Collecting agent and flotation beneficiation method

Abstract

A collector containing a compound represented by formula (1). (In formula (1), R1 represents an alkylene group having 3 to 8 carbon atoms, and at least one hydrogen atom in the alkylene group may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydrocarbon group having 1 to 12 carbon atoms, a hydrocarbyloxy group having 1 to 12 carbon atoms, and an acyloxy group having 6 to 12 carbon atoms; the substituents may be bonded to each other. And R2 represents a hydrogen atom or a linear or branched alkyl group having 1-16 carbon atoms (inclusive). > # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a collector and a flotation beneficiation method. Background Art

[0002] Conventionally, flotation separation for recovering minerals contained in ore has been known.

[0003] For example, Patent Document 1 describes a collector for flotation separation represented by the following formula (100). In formula (100), R 100 and R 101 are each independently hydrogen, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms. 100 and R 101 It may be substituted by a hydroxyl group, an alkoxy group having 1 to 12 carbon atoms, or a halogen group. 100 and R 101 Both of these are the case for hydrogen.

[0004] [Chemical formula 1]

[0005]

[0006] In addition, Patent Document 2 describes an activator for a non-sulfide mineral represented by the following formula (101). In formula (101), R 102 C n H 2n+1 It means that n is an integer greater than or equal to 0 and less than or equal to 4.

[0007] [Chemical formula 2]

[0008]

[0009] However, in the flotation separation of copper using the substances described in the above patent documents, the recovery amount of copper is insufficient. Therefore, a collector that increases the recovery amount of the target mineral is required.

[0010] Prior art literature

[0011] Patent Literature

[0012] Patent Document 1: Chinese Patent Application Publication No. 108296028

[0013] Patent Document 2: U.S. Patent No. 2724500 Summary of the invention

[0014] Problems to be solved by the invention

[0015] An object of the present disclosure is to provide a collector containing a compound that increases the recovery amount of a target mineral and a flotation separation method using the compound.

[0016] Means for solving problems

[0017] [1] A collector comprising a compound represented by the following formula (1).

[0018] [Chemical formula 3]

[0019]

[0020] (In the above formula (1), R 1 is an alkylene group having 3 to 8 carbon atoms, at least one hydrogen atom in the alkylene group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydrocarbon group having 1 to 12 carbon atoms, a hydrocarbonoxy group having 1 to 12 carbon atoms, and an acyloxy group having 6 to 12 carbon atoms, and the substituents may be bonded to each other. 2 is a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms.

[0021] [2] The collector according to [1] above, wherein R 1 It is an alkylene group having 5 or more and 6 or less carbon atoms.

[0022] [3] The collector according to [1] above, wherein the compound represented by the formula (1) is a compound represented by the following formula (4).

[0023] [Chemical formula 4]

[0024]

[0025] (In the above formula (4), R 3 An alkylene group having 3 or more and 8 or less carbon atoms, wherein at least one hydrogen atom in the alkylene group is substituted with a hydrocarbon group having 1 or more and 12 or less carbon atoms.

[0026] [4] The collector according to any one of [1] to [3] above, wherein the collector is a collector for flotation beneficiation of one or more minerals containing one or more metals selected from the group consisting of Cu, Au, Zn, Pb, Pt, Pd, Rh, Ni and Co.

[0027] [5] A flotation beneficiation method, comprising: adding a compound represented by the following formula (1) and a frother to an ore slurry, so that one or more minerals are floated in the ore slurry and recovered.

[0028] [Chemical formula 5]

[0029]

[0030] (In the above formula (1), R 1 is an alkylene group having 3 to 8 carbon atoms, at least one hydrogen atom in the alkylene group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydrocarbon group having 1 to 12 carbon atoms, a hydrocarbonoxy group having 1 to 12 carbon atoms, and an acyloxy group having 6 to 12 carbon atoms, and the substituents may be bonded to each other. 2 is a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms.

[0031] [6] The flotation beneficiation method according to [5] above, wherein the ore slurry is a slurry of an ore containing one or more minerals including one or more metals selected from the group consisting of Cu, Au, Zn, Pb, Pt, Pd, Rh, Ni and Co.

[0032] [7] The flotation beneficiation method according to [5] or [6], wherein the amount of the compound represented by the formula (1) added is 0.1 g or more and 1000 g or less per 1000 kg of the ore.

[0033] [8] The flotation beneficiation method according to any one of [5] to [7] above, wherein the pH of the ore slurry is 6 or more and 12 or less.

[0034] Effects of the Invention

[0035] According to the present disclosure, it is possible to provide a collector containing a compound that increases the recovery amount of a target mineral and a flotation separation method using the compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 This is an X-ray diffraction pattern of chalcopyrite used in Examples 1-1 to 2 and Comparative Examples 1-1 to 4.

[0037] Figure 2 This is the X-ray diffraction pattern of the copper sulfide ore used in Examples 3-1 and 2.

[0038] Figure 3 This is a schematic diagram showing a simple flotation tester (Halimond tube) used in Examples 4-1 to 4-3 and Comparative Example 4-1. DETAILED DESCRIPTION

[0039] Hereinafter, detailed description will be given based on the embodiments.

[0040] As a result of intensive research, the present inventors have found that a collector containing a cyclic thioamide compound can increase the recovery amount of a target mineral compared to conventional collectors. The present disclosure has been completed based on the above findings.

[0041] First, a collector according to an embodiment of the present disclosure will be described.

[0042] The collector of the present embodiment is a collector containing a compound represented by the following formula (1).

[0043] [Chemical formula 6]

[0044]

[0045] In the above formula (1), R 1 is an alkylene group having 3 or more and 8 or less carbon atoms. 1 In the alkylene group, at least one hydrogen atom in the alkylene group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydrocarbon group having 1 to 12 carbon atoms, a hydrocarbonoxy group having 1 to 12 carbon atoms, and an acyloxy group having 6 to 12 carbon atoms, and the substituents may be bonded to each other. 2 It is a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms.

[0046] In the cyclic thioamide compound, i.e., the compound of formula (1), R 1 In the case where a plurality of hydrogen atoms in the alkylene group are replaced by the above-mentioned substituents, the plurality of substituents may be of the same type or of different types. In addition, in the case where a plurality of hydrogen atoms in the alkylene group are replaced by the above-mentioned substituents, the plurality of substituents may also be bonded to each other.

[0047] From the perspective of increasing the recovery of minerals, R 1 The carbon number of the alkylene group is 3 or more, preferably 4 or more, and more preferably 5 or more. In addition, from the same viewpoint, R 1 The carbon number of the alkylene group is 8 or less, preferably 7 or less, and more preferably 6 or less.

[0048] From the perspective of increasing the recovery of minerals, R 2 The carbon number of the alkyl group is 3 or more, preferably 4 or more, and more preferably 6 or more. In addition, from the same viewpoint, R 2 The carbon number of the alkyl group is 16 or less, preferably 15 or less, more preferably 14 or less, and further preferably 12 or less.

[0049] Among them, from the perspective of excellent mineral recovery, the compound of formula (1) is preferably a compound represented by the following formula (2) or the following formula (3), and from the perspective of low manufacturing cost and easy manufacturing, the compound of formula (1) is preferably a compound represented by the following formula (3).

[0050] [Chemical formula 7]

[0051]

[0052] [Chemical formula 8]

[0053]

[0054] Furthermore, from the viewpoint of increasing the recovery amount of the mineral, the compound represented by formula (1) is preferably a compound represented by the following formula (4).

[0055] [Chemical formula 9]

[0056]

[0057] In the above formula (4), R 3 is an alkylene group having 3 or more and 8 or less carbon atoms. 3 In the formula (4), at least one hydrogen atom in the alkylene group is substituted with a hydrocarbon group having 1 to 12 carbon atoms. 2 Similar to the above formula (1), it is a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms.

[0058] The compound represented by the above formula (1) can increase the recovery of the target mineral, especially the recovery of multiple minerals containing multiple metals or multiple copper minerals, compared with the previous collector. Therefore, the collector containing the compound represented by the formula (1) can increase the recovery of the mineral, especially the recovery of multiple minerals containing multiple metals or multiple copper minerals. The target mineral is one or more minerals containing one or more metals selected from the group consisting of Cu, Au, Zn, Pb, Pt, Pd, Rh, Ni and Co, preferably one or more copper minerals. Such a collector of the present embodiment is suitable for flotation mineral separation.

[0059] In addition, the collector containing the compound represented by the above formula (1) is preferably a collector for flotation beneficiation of one or more minerals containing one or more metals selected from the group consisting of Cu, Au, Zn, Pb, Pt, Pd, Rh, Ni and Co, more preferably a collector for flotation beneficiation of one or more minerals containing one or more metals selected from the group consisting of Cu, Au, Zn and Pb, and further preferably a collector for flotation beneficiation of one or more copper minerals. In flotation beneficiation, the compound represented by formula (1) can particularly increase the recovery of minerals containing the above metals. Therefore, if a collector containing the compound represented by formula (1) is used for the above collector, the recovery of one or more minerals can be increased.

[0060] The form of the collector of the present embodiment can be appropriately selected according to the process of flotation beneficiation. For example, when the collector is added to the ore slurry, the collector of the present embodiment may include a frother in addition to the compound represented by formula (1). In addition, the collector of the present embodiment may also contain various additives such as inhibitors as required.

[0061] Next, a flotation separation method according to an embodiment of the present disclosure will be described.

[0062] The flotation beneficiation method of this embodiment includes: adding the compound represented by the above formula (1) and a frother to the ore slurry, so that one or more minerals are floated in the ore slurry and recovered. In addition, in the flotation beneficiation method, in addition to the compound represented by the above formula (1) and the frother, various additives such as inhibitors can be added to the ore slurry.

[0063] In the flotation beneficiation method, a compound represented by formula (1) and a frother are added to an ore slurry, and one or more minerals captured by the compound represented by formula (1) float on the liquid surface of the ore slurry together with bubbles generated by the frother. Then, by recovering the foam layer containing the mineral from the ore slurry, metals can be recovered from the ore slurry.

[0064] The ore slurry used in the flotation beneficiation method is obtained by mixing the pulverized material obtained by pulverizing the ore containing the desired mineral into a liquid such as water. In addition, the frother is a substance that dissolves in a solvent and stabilizes the bubbles of the solution. The frother can use the frother used in the flotation beneficiation in the past. As a specific substance, there is no particular limitation, and methyl isobutyl carbinol (MIBC), pine oil, Aerofroth 70 (CYTEC) and the like can be listed. The amount of the frother is preferably 0.001 g / t or more and 2000 g / t or less (0.001 g or more and 2000 g or less relative to 1000 kg of ore). If the amount of the frother is 0.001 g / t or more, it is easy to obtain floating ore. If the amount of the frother exceeds 2000 g / t, the effect of adding the frother sometimes reaches a limit. In addition, in the flotation beneficiation method, the ore slurry to which the compound represented by formula (1) and the frother are added can also be bubbled.

[0065] As described above, the compound represented by formula (1) can increase the recovery of minerals, especially the recovery of multiple minerals. Therefore, compared with the conventional collector, in the flotation beneficiation method of the present embodiment using the compound represented by formula (1), since a large amount of minerals can be floated on the liquid surface of the ore slurry, the recovery of the minerals recovered from the ore slurry can be increased.

[0066] Furthermore, in the flotation beneficiation method of the present embodiment, the ore slurry is preferably a slurry of an ore containing one or more minerals containing one or more metals selected from the group consisting of Cu, Au, Zn, Pb, Pt, Pd, Rh, Ni and Co, more preferably a slurry of an ore containing one or more minerals containing one or more metals selected from the group consisting of Cu, Au, Zn and Pb, and further preferably a slurry of an ore containing one or more copper minerals.

[0067] As described above, the compound represented by formula (1) can particularly increase the recovery of minerals containing the above-mentioned metals. Therefore, in the flotation beneficiation method of the present embodiment, if flotation beneficiation is performed on one or more minerals containing the above-mentioned one or more metals, the recovery of the above-mentioned one or more minerals can be increased.

[0068] In addition, in the flotation beneficiation method, the addition amount of the compound represented by formula (1) is preferably 0.1 g or more and 1000 g or less, more preferably 10 g or more and 300 g or less, and further preferably 50 g or more and 300 g or less, relative to 1000 kg of ore. If the above-mentioned addition amount of the compound represented by formula (1) is 0.1 g or more, the recovery amount of the target mineral can be fully increased. If the above-mentioned addition amount of the compound represented by formula (1) is 1000 g or less, the cost of the compound represented by formula (1) can be reduced.

[0069] In the flotation beneficiation method, the pH of the ore slurry is preferably 6 to 12, and more preferably 8 to 12. When the pH of the ore slurry is within the above range, the amount of recovered minerals can be further increased.

[0070] According to the above-described embodiment, the recovery amount of the target mineral can be increased by using a collector containing the compound represented by formula (1). Therefore, in flotation separation, the recovery amount of the desired mineral can be increased.

[0071] Example

[0072] Next, examples and comparative examples will be described, but the present disclosure is not limited to these examples.

[0073] (Example 1-1)

[0074] As shown in Table 1, flotation separation of chalcopyrite was carried out using the compound represented by formula (2) (manufactured by Tokyo Chemical Industry Co., Ltd.).

[0075] [Chemical formula 10]

[0076]

[0077] Flotation separation is carried out in the following steps. First, the Figure 1 The slurry of the crushed chalcopyrite with the X-ray diffraction pattern shown in is adjusted to pH 9 with sodium hydroxide, and 100 g of the compound represented by formula (2) and 200 g of a foaming agent (methyl isobutyl carbinol (MIBC)) are added to every 1000 kg of chalcopyrite. The Cu grade of the chalcopyrite used is 30.2%, and the Fe grade is 28.8%. The amount of crushed chalcopyrite in the slurry is set to 100 g, and the amount of water is set to 800 mL. Then, an Aquitaine flotation machine (made by KAMATAGIKEN, cylindrical Aquitaine flotation machine AGR-1L) is used to perform flotation separation for 10 minutes at a rotation speed of 2000 rpm to obtain flotation and tailings. The Cu grade of the obtained flotation and tailings is measured, and the recovery rate of Cu is calculated based on the following formula (A). The so-called flotation refers to the ore that floats in the flotation separation, and the so-called tailing refers to the ore that does not float in the flotation separation. Similarly, the Fe grades of the obtained flotation ore and tailings were measured, and the Fe recovery rate was calculated.

[0078] Formula (A): Cu recovery rate (%) = float weight (g) × float Cu grade (%) × 100 / (float weight (g) × float Cu grade (%) + tailings weight (g) × tailings Cu grade (%))

[0079] (Example 1-2)

[0080] Flotation separation of chalcopyrite was carried out in the same manner as in Example 1-1, except that the compound represented by formula (3) was used instead of the compound represented by formula (2).

[0081] The compound represented by formula (3) was synthesized as follows. First, under a nitrogen stream, 1.9 g (15 mmol) of ω-enantholactam (manufactured by Tokyo Chemical Industry Co., Ltd.) and 25 mL of toluene were added to a three-necked flask (200 mL). Then, 3.0 g (7.5 mmol) of Lawesson's reagent was added and stirred at 80° C. for 3 hours. The reaction solution was concentrated to obtain a crude product as a yellow solid. The crude product was purified by silica gel column chromatography to obtain 1.1 g (yield 50%) of the compound represented by formula (3) as a white solid.

[0082] [Chemical formula 11]

[0083]

[0084] (Comparative Example 1-1)

[0085] Flotation separation of chalcopyrite was carried out in the same manner as in Example 1-1 except that PAX (Cytec Industries, Potassium Amyl Xanthate) was used instead of the compound represented by formula (2).

[0086] (Comparative Example 1-2)

[0087] Flotation concentration of chalcopyrite was carried out in the same manner as in Example 1-1 except that the compound represented by formula (10) (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of the compound represented by formula (2).

[0088] [Chemical formula 12]

[0089]

[0090] (Comparative Examples 1-3)

[0091] Flotation concentration of chalcopyrite was carried out in the same manner as in Example 1-1 except that the compound represented by formula (11) was used instead of the compound represented by formula (2).

[0092] The compound represented by formula (11) was synthesized as follows. First, under a nitrogen gas stream, 3.0 g (30 mmol) of N-ethylpropionamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 300 mL of toluene were added to a four-necked flask (500 mL), followed by the addition of 12.0 g (30 mmol) of Lawesson's reagent and refluxed at 120° C. for 30 minutes. After stirring the reaction solution in an ice-water bath for 1 hour, the precipitate was filtered and removed. The filtrate was concentrated to obtain 2.4 g of a crude product as a mixture of a yellow oil and a white solid. The crude product was refined by silica gel column chromatography to obtain 1.1 g (yield 31%) of the compound represented by formula (11) as a colorless oil.

[0093] [Chemical formula 13]

[0094]

[0095] (Comparative Examples 1-4)

[0096] Flotation concentration of chalcopyrite was carried out in the same manner as in Example 1-1 except that the compound represented by formula (12) (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of the compound represented by formula (2).

[0097] [Chemical formula 14]

[0098]

[0099] Table 1

[0100]

[0101] As shown in Table 1, in Examples 1-1 and 2, the recovery rate of Cu increased compared with Comparative Examples 1-1 to 4.

[0102] (Examples 2-1 to 2 and Comparative Example 2-1)

[0103] As shown in Table 2, flotation separation was carried out in the same manner as in Examples 1-1 to 2 or Comparative Example 2-1 except that 50 g of each compound was added per 1000 kg of chalcopyrite.

[0104] Table 2

[0105]

[0106] As shown in Table 2, in Examples 2-1 to 2, the recovery rate of Cu increased compared to Comparative Example 2-1.

[0107] (Example 3-1)

[0108] As shown in Table 3, flotation beneficiation of copper sulfide ore was carried out using the compound of formula (2) used in Example 1-1.

[0109] Flotation separation is carried out in the following steps. First, the Figure 2 The slurry of the crushed copper sulfide ore having the X-ray diffraction pattern shown in is adjusted to pH 9 with sodium hydroxide, and 100 g of the compound represented by formula (2) and 200 g of a foaming agent (methyl isobutyl carbinol (MIBC)) are added to every 1000 kg of ore. The Cu grade of the ore used is 1.5%, and the Fe grade is 3.4%. The amount of crushed ore in the slurry is set to 100 g, and the amount of water is set to 800 mL. Then, an Aquitaine flotation machine (made by KAMATAGIKEN, cylindrical Aquitaine flotation machine AGR-1L) is used to perform flotation separation at a rotation speed of 2000 rpm for 10 minutes to obtain flotation ore and tailings. The Cu grade of the obtained flotation ore and tailings is measured, and the recovery rate of Cu is calculated. In addition, the Fe grade of the obtained flotation ore and tailings is measured in the same manner, and the recovery rate of Fe is calculated.

[0110] (Example 3-2)

[0111] Flotation beneficiation of copper sulfide ore was carried out in the same manner as in Example 3-1 except that the compound represented by formula (3) was used instead of the compound represented by formula (2). The compound represented by formula (3) was synthesized in the same manner as in Example 1-2.

[0112] Table 3

[0113]

[0114] As shown in Table 3, the recovery rate of Cu was also good in the flotation concentration of the copper sulfide ore.

[0115] (Example 4-1)

[0116] As shown in Table 4, flotation separation of chalcopyrite was carried out using the compound represented by formula (2).

[0117] Flotation separation is carried out by the following steps. First, 100 g of the compound represented by formula (2) and 200 g of a foaming agent (methyl isobutyl carbinol (MIBC)) are added to a slurry of chalcopyrite crushed to a particle size of 75 μm or less per 1000 kg of chalcopyrite to prepare the slurry. The Cu grade of the chalcopyrite used is 30.5%. The amount of chalcopyrite crushed in the slurry is set to 5 g, and the amount of water is set to 100 mL. Then, the slurry is put into Figure 3 In the simple flotation test machine 1 (Halmond tube) shown in FIG.

[0118] Next, nitrogen 20 is introduced into the slurry 10 through the plug 4 from the bottom of the tube 2 constituting the simple flotation test machine 1 to generate bubbles 11, and separation is performed by flotation treatment. Specifically, most of the particles of the arsenic-containing copper mineral, which are highly hydrophobic particles 12, adhere to the bubbles 11 and float up, and the floating bubbles 11 burst at the top, settle in the tube 3 connected to the tube 2 and accumulate (floating ore A, scum). On the other hand, the particles that are not attached to the bubbles 11 are retained in the tube 2 (tailings B, residues).

[0119] Then, flotation concentration was performed for 10 minutes to obtain flotation ore and tailings. The Cu grades of the obtained flotation ore and tailings were measured, and the recovery rate of Cu was calculated based on the above formula (A).

[0120] (Example 4-2)

[0121] Flotation separation of chalcopyrite was carried out in the same manner as in Example 4-1, except that the compound represented by formula (13) was used instead of the compound represented by formula (2).

[0122] [Chemical formula 15]

[0123]

[0124] (Example 4-3)

[0125] Flotation separation of chalcopyrite was carried out in the same manner as in Example 4-1 except that the compound represented by formula (14) was used instead of the compound represented by formula (2).

[0126] [Chemical formula 16]

[0127]

[0128] (Comparative Example 4-1)

[0129] Flotation concentration of chalcopyrite was carried out in the same manner as in Example 4-1 except that PAX was used instead of the compound represented by formula (2).

[0130] Table 4

[0131]

[0132] As shown in Table 4, in Examples 4-1 to 4-3, the recovery rate of Cu increased compared with Comparative Example 4-1.

[0133] Explanation of symbols

[0134] 1 Simple flotation test machine

[0135] 2.3 Tube

[0136] 4. Stopper

[0137] 10 Slurry

[0138] 11 Bubbles

[0139] 12 Highly hydrophobic particles

[0140] 20 Nitrogen or air

[0141] A Float

[0142] B Tailings

Claims

1. A collector comprising a compound represented by the following formula (1): In the formula (1), R 1 is an alkylene group having 3 to 8 carbon atoms, at least one hydrogen atom in the alkylene group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydrocarbon group having 1 to 12 carbon atoms, a hydrocarbonoxy group having 1 to 12 carbon atoms, and an acyloxy group having 6 to 12 carbon atoms, and the substituents may be bonded to each other, R 2 It is a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms.

2. The collector according to claim 1, wherein R 1 It is an alkylene group having 5 or more and 6 or less carbon atoms.

3. The collector according to claim 1, wherein The compound represented by the formula (1) is a compound represented by the following formula (4), In the formula (4), R 3 An alkylene group having 3 to 8 carbon atoms, in which at least one hydrogen atom is substituted with a hydrocarbon group having 1 to 12 carbon atoms.

4. The collector according to any one of claims 1 to 3, wherein The collector is a collector for flotation beneficiation of one or more minerals containing one or more metals selected from the group consisting of Cu, Au, Zn, Pb, Pt, Pd, Rh, Ni and Co.

5. A flotation beneficiation method, comprising: A compound represented by the following formula (1) and a foaming agent are added to an ore slurry to float one or more minerals in the ore slurry and recover them. In the formula (1), R 1 is an alkylene group having 3 to 8 carbon atoms, at least one hydrogen atom in the alkylene group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydrocarbon group having 1 to 12 carbon atoms, a hydrocarbonoxy group having 1 to 12 carbon atoms, and an acyloxy group having 6 to 12 carbon atoms, and the substituents may be bonded to each other, R 2 It is a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms.

6. The flotation beneficiation method according to claim 5, wherein: The ore slurry is a slurry of an ore containing one or more minerals including one or more metals selected from the group consisting of Cu, Au, Zn, Pb, Pt, Pd, Rh, Ni, and Co.

7. The flotation beneficiation method according to claim 5 or 6, wherein: The amount of the compound represented by the formula (1) added is 0.1 g or more and 1000 g or less per 1000 kg of the ore.

8. The flotation beneficiation method according to claim 5 or 6, wherein: The pH of the ore slurry is 6 or more and 12 or less.

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