WO2012139985A2 - Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore - Google Patents
Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore Download PDFInfo
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- WO2012139985A2 WO2012139985A2 PCT/EP2012/056396 EP2012056396W WO2012139985A2 WO 2012139985 A2 WO2012139985 A2 WO 2012139985A2 EP 2012056396 W EP2012056396 W EP 2012056396W WO 2012139985 A2 WO2012139985 A2 WO 2012139985A2
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- Prior art keywords
- formula
- carbon atoms
- compound
- compounds
- aliphatic
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 229910052742 iron Inorganic materials 0.000 title claims abstract description 33
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 title claims abstract description 26
- -1 diamine compounds Chemical class 0.000 title claims description 60
- 238000009291 froth flotation Methods 0.000 title claims description 7
- 150000001412 amines Chemical class 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
- 238000005188 flotation Methods 0.000 claims abstract description 31
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 25
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 19
- 229910001608 iron mineral Inorganic materials 0.000 claims abstract description 14
- 150000001450 anions Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 33
- 150000002825 nitriles Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 23
- 150000007513 acids Chemical class 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 7
- 229910052595 hematite Inorganic materials 0.000 claims description 4
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical group [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 230000000994 depressogenic effect Effects 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 235000011054 acetic acid Nutrition 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
- 230000005588 protonation Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
- 230000000881 depressing effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- TVONJMOVBKMLOM-UHFFFAOYSA-N 2-methylidenebutanenitrile Chemical compound CCC(=C)C#N TVONJMOVBKMLOM-UHFFFAOYSA-N 0.000 description 2
- YSGPDJCRZNUFBU-UHFFFAOYSA-N 2-methylidenepentanenitrile Chemical compound CCCC(=C)C#N YSGPDJCRZNUFBU-UHFFFAOYSA-N 0.000 description 2
- CCMZKOAOMQSOQA-UHFFFAOYSA-N 3-methyl-2-methylidenebutanenitrile Chemical compound CC(C)C(=C)C#N CCMZKOAOMQSOQA-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- JPNCZSADMGXVPA-UHFFFAOYSA-N 3-tridecoxypropan-1-amine Chemical compound CCCCCCCCCCCCCOCCCN JPNCZSADMGXVPA-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- VEONKVDXUADXFB-UHFFFAOYSA-N CCOCCCNCCC#N Chemical compound CCOCCCNCCC#N VEONKVDXUADXFB-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011019 hematite Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VDWRUZRMNKZIAJ-UHFFFAOYSA-N tetradecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCN VDWRUZRMNKZIAJ-UHFFFAOYSA-N 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D1/00—Flotation
- B03D1/001—Flotation agents
- B03D1/004—Organic compounds
- B03D1/01—Organic compounds containing nitrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D1/00—Flotation
- B03D1/001—Flotation agents
- B03D1/004—Organic compounds
- B03D1/016—Macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D1/00—Flotation
- B03D1/02—Froth-flotation processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/04—Carbamic acid halides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D2201/00—Specified effects produced by the flotation agents
- B03D2201/02—Collectors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D2201/00—Specified effects produced by the flotation agents
- B03D2201/04—Frothers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D2201/00—Specified effects produced by the flotation agents
- B03D2201/06—Depressants
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D2203/00—Specified materials treated by the flotation agents; specified applications
- B03D2203/02—Ores
- B03D2203/04—Non-sulfide ores
Definitions
- the present invention relates to a process for enriching an iron mineral from a silicate- containing iron ore by carrying out an inverse ore flotation process using alkyl ether amines and / or alkyl ether diamines.
- the invention also relates to novel ether amines and alkyl ether diamines and formulations containing the same.
- the iron mineral can be enriched from a silicate-containing iron ore by inverse flotation.
- This kind of froth is carried out in the presence of a depressing agent for the iron mineral and collecting agent, which can contain hydrophobic amines, for instance alkyl ether amines and / or alkyl ether diamines.
- a depressing agent for the iron mineral and collecting agent can contain hydrophobic amines, for instance alkyl ether amines and / or alkyl ether diamines.
- hydrophobic amines for instance alkyl ether amines and / or alkyl ether diamines.
- Alkoxy unit should contain 8-10 carbon atoms and should be branched.
- WO 2008/077849 (AKZO NOBEL NV, publication date 3 July 2008) describes a collecting composition for use in enriching an iron mineral from a silicate containing iron or containing coarse silicates having a K 80 value of at least 1 10 ⁇ by reverse flotation of the ore.
- X is an aliphatic alkylene group containing 2 to 6 carbon atoms
- Z is an aliphatic alkylene group containing 2 to 6 carbon atoms
- Y " is an anion
- R is an aliphatic iso C13H27- group with average branching degree ranging from 1.5 to 3.5.
- the X and Z aliphatic alkylene groups may each independently be linear or branched when containing 3 to 6 carbon atoms.
- the present invention also relates to the use of at least one of the compounds of formulae (la), (lb), (lla), and/or (lib) as flotation collectors for enriching an iron mineral from a silicate-containing iron ore.
- any of the compounds of formulae (la), (lb), (lla) or (lib) provide improved results in enriching the iron material.
- Preference may be given to using a combination of these compounds.
- an alkyl ether amine compound (la) may be used in combination with a protonated alkyl ether amine compound (lb).
- an alkyl ether diamine compound (lla) may be used in combina- tion with a protonated alkyl ether diamine compound (lib). It may also be desirable to use a combination of all four compounds of formulae (la), (lb), (lla), and (lib).
- the invention further relates to compositions suitable for use in enriching an iron mineral from a silicate-containing iron ore comprising of at least one of the compounds of formulae (la), (lb), (lla), and/or (lib).
- compositions suitable for use in enriching an iron mineral from a silicate-containing iron ore comprising of at least one of the compounds of formulae (la), (lb), (lla), and/or (lib).
- the use of said formulations as collecting formulations for enriching an iron mineral from a silicate-containing iron ore is also claimed.
- Compositions containing a combination of these compounds as recited above may also be used.
- the invention also relates to a process for enriching an iron mineral from a silicate containing iron ore by inverse flotation using a collector comprising at least one of the compounds of formulae (la), (lb), (I la) , and/or (lib) or a collector formulation com- prising compositions comprising of at least one of the compounds of formulae (la), (lb), (Ma), and/or (lib).
- the compounds of formulae (la), (lb), (I la), and/or (lib) are used as collectors or in collector formulations in an inverse flotation process a much better selection removal of silicate is achieved by comparison to commercially available or other known alkyl ether amines or other known collectors.
- the present invention provides improved removal of silicate without suffering an increased loss of the iron mineral.
- the collectors of the present invention enable a higher proportion of the iron to be retained and a higher proportion of the silicate to be removed.
- X is an aliphatic alkylene group containing between 2 and 4 carbon atoms and especially three carbon atoms. It is particularly preferred that the alkylene group has the structure -CH2CH2CH2-.
- Z is an aliphatic alkylene group containing between 2 and 4 carbon atoms and especially 3 carbon atoms. It is particularly preferred alkylene group has the structure -CH2CH2CH2-.
- the anion Y " in formulae (lb) and (l ib) may be any suitable anion including a carboxy- late, sulphate, sulphonate, chloride, bromide, iodide, fluoride, nitrate, phosphate etc.
- the anion is a carboxylate particularly an aliphatic or olefinic carboxylate of between 1 and 6 carbon atoms. More preferably the carboxylate is an aliphatic carboxylate of between 1 and 3 carbon atoms such as HC0 2 " , CH 3 C0 2 " , CH 3 CH2CO2 " . CH 3 C0 2 " is especially preferred.
- the R group of compounds of formulae (la), (lb), (I la) , and/or (lib) is an aliphatic iso C1 3 H27- group with average branching degree ranging from 1.5 to 3.5.
- the degree of branching is defined as the number of methyl groups in one molecule of R group minus 1.
- the average degree of branching is the statistical mean of the degree of branching of the molecules of a sample.
- the mean number of methyl groups in the molecules of a sample can easily be determined by 1 H-NMR spectroscopy. For this purpose, the signal area corresponding to the methyl protons in the 1 H-NMR spectrum of a sample is di- vided by three and then divided by the signal area of the methylene protons of the CH 2 0-X group divided by two.
- the average degree of branching is between 2.0 and 3.0, more preferably between 2.0 and 2.5.
- an alcohol ROH in which the R group is as defined previously can suitably be reacted with an ethylenically unsaturated nitrile containing between 3 and 6 carbon atoms to provide an alkyl ether nitrile.
- Suitable ethylenically unsaturated nitriles include acrylonitrile, methacrylonitrile, ethacrylonitrile, 2-n-propylacrylonitrile, 2-iso- propylacrylonitrile, 2-methyl-1-butenenitrile, 3-methyl-1-butenenitrile, 2,2-dimethyl-1- butenenitrile, 2,3-dimethyl-1-butenenitrile, 2-ethyl-1-butenenitrile, 3-ethyl-1-butenenitrile, 2-methyl-1-butenenitrile, 3-methyl-1-butenenitrile, 2,3-dimethyl-1-butenenitrile, 2-ethyl-1- butenitrile, 1-pentenenitrile, 2-methyl-1-pentenenitrile, 3-methyl-1-pentenenitrile, 4- methyl-1-pentenenitrile.
- the ethylenically unsaturated nitrile would contain three carbon atoms i.e. acrylonitrile. It may be desirable to carry out this step in the presence of a base and a polar solvent.
- the base may be an alkali metal alkox- ide, preferably an alkali metal ethoxide or alkali metal methoxide, especially sodium methoxide.
- the ethylenically unsaturated nitrile may be added in an equivalent molar quantity to the alcohol. Usually the ethylenically unsaturated nitrile could also be added in a stoichiometric excess in order to ensure that all of the alcohol is reacted.
- the molar ratio of the ethylenically unsaturated nitrile to the alcohol can be above 1 : 1 and up to 10: 1 , preferably from 1 : 1 to 5: 1 , more desirably between 1 : 1 and 2 :1.
- the alcohol ROH may be obtained commercially from BASF or prepared according to the teaching of US6963014B (BASF AG, publication date 8 November 2005). It may be desirable to combine the ethylenically unsaturated nitrile with the alcohol already containing the base over a period of between 5 minutes and 75 minutes or more, It may be desirable to control the rate of combining the nitrile with the alcohol in order to ensure an optimum temperature is achieved.
- the reaction temperature may be between 10°C and 60°C. It may be desirable to control the temperature such that it does not exceed 50°C.
- the reaction time may be over a period of at least 5 minutes and as long as 24 hours. Typically the reaction will be at least 5 minutes and often as much as 10 hours or more.
- the ethylenically unsaturated nitrile may be removed under vacuum with a reduced pressure of between 15 mbar and 100 mbar at an elevated temperature of between 30°C and 60°C for a period of between 30 minutes and 180 minutes and optionally at an increased temperature of at least 65°C and up to 85°C.
- a resin to remove any trace amounts of the nitrile.
- the resulting alkyl ether nitrile should have a purity of at least 90% and often at least 95%.
- nitrile group of the alkyl ether nitrile of step one is reduced to the corresponding amine.
- This can be achieved by any conventional process for the reduction of nitriles to amines.
- the alkyl ether nitrile should be reacted with hydrogen in the presence of a suitable catalyst.
- a suitable catalyst includes Raney-Cobalt. This may be carried out in the presence of a suitable aprotic solvent such as tetrahydrofuran.
- the reaction may be carried out at elevated temperatures, for instance at least 80°C, desirably at least 90°C, and possibly up to 140°C or more.
- the reaction would be carried out at temperatures of between 100°C and 130°C.
- it may often be desirable to carry out process under increased pres- sure usually of at least 40 bar or more, for instance at least 45 bar. It may often be desirable to increase the pressure to even higher levels for instance up to 350 bar or higher, for instance between 250 bar and 300 bar.
- At the end of the reaction it may usually be desirable to remove the catalyst. This can be done by conventional filtration means.
- the resulting alkyl ether amine should have a purity of at least 85% and often at least 89% or 90% or higher.
- an alcohol ROH in which the R group is as defined previously can suitably be reacted with 1 eq of alkylene oxide like ethylene oxide, propylene oxide, 1 ,-2- butylene oxide, 2,3-butylene oxide, 1 ,2-pentene oxide and/or 1 ,2-hexene oxide. Therefore alcohol ROH is mixed with a base like sodium hydroxide, potassium hydroxide or cesium hydroxide or aqueous solution out of it and reaction water is removed under reduced vacuum (15 to 100 mbar) at elevated temperature (80 - 120°C) for suitable time. This could last between 0.5 and 3 hours. Reaction vessel is then flushed several times with nitrogen and heated to 100 - 160°C.
- Alkylene oxide is added in such a way that reaction temperature does not exceed 180°C.
- base can be neutralized with an acid (for example acetic acid) and resulting salt can be removed by simple filtration.
- Reaction leads to a mixture of showing a molecular weight distribution with an average alkoxylation degree of 1.
- Alkoxylation reaction can also be catalyzed by amines like imi- dazol or tertiary amines or double metal catalysts.
- product from reaction before can be mixed with a suitable catalyst optionally in presence of an aprotic solvent like tetrahydrofurane.
- Reaction vessel is flushed several times with nitrogen in order to remove air.
- ammonia (1 - 200 eq) and hydrogen (4 - 200 eq) are added up to a pressure of 50 bar.
- Reaction is heated under stirring to 200°C. Pressure should be kept below 280 bar.
- Further hydrogen is added (in case of pressure drop) and stirred over a period up to 24 h.
- Reaction is cooled to 40°C, gas is removed and vessel flushed several times with nitrogen. Catalyst can be removed by filtration and solvent can be removed under vacuum. Conversion of alcohol group into a primary amino group is at least 85% or even higher.
- the compound of formula (lb) may conveniently be prepared by addition of an acidic compound to the corresponding alkyl ether amine of formula (la).
- the acid compound will protonate the amine group and then the negatively charged acid radical will form the negatively charged Y " component.
- the acidic compound may be any suitable acid, for instance acids whose radicals are selected from the group consisting of carboxylate, sulphate, sulphonate, chloride, bromide, iodide, fluoride, nitrate, and phosphate.
- the acid is a carboxylic acid, particularly an aliphatic or olefinic carboxylic acid having between one and six carbon atoms. More preferably a carboxylic acid is an aliphatic carboxylic acid having between one and three carbon atoms i.e. formic acid, acetic acid or propionic acid. Acetic acid is preferred.
- the acidic compound may be added in a molar equivalence to the alkyl ether amine compound of formula (la). It may be desirable to add a lesser amount of the acidic compound which will result in partial protonation and therefore result in a mixture of the protonated compound of formula (lb) and the corresponding alkyl ether amine compound of formula (la). It may also be desirable to add a greater amount of the acidic compound resulting in a stoichiometric excess of the acidic compound. Typically the ratio of acidic compound to alkyl ether amine may be between 1 : 10 and 1.5:1 , especially between 1 :7 and 1 :1.
- the acidic compound may be added over a period of time between one minute and 45 minutes to the alkyl ether amine, for instance between five minutes and 30 minutes.
- the resulting compound of formula (lb) desirably will form as a homogenous solution which will remain clear and liquid during storage.
- the alkyl ether diamine of formula (I la) may be synthesised by reacting the alkyl ether amine of formula (la) with an ethylenically unsaturated nitrile containing between 3 and 6 carbon atoms to provide an alkyl ether amino alkyl nitrile.
- Suitable ethylenically unsatu- rated nitriles include acrylonitrile, methacrylonitrile, ethacrylonitrile, 2-n- propylacrylonitrile, 2-iso-propylacrylonitrile, 2-methyl-1-butenenitrile, 3-methyl-1- butenenitrile, 2,2-dimethyl-1-butenenitrile, 2,3-dimethyl-1-butenenitrile, 2-ethyl-1- butenenitrile, 3-ethyl-1-butenenitrile, 2-methyl-1-butenenitrile, 3-methyl-1-butenenitrile, 2,3-dimethyl-1-butenenitrile, 2-ethyl-1-butenitrile, 1-pentenenitrile, , 2-methyl-1- pentenenitrile, 3-methyl-1-pentenenitrile, 4-methyl-1-pentenenitrile.
- the ethylenically unsaturated nitrile would contain three carbon atoms i.e.
- the ethylenically unsaturated nitrile may be added in an equivalent molar quantity to the alkyl ether amine. Usually the ethylenically unsaturated nitrile should be added in a stoichiometric excess in order to ensure that all of the alkyl ether amine is reacted. Often the molar ratio of the ethylenically unsaturated nitrile to the amine can be above 1 : 1 and up to 10: 1 , preferably from 1.5:1 to 5: 1 , more desirably between 2: 1 and 4: 1.
- reaction temperature may be between 20°C and 60°C. It may be desirable to control the temperature such that it does not exceed 50°C.
- reaction time may be over a period of at least 10 minutes and as long as 24 hours. Typically the reaction will be at least 30 minutes and often as much as 7 hours or more.
- the ethylenically unsaturated nitrile may be removed under vacuum with a reduced pressure of between 15 mb and 25 mb at an elevated temperature of between 40°C and 60°C for a period of between 30 minutes and 60 minutes and optionally at an increased temperature of at least 65°C and up to 85°C.
- a resin to remove any trace amounts of the nitrile.
- the resulting alkyl ether amino alkyl nitrile should have a purity of at least 55% and often at least 60%
- nitrile group of the alkyl ether amino alkyl nitrile of step one is reduced to the corresponding amine.
- This can be achieved by any conven- tional process for the reduction of nitriles to amines.
- the alkyl ether amino alkyl nitrile should be reacted with hydrogen in the presence of a suitable catalyst.
- suitable catalysts includes Raney-Cobalt. This may be carried out in the presence of a suitable aprotic solvent such as tetrahydrofuran.
- the reaction may be carried out at elevated temperatures, for instance at least 80°C, desirably at least 100°C, and possibly up to 140°C or more.
- the reaction would be carried out at temperatures of between 1 10°C and 130°C.
- it may often be desirable to carry out process under increased pressure usually of at least 40 bar or more, for instance at least 45 bar. It may often be desirable to increase the pressure to even higher levels for instance up to 350 bar or higher, for instance between 250 bar and 300 bar.
- At the end of the reaction it may usually be desirable to remove the catalyst. This can be done by conventional filtration means.
- the resulting alkyl ether diamine should have a purity of at least 55% and often at least 60% or higher.
- the compound of formula (lib) may conveniently be prepared by addition of an acidic compound to the corresponding alkyl ether amine of formula (la).
- the acid the compound will protonate the amine group and then the negatively charged acid radical will form the negatively charged Y " component.
- the acidic compound may be any suitable acid, for instance acids whose radicals are selected from the group consisting of car- boxylate, sulphate, sulphonate, chloride, bromide, iodide, fluoride, nitrate, and phos- phate.
- the acid is a carboxylic acid, particularly an aliphatic or olefinic carboxylic acid having between one and six carbon atoms.
- a carboxylic acid is an aliphatic carboxylic acid having between one and three carbon atoms i.e. formic acid, acetic acid or propionic acid. Acetic acid is preferred.
- the acidic compound may be added in a molar equivalence to the alkyl ether diamine compound of formula (lla). It may be desirable to add a lesser amount of the acidic compound which will result in partial protonation and therefore result in a mixture of the protonated compound of formula (lib) and the corresponding alkyl ether diamine compound of formula (lla). It may also be desirable to add a greater amount of the acidic compound resulting in a stoichiometric excess of the acidic compound.
- the ratio of acidic compound to alkyl ether diamine may be between 1 :25 and 1.5: 1 , especially between 1 :20 and 1 :1.
- the acidic compound may be added drop wise over a period of time between one minute and 30 minutes to the alkyl ether amine, for instance between five minutes and 15 minutes.
- the resulting compound of formula (lib) desirably will form as a homogenous solution which will remain clear and liquid during storage.
- inverse flotation plant equipment In the process according to the invention for enriching an iron mineral from a silicate containing iron ore by inverse flotation conventional inverse flotation plant equipment may be used.
- the iron ore can be combined with water or suitable aqueous liquid and mixed using mechanical mixing means to form a homogenous slurry.
- the flotation process is normally carried out in one or more flotation cells.
- the collector would normally be introduced into the slurry in the flotation cell. Typically the collector will condition the dispersed iron ore of the slurry. A suitable period of conditioning will tend to be at least one minute and sometimes as much as 10 or 15 minutes.
- air would tend to be injected into the base of the flotation cell and the air bubbles so formed would tend to rise to the surface and generate a froth on the surface.
- the injection of air may be continued until no more froth is formed, which may be for at least one minute and as much as 15 or 20 minutes.
- the froth can be collected and removed.
- the flotation process may be performed in a conventional pH range. This may be in the range of between 5 and 12, such as 9 and 1 1. This tends to provide that the minerals would exhibit the correct surface charge.
- a conventional depressing agent such as a hydrophilic polysaccharide
- a hydrophilic polysaccharide may be used in a conventional quantity sufficient to cover the iron or surface in the requisite amount.
- a suitable hydrophilic polysaccharide includes different kinds of starches.
- Examples of conventional from regulators include methylisobutyl carbinol and alcohols having between six and 12 carbon atoms, such as ethylhexanol, and alkoxylated alcohols.
- Further conventional additives may be included in the flotation system, such as pH regulating agents, co-collectors, and extender oils.
- the typical ores of iron suitable for treatment according to the invention include haematite and magnetite ores.
- the invention is particularly suitable to haematite.
- the invention is suitable for processing of iron ores, for instance haematites containing high silica contents, for instance at least 20% by weight of iron ore, often at least 30%, and even at least 40% or more, for instance up to 60 % or 70% or more.
- Tridekanol N 300 g, 1.5 mol was stirred with NaOMe (30% solution in MeOH, 2.25 g, 0.013 mol at 21 °C.
- acrylonitrile 159 g, 3.0 mol was added during 45 min in such a way that temperature was kept below 50°C. Reaction was stirred overnight. Excess of acrylonitrile was removed under vacuum (20 mbar) at 50°C (and later at 75°C) within 30 min.
- Ambosol (3 weight%) was added and mixture was filtrated (900 k Seitz filter). According to gas chromatogram (GC) mixture contains 3.5% Tridekanol N and 96.4% addition product.
- TDN-oxypropylamine 150 g, 0.583 mol was stirred in a flask at room temperature.
- Acetic acid 7 g, 0.1 17 mol was added drop-wise and stirred for 10 min. A homogeneous solution was observed, which stayed clear and liquid during storage for >6 months.
- Tridecyloxypropylamine based on TDN (74 g, 0.28 mol) was stirred in a round bottom flask at 21 °C.
- Acrylonitrile (16 g, 0.30 mol) was added during 15 min in such a way that temperature was kept below 50°C. Reaction was stirred for 3 h. Excess of acrylonitrile was removed under vacuum (20 mbar) at 50°C (and later at 75°C) within 30 min.
- TDN-oxypropyl-1 ,3-propandiamine (314 g, 1.0 mol) was stirred in a flask at room tem- perature.
- Acetic acid (3 g, 0.05 mol) was added drop-wise and stirred for 10 min. A homogeneous solution was observed, which stayed clear and liquid during storage for >6 months.
- # average branching degree ranging from 2.0 to 2.4.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Compounds Of Iron (AREA)
Abstract
Description
Claims
Priority Applications (13)
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KR1020137029857A KR20140093608A (en) | 2011-04-13 | 2012-04-10 | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore |
MX2013011815A MX352083B (en) | 2011-04-13 | 2012-04-10 | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore. |
CN201280018151.9A CN103501915A (en) | 2011-04-13 | 2012-04-10 | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore |
ES12713724.8T ES2669969T3 (en) | 2011-04-13 | 2012-04-10 | Reverse foam flotation process for the separation of silicate from iron ore with amine and diamine compounds |
US14/110,646 US9561512B2 (en) | 2011-04-13 | 2012-04-10 | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore |
EA201391471A EA024454B1 (en) | 2011-04-13 | 2012-04-10 | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore |
EP12713724.8A EP2696985B1 (en) | 2011-04-13 | 2012-04-10 | Inverse froth flotation process for the separation of silicate from iron ore with amine and diamine compounds |
BR112013026095-5A BR112013026095B1 (en) | 2011-04-13 | 2012-04-10 | process to enrich an iron mineral from an iron ore containing silicate |
AU2012242041A AU2012242041A1 (en) | 2011-04-13 | 2012-04-10 | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore |
JP2014504268A JP2014517818A (en) | 2011-04-13 | 2012-04-10 | Amine and diamine compounds and their use for reverse flotation of silicates from iron ore |
CA2831157A CA2831157C (en) | 2011-04-13 | 2012-04-10 | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore |
UAA201313165A UA112865C2 (en) | 2011-04-13 | 2012-10-04 | AMINES AND DIAMINES AND THEIR APPLICATIONS FOR IRON OIL MIXTURE FLOATING SILICATE FLOTATION |
ZA2013/08448A ZA201308448B (en) | 2011-04-13 | 2013-11-11 | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore |
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US201161474756P | 2011-04-13 | 2011-04-13 | |
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US (1) | US9561512B2 (en) |
EP (1) | EP2696985B1 (en) |
JP (1) | JP2014517818A (en) |
KR (1) | KR20140093608A (en) |
CN (1) | CN103501915A (en) |
AU (1) | AU2012242041A1 (en) |
BR (1) | BR112013026095B1 (en) |
CA (1) | CA2831157C (en) |
EA (1) | EA024454B1 (en) |
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MX (1) | MX352083B (en) |
WO (1) | WO2012139985A2 (en) |
ZA (1) | ZA201308448B (en) |
Cited By (6)
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US10376901B2 (en) * | 2014-09-18 | 2019-08-13 | Akzo Nobel Chemicals International B.V. | Use of branched alcohols and alkoxylates thereof as secondary collectors |
WO2019243058A2 (en) | 2018-06-19 | 2019-12-26 | Clariant International Ltd | Use of polyols for improving a process for reverse froth flotation of iron ore |
WO2020007773A1 (en) | 2018-07-03 | 2020-01-09 | Nouryon Chemicals International B.V. | Collector composition containing biodegradable compound and process for treating siliceous ores |
WO2020221685A1 (en) | 2019-04-30 | 2020-11-05 | Basf Se | Method for flotation of a silicate-containing iron ore with a cationic collector |
WO2021140166A1 (en) | 2020-01-09 | 2021-07-15 | Basf Se | Method for flotation of a phosphate-containing ore |
WO2023180027A1 (en) | 2022-03-25 | 2023-09-28 | Clariant International Ltd | Novel cationic collectors for improving a process for froth flotation of silicates |
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CN104624383B (en) * | 2014-12-09 | 2017-02-01 | 鞍钢集团矿业有限公司 | Hematite reverse flotation inhibitor and preparation and use method thereof |
CN104689924B (en) * | 2015-02-28 | 2017-02-22 | 东北大学 | Amphoteric combined collector for reverse flotation of hematite iron ore |
AU2017291956A1 (en) | 2016-07-08 | 2019-01-17 | Akzo Nobel Chemicals International B.V. | Process to treat magnetite ore and collector composition |
WO2018039570A1 (en) * | 2016-08-26 | 2018-03-01 | Ecolab USA, Inc. | Sulfonated modifiers for froth flotation |
CN115228616B (en) * | 2022-08-09 | 2024-04-19 | 东北大学 | Iron ore normal-temperature reverse flotation method without adjusting pH value |
CN115318444B (en) * | 2022-08-30 | 2023-07-21 | 淄博坤鑫选矿药剂有限公司 | Amine or amine salt collecting agent with adjustable quantity of alkoxy chains for iron ore flotation, preparation method and compound application thereof |
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US10376901B2 (en) * | 2014-09-18 | 2019-08-13 | Akzo Nobel Chemicals International B.V. | Use of branched alcohols and alkoxylates thereof as secondary collectors |
WO2019243058A2 (en) | 2018-06-19 | 2019-12-26 | Clariant International Ltd | Use of polyols for improving a process for reverse froth flotation of iron ore |
WO2020007773A1 (en) | 2018-07-03 | 2020-01-09 | Nouryon Chemicals International B.V. | Collector composition containing biodegradable compound and process for treating siliceous ores |
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Also Published As
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JP2014517818A (en) | 2014-07-24 |
US20140048455A1 (en) | 2014-02-20 |
CA2831157C (en) | 2019-08-27 |
KR20140093608A (en) | 2014-07-28 |
MX2013011815A (en) | 2013-10-25 |
BR112013026095B1 (en) | 2021-04-20 |
CN103501915A (en) | 2014-01-08 |
BR112013026095A2 (en) | 2016-12-27 |
EP2696985B1 (en) | 2018-02-21 |
MX352083B (en) | 2017-11-08 |
EP2696985A2 (en) | 2014-02-19 |
EA201391471A1 (en) | 2014-04-30 |
WO2012139985A3 (en) | 2013-01-17 |
ZA201308448B (en) | 2015-04-29 |
AU2012242041A1 (en) | 2013-10-24 |
US9561512B2 (en) | 2017-02-07 |
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