US3853751A - Flotation of sulfide ores using dithiocarbamates - Google Patents

Flotation of sulfide ores using dithiocarbamates Download PDF

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Publication number
US3853751A
US3853751A US00224616A US22461672A US3853751A US 3853751 A US3853751 A US 3853751A US 00224616 A US00224616 A US 00224616A US 22461672 A US22461672 A US 22461672A US 3853751 A US3853751 A US 3853751A
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US
United States
Prior art keywords
group
flotation
carbon atoms
hydrocarbyl
ore
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
Application number
US00224616A
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English (en)
Inventor
G Harris
D Collins
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.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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
Priority to BE795146D priority Critical patent/BE795146A/xx
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Priority to US00224616A priority patent/US3853751A/en
Priority to ZA730635A priority patent/ZA73635B/xx
Priority to DE19732305245 priority patent/DE2305245A1/de
Priority to AU51809/73A priority patent/AU5180973A/en
Priority to ES411394A priority patent/ES411394A1/es
Priority to IT4810273A priority patent/IT977234B/it
Priority to CA163,096A priority patent/CA996133A/en
Priority to JP48016048A priority patent/JPS4890901A/ja
Priority to FR7304430A priority patent/FR2171281B1/fr
Priority to GB627773A priority patent/GB1421466A/en
Priority to OA54830A priority patent/OA04288A/xx
Priority to TR1741073A priority patent/TR17410A/xx
Priority to ZM18/73*UA priority patent/ZM1873A1/xx
Application granted granted Critical
Publication of US3853751A publication Critical patent/US3853751A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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 novel dithiocarbamate esters and their use as flotation agents in the separation of sulfide ores.
  • Flotation is a process of treating a mixture of finely divided mineral solids, e.g., a pulverulent ore, suspended in a liquid whereby a portion of such solids are separated from other finely divided mineral solids, e.g., clays and other like materials present in the ore, by introducing a gas (or providing a gas in situ) in the liquid to produce a frothy mass containing certain of the solids on the top of the liquid, and leaving suspended (unfrothed) other solid components of the ore.
  • a gas or providing a gas in situ
  • Flotation is based on the principle that introducing a gas into a liquid containing solid particles of different materials suspended therein causes adherence of some gas to certain suspended solids and not to others and makes the particles having the gas thus adhered thereto lighter than the liquid. Accordingly, they rise to the top of the liquid to form a froth.
  • collectors e.g., high carbon chain com pounds such as collectors for sulfide minerals including xanthates, thionocarbamates, and the like
  • frothers which impart the property of forming a stable froth, e.g., natural oils such as pine oil and eucalyptus oil, modifiers such as activators to induce flotation in the presence of a collector, e.g., copper sulfate
  • depressants e.g., sodium cyanide, which tend to prevent a collector from functioning as such on a mineral which it is desired to retain in the liquid, and thereby discourage a substance from being carried up and forming a part of the froth
  • pH regulators to produce optimum metallurgical results, e.g., lime, soda ash and the like.
  • additives of the above'type are selected for use according to the nature of the ore, the mineral sought to be recovered, and the other additaments which are to be used in combination therewith.
  • the present invention concerns novel compounds corresponding to the formula wherein R represents H, a hydrocarbyl group, or a heterohydrocarbyl group, wherein said groups can be substituted with up to two functional groups and contain from 1 to 10 carbon atoms; R represents an alkylene or heteroalkylene group having a heteroatom substituted in the carbon chain, and R represents a hydrocarbyl or heterohydrocarbyl group, except for aryl, wherein either of said groups can be substituted except in the alpha position with up to two functional groups.
  • the novel compounds can be prepared by the reaction of an amino alcohol with a trithiocarbonate ester and reacting the resulting hydroxyalkyl dithiocarbamate product with an acyl halide.
  • novel compounds can be employed to improve the flotation process of sepa rating sulfide minerals from ores by employing an effective quantity of at least one of the novel compounds set forth herein in the flotation process.
  • novel compounds are also useful as fungicides and herbicides.
  • R represents H, a hydrocarbyl group selected from the group consisting of alkyl (e.g., methyl, ethyl, propyl, butyLdecyl) or alkenyl (e.g., vinyl, allyl, propenyl) containing up to 10 carbon atoms, alkaryl (e.g., tolyl), aryl (e.g., phenyl), aralkyl (e.g., benzyl, phenethyl), cycloalkyl (e.g., cyclopropyl, cyclohexyl), cycloalkenyl (e.g., cyclohexenyl), aralkenyl (e.g., phenylvinyl, cinnamyl), or acylalky] (e.g., acetylmethyl) groups, wherein the a hydrocarbyl group selected from the group consisting of alkyl (e.g.,
  • hexenyl) group preferably containing up to eight carbon atoms, an aralkyl group'(e.g., benzyl, phenethyl, phenylpropyl), preferably containing from one to three carbon atoms, in the alkyl portion, and an cycloalkyl or cycloalkenyl group, preferably containing from three to eight carbon atoms, wherein said hydrocarbyl groups can be substituted, except in the alpha position, with up to two identical or different functional groups prefera l5 METHODS OF PREPARATION
  • the novel compounds as defined herein can be prepared, for example, by reacting an amino alcohol with a trithiocarbonate ester to prepare a hydroxy dithiourethane and then acylating the HOR, moiety with an 'acyl halide, anhydride or ketene.
  • the reactions can be represented as follows:
  • novel compounds as defined herein have a special utility as flotation collectors and can be employed in standard flotation processes to concentrate nickel and molybdenum sulfides and other like minerals from sulfide ores in preference to iron sulphides.
  • a pulp is first prepared by wet grinding a sulphide containing ore to a suitable size with or without a pH modifier.
  • a suitable frothing agent is then added, e.g., pine oil, cresylic acid, polyalkoxyparaffin and the like.
  • An effective quantity of a flotation collector compound as defined herein is then added, usually ranging from about 0.01 lbs. to about 0.25 lbs. per ton of pulp, and thepulp is usually agitated and aerated.
  • Sulfide minerals e.g., copper, nickel, zinc, molybdenum sulphides, and other like sulfide minerals collect as a froth which is readily over-flowed or skimmed off from the residual gangue and other nondesired materials and the metal values therein recovered.
  • CT C1 of R R and the acylatmg agent are set forth tn the fol- (3) cyanoacetyl chloride: 0 lowing Table 1, together Wltl'l the empirical formulas of Y NC C lg C1 the products which are formed.
  • Example 2 The collector of Example 2 was also tested on a nickel sulfide ore from Canada, a copper ore from North Central U.S.A. and a molybdenum ore from South Western U.S.A.
  • the sample was ground for minutes at 60.5 percent solids with 0.4 lbs/ton of lime and 0.09 lbs/ton of collector.
  • the pulp was conditioned for one minute with 0.064 lbs/ton of a standard commercial frother. The pulp was then floated for 5 minutes and the concentrate tailings assayed for copper, iron and nickel.
  • the copper ore from North Central U.S.A. was treated in the following manner: Samples of ore were ground for 5 min. at a pulp density of 62.5 percent solids with 0.8 lbs/ton of lime and 0.128 lbs/ton of collector. The pulp was then transferred to a commercial laboratory flotation cell and conditioned for l min.
  • the molybdenum ore from South Western U.S.A. was tested in the following manner: Samples of ore were ground for 4 mins. at a pulp density of 62.5 percent solids with 0.4 lbs/ton of lime and 0.048 lbs/ton of collector. The pulp was then transferred to a commercial laboratory flotation cell and conditioned for l min. with 0.078 lbs/ton of a standard 'frother. A concentrate was then removed in 5 mins. of flotation at a and alkenylchloroformates such as and the like.
  • a process of concentrating sulfide ores by flotation which comprises subjecting a sulfide ore of copper, nickel or molybdenum, in the form ofa pulp, to a flotation process in the presence of a flotation collector for said sulfides comprising a compound corresponding to the formula wherein R represents a member selected from the group consisting of H, a hydrocarbyl or a heterohydrocarbyl group; R represents a member selected from the group consisting of an alkylene or heteroalkylene group having the hetero atom substituted in the carbon chain and R represents a hydrocarbyl radical other than an aryl group.
  • R represents a member selected from the group consisting of a hydrocarbyl or heterohydrocarbyl radical containing up to two functional groups substituted thereon, and R represents a hydrocarbyl radical, other than an aryl group having up to two functional groups substituted thereon, other-than in the alpha position of said hydrocarbyl.
  • R represents H, a hydrocarbyl radical selected from the group consisting of alkyl or alkenyl containing up to carbon atoms, aryl, alkaryl; aralkyl, cycloalkyl, cycloalkenyl, aralkenyl or acylalkyl groups wherein the acyclic carbon chain portion contains up to three carbon atoms and the cyclic group contains from five to 10 carbon atoms, a heterohydrocarbyl selected from the group consisting of alkoxy, alkenyloxy, alkoxy carbonyl, alkoxycarbonylalkyl, aryloxy, alkylthio or arylthio groups; R represents a member selected from the group consisting of an alkylene or heteroalkylene group containing up to eight carbon atoms wherein the hetero atom in the heteroalkylene group is selected from the group consisting of O, S, and
  • X is a hydrocarbyl radical and R represents a hydrocarbyl radical selected from the group consisting of an alkyl or alkenyl group, containing up to eight carbon atoms, an aralkyl, containing from one to three carbon atoms in the alkyl portion, and cycloalkyl or cycloalkenyl group, containing from three to eight carbon atoms, wherein R, R and R are further characterized in that the total number of carbon atoms in said groups range from about four to about 25.
  • R and R contain up to two functional groups other than in the alpha position of R selected from the group consis'ting of halo, alkoxy, cyano, acetyl or lower dialkylammo group.

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Manufacture And Refinement Of Metals (AREA)
US00224616A 1972-02-08 1972-02-08 Flotation of sulfide ores using dithiocarbamates Expired - Lifetime US3853751A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
BE795146D BE795146A (fr) 1972-02-08 Perfectionnements relatifs a la flottation des minerais sulfures
US00224616A US3853751A (en) 1972-02-08 1972-02-08 Flotation of sulfide ores using dithiocarbamates
ZA730635A ZA73635B (en) 1972-02-08 1973-01-29 Flotation of sulfide ores using dithiocarbamates
DE19732305245 DE2305245A1 (de) 1972-02-08 1973-02-02 Flotation von sulfiderzen unter verwendung von dithiocarbamidsaeurederivaten
AU51809/73A AU5180973A (en) 1972-02-08 1973-02-05 Flotation of sulfide ores using dithiocarbamates
IT4810273A IT977234B (it) 1972-02-08 1973-02-07 Procedimento di flottazione per minerali solfuri e composizione per esso adatta
ES411394A ES411394A1 (es) 1972-02-08 1973-02-07 Mejoras introducidas en un procedimiento de concentracion de minerales de sulfuro por flotacion.
CA163,096A CA996133A (en) 1972-02-08 1973-02-07 Flotation of sulfide ores using dithiocarbamates
JP48016048A JPS4890901A (Direct) 1972-02-08 1973-02-08
FR7304430A FR2171281B1 (Direct) 1972-02-08 1973-02-08
GB627773A GB1421466A (en) 1972-02-08 1973-02-08 Dithiocarbamates and uses thereof
OA54830A OA04288A (fr) 1972-02-08 1973-02-08 Flottation de minerais de sulfures en utilisant des dithiocarbamates.
TR1741073A TR17410A (tr) 1972-02-08 1973-02-08 Suelfuer cevherlerinin ditiyokarbamatlar kullanarak yuezdueruelmesi
ZM18/73*UA ZM1873A1 (en) 1972-02-08 1973-02-12 Flotation of sulfide ores using dithiocarbamates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00224616A US3853751A (en) 1972-02-08 1972-02-08 Flotation of sulfide ores using dithiocarbamates

Publications (1)

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US3853751A true US3853751A (en) 1974-12-10

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US00224616A Expired - Lifetime US3853751A (en) 1972-02-08 1972-02-08 Flotation of sulfide ores using dithiocarbamates

Country Status (7)

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US (1) US3853751A (Direct)
AU (1) AU5180973A (Direct)
BE (1) BE795146A (Direct)
DE (1) DE2305245A1 (Direct)
FR (1) FR2171281B1 (Direct)
GB (1) GB1421466A (Direct)
ZA (1) ZA73635B (Direct)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4098686A (en) * 1976-03-19 1978-07-04 Vojislav Petrovich Froth flotation method for recovering of minerals
US4618461A (en) * 1983-07-25 1986-10-21 The Dow Chemical Company O,O'-, O,S'- or S,S'-dithiodialkylene-bis(mono- or dihydrocarbyl carbamothioates) and S,S'-dithiodialkylene-bis(mono- or dihydrocarbyl carbamodithioates) and method of preparation thereof
US4702822A (en) * 1985-07-12 1987-10-27 The Dow Chemical Company Novel collector composition for froth flotation
US5958462A (en) * 1997-05-23 1999-09-28 Mclean; Linsey Therapeutic bath salts and method of use
CN113102113A (zh) * 2021-04-13 2021-07-13 中南大学 一种方铅矿与含锌脉石选择性浮选分离药剂和方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN85107378A (zh) * 1984-09-13 1987-03-18 陶氏化学公司 从原煤中回收有用煤的起泡剂组合物和泡沫浮选方法
CN111495608A (zh) * 2020-05-14 2020-08-07 沈阳有色金属研究院有限公司 一种高效回收多金属硫化矿中铅锌硫的浮选工艺

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2375083A (en) * 1943-08-05 1945-05-01 Monsanto Chemicals Preparation of disulphides
US3424730A (en) * 1964-03-06 1969-01-28 Dow Chemical Co Vinylidenearylenealkylene carbamates and polymers thereof
US3464551A (en) * 1967-11-01 1969-09-02 American Cyanamid Co Dialkyl dithiocarbamates as collectors in froth flotation
US3590996A (en) * 1969-02-03 1971-07-06 Dow Chemical Co Floatation of sulfide ores
US3590997A (en) * 1969-02-13 1971-07-06 Dow Chemical Co Flotation of sulfide ores

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2375083A (en) * 1943-08-05 1945-05-01 Monsanto Chemicals Preparation of disulphides
US3424730A (en) * 1964-03-06 1969-01-28 Dow Chemical Co Vinylidenearylenealkylene carbamates and polymers thereof
US3464551A (en) * 1967-11-01 1969-09-02 American Cyanamid Co Dialkyl dithiocarbamates as collectors in froth flotation
US3590996A (en) * 1969-02-03 1971-07-06 Dow Chemical Co Floatation of sulfide ores
US3590997A (en) * 1969-02-13 1971-07-06 Dow Chemical Co Flotation of sulfide ores

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4098686A (en) * 1976-03-19 1978-07-04 Vojislav Petrovich Froth flotation method for recovering of minerals
US4618461A (en) * 1983-07-25 1986-10-21 The Dow Chemical Company O,O'-, O,S'- or S,S'-dithiodialkylene-bis(mono- or dihydrocarbyl carbamothioates) and S,S'-dithiodialkylene-bis(mono- or dihydrocarbyl carbamodithioates) and method of preparation thereof
US4702822A (en) * 1985-07-12 1987-10-27 The Dow Chemical Company Novel collector composition for froth flotation
US5958462A (en) * 1997-05-23 1999-09-28 Mclean; Linsey Therapeutic bath salts and method of use
CN113102113A (zh) * 2021-04-13 2021-07-13 中南大学 一种方铅矿与含锌脉石选择性浮选分离药剂和方法
CN113102113B (zh) * 2021-04-13 2022-01-18 中南大学 一种方铅矿与含锌脉石选择性浮选分离药剂和方法

Also Published As

Publication number Publication date
FR2171281A1 (Direct) 1973-09-21
BE795146A (fr) 1973-08-08
ZA73635B (en) 1974-03-27
GB1421466A (en) 1976-01-21
AU5180973A (en) 1974-08-08
DE2305245A1 (de) 1973-08-23
FR2171281B1 (Direct) 1978-03-03

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