CN105293447B - The method that reduction iron-based ionic liquid is degraded during catalysis oxidation hydrogen sulfide - Google Patents
The method that reduction iron-based ionic liquid is degraded during catalysis oxidation hydrogen sulfide Download PDFInfo
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Abstract
The method that iron-based ionic liquid is degraded during catalysis oxidation hydrogen sulfide is reduced the invention discloses a kind of, using the initial aqueous rate of reduction iron-based ionic liquid, the flow of reaction temperature and/or oxygen-fed gas is improved to remove the moisture of course of reaction, reduce the moisture content of course of reaction intermediate ion liquid, and then the degraded of organic cation in ionic liquid is reduced, solve [bmim] Fe (III) Cl4During ionic liquid-catalyzed oxidation of sulfureted hydrogen, because ferrous ion is in the presence of water and oxygen, hydroxyl free radical is produced, organic cation is aoxidized, causes the problem of iron-based ionic liquid is degraded during catalysis oxidation hydrogen sulfide.This method is simple, easy to operate, effectively reduces degraded of the iron-based ionic liquid during catalysis oxidation hydrogen sulfide.
Description
Technical field
The present invention relates to liquid phase catalytic oxidation hydrogen sulfide field, more particularly to a kind of reduction iron-based ionic liquid is in catalysis
The method degraded during oxidation of sulfureted hydrogen.
Background technology
The ferricyanide of 1- butyl -3- methylimidazoles four ([bmim] Fe (III) Cl4) ionic liquid-catalyzed-oxidation of sulfureted hydrogen
Process be：[bmim]Fe(III)Cl4First sulphur and 1- butyl -3- methylimidazoles hydrogen four are generated with stink damp precursor reactant
Chlorine perferrite ([bmim] Fe (II) Cl4H) ionic liquid, then oxygen by tetrachloro perferrite ionic liquid oxidation, regeneration
Into [bmim] Fe (III) Cl4And water.In this process, [bmim] Fe (III) Cl4Ionic liquid is catalyst, and oxygen is oxygen
Agent, product is sulphur and water.Sulphur can be recovered by filtration.And [bmim] Fe (III) Cl4Be it is hydrophobic, in theory,
[bmim]Fe(III)Cl4Two-phase should be formed with water, water can also be separated (reference can be made to Chinese patent by point liquid
ZL200910092486.5 related description).But, Lee e al. report 20% (v/v) [bmim] Fe (III) Cl first4
, can be with miscible with water after high degree of agitation.Then, Wang et al. also demonstrate that [bmim] Fe (III) Cl4It can dissolve
In 80% (v/v) water.But, drop water so a small amount of water is dissolved in [bmim] Fe (III) Cl4In will be very tired
Difficult.
In view of water can be with [bmim] Fe (III) Cl4The water formed in homogeneous mixture, iron-based ionic liquid is to lead to
The mode for crossing simple point of liquid is separated.With the progress of catalytic oxidation, water inside iron-based ionic liquid will it is more long-pending more
It is many.If water, oxygen and ferrous ion liquid coexist, in ferrous ion liquid regeneration, hydroxyl free radical will be produced, its process
As shown in following (1), (2) formula：
2[bmim]Fe(II)Cl4 -+O2+H2O→2[bmim]Fe(III)Cl4+H2O2+2OH- (1)
[bmim]Fe(II)Cl4 -+H2O2→[bmim]Fe(III)Cl4+HO·+OH- (2)
Ferrous ion liquid produces hydrogen peroxide with water and oxygen reaction first, then hydrogen peroxide and ferrous ion liquid
The hydroxyl free radical extremely strong by oxidisability is produced, it would be possible to, by the organic cation oxidation of ionic liquid, in turn result in iron
Degraded of the cation during catalysis-oxidation of sulfureted hydrogen in base ionic liquid.
The content of the invention
Based on the problems of above-mentioned prior art, the present invention provides a kind of reduction iron-based ionic liquid in catalysis oxidation
The method degraded during hydrogen sulfide, reduction ion is realized by reducing the water content of iron-based ionic liquid catalysis-oxidation system
The oxidation of organic cation in liquid, and then the cation in iron-based ionic liquid is reduced during catalysis-oxidation of sulfureted hydrogen
Degraded.
In order to solve the above technical problems, the present invention provides a kind of reduction iron-based ionic liquid in catalysis oxidation hydrogen sulfide process
The method of middle degraded, comprises the following steps：
(1) iron-based ionic liquid after rotary evaporation, in being dried in vacuo 12 hours at 80 DEG C, is obtained into drying at 60 DEG C
Iron-based ionic liquid；
(2) at any temperature between the decomposition temperature of room temperature to the iron-based ionic liquid, closed to the step (1)
Into iron-based ionic liquid in simultaneously be passed through purity 99.9% hydrogen sulfide gas and oxygen-fed gas carry out be catalyzed-oxidation reaction 4
~6 hours, the flow for being passed through the hydrogen sulfide gas was 20mL/min, and the oxygen-fed gas uses air or purity 99.9%
Oxygen, use the flow being passed through during oxygen for 20mL/min, use the flow being passed through during air for 100mL/min；
(3) in catalysis-oxidation reaction process of the step (2), it is spaced according to set time from the iron-based ionic liquid
Sampled in body, after sample dilution, the concentration of the sample cationic is measured using ultraviolet specrophotometer, described in measuring
The ratio of concentration and initial concentration determines catalysis-oxidation of sulfureted hydrogen process cationic ([bmim]+) degradation rate；
(4) in catalysis-oxidizing process of the step (2), improve catalysis oxidation temperature and improve oxygen or air
Flow accelerate remove reaction generation moisture reduce cation degradation rate.
Beneficial effects of the present invention are：Before reaction, iron-based ionic liquid is pre-dried, reduction iron-based ionic liquid initially contains
Water rate；In catalysis-oxidation reaction process, improve catalysis oxidation temperature and improve the flow of oxygen or air, accelerate removal anti-
The moisture that should be generated, reduction iron-based ionic liquid is reached by reducing the water content of iron-based ionic liquid catalysis-oxidation system
The purpose of the degradation rate of cationic.This method is simple to operate, can effectively reduce iron-based ionic liquid cationic in catalysis oxygen
Change the degraded during hydrogen sulfide.
Brief description of the drawings
In order to illustrate the technical solution of the embodiments of the present invention more clearly, being used required in being described below to embodiment
Accompanying drawing be briefly described, it should be apparent that, drawings in the following description are only some embodiments of the present invention, for this
For the those of ordinary skill in field, on the premise of not paying creative work, other can also be obtained according to these accompanying drawings
Accompanying drawing.
The method stream that Fig. 1 degrades for the reduction iron-based ionic liquid of the embodiment of the present invention during catalysis oxidation hydrogen sulfide
Journey schematic diagram；
Fig. 2 is reaction unit structural representation of intermediate ion of the embodiment of the present invention liquid during catalysis oxidation hydrogen sulfide
Figure；
Fig. 3 is the initial water content of iron-based ionic liquid in the embodiment of the present invention to [bmim]+The influence figure of degraded；
Fig. 4 is reaction temperature in the embodiment of the present invention to [bmim]+The influence figure of degradation rate；
The corresponding part of each label is in Fig. 2：1-H2S gas cylinders；2- heat collecting type constant-temperature heating magnetic stirring apparatus；Tri- mouthfuls of burnings of 3-
Bottle；4- condenser pipes；5-O2Gas cylinder.
Embodiment
The technical scheme in the embodiment of the present invention is clearly and completely described below, it is clear that described embodiment
Only a part of embodiment of the invention, rather than whole embodiments.Based on embodiments of the invention, ordinary skill
The every other embodiment that personnel are obtained under the premise of creative work is not made, belongs to protection scope of the present invention.
The embodiment of the present invention reduces the method that iron-based ionic liquid is degraded during catalysis oxidation hydrogen sulfide by a kind of
(referring to Fig. 1), comprises the following steps：
(1) iron-based ionic liquid after rotary evaporation, is dried in vacuo 12 hours at 60 DEG C at 80 DEG C, obtains drying
Iron-based ionic liquid；The step can reduce the initial aqueous rate of iron-based ionic liquid, so as to reduce in catalytic oxidation process
Degraded；In this step, iron-based ionic liquid is：The anion ion liquid of ferrous acid containing tetrachloro.It is preferred that the iron-based ionic liquid
Body can be the acid synthesized by iron chloride hexahydrate or anhydrous ferric trichloride with two substitution alkyl imidazole villaumites with arbitrary proportion
The iron-based ionic liquid of property；
(2) at any temperature between the decomposition temperature of room temperature to the iron-based ionic liquid, closed to the step (1)
Into iron-based ionic liquid in the hydrogen sulfide gas and purity of purity 99.9% are passed through with 20mL/min flow simultaneously respectively
99.9% oxygen or air be catalyzed-oxidation reaction 4~6 hours；
(3) in catalysis-oxidation reaction process of the step (2), it is spaced according to set time from the iron-based ionic liquid
Body is sampled, it is preferred that the time interval set is one hour；The amount for taking sample is 0.010g~0.012g, after sample dilution, is adopted
The concentration of the sample cationic is measured with ultraviolet specrophotometer, is come with the concentration and the ratio of initial concentration that measure
It is determined that catalysis-oxidation of sulfureted hydrogen process cationic ([bmim]+) degradation rate；Wherein, sample cationic refers to：1,3- bis-
Any of alkyl imidazole, 1- alkenyl -3- alkyl imidazoles, 1- benzyl -3- alkyl imidazoles, 1- benzyl -3- alkenyl imidazoles, its
In, alkyl is 1-16 containing carbon number, and alkylene is 2-8 containing carbon number；
(4) in catalysis-oxidizing process of the step (2), by improve catalysis oxidation temperature and improve oxygen or
The flow of air, moisture or take away the moisture of reaction generation to reduce cation using dry air-flow that evaporation reaction is generated
Degradation rate.
The method of the present invention is described further with reference to specific embodiment.
The method of the ionic liquid-catalyzed oxidizing process cationic degradation rate of reduction provided in an embodiment of the present invention is：
Under certain temperature, iron-based ionic liquid generates sulphur and ferrous ion liquid with stink damp precursor reactant first, so
Ferrous ion liquid oxidation is regenerated as iron-based ionic liquid and water by oxygen afterwards, is comprised the following steps：
(1) iron-based of iron chloride hexahydrate or anhydrous ferric trichloride and 1- butyl -3- methylimidazole villaumite synthetic acidics
Ionic liquid, iron-based ionic liquid after rotary evaporation, is dried in vacuo 12 hours at 80 DEG C at 60 DEG C, obtains dry iron
Base ionic liquid；The step can reduce the initial aqueous rate of iron-based ionic liquid, so as to reduce in catalytic oxidation process
Degraded；
(2) 20mL/min 99.9% hydrogen sulfide gas and 20mL/min 99.9% oxygen are passed through iron-based ion simultaneously
Carry out being catalyzed-oxidation reaction 4~6 hours in liquid；
(3) in catalysis-oxidation reaction process of step (2), 0.012g is sampled from iron-based ionic liquid every a hour
Left and right, after dilution, the concentration of 1- butyl -4-methylimidazole cation is measured using ultraviolet specrophotometer, concentration is measured with it
1- butyl -3- methyl imidazolium cations ([bmim] during catalysis-oxidation of sulfureted hydrogen are investigated with the ratio of initial concentration+)
Degraded situation；
(4) in catalysis-oxidizing process of the step (2), reaction temperature is improved, accelerates the steaming of the moisture of reaction generation
The degradation rate of hair reduction cation；Or the flow of oxygen or air is improved, the water of reaction generation is taken away using dry air-flow
Divide to reduce the degradation rate of cation.
The embodiment of the present invention realizes effectively reduction iron-based ion by reducing the water content of whole catalytic oxidation system
The purpose of degraded of the liquid during catalysis oxidation hydrogen sulfide.Reducing the water content of catalytic oxidation system includes reduction catalysis
The water content of oxidation system includes drying iron-based ionic liquid, reduces initial aqueous rate, improves the temperature of catalysis oxidation and/or carries
The flow of high oxygen-fed gas, removes the moisture of reaction generation in time.It is recognised that all are conducive to the mode of moisture removal
With application in the method for the invention, the purpose of reduction ionic liquid degradation rate is reached.
Embodiment one
The present embodiment provides a kind of method degraded during reducing iron-based ionic liquid liquid phase catalytic oxidation hydrogen sulfide,
Therefrom, it may be determined that moisture content is to [bmim] after iron-based ionic liquid reaction+The influence of degradation rate, step is as follows：
By FeCl3·6H2O and [bmim] Cl is respectively according to 0.1:1、0.2:1、0.3:1、0.4:1 and 0.5:1 mole
After mixing, stirred in the environment of 40 DEG C of opening to being formed after homogeneous solution, the solution of gained is steamed in 60 DEG C of rotations
Hair, and mol ratio is obtained within 12 hours less than 1 in 80 DEG C of vacuum drying:1 iron-based ionic liquid；
By FeCl3·6H2O and [bmim] Cl is according to 2:After 1 mixed in molar ratio, 24h is stirred under normal temperature, static layering takes
After the liquid of layer, by the solution of gained at 60 DEG C rotary evaporation, and be dried in vacuo and obtain [bmim] at 80 DEG C for 12 hours
FeCl4Ionic liquid；
Using the reaction unit of the catalysis oxidation hydrogen sulfide shown in Fig. 2,33~40mL above-mentioned iron-based ionic liquid is taken
Inject in three-necked flask, at 80 DEG C, control the O of purity 99.9%2Flow is 20mL/min, the H of purity 99.9%2S flows are
After 20mL/min, catalysis-oxidation 4.6-6h, doctor solution is filtered, the aqueous of filtrate is measured using MA150 type analysis of moisture content instrument
In amount, UV-2450 type ultraviolet-visibles analyzer measurement catalytic oxidation system [bmim]+Concentration, the catalysis-oxidation system is anti-
In moisture content and ionic liquid after answering [bmim]+Concentration ratio (C/C before reaction0) as shown in table 1, wherein C represents to react 4.6-
After 6h in ionic liquid [bmim]+The concentration of cation, C0Represent before reaction in ionic liquid [bmim]+The concentration of cation, C/
C0Value it is smaller, show [bmim]+Cation is degraded more.
Influence of the moisture content to degradation rate after table 1 reacts
| Mol ratio | 2:1 | 0.4:1 | 0.5:1 | 0.1:1 | 0.2:1 | 0.3:1 |
| Initial aqueous rate/% | 0.4 | 0.6 | 0.6 | 0.2 | 0.4 | 0.2 |
| Moisture content/% after reaction | 1.26 | 1.48 | 2.12 | 2.28 | 2.45 | 7.23 |
| (C/C0)/% | 97.22 | 96.73 | 95.01 | 91.77 | 93.88 | 83.5 |
As shown in Table 1, by rotary evaporation and vacuum drying iron-based ionic liquid, initial aqueous rate is all very low.But
The moisture content of iron-based ionic liquid substantially rises after reaction, and C/C0Value and reacted moisture content exist it is obvious related
Property, with the increase of moisture content after reaction, C/C0Value substantially reduce, such as when moisture content by mol ratio be 2:1.26% liter of 1
A height of mol ratio is 0.3:1 7.23% when, C/C0Value be reduced to 83.50% by 97.22%.This shows to contain with after reaction
The increase of water rate, the degradation rate increase of iron-based ionic liquid cation.So, generated if can remove in time in catalytic oxidation process
Water, with regard to that can effectively reduce [bmim]+Degradation rate.
Embodiment two
The present embodiment provides a kind of method degraded during reducing iron-based ionic liquid liquid phase catalytic oxidation hydrogen sulfide,
Therefrom, it may be determined that initial aqueous rate is to [bmim]+The influence of degradation rate, step is as follows：
FeCl3·6H2O and [bmim] Cl is according to 0.4:Stirred after 1 mixed in molar ratio in the environment of 40 DEG C of opening to
Formed after homogeneous solution, by the solution of gained in 60 DEG C of rotary evaporations, and moisture content is obtained within 12 hours in 80 DEG C of vacuum drying
For 0.6% iron-based ionic liquid；
FeCl3·6H2O and [bmim] Cl is according to 0.4:After 1 mixed in molar ratio, stirred in the environment of 40 DEG C of opening to
Formed after homogeneous solution, obtain the iron-based ionic liquid that moisture content is 11.07%；
Using the reaction unit shown in Fig. 2, take 40mL iron-based ionic liquid to inject in three-necked flask, at 80 DEG C, control
The O of purity 99.9% processed2Flow be 20mL/min, the H of purity 99.9%2S flow is 20mL/min, every a hour
Using UV-2450 type ultraviolet-visibles analyzer measure catalytic oxidation system in [bmim]+concentration, its react after concentration with just
Ratio (the C/C of beginning concentration0) as shown in Figure 3.The iron-based ionic liquid that moisture content is 11.07% as shown in Figure 3 is in catalysis oxidation
During hydrogen sulfide, C/C0Value significantly lower than moisture content be 0.6% iron-based ionic liquid, this show by the present invention method drop
The initial aqueous rate of low ionic liquid, is effectively reduced [bmim]+Degradation rate.
Embodiment three
The present embodiment provides a kind of method degraded during reducing iron-based ionic liquid liquid phase catalytic oxidation hydrogen sulfide,
Therefrom, it may be determined that temperature is to [bmim]+The influence of degradation rate, step is as follows：
FeCl3·6H2O and [bmim] Cl is according to 2:After 1 mixed in molar ratio, 24h is stirred under normal temperature, static layering takes
After the liquid of layer, by the solution of gained at 60 DEG C rotary evaporation, and be dried in vacuo and obtain [bmim] at 80 DEG C for 12 hours
FeCl4Ionic liquid.
It is 2 to take 33mL mol ratios:1 iron-based ionic liquid is injected in Fig. 1 three-necked flask, respectively at 25 DEG C and 80 DEG C
Under, control the O of purity 99.9%2Flow be 20mL/min, the H of purity 99.9%2S flow is 20mL/min, every one
Hour utilizes [bmim] in UV-2450 type ultraviolet-visibles analyzer measurement catalytic oxidation system+Concentration；Mol ratio is 2:1
Iron-based ionic liquid at different temperature catalysis oxidation hydrogen sulfide when, its C/C0Value change with time as shown in Figure 4.
In catalysis-oxidation identical time, 80 DEG C of C/C0Value apparently higher than the numerical value at 25 DEG C, this shows by the present invention's
Method raises reaction temperature, accelerates the evaporation of moisture, then effectively reduces degradation rate, the specific model for improving catalysis oxidation temperature
The decomposition temperature to ionic liquid for room temperature is enclosed, temperature is improved, accelerates the evaporation of moisture, preferably reduction degradation rate can be reached
Effect.
Example IV
The present embodiment provides a kind of method degraded during reducing iron-based ionic liquid liquid phase catalytic oxidation hydrogen sulfide,
Therefrom, it may be determined that improve gas flow to [bmim]+The influence of degradation rate, step is as follows：
FeCl3·6H2O and [bmim] Cl is according to 2:After 1 mixed in molar ratio, 24h is stirred under normal temperature, static layering takes
After the liquid of layer, by the solution of gained at 60 DEG C rotary evaporation, and be dried in vacuo and obtain [bmim] at 80 DEG C for 12 hours
FeCl4Ionic liquid.
It is 2 to take 33mL mol ratios:1 iron-based ionic liquid is injected in Fig. 1 three-necked flask, at 80 DEG C, controls air
Flow be 100mL/min, the H of purity 99.9%2S flow is 20mL/min, purple using UV-2450 types every a hour
In outer visible light analysis instrument measurement catalytic oxidation system [bmim]+Concentration；It was found that C/C0Value at 1,2,3,4,5,6,7 hour
It is 1.This shows the flow that the air as oxygen-fed gas is improved by the method for the present invention, accelerates the evaporation of moisture, then
Degradation rate is effectively reduced, the scope of the specific flow for improving oxygen-fed gas is theoretical oxygen demand more than 5 times, can reach preferably
Reduce the effect of degradation rate.
Further, can be on the basis of above-described embodiment, while improving the temperature of catalysis oxidation and the stream of oxygen-fed gas
Amount, realizes that evaporation and pneumatic conveying drying double action remove the water that reaction is produced, effectively to reduce in catalytic oxidation [bmim]+
Degradation rate.
The foregoing is only a preferred embodiment of the present invention, but protection scope of the present invention be not limited thereto,
Any one skilled in the art is in the technical scope of present disclosure, the change or replacement that can be readily occurred in,
It should all be included within the scope of the present invention.Therefore, protection scope of the present invention should be with the protection model of claims
Enclose and be defined.
Claims (5)
1. a kind of reduce the method degraded during catalysis oxidation hydrogen sulfide of iron-based ionic liquid, it is characterised in that including with
Lower step：
(1) iron-based ionic liquid after rotary evaporation, in being dried in vacuo 12 hours at 80 DEG C, is obtained into dry iron-based at 60 DEG C
Ionic liquid；
(2) at any temperature between the decomposition temperature of room temperature to the iron-based ionic liquid, synthesized to the step (1)
The hydrogen sulfide gas and oxygen-fed gas for being passed through purity 99.9% in iron-based ionic liquid simultaneously be catalyzed-and oxidation reaction 4~6 is small
When, the flow for being passed through the hydrogen sulfide gas is 20mL/min, and the oxygen-fed gas uses air or the oxygen of purity 99.9%,
The flow being passed through during oxygen is used for 20mL/min, the flow being passed through during air is used for 100mL/min；
(3) in catalysis-oxidation reaction process of the step (2), it is spaced according to set time from the iron-based ionic liquid
Sampling, after the dilution of ionic liquid sample, the concentration of the ionic liquid sample cationic is measured using ultraviolet specrophotometer,
Catalysis-oxidation of sulfureted hydrogen process cationic ([bmim] is determined with the concentration that measures and the ratio of initial concentration+)
Degradation rate；
(4) in catalysis-oxidizing process of the step (2), improve catalysis oxidation temperature and/or improve the stream of oxygen-fed gas
Amount, accelerating to remove the moisture of reaction generation reduces the degradation rate of cation；In the step (4), the model of catalysis oxidation temperature is improved
Enclose for room temperature to ionic liquid degradation temperature；The scope for improving the flow of oxygen-fed gas is more than 5 times of theoretical oxygen demand.
2. the method that reduction iron-based ionic liquid according to claim 1 is degraded during catalysis oxidation hydrogen sulfide, its
It is characterised by, the iron-based ionic liquid is：The anion ion liquid of ferrous acid containing tetrachloro.
3. the method that reduction iron-based ionic liquid according to claim 1 or 2 is degraded during catalysis oxidation hydrogen sulfide,
Characterized in that, the iron-based ionic liquid is by iron chloride hexahydrate or anhydrous ferric trichloride and two substitution alkyl imidazole chlorine
The acid iron-based ionic liquid that salt is synthesized with arbitrary proportion.
4. the method that reduction iron-based ionic liquid according to claim 1 or 2 is degraded during catalysis oxidation hydrogen sulfide,
Characterized in that, the ionic liquid sample cationic is：1,3- dialkylimidazoliums, 1- alkenyl -3- alkyl imidazoles, 1- benzyls
Any of base -3- alkyl imidazoles, 1- benzyl -3- alkenyl imidazoles, wherein, alkyl containing carbon number be 1-16, alkylene it is carbon containing
Number is 2-8.
5. the method that reduction iron-based ionic liquid according to claim 1 or 2 is degraded during catalysis oxidation hydrogen sulfide,
Characterized in that, the time interval set in the step (3) is one hour；The amount for taking sample is 0.010g~0.012g.
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