CN109406609B - Electrochemical method for on-line analysis of nitro reduction reaction - Google Patents
Electrochemical method for on-line analysis of nitro reduction reaction Download PDFInfo
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Abstract
The invention discloses an electrochemical method for on-line analysis of nitro reduction reaction. The method comprises the following steps: (1) putting the mixed solution of polyelectrolyte and organic solvent into a dialysis membrane device; (2) and (2) placing the working electrode, the counter electrode and the reference electrode in the dialysis membrane device in the step (1), then placing the dialysis membrane device in the nitro compound reaction solution, and then connecting an electrochemical system circuit, so that the nitro reduction reaction can be analyzed and detected. The material selected by the analysis method of the invention has low toxicity, the detection device of the nitro reduction reaction can be simplified, the detection process can be rapidly completed through the diffusion effect of the nitro compound on the microelectrode, and the feasibility of on-line monitoring of the organic reaction is greatly solved due to the combination of the two technologies which are applied to the electrochemical volt-ampere detection technology by the membrane technology.
Description
Technical Field
The invention belongs to the technical field of detection in the chemical industry, and particularly relates to an electrochemical method for on-line analysis of a nitro reduction reaction.
Background
Nitrobenzene is a basic raw material widely applied in the chemical industry and mainly participates in reduction reaction to prepare various intermediates of fine chemical industry. The nitro reduction reaction is one of the more common reactions in the chemical industry, and currently, in the chemical production, the analysis and test of the reaction mainly relate to chromatographic methods such as liquid phase, gas phase, mass spectrum and the like.
For monitoring the nitro reduction reaction, a central control sample is sampled at multiple points, and analysis and detection are carried out by using analytical instruments such as High Performance Liquid Chromatography (HPLC) or Gas Chromatography (GC), and the analytical methods have high sensitivity, but the sample pretreatment is complicated, the operation is complex, and longer time is needed, so that the working tasks of analytical departments are increased, and the progress and the efficiency of chemical production are influenced. For example, analytical instruments such as Gas Chromatography (GC) perform analytical tests for at least 30 minutes or more. In addition, there are many unsafe factors in the sampling process, influence staff's safety and social environment, even cause the huge economic loss of enterprise to detect and consume great, can't detect shortcoming such as real-time on line.
Therefore, the research and development of an analysis method for the nitro reduction reaction, which can realize real-time online detection, has good selectivity, high analysis speed, simple operation, convenient maintenance and low detection cost, still remains a problem to be solved in the field.
Disclosure of Invention
The invention solves the technical problem of overcoming the defects of complicated sample pretreatment, complex operation, dangerousness, long time consumption, low efficiency, high detection consumption, incapability of online real-time detection, high cost and the like in the analysis test of the nitro reduction reaction in the prior art, thereby providing the electrochemical method for online analyzing the nitro reduction reaction. The analysis method has the characteristics of real-time online detection, no need of central control sampling, good selectivity, high analysis speed and the like, and is simple to operate, convenient to maintain and low in detection cost.
The invention solves the technical problems through the following technical scheme:
the invention provides an electrochemical method for on-line analysis of nitro reduction reaction, which comprises the following steps:
(1) putting the mixed solution of polyelectrolyte and organic solvent into a dialysis membrane device;
(2) and (2) placing the working electrode, the counter electrode and the reference electrode in the dialysis membrane device in the step (1), then placing the dialysis membrane device in the nitro compound reaction solution, and then connecting an electrochemical system circuit, so that the nitro reduction reaction can be analyzed and detected.
In the step (1), the polyelectrolyte is a polyelectrolyte conventionally used in the field, and can be polystyrene sulfonic acid, polydiallyldimethylammonium chloride, polydiallylammonium chloride or polyethyleneimine, and the like, and can also be any composition of polymers with similar conductivity.
In the step (1), the organic solvent is an organic solvent conventionally used in the art, and the kind of the organic solvent is not particularly limited as long as the organic solvent does not react with the nitro compound and can dissolve the nitro compound, and may be, for example, methanol, ethanol, N-Dimethylformamide (DMF), Dimethylacetamide (DMAC), Tetrahydrofuran (THF), toluene-acetic acid, methanol-water, or the like, or a mixed solvent of the above organic solvents, preferably methanol, ethanol, N-Dimethylformamide (DMF), or Dimethylacetamide (DMAC).
In the step (1), the amount of the polyelectrolyte is the amount of the polyelectrolyte conventionally used in the art, the amount of the organic solvent is the amount of the organic solvent conventionally used in the art, and the amount of the polyelectrolyte and the amount of the organic solvent are not particularly limited as long as the organic solvent used can completely dissolve the polyelectrolyte, and preferably, the ratio of the amount of the polyelectrolyte to the amount of the organic solvent used is 8 to 12mg/mL, and more preferably 10 mg/mL.
In step (1), the operations and conditions for obtaining said mixed solution are those of mixing conventional in the art, preferably on a magnetic stirrer.
In step (1), the dialysis membrane device is a dialysis membrane device conventionally used in the art, and the dialysis membrane device may include a dialysis membrane, and a membrane support frame for supporting the dialysis membrane. As known to those skilled in the art, the membrane support frame has the function of preventing the dialysis membrane from deforming during the detection process so as to influence the detection result, and simultaneously, the diffusion of substances inside and outside the dialysis membrane is not influenced. The membrane support is not particularly limited as long as it does not react with the polyelectrolyte, the organic solvent, and the nitro compound reaction solution. Preferably, the membrane support frame is a mesh support or a hollow support. Preferably, the dialysis membrane device is a dialysis bag. The dialysis membrane of the dialysis membrane device is a dialysis membrane conventionally used in the art, preferably a dialysis membrane with molecular weight cut-off of 3500, 7000, 25000 or 50000, and also a dialysis membrane with higher molecular weight cut-off. In a preferred embodiment of the present invention, the dialysis membrane is a commercially available SPECTRUMLABS dialysis membrane, and the material thereof is RC membrane, i.e. regenerated cellulose membrane, and the specification includes dialysis bag MD34(25kD), dialysis bag MD31(3.5kD), etc.
In the step (2), the working electrode is a working electrode conventionally used in the field, and the working electrode can be various solid electrodes, such as a glassy carbon electrode, a gold electrode, a platinum disk microelectrode and the like; it is well known to those skilled in the art that the working electrode needs to be surface cleaned prior to use, preferably with 0.05 μm a-AL2O3Polishing the powder, cleaning with ultrapure water, and wiping to dry.
In the step (2), the counter electrode is a counter electrode conventionally used in the art, and the kind of the counter electrode is not particularly limited as long as the counter electrode does not undergo an oxidation-reduction reaction in an electrochemical system, and may be, for example, an inert metal, preferably platinum, gold, tungsten, or the like.
In step (2), the reference electrode is a reference electrode conventionally used in the art, preferably a saturated calomel electrode or a silver/silver chloride electrode.
In the step (2), the purpose of placing the dialysis membrane device in the nitro compound reaction solution is to make the nitro compound in the nitro compound reaction solution permeate the dialysis membrane, and certainly at the same time, the polyelectrolyte solution in the dialysis membrane does not permeate the dialysis membrane, so that the detection of the nitro compound is realized. The person skilled in the art knows that the detection of the nitro compound in the system of the dialysis membrane device can be started when the detection limit is reached, and in order to make the detection result more accurate, the detection result after the concentration of the substance to be detected in the system of the dialysis membrane device and the concentration of the nitro compound reaction solution reach equilibrium is generally selected as the final test result. The skilled in the art knows that there are several factors for achieving the concentration balance, such as temperature, stirring speed, cut-off molecular weight of dialysis membrane, etc., and generally the balance is achieved within 20-40 min.
In step (2), the electrochemical system circuit is an electrochemical system circuit conventionally used in the art, and a person skilled in the art knows that the working electrode, the counter electrode and the reference electrode are connected with an electrochemical workstation through a circuit, and an electrochemical data processing system is adopted for data acquisition and analysis. The voltage of the electrochemical system circuit is a voltage of an electrochemical system circuit which is conventional in the art, and is preferably-2.0 to 2.2V, more preferably-2.0 to 1.8V, and further more preferably 2.0 to 2.0V.
In the step (2), the nitro compound is a nitro compound conventionally used in the art, and preferably, the nitro compound includes an aromatic compound having one or more nitro groups on the aromatic ring, such as 2-methyl-5-nitrobenzenesulfonic acid, 2, 6-dimethylnitrobenzene, 4-chloro-3-nitrobenzylether, 2, 4-dichloro-5-isopropoxynitrobenzene, nitrotoluene, and the like. The nitro compound reaction liquid is a nitro compound reaction liquid which is conventional in the field.
On the basis of the common knowledge in the field, the above preferred conditions can be combined randomly to obtain the preferred embodiments of the invention.
The reagents and starting materials used in the present invention are commercially available.
The positive progress effects of the invention are as follows:
1. the dialysis membrane can be used for a long time and can be repeatedly utilized, so that the on-line analysis requirement of chemical production is realized.
2. The polyelectrolyte material is cheap and easy to obtain, the nitro compound has better electrochemical response in the electrolyte solution, and the electrolyte does not participate in the nitro reaction and does not change the reaction system of the nitro reduction reaction.
3. The on-line analysis method of the invention can also be conveniently and extensively applied to the rapid detection and analysis of other organic chemical reactions, such as self-reduction reaction of nitrogen-containing heterocycles, cyano-group reduction reaction, nitro-halogenation reaction and the like.
4. The material selected by the analysis method of the invention has low toxicity, the detection device of the nitro reduction reaction can be simplified, the detection process can be rapidly completed through the diffusion effect of the nitro compound on the microelectrode, and the feasibility of on-line monitoring of the organic reaction is greatly solved due to the combination of the two technologies which are applied to the electrochemical volt-ampere detection technology by the membrane technology.
Drawings
FIG. 1 is a schematic diagram of an electrochemical system circuit for nitro group reduction reaction in embodiments 1 to 7 of the present invention.
FIG. 2 is a voltammogram of multiple scans of 2, 6-dimethylnitrobenzene on a platinum disk microelectrode in example 1 of the present invention.
FIG. 3 is a voltammogram of multiple scans of 2-methyl-5-nitrobenzenesulfonic acid on a platinum disk microelectrode in example 2 of the present invention.
FIG. 4 is a voltammogram of multiple scans of 4-chloro-3-nitrobenzyl ether on a platinum disk microelectrode in example 3 of the present invention.
FIG. 5 is a voltammogram of multiple scans of 2, 4-dichloro-5-isopropoxynitrobenzene on a platinum disk microelectrode in example 4 of the present invention.
FIG. 6 electrochemical cyclic voltammogram of different concentrations of 4-chloro-3-nitrobenzyl ether (CMA) on platinum disk microelectrodes in example 5 of the present invention.
FIG. 7 is an electrochemical cyclic voltammogram of CMA control reaction solutions 1 (FIG. 7a) and 2 (FIG. 7b) on a platinum disk microelectrode in example 6 of the present invention.
FIG. 8 is a voltammogram of electrochemical cycles of nitrotoluene reduction reaction solutions on platinum disk microelectrodes in example 7 of the present invention.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
Example 1
(1) Adding 510mg of polydiallyl ammonium chloride into 50mL of DMMF (mixed liquid chromatography-mass transfer) to prepare a polyelectrolyte solution, and placing 3-5 mL of the polyelectrolyte solution into a dialysis membrane device, wherein the cut-off molecular weight of a dialysis membrane is 3500;
(2) the working electrode (platinum disk microelectrode) needs to be subjected to surface cleaning treatment before use, and 0.05 mu m of a-AL is utilized2O3Polishing the powder and then cleaning with ultrapure water; and wiping the mixture dry for later use.
(3) And (2) placing a working electrode (a platinum disk microelectrode), a counter electrode (a platinum wire) and a reference electrode (a silver/silver chloride electrode) in a dialysis membrane device in the step (1), connecting the working electrode and the 2, 6-dimethyl nitrobenzene reaction liquid (a solvent is DMF) to an electrochemical system circuit, setting a working voltage in a range of-2.0-1.8 v by using an electrochemical cyclic voltammetry, and analyzing and detecting the 2, 6-dimethyl nitrobenzene reaction liquid to obtain a cyclic voltammetry curve of the 2, 6-dimethyl nitrobenzene reaction liquid. The results are shown in FIG. 2.
Example 2
(1) Adding 490mg of polystyrene sulfonic acid into 50ml of methanol, mixing to prepare a polyelectrolyte solution, and putting 3-5 ml of the polyelectrolyte solution into a dialysis membrane device, wherein the cut-off molecular weight of a dialysis membrane is 7000;
(2) the working electrode (platinum disk microelectrode) needs to be subjected to surface cleaning treatment before use, and 0.05 mu m of a-AL is utilized2O3Polishing the powder and then cleaning with ultrapure water; and wiping the mixture dry for later use.
(3) And (2) placing a working electrode (a platinum disk microelectrode), a counter electrode (a tungsten wire) and a reference electrode (a saturated calomel electrode) in a dialysis membrane device in the step (1), connecting the working electrode and the 2-methyl-5-nitrobenzenesulfonic acid reaction liquid (a solvent is methanol) to an electrochemical system circuit, setting a working voltage in a range of-2.0 v by using an electrochemical cyclic voltammetry, and analyzing and detecting the 2-methyl-5-nitrobenzenesulfonic acid reaction liquid to obtain a cyclic voltammetry curve of the 2-methyl-5-nitrobenzenesulfonic acid reaction liquid. The results are shown in FIG. 3.
Example 3
(1) Adding 512mg of polydiallyl dimethyl ammonium chloride into 50ml of DMAC (dimethyl acetamide) to be mixed to prepare a polyelectrolyte solution, and placing 3-5 ml of the polyelectrolyte solution into a dialysis membrane device, wherein the cut-off molecular weight of the dialysis membrane is 50000;
(2) the working electrode (platinum disk microelectrode) needs to be subjected to surface cleaning treatment before use, and 0.05 mu m of a-AL is utilized2O3Polishing the powder and then cleaning with ultrapure water; and wiping the mixture dry for later use.
(3) And (2) placing a working electrode (a platinum disk microelectrode), a counter electrode (a tungsten wire) and a reference electrode (a silver/silver chloride electrode) in a dialysis membrane device in the step (1), connecting the working electrode and the 4-chloro-3-nitrobenzyl ether reaction liquid (a solvent is DMAC) to an electrochemical system circuit, setting a working voltage in a range of-2.0-1.8 v by using an electrochemical cyclic voltammetry, and analyzing and detecting the 4-chloro-3-nitrobenzyl ether reaction liquid to obtain a cyclic voltammetry curve of the 4-chloro-3-nitrobenzyl ether reaction liquid. The results are shown in FIG. 4.
Example 4
(1) Adding 505mg of polyethyleneimine into 50ml of ethanol, mixing to prepare a polyelectrolyte solution, and placing 3-5 ml of the polyelectrolyte solution into a dialysis membrane device, wherein the cut-off molecular weight of a dialysis membrane is 50000;
(2) the working electrode (platinum disk microelectrode) needs to be subjected to surface cleaning treatment before use, and 0.05 mu m of a-AL is utilized2O3Polishing the powder and then cleaning with ultrapure water; and wiping the mixture dry for later use.
(3) And (2) placing a working electrode (a platinum disk microelectrode), a counter electrode (a tungsten wire) and a reference electrode (a silver/silver chloride electrode) in a dialysis membrane device in the step (1), connecting the working electrode and the 2, 4-dichloro-5-isopropoxynitrobenzene reaction solution (the solvent is ethanol) to an electrochemical system circuit, setting the working voltage in a range of-2.0-1.8 v by using an electrochemical cyclic voltammetry, and analyzing and detecting the 2, 4-dichloro-5-isopropoxynitrobenzene reaction solution to obtain a cyclic voltammetry curve of the 2, 4-dichloro-5-isopropoxynitrobenzene reaction solution. The results are shown in FIG. 5.
Example 5
Preparing a standard solution of 4-chloro-3-nitrobenzyl ether (CMA), weighing 101.365mg of CMA standard substance, dissolving in a 10mL volumetric flask, dissolving with methanol and fixing the volume; as a standard stock solution. The dilution was stepwise to 1, 2, 3, 4, 6, 8 and 10mg/mL standard use solutions. The remaining operations and conditions were the same as in example 1. The results are shown in FIG. 6.
Example 6
Preparing a central control reaction solution of CMA, weighing 500-700 mg of a central control sample solution in a 10mL volumetric flask, dissolving with methanol and fixing the volume.
The above solutions were analyzed according to the procedure of example 1, respectively; a CMA calibration curve was obtained, and as shown in FIG. 7, the measured values of CMA in the CMA control reaction solutions 1 and 2 were calculated as contents by this curve, the area contents of which were 56.5% and 0%, respectively. The method for naming by the method can obtain accurate analysis results within 10 minutes.
Example 7
Electrolyte solution: weighing 1000mg of poly (diallyldimethylammonium chloride) into a 100mL volumetric flask, dissolving with methanol and fixing the volume; namely polyelectrolyte-methanol solution.
Nitrotoluene solution: 1200mg of nitrotoluene standard sample are weighed into a 10mL volumetric flask and dissolved with methanol.
Hydrochloric acid-methanol solution (1: 3): 50mL of 36% concentrated hydrochloric acid is added into 150mL of methanol and mixed evenly for later use.
The test method comprises the following steps:
adding a nitrotoluene methanol solution into a 150mL beaker, adding 100mL of a hydrochloric acid-methanol solution (1:3), stirring on a magnetic stirrer, then placing a three-electrode and dialysis bag device into the beaker, and adding 5mL of a supporting electrolyte solution into a dialysis bag; after the concentration of nitrotoluene in the solution in the dialysis membrane is close to that in the beaker, zinc powder (2650mg) is added, the zinc powder is slowly added, the nitroreduction reaction is started, cyclic voltammetry scanning is carried out within the range of-2.2V, and the voltammogram of the solution is recorded. The results are shown in FIG. 8. Until the scanning curves coincide, the reaction is shown to reach the end point.
As can be seen from the multiple scanning curves in FIGS. 2 to 5, the method of the present invention has good response stability. As can be seen from the scanning curve of FIG. 6, the method of the present invention has a good positive correlation between the response and the concentration in a certain concentration range. The remaining amount of the nitro compound can be judged by the size of the current peak (position indicated by arrow) in FIG. 7, and the larger the peak is, the more the nitro compound remains, indicating that the method of the present invention can accurately judge the remaining amount of the nitro compound in the reaction solution. As can be seen from the scanning curve in FIG. 8, the method of the present invention can accurately monitor the reaction condition of the nitro reduction reaction on line in real time.
While specific embodiments of the invention have been described above, it will be appreciated by those skilled in the art that this is by way of example only, and that the scope of the invention is defined by the appended claims. Various changes and modifications to these embodiments may be made by those skilled in the art without departing from the spirit and scope of the invention, and these changes and modifications are within the scope of the invention.
Claims (11)
1. An electrochemical method for on-line analysis of nitro-group reduction reaction, characterized in that it comprises the following steps:
(1) putting the mixed solution of polyelectrolyte and organic solvent into a dialysis membrane device;
(2) placing the working electrode, the counter electrode and the reference electrode in the dialysis membrane device in the step (1), then placing the dialysis membrane device in nitro compound reaction liquid, and then connecting an electrochemical system circuit, so that the nitro reduction reaction can be analyzed and detected; the polyelectrolyte is polydiallyl ammonium chloride, and the organic solvent is N, N-dimethylformamide; or the polyelectrolyte is polystyrene sulfonic acid, and the organic solvent is methanol; or the polyelectrolyte is polydiallyldimethylammonium chloride, and the organic solvent is dimethylacetamide; or the polyelectrolyte is polyethyleneimine, and the organic solvent is ethanol;
in the step (1), the dialysis membrane device comprises a dialysis membrane and a membrane support frame for supporting the dialysis membrane; the dialysis membrane is a regenerated cellulose membrane.
2. The electrochemical process of claim 1,
in the step (1), the ratio of the dosage of the polyelectrolyte to the dosage of the organic solvent is 8-12 mg/mL.
3. The electrochemical process of claim 1, wherein in step (1), the mixing of the mixed solution is performed on a magnetic stirrer.
4. The electrochemical method according to claim 1, wherein in the step (1), the ratio of the amount of the polyelectrolyte to the amount of the organic solvent is 10 mg/mL.
5. The electrochemical process of claim 3, wherein the dialysis membrane device is a dialysis bag;
the membrane support frame is a net-shaped support or a hollow support;
the cut-off molecular weight of the dialysis membrane is more than or equal to 3500.
6. The electrochemical process of claim 3, wherein the dialysis membrane has a molecular weight cut-off of 3500, 7000, 25000 or 50000.
7. The electrochemical process of claim 1, wherein in step (2), the working electrode is a glassy carbon electrode, a gold electrode, a platinum disk electrode, or a platinum disk microelectrode; the counter electrode is platinum, gold or tungsten; the reference electrode is a saturated calomel electrode or a silver/silver chloride electrode;
in the step (2), the working electrode is subjected to surface cleaning treatment before use;
in the step (2), the nitro compound is an aromatic compound containing one or more nitro groups on an aromatic ring;
in the step (2), the voltage of the electrochemical system circuit is-2.0-2.2V.
8. The electrochemical method of claim 7, wherein the surface cleaning treatment is with 0.05 μm α -Al2O3Polishing with powder, and purifying with pure waterCleaning and wiping.
9. The electrochemical process of claim 1, wherein in step (2), the nitro compound is nitrotoluene, 2, 6-dimethylnitrobenzene, 2-methyl-5-nitrobenzenesulfonic acid, 4-chloro-3-nitrobenzylether, or 2, 4-dichloro-5-isopropoxynitrobenzene.
10. The electrochemical method according to claim 1, wherein in the step (2), the voltage of the electrochemical system circuit is-2.0 to 1.8V.
11. The electrochemical method according to claim 1, wherein in the step (2), the voltage of the electrochemical system circuit is-2.0 to 2.0V.
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