CN1447790A - 脂族异羟肟酸盐的制备 - Google Patents
脂族异羟肟酸盐的制备 Download PDFInfo
- Publication number
- CN1447790A CN1447790A CN01814494.2A CN01814494A CN1447790A CN 1447790 A CN1447790 A CN 1447790A CN 01814494 A CN01814494 A CN 01814494A CN 1447790 A CN1447790 A CN 1447790A
- Authority
- CN
- China
- Prior art keywords
- acid
- fatty acid
- azanol
- salt
- reaction
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims abstract description 52
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims abstract description 43
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000000194 fatty acid Substances 0.000 claims abstract description 29
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 28
- 229930195729 fatty acid Natural products 0.000 claims abstract description 28
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims description 68
- 125000001931 aliphatic group Chemical group 0.000 claims description 36
- -1 alkane alcohol ester Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000013530 defoamer Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000006260 foam Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 6
- 229910052728 basic metal Inorganic materials 0.000 claims description 6
- 150000003818 basic metals Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 150000002632 lipids Chemical class 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000004157 Nitrosyl chloride Substances 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019392 nitrosyl chloride Nutrition 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 19
- 238000005188 flotation Methods 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 12
- 239000010949 copper Substances 0.000 description 11
- 150000004702 methyl esters Chemical class 0.000 description 11
- 239000001103 potassium chloride Substances 0.000 description 11
- 235000011164 potassium chloride Nutrition 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000003240 coconut oil Substances 0.000 description 7
- 235000019864 coconut oil Nutrition 0.000 description 7
- 125000005908 glyceryl ester group Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000003346 palm kernel oil Substances 0.000 description 6
- 235000019865 palm kernel oil Nutrition 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007667 floating Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052592 oxide mineral Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241001085205 Prenanthella exigua Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- DVRDHUBQLOKMHZ-UHFFFAOYSA-N chalcopyrite Chemical group [S-2].[S-2].[Fe+2].[Cu+2] DVRDHUBQLOKMHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052951 chalcopyrite Inorganic materials 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- VRXOQUOGDYKXFA-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.ON.OS(O)(=O)=O VRXOQUOGDYKXFA-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229940023462 paste product Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052569 sulfide mineral Inorganic materials 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
样品物料 | 在波数(vcm-1)处的IR信号 |
应用甲醇溶剂法由椰子油甲酯制得的AM2固体 | 1627和1554(酰胺羰基) 3213.5(-OH) |
应用本方法制得的AM2的钾盐 | 1627.4和1554(羰基) 3213.2(-OH) |
应用本方法制得的AM2的钠盐 | 1633和1574(羰基) 3244(-OH) |
原料和金属含量 | 浮选浓缩物含量 |
发生Cu矿 Cu0.6% | Cu12% |
氧化铜矿 Cu0.8%Au0.9ppm | Cu38%Au12ppm |
氧化锌矿 Zn2.5% | Zn15.5% |
SnO2尾渣 Sn0.6% | Sn9.5% |
Claims (21)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPQ9068A AUPQ906800A0 (en) | 2000-07-28 | 2000-07-28 | Preparation of fatty hydroxamate |
AUPQ9068 | 2000-07-28 | ||
AUPR0551 | 2000-10-03 | ||
AUPR0551A AUPR055100A0 (en) | 2000-10-03 | 2000-10-03 | Preparation of fatty hydroxamate |
PCT/AU2001/000920 WO2002010122A1 (en) | 2000-07-28 | 2001-07-27 | Preparation of fatty hydroxamate |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1447790A true CN1447790A (zh) | 2003-10-08 |
CN100349860C CN100349860C (zh) | 2007-11-21 |
Family
ID=25646390
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB018144942A Expired - Lifetime CN100349860C (zh) | 2000-07-28 | 2001-07-27 | 脂族异羟肟酸盐的制备 |
Country Status (13)
Country | Link |
---|---|
US (1) | US7049452B2 (zh) |
EP (1) | EP1309543B1 (zh) |
CN (1) | CN100349860C (zh) |
AT (1) | ATE418537T1 (zh) |
AU (2) | AU2001276170C1 (zh) |
CA (1) | CA2417399C (zh) |
DE (1) | DE60137134D1 (zh) |
DK (1) | DK1309543T3 (zh) |
ES (1) | ES2319733T3 (zh) |
MX (1) | MXPA03000819A (zh) |
MY (1) | MY154994A (zh) |
PT (1) | PT1309543E (zh) |
WO (1) | WO2002010122A1 (zh) |
Cited By (5)
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CN101816980A (zh) * | 2010-04-30 | 2010-09-01 | 广州有色金属研究院 | 一种脂肪羟肟酸捕收剂的制备方法和用途 |
CN104592056A (zh) * | 2015-01-19 | 2015-05-06 | 烟台腾辉化工有限公司 | 一种n-羟基正辛酰胺的制备工艺 |
CN114058881A (zh) * | 2021-10-29 | 2022-02-18 | 深圳市中金岭南有色金属股份有限公司丹霞冶炼厂 | 一种羟肟酸镓锗萃取剂的再生方法 |
CN114105824A (zh) * | 2021-12-09 | 2022-03-01 | 江苏艾科维科技有限公司 | 一种异羟肟酸的合成方法 |
CN114746397A (zh) * | 2019-11-20 | 2022-07-12 | Upl有限公司 | 用于合成异羟肟酸的连续流方法 |
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WO2003011470A1 (en) * | 2001-07-27 | 2003-02-13 | Ausmelt Limited | Hydroxamate composition and method for froth flotation |
ITFI20060006A1 (it) * | 2006-01-04 | 2007-07-05 | Colorobbia Italiana Spa | Nanoparticelle funzionalizzate, loro produzione ed uso |
CN101549327B (zh) * | 2009-05-05 | 2013-06-19 | 武汉工程大学 | 复合浮选剂的制备方法 |
PE20211337A1 (es) | 2014-01-31 | 2021-07-26 | Goldcorp Inc | Proceso para la separacion y recuperacion de sulfuros de metales de una mena o concentrado de sulfuros mixtos |
MA42580B1 (fr) | 2015-11-25 | 2020-10-28 | Cytec Ind Inc | Compositions de collecteurs et leurs procédés d'utilisation dans des procédés de flottation de minerais |
WO2023022899A1 (en) * | 2021-08-20 | 2023-02-23 | Inolex Investment Corporation | Potassium hydrogen salts of alkylhydroxamates and compositions comprising the same |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US3936494A (en) * | 1974-09-25 | 1976-02-03 | Diamond Shamrock Corporation | Naphthenohydroxamic acid preparation |
US4871466A (en) * | 1987-10-15 | 1989-10-03 | American Cyanamid Company | Novel collectors and processes for making and using same |
DE69517548T2 (de) * | 1994-04-22 | 2001-01-18 | Mitsui Chemicals Inc | Verfahren zur Herstellung von substituierten Aminen und Verfahren zur Reinigung von ihren Zwischenprodukten |
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2001
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- 2001-07-27 CN CNB018144942A patent/CN100349860C/zh not_active Expired - Lifetime
- 2001-07-27 EP EP01953679A patent/EP1309543B1/en not_active Expired - Lifetime
- 2001-07-27 AU AU2001276170A patent/AU2001276170C1/en not_active Expired
- 2001-07-27 WO PCT/AU2001/000920 patent/WO2002010122A1/en active IP Right Grant
- 2001-07-27 DK DK01953679T patent/DK1309543T3/da active
- 2001-07-27 AU AU7617001A patent/AU7617001A/xx active Pending
- 2001-07-27 PT PT01953679T patent/PT1309543E/pt unknown
- 2001-07-27 MY MYPI20053432A patent/MY154994A/en unknown
- 2001-07-27 CA CA2417399A patent/CA2417399C/en not_active Expired - Fee Related
- 2001-07-27 ES ES01953679T patent/ES2319733T3/es not_active Expired - Lifetime
- 2001-07-27 DE DE60137134T patent/DE60137134D1/de not_active Expired - Lifetime
- 2001-07-27 AT AT01953679T patent/ATE418537T1/de active
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101816980A (zh) * | 2010-04-30 | 2010-09-01 | 广州有色金属研究院 | 一种脂肪羟肟酸捕收剂的制备方法和用途 |
CN101816980B (zh) * | 2010-04-30 | 2012-08-22 | 广州有色金属研究院 | 一种脂肪羟肟酸捕收剂的制备方法和用途 |
CN104592056A (zh) * | 2015-01-19 | 2015-05-06 | 烟台腾辉化工有限公司 | 一种n-羟基正辛酰胺的制备工艺 |
CN114746397A (zh) * | 2019-11-20 | 2022-07-12 | Upl有限公司 | 用于合成异羟肟酸的连续流方法 |
CN114058881A (zh) * | 2021-10-29 | 2022-02-18 | 深圳市中金岭南有色金属股份有限公司丹霞冶炼厂 | 一种羟肟酸镓锗萃取剂的再生方法 |
CN114105824A (zh) * | 2021-12-09 | 2022-03-01 | 江苏艾科维科技有限公司 | 一种异羟肟酸的合成方法 |
Also Published As
Publication number | Publication date |
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ES2319733T3 (es) | 2009-05-12 |
US7049452B2 (en) | 2006-05-23 |
AU2001276170B2 (en) | 2005-10-13 |
PT1309543E (pt) | 2009-02-03 |
DK1309543T3 (da) | 2009-04-06 |
EP1309543A4 (en) | 2005-11-16 |
US20040059156A1 (en) | 2004-03-25 |
AU2001276170C1 (en) | 2006-10-26 |
WO2002010122A1 (en) | 2002-02-07 |
DE60137134D1 (de) | 2009-02-05 |
EP1309543A1 (en) | 2003-05-14 |
CA2417399C (en) | 2010-06-15 |
MXPA03000819A (es) | 2004-11-01 |
MY154994A (en) | 2015-08-28 |
ATE418537T1 (de) | 2009-01-15 |
EP1309543B1 (en) | 2008-12-24 |
AU7617001A (en) | 2002-02-13 |
CA2417399A1 (en) | 2002-02-07 |
CN100349860C (zh) | 2007-11-21 |
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