CN113801063A - 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt or iron salt and preparation and application thereof - Google Patents
1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt or iron salt and preparation and application thereof Download PDFInfo
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- CN113801063A CN113801063A CN202110994981.6A CN202110994981A CN113801063A CN 113801063 A CN113801063 A CN 113801063A CN 202110994981 A CN202110994981 A CN 202110994981A CN 113801063 A CN113801063 A CN 113801063A
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- carboxyperoxybenzyl
- methylimidazole
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- -1 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt Chemical class 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 150000002505 iron Chemical class 0.000 title abstract description 4
- 239000002608 ionic liquid Substances 0.000 claims abstract description 44
- 229910000510 noble metal Inorganic materials 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 17
- 239000002184 metal Substances 0.000 claims abstract description 17
- 238000002386 leaching Methods 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 238000010438 heat treatment Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 16
- 239000010931 gold Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 14
- 229910052737 gold Inorganic materials 0.000 claims description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000008367 deionised water Substances 0.000 claims description 9
- 229910021641 deionized water Inorganic materials 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 239000003444 phase transfer catalyst Substances 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical class ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims description 5
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 5
- OITNBJHJJGMFBN-UHFFFAOYSA-N 4-(chloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CCl)C=C1 OITNBJHJJGMFBN-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- DCLQPXZJPAOMOL-UHFFFAOYSA-N 4-[(3-methylimidazol-3-ium-1-yl)methyl]benzoic acid chloride Chemical compound [Cl-].C(=O)(O)C1=CC=C(C[N+]2=CN(C=C2)C)C=C1 DCLQPXZJPAOMOL-UHFFFAOYSA-N 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- 238000007790 scraping Methods 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- WTEPWWCRWNCUNA-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 WTEPWWCRWNCUNA-UHFFFAOYSA-M 0.000 claims description 2
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 claims description 2
- 150000003841 chloride salts Chemical class 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- QLPMKRZYJPNIRP-UHFFFAOYSA-M methyl(trioctyl)azanium;bromide Chemical compound [Br-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC QLPMKRZYJPNIRP-UHFFFAOYSA-M 0.000 claims description 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 claims description 2
- QRPRIOOKPZSVFN-UHFFFAOYSA-M methyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 QRPRIOOKPZSVFN-UHFFFAOYSA-M 0.000 claims description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000005272 metallurgy Methods 0.000 abstract description 5
- 231100000331 toxic Toxicity 0.000 abstract description 3
- 230000002588 toxic effect Effects 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 238000004090 dissolution Methods 0.000 description 17
- 238000010521 absorption reaction Methods 0.000 description 15
- 238000007865 diluting Methods 0.000 description 11
- 239000010970 precious metal Substances 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 238000003723 Smelting Methods 0.000 description 2
- 101150113720 aunc gene Proteins 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000002082 metal nanoparticle Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- RLFUBODSGBPSLK-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;dodecyl sulfate Chemical compound CCCC[N+]=1C=CN(C)C=1.CCCCCCCCCCCCOS([O-])(=O)=O RLFUBODSGBPSLK-UHFFFAOYSA-M 0.000 description 1
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010793 electronic waste Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011829 room temperature ionic liquid solvent Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940126589 solid medicine Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C22B11/00—Obtaining noble metals
- C22B11/04—Obtaining noble metals by wet processes
-
- 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
- C22B15/00—Obtaining copper
- C22B15/0063—Hydrometallurgy
- C22B15/0065—Leaching or slurrying
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- 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
- C22B3/04—Extraction of metal compounds from ores or concentrates by wet processes by leaching
-
- 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
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- 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
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- General Life Sciences & Earth Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Geochemistry & Mineralogy (AREA)
- Manufacture And Refinement Of Metals (AREA)
Abstract
The invention relates to a novel ionic liquid 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt or iron salt, and a preparation method and application thereof. The ionic liquid has good oxidation and metal coordination capacity. The invention provides the application of the ionic liquid as a metal leaching agent, breaks through the defects of using a toxic noble metal leaching agent in the traditional metallurgy industry, and has the advantages of high efficiency, environmental protection and sustainability.
Description
(I) technical field
The invention relates to a novel ionic liquid 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt or iron salt, and a preparation method and application thereof.
(II) background of the invention
The noble metal has stable property and good conductivity, is widely applied to the fields of jewelry, currency, electronic information, aerospace, chemical engineering and the like, and is an indispensable important resource in the modern industry and the technological development process.
The content of noble metal in earth crust is very small, and the noble metal is very dispersed, the grade in the ore is low, the components are complex, so the extraction process is long, the cost is high, and the price is expensive. Noble metals are rare and expensive, and various waste materials containing noble metals have higher recovery value than common metals, so that the noble metals are more and more valued and are called as 'noble metal secondary resources'. It is statistical that the electronic waste and the spent catalyst generated each year contain a large amount of noble metals which are difficult to recover. According to the forecast of institutions such as university of united nations and the like, the total amount of electronic garbage produced globally in 2021 year is increased to 5220 million tons, the price of the contained precious metals exceeds 700 hundred million dollars, only 20 percent of the precious metals are recovered, and only a small part of the precious metals are recovered, so that huge resource waste is caused. Therefore, the method for efficiently and greenly recovering the precious metals from the waste resources not only has great economic value, but also is a difficult problem which needs to be solved urgently and is adhered to the sustainable development road in China.
In nature, precious metals are ubiquitous in ores, and smelting methods can be roughly divided into two main types of physical metallurgy and chemical metallurgy, but the physical metallurgy method is only suitable for high-grade ores, and the extraction efficiency is low. At present, the ore taste is generally low, and the gold ore which is difficult to process is much, so the precious metal smelting method is mainly a chemical method. Among the chemical processes, the cyanidation process is more mature.
The cyanidation method is the most mature and widely applied method for recovering precious metals at present: formation of Stable [ Au (CN) ]Using CN-and Au2]Complex compound, and thus Au can be extracted efficiently, but the highly toxic cyanide has great harm to the environment and human body.
In recent years, studies for replacing the cyanidation process are increasing, but all have different disadvantages. The advantages and disadvantages of the different leaching agents are shown in the following table:
therefore, a simple, efficient and environment-friendly method for extracting and recovering the precious metals is not available up to now.
The ionic liquid (or called ionic liquid) is a liquid composed of ions, is a liquid composed of ions at or near room temperature, and is called room-temperature ionic liquid, room-temperature molten salt, organic ionic liquid and the like, but the ionic liquid is called simply as the ionic liquid, does not have electrically neutral molecules, has nearly zero vapor pressure, is an environment-friendly reagent, can be used as a solvent for a plurality of organic matters, high molecular materials and inorganic matters, and is considered to be a good substitute for the traditional organic solvent.
Ionic liquids have been extensively studied and used in metal ion extraction. Obliosaca et al [ Bmim][C12H25OSO3](1-butyl-3-methylimidazolium dodecyl sulfate) preparation and stabilization of anisotropic gold nanocrystals (AuNC). It is found that a layer of cation layer is firstly formed on the surface of gold particles, a second layer of anion layer is formed by anions through electrostatic force, and van der Waals force exists between butyl and dodecyl to form secondary stability, so that the stability of AuNC is further guaranteed.
The existing research shows that: 1) the ionic liquid and the metal nano-particles have stronger interaction; 2) it is currently accepted that ionic liquids can stabilize metal nanoparticles. Thus, although ionic liquids are an ideal class of environmentally friendly solvents, there appears to be some "southern beam ruts" with which to study the dissolution and recovery of precious metals.
However, ionic liquids are also attractive in their designability, and introduction of special functional groups into cations and/or anions of ionic liquids to make them functional ionic liquids with special properties is also a research hotspot in recent years.
The introduction of the functionalized group into the ionic liquid skeleton can adjust the solvent-related properties of the ionic liquid, and can make the substrate in which the ionic liquid can be dissolved covalently bonded, or make the ionic liquid have the ability of catalytic activity, which is the most active research field of functionalized ionic liquids and is a research hotspot of functionalized ionic liquids in recent years.
Disclosure of the invention
The invention aims to provide a novel ionic liquid, namely 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt or 1- (4-carboxyperoxybenzyl) -3-methylimidazole iron tetrachloride salt, which has good oxidation and metal coordination capacities.
The second purpose of the invention is to provide a preparation method of 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum (iron) tetrachloride serving as an ionic liquid.
The third purpose of the invention is to provide the application of the ionic liquid 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum (iron) tetrachloride as a metal leaching agent, break through the defects of using a toxic noble metal leaching agent in the traditional metallurgy industry, and have the advantages of high efficiency, environmental protection and sustainability.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an ionic liquid, which has a chemical name of 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt or 1- (4-carboxyperoxybenzyl) -3-methylimidazole iron tetrachloride salt, and has the following structure:
in a second aspect, the present invention provides a method for preparing an ionic liquid, the method comprising:
(1) the three-port glass instrument is used for removing water by a high-temperature spray gun, double-row pipes are used for vacuumizing, p-chloromethylbenzoic acid is added under the protection of nitrogen, tetrahydrofuran (solvent) and N-methylimidazole which are subjected to water re-evaporation and water removal are injected, the anhydrous and oxygen-free conditions are ensured, heating reflux is carried out, after full reaction, diethyl ether is added into reaction liquid, scraping and standing precipitation are carried out, and filtering is carried out to obtain 1- (4-carboxybenzyl) -3-methylimidazole chloride salt;
(2) dissolving the 1- (4-carboxylbenzyl) -3-methylimidazole chloride salt obtained in the step (1) in dichloromethane or ether, adding an oxidant aqueous solution, wherein the oxidant is at least one of potassium permanganate, potassium persulfate and ammonium persulfate, finally adding a phase transfer catalyst, reacting at 15-25 ℃, and filtering after full reaction to obtain 1- (4-carboxyperoxybenzyl) -3-methylimidazole chloride salt;
(3) dissolving the 1- (4-carboxyperoxybenzyl) -3-methylimidazole chloride salt obtained in the step (2) in deionized water under the protection of nitrogen, stirring to dissolve the chloride salt, then adding anhydrous aluminum trichloride or anhydrous ferric trichloride, heating, refluxing and stirring, keeping the whole system in a nitrogen atmosphere, then performing rotary evaporation to remove the solvent, performing vacuum drying on the obtained product, and transferring the product to nitrogen to obtain ionic liquid, namely 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt or 1- (4-carboxyperoxybenzyl) -3-methylimidazole ferric tetrachloride salt.
Preferably, in the step (1), the reaction conditions are as follows: heating and refluxing for 6-10 hours.
Preferably, the feeding molar ratio of the p-chloromethylbenzoic acid to the N-methylimidazole is 1.0-1.2: 1.
Preferably, in step (2), the reaction time is 12 to 18 hours, more preferably 15 hours under reflux.
Preferably, the phase transfer catalyst in step (2) is at least one of benzyltriphenylphosphonium chloride, benzyltriphenylphosphonium bromide, methyltriphenylphosphonium chloride, methyltriphenylphosphonium bromide, methyltrioctylammonium chloride, methyltrioctylammonium bromide and benzyltriethylammonium chloride.
Preferably, in the step (2), the feeding molar ratio of the 1- (4-carboxybenzyl) -3-methylimidazole chloride salt to the oxidant and the phase transfer catalyst is 10: 20: 1.
preferably, in the step (3), the feeding molar ratio of the 1- (4-carboxyperoxybenzyl) -3-methylimidazole chloride salt to the anhydrous aluminum trichloride or the ferric trichloride is 0.45-1: 1.
preferably, in the step (3), the reaction conditions are as follows: heating and refluxing for 4-6 hours.
In a third aspect, the present invention provides the use of the ionic liquid as a metal leaching agent, the use comprising: adding a sample containing metal into the ionic liquid, and fully stirring to leach the metal.
Preferably, the sample containing metal is metal powder or gold ore particles.
Preferably, the metal is a noble metal, and the noble metal is at least one of gold, palladium, platinum and rhodium.
Preferably, the application conditions are: the temperature is 30-100 ℃, the further optimized temperature is 40-60 ℃, the temperature range is still a low-temperature section, only slight temperature rise is needed, the energy consumption is low, the gold leaching efficiency is good, and the metal powder can be dissolved within a few hours (such as 15 min).
In the application of the invention, the 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum (iron) tetrachloride can be recycled. The specific operation steps are as follows: after the noble metal is leached, adding deionized water with a certain proportion into the obtained leaching solution for precipitation at room temperature, carrying out suction filtration and separation on a solid-liquid mixture, evaporating moisture in the obtained filtrate, and adding anhydrous aluminum trichloride or anhydrous ferric trichloride with a certain mass to obtain a recovered ionic liquid which can be recycled; and reducing the solid precipitate with hydrazine hydrate solution of certain concentration to obtain simple substance noble metal.
Preferably, the volume ratio of the obtained leachate to water is 1:3 to 1:20, and more preferably 1:5 to 1: 10.
Preferably, the addition amount of the anhydrous aluminum trichloride or the anhydrous ferric trichloride is equivalent to the molar amount of the ionic liquid, the usage amount of the anhydrous aluminum trichloride or the anhydrous ferric trichloride is preferably excessive, and the mass ratio of the noble metal palladium to the anhydrous aluminum trichloride or the anhydrous ferric trichloride is preferably 1:100-1:300, and more preferably 1: 250-1: 270.
Preferably, the reduction temperature is 30 to 40 ℃.
Compared with the traditional gold leaching agent, the invention has the following advantages:
1. 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum (iron) tetrachloride is an environment-friendly ionic liquid, has almost no harm to the environment and people in the production process, meets the requirement of building an environment-friendly society at present, and is a gold leaching agent capable of being developed sustainably;
2. the 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum (iron) tetrachloride salt has oxidability and strong complexing ability, does not need to add an oxidant and a ligand additionally during gold leaching, and has good leaching ability for noble metals;
3. the ionic liquid can be recycled after gold leaching, so that the cost is greatly reduced;
4. 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum (iron) tetrachloride is used as a gold leaching agent, so that the extraction of palladium, gold, copper and iron can be carried out at a low temperature, the conditions are mild, the efficiency is high, and the overall energy consumption is low.
(IV) description of the drawings
FIG. 1 shows 1- (4-carboxyperoxybenzyl) -3-methylimidazolium tetrachloride (iron) salt1H NMR chart.
1H NMR(400MHz,Deuterium Oxide)δ8.74(s,1H),7.96(d,J＝8.0Hz,2H),7.40(d,J＝8.0Hz,4H),5.41(s,2H),3.83(s,3H).
(V) detailed description of the preferred embodiments
The invention is illustrated by the following specific examples. It should be noted that the examples are only for further illustration of the present invention, but should not be construed as limiting the scope of the present invention, which is not limited thereto in any way. Those skilled in the art may make insubstantial modifications and adaptations to the invention described above.
The 1- (4-carboxyperoxybenzyl) -3-methylimidazolium aluminum (iron) tetrachloride salt used in the examples of the invention was prepared using the procedures of examples 1 and 2.
Example 1
(1) Three-port glass instruments used in the experimental process are subjected to water removal by using a high-temperature spray gun, are vacuumized by using double-row pipes, and are added with solid medicines under the protection of nitrogen, so that the anhydrous and oxygen-free conditions are ensured.
Adding weighed 8.53g of p-chloromethylbenzoic acid into a 100mL three-neck flask with magnetons, installing a condenser pipe and a three-way pipe, connecting a balloon filled with nitrogen with the three-way pipe (gas protection), sealing by using a rubber thread plug, exhausting and ventilating for at least 3 times, then injecting 50mL of redistilled tetrahydrofuran into the flask, slowly injecting 4.11g N-methylimidazole into the solution, continuously stirring and heating for 70 ℃, stirring and reacting for 8 hours, cooling the reaction solution to room temperature after the reaction is finished, adding diethyl ether into the reaction solution, scraping and standing for precipitation, and filtering to obtain 1- (4-carboxybenzyl) -3-methylimidazolium chloride salt, wherein the yield is 33%.
(2) Weighing 2.53g of the obtained 1- (4-carboxylbenzyl) -3-methylimidazole chloride salt, dissolving the 1- (4-carboxylbenzyl) -3-methylimidazole chloride salt in 100mL of dichloromethane or diethyl ether, adding 150mL of ammonium persulfate aqueous solution with the concentration of 0.134mol/L, adding 0.22g of phase transfer catalyst benzyltriethylammonium chloride, heating at 15 ℃, stirring for 15 hours, fully reacting, and filtering to obtain the 1- (4-carboxyperoxybenzyl) -3-methylimidazole chloride salt with the yield of 64%.
(3) 0.5337g of the obtained 1- (4-carboxyperoxybenzyl) -3-methylimidazole chloride salt is dissolved in 3mL of deionized water under the protection of nitrogen, 0.53g of anhydrous aluminum trichloride is added, the mixture is heated, refluxed and stirred for 6 hours, the whole system is kept in the nitrogen atmosphere, then the solvent is removed on a rotary evaporator, the obtained product is dried in a vacuum drying oven, and the nitrogen protection is carried out overnight to obtain the 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt.
FIG. 1 shows the preparation of 1- (4-carboxyperoxybenzyl) -3-methylimidazolium tetrachloride salt1H NMR chart.
Example 2
Steps (1) to (2) were the same as in example 1.
(3) 0.5337g of the obtained 1- (4-carboxyperoxybenzyl) -3-methylimidazole chloride salt is dissolved in 3mL of deionized water under the protection of nitrogen, 0.62g of anhydrous ferric chloride is added, heating reflux and stirring are carried out for 6 hours, the whole system is kept under the nitrogen atmosphere, then the solvent is removed on a rotary evaporator, the obtained product is dried in a vacuum drying oven, and the 1- (4-carboxyperoxybenzyl) -3-methylimidazole tetrachloroferric salt is obtained after the nitrogen protection is carried out overnight.
Example 3
Taking 4g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt, adding 0.0021g of palladium powder to obtain 3.1mL of solution, slightly heating to 60 ℃ for 15min, basically completely dissolving the palladium powder, diluting the sample by 500 times, measuring the Pd concentration by using an atomic absorption spectrometer to be 1.353ug/mL, and calculating to obtain the dissolution rate to be 99.88%.
Example 4
8g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol iron tetrachloride salt is taken, 0.0040g of palladium powder is added to obtain 6.7mL of solution, the solution is heated to 60 ℃ for 15min slightly, the palladium powder is dissolved completely, a sample is diluted by 500 times, the concentration of Pd is measured by an atomic absorption spectrometer to be 1.016ug/mL, and the calculated dissolution rate is 85.09%.
Example 5
Taking 3.8g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride, adding 0.0023g of palladium powder to obtain 3mL of solution, slightly heating to 60 ℃, dissolving the palladium powder for 15min completely, diluting the sample by 500 times, measuring the concentration of Pd by using an atomic absorption spectrometer to be 1.427ug/mL, and calculating to obtain the dissolution rate of 93.01%.
Example 6
3.6g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride was taken, 0.0023g of palladium powder was added to obtain 3mL of solution, which was slightly heated to 60 ℃ for 15min, the palladium powder was substantially completely dissolved, the sample was diluted 500 times, the Pd concentration measured by atomic absorption spectrometry was 1.262ug/mL, and the dissolution rate was calculated to be 82.30%.
Example 7
Taking 3g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt, adding 0.0021g of palladium powder to obtain 2.8mL of solution, slightly heating to 60 ℃ for 15min, basically completely dissolving the palladium powder, diluting the sample by 500 times, measuring the Pd concentration by using an atomic absorption spectrometer to be 1.212ug/mL, and calculating to obtain the dissolution rate of 80.80%.
Example 8
Taking 4g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride, adding 0.0023g of copper powder to obtain 3.1mL of solution, slightly heating to 60 ℃ for 1min to ensure that the copper powder is basically and completely dissolved, diluting the sample by 500 times, measuring the Cu concentration to be 1.485ug/mL by using an atomic absorption spectrometer, and calculating to obtain the dissolution rate to be 100%.
Example 9
Taking 4g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt, adding 0.0026g of iron powder to obtain 3.1mL of solution, slightly heating to 60 ℃ for 5min, wherein the iron powder is basically and completely dissolved, diluting the sample by 500 times, measuring the Fe concentration by using an atomic absorption spectrometer to be 1.682ug/mL, and calculating the dissolution rate to be 100%.
Example 10
Taking 4g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt, adding 0.0023g of gold powder to obtain 4mL of solution, slightly heating to 60 ℃, dissolving the gold powder for 30min completely, diluting the sample by 50 times, measuring the Au concentration by using an atomic absorption spectrometer to be 10.358ug/mL, and calculating to obtain the dissolution rate to be 90.07%.
Example 11
Taking 4g of 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt, adding 0.0020g of platinum powder to obtain 3.1mL of solution, slightly heating to 60 ℃ for 1 hour to ensure that the platinum powder is completely dissolved basically, diluting the sample by 500 times, measuring the concentration of Pt by using an atomic absorption spectrometer to be 1.093ug/mL, and calculating to obtain the dissolution rate of 84.70%.
Example 12
4g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt is taken, 0.0020g of rhodium powder is added to obtain 3.1mL of solution, the solution is slightly heated to 60 ℃ for 1 hour, the rhodium powder is basically and completely dissolved, a sample is diluted by 500 times, the Rh concentration measured by an atomic absorption spectrometer is 1.198ug/mL, and the dissolution rate is calculated to be 92.84%.
Example 13
Taking 4g of 1- (4-carboxyperoxybenzyl) -3-methylimidazol aluminum tetrachloride salt, adding 0.0021g of palladium powder to obtain 3.1mL of solution, slightly heating to 60 ℃ for 15min, basically completely dissolving the palladium powder, diluting the sample by 500 times, measuring the Pd concentration by using an atomic absorption spectrometer to be 1.353ug/mL, and calculating to obtain the dissolution rate to be 99.88%.
Stirring was continued, 30mL of water was added for precipitation, and the solid and clear liquid were separated. The solid was reduced with 1mL of 0.5g/mL hydrazine hydrate aqueous solution. The solvent was distilled off from the clear solution, and 0.25g of anhydrous aluminum trichloride was added to obtain 1g of recovered ionic liquid 1. And (3) adding 0.001g of palladium powder into the recovered ionic liquid 1, heating and stirring to obtain 1mL of solution, diluting the sample by 500 times, measuring the concentration of Pd in the solution to be 1.895ug/mL by using an atomic absorption spectrometer, and calculating to obtain the dissolution rate to be 94.75%. 30mL of water was added for precipitation, and the solid and clear solution were separated. The solid was reduced with 1mL of 0.5g/mL hydrazine hydrate aqueous solution. The solvent was distilled off from the clear solution, and 0.25g of anhydrous aluminum trichloride was added to obtain 0.5g of recovered ionic liquid 2. 0.001g of palladium powder is added into the solution and stirred to obtain 0.5mL of solution, the sample is diluted by 500 times, the concentration of Pd in the solution is measured to be 2.496ug/mL by an atomic absorption spectrometer, and the calculated dissolution rate is 62.40 percent.
Comparative example 1
Dissolving 1.5g of 1- (4-carboxybenzyl) -3-methylimidazolium chloride salt in 2mL of deionized water to obtain 2.6mL of solution, adding 0.001g of palladium powder, stirring, slightly heating to 60 ℃, basically insolubilizing the palladium powder, diluting the sample by 500 times, and determining the concentration of Pd in the solution to be 0.004ug/mL by using an atomic absorption spectrometer, wherein the calculated dissolution rate is 0.52%.
Comparative example 2
Dissolving 1.5g of 1-butyl-3-methylimidazole aluminum tetrachloride salt in 2mL of deionized water to obtain 2.6mL of solution, adding 0.001g of palladium powder, stirring, slightly heating to 60 ℃, basically insolubilizing the palladium powder, diluting the sample by 500 times, measuring the concentration of Pd in the solution by using an atomic absorption spectrometer to be 0.012ug/mL, and calculating to obtain the dissolution rate of 1.56%.
Comparative example 3
1.5g of 1-hexyl-3-methylimidazole iron tetrachloride salt is dissolved in 2mL of deionized water to obtain 2.6mL of solution, 0.001g of palladium powder is added and stirred, the solution is heated to 60 ℃ slightly, the palladium powder is basically insoluble, a sample is diluted by 500 times, the concentration of Pd in the solution is measured to be 0.008ug/mL by an atomic absorption spectrometer, and the dissolution rate is calculated to be 1.04%.
Claims (10)
1. An ionic liquid, the chemical name of which is 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt or 1- (4-carboxyperoxybenzyl) -3-methylimidazole iron tetrachloride salt, and the structure of which is shown as follows:
2. a method of preparing the ionic liquid of claim 1, comprising:
(1) the three-port glass instrument is used for removing water by using a high-temperature spray gun, vacuumizing by using a double-row pipe, adding p-chloromethylbenzoic acid under the protection of nitrogen, injecting tetrahydrofuran and N-methylimidazole subjected to redistillation and water removal, ensuring that the anhydrous and anaerobic conditions are met, heating and refluxing, adding diethyl ether into a reaction solution after full reaction, scraping, standing and precipitating, and filtering to obtain 1- (4-carboxybenzyl) -3-methylimidazolium chloride;
(2) dissolving the 1- (4-carboxylbenzyl) -3-methylimidazole chloride salt obtained in the step (1) in dichloromethane or ether, adding an oxidant aqueous solution, wherein the oxidant is at least one of potassium permanganate, potassium persulfate and ammonium persulfate, finally adding a phase transfer catalyst, reacting at 15-25 ℃, and filtering after full reaction to obtain 1- (4-carboxyperoxybenzyl) -3-methylimidazole chloride salt;
(3) dissolving the 1- (4-carboxyperoxybenzyl) -3-methylimidazole chloride salt obtained in the step (2) in deionized water under the protection of nitrogen, stirring to dissolve the chloride salt, then adding anhydrous aluminum trichloride or anhydrous ferric trichloride, heating, refluxing and stirring, keeping the whole system in a nitrogen atmosphere, then performing rotary evaporation to remove the solvent, performing vacuum drying on the obtained product, and transferring the product to nitrogen to obtain ionic liquid, namely 1- (4-carboxyperoxybenzyl) -3-methylimidazole aluminum tetrachloride salt or 1- (4-carboxyperoxybenzyl) -3-methylimidazole ferric tetrachloride salt.
3. The method of claim 2, wherein: in the step (1), the reaction conditions are as follows: heating and refluxing for 6-10 hours; the feeding molar ratio of the p-chloromethylbenzoic acid to the N-methylimidazole is 1.0-1.2: 1.
4. The method of claim 2, wherein: in the step (2), the reaction time is 12 to 18 hours.
5. The method of claim 2, wherein: the phase transfer catalyst in the step (2) is at least one of benzyltriphenylphosphonium chloride, benzyltriphenylphosphonium bromide, methyltriphenylphosphonium chloride, methyltriphenylphosphonium bromide, methyltrioctylammonium chloride, methyltrioctylammonium bromide and benzyltriethylammonium chloride, preferably, the feeding molar ratio of the 1- (4-carboxybenzyl) -3-methylimidazole chloride to the oxidant to the phase transfer catalyst is 10: 20: 1.
6. the method of claim 2, wherein: in the step (3), the feeding molar ratio of the 1- (4-carboxyperoxybenzyl) -3-methylimidazolium chloride to the anhydrous aluminum trichloride or the ferric trichloride is 0.45-1: 1; the reaction conditions are as follows: heating and refluxing for 4-6 hours.
7. Use of an ionic liquid according to claim 1 as a metal leaching agent, the use comprising: adding a sample containing metal into the ionic liquid, and fully stirring to leach the metal.
8. The use of claim 7, wherein: the metal is noble metal, and the noble metal is at least one of gold, palladium, platinum and rhodium.
9. Use according to claim 7 or 8, characterized in that: the application conditions are as follows: the temperature is 30-100 ℃, and the further optimized temperature is 40-60 ℃.
10. Use according to claim 7 or 8, characterized in that: in the application, the specific operation steps for recovering the ionic liquid are as follows: after the metal is leached, deionized water with a certain proportion is added into the obtained leaching solution for precipitation at room temperature, solid-liquid mixture is filtered and separated, and after moisture in the obtained filtrate is evaporated, anhydrous aluminum trichloride or anhydrous ferric trichloride with a certain mass is added to obtain the recovered ionic liquid which can be recycled.
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