CN114262282B - Aldoxime compound and preparation method and application thereof - Google Patents
Aldoxime compound and preparation method and application thereof Download PDFInfo
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- CN114262282B CN114262282B CN202111547747.5A CN202111547747A CN114262282B CN 114262282 B CN114262282 B CN 114262282B CN 202111547747 A CN202111547747 A CN 202111547747A CN 114262282 B CN114262282 B CN 114262282B
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- -1 Aldoxime compound Chemical class 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000010949 copper Substances 0.000 claims abstract description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052802 copper Inorganic materials 0.000 claims abstract description 15
- 239000012141 concentrate Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 28
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- 238000000227 grinding Methods 0.000 claims description 14
- 239000005751 Copper oxide Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 229910000431 copper oxide Inorganic materials 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- MXLMTQWGSQIYOW-UHFFFAOYSA-N methyl isopropyl carbinol Natural products CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical class C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 claims description 6
- 235000019982 sodium hexametaphosphate Nutrition 0.000 claims description 6
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 claims description 6
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 claims description 6
- 239000004088 foaming agent Substances 0.000 claims description 5
- UMUKSOFZUAPNLY-UHFFFAOYSA-N formaldehyde;naphthalen-2-ol Chemical compound O=C.C1=CC=CC2=CC(O)=CC=C21 UMUKSOFZUAPNLY-UHFFFAOYSA-N 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 5
- 235000012141 vanillin Nutrition 0.000 claims description 5
- 239000004115 Sodium Silicate Substances 0.000 claims description 4
- IYRDVAUFQZOLSB-UHFFFAOYSA-N copper iron Chemical compound [Fe].[Cu] IYRDVAUFQZOLSB-UHFFFAOYSA-N 0.000 claims description 4
- 229910001608 iron mineral Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 229910052911 sodium silicate Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000004537 pulping Methods 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- 238000005188 flotation Methods 0.000 abstract description 32
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 25
- 239000011707 mineral Substances 0.000 abstract description 25
- 238000001179 sorption measurement Methods 0.000 abstract description 16
- 239000003814 drug Substances 0.000 abstract description 10
- 229910000570 Cupronickel Inorganic materials 0.000 abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
- 239000013078 crystal Substances 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 150000002500 ions Chemical class 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 4
- 125000003544 oxime group Chemical group 0.000 abstract description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 33
- 241000907663 Siproeta stelenes Species 0.000 description 33
- GJDGYWVSQUBDDP-WEVVVXLNSA-N 2-[(E)-hydroxyiminomethyl]-6-methoxyphenol Chemical compound COc1cccc(\C=N\O)c1O GJDGYWVSQUBDDP-WEVVVXLNSA-N 0.000 description 18
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- 238000011084 recovery Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 10
- 229910052742 iron Inorganic materials 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- VPTYRUGUZUYAGZ-KPKJPENVSA-N chembl3103218 Chemical compound C1=CC=C2C(/C=N/O)=C(O)C=CC2=C1 VPTYRUGUZUYAGZ-KPKJPENVSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 4
- 239000004570 mortar (masonry) Substances 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- GJDGYWVSQUBDDP-UHFFFAOYSA-N 2-(hydroxyiminomethyl)-6-methoxyphenol Chemical compound COC1=CC=CC(C=NO)=C1O GJDGYWVSQUBDDP-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- VPTYRUGUZUYAGZ-UHFFFAOYSA-N 1-(hydroxyiminomethyl)naphthalen-2-ol Chemical compound C1=CC=C2C(C=NO)=C(O)C=CC2=C1 VPTYRUGUZUYAGZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000012863 analytical testing Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000000498 ball milling Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 229910052598 goethite Inorganic materials 0.000 description 2
- AEIXRCIKZIZYPM-UHFFFAOYSA-M hydroxy(oxo)iron Chemical compound [O][Fe]O AEIXRCIKZIZYPM-UHFFFAOYSA-M 0.000 description 2
- IQKLAEINENLGAG-UHFFFAOYSA-N iron oxocopper Chemical compound [Fe].[Cu]=O IQKLAEINENLGAG-UHFFFAOYSA-N 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 description 2
- 235000011151 potassium sulphates Nutrition 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- 229910002703 Al K Inorganic materials 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- UOJYYXATTMQQNA-UHFFFAOYSA-N Proxan Chemical compound CC(C)OC(S)=S UOJYYXATTMQQNA-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- VDEUYMSGMPQMIK-UHFFFAOYSA-N benzhydroxamic acid Chemical group ONC(=O)C1=CC=CC=C1 VDEUYMSGMPQMIK-UHFFFAOYSA-N 0.000 description 1
- KRJUSWXDFZSJQD-UHFFFAOYSA-N benzoic acid;lead Chemical compound [Pb].OC(=O)C1=CC=CC=C1 KRJUSWXDFZSJQD-UHFFFAOYSA-N 0.000 description 1
- 229910001779 copper mineral Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000011019 hematite Substances 0.000 description 1
- 229910052595 hematite Inorganic materials 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- 238000007885 magnetic separation Methods 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JRZGPWOEHDOVMC-UHFFFAOYSA-N n-hydroxynaphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)NO)=CC=CC2=C1 JRZGPWOEHDOVMC-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QWENMOXLTHDKDL-UHFFFAOYSA-N pentoxymethanedithioic acid Chemical compound CCCCCOC(S)=S QWENMOXLTHDKDL-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
Classifications
-
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to an aldoxime compound, a preparation method and application thereof. The aldoxime compound has a structural formula shown in a formula (I) or a formula (II): the aldoxime compound provided by the invention has an intramolecular ligand consisting of hydroxyl and oxime groups on benzene rings, has selective adsorption characteristics on cupronickel mineral, can selectively chemically adsorb positioning ions on the surface of mineral crystals, can be further used as a collector to realize the efficient flotation of the cupronickel mineral, can obtain high-quality copper concentrate, and has small consumption of medicament.
Description
Technical Field
The invention relates to the field of flotation reagents and preparation thereof, in particular to an aldoxime compound and a preparation method and application thereof.
Technical Field
In the current beneficiation technical scope, the treatment method of the copper oxide ore comprises a flotation method, a chemical method and a beneficiation and metallurgy combined method. Comprehensively considering factors such as chemical reagents, energy sources, environmental influence and the like, flotation is the most economical and mature technology for treating copper oxide.
There have been some studies on collectors for copper oxide ores. For example, the chelated cupronickel reagent, i.e. the mixture of phenanthroline, lead benzoate and ethanolamine, the mixture of benzoic hydroxamic acid, isopropyl xanthate and fatty alcohol polyoxyethylene ether, and the like, has a certain collecting effect on copper oxide ores. These collectors are not suitable for the separation of delafossite, particularly high iron oxide ores. This is mainly because: such collectors have a high affinity for iron ions and minerals. Under the condition that inhibitors and weak bases are not used, copper minerals and iron minerals can float up simultaneously by using the two types of medicaments, and efficient separation is difficult to realize.
The prior patent discloses a recovery method of high-clay iron refractory copper oxide ores, which selects benzoic hydroxamic acid and amyl xanthate as collectors and ammonium sulfate and sodium sulfide as activators, and 3 copper concentrate products are obtained by carrying out preferential rapid flotation, sectional flotation and physical magnetic separation on the high-clay iron refractory copper oxide ores. The mineral separation process solves the problems of the full heap leaching process, such as poor permeability, low leaching rate, high acid consumption, high consumption of neutralized lime, and the like. However, hydroxamic acid agents have a strong effect on iron ores, and when applied to copper ores of this type, have the disadvantages of high regulator consumption and insufficient concentrate grade.
Therefore, there is a need to develop a high selectivity collector suitable for the flotation separation of delafossite.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provides an aldoxime compound. The invention provides aldoxime compounds. The aldoxime compound provided by the invention has an intramolecular ligand consisting of hydroxyl and oxime groups on benzene rings, has selective adsorption characteristics on cupronickel mineral, can selectively chemically adsorb positioning ions on the surface of mineral crystals, can be further used as a collector to realize the efficient flotation of the cupronickel mineral, can obtain high-quality copper concentrate, and has small consumption of medicament.
Another object of the present invention is to provide a process for producing the above aldoxime compound.
Another object of the invention is to provide the use of the above aldoxime compounds as collectors in mineral separation.
Another object of the invention is to provide a method for beneficiation of copper-iron minerals.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
an aldoxime compound has a structural formula shown in a formula (I) or a formula (II):
An aldoxime compound represented by the formula (I), namely 2-hydroxy-1-naphthoxyoxime; an aldoxime compound represented by the formula (II), namely 2-hydroxy-3-methoxy-benzaldoxime.
The aldoxime compound provided by the invention has an intramolecular ligand consisting of hydroxyl and oxime groups on benzene rings, has selective adsorption characteristics on cupronickel mineral, can selectively chemically adsorb positioning ions on the surface of mineral crystals, can be further used as a collector to realize the efficient flotation of the cupronickel mineral, can obtain high-quality copper concentrate, and has small consumption of medicament.
The preparation method of the aldoxime compound comprises the following steps:
S11: mixing 2-hydroxynaphthalene formaldehyde, hydroxylamine solution and alkaline substance, and reacting to obtain aldoxime compound shown in formula (I);
S12: mixing o-methoxy vanillin, hydroxylamine solution and alkaline substance, and reacting to obtain aldoxime compound shown in formula (II).
Preferably, the solvent in S11 is one or more of glycerol, ethylene glycol, ethanol or methanol.
Preferably, the reaction time of the reaction in S11 is 5 to 20 minutes.
Preferably, the alkaline substance in S11 is one or more of sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide or a solution thereof.
Preferably, the molar ratio of the 2-hydroxynaphthalene formaldehyde to the hydroxylamine in S11 is 1 (1.1-1.2).
Preferably, the specific process of the reaction in S11 is: mixing 2-hydroxynaphthalene formaldehyde with hydroxylamine solution, grinding, and adding alkaline substances dropwise during grinding, and reacting.
More preferably, the hydroxylamine solution is prepared by the following process: adding alkaline substances into hydroxylamine hydrochloride, hydroxylamine sulfate or a mixed solution thereof until the pH value is neutral, thus obtaining hydroxylamine solution.
Preferably, the solvent in S12 is one or more of glycerol, ethylene glycol, ethanol or methanol.
Preferably, the reaction time of the reaction in S12 is 5 to 20 minutes.
Preferably, the alkaline substance in S12 is one or more of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide or a solution thereof.
Preferably, in the S12, the molar ratio of the o-methoxy vanillin to the hydroxylamine in the hydroxylamine solution is 1 (1.1-1.2).
Preferably, the specific process of the reaction in S12 is: mixing o-methoxy vanillin and hydroxylamine solution, grinding, and dripping alkaline substance during grinding to react.
More preferably, the hydroxylamine solution is prepared by the following process: adding alkaline substances into hydroxylamine hydrochloride, hydroxylamine sulfate or a mixed solution thereof until the pH value is neutral, thus obtaining hydroxylamine solution.
The application of the aldoxime compound as a collector in mineral separation is also within the protection scope of the invention.
Preferably, the ore in the beneficiation is a goethite. More preferably, the copper oxide ore is high-iron copper oxide ore.
A beneficiation method for copper-iron minerals comprises the following steps:
S21: classifying and grinding the raw ore of the copper oxide ore until the concentration of the ore material with the total fineness of not more than 0.074mm is 70% -80%;
s22: adding a regulator, an inhibitor, an aldoxime compound and a foaming agent according to claim 1, and carrying out size mixing until the weight concentration of ore pulp is 20% -30%, and roughing to obtain copper concentrate.
Preferably, the regulator in S22 is one or more of sodium carbonate, lime, sodium hydroxide or sulfuric acid.
Preferably, the amount of the regulator in S22 is 200-3000g/t (calculated as raw ore, the same applies hereinafter).
Preferably, the inhibitor in S22 is one or both of sodium silicate or sodium hexametaphosphate.
More preferably, the inhibitor is water glass and sodium hexametaphosphate, the dosage of the water glass is 200-500g/t, and the dosage of the sodium hexametaphosphate is 150-350 g/t.
Preferably, the collector in S22 is used in an amount of 5-600g/t of collector.
Preferably, the foaming agent in S22 is methyl isopropyl methanol.
Preferably, the amount of the foaming agent in S22 is 50 to 100g/t.
Preferably, the roughing time in S22 is 1 to 5 minutes.
Compared with the prior art, the invention has the following beneficial effects:
The invention provides aldoxime compounds. The aldoxime compound provided by the invention has an intramolecular ligand consisting of hydroxyl and oxime groups on benzene rings, has selective adsorption characteristics on cupronickel mineral, can selectively chemically adsorb positioning ions on the surface of mineral crystals, can be further used as a collector to realize the efficient flotation of the cupronickel mineral, can obtain high-quality copper concentrate, and has small consumption of medicament.
Drawings
FIG. 1 is a flow chart of the high-iron copper oxide flotation process of the invention;
FIG. 2 is an infrared spectrum of 2-hydroxy-3-methoxybenzaldehyde oxime;
FIG. 3 is an infrared spectrum of 2-hydroxy-1-naphthaldoxime;
FIG. 4 is a liquid mass spectrum of 2-hydroxy-3-methoxybenzaldehyde oxime;
FIG. 5 is a liquid mass spectrum of 2-hydroxy-1-naphthaldoxime;
FIG. 6 is a graph showing adsorption of N1sXPS of 2-hydroxy-3-methoxybenzaldehyde oxime on the surface of malachite and limonite;
FIG. 7 is a graph showing adsorption of N1sXPS to 2-hydroxy-1-naphthoxime on the surface of malachite and limonite;
FIG. 8 is a floatability relationship of 2-hydroxy-3-methoxybenzaldehyde oxime to malachite and limonite;
FIG. 9 is a floatability relationship of benzoic hydroxamic acid to malachite and limonite;
FIG. 10 is a floatability relationship of 2-hydroxy-1-naphthaceneoxime to malachite and limonite;
FIG. 11 shows the floatability relationship of naptha-mefloc acid to malachite and limonite.
Detailed Description
The invention is further illustrated below with reference to examples. These examples are only for illustrating the present invention and are not intended to limit the scope of the present invention. The experimental procedures in the examples below, without specific details, are generally performed under conditions conventional in the art or recommended by the manufacturer; the raw materials, reagents and the like used, unless otherwise specified, are those commercially available from conventional markets and the like. Any insubstantial changes and substitutions made by those skilled in the art in light of the above teachings are intended to be within the scope of the invention as claimed.
30.00G of hydroxylamine hydrochloride was added to 70.00g of ethylene glycol, dissolved by stirring, then 17.27g of sodium hydroxide was added in portions, and sodium chloride obtained by the reaction was filtered to obtain hydroxylamine solution-1.
30.00G of hydroxylamine sulfate was added to 70.00g of glycerin solution, and dissolved by stirring, then 24.17g of potassium hydroxide was added in portions, and the potassium sulfate obtained by the reaction was filtered to obtain hydroxylamine solution-2.
30.00G of hydroxylamine hydrochloride was added to 70.00g of an absolute ethanol solution, and dissolved by stirring, then 17.27g of sodium hydroxide was added in portions, and sodium chloride obtained by the reaction was filtered to obtain hydroxylamine solution-3.
30.00G of hydroxylamine sulfate was added to 70.00g of an anhydrous methanol solution, and dissolved by stirring, then 24.17g of potassium hydroxide was added in portions, and the resultant potassium sulfate was filtered to obtain hydroxylamine solution-4.
Example 1
This example provides an aldoxime compound: the structural formula and the preparation process of the 2-hydroxy-1-naphthaldehyde oxime are as follows:
10.00g of 2-hydroxy-1-naphthaldehyde and 13.20g of hydroxylamine solution-1 are weighed into a glass mortar, ground for 5 minutes, 10mL of 5% (mass fraction, same as below) NaOH aqueous solution is continuously added in the grinding process, and finally 20mL of 5% dilute sulfuric acid is added for quenching reaction. After the reaction, washing with distilled water for several times, and filtering to obtain 10.12g of 2-hydroxy-1-naphthaldehyde oxime with 86.37% yield.
As shown in FIG. 3, the infrared spectrum of 2-hydroxy-1-naphthol oxime shows that 3310cm -1 is the stretching vibration peak of-OH, 3041cm -1 is the stretching vibration peak of C-H on benzene ring, 1630cm -1 is the stretching vibration peak of C=N, 1589 and 1461cm -1 are the stretching vibration peaks of aromatic ring skeleton.
FIG. 5 shows a liquid mass spectrum of 2-hydroxy-1-naphthoxime. The molecular weight of 2-hydroxy-1-naphthaloxime (C 11H9NO2) is 187.07. From the liquid mass spectrum, a signal of the target product appeared at 14.83 minutes, and a fragment peak of [ M+1] appeared (188.07).
By combining an infrared spectrum and a liquid spectrum, the synthesized product is 2-hydroxy-1-naphthaldehyde oxime.
Example 2
The target compound of example 1
10.00G of 2-hydroxy-1-naphthaldehyde and 14.45g of hydroxylamine solution-2 are weighed into a glass mortar, ground for 15 minutes, and the grinding process is continuously dropwise added with 10mL of 5% K 2CO3 aqueous solution, and 20mL of 5% dilute sulfuric acid is added for quenching reaction. After the reaction, washing with distilled water for many times, and filtering to obtain 10.39g of 2-hydroxy-1-naphthaldehyde oxime, wherein the yield is 91.34%.
The infrared spectrum and the liquid spectrum of the obtained 2-hydroxy-1-naphthoxime were substantially identical to those in example 1.
Example 3
This example provides an aldoxime compound: the structural formula and the preparation process of the 2-hydroxy-3-methoxy benzaldehyde oxime are as follows:
10.00g of 2-hydroxy-3-methoxybenzaldehyde and 12.46g of hydroxylamine solution-3 are weighed into a glass mortar, ground for 10 minutes, dropwise added with 10mL of 5% KOH aqueous solution continuously during the grinding process, and finally added with 20mL of 5% dilute sulfuric acid for quenching reaction. After the reaction, washing with distilled water for several times, and filtering to obtain 10.27g of 2-hydroxy-3-methoxy-benzaldehyde oxime, the yield is 87.23%.
As shown in FIG. 2, the infrared spectrum of 2-hydroxy-3-methoxybenzaldehyde oxime, 3300cm -1 is the stretching vibration peak of-OH, 3069cm -1 is the stretching vibration peak of C-H on benzene ring, 2972 and 2368cm -1 are stretching vibration peaks of methyl, 1618cm -1 is the stretching vibration peak of C=N, 1577 and 1481cm -1 are aromatic ring skeleton vibration peaks, 1240cm -1 is the bending vibration peak in the inner surface of benzene ring.
FIG. 4 shows a liquid mass spectrum of 2-hydroxy-3-methoxybenzaldehyde oxime. The molecular weight of 2-hydroxy-3-methoxybenzaldehyde oxime (C 8H9NO3) was 167.07. From the liquid-mass diagram, the signal of the target product appears at 11.78 minutes, and the fragment peak of [ M+1] appears (168.07).
By combining an infrared spectrum and a liquid spectrum, the synthesized product is 2-hydroxy-3-methoxy benzaldehyde oxime.
Example 4
The target compound of example 3
10.00G of 2-hydroxy-3-methoxybenzaldehyde and 13.70g of hydroxylamine solution-4 are weighed into a glass mortar, ground for 20 minutes, and 10mL of 5% K 2CO3 aqueous solution is continuously added dropwise during the grinding process, and 20mL of 5% diluted hydrochloric acid is added for quenching reaction. After the reaction, washing with distilled water for several times, and filtering to obtain 10.65g of 2-hydroxy-3-methoxybenzaldehyde oxime, the yield is 94.16%.
The infrared spectrum and the liquid spectrum of the obtained 2-hydroxy-3-methoxy-benzaldoxime were substantially the same as those in example 1.
Example 5
The copper grade of the Yunnan is about 1%, the oxidation rate is 60%, the main copper oxides are malachite and blue copper ore, the iron content in the ore is higher, the grade reaches 40%, nonmagnetic limonite and hematite are the main materials, and the alkaline gangue minerals are quartz and feldspar. As in fig. 1, the flotation process is: ball milling is carried out on the high-iron copper oxide ore by adopting a ball mill, products with the particle size smaller than 0.074mm are obtained by grading, after re-milling is carried out on the ores with the particle size larger than 0.074mm, the products with the particle size smaller than 0.074mm are combined, and floatable products are obtained, wherein the products with the fineness smaller than 0.074mm account for 72% of the total amount and the concentration of ore pulp in percentage by weight is 24%; adding a regulator and an inhibitor for pulping, wherein the pH regulator is sodium carbonate, the pH value of ore pulp is 7-8, and the inhibitor is sodium silicate (400 g/t) and sodium hexametaphosphate (200 g/t); adding 2-hydroxy-3-methoxybenzaldehyde oxime (600 g/t), adding methyl isopropyl methanol (75 g/t), roughing ore pulp for 1 time, and obtaining copper concentrate containing Cu 5.8% and with recovery rate of 62.05% by using a medicament using system of mineral dressing specifically shown in Table 1.
Example 6
The ore sample was as in example 5.
The flotation process is as follows: ball milling is carried out on the high-iron copper oxide ore by adopting a ball mill, products with the particle size smaller than 0.074mm are obtained by grading, after re-milling is carried out on the ores with the particle size larger than 0.074mm, the products with the particle size smaller than 0.074mm are combined, and floatable products are obtained, wherein the products with the fineness smaller than 0.074mm account for 78% of the total amount and the weight ratio concentration of ore pulp is 26% by weight; adding a regulator and an inhibitor for pulping, wherein the pH regulator is sodium carbonate, the pH value of ore pulp is 7-8, and the inhibitor is sodium silicate (400 g/t) and sodium hexametaphosphate (200 g/t); adding 2-hydroxy-1-benzaldehyde oxime (600 g/t), adding methyl isopropyl methanol (75 g/t), roughing ore pulp for 1 time, and obtaining copper concentrate containing Cu 5.4% and with recovery rate of 68.05% by using a medicament using system of mineral dressing specifically shown in Table 1.
Comparative example 1
The high iron copper oxide ore treated in this comparative example and the flotation process were identical to example 5 except that the collector used was benzoic hydroxamic acid.
As a comparison, using benzoic hydroxamic acid as a collector, the copper concentrate obtained by flotation was only 2.15% lower in grade, and the copper recovery was also unsatisfactory, only 34.7%.
Comparative example 2
The high iron copper oxide ore treated in this comparative example and the flotation process were identical to example 5 except that the collector used was napthalenehydroxamic acid.
As compared with the prior art, the grade of copper concentrate obtained by flotation is only 3.12% lower, and the recovery rate of copper is also not high, namely 45.23%, by using the naphthalene hydroxamic acid as a collector.
Experimental example 1
The experimental example researches the adsorption effect of the collector 2-hydroxy-3-methoxybenzaldehyde oxime, malachite and limonite.
And selecting 2-hydroxy-3-methoxybenzaldehyde oxime-malachite and 2-hydroxy-3-methoxybenzaldehyde oxime-limonite products for testing.
The preparation process of the 2-hydroxy-3-methoxybenzaldehyde oxime-malachite and 2-hydroxy-3-methoxybenzaldehyde oxime-limonite products comprises the following steps: 2.00g of malachite or limonite is added into 20mL of 2-hydroxy-3-methoxy-benzaldehyde oxime solution (0.4%), the pH value is regulated to about 7, stirring is continued for 30 minutes, filtering and vacuum drying are carried out, and the product to be detected is obtained. After which analytical testing is performed.
XPS analysis was performed on a Thermo Scientific ESCALAB Xi instrument with an Al-K alpha X-ray source. The power is 200W, the energy is 20eV, the vacuum degree is 1.33×10 -7-1.33×10-6 Pa, and the detection angle is 45 deg.
The detection results are shown in FIG. 6.
FIG. 6 is a graph of N1sXPS spectra of 2-hydroxy-3-methoxybenzaldehyde oxime-malachite and limonite. From FIG. 6, it is understood that the adsorption of 2-hydroxy-3-methoxybenzaldehyde oxime on the surfaces of malachite and limonite is greatly different and the chemical shift is different. The N1s bonding energy of the medicament adsorbed on the surface of the malachite is 410.2eV (0.3 eV), and the medicament is firmly adsorbed and is characterized by chemical adsorption; whereas the N1s bonding energy of the agent adsorbed on limonite is 410.0eV (almost unchanged), the adsorption is loose and is a physical adsorption characteristic. The area of the N signal peak on the malachite surface was 17654.1CPS. EV, while the area of the N signal peak on the limonite surface was only 5068.4.4CPS. EV. The difference of the adsorption quantity and the intensity of the 2-hydroxy-3-methoxy-benzaldehyde oxime on the surface of the mineral directly causes the floatability difference of malachite and limonite in a flotation test, and is also the key for separating and enriching the malachite and limonite.
Experimental example 2
The experimental example researches the adsorption effect of the collector 2-hydroxy-1-naphthaloxime, malachite and limonite.
And selecting 2-hydroxy-1-naphthaldehyde oxime-malachite and 2-hydroxy-1-naphthaloxime-limonite products for testing.
The preparation process of the 2-hydroxy-1-naphthaldehyde oxime-malachite and 2-hydroxy-1-naphthaloxime-limonite products comprises the following steps: 2.00g of malachite or limonite is added into 50mL of 2-hydroxy-1-naphthaldehyde oxime solution (0.4%), the pH value is regulated to about 7, stirring is continued for 30 minutes, filtering and vacuum drying are carried out, and the product to be detected is obtained. After which analytical testing is performed.
XPS analysis conditions were the same as in Experimental example 1.
FIG. 7 is a graph of N1sXPS spectra of 2-hydroxy-1-naphthaldehyde oxime-malachite and limonite products. As can be seen from fig. 7, the N1s bonding energy of the chemical adsorbed to malachite was 410.2eV (0.2 eV), and the chemical adsorption characteristic was strong; whereas the N1s bonding energy of the agent adsorbed on limonite is 410.0eV, the adsorption is loose, and the physical adsorption characteristic is realized. The N signal peak area of the malachite surface was 9160.7CPS. EV, while the N signal peak area of the limonite surface was only 4142.9CPS. EV. The 2-hydroxy-1-naphthaldehyde oxime is similar to 2-hydroxy-3-methoxy-benzaldehyde oxime on the surface of the goethite, which shows that the collector is also a copper-iron selective collector.
Experimental example 3
The experimental example researches the influence of the pH value of ore pulp on floatability when the collector 2-hydroxy-3-methoxy-benzaldoxime is adopted to carry out flotation on malachite and limonite.
Malachite and limonite are selected as single mineral flotation test objects, and the granularity of the ore is 200-400 meshes. The comparative agent is benzohydroxamic acid.
2.00G of single mineral malachite and limonite were weighed separately and placed in an XFG-IV type hanging trough flotation machine, and stirred for 2 minutes after adding 30mL of water. The regulators (NaCO 3 and H 2SO4) were added to pH around 5.5, 7.0, 9.0 and 11.5 respectively (specifically 5.4, 7.1, 9.2 and 11.5), followed by the collector and frother methyl isobutyl carbinol. In the flotation process, manual foam scraping is adopted for 5 minutes, the obtained foam product and the product in the tank are dried respectively, and the flotation recovery rate is weighed and calculated.
When the addition amount of the 2-hydroxy-3-methoxy-benzaldehyde oxime in the flotation pulp system is 200mg/L, the flotation effect graph of the pH value of the pulp on malachite and limonite is shown in figure 8. As can be seen from fig. 8, the recovery rate of malachite at pH value increases and decreases; at a pH equal to 7.1, the recovery of malachite reached a maximum of 84.45%. For limonite, the recovery rate is less than 40%. At a pH of 7.1, the separation of malachite and limonite reached a maximum (58.31%). And compared with the comparative medicament, the trimethoprim has weaker collecting capability and insufficient selectivity. The flotation effect graph of the pH value of the ore pulp on the malachite and limonite at the same addition (200 mg/L) is shown in figure 9. When ph=9.2, the degree of separation of the two single minerals is only 16.08%.
Experimental example 4
The experimental example researches the influence of the pH value of ore pulp on floatability when the collector 2-hydroxy-1-naphthalldoxime is adopted to carry out flotation on malachite and limonite.
Malachite and limonite are selected as single mineral flotation test objects, and the granularity of the ore is 200-400 meshes. The comparative agent (collector) is naphthylmethyl hydroxamic acid.
The flotation conditions were the same as test 3 except that the collector was adjusted.
The flotation effect of the pulp pH values (specifically 5.4, 7.2, 9.3 and 11.3) on malachite and limonite is shown in FIG. 10 when the 2-hydroxy-1-naphtalactoxime is added to the flotation pulp system at 200 mg/L. As can be seen from fig. 10, the recovery rate of malachite all rises and then falls; when the pH is equal to 7.2, the recovery rate of malachite reaches a maximum of 92.65%. For limonite, the recovery under acidic conditions is overall higher than that under alkaline conditions. At a pH of 7.2, the separation of malachite and limonite was maximized (73.2%). And compared with the comparative reagent, the naphthalene mezoxime acid has weaker collecting capacity and insufficient selectivity. The flotation effect of the pH value of the ore pulp (specifically 5.3, 7.2, 9.1 and 11.6) on the malachite and limonite at the same addition amount (200 mg/L) is shown in figure 11. When ph=9.2, the degree of separation of the two single minerals is only 22.91%.
Finally, it should be noted that the above embodiments are merely representative examples of the present invention. Obviously, the technical solution of the invention is not limited to the above-described embodiments, but many variations are possible. All modifications which can be derived or suggested directly from the present disclosure by a person skilled in the art should be considered as the protection scope of the claims of the present invention.
Claims (6)
1. The preparation method of the aldoxime compound is characterized by comprising the following steps:
s11: mixing 2-hydroxynaphthalene formaldehyde and hydroxylamine, performing mechanical grinding reaction, and continuously dripping an aqueous solution of 5% alkaline substances in mass fraction in the grinding process to obtain an aldoxime compound shown in formula (I); the alkaline substance is one or more of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide or solution thereof; the molar ratio of the 2-hydroxynaphthalene formaldehyde to the hydroxylamine is 1 (1.1-1.2);
S12: mixing o-methoxy vanillin and hydroxylamine solution, performing mechanical grinding reaction, and continuously dripping aqueous solution of alkaline substances with mass fraction of 5% in the grinding process to obtain aldoxime compounds shown in formula (II); the alkaline substance is one or more selected from sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide or solution thereof; the molar ratio of the o-methoxy vanillin to the hydroxylamine is 1 (1.1-1.2);
The aldoxime compound has a structural formula shown in a formula (I) or a formula (II):
Formula (I) and formula (II).
2. The preparation method according to claim 1, wherein the solvent used for hydroxylamine in S11 is one or more of glycerol, ethylene glycol, ethanol, and methanol; the solvent used in the hydroxylamine solution in S12 is one or more of glycerol, ethylene glycol, ethanol or methanol.
3. The process according to claim 1, wherein the reaction time of the reaction in S11 is 5 to 20 minutes; the reaction time of the reaction in S12 is 5 to 20 minutes.
4. The application of aldoxime compounds as collectors in ore dressing is characterized in that the aldoxime compounds have a structural formula shown in a formula (I) or a formula (II):
Formula (I) and formula (II).
5. The beneficiation method for the copper-iron minerals is characterized by comprising the following steps of:
s21: classifying and grinding raw ores of the copper oxide ores until the total fineness of the ores is not higher than 0.074mm is 65% -80%;
s22: adding a regulator, an inhibitor and the aldoxime compound and the foaming agent obtained by the preparation method of claim 1, and pulping until the weight concentration of ore pulp is 20% -30%, and roughing to obtain copper concentrate.
6. The beneficiation method according to claim 5, wherein the modifier is one or more of hydrochloric acid, sodium bicarbonate, potassium hydroxide or potassium carbonate; the inhibitor is one or two of sodium silicate or sodium hexametaphosphate; the foaming agent is methyl isopropyl methanol.
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