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

• FLOATATION OF SULFIDE ORES BACKGROUND 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 compounds 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 flotation principle is applied in a number of mineral separation processes among which is the selective separation of such minerals as sulfide copper minerals, sulfide zinc minerals, sulfide molybdenum minerals and others from sulfide iron minerals.
• the present invention concerns a novel class of compounds. These compounds can be employed as collection agents in a flotation process. With some of these compounds better recoveries are realized and with others, improved selectivity is achieved. Certain of these compounds produce improvement in both aspects.
• 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 xanthate ester and contacting the product produced with an acyl halide.
• novel compounds can be employed to improved the flotation process of separating 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.
• novel compounds of the present invention correspond to the formula wherein R represents H, a hydrocarbyl group selected from the group consisting of alkyl or alkenyl containing up to 10 carbon atoms, alkaryl, aryl, aralkyl, cycloalkyl, cycloalkenyl, aralkenyl or acylalkyl groups, wherein the acyclic carbon chain portions preferably contain up to 3 carbon atoms and the cyclic group contains from 5 to 10 carbon atoms and a heterohydrocarbyl radical selected from the group consisting of alkoxy, alkenyloxy, alkoxy carbonyl, alkoxycarbonylalkyl, aryloxy, arylalkoxy, alkylthio and arylthio groups, wherein said heterohydrocarbyl groups can contain up to two identical or different functional groups preferably selected from the group consisting of halo, alkoxy, cyano, and di-loweralkyla
• novel compounds as defined herein can be prepared, for example, by reacting an aminoalcohol with a xanthate ester to prepare a hydroxy-thionourethane and then acylating the HO-R -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 copper sulfide and other like minerals from sulfide ores in preference to iron sulfides
• a pulp is first prepared by wet grinding a sulfide 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 Example 1
• a novel compound corresponding to the formula was prepared in the following manner.
• Example 2 A new compound within the scope of the invention defined herein and corresponding to the formula was prepared in the following manner: A solution of 16.3 grams of isopropyl 2-hydroxyethylthionocarbamate in 25 ml. of 50 percent diketene/acetone was let stand for a week. The oil obtained on addition of 100 ml. of water was taken up in ether. This extract was dried over MgSO The solid was later removed by filtration and the ether removed by distillation, the last traces with a vacuum. The structure as set forth above was confirmed by infrared and NMR analyses. The yield was 89 percent. The calculated and actual elemental analysis for the product corresponding to the formula set forth above is Percent Example 3 Another novel compound within the scope of the present invention is prepared in the following manner. The reaction is set forth as:
• the compound is prepared as follows.
• Example 4 A new compound corresponding to the formula was prepared in the following manner.
• Example 5 A new compound within the scope of the present invention was prepared corresponding to the formula
• a starting material compound corresponding to the formula was prepared as follows: To 18.1 grams of 2-(2-hydroxyethyl)- thioethylamine was added 22.5 grams of methyl isopropylx anthate. The mixture was heated in a hot water bath to drive off most of the evolved CH SH gas. The mixture was then heated to 65 C. under a reduced pressure of 20 mm. to remove the last traces of CH Sl-l. The yield was nearly quantitative. The structure of this starting material was 4by infrared and NMR analysis. To 17.9 grams of the so-prepared starting material in 35 ml. of ether and 8.9 ml.
• Example 7 Various species of flotation collector compounds within the scope of the present invention were employed in the recovery remaining ether and the methyl acetate were removed under 5 of pp and molybdenum fr m a S lfide ore obtained from d d pressure f 4 b h i to 70 C 19 7 grams or South America employing the following procedure: The ore about a 93 percent yield of the product was obtained, Th sample was ground for 5 minutes at 66 percent solids with no structure of the novel compound corresponding to that set reagents The p p Cohdmohed 8 minutes with forth above was continued by infrared and NMR analysis.
• Eleof a Speclfic flotahoh collector compound and menu analysis gave 452 percent 3 percent and 0.13 lbs./ton of a standard frother. During the conditioning percent. Calculated analysis for a compound corresponding to Penod the P was adlusted 5 3 value of 3909i The P p m above structure is (3,453 percent percent and was then floated for seven minutes and the tailings assayed for 3 percent copper and molybdenum.
• a standard flotation collector consisting of a thionocarbamate compound corresponding to the Example 6 15 formula
• Other species of compounds within the scope of the present H s CH invention were prepared according to one of the procedures g 3 set forth in Examples l4. The starting materials consisted of 1 2 a compound corresponding to the formula OH;
• OHCHFIL OCH(CHJ)E s o 0. 03 0. 23s 86. s
• Example 8 Various novel collectors within the scope of the present invention were tested on a copper sulfide ore from the Southeastern United States. The ore sample was ground for 4% minutes at 59 percent solids with 2.0 lbs/ton of lime. The pulp was conditioned for 2 minutes with an amount of a specific collector and 0.16 lbs/ton of a standard frother at a pH of 10.5. The pulp was then floated for 8% minutes and the tailings assayed for copper. The results obtained are set forth in the following Table III. The same control flotation collector was employed as in Example 7.
• a sample of ore was ground at 60 percent solids to 35 percent minus 200 mesh Tyler. To the pulp was added 0.9 lbs/ton lime, 0.08 lbs/ton diesel oil, 0.01 lbs/ton of a collector compound to be tested and 0.06 lbs/ton frother. The ore was floated for 8 minutes. Both the concentrate and tailings were filtered, dried and assayed for Mo and Cu. The same control collector compound was employed as in Examples 7 and 8.
• the xanthate starting materials employed herein in the preparation of the novel compounds can be prepared in a manner well known in the art.
• an alcohol corresponding to R,OH, wherein R is the same as defined hereinbefore can be reacted as the corresponding alkali metal alkoxide, with CS, to prepare a product corresponding to the formula wherein M is the alkali metal ion.
• the product can then be contacted with, for example, methyl chloride, to prepare the corresponding xanthate ester i R C-SCH;
• Alcohols which may be employed include, for example, cyclohexanol, cyclohexenol, allyl alcohol, cinnamyl alcohol. 2-bromo-allyl alcohol; 2,3,5-trimethyl-3-hexanol; 2,3,4- trimethyl-Z-hexanol and the like.
• Acylating agents which can be used in preparing the novel compounds of the present invention can be prepared by converting carboxylic acids to the corresponding acyl chloride by contacting said acids with thionyl chloride by processes well known in the art.
• Carboxylic acids which may be employed in clude, for example, cinnamic acid, a-bromocaproic acid, pelargonic acid, methacrylic acid, 3-cyanophenylacetic acid, cyclohexylacetic acid, cyanoacetic acid, Z-phenoxybutanoic acid, methoxyacetic acid and the like.
• a compound corresponding to the formula can be prepared by reacting ethylenimine and pivalic acid to prepare a compound corresponding to the formula (CH3)3CC CHQCH3XHQ and reacting this compound with methyl isopropyl xanthate to Another compound corresponding to the formula is prepared by reacting 17.0 grams of aniosoyl chloride with 16.3 grams of ethyl 2-hydroxyethylthionocarbamate to produce the indicated compound having a molecular weight of 283.
• a. subjecting the sulfide containing ore in the form of a pulp to flotation collector comprising a compound corresponding the formula wherein R represents H, a hydrocarbyl radical selected from the group consisting of alkyl or alkenyl containing up to 10 carbon atoms, aryl, alkaryl, aralkyl, cycloalkyl, cycloalkenyl, aralkenyl or acylalkyl groups wherein the acyclic carbon chain portion contains up to 3 carbon atoms and the cyclic groups contains from 5 to 10 carbon atoms, a heterohydrocarbyl selected from the group consisting of alkoxy, alkenyloxy, alkoxy carbonyl, alkoxycarbonylalkyl, aryloxy, alkylthio, arylthio, or oxyalkyl group; R represents a member selected 0 from the group consisting of an alkylene or heteroalkylene wherein X is a member selected from the group consisting
• R and R contain up to two functional groups other than in the alpha position of R selected from the group consisting of halo, alkoxy, cyano, acetonyl, or di-loweralkylamino group.

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Citations (9)

• 1969
  • 1969-02-03 US US796159A patent/US3590996A/en not_active Expired - Lifetime
• 1970
  • 1970-01-06 ZA ZA700085A patent/ZA7000085B/xx unknown
  • 1970-01-06 GB GB689/70A patent/GB1293742A/en not_active Expired
  • 1970-01-28 ZM ZM11/70A patent/ZM1170A1/xx unknown
  • 1970-01-30 DE DE19702004105 patent/DE2004105A1/de active Pending
  • 1970-01-30 FR FR7003436A patent/FR2046117A5/fr not_active Expired
  • 1970-02-02 BE BE745341D patent/BE745341A/fr unknown
  • 1970-02-02 ES ES376141A patent/ES376141A1/es not_active Expired

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