EP0107562A1 - Concentration of ores by flotation and collector reagents used therefor - Google Patents

Concentration of ores by flotation and collector reagents used therefor Download PDF

Info

Publication number
EP0107562A1
EP0107562A1 EP83401957A EP83401957A EP0107562A1 EP 0107562 A1 EP0107562 A1 EP 0107562A1 EP 83401957 A EP83401957 A EP 83401957A EP 83401957 A EP83401957 A EP 83401957A EP 0107562 A1 EP0107562 A1 EP 0107562A1
Authority
EP
European Patent Office
Prior art keywords
flotation
ores
polysulfide
concentration
reagents used
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
Application number
EP83401957A
Other languages
German (de)
French (fr)
Other versions
EP0107562B1 (en
Inventor
Jacques Maurice
Patrice Guesnet
Pierre Tozzolino
Guy Muller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe National Elf Aquitaine
Societe Nationale Elf Aquitaine Production SA
Original Assignee
Societe National Elf Aquitaine
Societe Nationale Elf Aquitaine Production SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Societe National Elf Aquitaine, Societe Nationale Elf Aquitaine Production SA filed Critical Societe National Elf Aquitaine
Publication of EP0107562A1 publication Critical patent/EP0107562A1/en
Application granted granted Critical
Publication of EP0107562B1 publication Critical patent/EP0107562B1/en
Expired legal-status Critical Current

Links

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
    • B03D1/012—Organic compounds containing sulfur
    • 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

  • the present invention relates to the enrichment of ores by flotation with organic collectors, constituted by thio compounds. More specifically, it targets the processing of ores based on heavy metal oxides and sulphides.
  • the present invention is based on the discovery that the collecting properties of a thio compound can be intensified by a certain accumulation of sulfur atoms in the molecules of these compounds.
  • dialkyl polysulfides can give better results than the corresponding mercaptan; this is surprising theoretically, since polysulfides have a molecular structure with two lipophilic chains. This fact is all the more unexpected since the alkyl polysulfides with more C a are even less soluble in water than the mercaptans.
  • the process according to the invention consists in carrying out the flotation of ores or minerals in the general manner, known per se, but with at least one dihydro-carbyl polysulfide as collector, or jointly with a collector of known type, this or these polysulphides being represented by the formula where R and R ', similar or different, are alkyls or alkenyls which can carry substituents and x is a number with an average value of 2 to 8.
  • the substituents of the hydrocarbon groups R or / and R ' can be other aliphatic, cycloaliphatic or aryl radicals, halogens, nitriles or functional groups, for example OH, -COOH, NO 2 , NH 2 , CONH 2 , esters, carbonyls, etc.
  • Functional substituents, providing affinity for water, are particularly favorable.
  • the groups R and / and R ' are generally in C 1 to C18 linear or branched, and especially in C4 to C 1 2 "
  • a method of preparing such polysulphides which consists in treating, for example, the corresponding mercaptan with sulfur, in the presence of an amine as catalyst, according to the reaction:
  • This process actually provides a mixture of polysulfides of different numbers of S atoms, where x is actually an average of these numbers.
  • the polysulfides according to the invention are practically insoluble in water, they can be introduced into the ore pulp to be treated in the form of a solution in a solvent, in that of emulsion or extremely fine dispersion.
  • a solvent in that of emulsion or extremely fine dispersion.
  • the emulsion can be produced by mixing with a surface-active liquid such as polyethoxylated polyol or alkylphenol, petroleum sulfonate, polyalkoxylated mercaptan, a fatty acid ester of polyoxyalkylene or sorbitan, etc.
  • the aqueous or other dispersion it can be obtained by wet micronization.
  • the molar proportions of the new collectors, according to the invention, to be used in flotation are the same as those of the known technique, that is to say in general about 0.05 to 0.5, and more often of 0.1 to 0.25 moles per tonne of ore.
  • a series of flotation tests is carried out on copper sulphide ore from the South African mine at Palabora, with a Cu content of 0.45 to 0.48%. 600 g of this ore are ground to a fineness such that 76% of the powder passes through a 148 micron mesh sieve.
  • the product After adding the necessary adjuvants, the product is subjected to flotation for 20 minutes at pH 7.5, in a 2.5-liter laboratory cell of the MINEMET M 130 type, in the presence of methyl-isobutyl carbinol as a foaming agent. , added at a rate of 25 g per tonne of ore.
  • the collectors are introduced in the form of mixtures of 57.5% by weight of thio compounds with 42.5% of tensio-ac tif, nonyl phenol polyoxyethylene, known commercially under the trademark "SIMULSOL 730". These are, on the one hand, (examples 1 and 2) usual mercaptans in flotation and, on the other hand,. (Examples 3 to 6) of the polysulfides according to the invention; their proportion, in millimoles per tonne of ore, is indicated in the Table of results, which follows.
  • the Cu concentrations obtained are always higher, with the polysulphides, than those given by conventional collectors.
  • the pentasulfides allow a copper recovery comparable or superior to that of the mercaptans.

Abstract

Procédé d'enrichissement de minerais par flottation à l'aide d'un collecteur constitué par un thio composé, ce thio composé étant un polysulfure de dialkyle ou de dialkényle, linéaires ou ramifiés.Process for the enrichment of ores by flotation using a collector consisting of a compound thio, this compound thio being a dialkyl or dialkenyl polysulfide, linear or branched.

Description

La présente invention se rapporte à l'enrichissement de minerais par flottation avec des collecteurs organiques, constitués par des thio composés. Elle vise plus spécialement le traitement de minerais à base d'oxydes et de sulfures de métaux lourds.The present invention relates to the enrichment of ores by flotation with organic collectors, constituted by thio compounds. More specifically, it targets the processing of ores based on heavy metal oxides and sulphides.

Des composés renfermant du soufre dans leur molécule sont employés avec succès dans la technique de flottation : c'est notamment le cas des alkyl xanthates alcalins qui comptent parmi les meilleurs collecteurs connus jusqu'à présent. De même, considère-t-on comme bons collecteurs les mercaptans d'alkyles, surtout en C12 à C16' qui - malgré leur peu de solubilité dans l'eau - ont pu être avantageusement utilisés, émulsionnés avec des composés tensio-actifs.Compounds containing sulfur in their molecule are used with success in the technique of flotation: it is in particular the case of alkaline alkyl xanthates which count among the best collectors known until now. Similarly, do we consider as good collectors the alkyl mercaptans, especially in C 12 to C 16 ' which - despite their little solubility in water - could be advantageously used, emulsified with surfactant compounds .

La présente invention est basée sur la découverte que les propriétés collectrices d'un thio composé peuvent être intensifiées par une certaine accumulation d'atomes de soufre dans les molécules de ces composés. Ainsi a-t-on trouvé que des polysulfures de dialkyles peuvent donner des résultats meilleurs que le mercaptan correspondant ; c'est surprenant théoriquement, puisque les polysulfures présentent une structure moléculaire à deux chaînes lipophiles. Ce fait est d'ailleurs d'autant plus inattendu que les polysulfures d'alkyles à plus de Ca sont encore moins solubles dans l'eau que les mercaptans.The present invention is based on the discovery that the collecting properties of a thio compound can be intensified by a certain accumulation of sulfur atoms in the molecules of these compounds. Thus it has been found that dialkyl polysulfides can give better results than the corresponding mercaptan; this is surprising theoretically, since polysulfides have a molecular structure with two lipophilic chains. This fact is all the more unexpected since the alkyl polysulfides with more C a are even less soluble in water than the mercaptans.

Le procédé suivant l'invention consiste à effectuer la flottation de minerais ou de minéraux à la manière générale, connue en soi, mais avec au moins un polysulfure de dihydro- carbyle en tant que collecteur, ou conjointement avec un collecteur de type connu, ce ou ces polysulfures étant représentés par la formule

Figure imgb0001
où R et R', semblables ou différents, sont des alkyles ou alkényles pouvant porter des substituants et x est un nombre de valeur moyenne de 2 à 8.The process according to the invention consists in carrying out the flotation of ores or minerals in the general manner, known per se, but with at least one dihydro-carbyl polysulfide as collector, or jointly with a collector of known type, this or these polysulphides being represented by the formula
Figure imgb0001
 where R and R ', similar or different, are alkyls or alkenyls which can carry substituents and x is a number with an average value of 2 to 8.

Les substituants des groupes hydrocarbonés R ou/et R' peuvent être d'autres radicaux aliphatiques, cycloalipha- tiques ou aryliques, des halogènes, nitriles ou de groupes fonctionnels, par exemple des OH, -COOH, N02, NH2, CONH2, esters, carbonyles, etc. Des substituants fonctionnels, procurant de l'affinité pour l'eau, sont particulièrement favorables.The substituents of the hydrocarbon groups R or / and R 'can be other aliphatic, cycloaliphatic or aryl radicals, halogens, nitriles or functional groups, for example OH, -COOH, NO 2 , NH 2 , CONH 2 , esters, carbonyls, etc. Functional substituents, providing affinity for water, are particularly favorable.

Pratiquement, les groupes R ou/et R' sont en général en C1 à C18 linéaires ou ramifiés, et surtout en C4 à C12"In practice, the groups R and / and R 'are generally in C 1 to C18 linear or branched, and especially in C4 to C 1 2 "

On connait un mode de préparation de tels polysulfures, qui consiste à traiter par exemple le mercaptan correspondant par du soufre, en présence d'une amine comme catalyseur, suivant la réaction :

Figure imgb0002
A method of preparing such polysulphides is known, which consists in treating, for example, the corresponding mercaptan with sulfur, in the presence of an amine as catalyst, according to the reaction:
Figure imgb0002

Ce procédé fournit en réalité un mélange de polysulfures de différents nombres d'atomes de S, x étant en fait une moyenne de ces nombres.This process actually provides a mixture of polysulfides of different numbers of S atoms, where x is actually an average of these numbers.

Bien qu'à partir de C8, les polysulfures suivant l'invention soient pratiquement insolubles dans l'eau, ils peuvent être introduits dans la pulpe de minerai à traiter sous la forme de solution dans un solvant, sous celle d'émulsion ou de dispersion extrêmement fine. Ainsi, peut-on employer le polysulfure en solution dans de l'alcool, du sulfure de carbone, du diméthyl sulfoxide, du benzène, du kérosène, de l'huile ou autre solvant approprié. L'émulsion peut être produite par mélange avec un liquide tensio-actif tel que polyol ou alkyl-phénol polyéthoxylé, un sulfonate de pétrole, un mercaptan polyalkoxylé, un ester d'acide gras de polyoxyalkylène ou de sorbitan, etc.Although from C 8 , the polysulfides according to the invention are practically insoluble in water, they can be introduced into the ore pulp to be treated in the form of a solution in a solvent, in that of emulsion or extremely fine dispersion. Thus, can we use polysulfide dissolved in alcohol, carbon sulfide, dimethyl sulfoxide, benzene, kerosene, oil or other suitable solvent. The emulsion can be produced by mixing with a surface-active liquid such as polyethoxylated polyol or alkylphenol, petroleum sulfonate, polyalkoxylated mercaptan, a fatty acid ester of polyoxyalkylene or sorbitan, etc.

Quant à la dispersion aqueuse ou autre, elle peut s'obtenir par la micronisation humide.As for the aqueous or other dispersion, it can be obtained by wet micronization.

Les proportions molaires des nouveaux collecteurs, suivant l'invention, à employer dans la flottation, sont les mêmes que celles de la technique connue, c'est-à-dire en général environ 0,05 à 0,5, et plus souvent de 0,1 à 0,25 mole par tonne de minerai.The molar proportions of the new collectors, according to the invention, to be used in flotation, are the same as those of the known technique, that is to say in general about 0.05 to 0.5, and more often of 0.1 to 0.25 moles per tonne of ore.

Les exemples qui suivent illustrent l'invention non limitativement.The examples which follow illustrate the invention without limitation.

EXEMPLES 1 à 6EXAMPLES 1 to 6

Une série d'essais de flottation est effectuée sur un minerai sulfuré de cuivre provenant de la mine Sud Africaine de Palabora, à teneur en Cu de 0,45 à 0,48%. 600 g de ce minerai sont broyés à une finesse telle que 76% de la poudre traversent un tamis à mailles de 148 microns.A series of flotation tests is carried out on copper sulphide ore from the South African mine at Palabora, with a Cu content of 0.45 to 0.48%. 600 g of this ore are ground to a fineness such that 76% of the powder passes through a 148 micron mesh sieve.

Après l'adjonction des adjuvants nécessaires, le produit est soumis à la flottation pendant 20 minutes à pH 7,5, dans une cellule de laboratoire de 2,5 litres du type MINEMET M 130, en présence de méthyl-isobutyl carbinol comme agent moussant, ajouté à raison de 25 g par tonne de minerai.After adding the necessary adjuvants, the product is subjected to flotation for 20 minutes at pH 7.5, in a 2.5-liter laboratory cell of the MINEMET M 130 type, in the presence of methyl-isobutyl carbinol as a foaming agent. , added at a rate of 25 g per tonne of ore.

Les collecteurs sont introduits sous la forme de mélanges de 57,5% en poids de thio composés avec 42,5% de tensio-actif, nonyl phénol polyoxyéthylène, connu dans le commerce sous la marque "SIMULSOL 730".. Ce sont, d'une part, (exemples 1 et 2) des mercaptans usuels en flottation et,d'autre part,. (exemples 3 à 6) des polysulfures suivant l'invention ; leur proportion, en millimoles par tonne de minerai, est indiquée dans le Tableau des résultats, qui suit.The collectors are introduced in the form of mixtures of 57.5% by weight of thio compounds with 42.5% of tensio-ac tif, nonyl phenol polyoxyethylene, known commercially under the trademark "SIMULSOL 730". These are, on the one hand, (examples 1 and 2) usual mercaptans in flotation and, on the other hand,. (Examples 3 to 6) of the polysulfides according to the invention; their proportion, in millimoles per tonne of ore, is indicated in the Table of results, which follows.

Les deux dernières colonnes de ce Tableau indiquent la teneur pourcent en Cu dans le concentré obtenu, ainsi que les % de Cu récupéré.

Figure imgb0003
The last two columns of this Table indicate the percentage Cu content in the concentrate obtained, as well as the% Cu recovered.
Figure imgb0003

Il en résulte que les concentrations en Cu, obtenues, sont toujours supérieures, avec les polysulfures, à celles que donnent les collecteurs classiques. En outre, à proportions molaires égales, les pentasulfures permettent une récupération en cuivre comparable ou supérieure à celles des mercaptans.As a result, the Cu concentrations obtained are always higher, with the polysulphides, than those given by conventional collectors. In addition, at equal molar proportions, the pentasulfides allow a copper recovery comparable or superior to that of the mercaptans.

EXEMPLES 7 à 14EXAMPLES 7 to 14

Des essais de flottation sont effectués avec chacun des minéraux désignés dans le tableau des résultats par :

Figure imgb0004
Flotation tests are carried out with each of the mi designated in the table of results by:
Figure imgb0004

Dans une cellule, on introduit 265 ml d'eau, 1 g de poudre fine de minéral et 3x10-4 g de collecteur à essayer, par litre ; ce collecteur est utilisé sous la forme d'une solution à 1% dans de l'éthanol.265 ml of water, 1 g of fine mineral powder and 3 × 10 -4 g of collector to be tested are introduced into a cell per liter; this collector is used in the form of a 1% solution in ethanol.

Le tableau ci-après donne les % de chaque minéral recueilli comme produit de la flottation.

Figure imgb0005
The table below gives the% of each mineral collected as a product of flotation.
Figure imgb0005

On peut constater que les polysulfures des exemples 8 à 13 donnent des résultats supérieurs à ceux du n-dodécyl mercaptan (exemple 14) couramment employé à l'heure actuelle.It can be seen that the polysulphides of Examples 8 to 13 give better results than those of n-dodecyl mercaptan (Example 14) commonly used at present.

EXEMPLES 15 à 20EXAMPLES 15 to 20

Essais sur la chalcopyrite avec 3 x 10-4 g/1 de collecteur.Chalcopyrite tests with 3 x 10 -4 g / 1 of collector.

Figure imgb0006
On voit qu'avec S2 et des alkyles à moins de 6 atomes de carbone les rendements sont mauvais.
Figure imgb0006
 We see that with S 2 and alkyls with less than 6 carbon atoms the yields are poor.

Claims (5)

1. Procédé d'enrichissement de minerais par flottation à l'aide d'un collecteur constitué par un polysulfure de deux groupes hydrocarbonés aliphatiques, caractérisé en ce que ces groupes, qui sont des alkyles ou des alkényles, comportent chacun 6 à 18 atomes de carbone.1. A method of enriching ores by flotation using a collector consisting of a polysulphide of two aliphatic hydrocarbon groups, characterized in that these groups, which are alkyls or alkenyls, each contain 6 to 18 atoms of carbon. 2. Procédé suivant la revendication 1, caractérisé en ce que le nombre moyen d'atomes de soufre,dans le polysulfure, est de 2 à 8.2. Method according to claim 1, characterized in that the average number of sulfur atoms in the polysulfide is from 2 to 8. 3. Procédé suivant la revendication 2, caractérisé en ce que le nombre moyen d'atomes de soufre est de 3 à 5.3. Method according to claim 2, characterized in that the average number of sulfur atoms is from 3 to 5. 4. Procédé suivant une des revendications 1 à 3, caractérisé en ce qu'au moins un des groupes hydrocarbonés du polysulfure porte un ou plusieurs substituants fonctionnels, en particulier des -OH, -COOH, -N02, -NH2, -CONH2' esters ou/et carbonyles.4. Method according to one of claims 1 to 3, characterized in that at least one of the hydrocarbon groups of the polysulfide carries one or more functional substituents, in particular -OH, -COOH, -N0 2 , -NH 2 , -CONH 2 ' esters or / and carbonyls. 5. Procédé suivant une des revendications 1 à 4, caractérisé en ce que le polysulfure est mis à l'état d'une dispersion extrêmement fine dans un liquide, notamment dans l'eau, pour être introduit dans la pulpe de minerai à traiter.5. Method according to one of claims 1 to 4, characterized in that the polysulfide is brought to the state of an extremely fine dispersion in a liquid, in particular in water, to be introduced into the ore pulp to be treated.
EP83401957A 1982-10-13 1983-10-07 Concentration of ores by flotation and collector reagents used therefor Expired EP0107562B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8217128 1982-10-13
FR8217128A FR2534493B1 (en) 1982-10-13 1982-10-13 ENRICHMENT OF ORES BY FLOTATION AND COLLECTING AGENTS EMPLOYED THEREFOR

Publications (2)

Publication Number Publication Date
EP0107562A1 true EP0107562A1 (en) 1984-05-02
EP0107562B1 EP0107562B1 (en) 1987-08-12

Family

ID=9278233

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83401957A Expired EP0107562B1 (en) 1982-10-13 1983-10-07 Concentration of ores by flotation and collector reagents used therefor

Country Status (9)

Country Link
US (1) US4554137A (en)
EP (1) EP0107562B1 (en)
AU (1) AU562923B2 (en)
CA (1) CA1215547A (en)
DE (1) DE107562T1 (en)
ES (1) ES526758A0 (en)
FI (1) FI74892C (en)
FR (1) FR2534493B1 (en)
ZA (1) ZA837622B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4735711A (en) * 1985-05-31 1988-04-05 The Dow Chemical Company Novel collectors for the selective froth flotation of mineral sulfides
US5338338A (en) * 1992-09-22 1994-08-16 Geobiotics, Inc. Method for recovering gold and other precious metals from carbonaceous ores
US5364453A (en) * 1992-09-22 1994-11-15 Geobiotics, Inc. Method for recovering gold and other precious metals from carbonaceous ores

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1774183A (en) * 1927-05-13 1930-08-26 Barrett Co Concentration of minerals
GB362366A (en) * 1929-09-04 1931-12-01 Minerals Separation Ltd Improvements in or relating to concentration by froth flotation
US2027357A (en) * 1927-05-13 1936-01-07 Barrett Co Flotation of minerals
US3059774A (en) * 1961-07-31 1962-10-23 United States Borax Chem Method and means for beneficiating ores
FR2429617A1 (en) * 1978-06-27 1980-01-25 Elf Aquitaine Flotation collectors esp. for sulphide minerals - comprise organic thio cpds. esp. alkyl thio ethanol(s) (SW 28.1.80)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4341626A (en) * 1980-12-22 1982-07-27 American Cyanamid Company Process for the flotation of sulfide minerals employing alkylaryl hydrocarbon compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1774183A (en) * 1927-05-13 1930-08-26 Barrett Co Concentration of minerals
US2027357A (en) * 1927-05-13 1936-01-07 Barrett Co Flotation of minerals
GB362366A (en) * 1929-09-04 1931-12-01 Minerals Separation Ltd Improvements in or relating to concentration by froth flotation
US3059774A (en) * 1961-07-31 1962-10-23 United States Borax Chem Method and means for beneficiating ores
FR2429617A1 (en) * 1978-06-27 1980-01-25 Elf Aquitaine Flotation collectors esp. for sulphide minerals - comprise organic thio cpds. esp. alkyl thio ethanol(s) (SW 28.1.80)

Also Published As

Publication number Publication date
DE107562T1 (en) 1984-09-13
FI74892C (en) 1988-04-11
EP0107562B1 (en) 1987-08-12
ZA837622B (en) 1984-06-27
CA1215547A (en) 1986-12-23
FI833716A (en) 1984-04-14
AU2015483A (en) 1984-04-19
FI833716A0 (en) 1983-10-12
FR2534493B1 (en) 1986-05-30
AU562923B2 (en) 1987-06-25
ES8501251A1 (en) 1984-12-01
FR2534493A1 (en) 1984-04-20
FI74892B (en) 1987-12-31
ES526758A0 (en) 1984-12-01
US4554137A (en) 1985-11-19

Similar Documents

Publication Publication Date Title
EP0107561B1 (en) Flotation of ores
CN101337206B (en) Sulphide ore floation collector and use method of diacyl bis-thiourea and preparation method thereof
CN110563621B (en) Method for utilizing byproduct sodium 2-mercaptoacetate in thiourethane production process
CA1096059A (en) No translation available
CA2470343C (en) Compound of mercaptans usable in an ore floating process
CA1137656A (en) Mineral flotation collectors
EP0107562B1 (en) Concentration of ores by flotation and collector reagents used therefor
DE3601286A1 (en) COLLECTING AGENTS FOR THE SELECTIVE FLOTATION OF LEAD AND ZINC PLUGS AND METHOD FOR THE PRODUCTION THEREOF
EP0088002B1 (en) Process for liquid-liquid extraction of metals from an aqueous solution using a micro-emulsion
CN113210134A (en) Preparation and application of acyl carboxyl azothioic ester compound
PL197493B1 (en) Collector for non iron metal sulphide preparation
CN110560270B (en) Sand composite inhibitor and application thereof
CA2998063C (en) Flotation agent of thiol ether structure
US2134706A (en) Process of flotation and agent therefor
EP0193630B1 (en) Ore flotation with combined collectors
FR2555073A1 (en) METHODS FOR FLOTATING INSOLUBLE MATERIALS AND THE SYLVITY OF A POTASSY ORE
FR2489714A1 (en) Foam flotation sepn. of silica from iron ores - using water dispersible aliphatic ether amine or salt as collector
US4528141A (en) Process for producing trithiocarbonic acid esters
US4561971A (en) Ore flotation and flotation agents for use therein
SU1085064A1 (en) Collector for flotation of sulfide lead-zinc ores
SU822901A1 (en) Sulfide ore flotation collector
RU2054970C1 (en) Collector for sulfur copper-zinc ores flotation
US4594150A (en) Mono- and dithioic esters, their preparation and uses
US1933179A (en) Flotation process and mineral collecting agent
CN117980074A (en) Collector, floating beneficiation method and compound

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): DE SE

17P Request for examination filed

Effective date: 19840607

R17P Request for examination filed (corrected)

Effective date: 19840612

DET De: translation of patent claims
RBV Designated contracting states (corrected)

Designated state(s): SE

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): SE

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19921014

Year of fee payment: 10

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19931008

EUG Se: european patent has lapsed

Ref document number: 83401957.2

Effective date: 19940510