CN103301952B - 6-aliphatic hydrocarbon amido hexyl hydroximic acid collecting agent and preparation and application methods thereof - Google Patents

6-aliphatic hydrocarbon amido hexyl hydroximic acid collecting agent and preparation and application methods thereof Download PDF

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CN103301952B
CN103301952B CN201310244128.8A CN201310244128A CN103301952B CN 103301952 B CN103301952 B CN 103301952B CN 201310244128 A CN201310244128 A CN 201310244128A CN 103301952 B CN103301952 B CN 103301952B
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acid
hydroximic acid
amide groups
hexyl hydroximic
aliphatic group
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CN103301952A (en
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钟宏
邓兰青
王帅
黄志强
刘广义
曹占芳
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Central South University
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Abstract

A structural formula of a 6-aliphatic hydrocarbon amido hexyl hydroximic acid collecting agent is represented by a formula (I), wherein R represents C2-C18 aliphatic hydrocarbon group. The preparation method comprises the steps as follows: caprolactam and hydroxylamine hydrochloride or hydroxylamine sulphate are taken as raw materials, methylbenzene is taken as a solvent, the reaction temperature ranges from 80 DEG C to 110 DEG C, the reaction lasts for 1-4 hours, and 6-amino hexyl hydroximic acid is generated; 6-amino hexyl hydroximic acid reacts with C2-C18 fat carboxylic acid at the reaction temperature ranging from 100 DEG C to 160 DEG C for 1-4 hours to generate 6-aliphatic hydrocarbon amido hexyl hydroximic acid, and the product yield can be higher than 91%; and 6-aliphatic hydrocarbon amido hexyl hydroximic acid used in flotation of scheelite, wolframite, tombarthite ore, tin ore, bauxite, titanic iron ore or fluorite ore is taken as the collecting agent, so that the flotation recovery rate can be increased by 3%-10%.

Description

6-aliphatic group amide groups hexyl hydroximic acid collecting agent and methods for making and using same thereof
Technical field
The present invention relates to 6-aliphatic group amide groups hexyl hydroximic acid and in scheelite, wolframite, Rare Earth Mine, tin ore, bauxite, ilmenite or fluorite flotation, be used as method and the preparation method of collecting agent.
Background technology
Hydroximic acid and salt thereof are the known flotation collectors for oxide mineral froth flotation method, be usually used in the flotation of metal or mineral, as fluorite, huebnerite, wolframite, cassiterite, muscovite, phosphorite, bloodstone, pyrolusite, rhodonite, chrysocolla, malachite, barite, calcite and rare earth.Hydroximic acid is conventionally more powerful and more selective than conventional aliphatic acid, aliphatic amine, petroleum sulfonate and alkyl sulfate.
At present, the hydroximic acid collecting agent for mineral floating mainly contains fatty hydroximic acid collecting agent and benzene first hydroximic acid collecting agent.Patent CN101816980A discloses a kind of C 5~9alkyl hydroximic acid (see structural formula a), this kind of hydroximic acid and Fatty acids composition are as the flotation collector of Rare Earth Mine.Patent CN1533305A discloses C 6~14aliphatic hydroximic acid.Patent CN1303444A discloses C 6~22the mixture of aliphatic hydroximic acid and oleic acid is made flotation collector, for froth flotation method, from mineral ore deposit, removes impurity.Patent CN101519365A discloses a kind of improvement production method (seeing structural formula b) of Using Salicyl Hydroximic Acid.Patent CN102584629A discloses a kind of preparation method of propylene hydroximic acid.Gao Yude etc. have reported that the research of benzene first hydroximic acid collecting floatation of tungsten mineral solution (is shown in structural formula c, Gao Yude etc., non-ferrous metal (ore dressing part), 2003 (4): 28-31.).Patent CN102302983A discloses quaternary ammonium salt hydroximic acid flotation collector and preparation method's (seeing structural formula d), and quaternary ammonium salt hydroximic acid is strong to calcium, magnesium sequestering power.Use alkyl hydroximic acid and benzene first hydroximic acid compound can improve the rate of recovery of noble metal as collecting agent, but the group of above-mentioned hydroximic acid collecting metal ion is only from hydroximic acid functional group, and along with the carbon chain growth of hydroximic acid, water-soluble variation, has affected the flotation performance of collecting agent.At present, the hydroximic acid of realizing commercial Application is mainly octyl group hydroximic acid, C 7~9the hydroximic acid of the short hydrocarbon chain structures such as alkyl hydroximic acid, benzene first hydroximic acid, Using Salicyl Hydroximic Acid, it is selectively good, but a little less than collecting ability, has limited collecting agent flotation performance and application.Above-mentioned collecting agent generally adopts the method preparations such as azanol-carboxylate method, azanol-chloride method, and hydroximic acid product needed is separated through persalt or sulfuric acid acidation, and the organic acidity waste water producing has not only caused product loss, has also brought serious problem of environmental pollution.
(structural formula a: fatty hydroximic acid)
(structural formula b: Using Salicyl Hydroximic Acid)
(structural formula c: benzene first hydroximic acid)
(structural formula d: quaternary ammonium salt hydroximic acid)
At present; relevant molecule contains the hydroximic acid research of substituted amido; only limit to this compounds and have the biologically active of inhibition of histone deacetylase, and this inhibition activity being a kind of mode of effective treatment cancer, is also to study now class I histone deacetylase (HDAC) inhibitor comparatively widely (to see structural formula e; Andrianov V; Gailite V, Lola D, Loza E; et al.Europ.Med.Chem.2009,44:1067-1085).The preparation method that the molecule of Andrianov V report contains the hydroximic acid of hydrocarbon amide groups is: the acyl chlorides that contains phenyl ring and H 2n (CH) ncOOMe(n=4~7) reaction, after the intermediate piptonychia ester hydroxyl oximate of generation, obtains product (structural formula e).The shortcoming of this method is: the toxicity of acyl chlorides is large, easily hydrolysis, and hydroxyl oximation reaction need react under the condition of heating and highly basic, easily causes the fracture of amido link in molecule, and product yield is lower.
(structural formula e, n1=1,2,3, n=4,5,6,7)
Summary of the invention
The object of the invention is that defect for existing collecting agent and synthetic method has proposed using 6-aliphatic group amide groups hexyl hydroximic acid as collectors application in scheelite, wolframite, Rare Earth Mine, tin ore, bauxite, ilmenite or fluorite flotation, and 6-aliphatic group amide groups hexyl hydroximic acid of a kind of efficient, environmental protection and preparation method thereof has been proposed.At present, 6-aliphatic group amide groups hexyl hydroximic acid has no report as flotation collector in flotation, does not also see the defined 6-aliphatic group of the present invention amide groups hexyl hydroximic acid and synthetic method thereof.
A 6-aliphatic group amide groups hexyl hydroximic acid, specifically suc as formula shown in (I) structure.
Wherein R represents the aliphatic group of C2~C18.
The application process of described 6-aliphatic group amide groups hexyl hydroximic acid, the collecting agent using the 6-aliphatic group amide groups hexyl hydroximic acid of structure shown in formula (I) as scheelite, wolframite, Rare Earth Mine, tin ore, bauxite, ilmenite or fluorite flotation.
The basic operation procedure that 6-aliphatic group amide groups hexyl hydroximic acid is made collecting agent is: (a) after grinde ore, enter flotation; (b) aqueous solution that 6-aliphatic group amide groups hexyl hydroximic acid and NaOH, potassium hydroxide or ammoniacal liquor is made in water to 6-aliphatic group amide groups hexyl hydroximic acid salt is as floating agent; (c) in ore grinding and/or floatation process, add floating agent to size mixing, ilmenite regulates pH4~7 with sulfuric acid, other is mining, and sodium carbonate regulates pH7~12 scope, the aqueous solution that at least contains 6-aliphatic group amide groups hexyl hydroximic acid salt in the medicament adding, the amount ranges 40~1500g/t of 6-aliphatic group amide groups hexyl hydroximic acid; (d) by froth flotation method emersion useful metal mineral.
The preparation method of described 6-aliphatic group amide groups hexyl hydroximic acid, comprise the following steps: (1) take caprolactam and hydroxylamine hydrochloride or HAS as raw material, the amide groups of two kinds of raw materials: azanol base mol ratio=1:1, toluene is solvent, 80~110 ℃ of reaction temperatures, react 1~4 hour, generate the amino hexyl hydroximic acid of 6-suc as formula structure shown in (II); (2) the amino hexyl hydroximic acid of 6-and C 2~C 18aliphatic carboxylic acid reaction, the amino of two kinds of reactants: carboxyl mol ratio=1:1~1.3, reaction temperature is 100~160 ℃, reacts 1~4 hour, generates the 6-aliphatic group amide groups hexyl hydroximic acid with structure shown in formula (I).
Described C 2~C 18aliphatic carboxylic acid comprises C 2~C 18alkyl carboxylic acid and containing one or more in the unsaturated alkyl carboxylic acid of alkenyl or alkynyl.Preferably include one or more in acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, sad, isooctyl acid, capric acid, oleic acid, linoleic acid, leukotrienes, octenoic acid, decylenic acid, lauroleic acid, laurate, cyclohexanecarboxylic acid, or a kind of in cocinic acid, palmitoleic acid, aphthenic acids.
Described C 2~C 18aliphatic carboxylic acid preferably includes one or more in caproic acid, sad, isooctyl acid, capric acid, oleic acid, linoleic acid, leukotrienes, octenoic acid, decylenic acid, lauroleic acid, laurate, cyclohexanecarboxylic acid, or a kind of in cocinic acid, palmitoleic acid, aphthenic acids.
In said method, solvent load is quality of caprolactam 2~5 times, reaction finishes rear solvent distillation and recycles.
While carrying out hydroxyl oximate with hydroxylamine hydrochloride, the hydrochloric acid producing in course of reaction passes in the aqueous solution or sodium hydrate aqueous solution and absorbs, and adds after completion of the reaction in sodium carbonate with complete; While carrying out hydroxyl oximate with HAS, the sulfuric acid that adds after completion of the reaction sodium carbonate neutralization reaction to produce.
6-aliphatic group amide groups hexyl hydroximic acid collecting agent used in the present invention, the mineral such as scheelite, wolframite, Rare Earth Mine, tin ore, bauxite, ilmenite or fluorite ore are had to strong collecting ability, can improve the flotation recovery rate of scheelite, wolframite, Rare Earth Mine, tin ore, bauxite, ilmenite or fluorite mineral.Adopt 6-aliphatic group amide groups hexyl hydroximic acid compound of the present invention as flotation collector or with other collecting agents such as oleic acid, to combine use separately, 6-aliphatic group amide groups hexyl hydroximic acid consumption 40~1500g/t, in ore grinding and/or floatation process, add floating agent to size mixing, ilmenite regulates pH4~7 with sulfuric acid, remaining oxide ore regulates pH7~12 with sodium carbonate, compare with benzene first hydroximic acid, can make the flotation recovery rate of oxide ore improve, realize the high FLOTATION SEPARATION of valuable mineral and gangue mineral, improve 3~10 percentage points of flotation recovery rates.
The advantage of 6-aliphatic group amide groups hexyl hydroximic acid collecting agent of the present invention is:
(1) 6-aliphatic group amide groups hexyl hydroximic acid molecule has hydroxyl oximido and two close mineral groups of amide groups, stronger with the chelation ability of metallic element, selective better to target mineral.
(2) by suitably increasing the length of hydrophobic group 6-aliphatic group carbochain, can improve the hydrophobic foamability of collecting agent, improve froth flotation efficiency.
(3) amide groups of 6-aliphatic group amide groups hexyl hydroximic acid is hydrophilic group, while suitably increasing hydrophobic group length, collecting agent still can keep certain water-soluble, overcome the long indissoluble solution of common hydroximic acid hydrophobic group, the weak shortcoming of the short collecting ability of hydrophobic group, realized the flotation applications of long carbochain hydroximic acid.
The preparation method's of 6-aliphatic group amide groups hexyl hydroximic acid of the present invention advantage is:
(1) hydroxyl oximation reaction need to not carry out under highly basic condition, has avoided causing under heating and highly basic condition the problem of amide groups fracture, prepares conventional method and is difficult to synthetic amide groups hydroximic acid collecting agent;
(2) preparation process is easy, efficient, and product purity can reach more than 89%, and yield can reach more than 91%;
(3) reaction dissolvent can be reused, and does not need acidifying after reaction, non-wastewater discharge, production process environmental protection.
Accompanying drawing explanation
Fig. 1 is the mass spectrogram of the positive caprinoyl amido of 6-hexyl hydroximic acid;
Fig. 2 is the mass spectrogram of the positive decoyl amido of 6-hexyl hydroximic acid;
Fig. 3 is the mass spectrogram of 6-valnoctamide base hexyl hydroximic acid;
Fig. 4 is the mass spectrogram of 6-hexadecanoyl amido hexyl hydroximic acid;
Fig. 5 is the H-NMR figure of the positive caprinoyl amido of 6-hexyl hydroximic acid;
Fig. 6 is the H-NMR figure of the positive decoyl amido of 6-hexyl hydroximic acid;
Fig. 7 is the H-NMR figure of 6-valnoctamide base hexyl hydroximic acid;
Fig. 8 is the infrared spectrum of the positive caprinoyl amido of 6-hexyl hydroximic acid;
Fig. 9 is the infrared spectrum of the positive decoyl amido of 6-hexyl hydroximic acid;
Figure 10 is the infrared spectrum of 6-(9-octadecylene) amide groups hexyl hydroximic acid;
Figure 11 is the infrared spectrum of 6-dodecanoyl amido hexyl hydroximic acid;
Figure 12 is the infrared spectrum of 6-hexadecanoyl amido hexyl hydroximic acid;
The specific embodiment
The present invention is further illustrated by the following example, but is not subject to the restriction of these embodiment.In embodiment, unless otherwise specified all umbers and percentage all refer to quality.
The preparation of the positive caprinoyl amido of embodiment 1:6-hexyl hydroximic acid
The caprolactam that is 99% by 11.32 parts of purity and 6.95 parts of purity are that 99% hydroxylamine hydrochloride adds in reactor, add 34.64 parts of toluene to make solvent, are under agitation heated to 105 ℃, react after 3 hours, and distilling off solvent reclaims; And then 17.26 parts of n-capric acids are added in above-mentioned reactor, be under agitation heated to 120 ℃, react 1~4 hour, obtain the positive caprinoyl amido of needed 6-hexyl hydroximic acid product.Analysis shows that the positive caprinoyl amido of 6-hexyl hydroximic acid purity is 90.3%, and yield is 92.4%.Product Mr:300.24, through Mass Spectrometer Method MS:286.15[M-15] (see figure 1), for falling the peak of methyl.Nuclear magnetic resonance spectroscopy and infrared spectrum analysis collection of illustrative plates are shown in respectively Fig. 5 and Fig. 8, and data are in Table 1 and table 2.
The preparation of the positive decoyl amido of embodiment 2:6-hexyl hydroximic acid
Change 17.26 parts of n-capric acids in embodiment 1 into 14.42 parts of caprylic acids, other condition is constant, and the purity of the positive decoyl amido of the 6-hexyl hydroximic acid obtaining is 91.4%, and yield is 93.2%.Product Mr:272.21, through Mass Spectrometer Method MS:258.10[M-15] (seeing Fig. 2), for falling the peak of methyl.Nuclear magnetic resonance spectroscopy and infrared spectrum analysis collection of illustrative plates are shown in respectively Fig. 6 and Fig. 9, and data are in Table 1 and table 2.
The preparation of embodiment 3:6-valnoctamide base hexyl hydroximic acid
Change 17.26 parts of n-capric acids in embodiment 1 into 14.42 parts of isooctyl acids, other condition is constant, and the purity of the 6-valnoctamide base hexyl hydroximic acid obtaining is 89.4%, and yield is 91.2%.Product Mr:272.21, through Mass Spectrometer Method MS:244.15[M-29] (seeing Fig. 3), for falling the peak of side chain ethyl; 258.05[M-15], for falling the peak of methyl.Fig. 7 is shown in by nuclear magnetic resonance spectroscopy collection of illustrative plates, and data are in Table 2.
The preparation of embodiment 4:6-(9-vaccenic acid) amide groups hexyl hydroximic acid
Change 17.26 parts of n-capric acids in embodiment 1 into 28.25 parts of 9-octadecenoic acids, other condition is constant, and the purity of the 9-vaccenic acid hexyl hydroximic acid obtaining is 90.7%, and yield is 92.1%.Figure 10 is shown in by infrared spectrum analysis collection of illustrative plates, and data are in Table 1.
The preparation of embodiment 5:6-dodecanoyl amido hexyl hydroximic acid
Change 17.26 parts of n-capric acids in embodiment 1 into 20.03 parts of dodecylic acids, other condition is constant, and the purity of the 6-dodecanoyl amido hexyl hydroximic acid obtaining is 90.4%, and yield is 92.8%.Figure 11 is shown in by infrared spectrum analysis collection of illustrative plates, and data are in Table 1.
The preparation of embodiment 6:6-hexadecanoyl amido hexyl hydroximic acid
Change 17.26 parts of n-capric acids in embodiment 1 into 25.64 parts of hexadecanoic acids, other condition is constant, and the purity of the 6-hexadecanoyl amido hexyl hydroximic acid obtaining is 91.4%, and yield is 93.3%.Product Mr:384.21, through Mass Spectrometer Method MS:384.25 (being shown in Fig. 4).Figure 12 is shown in by infrared spectrum analysis collection of illustrative plates, and data are in Table 1.
Five kinds of 6-aliphatic group amide groups hexyl infrared parsing summary tables of hydroximic acid of table 1 (seeing Fig. 8~12)
Three kinds of 6-aliphatic group amide groups hexyl hydroximic acid hydrogen spectrum nuclear-magnetisms of table 2 are resolved summary table (seeing Fig. 5~7)
Below in the embodiment of application, " the 6-aliphatic group amide groups hexyl hydroximic acid " mentioned is all that 6-aliphatic group amide groups hexyl hydroximic acid and NaOH, potassium hydroxide or ammoniacal liquor are made into the floating agent that the aqueous solution of 6-aliphatic group amide groups hexyl hydroximic acid salt is used as in water.
The application of the positive caprinoyl amido of embodiment 7:6-hexyl hydroximic acid in tungsten ore flotation
Certain selects sulphur mine tailing containing WO 30.24%, mog-200 order accounts for 85%, adopts the sodium carbonate adjust pH of 3000g/t, and the waterglass of 2500g/t is dispersant, through one roughing operation, obtains tungsten rough concentrate, to the flotation results of the positive caprinoyl amido of 6-hexyl hydroximic acid and benzene first hydroximic acid in Table 3.Result shows, the positive caprinoyl amido of 6-hexyl hydroximic acid and oxidized paraffin wax soap 731 are used in combination, and compare tungsten concentrate WO with benzene first hydroximic acid 3the rate of recovery has improved 8.86 percentage points.
Table 3 tungsten ore flotation conditions and result thereof
The application of the positive decoyl amido of embodiment 8:6-hexyl hydroximic acid in ilmenite flotation
Certain ferrotianium is containing ore deposit TiO 222.60%, mog-200 order accounts for 60%, adopts the sulfuric acid adjust pH of 1500g/t, through one roughing operation, obtains titanium rough concentrate, and the flotation results of the positive decoyl amido of 6-hexyl hydroximic acid and benzene first hydroximic acid is in Table 4.Result shows, compares with benzene first hydroximic acid, and the positive decoyl amido of 6-hexyl hydroximic acid can make ilmenite concentrate TiO 2the rate of recovery improves 5.70 percentage points.
Table 4 titanium iron ore flotation conditions and result thereof
The application of embodiment 9:6-valnoctamide base hexyl hydroximic acid in bauxite flotation
Certain bauxite is containing Al 2o 362.01%, SiO 210.98%, mog-200 order accounts for 85%, adopts the sodium carbonate adjust pH of 3000g/t, and the calgon of 30g/t, through one roughing operation, obtains aluminium rough concentrate, and the flotation results of 6-valnoctamide base hexyl hydroximic acid and oleic acid is in Table 5.Result shows, 6-valnoctamide base hexyl hydroximic acid and oleic acid are used in combination, and compare bauxite concentrate Al with benzene first hydroximic acid 2o 3the rate of recovery has improved 6.05 percentage points, and alumina silica ratio A/S has improved 0.42.
Table 5 bauxitic ore flotation conditions and result thereof
The application of embodiment 10:6-(9-octadecylene) amide groups hexyl hydroximic acid in Rare Earth Mine flotation
Certain shaking table rare earth chats REO grade 8.04%, adopts waterglass 1000g/t to make inhibitor, and terpenic oil 80g/t, through one roughing operation, obtains rare earth rough concentrate.The flotation results of 6-(9-octadecylene) amide groups hexyl hydroximic acid and benzene first hydroximic acid is in Table 6, and result shows, compares with benzene first hydroximic acid, and the rare earth yield of 6-(9-octadecylene) amide groups hexyl hydroximic acid flotation has improved 7.00 percentage points.
Table 6 rare earth ore flotation conditions and result thereof
The application of embodiment 11:6-n-dodecane amide groups hexyl hydroximic acid in cassiterite ore floatation
Certain cassiterite raw ore, containing Sn1.11%, adopts sodium carbonate 500g/t, inhibitor tannin consumption 500g/t, and terpenic oil 24g/t, through one roughing operation, obtains cassiterite rough concentrate.The flotation results of 6-n-dodecane amide groups hexyl hydroximic acid and benzene first hydroximic acid is in Table 7, and result shows, compares with benzene first hydroximic acid, and the tin rate of recovery of 6-n-dodecane amide groups hexyl hydroximic acid flotation has improved 5.89 percentage points.
Table 7 cassiterite ore floatation condition and result thereof
The application of embodiment 12:6-hexadecanoyl amido hexyl hydroximic acid in fluorite flotation
Certain fluorite raw ore is containing CaF 239.20%, adopt sodium carbonate 1400g/t, inhibitor waterglass consumption 400g/t, the hybrid collector of oleic acid and hydroximic acid, through one roughing operation, obtains fluorite rough concentrate.The flotation results of 6-hexadecanoyl amido hexyl hydroximic acid and benzene first hydroximic acid is in Table 8, and result shows, compares the CaF of 6-hexadecanoyl amido hexyl hydroximic acid flotation with benzene first hydroximic acid 2the rate of recovery has improved 4.29 percentage points.
Table 8 fluorite ore flotation conditions and result thereof

Claims (7)

1. the application process of a 6-aliphatic group amide groups hexyl hydroximic acid, it is characterized in that, collecting agent using described 6-aliphatic group amide groups hexyl hydroximic acid as scheelite, wolframite, Rare Earth Mine, tin ore, bauxite, ilmenite or fluorite flotation, the structure of described 6-aliphatic group amide groups hexyl hydroximic acid is suc as formula shown in (I):
Wherein R represents C 2~C 18aliphatic group.
2. application process according to claim 1, is characterized in that, the basic operation procedure that 6-aliphatic group amide groups hexyl hydroximic acid is made collecting agent is: (a) after grinde ore, enter flotation; (b) aqueous solution that 6-aliphatic group amide groups hexyl hydroximic acid and NaOH, potassium hydroxide or ammoniacal liquor is made in water to 6-aliphatic group amide groups hexyl hydroximic acid salt is as floating agent; (c) in ore grinding and/or floatation process, add floating agent to size mixing, ilmenite regulates pH4~7 with sulfuric acid, other is mining, and sodium carbonate regulates pH7~12 scope, the aqueous solution that at least contains 6-aliphatic group amide groups hexyl hydroximic acid salt in the medicament adding, the amount ranges 40~1500g/t of 6-aliphatic group amide groups hexyl hydroximic acid; (d) by froth flotation method emersion useful metal mineral.
3. the preparation method of a 6-aliphatic group amide groups hexyl hydroximic acid, it is characterized in that, comprise the following steps: (1) take caprolactam and hydroxylamine hydrochloride or HAS as raw material, the amide groups of two kinds of raw materials: azanol base mol ratio=1:1, toluene is solvent, 80~110 ℃ of reaction temperatures, react 1~4 hour, generate the amino hexyl hydroximic acid of 6-suc as formula structure shown in (II); (2) the amino hexyl hydroximic acid of 6-and C 2~C 18aliphatic carboxylic acid reaction, the amino of two kinds of reactants: carboxyl mol ratio=1:1~1.3, reaction temperature is 100~160 ℃, reacts 1~4 hour, generates the 6-aliphatic group amide groups hexyl hydroximic acid with structure shown in formula (I).
4. preparation method according to claim 3, is characterized in that: described C 2~C 18aliphatic carboxylic acid comprises C 2~C 18alkyl carboxylic acid and containing one or more in the unsaturated alkyl carboxylic acid of alkenyl or alkynyl.
5. according to the preparation method described in claim 3 or 4, it is characterized in that: described C 2~C 18aliphatic carboxylic acid comprises one or more in acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, sad, isooctyl acid, capric acid, oleic acid, linoleic acid, leukotrienes, octenoic acid, decylenic acid, lauroleic acid, laurate, cyclohexanecarboxylic acid, or a kind of in cocinic acid, palmitoleic acid, aphthenic acids.
6. preparation method according to claim 5, is characterized in that: described C 2~C 18aliphatic carboxylic acid comprises one or more in caproic acid, sad, isooctyl acid, capric acid, oleic acid, linoleic acid, leukotrienes, octenoic acid, decylenic acid, lauroleic acid, laurate, cyclohexanecarboxylic acid, or a kind of in cocinic acid, palmitoleic acid, aphthenic acids.
7. preparation method according to claim 3, is characterized in that: solvent load is quality of caprolactam 2~5 times, reaction finishes rear solvent distillation and recycles.
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CN111515029B (en) * 2020-04-30 2022-05-17 江西理工大学 Collecting agent for separating monazite and ilmenite and using method thereof
CN112592305B (en) * 2020-12-23 2022-10-18 中南大学 Organic compound and preparation method and application thereof
CN115819652B (en) * 2022-12-06 2023-09-05 中南大学 2-aminopentanedioxime acid modified polyacrylic acid chelate resin and preparation method and application thereof

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