# US 2021/0276023 A1 · Alkyl thioether ethyl hydroxamic acid beneficiation reagent and preparation method and application thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2021/0276023 A1 - Document ID: US20210276023A1 - Status: Published application - Kind: A1 - Application number: 15/734,226 - Filed: 2020-06-19 - Published: 2021-09-09 - Earliest claimed: 2019-09-04 - Assignees: Central South University - Applicants: Central South University - Inventors: Hong ZHONG; Qing SUN; Shuai WANG - Web page: https://patentgrep.com/patent/US20210276023A1 ## CPC - B03D 1/012: containing sulfur - B03D 1/008: containing oxygen - B03D 1/01: containing nitrogen - C07C 323/60: with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms - B03D 2201/02: Collectors - B03D 2203/02: Ores - B03D 2203/04: Non-sulfide ores - B03D: FLOTATION; DIFFERENTIAL SEDIMENTATION (sedimentation in general B01D21/00; in combination with other separation of solids B03B; sink-float separation B03B5/28; detergents, soaps C11D) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract An alkyl thioether ethyl hydroxamic acid beneficiation reagent and a preparation method and application thereof are provided. The alkyl thioether ethyl hydroxamic acid molecules have two functional groups, a thioether group and a hydroxamate group. The beneficiation reagent is obtained by esterification of alkyl thioether acetic acid and methanol and then by hydroxamation of hydroxylamine and an alkali. The alkyl thioether ethyl hydroxamic acid beneficiation reagent can be used as a collector for mineral flotation. The preparation method is simple and has a high yield. The thioether and hydroxamate group in the molecules have a synergistic effect and can effectively improve the collection performance. ## Claims ### Claim 1 An alkyl thioether ethyl hydroxamic acid beneficiation reagent, wherein the alkyl thioether ethyl hydroxamic acid beneficiation reagent has a structure as shown in formula I, wherein in the formula I, R1 is one selected from the group consisting of a C1-C12 alkane group, a C5-C12 cycloalkyl group, a C6-C12 aromatic group and a C1-C12 alkane group and the C1-C12 alkane group is substituted with at least one substituent. ### Claim 2 (depends on 1) The alkyl thioether ethyl hydroxamic acid beneficiation reagent according to claim 1, wherein R1 is one selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, isohexyl, sec-hexyl, cyclohexyl, heptyl, cycloheptyl, n-octyl, isooctyl, sec-octyl, cyclooctyl, benzyl, phenyl, p-tert-butyl benzyl and dodecyl. ### Claim 3 (depends on 2) The alkyl thioether ethyl hydroxamic acid beneficiation reagent according to claim 2, wherein R1 is the benzyl or the dodecyl. ### Claim 4 (depends on 1) A preparation method of the alkyl thioether ethyl hydroxamic acid beneficiation reagent according to claim 1, comprising the following steps: (1) an esterification reaction: subjecting an alkyl thioether acetic acid with a structure as shown in formula II and methanol to the esterification reaction under a catalysis of a concentrated sulfuric acid to obtain a methyl alkyl thioether acetate with a structure as shown in formula III; (2) a hydroxamation reaction: subjecting the methyl alkyl thioether acetate with the structure as shown in the formula III, a hydroxylamine and an alkali to the hydroxamation reaction in an aqueous solution to obtain the alkyl thioether ethyl hydroxamic acid beneficiation reagent, ### Claim 5 (depends on 4) The preparation method according to claim 4, wherein in step (1), a temperature of the esterification reaction is 50-100° C., a reaction time is 1-6 hours, a molar ratio of the alkyl thioether acetic acid to the methanol is 1:(1-8), a mass fraction of the concentrated sulfuric acid is 25-50 g/mol, and an added amount of the concentrated sulfuric acid is 2.5-5 g/0.1 mol of the alkyl thioether acetic acid. ### Claim 6 (depends on 4) The preparation method according to claim 4, wherein in step (2), a temperature of the hydroxamation reaction is 10-60° C., a reaction time is 2.5-6 hours, the hydroxylamine is hydroxylamine hydrochloride or hydroxylamine sulfate, the alkali is sodium hydroxide or potassium hydroxide, a molar ratio of the methyl alkyl thioether acetate to the hydroxylamine to the alkali is 1:(1-1.5):(1-1.5), and an amount of water in the aqueous solution is 10-100 mL water/0.1 mol of the methyl alkyl thioether acetate. ### Claim 7 (depends on 1) A method of collecting a flotation of metallic ores, comprising: using the alkyl thioether ethyl hydroxamic acid beneficiation reagent according to claim 1 as a collector for the flotation of the metallic ores. ### Claim 8 (depends on 7) The method according to claim 7, wherein the metallic ores are at least one selected from the group consisting of bauxite, tungsten ores, copper oxide ores and tin ores. ### Claim 9 (depends on 7) The method according to claim 7, wherein a basic process of using the alkyl thioether ethyl hydroxamic acid beneficiation reagent as the collector comprises: (1) floating the metallic ores after grinding to achieve the flotation of the metallic ores; (2) preparing a saline solution of the alkyl thioether ethyl hydroxamic acid as a flotation reagent by mixing the alkyl thioether ethyl hydroxamic acid beneficiation reagent and sodium hydroxide or potassium hydroxide in water; (3) adding hydrochloric acid or the sodium hydroxide during the floating to adjust a pulp pH to 7-9, and adding the saline solution of the alkyl thioether ethyl hydroxamic acid to the flotation of the metallic ores under weakly alkaline conditions to reach a concentration of 25-400 mg/L; and (4) floating useful metallic minerals by a froth flotation method. ### Claim 10 (depends on 4) The preparation method according to claim 4, wherein R1 is one selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, isohexyl, sec-hexyl, cyclohexyl, heptyl, cycloheptyl, n-octyl, isooctyl, sec-octyl, cyclooctyl, benzyl, phenyl, p-tert-butyl benzyl and dodecyl. ### Claim 11 (depends on 10) The preparation method according to claim 10, wherein R1 is the benzyl or the dodecyl. ### Claim 12 (depends on 7) The method according to claim 7, wherein R1 is one selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, isohexyl, sec-hexyl, cyclohexyl, heptyl, cycloheptyl, n-octyl, isooctyl, sec-octyl, cyclooctyl, benzyl, phenyl, p-tert-butyl benzyl and dodecyl. ### Claim 13 (depends on 12) The method according to claim 12, wherein R1 is the benzyl or the dodecyl. ### Claim 14 (depends on 8) The method according to claim 8, wherein a basic process of using the alkyl thioether ethyl hydroxamic acid beneficiation reagent as the collector comprises: (1) floating the metallic ores after grinding to achieve the flotation of the metallic ores: (2) preparing a saline solution of the alkyl thioether ethyl hydroxamic acid as a flotation reagent by mixing the alkyl thioether ethyl hydroxamic acid beneficiation reagent and sodium hydroxide or potassium hydroxide in water; (3) adding hydrochloric acid or the sodium hydroxide during the floating to adjust a pulp pH to 7-9, and adding the saline solution of the alkyl thioether ethyl hydroxamic acid to the flotation of the metallic ores under weakly alkaline conditions to reach a concentration of 25-400 mg/L; and (4) floating useful metallic minerals by a froth flotation method.