CN104646186A - Triester-based quaternary ammonium salt positive ion collecting agent and preparation method and application thereof - Google Patents
Triester-based quaternary ammonium salt positive ion collecting agent and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a triester-based quaternary ammonium salt positive ion collecting agent. The general formula I of the collecting agent is as follows, FORMULA, wherein n is any integer from 1 to 3, R is selected from straight chain or branched chain alkyl groups of C12-C21, and X is selected from a helium atom or a bromine atom. A molecule of the triester-based quaternary ammonium salt positive ion collecting agent contains a hydrophilic group hydroxyl which is easy to dissolve; when being applied to mineral flotation, the collecting agent is high in collecting performance and selectivity; formed foams are fine, fragile and easy to eliminate; when the collecting agent is used, no acid is needed to be added for dissolving, so that equipment cannot be corroded; meanwhile, the collecting agent is good in flotation effect under a low-temperature condition; the preparation technology is simple and easy to operate; the triester-based quaternary ammonium salt positive ion collecting agent is environment-friendly.
Description
Technical field
The present invention relates to beneficiation reagent, be specifically related to a kind of three ester based quaternary ammonium salt cation-collecting agents and its preparation method and application.
Background technology
In China, the main component of magnetic iron ore and bloodstone gangue is quartz, and the too high meeting of quartz content causes the capacity factor of a blast furnace to reduce, iron production declining, and ironmaking cost increases.Therefore, for providing high-quality iron ore concentrate to steel industry, the iron ore higher to quartz content is carried Fe and reducing Si and is seemed particularly important.Current iron ore flotation mainly contains three kinds of technological processes: 1) direct flotation, suppresses silicates mineral, with anionic collector Iron Ore Flotation thing; 2) reverse flotation, presses down iron and floats silicon, with cation-collecting agent reverse flotation gangue, stayed by iron mineral in flotation cell; 3) anti-floating silicates gangue mineral, with the gangue after the activation of anionic collector reverse flotation.In actual production, cation reverse flotation is simple owing to having regime of agent, advantages such as good resistance to low temperature and extensively adopting.
At present, conventional both at home and abroad amine cation-collecting agent mainly contains acid amides, ether amine, polyamines, amine condensation and salt thereof etc.The beneficiation reagent major part used in China mine is high poison, the kind of high pollution, environmental pollution and serious, and along with China advocates development Intensive economy energetically, reduce energy consumption, eco-friendly cation-collecting agent should be greatly developed in China.But the amine cation-collecting agent of routine is water-soluble poor, acid medium need be dissolved in and uses.In actual industrial production, acid medium meeting etching apparatus, waste water also needs neutralisation treatment.And conventional amine collector foam is clamminess, poor fluidity, not easily froth breaking, easily cause in the industrial production running groove phenomenon, need constantly to add water and improve concentrate bubble mobility in floatation process.The ammonia nitrogen of amine collector can have certain pollution to water quality simultaneously, therefore, actively develops research high-efficiency low-toxicity type amine cation-collecting agent significant.
Summary of the invention
The object of this invention is to provide a kind of New Ester based quaternary ammonium salt class collecting agent with excellent collecting ability, selective and good resistance to low temperature, and the preparation method related to is simple to operation, can meet in iron ore flotation the practicality requirement carrying Fe and reducing Si.
For achieving the above object, the technical solution used in the present invention is: a kind of three ester based quaternary ammonium salt cation-collecting agents, and its general formula is as general formula I:
In formula, n is arbitrary integer of 1 ~ 3, and R is selected from C
12~ C
21straight or branched alkyl, X is selected from chlorine atom or bromine atoms.
The preparation method of above-mentioned a kind of three ester based quaternary ammonium salt cation-collecting agents, comprises the following steps:
1) quaterisation: epoxy halogenated alkane and reaction dissolvent are added in reaction vessel, then tertiary amine is dripped, the mol ratio of epoxy halogenated alkane and tertiary amine is 5:(1.5 ~ 3), be heated to 50 ~ 80 DEG C, react 10 ~ 12h under agitation, reaction dissolvent is removed in distillation, obtains intermediate product;
2) esterification: by step 1) intermediate product that obtains and citric acid be by (3 ~ 3.5): the mol ratio of 1 adds in reaction vessel, then reaction dissolvent and p-methyl benzenesulfonic acid is added, the addition of p-methyl benzenesulfonic acid is 1 ~ 3% of citric acid quality, then 100 ~ 130 DEG C are heated to, stirring and refluxing 5 ~ 10h, reaction dissolvent is removed in distillation, obtains described three ester based quaternary ammonium salt cation-collecting agents.
According to such scheme, the general formula of described epoxy halogenated alkane is such as formula II:
In formula, n is arbitrary integer of 1 ~ 3, and X is selected from chlorine atom or bromine atoms.
According to such scheme, the general formula of described tertiary amine is such as formula III:
In formula, n is arbitrary integer of 11 ~ 20.
According to such scheme, described reaction dissolvent is acetone, methyl alcohol, ethanol, ethylene glycol, normal propyl alcohol or isopropyl alcohol.
The another kind of preparation method of above-mentioned three ester based quaternary ammonium salt cation-collecting agents, comprise the following steps: adopt one-step method for synthesizing, by epoxy halogenated alkane and citric acid with (3 ~ 3.5): the mol ratio of 1 adds in reaction vessel, add reaction dissolvent, then drip tertiary amine, the mol ratio of tertiary amine and citric acid is (3 ~ 5): 1, be heated to 80 ~ 120 DEG C, reaction 8 ~ 12h, reaction dissolvent is removed in distillation, obtains described three ester based quaternary ammonium salt cation-collecting agents.
According to such scheme, the general formula of described epoxy halogenated alkane is as general formula II:
In formula, n is arbitrary integer of 1 ~ 3, and X is selected from chlorine atom or bromine atoms.
According to such scheme, the general formula of described tertiary amine is such as formula III:
In formula, n is arbitrary integer of 11 ~ 20.
According to such scheme, described reaction dissolvent is acetone, methyl alcohol, ethanol, ethylene glycol, normal propyl alcohol or isopropyl alcohol.
Three ester based quaternary ammonium salt cation-collecting agents of the present invention can be applicable to the minals such as flotation quartz and magnetic iron ore.
Three ester based quaternary ammonium salt cation-collecting agents of the present invention are applied to Iron Ore Flotation stone, embody rule method is: take sample ore 200 ~ 300g, adjustment pulp density is 25 ~ 35wt%, add three ester based quaternary ammonium salt cation-collecting agent 300 ~ 600g/t again, last blowing air fully stirs reverse flotation, obtains the iron ore concentrate that grade promotes.
Three ester based quaternary ammonium salt cation-collecting agents of the present invention are applied to Iron Ore Flotation stone, embody rule method is: take sample ore 200 ~ 300g, adjustment pulp density is 25 ~ 35wt%, then 200 ~ 400g/t inhibitor starch is added, add three ester based quaternary ammonium salt cation-collecting agent 300 ~ 600g/t again, last blowing air fully stirs reverse flotation, obtains the iron ore concentrate that grade promotes.
Compared with prior art, beneficial effect of the present invention is:
1) easy froth breaking: the froth pulp froth breaking floatingly selected is fast, is conducive to follow-up operation.
2) low temperature resistant: the beneficiating efficiency obtained about 5 DEG C flotation is 17.12%, can save the expense of heating.
3) soluble: three ester based quaternary ammonium salt cation-collecting agents of the present invention contain hydrophilic group hydroxyl, in use soluble, simple to operate during preparation, do not need to use acid to dissolve, not etching apparatus; And the amine cation-collecting agent of the routine such as lauryl amine need use acid to dissolve.
4) practical: three ester based quaternary ammonium salt cation-collecting agents of the present invention selective good, collecting performance is comparatively strong, and the synthetic route related to is simple and safe, and raw material sources are extensive.
5) System of Flotation Reagent is simple: when gained three ester based quaternary ammonium salt cation-collecting agent of the present invention is used for flotation, without the need to adding the medicament such as foaming agent, activator, simple to operate, saves production cost.
Accompanying drawing explanation
Below in conjunction with drawings and Examples, the invention will be further described, in accompanying drawing:
Fig. 1 is the infrared spectrogram of the three ester based quaternary ammonium salt cation-collecting agents that the embodiment of the present invention 1 obtains.
Fig. 2 is the flow chart that the obtained three ester based quaternary ammonium salt cation-collecting agents of the embodiment of the present invention 1 carry out minal flotation.
Fig. 3 is the flow chart (without inhibitor) that the obtained three ester based quaternary ammonium salt cation-collecting agents of the embodiment of the present invention 1 carry out iron ore flotation.
Fig. 4 is the flow chart (interpolation inhibitor) that the obtained three ester based quaternary ammonium salt cation-collecting agents of the embodiment of the present invention 1 carry out iron ore flotation.
Detailed description of the invention
In order to make object of the present invention, technical scheme and advantage clearly understand, below in conjunction with drawings and Examples, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
The quartzy minal adopted in following examples and magnetic iron ore minal provide by University of Queensland's JuliusKruttschnitt Mineral Research Center, and its chemical composition analysis is respectively in table 1 and table 2.
The iron ore adopted is the roasting magnetic iron ore that wine steel is produced, and its chemical composition analysis is in table 3, and this iron in ore grade is 52%, and impure mineral is mainly silicates, difficult ore dressing.
Embodiment 1
A kind of three ester based quaternary ammonium salt cation-collecting agents, its preparation method comprises the following steps:
1) taking 0.5mol epoxychloropropane adds in the there-necked flask that reflux condensing tube and dropping funel are housed, add 70g acetone as reaction dissolvent, there-necked flask is placed in oil bath pan and is heated to 60 DEG C, dodeca-tertiary amine 0.2mol is slowly dripped with dropping funel, magnetic agitation 12h, rotary distillation goes out the intermediate product that solvent acetone must be weak yellow liquid afterwards.
2) getting the intermediate product that 0.2mol obtains adds in there-necked flask, add 0.06mol (11.52g) citric acid, add 70g isopropyl alcohol as reaction dissolvent, the p-methyl benzenesulfonic acid adding citric acid quality 2% (0.23g), as catalyst, is heated to 100 DEG C of return stirring 9h.Then product rotary distillation is gone out solvent, obtain described three ester based quaternary ammonium salt cation-collecting agents, in flaxen colloidal objects, recording cationic degree by tetraphenylboron sodium back titration is 83%.
The infrared spectrogram of the three ester based quaternary ammonium salt cation-collecting agents that the present invention obtains is shown in Fig. 1, in figure: at 3273cm
-1there is a strong and wide absworption peak at place, and this is the characteristic absorption peak of association OH group stretching vibration, 2924cm
-1, 2854cm
-1place is CH
3, CH
2the stretching vibration peak of molecular radical; And this absworption peak is very strong, embodies the architectural feature of chain alkyl methyl type cationic surfactant; 1737cm
-1there is strong absorption at place, is the stretching vibration peak of carbonyl (C=O) molecular radical; 1467cm
-1the absorption at place is the characteristic absorption of quaternary ammonium root; 1180cm
-1place is ester group stretching vibration peak in product structure; 1108cm
-1place is the stretching vibration peak of C-N key.911cm is there is not in collection of illustrative plates
-1, 851cm
-1the characteristic absorption peak of epoxy bond, illustrate that epoxy bond disappears.
Embodiment 2
A kind of three ester based quaternary ammonium salt cation-collecting agents, its preparation method comprises the following steps:
1) taking 0.5mol epoxy bromopropane adds in the there-necked flask that reflux condensing tube and dropping funel are housed, add 70g acetone as reaction dissolvent, there-necked flask is placed in oil bath pan and is heated to 80 DEG C, dodeca-tertiary amine 0.25mol is slowly dripped with dropping funel, magnetic agitation 11h, rotary distillation goes out the intermediate product that solvent acetone must be weak yellow liquid afterwards.
2) getting the intermediate product that 0.25mol obtains adds in there-necked flask, add 0.08mol (15.36g) citric acid, add 76.8g acetone as reaction dissolvent, the p-methyl benzenesulfonic acid adding citric acid quality 2.5% (0.384g), as catalyst, is heated to 120 DEG C of return stirring 6h.Then product rotary distillation is gone out solvent, obtain described three ester based quaternary ammonium salt cation-collecting agents, in flaxen colloidal objects.The cationic degree adopting tetraphenylboron sodium back titration to record the three ester based quaternary ammonium salt cation-collecting agents that the present embodiment obtains is 80%.
Embodiment 3
A kind of three ester based quaternary ammonium salt cation-collecting agents, its preparation method comprises the following steps:
Take epoxychloropropane 0.21mol, citric acid 0.06mol joins and dropping funel is housed, in the there-necked flask of reflux condensing tube, add 57.5g isopropyl alcohol and slowly drip dodeca-tertiary amine 0.2mol (42.6g) as after solvent magnetic agitation 20min with dropping funel, be heated to 100 DEG C of condensing refluxes and react 12 hours, rotary distillation goes out solvent isopropyl alcohol afterwards, obtain flaxen jelly, i.e. described three ester based quaternary ammonium salt cation-collecting agents, recording cationic degree by tetraphenylboron sodium back titration is 82%.
Embodiment 4
A kind of three ester based quaternary ammonium salt cation-collecting agents, its preparation method comprises the following steps:
Take epoxy bromopropane 0.24mol (32.8g), citric acid 0.08mol (15.36g) joins and dropping funel is housed, in the there-necked flask of reflux condensing tube, add normal propyl alcohol 76.8g (5 times of citric acid quality) and slowly drip dodeca-tertiary amine 0.28mol (59.64g) as after solvent magnetic agitation 20min with dropping funel, be heated to 120 DEG C of condensing refluxes and react 8 hours, rotary distillation goes out solvent normal propyl alcohol afterwards, obtain flaxen jelly, i.e. described three ester based quaternary ammonium salt cation-collecting agents, recording cationic degree by tetraphenylboron sodium back titration is 81%.
Application examples 5
Product prepared by embodiment 1 is used for flotation quartz minal and magnetic iron ore minal, the flotation flowsheet of employing is shown in Fig. 2, adopts III grade of ultra-pure water that three obtained ester based quaternary ammonium salt cation-collecting agents are configured to concentration and is respectively 0.03 × 10
-3mol/L, 0.05 × 10
-3mol/L, 0.1 × 10
-3mol/L, 0.5 × 10
-3mol/L and 1 × 10
-3the solution of mol/L.The minal taking 3.0g is respectively placed in the flotation cell of SFG hanging trough flotator, adds the solution configured and carries out flotation.Collect product in gained froth pulp and groove, dry the calculating rate of recovery of weighing, each point in triplicate, finally determines the optium concentration of collecting agent.Afterwards, under optium concentration, carry out pH value experiment, the results are shown in Table 4 and table 5.Result shows that in concentration be 0.05 × 10
-3under the condition of mol/L, pH=7, the rate of recovery of quartz can reach 95.07%, and magnetic iron ore is only 11%, illustrates that three ester based quaternary ammonium salt cation-collecting agents that the present invention obtains have good collecting performance and selective, and collecting better performances in neutral conditions.
Application examples 6
Product prepared by embodiment 1 is used for the roasting magnetic iron ore of flotation wine steel, the flow process of employing as shown in Figure 3.In floatation process, take sample ore 200g, pulp density is transferred to 30wt%, and floating agent three ester based quaternary ammonium salt cation-collecting agent consumption is 400g/t, pH value 7, and when being 52% to ore deposit Iron grade, the floatation indicators of acquisition is as shown in table 6.Result according to table 6 can be found out: Iron grade is 56.39%, and the rate of recovery is 70.58%, and beneficiating efficiency is 19.96%.Compared with traditional cation-collecting agent lauryl amine, slightly lower than the beneficiating efficiency of lauryl amine, but in floatation process, lauryl amine need use acid dissolve, aborning can etching apparatus, and foam is clamminess, mobility is very poor, and froth pulp is difficult to froth breaking, can have a strong impact on follow-up operation.And containing hydrophilic radical hydroxyl in three ester based quaternary ammonium salt cation-collecting agents prepared by the present invention, good water solubility, foam easily disappears, environmental friendliness, and composite factor is considered, the flotation effect of gained three ester based quaternary ammonium salt cation-collecting agent of the present invention is better than lauryl amine.
Application examples 7
Product obtained for embodiment 1 is used for the roasting magnetic iron ore of flotation wine steel, adopt starch as inhibitor, adding amount of starch is 200g/t, floating agent three ester based quaternary ammonium salt cation-collecting agent consumption is 400g/t, pulp density is transferred to 30wt%, as shown in Figure 4, when being 52% to ore deposit Iron grade, the floatation indicators of acquisition is as shown in table 7 for flotation flowsheet.As can be seen from Table 7, add starch as after inhibitor, the beneficiating efficiency of three ester based quaternary ammonium salt cation-collecting agents and lauryl amine is improved, and the beneficiating efficiency of three ester based quaternary ammonium salt cation-collecting agents is higher than lauryl amine.
Application examples 8
Product obtained for embodiment 1 is used under cryogenic the roasting magnetic iron ore of flotation wine steel, adopt starch as inhibitor, adding amount of starch is 200g/t, floating agent three ester based quaternary ammonium salt cation-collecting agent consumption is 400g/t, pulp density is transferred to 30wt%, flotation flowsheet as shown in Figure 4, be carry out flotation under the condition of 5 DEG C in temperature, the floatation indicators obtained is as shown in table 8, result according to table 8: carry out flotation under cryogenic, three obtained ester based quaternary ammonium salt cation-collecting agent beneficiating efficiencies are higher than the beneficiating efficiency of traditional medicament lauryl amine, illustrate that the collecting agent that the present invention obtains has good collecting performance and selectivity, and the synthesis technique related to is simple, frothing capacity is good, low temperature resistant, a large amount of expenses of heating can be saved, during flotation, regime of agent is simple.Consider economic factor and environmental factor, the collecting agent that the present invention obtains is a kind of excellent cation-collecting agent, can be used for flotation field.
Application examples 9
Product prepared by embodiment 3 is used for flotation quartz minal and magnetic iron ore minal, the flotation flowsheet of employing is shown in Fig. 2, is the collecting performance exploring product in embodiment 3 under the condition of 7 according to the result of application examples 5 in pH value.Adopt III grade of ultra-pure water that three obtained ester based quaternary ammonium salt cation-collecting agents are configured to concentration and be respectively 0.03 × 10
-3mol/L, 0.05 × 10
-3mol/L, 0.1 × 10
-3mol/L, 0.5 × 10
-3mol/L and 1 × 10
-3the solution of mol/L.The minal taking 3.0g is respectively placed in the flotation cell of SFG hanging trough flotator, adds the solution configured and carries out flotation.Collect product in gained froth pulp and groove, dry the calculating rate of recovery of weighing, each point in triplicate, finally determines the optium concentration of collecting agent.The result of table 9 shows: at pH=7, and concentration is 0.05 × 10
-3under the condition of mol/L, the rate of recovery of quartz can reach 94.23%, and magnetic iron ore is only 13.56%, illustrates that three ester based quaternary ammonium salt cation-collecting agents that the present invention obtains have good collecting performance and selective, and collecting better performances in neutral conditions.
Subordinate list
Table 1 quartzy minal chemical composition analysis result (%)
Table 2 magnetic iron ore minal chemical composition analysis result (%)
Table 3 roasting magnetic iron ore chemical composition analysis result (%)
The collecting agent concentration that table 4 embodiment 1 obtains is on the impact of the minal rate of recovery
On the impact of the collecting agent flotation minal that embodiment 1 obtains, (collecting agent concentration is 0.05 × 10 to table 5 pH value
-3mol/L)
Table 6 collecting agent kind result of the test
Table 7 collecting agent kind result of the test
The flotation experiments result of collecting agent under 5 DEG C of conditions that table 8 embodiment 1 is obtained
The collecting agent concentration that table 9 embodiment 3 obtains is on the impact of the minal rate of recovery
Bound value, the interval value of each raw material that the present invention relates to can realize the present invention, and lower limit value and the interval value of technological parameter of the present invention (as temperature, time etc.) can realize the present invention, do not enumerate embodiment at this.And the above is only the preferred embodiment of the present invention, it should be pointed out that for the person of ordinary skill of the art, without departing from the concept of the premise of the invention, make some improvement and conversion, these all belong to protection scope of the present invention.
Claims (10)
1. three ester based quaternary ammonium salt cation-collecting agents, its general formula is such as formula I:
In formula, n is arbitrary integer of 1 ~ 3, and R is selected from C
12~ C
21straight or branched alkyl, X is selected from chlorine atom or bromine atoms.
2. the preparation method of three ester based quaternary ammonium salt cation-collecting agents described in claim 1, is characterized in that, comprise the following steps:
1) quaterisation: epoxy halogenated alkane and reaction dissolvent are added in reaction vessel, then tertiary amine is dripped, the mol ratio of epoxy halogenated alkane and tertiary amine is 5:(1.5 ~ 3), be heated to 50 ~ 80 DEG C, react 10 ~ 12h under agitation, reaction dissolvent is removed in distillation, obtains intermediate product;
2) esterification: by step 1) intermediate product that obtains and citric acid be by (3 ~ 3.5): the mol ratio of 1 adds in reaction vessel, then reaction dissolvent and p-methyl benzenesulfonic acid is added, the addition of p-methyl benzenesulfonic acid is 1 ~ 3% of citric acid quality, then 100 ~ 130 DEG C are heated to, stirring and refluxing 5 ~ 10h, reaction dissolvent is removed in distillation, obtains described three ester based quaternary ammonium salt cation-collecting agents.
3. preparation method according to claim 2, is characterized in that, the general formula of described epoxy halogenated alkane is such as formula II:
In formula, n is arbitrary integer of 1 ~ 3, and X is selected from chlorine atom or bromine atoms.
4. preparation method according to claim 2, is characterized in that, the general formula of described tertiary amine is such as formula III:
In formula, n is arbitrary integer of 11 ~ 20.
5. preparation method according to claim 2, is characterized in that, described reaction dissolvent is acetone, methyl alcohol, ethanol, ethylene glycol, normal propyl alcohol or isopropyl alcohol.
6. the preparation method of three ester based quaternary ammonium salt cation-collecting agents described in claim 1, it is characterized in that, adopt one-step method for synthesizing, by epoxy halogenated alkane and citric acid with (3 ~ 3.5): the mol ratio of 1 adds in reaction vessel, adds reaction dissolvent, then tertiary amine is dripped, the mol ratio of tertiary amine and citric acid is (3 ~ 5): 1, is heated to 80 ~ 120 DEG C, reaction 8 ~ 12h, reaction dissolvent is removed in distillation, obtains described three ester based quaternary ammonium salt cation-collecting agents.
7. preparation method according to claim 6, is characterized in that, the general formula of described epoxy halogenated alkane is such as formula II:
In formula, n is arbitrary integer of 1 ~ 3, and X is selected from chlorine atom or bromine atoms.
8. preparation method according to claim 6, is characterized in that, the general formula of described tertiary amine is such as formula III:
In formula, n is arbitrary integer of 11 ~ 20.
9. preparation method according to claim 6, is characterized in that, described reaction dissolvent is acetone, methyl alcohol, ethanol, ethylene glycol, normal propyl alcohol or isopropyl alcohol.
10. three ester based quaternary ammonium salt cation-collecting agent flotation minals described in any one of claim 1 ~ 9 and the application of ore.
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| CN106238215A (en) * | 2016-08-30 | 2016-12-21 | 中蓝连海设计研究院 | A kind of collophane quaternary ammonium salt cationic collecting agent and synthetic method thereof and application |
| CN115400881A (en) * | 2022-08-26 | 2022-11-29 | 广东邦普循环科技有限公司 | Method for purifying and whitening phosphogypsum |
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| CN102112235A (en) * | 2008-11-07 | 2011-06-29 | 科莱恩金融(Bvi)有限公司 | Mixture of an amine alkoxylate ester and a quaternary ammonium compound as a collector for minerals containing silicate |
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| CN102770213A (en) * | 2010-01-19 | 2012-11-07 | 科莱恩金融(Bvi)有限公司 | Flotation reagent for iron ores containing magnetite and/or haematite |
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| CN106238215A (en) * | 2016-08-30 | 2016-12-21 | 中蓝连海设计研究院 | A kind of collophane quaternary ammonium salt cationic collecting agent and synthetic method thereof and application |
| CN115400881A (en) * | 2022-08-26 | 2022-11-29 | 广东邦普循环科技有限公司 | Method for purifying and whitening phosphogypsum |
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Application publication date: 20150527 |