CN102503874A - Thiourea compound, application thereof to metal ore flotation and preparation of thiourea compound - Google Patents
Thiourea compound, application thereof to metal ore flotation and preparation of thiourea compound Download PDFInfo
- Publication number
- CN102503874A CN102503874A CN2011103416797A CN201110341679A CN102503874A CN 102503874 A CN102503874 A CN 102503874A CN 2011103416797 A CN2011103416797 A CN 2011103416797A CN 201110341679 A CN201110341679 A CN 201110341679A CN 102503874 A CN102503874 A CN 102503874A
- Authority
- CN
- China
- Prior art keywords
- oxygen
- hydrocarbon
- ore
- flotation
- aryl
- 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
Abstract
The invention discloses a thiourea compound, an application thereof to metal ore flotation and preparation of the thiourea compound. An N-carboalkoxy(aryloxy)-N'-carboalkoxypropyl thiourea compound shown in a formula (I) is taken as a collecting agent of non-ferrous metal ore and precious metal flotation. The formula (I) is shown in the specifications, wherein R1 represents alkyl, aryl or aralkyl with 1-8 carbon atoms, and R2 represents alkyl, aryl or aralkyl with 1-16 carbon atoms; or the formula (I) is R3OR4, wherein R3 represents alkyl with 1-3 carbon atoms, and R4 represents alkylene, aryl or aromatic alkylidene with 1-16 carbon atoms; and R1 and R2 are independent of each other. The compound shown as the formula (I) is taken as a flotation collecting agent, so that valent metal minerals are recovered efficiently from non-ferrous metal ore and precious metal ore. In the N-carboalkoxy(aryloxy)-N'-carboalkoxypropyl thiourea compound, ether is contained in a collecting agent molecule, so that the melting point of the collecting agent can be lowered, the dispersibility of the collecting in an aqueous solution is enhanced, and flotation separation extraction of the non-ferrous metal ore and noble metal ore is enhanced. The N-carboalkoxy(aryloxy)-N'-carboalkoxypropyl thiourea compound has the characteristics of easy and simple synthesizing method, high metal recovering rate, and the like.
Description
[technical field]
The present invention relates to a kind of compound of new texture---N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound and preparation method thereof and the application in the metallic ore flotation.
[background technology]
Flotation reagent is the gordian technique of flotation process separation and Extraction valuable mineral component.More and more poorer along with Mineral resources, thin, assorted, research and develop new and effective flotation collector, for the development and use of complicacy ore hard to manage, improve the metal comprehensive recovery and have vital role.
Thiourea has become the mineral floating collecting agent of a quasi-representative because metals ions such as copper, lead, zinc, gold are had good sequestering action.The thiourea compound of reporting for work at present as flotation collector has thiambutosine (to be commonly called as baiyao; See structural formula a, D.W.Fuerstenau, R.Herrera-Urbina; D.W.McGlashan.Studies on the applicability of chelating agents as universal collectors for copper minerals.Int.J.Miner.Process.2000; 58:15-33), isothiourea (Wang Dian assistant, woods is strong, Jiang Yuren. ore dressing designs with metallurgical agent molecule. Changsha: press of Zhongnan Polytechnic Univ; 1996), N-hydrocarbon carbonyl oxygen thiocarbamide (is seen structural formula b; Fu Yun-Lung, Wang Samuel S.Neutral hydrocarboxycarbonyl thiourea sulfide collectors.USRE32786,1988-11-22; Liu Guang-yi; Zhong Hong, Xia Liu-yin, Wang Shuai; Xu Zheng-he.Improving copper flotation recovery from a refractory copper porphyry ore by using ethoxycarbonyl thiourea as a collector.Minerals Engineering.2011; 24:817-824), bis-thiourea (is seen structural formula c, d, e and f, Zhong Hong, Liu Guangyi; Wang Shuai. dibasic acid esters base diisothiocyanic acid ester derivative application in sulfide flotation and preparation method thereof .CN101337206A, 2009-1-7; Liu Guangyi, clock is grand. sulfide flotation collector and use method of diacyl bis-thiourea and preparation method .CN101337206A, 2009-01-07; Zhong Hong, Liu Guangyi, Yuan Lu, Wang Shuai, the summer shade of willow trees. a kind of flotation collector and preparation method thereof .CN101698161A, 2009-10-26).
These thiocarbamide collecting agents show good collecting performance to non-ferrous metal mineral and precious metal minerals, can realize that these valuable elements separate with the selective flotation of gangue minerals such as pyrite, pyrrhotite in the pH scope widely.Yet existing thiocarbamide collecting agent generally is solid at normal temperatures, adds inconvenience, and dispersion is bad in ore pulp simultaneously, and is insufficient with the mineral surface effect, limits their application in flotation.
[summary of the invention]
The present invention proposes a kind of thiourea compound of new texture---N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound and application are as flotation collector, and the preparation method of this compounds.Through the addition reaction of N-hydrocarbon carbonyl oxygen lsothiocyanates and hydrocarbon oxygen propylamine compound, the highly economical that has formed N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound is synthetic.N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound can reduce the fusing point and its dispersiveness in the aqueous solution of enhancing of collecting agent, thereby the flotation separation of strengthening nonferrous metallic ores and precious metal ore is extracted owing to contain ether in the collecting agent molecule.Have characteristics such as simple synthetic method, metal recovery rate height.
At present, N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound does not appear in the newspapers as flotation reagent in pneumatic flotation, in U.S. CA DB, does not see the defined N-hydrocarbon carbonyl oxygen-N ' of the present invention-hydrocarbon oxygen propyl group thiocarbamide and compound method and application yet.
The flotation collector that the purpose of this invention is to provide a kind of new texture---N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound; And as the application of the collecting agent of nonferrous metallic ores and precious metal ore flotation, with reinforcement to the comprehensive recovery of copper, lead, zinc, nickel, gold and silver etc. and realize these mineral and the efficient flotation separation of pyrite, pyrrhotite etc.
Another object of the present invention aims to provide the high efficiency preparation method of described N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound.
The objective of the invention is to realize through following manner:
A kind of name is called N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound and has the structure shown in the formula I:
R wherein
1Represent C
1-C
8Alkyl, C
6-C
8Aryl or C
7-C
8Aralkyl, R
2Represent C
1-C
16Alkyl, aryl or aralkyl, or R
3OR
4, R wherein
3Represent C
1-C
3Alkyl, R
4Represent C
1-C
16Alkylidene group, C
6-C
16Aryl or C
7-C
16Arylmethylene alkyl; R
1, R
2Separate.
R wherein
1Be preferably methyl, ethyl, sec.-propyl, butyl or isobutyl-; R
2Be preferably propyl group, sec.-propyl, butyl, isobutyl-or methoxyethyl.
Application of the present invention is the collecting agent of the N-hydrocarbon carbonyl oxygen-N ' shown in the formula I-hydrocarbon oxygen propylthio carbamide compound as nonferrous metals ore or precious metal ore flotation.
Operation primary process is: (a) go into flotation behind the grinde ore; (b) in ore grinding and/or floatation process, add flotation reagent and size mixing, contain a kind of N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound in the medicament of interpolation at least; (c) through froth-flotation method emersion useful metal mineral.
N-hydrocarbon carbonyl oxygen-N ' according to the invention-hydrocarbon oxygen propylthio carbamide compound is as flotation collector; Precious metal minerals such as copper minerals such as non-ferrous metal mineral and precious metal minerals such as yellow copper ore, cupric ion activatory zinc mineral, nickel mineral, gold and silver had strong collecting ability; A little less than the collecting ability to gangue minerals such as pyrite, pyrrhotite, selectivity is good.Adopt N-hydrocarbon carbonyl oxygen-N ' of the present invention-hydrocarbon oxygen propylthio carbamide compound perhaps to unite use as flotation collector separately with other collecting agent; Under the condition of N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound consumption 1～100 gram/ton, pH values of pulp 5.0～14 scopes; Compare with existing collecting agent; The flotation recovery rate of nonferrous metals ore thing and precious metal minerals is improved; Realize the efficient flotation separation of valuable mineral and gangue mineral, reduce suppressor factor consumption when separating, improve the metal comprehensive recovery.
Flotation collector N-hydrocarbon carbonyl oxygen-N ' of the present invention-hydrocarbon oxygen propylthio carbamide compound can make through following method.
N-hydrocarbon carbonyl oxygen lsothiocyanates and hydrocarbon oxygen propylamine compound are carried out addition reaction, temperature of reaction-15 ℃～60 ℃, the reaction times is 1～6 hour, generates suc as formula the hydrocarbon carbonyl oxygen-N ' of N-shown in the I-hydrocarbon oxygen propylthio carbamide compound;
The general molecular formula of described N-hydrocarbon carbonyl oxygen lsothiocyanates is:
R wherein
1Represent C
1-C
8Alkyl.Comprise N-methoxycarbonyl lsothiocyanates, N-ethoxycarbonyl isothiocyanate, the N-third oxygen carbony isorhodanate, N-butoxy carbonyl lsothiocyanates, N-penta oxygen carbony isorhodanate, the own oxygen carbony isorhodanate of N-, the different hot oxygen carbony isorhodanate of N-and N-carbobenzoxy-(Cbz) lsothiocyanates etc.
The chemical general formula of described hydrocarbon oxygen propylamine compound is R
2OCH
2CH
2CH
2NH
2, R wherein
2Represent C
1-C
16Alkyl, C
6-C
16Aryl or C
7-C
16Aralkyl, or R
3OR
4, R wherein
3Represent C
1-C
3Alkyl, R
4Represent C
1-C
16Alkylidene group, C
6-C
16Aryl or C
7-C
16Arylmethylene alkyl.Comprise ethoxy propylamine, the third oxygen propylamine, the different third oxygen propylamine, fourth oxygen propylamine, isobutyl oxygen propylamine, hot oxygen propylamine, phenoxy propylamine, dodecyl oxygen propylamine, first ethoxy propylamine etc.
The preparation method of N-hydrocarbon carbonyl oxygen-N ' according to the invention-hydrocarbon oxygen propyl group thiocarbamide has following characteristics: the preparation process is simple, efficient, practical, and conversion rate of products is greater than 92%, and crude product promptly can be used as flotation collector.
[embodiment]
The present invention is further specified by the following example, but does not receive the restriction of these embodiment.All umbers and percentage ratio all refer to quality except as otherwise herein provided among the embodiment.
(1) preparation of N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound
The preparation of embodiment 1 N-ethoxycarbonyl-N '-Ding oxygen propyl group thiocarbamide
131.2 parts of γ-butoxy propyl amines are added water, and to be configured to mass concentration be γ-butoxy propyl amine aqueous solution of 30%; Temperature of reaction be-5～10 ℃ with agitation condition under; Slowly join in the three-necked flask that contains 131.2 parts of N-ethoxycarbonyl isothiocyanates; Stirring reaction 2 hours is warmed up to room temperature then and reacted 1 hour again.Static layering, 262.5 parts of yellow oil product N-ethoxycarbonyl-N '-Ding oxygen propyl group thiocarbamide, product purity is 94.5%.
The preparation of embodiment 2 N-ethoxycarbonyl-N '-different third oxygen propyl group thiocarbamide
117.2 parts of γ-isopropoxy propylamine is added water, and to be configured to mass concentration be γ-isopropoxy propylamine aqueous solution of 20%; Temperature of reaction be-5～10 ℃ with agitation condition under; Slowly join in the three-necked flask that contains 131.2 parts of N-ethoxycarbonyl isothiocyanates; Stirring reaction 1 hour is warmed up to room temperature then and reacted 1 hour again.Static layering, 248.2 parts of yellow oil product N-ethoxycarbonyl-N '-different third oxygen propyl group thiocarbamide, product purity is 95.5%.
The preparation of the different hot oxygen carbonyl-N ' of embodiment 3 N--different third oxygen propyl group thiocarbamide
117.2 parts of γ-isopropoxy propylamine is added water, and to be configured to mass concentration be γ-isopropoxy propylamine aqueous solution of 40%; Temperature of reaction be-5～10 ℃ with agitation condition under; Slowly join in the three-necked flask that contains 215.2 parts of different hot oxygen carbony isorhodanates of N-; Stirring reaction 1.5 hours is warmed up to room temperature then and reacted 1 hour again.Static layering, 332.1 parts of different hot oxygen carbonyl-N ' of the yellow oil product N--different third oxygen propyl group thiocarbamide, product purity is 95.8%.
(2) N-hydrocarbon carbonyl oxygen-N '-application of hydrocarbon oxygen propylthio carbamide compound in the metallic ore flotation
Embodiment 4: certain copper mine stone ore appearance, copper mineral is mainly yellow copper ore in the ore, is copper glance-alpha chalcocite, tetrahedrite-tennantite etc. secondly.Iron mineral is mainly pyrite.Raw ore cupric 0.37%, sulfur-bearing 1.42%.
Experiment process: one roughing; Grinding fineness :-0.074mm accounts for 64.6%; The medicament condition: lime consumption 1000 gram/tons, slurry pH are 8.5, and all the other medicament conditions and result thereof see table 1.The test-results of table 1 shows that N-hydrocarbon carbonyl oxygen-N ' of the present invention-hydrocarbon oxygen propyl group thiocarbamide collecting agent can be obtained than collecting agent butyl xanthate commonly used and the higher copper flotation recovery rate of N-ethoxycarbonyl-N '-propyl group thiocarbamide.
The flotation conditions and the result thereof of table 1 N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound
Embodiment 5 certain porphyry copper stone ore appearance, copper mineral is mainly yellow copper ore in the ore, and sulfur mineral is mainly pyrite.Raw ore cupric 0.41%, sulfur-bearing 2.02%.
Experiment process: one roughing; Grinding fineness :-0.074mm accounts for 64.3%; The medicament condition: lime consumption 1200 gram/tons, slurry pH are 8.5, and all the other medicament conditions and result thereof see table 2.The test-results of table 2 shows that N-hydrocarbon carbonyl oxygen-N ' of the present invention-hydrocarbon oxygen propyl group thiocarbamide collecting agent is obtained than collecting agent butyl xanthate commonly used and the higher copper flotation recovery rate of N-ethoxycarbonyl-N '-propyl group thiocarbamide.
The flotation porphyry copper of table 2 N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound
Embodiment 6 certain copper-lead zinc ore, raw ore cupric about 0.58%.Experiment process: one roughing.Grinding fineness :-0.074mm80%.The medicament condition: yellow soda ash 1500 gram/tons, zinc sulfate 1000 gram/tons, S-WAT 1000 gram/tons, slurry pH is 8.0, all the other medicament conditions and result thereof see table 3.The test-results of table 3 shows that N-ethoxycarbonyl-N ' of the present invention-Ding oxygen propyl group thiocarbamide is obtained the copper flotation recovery rate higher than N-butoxy carbonyl-N '-propyl group thiocarbamide.
Table 3 new collector flotation copper-lead zinc ore test-results
Embodiment 7 certain copper tin ore, raw ore contains Cu 0.41%, Sn 0.39%, S 8.6%, Fe 25.1%, and wherein the copper oxidation ratio is 6.3%, secondary rate is 14.1%.Experiment process: one roughing once purging selection.Grinding fineness :-0.074mm65%; The medicament condition: ball milling lime 3000 gram/tons, slurry pH are 8.5, and 730A is a pore forming material, and all the other medicament conditions and result thereof see table 4.The test-results of table 4 shows that N-hydrocarbon carbonyl oxygen-N ' of the present invention-hydrocarbon oxygen propyl group thiocarbamide collecting agent also can be obtained than collecting agent butyl xanthate commonly used and the higher copper flotation recovery rate of N-ethoxycarbonyl-N '-propyl group thiocarbamide.
Table 4 new collector Floatation of Copper tin ore test-results
Claims (5)
1. a thiourea compound is characterized in that, described thiourea compound is N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propyl group thiocarbamide, has structure shown in the formula I; Collecting agent for nonferrous metallic ores or precious metal ore flotation;
R wherein
1Represent C
1-C
8Alkyl, C
6-C
8Aryl or C
7-C
8Aralkyl; R
2Represent C
1-C
16Alkyl, C
6-C
16Aryl or C
7-C
16Aralkyl, or R
3OR
4, R wherein
3Represent C
1-C
3Alkyl, R
4Represent C
1-C
16Alkylidene group, C
6-C
16Aryl or C
7-C
16Arylmethylene alkyl; R
1, R
2Separate.
2. thiourea compound according to claim 1 is characterized in that, wherein R
1Be methyl, ethyl, sec.-propyl, butyl or isobutyl-; R
2Be propyl group, sec.-propyl, butyl, isobutyl-or methoxyethyl.
3. the preparation method of the described N-hydrocarbon carbonyl oxygen-N ' of claim 1-hydrocarbon oxygen propylthio carbamide compound; It is characterized in that; N-hydrocarbon carbonyl oxygen lsothiocyanates and hydrocarbon oxygen propylamine compound are carried out addition reaction; Temperature of reaction-15 ℃～60 ℃, the reaction times is 1～6 hour, generates N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound with structure shown in the formula I;
Described N-hydrocarbon carbonyl oxygen lsothiocyanates have a structure shown in the formula II:
R wherein
1Represent C
1-C
8Alkyl, C
6-C
8Aryl or C
7-C
8Aralkyl;
The chemical general formula of described hydrocarbon oxygen propylamine compound is R
2OCH
2CH
2CH
2NH
2, R wherein
2Represent C
1-C
16Alkyl, C
6-C
16Aryl or C
7-C
16Aralkyl, or R
3OR
4, R wherein
3Represent C
1-C
3Alkyl, R
4Represent C
1-C
16Alkylidene group, C
6-C
16Aryl and C
7-C
16Arylmethylene alkyl.
4. the application of claim 1 or 2 described thiourea compounds is with N-hydrocarbon carbonyl oxygen-N '-hydrocarbon oxygen propylthio carbamide compound of structure shown in the formula I collecting agent as nonferrous metallic ores or precious metal ore flotation.
5. the application of thiourea compound according to claim 4, its nonferrous metallic ores or precious metal ore be copper-containing ore, zinc-containing ores, contain lead ore, nickel-containing ore, contain molybdenum ore, golden precious metal ore or silver-colored precious metal ore.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110341679 CN102503874B (en) | 2011-11-02 | 2011-11-02 | Thiourea compound, application thereof to metal ore flotation and preparation of thiourea compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110341679 CN102503874B (en) | 2011-11-02 | 2011-11-02 | Thiourea compound, application thereof to metal ore flotation and preparation of thiourea compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102503874A true CN102503874A (en) | 2012-06-20 |
| CN102503874B CN102503874B (en) | 2013-10-23 |
Family
ID=46216025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201110341679 Active CN102503874B (en) | 2011-11-02 | 2011-11-02 | Thiourea compound, application thereof to metal ore flotation and preparation of thiourea compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102503874B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103071599A (en) * | 2012-12-25 | 2013-05-01 | 中南大学 | Double-ligand thiourea collecting agent and preparation thereof and application thereof in metal ore floatation |
| CN104084313A (en) * | 2014-06-24 | 2014-10-08 | 云南科力新材料有限公司 | Flotation collecting foaming agent and preparation method thereof |
| CN107377232A (en) * | 2017-07-12 | 2017-11-24 | 湖南有色金属研究院 | A kind of composite restrainer being used in lead concentrate floatation process |
| CN110681495A (en) * | 2019-09-28 | 2020-01-14 | 北京矿冶科技集团有限公司 | Thiourea compound flotation separation inhibitor and flotation separation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080185317A1 (en) * | 2007-02-07 | 2008-08-07 | Nagaraj Devarayasamudram R | Novel dithiocarbamate collectors and their use in the beneficiation of mineral ore bodies |
| CN101337205A (en) * | 2008-08-13 | 2009-01-07 | 中南大学 | Use of diester isosulfocyanate in sulphide ore floation and preparation method thereof |
-
2011
- 2011-11-02 CN CN 201110341679 patent/CN102503874B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080185317A1 (en) * | 2007-02-07 | 2008-08-07 | Nagaraj Devarayasamudram R | Novel dithiocarbamate collectors and their use in the beneficiation of mineral ore bodies |
| CN101337205A (en) * | 2008-08-13 | 2009-01-07 | 中南大学 | Use of diester isosulfocyanate in sulphide ore floation and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| G. FAIRTHORNE等: "]interaction of thionocarbamate and thiourea collectors with sulphide minerals: a flotation and adsorption study", 《INT. J. MINER. PROCESS》 * |
| LIU GUANG-YI等: "Effect of N-substituents on performance of thiourea collectors by density functional theory calculations", 《TRANS. NONFERROUS MET. SOC.》 * |
| 刘广义等: "中碱度条件下乙氧羰基硫脲浮选分离铜硫", 《中国有色金属学报》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103071599A (en) * | 2012-12-25 | 2013-05-01 | 中南大学 | Double-ligand thiourea collecting agent and preparation thereof and application thereof in metal ore floatation |
| CN104084313A (en) * | 2014-06-24 | 2014-10-08 | 云南科力新材料有限公司 | Flotation collecting foaming agent and preparation method thereof |
| CN107377232A (en) * | 2017-07-12 | 2017-11-24 | 湖南有色金属研究院 | A kind of composite restrainer being used in lead concentrate floatation process |
| CN110681495A (en) * | 2019-09-28 | 2020-01-14 | 北京矿冶科技集团有限公司 | Thiourea compound flotation separation inhibitor and flotation separation method thereof |
| CN110681495B (en) * | 2019-09-28 | 2021-08-06 | 北京矿冶科技集团有限公司 | Thiourea compound flotation separation inhibitor and flotation separation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102503874B (en) | 2013-10-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101757985B (en) | Mineral flotation collectors | |
| CN104874488B (en) | Collecting agent and preparation method and application thereof | |
| CN103620064B (en) | The method of gold recovering and copper from mixing oxysulfide Copper Ores | |
| CN101698160B (en) | Sulfide flotation collector and preparation method | |
| CN101337206B (en) | Sulphide ore floation collector and use method of diacyl bis-thiourea and preparation method thereof | |
| CN102516144B (en) | Thiourea compound and preparation thereof and application thereof to metal ore floatation | |
| CN102753485B (en) | Auxiliary method for sulfide flotation | |
| CN110548592B (en) | Beneficiation method for improving comprehensive recovery index of complex low-grade molybdenum multi-metal ore | |
| CN102464599A (en) | Amido methyl xanthogenic acid cyanoethyl ester compound, preparation method and collecting agent thereof | |
| CN101698161B (en) | Flotation collector and preparation method thereof | |
| CN102503874B (en) | Thiourea compound, application thereof to metal ore flotation and preparation of thiourea compound | |
| CN104741243A (en) | Non-ferrous metal ore flotation collector with mercapto-hydroxamic acid group structure and preparation method and application thereof | |
| CN102464600A (en) | Amido ethyl xanthogenate cyanoethyl ester compound, preparation method and collecting agent thereof | |
| CN110846496B (en) | Sulfating roasting smelting method of sulfur-containing copper-cobalt concentrate | |
| CN102503873A (en) | Diltiazem allene amidoxime compound, application of diltiazem allene amidoxime compound in flotation of metal mine and preparation method for diltiazem allene amidoxime compound | |
| CN103691572A (en) | Collecting agent for improving beneficiation index of associated gold and silver | |
| CA1278110C (en) | Neutral hydrocarboxycarbonyl thiourea sulfide collectors | |
| CA2569869C (en) | Collector for sulfidic ores | |
| CN107899755B (en) | Synergist for flotation of refractory copper oxide ore | |
| CN102744161A (en) | Separation method of nickel-copper mixed concentrate containing platinum-palladium mineral | |
| CN109967262B (en) | Noble metal ore flotation reagent and application thereof | |
| CN111482278A (en) | Copper oxide ore flotation method | |
| CN108704767B (en) | Combined inhibitor and application thereof in separation of molybdenum-containing and other metal sulfide ores | |
| CN114100864B (en) | Agent and method for flotation separation of chalcopyrite-iron sulfide minerals | |
| CN114100863A (en) | Application of alpha-enol ketone in lead sulfide mineral flotation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |