US3363758A - Use of primary aliphatic ether amine acid salts in froth flotation process - Google Patents
Use of primary aliphatic ether amine acid salts in froth flotation process Download PDFInfo
- Publication number
- US3363758A US3363758A US600054A US60005466A US3363758A US 3363758 A US3363758 A US 3363758A US 600054 A US600054 A US 600054A US 60005466 A US60005466 A US 60005466A US 3363758 A US3363758 A US 3363758A
- Authority
- US
- United States
- Prior art keywords
- ether
- propyl
- amine
- propylene diamine
- silica
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 aliphatic ether amine Chemical class 0.000 title description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 65
- 239000002253 acid Substances 0.000 title description 39
- 150000003839 salts Chemical class 0.000 title description 29
- 238000000034 method Methods 0.000 title description 23
- 238000009291 froth flotation Methods 0.000 title description 20
- 230000008569 process Effects 0.000 title description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 56
- 239000000377 silicon dioxide Substances 0.000 description 30
- 229910052742 iron Inorganic materials 0.000 description 26
- 239000003153 chemical reaction reagent Substances 0.000 description 20
- 239000012141 concentrate Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229910052500 inorganic mineral Inorganic materials 0.000 description 17
- 239000011707 mineral Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 9
- 238000005188 flotation Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- DHIBIUNZWFPELU-UHFFFAOYSA-N 3-(8-methylnonoxy)propan-1-amine Chemical compound CC(C)CCCCCCCOCCCN DHIBIUNZWFPELU-UHFFFAOYSA-N 0.000 description 3
- BOKTVFODBQQGIH-UHFFFAOYSA-N 3-(8-methylnonoxy)propylazanium;acetate Chemical compound CC(O)=O.CC(C)CCCCCCCOCCCN BOKTVFODBQQGIH-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004435 Oxo alcohol Substances 0.000 description 3
- 159000000021 acetate salts Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- HBRNMIYLJIXXEE-UHFFFAOYSA-N dodecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN HBRNMIYLJIXXEE-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- MEGISDIUXPJRNH-UHFFFAOYSA-N 3-(3-methylheptoxy)propan-1-amine Chemical compound CC(CCOCCCN)CCCC MEGISDIUXPJRNH-UHFFFAOYSA-N 0.000 description 1
- WNESQTLZVOTCIL-UHFFFAOYSA-N 3-(6-methylheptoxy)propan-1-amine Chemical compound CC(C)CCCCCOCCCN WNESQTLZVOTCIL-UHFFFAOYSA-N 0.000 description 1
- RIFABNABTLCERU-HZJYTTRNSA-N 3-[(9Z,12Z)-octadeca-9,12-dienoxy]propan-1-amine Chemical compound C(CCCCCCC\C=C/C\C=C/CCCCC)OCCCN RIFABNABTLCERU-HZJYTTRNSA-N 0.000 description 1
- WLEVCAPGVKRUIK-KTKRTIGZSA-N 3-[(z)-octadec-9-enoxy]propan-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCN WLEVCAPGVKRUIK-KTKRTIGZSA-N 0.000 description 1
- TWXCJZHSMRBNGO-UHFFFAOYSA-N 3-decoxypropan-1-amine Chemical compound CCCCCCCCCCOCCCN TWXCJZHSMRBNGO-UHFFFAOYSA-N 0.000 description 1
- AGFZAZKFCMPYGS-UHFFFAOYSA-N 3-docosoxypropan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCOCCCN AGFZAZKFCMPYGS-UHFFFAOYSA-N 0.000 description 1
- ZRJOUVOXPWNFOF-UHFFFAOYSA-N 3-dodecoxypropan-1-amine Chemical compound CCCCCCCCCCCCOCCCN ZRJOUVOXPWNFOF-UHFFFAOYSA-N 0.000 description 1
- HPIKNEFNXLGDDK-UHFFFAOYSA-N 3-hexadecoxypropan-1-amine Chemical compound CCCCCCCCCCCCCCCCOCCCN HPIKNEFNXLGDDK-UHFFFAOYSA-N 0.000 description 1
- NWGJTXNNXLHFSE-UHFFFAOYSA-N 3-hexoxypropan-1-amine Chemical compound CCCCCCOCCCN NWGJTXNNXLHFSE-UHFFFAOYSA-N 0.000 description 1
- RESBJBYIDKHFGE-UHFFFAOYSA-N 3-icosoxypropan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCOCCCN RESBJBYIDKHFGE-UHFFFAOYSA-N 0.000 description 1
- ZINQYRQLEDIWQS-UHFFFAOYSA-N 3-nonoxypropan-1-amine Chemical compound CCCCCCCCCOCCCN ZINQYRQLEDIWQS-UHFFFAOYSA-N 0.000 description 1
- GWOUPOJUVSKJCH-UHFFFAOYSA-N 3-octadecoxypropan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCOCCCN GWOUPOJUVSKJCH-UHFFFAOYSA-N 0.000 description 1
- RDCAZFAKCIEASQ-UHFFFAOYSA-N 3-octoxypropan-1-amine Chemical compound CCCCCCCCOCCCN RDCAZFAKCIEASQ-UHFFFAOYSA-N 0.000 description 1
- FELNCSXBNJPZGU-UHFFFAOYSA-N 3-pentadecoxypropan-1-amine Chemical compound CCCCCCCCCCCCCCCOCCCN FELNCSXBNJPZGU-UHFFFAOYSA-N 0.000 description 1
- JPNCZSADMGXVPA-UHFFFAOYSA-N 3-tridecoxypropan-1-amine Chemical compound CCCCCCCCCCCCCOCCCN JPNCZSADMGXVPA-UHFFFAOYSA-N 0.000 description 1
- HQVBETYGPZKIHW-UHFFFAOYSA-N 4-hexoxybutan-1-amine Chemical compound CCCCCCOCCCCN HQVBETYGPZKIHW-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
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 239000004440 Isodecyl alcohol Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000005586 carbonic acid group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000007278 cyanoethylation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052598 goethite Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 229910052595 hematite Inorganic materials 0.000 description 1
- 239000011019 hematite Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AEIXRCIKZIZYPM-UHFFFAOYSA-M hydroxy(oxo)iron Chemical compound [O][Fe]O AEIXRCIKZIZYPM-UHFFFAOYSA-M 0.000 description 1
- 230000006872 improvement Effects 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical class C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002367 phosphate rock Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 239000013638 trimer Substances 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
- 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
- B03D2203/00—Specified materials treated by the flotation agents; Specified applications
- B03D2203/02—Ores
Definitions
- This invention relates to the use of acid salts of primary aliphatic ether amines as silica collectors in the concentration of minerals by the froth flotation process.
- it relates to the use of acid salts of primary aliphatic ether amines, such as 3-isodecoxypropylamine acetate and N-tridecoxypropyl-1,3-propylene diamine monoacetate, as cationic silica collectors in froth flotation of iron ore.
- Froth flotation is a common process applied in the art of separating or concentrating minerals from ore or the like.
- the flotation process usually comprises grinding crushed ore, classifying the ground ore in water, treating the classified ore by flotation to concentrate one or more minerals While the remainder of the minerals of the ore remain behind in the water pulp, thickening and filtering the separated concentrate and thereafter treating the same for ultimate use of the separated minerals.
- a collector is added to the ore dispersed in the water and air is introduced into the pulp to form a froth, and the froth, containing those minerals that are not wetted and have an affinity for air bubbles, is Withdrawn.
- a host of selective collecting agents have been developed that are used for forming Water-repellent, airavid surfaces on one mineral or a class of minerals. These collectors are anionic or cationic, and while many of them have been used satisfactorily, they often are limited by their solubility and handling characteristics, selectivity, effectiveness, stability, cost, etc.
- an object of this invention is to use acid salts of primary aliphatic ether amines as collectors in the concentration of minerals by the froth flotation process.
- Another object is to use acid salts of primary aliphatic ether amines, such as 3-isodecoxypropylamine acetate, as cationic silica collectors in froth flotation of iron ore.
- acid salts of primary aliphatic ether amines are useful collectors or reagents in concentrating or separating minerals from ores by the froth flotation process.
- the acetate of 3-isodecoxypropylamine prepared by hydrogenating the reaction product of isodecyl alcohol and 3,363,758 Patented Jan. 16, 1968 acrylonitrile
- R-O-R'-NH The primary aliphatic ether amines useful in the practice of this invention (as salts) can be represented by the general formula R-O-R'-NH where R is a straight or branched chain aliphatic radical, preferably an alkyl radical, and R is a straight or branched chain alkylene group or linkage or R is the divalent radical:
- R is a hydrogen atom or a methyl group.
- the primary aliphatic ether amines are ether monoamines (and occasionally referred to as such hereinafter) having the subgenus formula RO-R"NH where R is as defined above and has 6 to 22 carbon atoms, preferably 8 to 12 carbon atoms, and R' is said alkylene linkage, preferably having 2 to 6 carbon atoms and more preferably 3; carbon atoms.
- the primary aliphatic ether amines are ether diamines (and occasionally referred to as such hereinafter or as N-aliphatic ether alkylene diamines) having the subgenus formula:
- R and R" are as defined above.
- the R in this subgenus formula has 1 to 13 or more carbon atoms and preferably 7 to 13 carbon atoms, and this R preferably is an alkyl group with 1 to 4 methyl branches, such as the alkyl group derived from an 0x0 alcohol or mixtures of such alcohols, e.g., isooctyl alcohol, 3,4,4-trimethyl l-hexanol, decyl alcohol, and tridecyl alcohol.
- the ether monoamine acid salts used as collectors in this invention are water-soluble (or water-dispersible) compounds which are liquid at room temperature or are solids with low melting points, properties which make them particularly suitable as reagents in the froth flotation process.
- the acid salts of these ether monoamines can be represented by the general formula:
- A is a solubilizing salt-forming anion of an acid
- n is an integer (preferably l, as will be the case where monobasic acids are used) equal to the valence of said anion.
- Representative anions of such salts include acetate, halides (such as chloride, bromide, and iodide), sulfate, nitrate, borate, carbonate, oxalate, sulfamate, phosphate, salicylate, and the like.
- Suflicient acid is used in neutralizing the ether monoamines to render them water dispersible. In some cases, only 25% neutralization will render the monoamines water dispersible.
- the acetate salts are preferred because they are less corrosive and have better water solubility.
- ether monoamines which can be used (as acid salts) in the practice of this invention and used as reagents in froth flotation include:
- 3n-octoxy (Z-methyl) propylamine 3-isooctoxypropylamine, 3-n-nonoxypropylamine, 3-n-decoxypropylamine, 3-n-dodecoxypropylamine, 3-n-tetradecoxypropyla'mine, 3-n-pentadecoxypropylamine, 3-n-hexadecoxypropylamine, 3-n-octadecoxypropylamine, 3-(9-n-octadecenoxy) propylamine, 3-(12-n-octa'decenoxy) propylamine, 3-n-eicosoxypropylamine, 3-n-docosoxypropylamine, 3-isodecoxypropylamine, 4-n-hexoxy-n-butylamine, 5-(4,6-diethyloctoxy) -3 -methylamylamine, 4- (3 -methyl-8-propyldodecoxy -2-ethyl
- the ether monoamines can be prepared by known methods of cyanoethylation of a primary aliphatic alcohol (ROH), or mixtures of such alcohols, including oxo alcohols, to prepare the corresponding ether nitriles and then hydrogenating the latter to prepare the correspond ing ether amines.
- ROH primary aliphatic alcohol
- the ether diamines used in this invention are liquids and have extremely low cloud points, generally below 0 C. They have relatively high nitrogen or amine content and low combining weight. They can be readily neutralized and used as acid salts, many of which salts are liquids and soluble or dispersible and stable in hard or soft water. Since the ether diamines contain two amine nitrogens, i.e., they contain a primary amine group and a secondary amine group, each ether diamine molecule can combine with one or two monovalent acid anions. So, in neutralizing the ether diamines with an acid having a monovalent anion, one to two moles of acid can be used per mole of ether diamine.
- R and R" are as defined above, and A is a solubilizing salt-forming monovalent acid anion, such as chloride, acetate, benzoate, etc.
- A is a solubilizing salt-forming monovalent acid anion, such as chloride, acetate, benzoate, etc.
- the above salt formula is the theoretical formula; actually, some of the secondary amine group is also neutralized to some extent.
- Monoacetates of these ether diamines are preferred because they will be liquid at room temperature in addition to being readily dispersible or soluble in aqueous systems.
- Inorganic or organic acids can be used in forming the salts from the free base ether amines.
- Common inorganic acids which can be used include phosphoric, nitric, boric, hydrochloric, hydrobromic and sulfuric acids.
- Organic acids which can be used include aliphatic monodior tri-carboxylic acids; lower alkyl carboxylic acids; monoor dihydroxy lower alkyl carboxylic acids and aminosubstituted compounds thereof; and unsaturated aliphatic acids.
- organic acids examples include formic, acetic, hydroxy acetic, propionic, butyric, isovaleric, glycolic, lactic, gluconic, amino acetic, protonic, malonic, succinic, glutaric, adipic, malic, tartaric, glutaric, maleic, fumaric, citric, isocitric aconitic, oxalic, salicyclic, sulfonic, carbonic, benzoic and naphthenic acids, and the like.
- Particularly useful, commercially available acids which can be used include fatty acids, either saturated or unsaturated with 14 to 18 carbon atoms, such as those derived from naturally occurring fats, and oils, such as soybean oil, coconut oil, tallow, tall oil, etc., as well as polymerized fatty acids such as dimer fatty acids (which are usually mixtures of dimer and trimer acids obtained by polymerizing linoleic acids, tall oil acids or soybean acids).
- Another useful commercially available group of acids which can be used are the Sunaptic Acids, which are monocarboxylic derivatives of naphthalene hydrocarbons, having average molecular formulas 19 34 2, 21 37 2, and 29 49 2-
- Representative ether diamines which can be used in the practice of this invention include:
- the alcohol used to form the ether diamines is a mixture of alcohols, as will be the case where commercial oxo alcohols are used.
- the ether diamines used in this invention can be prepared by reacting an aliphatic ether primary amine with acrylonitrile or methacrylonitrile and then hydrogenating the resulting aliphatic ether amine nitrile to produce the ether diamine.
- the aliphatic ether primary amines can themselves be prepared by hydrogenating the aliphatic ether nitriles produced by the reaction of a primary and/ or secondary aliphatic alcohol with acrylonitrile or methacrylonitrile.
- Alcohols which can be used for this purpose include methanol, isobutanol, etc. and higher alcohols.
- Particularly useful alcohols which can be used are the higher oxo alcohols produced by hydrogenation of oxoaldehydes which in turn are prepared by the oxonation reaction between an olefin, carbon-monoxide and hydrogen.
- the disclosure of the preparation of these ether diamines will be omitted in the interest of brevity, and further detail on such preparation is disclosed in copending application Ser. No. 519,531, filed Jan. 10, 1966, incorporated herein by reference.
- the amount of ether amine acid salt reagent used in the froth flotation process Will vary and be dependent upon such factors as the type of ore being treated, the amount of mineral to be collected, the degree of subdivision of such minerals, the degree of separation desired, and the particular ether amines used. Functionally expressed, the amount of ether amine acid salt reagent used in such froth flotation process will be that sufficient to achieve a desirable separation. Generally, the amount of ether amine acid salt used will be 0.05 to 2 pounds, preferably 0.1 to 0.3 pound, per ton of ore.
- the ether amine acid salt reagent can be employed as a solution or dispersion in water or other solvent and introduced into the ore pulp as such without prior conditioning or can be conditioned with the ore pulp prior to the actual concentration operation.
- the reagents of this invention can be used in conjunction with other conventional treating agents such as activators, frothing agents, depressing agents, dispersing agents, etc.
- One particular advantage of this invention is that when it is practiced to separate silica from iron ore, such as magnetite, eflective separation can be obtained without the necessity of using an iron depressant such as starch.
- the general well known technique of the froth flotation process is used. Briefly, the ore, or a concentrate of the ore, is ground and mixed with water to form a pulp. The pulp is placed in a suitable flotation cell or vessel provided with an agitator. Air is introduced into the pulp by means of a sparger and passes through the pulp. The froth that is formed is skimmed off or allowed to overflow. The silica floats away with the froth, leaving the mineral concentrate behind. In this manner, the silica or siliceous material is separated from the desired mineral.
- this invention is particularly applicable in removing silica from iron ore, such as magnetite, it can be used in concentrating any silica-containing minerals or ores, such as hematite, goethite, phosphate rock, etc.
- ether amine acid salts of this invention were evaluated as silica collector reagents in the froth flotation of magnetic iron concentrate obtained from the Mesabi Iron Range.
- the iron concentrate or feed used in Runs 1, 2 and 3 was ground so that passed through a 325 mesh standard sieve, and it contained about 63.5 weight percent iron and 10 weight percent silica.
- the iron concentrate feed used in Runs 4, 5 and 6 was ground so that passed through a 325 mesh standard sieve, and it contained 67.2 weight percent iron and 5.1 weight percent silica.
- the reagent used in Runs 1 and 5 comprised a primary C -C propyl ether amine acetate, having a total amine nitrogen (TAN) content of 6.68%, the sum of secondary and tertiary amine nitrogen in the material being 0.26%.
- TAN total amine nitrogen
- 20.97 grams of the ether amine was 50% neutralized with 3 grams of glacial acetic acid.
- Five grams of this neutralized ether amine was diluted with grams of water to prepare a 2.5% reagent dispersion.
- the reagents used in the other runs were prepared in the same manner, and the compositions of all of the reagents used are shown in Table I.
- collectors listed are readily dispersible in water as 50% acetate salts, these collectors have advantages and more versatility than conventional lauryl primary amines which are not readily dispersible in water unless completely or neutralized with acetic acid.
- Run 6 shows that N-tridccoxypropyl-1,3-propylene diamine monoacetate is also an effective silica flotation collector, its use resulting in good silica reduction with a high iron recovery.
- the C3-C10 propyl ether amine acetate of this invention is significantly more selective than the primary lauryl amine acetate. That is, the ether amine acetate of this invention will result in a concentrate lower in silica at an equal iron recovery, or a higher iron recovery at an equal silica content.
- the primary lauryl amine acetate is a stronger collector but not as selective as the ether amine acetate.
- the primary lauryl amine must be completely neutralized to make it readily dispersible in water, and even then it is a solid rather than a liquid salt and cannot be handled as easily.
- a froth flotation process for separating silica from an ore which comprises frothing said ore in the presence of an aqueous medium containing a water dispersible acid salt of an aliphatic ether diamine having the general formula where R is an aliphatic radical having 1-13 carbon atoms, and R" is a hydrogen atom or a methyl group and floating off the silica from said ore.
- a froth flotation process for separating silica from iron ore which comprises frothing said ore in an aqueous medium in the presence of 0.1 to 2 pounds per ton of said ore of a Water-dispersible, liquid aliphatic ether diamine salt having the general formula where R is an aliphatic radical having 7'-l3 carbon atoms, R" is hydrogen or methyl, and A is a solubilizing saltforming anion of monobasic acid and floating oil the silica from said ore.
- a froth flotation process for separating silica from an ore by subjecting said ore to froth flotation in the presence of a collecting agent to float off said silica, the improvement comprising using as the collecting agent an acid salt of an ether diamine having the general formula R-O-CH CH R) CH NHCH CI-I R CH -NH where R is an aliphatic radical having 1-l3 carbon atoms and R" is a hydrogen atom or a methyl group.
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Description
United States Patent 3,363,758 USE OF PRIMARY ALIPHATIC ETHER AMINE ACll) SALTS IN FROTH FLOTATION PRGCESS Alvin D. Cronberg, Bloomington, Clarence N. lmpola,
Prior Lake, and Thomas H. Lentz, Hopkins, Minn, assignors to Ashlantl Oil & Refining Company, Ashland, Ky., a corporation of Kentucky No Drawing. Filed Dec. 8, 1966, Ser. No. 600,054 8 Claims. (Cl. 209-166) ABSTRACT OF THE DISCLOSURE Acid salts of primary aliphatic ether amines, e.g., 3- isodecoxypropylamine acetate and N-tridecoxypropyl-L3- propylene diamine monoacetate, are used as silica collectors in the concentration of minerals by froth flotation.
This invention relates to the use of acid salts of primary aliphatic ether amines as silica collectors in the concentration of minerals by the froth flotation process. In a further aspect, it relates to the use of acid salts of primary aliphatic ether amines, such as 3-isodecoxypropylamine acetate and N-tridecoxypropyl-1,3-propylene diamine monoacetate, as cationic silica collectors in froth flotation of iron ore.
Froth flotation is a common process applied in the art of separating or concentrating minerals from ore or the like. Briefly, the flotation process usually comprises grinding crushed ore, classifying the ground ore in water, treating the classified ore by flotation to concentrate one or more minerals While the remainder of the minerals of the ore remain behind in the water pulp, thickening and filtering the separated concentrate and thereafter treating the same for ultimate use of the separated minerals. In carrying out the flotation step, a collector is added to the ore dispersed in the water and air is introduced into the pulp to form a froth, and the froth, containing those minerals that are not wetted and have an affinity for air bubbles, is Withdrawn.
A host of selective collecting agents have been developed that are used for forming Water-repellent, airavid surfaces on one mineral or a class of minerals. These collectors are anionic or cationic, and while many of them have been used satisfactorily, they often are limited by their solubility and handling characteristics, selectivity, effectiveness, stability, cost, etc.
Accordingly, an object of this invention is to use acid salts of primary aliphatic ether amines as collectors in the concentration of minerals by the froth flotation process. Another object is to use acid salts of primary aliphatic ether amines, such as 3-isodecoxypropylamine acetate, as cationic silica collectors in froth flotation of iron ore. Further objects and advantages of this invention Will become apparent to those skilled in the art from the follow ing description and accompanying claims.
Briefly, We have discovered that acid salts of primary aliphatic ether amines are useful collectors or reagents in concentrating or separating minerals from ores by the froth flotation process. For example, we have found that the acetate of 3-isodecoxypropylamine (prepared by hydrogenating the reaction product of isodecyl alcohol and 3,363,758 Patented Jan. 16, 1968 acrylonitrile) is an excellent cationic collector for the separation of silica and/ or other siliceous materials from iron ore such as magnetite in the froth flotation process.
The primary aliphatic ether amines useful in the practice of this invention (as salts) can be represented by the general formula R-O-R'-NH where R is a straight or branched chain aliphatic radical, preferably an alkyl radical, and R is a straight or branched chain alkylene group or linkage or R is the divalent radical:
RI! RI! I -otno 01121701120 cmwhere R" is a hydrogen atom or a methyl group. Where R is said alkylene linkage, the primary aliphatic ether amines are ether monoamines (and occasionally referred to as such hereinafter) having the subgenus formula RO-R"NH where R is as defined above and has 6 to 22 carbon atoms, preferably 8 to 12 carbon atoms, and R' is said alkylene linkage, preferably having 2 to 6 carbon atoms and more preferably 3; carbon atoms. Where R in the above general formula is said divalent radical, the primary aliphatic ether amines are ether diamines (and occasionally referred to as such hereinafter or as N-aliphatic ether alkylene diamines) having the subgenus formula:
where R and R" are as defined above. The R in this subgenus formula has 1 to 13 or more carbon atoms and preferably 7 to 13 carbon atoms, and this R preferably is an alkyl group with 1 to 4 methyl branches, such as the alkyl group derived from an 0x0 alcohol or mixtures of such alcohols, e.g., isooctyl alcohol, 3,4,4-trimethyl l-hexanol, decyl alcohol, and tridecyl alcohol.
The ether monoamine acid salts used as collectors in this invention are water-soluble (or water-dispersible) compounds which are liquid at room temperature or are solids with low melting points, properties which make them particularly suitable as reagents in the froth flotation process. The acid salts of these ether monoamines can be represented by the general formula:
where R and R' are as defined above, A is a solubilizing salt-forming anion of an acid, and n is an integer (preferably l, as will be the case where monobasic acids are used) equal to the valence of said anion. Representative anions of such salts include acetate, halides (such as chloride, bromide, and iodide), sulfate, nitrate, borate, carbonate, oxalate, sulfamate, phosphate, salicylate, and the like. Suflicient acid is used in neutralizing the ether monoamines to render them water dispersible. In some cases, only 25% neutralization will render the monoamines water dispersible. The acetate salts are preferred because they are less corrosive and have better water solubility.
Representative ether monoamines which can be used (as acid salts) in the practice of this invention and used as reagents in froth flotation include:
3-n-hexoxypropylamine, 3-(3-methylpentoxy) propylamine, 3-isohexoxypropyla1nine, 3-(2,3-dimethylbutoxy) propylamine, 3-n-heptoxypr0pylamine, 3-n-octoxypropylamine,
3n-octoxy (Z-methyl) propylamine, 3-isooctoxypropylamine, 3-n-nonoxypropylamine, 3-n-decoxypropylamine, 3-n-dodecoxypropylamine, 3-n-tetradecoxypropyla'mine, 3-n-pentadecoxypropylamine, 3-n-hexadecoxypropylamine, 3-n-octadecoxypropylamine, 3-(9-n-octadecenoxy) propylamine, 3-(12-n-octa'decenoxy) propylamine, 3-n-eicosoxypropylamine, 3-n-docosoxypropylamine, 3-isodecoxypropylamine, 4-n-hexoxy-n-butylamine, 5-(4,6-diethyloctoxy) -3 -methylamylamine, 4- (3 -methyl-8-propyldodecoxy -2-ethyl butylamine, 3-n-tridecoxypropylamine, 3-isodecoxypropylamine,
3 (3 ,4-dimethylhexoxy) propylamine, 3-(3,5-dimethylhexoxy) propylarnine, 3-(4,5-dimethylhexoxy) propylamine, 3-(3-methylheptoxy) propylamine, 3-(5-methylheptoxy) propylamine, 5-(3-n-butyl-5isooctylnonoxy) pentylamine, 4-(2,4,6-trimethyl-3-ethyltetradecoxyl) butylamine, 6-(3-n-pentyl-4-diethy1hexoxy) hexylamine, 3-lauroleyloxypropylamine, 3-myrestoleyloxypropylamine, 3-palmitoleyloxypropylamine, 3-oleyloxypropylamine, 3-ricinoleyloxypropylamine, 3-linoleyloxypropylamine, 3-linolenyloxypropylarnine, 3-eleostearyloxypropylarnine, 3-eiconyloxypropylamine, 3-gadoleyloxypropylamine, 3-arachidonyloxypropylamine,
and the like, including mixtures thereof, and their acid salts.
The ether monoamines can be prepared by known methods of cyanoethylation of a primary aliphatic alcohol (ROH), or mixtures of such alcohols, including oxo alcohols, to prepare the corresponding ether nitriles and then hydrogenating the latter to prepare the correspond ing ether amines.
The ether diamines used in this invention are liquids and have extremely low cloud points, generally below 0 C. They have relatively high nitrogen or amine content and low combining weight. They can be readily neutralized and used as acid salts, many of which salts are liquids and soluble or dispersible and stable in hard or soft water. Since the ether diamines contain two amine nitrogens, i.e., they contain a primary amine group and a secondary amine group, each ether diamine molecule can combine with one or two monovalent acid anions. So, in neutralizing the ether diamines with an acid having a monovalent anion, one to two moles of acid can be used per mole of ether diamine. In some cases, as low as 25% neutralization will render the diamines water dispersible. In any event, sutficient acid is used in neutralizing the diamine to render the same water dispersible, and preferably enough so that the salts are liquids. Where the diamine is to be 50% neutralized with an acid having a monovalent acid anion, one mole of the acid will be used per mole of ether diamine and the resulting salt will have the general formula:
where R and R" are as defined above, and A is a solubilizing salt-forming monovalent acid anion, such as chloride, acetate, benzoate, etc. (The above salt formula is the theoretical formula; actually, some of the secondary amine group is also neutralized to some extent.) Monoacetates of these ether diamines are preferred because they will be liquid at room temperature in addition to being readily dispersible or soluble in aqueous systems.
Inorganic or organic acids can be used in forming the salts from the free base ether amines. Common inorganic acids which can be used include phosphoric, nitric, boric, hydrochloric, hydrobromic and sulfuric acids. Organic acids which can be used include aliphatic monodior tri-carboxylic acids; lower alkyl carboxylic acids; monoor dihydroxy lower alkyl carboxylic acids and aminosubstituted compounds thereof; and unsaturated aliphatic acids. Examples of these organic acids include formic, acetic, hydroxy acetic, propionic, butyric, isovaleric, glycolic, lactic, gluconic, amino acetic, protonic, malonic, succinic, glutaric, adipic, malic, tartaric, glutaric, maleic, fumaric, citric, isocitric aconitic, oxalic, salicyclic, sulfonic, carbonic, benzoic and naphthenic acids, and the like. Particularly useful, commercially available acids which can be used include fatty acids, either saturated or unsaturated with 14 to 18 carbon atoms, such as those derived from naturally occurring fats, and oils, such as soybean oil, coconut oil, tallow, tall oil, etc., as well as polymerized fatty acids such as dimer fatty acids (which are usually mixtures of dimer and trimer acids obtained by polymerizing linoleic acids, tall oil acids or soybean acids). Another useful commercially available group of acids which can be used are the Sunaptic Acids, which are monocarboxylic derivatives of naphthalene hydrocarbons, having average molecular formulas 19 34 2, 21 37 2, and 29 49 2- Representative ether diamines which can be used in the practice of this invention include:
N-(methoxy-n-propyl)-l,3-propylene diamine;
N-(ethoxy-n-propyl) -1,3-propylene diamine;
N-(n-propoxy-n-propyl)-1,3 propylene diamine;
N-(isobutoXy-n-propy-l-l,3-propylene diamine;
N-(n-pentoxy-n-propyl)-l,3-propylene diamine;
N-(n-hexoxy-n-propyl) -l,3-propylene diamine;
N-(n-heptoxy-n-propyl) -1,3-propylene diamine;
N (3,4 dimethylhexoxy n propyl) 1,3 (2- methyl) -propylene diamine;
N-(n-heptenoxy-2-methylpropyl)-l,3-propylene diamine;
N (4 methyl 3 hexenoxy n propyl) 1,3 (2- methyl) -propylene diamine;
N-(n-octoxy-n-propyl)-1,3 propylene diamine;
N (3,4 dimethyl hexoxy n propyl) 1,3 (2- methyl) -propylene diamine;
N- (4-ethyl-hexenoxy-2-methylpropyl-1,3-(2-methyl)- propylene diamine;
N-( l-methylheptoxy-n-propyl l ,3 -propylene diamine;
N- 4,4-dirnethy'lhexoxy-n-propyl) l ,3-propylene diamine;
N-(6-methylheptoxy-n-propyl) -1,3-propylene diamine;
N-7-octenoxy-n-propyl) -1,3 Z-methyl) propylene diamine;
N- (3 -methyl-5-heptenoxy-n-propyl) l 3 -propylyene diamine;
N-(n-nonoxy-n-propyl)-l,3-propylene diamine;
N (4 methyl 3 ethyl hexoxy n propyl) 1,3-
propylene diamine;
N (2 ,3 dimethyl 4 heptenoxy 2 methylpropy1)- 1,3-propylene diamine;
N-(n-decoxy-n-propyl)-1,3-propylene diamine;
N (3,4,5 trimethylheptoxy n propyl) 1,3 (2- methyl) -propylene diamine;
N-(9-decenoxy-2-methylpropyl) -1,3-propylene diamine;
N (9 methyl 4,5 nonadienoxy n propyl) 1,3-
propylene diamine;
N-(n-hendecoxy-n-propyl)-1,3-propylene diamine;
N-9-methy1-decoxy-2-methylpropyl) 1, 3-propylene diamine;
N (9 hendecenoxy n propyl) 1,3 (2 methyl)- propylene diamine;
N-(3-n-propyl-octoxy-n-propyl)-1,3-propylene diamine;
N-(n-dodecoxy-n-propyl)-1,3-propylene diamine;
N (IO-methylhendecoxy 2 methylpropyl) 1,3-
propylene diamine;
N (8 methyl 6 ethylnonoxy n propyl) 1,3 (2- rnethyl)-propylene diamine;
N-(10-dodecenoxy-n-propyl)-1,3-propylene diamine;
N-(n-tridecoxy-n-propyl)-1,3-propylene diamine;
N (4,7,9 trimethyldecoxy n propyl) 1,3 (2- methyl) -propylene diarnine;
N (3,5,7,8 tetramethylnonoxy 2 methylpropyl)- 1,3-propylene diamine;
N-( l o-tridecenoxy-n-propyl)-1,3-propylene diamine;
N (4,8,12 trimethyl 11 decenoxy n propyl) 1,3-
propylene diamine;
N (8 11 propyl 5,9 decadienoxy 2 methylpropyl)-1,3-prop-y1ene diamine;
and the like. Mixtures of said ether diamine acid salts.
can be used, especial-1y where the alcohol used to form the ether diamines is a mixture of alcohols, as will be the case where commercial oxo alcohols are used.
The ether diamines used in this invention can be prepared by reacting an aliphatic ether primary amine with acrylonitrile or methacrylonitrile and then hydrogenating the resulting aliphatic ether amine nitrile to produce the ether diamine. The aliphatic ether primary amines can themselves be prepared by hydrogenating the aliphatic ether nitriles produced by the reaction of a primary and/ or secondary aliphatic alcohol with acrylonitrile or methacrylonitrile. Alcohols which can be used for this purpose include methanol, isobutanol, etc. and higher alcohols. Particularly useful alcohols which can be used are the higher oxo alcohols produced by hydrogenation of oxoaldehydes which in turn are prepared by the oxonation reaction between an olefin, carbon-monoxide and hydrogen. The disclosure of the preparation of these ether diamines will be omitted in the interest of brevity, and further detail on such preparation is disclosed in copending application Ser. No. 519,531, filed Jan. 10, 1966, incorporated herein by reference.
The amount of ether amine acid salt reagent used in the froth flotation process Will vary and be dependent upon such factors as the type of ore being treated, the amount of mineral to be collected, the degree of subdivision of such minerals, the degree of separation desired, and the particular ether amines used. Functionally expressed, the amount of ether amine acid salt reagent used in such froth flotation process will be that sufficient to achieve a desirable separation. Generally, the amount of ether amine acid salt used will be 0.05 to 2 pounds, preferably 0.1 to 0.3 pound, per ton of ore.
The ether amine acid salt reagent can be employed as a solution or dispersion in water or other solvent and introduced into the ore pulp as such without prior conditioning or can be conditioned with the ore pulp prior to the actual concentration operation. In addition, the reagents of this invention can be used in conjunction with other conventional treating agents such as activators, frothing agents, depressing agents, dispersing agents, etc. One particular advantage of this invention is that when it is practiced to separate silica from iron ore, such as magnetite, eflective separation can be obtained without the necessity of using an iron depressant such as starch.
In carrying out the practice of my invention, the general well known technique of the froth flotation process is used. Briefly, the ore, or a concentrate of the ore, is ground and mixed with water to form a pulp. The pulp is placed in a suitable flotation cell or vessel provided with an agitator. Air is introduced into the pulp by means of a sparger and passes through the pulp. The froth that is formed is skimmed off or allowed to overflow. The silica floats away with the froth, leaving the mineral concentrate behind. In this manner, the silica or siliceous material is separated from the desired mineral. Although this invention is particularly applicable in removing silica from iron ore, such as magnetite, it can be used in concentrating any silica-containing minerals or ores, such as hematite, goethite, phosphate rock, etc.
The following examples further illustrate the advantages and objects of this invention, but the various reagents, conditions of treatment, and other details recited in these examples should not be construed to unduly limit this invention.
Examples Several ether amine acid salts of this invention were evaluated as silica collector reagents in the froth flotation of magnetic iron concentrate obtained from the Mesabi Iron Range. The iron concentrate or feed used in Runs 1, 2 and 3 was ground so that passed through a 325 mesh standard sieve, and it contained about 63.5 weight percent iron and 10 weight percent silica. The iron concentrate feed used in Runs 4, 5 and 6 was ground so that passed through a 325 mesh standard sieve, and it contained 67.2 weight percent iron and 5.1 weight percent silica.
In Runs 1, 2 and 3, 500 grams of the concentrate was placed in a Fagergren Mineral Master laboratory flotation cell and diluted with sufiicient water to provide a water mixture containing 20 weight percent of the iron concentrate. The mixture was allowed to agitate in the cell for one minute, using an impeller speed of 1500 r.p.m. The reagent to be evaluated was then added to the agitating pulp in the cell, using in all cases 2 ml. of a 2 /2 percent solution of the reagent in water (0.2 lb./ton of iron concentrate). Twenty-five seconds after the reagent was added, 0.05 pound of methyl isobutyl carbinol per ton of feed was added as a frothing agent. Thirty seconds after the reagent was added, the air valve of the cell was opened, injecting air at the bottom of the cell and thus starting the flotation process, the pH of the pulp being 7.5-8. The froth product or tailings (containing the silica) was skimmed off. The tailings and concentrate products were then filtered in a filter press and baked overnight in a 300 F. oven. The dried products were then weighed and analyzed to determine the amount of iron and the amount of silica in each product. Runs 4, 5 and 6 were made in the same manner as described above, except that only 1 ml. of the 2 /2 percent reagent solution was added to the pulp and 0.06 lb. of pine oil per ton of feed was used. as the frothing agent. Results are summarized in the following Table II.
The reagent used in Runs 1 and 5 comprised a primary C -C propyl ether amine acetate, having a total amine nitrogen (TAN) content of 6.68%, the sum of secondary and tertiary amine nitrogen in the material being 0.26%. In preparing this reagent, 20.97 grams of the ether amine was 50% neutralized with 3 grams of glacial acetic acid. Five grams of this neutralized ether amine was diluted with grams of water to prepare a 2.5% reagent dispersion. The reagents used in the other runs were prepared in the same manner, and the compositions of all of the reagents used are shown in Table I.
TABLE I Analysis Percent Neutralized Run Amine used See. and Eqniwith ace- IAN, tert. valent tic acid percent amino N, 1 weight percent 1 Cs-Om propyl ether diainine. 6. 68 26 209. 7 50 2..- 3-isodecoxypropyl amine 6.04 O. ()0 229. 7 50 3... ..(l0 5. 56 0. 06 252. 0 50 4.-- Gig-Cm propyl ether diaminc. 6. 68 0.26 209. 7 100 -.(10 6. 68 0. 26 200. 7 50 6. N-tridccoxypropy11,3pr0- 7. 93 *3. 75 176. 5 50 pylene diamme.
*This figure is for secondary amino nitrogen only.
TABLE II Assay Units Amt. of Fe recovery, Run Collector used Product product, wt. percent wt. percent HCl insol., Fe, wt. H01 insol. Fe
wt. percent percent 1 (lg-Cm propyl ether amine acetate {C0ncentrate... 87. 78 7. 12 65. 67 6. 57. 65 9O 82 (50% neutralized). Taihngs 12.22 31. 1O 47. 68 3. 80 5. 83
2 3-is0dec0xypr0pyl amine acetate J Concentrate..- 79. 74 6.19 66. 25 4. 94 52. 84 l 83 neutralized). lTa1lings..- 20. 26 26.02 51. 78 5. 27 10. 48
3 3isododecoxypropyl amine acetate {Comma-ate... 80. 06 6. 45 66. 25 5. 16 53. O4 83 59 (50% neutralized). Tailings 19. 94 24. 42 52.22 4. 87 10. 41
4 Ola-Cm propyl ether amine acetate f Concentrate... 90. 97 3. 79 68. 12 3. 45 61. 97 92 2O (100% neutralized). LIa1l1ngs. 9.03 19. 65 56. 89 1. 77 5. 24
5 0 -010 propyl ether amine acetate {Concentrate... 87. 45 3. 13 68. 59 2. 74 60. 00 89 32 (50% neutralized). Tailu1gs... 12. 19.13 57. 26 2. 40 7.18
Ntridecoxypropyl1 3-propylene di- Concentrate..- 89. 51 3. 54 68.28 3. 17 61. 12 6 amine monoacetate. {Tailings 10. 49 19.65 56.88 2.06 5. 97 91-10 The data of Table II show that the ether amine salts of this invention are generally strong silica collectors with good selectivity. In the case of Run 1, the collector exhibited good selectivity and high iron recovery, though by using greater amounts of the collector the silica content in the concentrate could be reduced. In the case of Run 2, the collector exhibited good selectivity, good iron recovery, and strong collecting power. In the case of Run 3, though the selectivity was not as high, the collector exhibited good iron recovery and strong collecting power. In similar runs with secondary aliphatic ether amine and primary amine acetates, the concentrate was too high in silica content or the selectivity was lower, showing that the primary aliphatic ether amines of this invention are superior.
The results of Runs 4 and 5 show that the neutralization level of the amine has a significant effect on flotation performance. The 50% neutralized amine salt was a stronger collector than the 100% neutralized amine salt.
Since all of the collectors listed are readily dispersible in water as 50% acetate salts, these collectors have advantages and more versatility than conventional lauryl primary amines which are not readily dispersible in water unless completely or neutralized with acetic acid.
Run 6 shows that N-tridccoxypropyl-1,3-propylene diamine monoacetate is also an effective silica flotation collector, its use resulting in good silica reduction with a high iron recovery.
Another series of runs was made in which a conventional distilled primary lauryl amine 100% neutralized with acetic acid was compared with the C C propyl ether amine 100% neutralized with acetic acid (used in Run 4). These runs were made with varying reagent levels using the aforementioned procedure on an ore containing 10.3 weight percent silica and 64.5 weight percent iron. Table III shows the flotation concentrate grades and recoveries.
TABLE III Amt. of Amt. of Iron Run Collector used collector iron in HCl insol. recovery,
used, lb./ cone, wt. wt. percent percent ton conc. percent Primary lauryl amine acetate 0 05 68.85 7. 06 83. 2 (lo 0 10 68. 36 5.26 66. 1 (Ea-Cw propyl ether amine acetate.-. 0 05 65. 43 8. 44 92. 6 do 0 10 67. 03 6. 73 83. 8 do 0.20 68.15 5. 28 69. 2
If a plot is made of the percent silica remaining in the concentrate versus the percent Fe recovery, using the data of Table III, it would show that the C3-C10 propyl ether amine acetate of this invention is significantly more selective than the primary lauryl amine acetate. That is, the ether amine acetate of this invention will result in a concentrate lower in silica at an equal iron recovery, or a higher iron recovery at an equal silica content. The primary lauryl amine acetate is a stronger collector but not as selective as the ether amine acetate. In addition, the primary lauryl amine must be completely neutralized to make it readily dispersible in water, and even then it is a solid rather than a liquid salt and cannot be handled as easily.
Various modifications and alterations of this invention will become apparent to those skilled in the art without departing from the scope and spirit of this invention.
We claim:
1. A froth flotation process for separating silica from an ore, which comprises frothing said ore in the presence of an aqueous medium containing a water dispersible acid salt of an aliphatic ether diamine having the general formula where R is an aliphatic radical having 1-13 carbon atoms, and R" is a hydrogen atom or a methyl group and floating off the silica from said ore.
2. The process according to claim 1, wherein said other diamine is used in the form of its acetate salt.
3. The process according to claim 1, wherein said ether diamine has the general formula where R is an alkyl radical having 7 to 13 carbon atoms and 14 methyl branches, and R" is a hydrogen atom or a methyl group.
4-. A froth flotation process for separating silica from iron ore, which comprises frothing said ore in an aqueous medium in the presence of 0.1 to 2 pounds per ton of said ore of a Water-dispersible, liquid aliphatic ether diamine salt having the general formula where R is an aliphatic radical having 7'-l3 carbon atoms, R" is hydrogen or methyl, and A is a solubilizing saltforming anion of monobasic acid and floating oil the silica from said ore.
5. The process according to claim 4, wherein said iron ore is magnetite.
6. The process according to claim 5, wherein said anion is acetate.
7. The process according to claim 6, wherein said ether diamine salt is N-tridecoxypropyl-l,3-propylene diamine monoacetate.
8. In a froth flotation process for separating silica from an ore by subjecting said ore to froth flotation in the presence of a collecting agent to float off said silica, the improvement comprising using as the collecting agent an acid salt of an ether diamine having the general formula R-O-CH CH R) CH NHCH CI-I R CH -NH where R is an aliphatic radical having 1-l3 carbon atoms and R" is a hydrogen atom or a methyl group.
References Cited UNITED STATES PATENTS 2,166,150 7/1939 Howk 209166 X 2,177,985 10/1939 Harris 209-166 2,214,352 9/1940 Schoeller 209-466 X 2,222,728 11/1940 Tartaron 209-166 2,307,397 1/1943 Falloner 209-166 2,372,624 3/1945 Carpenter 260584 2,450,720 10/1948 De Vaney 209-166 2,839,131 6/1958 Monson 209-166 3,076,819 2/1963 Heise 260-584 X 3,251,852 5/1966 De Groote 260-584 HARRY B. THORNTON, Primary Examiner.
R. HALPER, Assistant Examiner.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US600054A US3363758A (en) | 1966-12-08 | 1966-12-08 | Use of primary aliphatic ether amine acid salts in froth flotation process |
DE19671558950 DE1558950A1 (en) | 1966-12-08 | 1967-11-29 | Use of salts of primary aliphatic aetheramines in foam preparation processes |
FR1553908D FR1553908A (en) | 1966-12-08 | 1967-11-30 | |
SE16910/67A SE326416B (en) | 1966-12-08 | 1967-12-08 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US600054A US3363758A (en) | 1966-12-08 | 1966-12-08 | Use of primary aliphatic ether amine acid salts in froth flotation process |
Publications (1)
Publication Number | Publication Date |
---|---|
US3363758A true US3363758A (en) | 1968-01-16 |
Family
ID=24402173
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US600054A Expired - Lifetime US3363758A (en) | 1966-12-08 | 1966-12-08 | Use of primary aliphatic ether amine acid salts in froth flotation process |
Country Status (4)
Country | Link |
---|---|
US (1) | US3363758A (en) |
DE (1) | DE1558950A1 (en) |
FR (1) | FR1553908A (en) |
SE (1) | SE326416B (en) |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
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US3932274A (en) * | 1971-08-27 | 1976-01-13 | Director-General Of The Agency Of Industrial Science And Technology | Method for eliminating metals from a solution containing a very slight amount of the metals |
US4168227A (en) * | 1976-10-18 | 1979-09-18 | Ceca S.A. | Flotation method for oxidized ores |
FR2430981A1 (en) * | 1978-07-12 | 1980-02-08 | Bahr Albert | PROCESS FOR TREATING SALINE SLAG OF ALUMINUM FUSION |
US4278533A (en) * | 1980-02-07 | 1981-07-14 | The Dow Chemical Company | Conditioner for flotation of oxidized coal |
US4287052A (en) * | 1980-04-07 | 1981-09-01 | The Dow Chemical Company | Alkyl-substituted phenyl ether amine collectors in flotation |
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US5540336A (en) * | 1991-10-04 | 1996-07-30 | Henkel Kommanditgesellschaft Auf Aktien | Method of producing iron ore concentrates by froth flotation |
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US20090114573A1 (en) * | 2006-03-09 | 2009-05-07 | Klaus-Ulrich Pedain | Flotation Reagent For Silicates |
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US20120325725A1 (en) * | 2010-01-19 | 2012-12-27 | Clariant Finance (Bvi) Limited | Flotation Reagent For Iron Ores Containing Magnetite And/Or Haematite |
US8701892B2 (en) * | 2010-12-28 | 2014-04-22 | Akzo Nobel Chemicals International B.V. | Amine-containing formulations for reverse froth flotation of silicates from iron ore |
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Publication number | Priority date | Publication date | Assignee | Title |
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SE8105336L (en) * | 1980-09-09 | 1982-03-10 | Exxon Research Engineering Co | FLOTING PROCEDURE FOR THE TREATMENT OF ORE AND THE PROCEDURE USING THE COLLECTION REAGENT |
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US3932274A (en) * | 1971-08-27 | 1976-01-13 | Director-General Of The Agency Of Industrial Science And Technology | Method for eliminating metals from a solution containing a very slight amount of the metals |
US4168227A (en) * | 1976-10-18 | 1979-09-18 | Ceca S.A. | Flotation method for oxidized ores |
FR2430981A1 (en) * | 1978-07-12 | 1980-02-08 | Bahr Albert | PROCESS FOR TREATING SALINE SLAG OF ALUMINUM FUSION |
US4275847A (en) * | 1978-07-12 | 1981-06-30 | Albert Bahr | Process for the treatment of aluminum-salt slags |
US4278533A (en) * | 1980-02-07 | 1981-07-14 | The Dow Chemical Company | Conditioner for flotation of oxidized coal |
US4287052A (en) * | 1980-04-07 | 1981-09-01 | The Dow Chemical Company | Alkyl-substituted phenyl ether amine collectors in flotation |
US4319987A (en) * | 1980-09-09 | 1982-03-16 | Exxon Research & Engineering Co. | Branched alkyl ether amines as iron ore flotation aids |
US4422928A (en) * | 1981-03-09 | 1983-12-27 | Exxon Research & Engineering Co. | Silica flotation collectors derived from isononyl alcohol |
US4472270A (en) * | 1983-05-18 | 1984-09-18 | Mobil Oil Corporation | Beneficiation of ores |
US5182039A (en) * | 1991-03-29 | 1993-01-26 | Exxon Chemical Patents, Inc. | Synergistic fluorinated ore flotation aids |
US5540336A (en) * | 1991-10-04 | 1996-07-30 | Henkel Kommanditgesellschaft Auf Aktien | Method of producing iron ore concentrates by froth flotation |
US5261539A (en) * | 1992-10-07 | 1993-11-16 | American Cyanamid Company | Flotation process for purifying calcite |
US5540337A (en) * | 1994-04-04 | 1996-07-30 | Baker Hughes Incorporated | Alkyloxyalkaneamines useful as cationic froth flotation collectors |
US6076682A (en) * | 1997-11-27 | 2000-06-20 | Akzo Nobel N.V. | Process for froth flotation of silicate-containing iron ore |
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Also Published As
Publication number | Publication date |
---|---|
FR1553908A (en) | 1969-01-17 |
DE1558950A1 (en) | 1970-04-23 |
SE326416B (en) | 1970-07-27 |
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