aldrich and used as received.
  • NMR spectra were recorded on a JEOL ECX-400 at 399.7 MHz ( 1 H) 5 376.1 MHz ( 19 F), 161.8 MHz ( 31 P) and 100.50 MHz ( 13 C).
  • Infrared spectra were recorded on a Perkin Elmer Spectrum 100 with ATR.
  • UV- vis spectra were recorded on a Perkin Elmer Lambda 25 spectrometer.
  • DSC spectra were recorded on a Perkin Elmer Diamond DSC.
  • ICP-OES measurements were recorded on a Perkin Elmer Optima 2100 DV spectrometer; calibration standards were purchased from Acres Organics and used as received.
  • Gamma analysis was performed on a Canberra Packard Cobra Auto-Gamma well type gamma counter.
  • the metal solution was placed in a sample vial and made up to 5 cm 3 with a buffer solution.
  • the required amount of extractant was dissolved in S cm 3 of FC-72 and added to the metal solutions.
  • the mixture was vigorously stirred for 30 minutes at 25 0 C, and the phases allowed to separate.
  • An aliquot (1 cm 3 ) of each layer was transferred to a polypropylene tube and counted for ⁇ activity.
  • strontium and uranium experiments an aliquot of each layer (1 cm 3 ) was transferred to a scintillation vial, diluted with scintillation cocktail (5 cm 3 ) and counted for ⁇ and ⁇ activities respectively.
  • a stock solution of uranyl nitrate was diluted to 5 cm 3 using distilled water to give 0.02g uranyl nitrate.
  • the required amount of the ligand was dissolved in freshly distilled perfluoromethylcyclohexane (5 cm 3 ) and the two solvents mixed. The biphasic mixture was vigorously stirred for 30 minutes then the two layers separated. 1 cm 3 of each sample was transferred to a cuvette and the uv-vis spectrum recorded.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Environmental & Geological Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Metallurgy (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Geology (AREA)
  • Physics & Mathematics (AREA)
  • General Engineering & Computer Science (AREA)
  • High Energy & Nuclear Physics (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Textile Engineering (AREA)
  • Soil Sciences (AREA)

Abstract

L'invention porte sur un procédé d'extraction d'un métal comprenant l'exposition d'une matière contenant un métal à (i) un solvant liquide ou un solvant supercritique ; en combinaison avec (ii) une phosphine perfluorée. L'invention porte également sur les phosphines perfluorées.
PCT/GB2009/000602 2008-03-04 2009-03-04 Procédé de nettoyage Ceased WO2009109754A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0804055A GB0804055D0 (en) 2008-03-04 2008-03-04 Cleaning method
GB0804055.2 2008-03-04

Publications (1)

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WO2009109754A1 true WO2009109754A1 (fr) 2009-09-11

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10167202B2 (en) 2016-02-23 2019-01-01 King Abdullah University Of Science And Technology Enhanced metal recovery through oxidation in liquid and/or supercritical carbon dioxide
US20230220514A1 (en) * 2022-01-07 2023-07-13 The Trustees Of Columbia University In The City Of New York Systems and methods for hydrometallurgical, anti-solvent, and electrochemical recovery of metals from wastes and ashes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998004754A1 (fr) * 1996-07-26 1998-02-05 Idaho Research Foundation, Inc. Procede et appareil pour l'extraction inversee de chelates
WO1999038820A1 (fr) * 1998-01-28 1999-08-05 Cambridge University Technical Services Limited Utilisation de co2 comprime dans des reactions chimiques
WO2006113621A2 (fr) * 2005-04-15 2006-10-26 Advanced Technology Materials, Inc. Formulations pour le nettoyage de couches de photoresine implantees d'ions a partir de dispositifs microelectroniques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998004754A1 (fr) * 1996-07-26 1998-02-05 Idaho Research Foundation, Inc. Procede et appareil pour l'extraction inversee de chelates
WO1999038820A1 (fr) * 1998-01-28 1999-08-05 Cambridge University Technical Services Limited Utilisation de co2 comprime dans des reactions chimiques
WO2006113621A2 (fr) * 2005-04-15 2006-10-26 Advanced Technology Materials, Inc. Formulations pour le nettoyage de couches de photoresine implantees d'ions a partir de dispositifs microelectroniques

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10167202B2 (en) 2016-02-23 2019-01-01 King Abdullah University Of Science And Technology Enhanced metal recovery through oxidation in liquid and/or supercritical carbon dioxide
US20230220514A1 (en) * 2022-01-07 2023-07-13 The Trustees Of Columbia University In The City Of New York Systems and methods for hydrometallurgical, anti-solvent, and electrochemical recovery of metals from wastes and ashes

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