JP2017186588A - Electroorganic synthesis apparatus and electroorganic synthesis method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an electroorganic synthesis apparatus and an electroorganic synthesis method in which a decrease in the yield of a target organic compound can be suppressed.SOLUTION: The electroorganic synthesis apparatus 1 comprises: a plurality of electrolysis cells 10U,10D, the cell 10U having an anode 11U and a cathode 12U which are arranged facing each other, the cell 10D having an anode 11D and a cathode 12D which are arranged facing each other; a power supply device 7 for applying a voltage between the anodes 11U and 11D and the cathodes 12D and 12U in the respective electrolysis cells 10U and 10D; and a pump 4 for circulating an electrolytic solution containing a halide ion and an organic compound between the anode 11D,11U and the cathode 12D,12U as a laminar flow state. The power supply device applies a voltage in which the polarity of the lower side anode 11D in the lower side electrolysis cell 10D and the polarity of the upper side cathode 12U in the upper side electrolysis cell 10U are opposed.SELECTED DRAWING: Figure 1

Description

  The present invention relates to an organic electrolytic synthesis apparatus and an organic electrolytic synthesis method.

  Conventionally, in an organic synthesis reaction, a solution containing a halide and an organic compound is electrolyzed and used to start the organic synthesis reaction. Such an organic synthesis reaction includes the introduction of a functional group into an organic compound, the production of an organic compound and derivative having a large molecular weight from a simple organic compound, the production of an organic halide and derivative, and an organometallic compound and derivative. This is used when manufacturing.

  In addition, as a reaction tank for performing the above organic synthesis reaction, a target organic compound is conventionally provided with a cathode and an anode in a reaction tank, and an electrolytic solution containing a reactant is circulated to oxidize an organic substance electrochemically. There exists an organic electrochemical reaction tank which manufactures (for example, refer patent document 1). This organic electrochemical reaction tank includes an electrode formed of a porous plate or a network structure plate. Electrolytic chambers partitioned by electrodes are formed on both sides of these electrodes at intervals suitable for the flow and electrolytic action of the electrolytic solution. The electrolytic solution fills the electrolytic chamber and crosses the inside of the liquid-permeable reaction electrode at right angles. It circulates to energize in the direction.

Japanese Patent Publication No. 2-44910

  However, in the reaction vessel disclosed in Patent Document 1, when an organic substance is oxidized, a peroxide or the like is produced in addition to a target organic compound that is a production purpose. By producing this peroxide or the like, the yield of the target organic compound may be reduced.

  The present invention has been made to solve the above-described problems, and an object thereof is to provide an organic electrolytic synthesis apparatus and an organic electrolytic synthesis method capable of suppressing a decrease in the yield of a target organic compound.

  According to the first aspect of the present invention, a plurality of electrolysis cells each having a first electrode and a second electrode disposed to face each other, and between the first electrode and the second electrode in the plurality of electrolysis cells. A power supply device that applies a voltage, and a flow device that circulates an electrolyte solution containing halide ions and an organic compound in a laminar flow state between the first electrode and the second electrode, the power supply device comprising: Of the upstream electrolysis cell and the downstream electrolysis cell arranged along the flow direction of the electrolyte, on the downstream side of the first electrode in the upstream electrolysis cell and the first electrode in the upstream electrolysis cell A voltage is applied so that the polarity of the second electrode in the arranged downstream electrolysis cell is opposite.

According to such a configuration, the electrolytic solution containing halide ions and the organic compound flows in a laminar flow state between the first electrode and the second electrode. For this reason, an oxidation reaction occurs at the first electrode to produce the target organic compound. Further, by-products such as peroxides other than the target organic compound are generated at the first electrode. If the target organic compound and the by-product stay in the electrolytic solution for a long time, the target organic compound and the by-product may react with each other, leading to a decrease in the yield of the target organic compound.
In this regard, in the above-described organic electrosynthesis apparatus, the downstream of the plurality of electrolytic cells is disposed downstream of the flow direction of the electrolytic solution of the first electrode that oxidizes and decomposes the electrolytic solution in the upstream electrolytic cell of the plurality of electrolytic cells. A second electrode of the side electrolysis cell is provided. Moreover, the electrolyte solution containing halide ions and organic compounds flows in a laminar flow state between the first electrode and the second electrode. For this reason, the by-product which generate | occur | produced in the 1st electrode of the upstream electrolysis cell is induced | guided | derived to the 2nd electrode of a downstream electrolysis cell by distribution | circulation of the electrolyte solution of a laminar flow state. The by-product induced to the second electrode is reduced by the second electrode and disappears. For this reason, since the reaction between the target organic compound and the by-product can be suppressed, a decrease in the yield of the target organic compound can be suppressed.

  In the above-described organic electrolytic synthesis apparatus, a plurality of the electrolytic cells may be provided along a direction intersecting with a flow direction of the electrolytic solution.

  According to such a configuration, since the electrolytic cells are arranged in directions other than the flowing direction of the electrolytic solution, a large amount of the electrolytic solution can be distributed in a short time. In addition, since the inner electrode disposed between the outer electrodes can function as a rectifying plate, it can contribute to the maintenance of a stable laminar flow.

  In the above-mentioned organic electrolytic synthesis apparatus, between the first electrode of the upstream electrolytic cell and the second electrode of the downstream electrolytic cell arranged side by side along the flow direction of the electrolytic solution, and the upstream An insulating spacer may be disposed between at least one of the second electrode of the side electrolysis cell and the first electrode of the downstream electrolysis cell.

According to such a configuration, since the spacer is disposed between the first electrode of the upstream electrolysis cell and the second electrode of the downstream electrolysis cell, the upstream electrolysis cell arranged in parallel in the flow direction of the electrolytic solution The gap between the electrode and the electrode of the downstream second electrolysis cell can be closed. For this reason, since generation | occurrence | production of the turbulent flow by a clearance gap can be suppressed, it can contribute to maintenance of the stable laminar flow. Moreover, since the spacer is insulative, the electrode of the upstream electrolysis cell and the electrode of the downstream electrolysis cell can be electrically insulated.
In addition, when the 1st electrode of a downstream electrolysis cell is provided in the distribution direction downstream of the electrolyte solution in the 2nd electrode of an upstream electrolysis cell, the 2nd electrode of an upstream electrolysis cell and a downstream electrolysis cell A spacer may be arranged between the first electrode. In this case as well, it is possible to contribute to maintaining a stable laminar flow and to suppress a short circuit between the electrode of the upstream electrolysis cell and the electrode of the downstream electrolysis cell.

  In the above-described organic electrolytic synthesis apparatus, the device includes a plurality of bipolar electrodes in which a part on one side in the flow direction of the electrolyte is the first electrode and a part on the other side is the second electrode. A plurality of electrode groups having electrodes arranged at intervals in the flow direction of the electrolyte solution are arranged in parallel to each other, and the bipolar electrodes of the electrode groups adjacent to each other in parallel are the first electrode The electrode and the second electrode may be arranged to face each other.

According to such a configuration, the device itself can be made compact by collectively arranging the bipolar electrodes having the first electrode and the second electrode.
Further, since the first electrode and the second electrode of the electrode groups adjacent to each other in parallel are opposed to each other, by energizing between the first electrode and the second electrode, the electrolyte flowing between the electrodes On the other hand, it is possible to efficiently perform electrolysis. The bipolar electrode can also function as a current plate.

  In the above organic electrosynthesis apparatus, the first electrode and the second electrode are plate-shaped and provided along the vertical direction, and the flow direction of the electrolytic solution may be a vertically upward direction. .

  According to such a configuration, since the electrolytic solution flows vertically upward, the contact time between the first electrode and the electrolytic solution can be increased. Therefore, the production amount of the target organic compound can be increased.

  In the organic electrolytic synthesis apparatus, the first electrode and the second electrode have a plate shape and are provided along a vertical direction, and a flow direction of the electrolytic solution intersects the vertical direction. Also good.

  According to such a configuration, the electrolytic solution can be distributed in a large amount in a short time.

  In the above organic electrolytic synthesis apparatus, a plurality of the electrolytic cells may be housed in a casing.

  According to such a configuration, the flow direction of the electrolytic solution can be regulated by the casing, which can contribute to the maintenance of a stable laminar flow. Moreover, the distribution | circulation of the electrolyte solution of the clearance gap between the electrode of the upstream electrolysis cell provided in the distribution direction of electrolyte solution and the electrode of a downstream electrolysis cell can be suppressed. Therefore, since generation | occurrence | production of the turbulent flow by a clearance gap can be suppressed, it can contribute to maintenance of the stable laminar flow.

  In the above organic electrolytic synthesis apparatus, an exhaust structure for discharging the gas in the casing may be formed on the upper portion of the casing.

  According to such a configuration, since the discharge of the gas in the casing can be promoted, the adhesion of the gas to the surface of the second electrode can be suppressed. Therefore, it is possible to suppress the reduction of by-products in the second electrode.

  In the organic electrolytic synthesis apparatus, a discharge mechanism that discharges the gas in the casing may be provided in a pipe that is connected to the casing and discharges the electrolytic solution from the casing.

  According to such a structure, it can respond | correspond widely to discharge | emission of the gas in a casing by various methods.

  The organic electrosynthesis apparatus may further include a speed control device that controls the speed of the electrolytic solution.

  According to such a configuration, since the flow rate of the electrolytic solution can be controlled, a stable laminar flow can be maintained.

  The organic electrosynthesis apparatus may further include a temperature control device that controls the temperature of the electrolytic solution.

  According to such a configuration, since the viscosity of the electrolytic solution can be controlled, a stable laminar flow can be maintained.

  According to the first aspect of the present invention, an organic electrolytic synthesis method produces a target organic compound by causing the electrolytic solution to flow between the first electrode and the second electrode in the organic electrolytic synthesis apparatus. To do.

  According to such a configuration, the electrolytic solution containing halide ions and the organic compound flows between the first electrode and the second electrode as a laminar flow state. For this reason, the by-product which generate | occur | produced in the 1st electrode of the upstream electrolysis cell is guide | induced to the 2nd electrode of a downstream electrolysis cell with the electrolyte solution of a laminar flow state. The by-product induced to the second electrode is reduced by the second electrode and disappears. For this reason, since the reaction between the target organic compound and the by-product can be suppressed, a decrease in the yield of the target organic compound can be suppressed.

  According to the organic electrolytic synthesis apparatus and the organic electrolytic synthesis method of the present invention, it is possible to suppress a decrease in the yield of the target organic compound.

It is a figure which shows typically the organic electrolytic synthesis apparatus in the 1st Embodiment of this invention. (A) is a figure which shows the flow of the by-product in the electrolysis cell arrange | positioned in the direction where an anode and a cathode cross | intersect with the distribution direction of electrolyte solution, (B) is a flow direction of electrolyte solution with an anode and a cathode. It is a figure which shows the flow of the by-product in the electrolysis cell arrange | positioned along. It is a figure which shows typically the principal part of the organic electrolytic synthesis apparatus in 2nd Embodiment. It is a figure which shows typically the principal part of the organic electrolytic synthesis apparatus in 3rd Embodiment. It is a figure which shows typically the principal part of the organic electrolytic synthesis apparatus in 4th Embodiment. It is a figure which shows typically the principal part of the organic electrolytic synthesis apparatus in 5th Embodiment. It is a block diagram of the organic electrolytic synthesis system in 6th Embodiment. It is a block diagram of the organic electrolytic synthesis system in a 1st modification. It is a block diagram of the organic electrolytic synthesis system in the 2nd modification. It is a perspective view of the electrolytic cell for demonstrating the formation conditions of a laminar flow.

  Embodiments to which the present invention is applied will be described below in detail with reference to the drawings. The drawings used in the following description are for explaining the configuration of the embodiment of the present invention, and the size, thickness, dimensions, etc. of each part shown in the figure are the dimensional relations of an actual organic electrolytic synthesis apparatus. May be different. Moreover, in each embodiment, about the common member, a common code | symbol is attached | subjected and the description may be abbreviate | omitted.

(First embodiment)
FIG. 1 is a diagram schematically showing an organic electrolytic synthesis apparatus according to the first embodiment of the present invention.
As shown in FIG. 1, the organic electrolytic synthesis apparatus 1 of the first embodiment includes an electrolytic cell 2, an inflow pipe 3A, an outflow pipe 3B, a pump 4, a heat exchanger 5, a power supply device 7, And a control device 8. The electrolytic cell 2 includes an electrolytic cell 10 and a casing 25. The casing 25 includes, as a plurality of electrolytic cells 10, a lower electrolytic cell 10D that is an upstream electrolytic cell and an upper electrolytic cell that is a downstream electrolytic cell. 10U is provided. The upper electrolysis cell 10U is juxtaposed above the lower electrolysis cell 10D. The lower electrolysis cell 10 </ b> D and the upper electrolysis cell 10 </ b> U are accommodated in a box-shaped casing 25.

The lower electrolysis cell 10D includes a lower anode 11D that is a first electrode and a lower cathode 12D that is a second electrode. The upper electrolysis cell 10U includes an upper anode 11U that is a first electrode and an upper cathode 12U that is a second electrode. The lower anode 11D, the lower cathode 12D, the upper anode 11U, and the upper cathode 12U all have a plate shape and are provided and arranged along the vertical direction. The lower anode 11D, the lower cathode 12D, the upper anode 11U, and the upper cathode 12U are all close to the side wall of the casing 25 and are disposed along the side wall of the casing 25. The distance between the lower anode 11D and the lower cathode 12D and the distance between the upper anode 11U and the upper cathode 12U are, for example, 1 to 30 mm.
An inlet 26 and an outlet 27 are formed in the casing 25. The inflow port 26 is formed on the lower side of the casing 25, and the outflow port 27 is formed on the upper side of the casing 25. Between the inflow port 26 and the outflow port 27, the lower electrolysis cell 10D and the upper electrolysis cell 10U are arranged.
One end of the inflow pipe 3 </ b> A is connected to the inflow port 26. The other end of the inflow pipe 3A is connected to a pump 4 which is a flow device and a flow rate control device. One end of the outflow pipe 3B is connected to the outflow port 27. The other end of the outflow pipe 3B is connected to a storage tank (not shown).

The pump 4 introduces an electrolytic solution into the casing 25 through the inflow pipe 3A. The electrolytic solution contains a halide containing a halide ion and an organic compound as a compound for producing the target organic compound. Further, the electrolytic solution contains a halide and an organic compound to a high concentration (a high concentration close to saturation).
The pump 4 suppresses the turbulent state of the electrolyte between the lower anode 11D and the lower cathode 12D of the lower electrolysis cell 10D and between the upper anode 11U and the upper cathode 12U of the upper electrolysis cell 10U. The electrolyte is circulated in a laminar flow state. The upper cathode 12U of the upper electrolysis cell 10U is disposed on the downstream side in the flow direction of the electrolyte in the lower anode 11D of the lower electrolysis cell 10D. In addition, the upper anode 11U of the upper electrolysis cell 10U is disposed on the downstream side in the flow direction of the electrolyte in the lower cathode 12D of the lower electrolysis cell 10D. Further, the flow direction of the electrolyte is a vertically upward direction, and the lower anode 11D and the upper cathode 12U, and the lower cathode 12D and the upper anode 11U are arranged in parallel in the flow direction of the electrolyte. The “laminar flow state” is a state in which turbulent flow is suppressed, for example, a state in which turbulent flow is minimized. Also, turbulent flow and laminar flow are the Reynolds number determined by the flow rate, viscosity, and flow path dimensions of the liquid (electrolyte), the distance between the electrodes arranged opposite to each other in the electrolytic cell, and the corresponding length determined by the electrode width. Although it changes as a boundary value, the “laminar flow state” here means a state having a Reynolds number of 2000 or less, which is usually defined by hydrodynamics.
The inflow pipe 3A is provided with a heat exchanger 5 which is a temperature control device. The heat exchanger 5 controls the temperature of the electrolyte flowing through the inflow pipe 3A. The viscosity of the electrolytic solution in the casing 25 varies with the temperature of the electrolytic solution introduced from the inflow pipe 3A.

The organic electrolytic synthesis apparatus 1 includes a power supply device 7 and a control device 8. The power supply device 7 includes a power supply 71 and a current control circuit 72. The power source 71 supplies a constant pressure current to the current control circuit 72.
The current control circuit 72 is electrically connected to the lower anode 11D, the lower cathode 12D, the upper anode 11U, and the upper cathode 12U. The current control circuit 72 supplies current to the lower anode 11D and the upper anode 11U, and receives current flowing out from the lower cathode 12D and the upper cathode 12U. Thus, the power supply device 7 applies a voltage having a reverse polarity between the lower anode 11D and the lower cathode 12D and between the upper anode 11U and the upper cathode 12U.
The current control circuit 72 adjusts the voltage of the constant pressure current supplied from the power supply 71 to an appropriate voltage when supplying current to the lower anode 11D and the upper anode 11U.

  The control device 8 includes a flow rate control unit 81 and a temperature control unit 82. The flow rate control unit 81 is electrically connected to the pump 4 and controls the output of the pump 4. The temperature control unit 82 is connected to the heat exchanger 5 and controls the output of the heat exchanger 5. By controlling the output of the pump 4, the speed of the electrolyte in the casing 25 is controlled. By controlling the output of the heat exchanger 5, the temperature is controlled so that the electrolyte supplied to the casing 25 and the viscosity of the electrolyte in the casing 25 are within a predetermined range.

Next, an example of producing azodicarbonamide as the target organic compound by the organic electrolytic synthesis method using the organic electrolytic synthesis apparatus 1 of the first embodiment will be described. In producing azodicarbonamide, the electrolyte contains a halide and an organic compound. Examples of halide ions constituting the halide include F ⁻ , Cl ⁻ , Br ⁻ and I ⁻ . Moreover, urea etc. can be illustrated as an organic compound.

An electrolytic solution containing a halide and an organic compound is circulated through the casing 25 by the pump 4. In the control device 8, the flow rate control unit 81 controls the output of the pump 4, and the temperature control unit 82 controls the output of the heat exchanger 5. Thus, the flow rate and temperature of the electrolyte in the casing 25 are controlled to maintain a laminar flow. The pump 4 is an example of the speed control device of the present invention.
At this time, the power supply device 7 supplies a current from the current control circuit 72 to the lower anode 11D and the upper anode 11U. The lower anode 11D of the lower electrolysis cell 10D electrolyzes an electrolytic solution containing a halide and an organic compound by anodic oxidation, and an organic synthesis reaction is started. This organic synthesis produces azodicarbonamide.
Furthermore, the upper anode 11U of the upper electrolysis cell 10U electrolyzes an electrolytic solution containing a halide and an organic compound by anodization to produce azodicarbonamide. The raw material container containing azodicarbonamide thus manufactured flows out from the outlet 27 of the casing 25 and is stored in the storage tank.

In the organic electrolytic synthesis apparatus 1 according to the first embodiment as described above, when an electrolytic solution containing a halide and an organic compound is anodized by the lower anode 11D in the production process of azodicarbonamide, the surface of the lower anode 11D The halide ions are oxidized to halogen alone (F ₂ , Cl ₂ , Br ₂ , I ₂ ) and peroxides (FO ⁻ , ClO ⁻ , BrO ⁻ , IO ⁻ ) to become by-products. By-products diffuse from the surface of the lower anode 11D into the electrolytic solution.
If by-products diffused in the electrolyte remain, unreacted organic compounds in the electrolyte and azodicarbonamide produced will be oxidatively decomposed by the by-products, leading to deterioration in the yield of azodicarbonamide. Yeah. Here, when the by-product in electrolyte solution lose | disappears, the deterioration of a yield is suppressed. In order to eliminate by-products in the electrolytic solution, there is a method in which a chemical agent for neutralizing halogen alone or peroxide is added to the electrolytic solution.
However, such a method of introducing a drug to eliminate by-products results in problems such as alteration of the properties of the electrolyte and an increase in the number of drugs used. Further, as a method for eliminating by-products, there is a method of reducing by-products at the cathode. For example, when the halogen is chlorine, the halide is reduced to a chloride ion by the following formula (1), and the peroxide ion is reduced to a chloride ion by the following formula (2).
Cl ₂ + 2e ⁻ → 2Cl ⁻ (1)
ClO ⁻ + H ₂ O + 2e ⁻ → Cl ⁻ + 2OH ⁻ (2)

Here, for example, as shown in FIG. 2A, an organic electrolytic synthesis apparatus including an anode 11X and a cathode 12X is assumed as the electrolytic cell 10X. In this organic electrosynthesis apparatus, it is assumed that there is almost no convection between the anode 11X and the cathode 12X, and the mass transfer until the by-product 18 reaches the cathode surface depends on natural diffusion. In this case, the contact time between the by-product 18 and the organic compound becomes long, and it becomes difficult to sufficiently obtain the effect of suppressing the oxidative decomposition of the target organic compound (azodicarbonamide).
In addition, since the electrolytic solution contains halide ions and organic compounds to a high concentration close to saturation, almost no natural material diffusion can be expected. On the other hand, if the by-product 18 is moved and diffused to the cathode surface by convection with the electrolytic solution, the contact time between the by-product 18 and the organic compound can be shortened.
However, the electrolytic solution flows in a direction orthogonal to the direction in which the anode 11X and the cathode 12X are separated from each other. For this reason, when the electrolytic solution is circulated in a laminar flow state, the by-product 18 is difficult to diffuse in the direction of the cathode 12X.
Further, when the electrolytic solution is circulated in a turbulent flow, the contact efficiency between the cathode 12X and the by-product 18 when the by-product 18 is moved from the anode 11X to the cathode 12X is improved, and the disappearance effect of the by-product 18 is improved. . However, when the electrolytic solution is circulated in a turbulent flow, the reaction field of the anode 11X is disturbed, the separation of the by-product 18 is promoted, and the contribution to the reduction of the by-product 18 remaining in the electrolytic solution is reduced. .

  In this regard, in the organic electrolytic synthesis apparatus 1 according to the first embodiment, since the electrolytic solution is circulated in a laminar flow state, the by-product 18 can be hardly separated into the electrolytic solution. Furthermore, in the organic electrolytic synthesis apparatus 1 according to the first embodiment, the upper anode 11U of the upper electrolytic cell 10U is arranged in parallel on the downstream side in the flow direction of the electrolytic solution in the lower anode 11D of the lower electrolytic cell 10D. For this reason, as shown in FIG. 2B, the by-product 18 generated in the lower anode 11D can be transported together with the target organic compound to the upper cathode 12U of the upper electrolysis cell 10U in a laminar flow state. Therefore, most of the by-products 18 generated in the lower anode 11D are reduced by the upper cathode 12U and disappear. Therefore, since the reaction between the target organic compound and the by-product 18 can be suppressed, a decrease in the yield of the target organic compound can be suppressed.

  Moreover, in the organic electrolysis synthesis apparatus 1 in the first embodiment, as a plurality of electrolysis cells, a lower electrolysis cell 10D and an upper electrolysis cell 10U arranged in parallel with each other are provided, and the flow direction of the electrolyte is The vertical upward direction. For this reason, it is possible to lengthen the contact time between the lower anode 11D and the upper anode 11U and the electrolytic solution. Therefore, the production amount of the target organic compound can be increased.

Further, the lower electrolysis cell 10 </ b> D and the upper electrolysis cell 10 </ b> U are accommodated in the casing 25. For this reason, since the distribution direction of electrolyte solution can be controlled with casing 25, it can contribute to maintenance of the stable laminar flow. In addition, it is possible to suppress the flow of the electrolytic solution in the gap between the lower anode 11D and the upper cathode 12U arranged in parallel in the flowing direction of the electrolytic solution and between the lower cathode 12D and the upper anode 11U. Therefore, generation of turbulent flow due to the gap between the lower anode 11D and the upper cathode 12U and between the lower cathode 12D and the upper anode 11U can be suppressed, which can contribute to the maintenance of a stable laminar flow. .
Furthermore, the lower anode 11 </ b> D, the lower cathode 12 </ b> D, the upper anode 11 </ b> U, and the upper cathode 12 </ b> U are all close to the side wall of the casing 25 and are disposed along the side wall of the casing 25. For this reason, generation | occurrence | production of the turbulent flow by the clearance gap between the lower anode 11D and the upper cathode 12U and between the lower anode 11D and the upper cathode 12U is further suppressed, and it contributes to the maintenance of the more stable laminar flow. Can do.

The conditions under which the electrolytic solution becomes a laminar flow are affected by the speed and viscosity of the electrolytic solution, the separation distance between the lower anode 11D and the lower cathode 12D, the separation distance between the upper anode 11U and the upper cathode 12U, and the like. . Since the separation distance between the lower anode 11D and the lower cathode 12D and the separation distance between the upper anode 11U and the upper cathode 12U are determined, the electrolyte solution is stabilized by adjusting the speed or viscosity of the electrolyte solution. It can be a flow state.
The organic electrolytic synthesizer 1 includes a pump 4 that causes the electrolytic solution to flow through the casing 25, and the speed of the electrolytic solution in the casing 25 can be controlled by the output of the pump 4. For this reason, the organic electrosynthesis apparatus 1 can maintain a stable laminar flow.
Further, the organic electrolytic synthesis apparatus 1 includes a heat exchanger 5, and the temperature of the electrolytic solution supplied to the casing 25 is controlled. When the temperature of the electrolytic solution is high, the viscosity of the electrolytic solution becomes low, and when the temperature of the electrolytic solution is low, the viscosity of the electrolytic solution becomes high. Thus, the viscosity of the electrolytic solution can be controlled by the temperature of the electrolytic solution. Therefore, the organic electrolytic synthesis apparatus 1 can control the temperature of the electrolytic solution by the heat exchanger 5 and can control the viscosity of the electrolytic solution by controlling the temperature. Therefore, the organic electrosynthesis apparatus 1 can maintain a stable laminar flow.

The reaction by electrolyzing an organic compound and halide ions is useful in that the halide ions can be recycled. When an electrolytic solution containing an organic compound and halide ions is electrolyzed, halide is generated from the anode. The target organic compound is contained therein, and other halides react while circulating in order to extract halide ions.
For example, when electrolytically synthesizing an azo compound, an electrolytic solution containing a carboamide compound and a halide ion (for example, chlorine ion) is electrolyzed to produce an intermediate of the halogen compound. A part of the produced halogen compound is taken out as a target organic compound (azo compound), and other halogen compounds react while circulating. The azo compound here includes azodicarbonamide and azodicarboxylic acid ester. Applications of these azo compounds are, for example, foaming agents and polymerization initiators.

  When an epoxy compound is electrolytically synthesized, an electrolytic solution containing an olefin and a halide ion (chlorine ion) is electrolyzed to produce an intermediate of the halogen compound. The intermediate of the halogen compound contains chlorine ions, and a part of the produced halogen compound is taken out as the target organic compound (epoxy compound). Other halogen compounds react while circulating to extract chlorine ions. The use of the epoxy compound here is, for example, an epoxy resin raw material.

  In addition, when electrolytically synthesizing a methoxy compound, for example, an electrolytic solution containing fluoroalkyl sulfide and methanol is electrolyzed to produce an intermediate of a halogen compound. The intermediate of the halogen compound contains fluorine ions, and a part of the produced halogen compound is taken out as the target organic compound (methoxylated fluoroalkyl sulfide). Other halogen compounds react while circulating to extract fluorine ions. Applications for methoxylated fluoroalkyl sulfides are, for example, pesticides.

  In the first embodiment, the target organic compound is azodicarbonamide, but other organic compounds may be used. Other target organic compounds may be azodicarboxylic acid esters and β-lactam derivatives.

In the first embodiment, the two electrolytic cells of the lower electrolytic cell 10D and the upper electrolytic cell 10U and four electrodes are provided, but more electrolytic cells and electrodes may be provided. For example, the anode and the cathode may be alternately arranged in series along the flow direction of the electrolytic solution, and the cathode and the anode facing the plurality of anodes and cathodes may be alternately arranged in series. Good.
In this case, an electrolysis cell is constituted by the cathode and anode facing each other, and a plurality of electrolysis cells are arranged in series along the flow direction of the electrolytic solution. Similarly, in the following embodiments, anodes and cathodes are alternately arranged in series along the flow direction of the electrolyte, and the cathodes and anodes facing these anodes and cathodes are arranged in series. Alternatively, they may be arranged alternately. Moreover, although the upper electrolysis cell 10U and the lower electrolysis cell 10D are accommodated in the casing 25, they may not be accommodated in the casing 25.

(Second Embodiment)
Next, a second embodiment of the present invention will be described. FIG. 3 is a diagram schematically illustrating a main part of the organic electrolytic synthesis apparatus according to the second embodiment. The organic electrolytic synthesizer in the second embodiment is mainly different from the organic electrolytic synthesizer in the first embodiment in the configuration of the electrolytic cell. Therefore, in FIG. 3, the second embodiment will be described with an electrolytic cell as the main part of the organic electrolytic synthesis apparatus.

  As shown in FIG. 3, the organic electrolytic synthesis apparatus 1B in the second embodiment includes an electrolytic cell 2B. The electrolytic cell 2B includes a casing 25B. The casing 25B includes a lower left anode 21DL, an upper middle anode 21UC, a lower right anode 21DR, an upper left cathode 22UL, a lower middle cathode 22DC, and an upper right cathode 22UR. Is provided. The lower left anode 21DL and the lower middle cathode 22DC constitute a lower left electrolysis cell 20DL, and the lower middle cathode 22DC and the lower right anode 21DR constitute a lower right electrolysis cell 20DR. The upper left electrolysis cell 20UL is composed of the upper left cathode 22UL and the upper middle anode 21UC, and the upper right electrolysis cell 20UR is composed of the upper middle anode 21UC and the upper right cathode 22UR.

The lower left anode 21DL, the upper middle anode 21UC, the lower right anode 21DR, the upper left cathode 22UL, the lower middle cathode 22DC, and the upper right cathode 22UR are all plate-shaped, and the power supply device 7 (see FIG. 1). ) Current control circuit 72.
A current is supplied from the current control circuit 72 to the lower left anode 21DL, the upper middle anode 21UC, and the lower right anode 21DR. A current flows out to the current control circuit 72 from the upper left cathode 22UL, the lower middle cathode 22DC, and the upper right cathode 22UR.

  An electrolyte containing a halide and an organic compound is supplied in a laminar flow state between the lower left anode 21DL and the lower middle cathode 22DC. Similarly, an electrolyte containing a halide and an organic compound is supplied in a laminar flow state between the lower middle cathode 22DC and the lower right anode 21DR. The flow directions of these electrolytes are all vertically upward. In the organic electrolytic synthesis apparatus 1B, the lower left electrolysis cell 20DL and the lower right electrolysis cell 20DR are provided as a plurality of electrolysis cells along a direction that intersects the flow direction of the electrolytic solution, for example, an orthogonal direction.

  In the organic electrosynthesis apparatus 1B according to the second embodiment, when the electrolyte is anodized by the lower left anode 21DL or the lower right anode 21DR in the casing 25B of the electrolytic cell 2B, the halogen alone or the peroxide is oxidized. And become a by-product. By-products are conveyed to the upper left cathode 22UL and the upper right cathode 22UR disposed downstream of the lower left anode 21DL and the lower right anode 21DR by the laminar electrolyte. Therefore, most of the by-products generated in the lower left anode 21DL and the lower right anode 21DR are reduced by the upper left cathode 22UL and the upper right cathode 22UR and disappear. Therefore, since the reaction between the target organic compound and the by-product can be suppressed, a decrease in the yield of the target organic compound can be suppressed.

  Moreover, in the organic electrolysis synthesis apparatus 1B in the second embodiment, the lower left electrolysis cell 20DL and the lower right electrolysis cell 20DR are provided as a plurality of electrolysis cells along a direction orthogonal to the flow direction of the electrolytic solution. Yes. For this reason, since the electrolytic cell is also arranged in a direction other than the flow direction of the electrolytic solution, a large amount of the electrolytic solution can be circulated in a short time. Moreover, it can respond also when an organic electrolytic synthesis apparatus enlarges. Further, the lower middle cathode 22DC is disposed between the lower left anode 21DL and the lower right anode 21DR, and the upper middle anode 21UC is disposed between the upper left cathode 22UL and the upper right cathode 22UR. For this reason, since the lower middle cathode 22DC and the upper middle anode 21UC can function as a rectifying plate, it is possible to contribute to maintaining a stable laminar flow. In addition to the lower middle cathode 22DC and the upper middle anode 21UC, for example, a conductive diaphragm may be provided for rectification.

(Third embodiment)
Next, a third embodiment of the present invention will be described. FIG. 4 is a diagram schematically illustrating a main part of the organic electrolytic synthesis apparatus according to the third embodiment. The organic electrolytic synthesizer in the third embodiment is mainly different from the organic electrolytic synthesizer in the first embodiment in the configuration of the electrolytic cell. In FIG. 4, a third embodiment will be described with an electrolytic cell as the main part of the organic electrolytic synthesis apparatus.

  As shown in FIG. 4, the organic electrolytic synthesis apparatus 1C in the third embodiment includes an electrolytic cell 2C. The electrolytic cell 2C includes a casing 25C, and the casing 25C is provided with a lower electrolysis cell 30D and an upper electrolysis cell 30U. The lower electrolysis cell 30D includes a lower anode 31D and a lower cathode 32D, and the upper electrolysis cell 30U includes an upper cathode 32U and an upper anode 31U. Further, the lower anode 31D and the upper cathode 32U, and the lower cathode 32D and the upper anode 31U each have a plate shape, and are arranged in parallel along the flowing direction of the electrolytic solution.

  A left spacer 33L is disposed between the lower anode 31D and the upper cathode 32U, and a right spacer 33R is disposed between the lower cathode 32D and the upper anode 31U. Both the left spacer 33L and the right spacer 33R are formed of an insulator. The inner surface of the casing 25 (see FIG. 1) in the lower anode 31D, the upper cathode 32U, and the left spacer 33L may have a level difference that can maintain a laminar flow state. There is no gap between the lower anode 31D, the upper cathode 32U, and the left spacer 33L, and the inner surface may have a level difference that can maintain a laminar flow state. Similarly, the inner surface of the casing 25 of the lower cathode 32D, the upper anode 31U, and the right spacer 33R may have a level difference enough to maintain a laminar flow state. There may be no gap between the lower cathode 32D, the upper anode 31U, and the right spacer 33R, and the inner surface may have a level difference that can maintain a laminar flow state.

  In the organic electrosynthesis apparatus 1C in the third embodiment, in the casing 25C of the electrolytic cell 2C, most of the by-products generated in the lower anode 31D are reduced by the upper cathode 32U and disappear. Therefore, since the reaction between the target organic compound and the by-product can be suppressed, a decrease in the yield of the target organic compound can be suppressed.

Further, in the organic electrolytic synthesis apparatus 1C according to the third embodiment, in the electrolytic cell 2C, the left spacer 33L is disposed between the lower anode 31D and the upper cathode 32U, and the lower cathode 32D and the upper anode 31U are arranged. A right spacer 33R is disposed therebetween. Therefore, the lower anode 31D and the upper cathode 32U, and the lower cathode 32D and the upper anode 31U can be mechanically integrated, and can be electrically insulated and separated. Therefore, it is possible to close a gap between the lower anode 31D and the upper cathode 32U and the lower cathode 32D and the upper anode 31U arranged in parallel in the flowing direction of the electrolyte. Therefore, since the generation of turbulent flow due to the gap can be suppressed, it is possible to contribute to maintaining a stable laminar flow.
The left spacer 33L and the right spacer 33R are both insulators. For this reason, it is possible to suppress the short circuit between the lower anode 31D and the upper cathode 32U and the short circuit between the lower cathode 32D and the upper anode 31U by electrically insulating them.

(Fourth embodiment)
Next, a fourth embodiment of the present invention will be described. FIG. 5 is a diagram schematically showing a main part of the organic electrolytic synthesis apparatus in the fourth embodiment. The organic electrolytic synthesizer in the fourth embodiment is mainly different from the organic electrolytic synthesizer in the first embodiment in the connection relationship between the electrolytic cell, the power supply device, and the electrodes. In FIG. 5, the fourth embodiment will be described by focusing on the connection relationship between the electrolytic cell, the power source, and the electrode as the main part of the organic electrolytic synthesis apparatus.

As shown in FIG. 5, the organic electrolytic synthesis apparatus 1D in the fourth embodiment includes an electrolytic cell 2D. The electrolytic cell 2D includes a casing 25D. The casing 25D is provided with a connection anode 41, a connection cathode 42, and a plurality of bipolar electrodes 43. The power supply device 7 is connected to the connection anode 41 and the connection cathode 42. The bipolar electrode 43 is a single plate-like electrode, and a portion on one side in the flow direction of the electrolyte is an anode and a portion on the other side is a cathode.
The organic electrolytic synthesis apparatus 1D includes a middle electrode group 44C in which a plurality of bipolar electrodes 43 are provided at intervals in the flow direction of the electrolytic solution. In addition, a left electrode group 44L and a right electrode group 44R are provided in which a connection anode 41, a connection cathode 42, and a plurality of bipolar electrodes 43 are provided at intervals in the flow direction of the electrolytic solution.

The bipolar electrode 43 in the left electrode group 44L and the bipolar electrode 43 in the middle electrode group 44C are arranged in a state shifted by about one-half pitch of the bipolar electrode 43 in the flowing direction of the electrolytic solution. . Thus, the bipolar electrode 43 in the left electrode group 44L and the bipolar electrode 43 in the middle electrode group 44C are arranged in a staggered manner. As a result, the downstream side in the flow direction of the electrolyte in the bipolar electrodes 43 adjacent in parallel to each other becomes the anode portion 43A, and the upstream side becomes the cathode portion 43B. Further, in the bipolar electrode 43 in the left electrode group 44L and the bipolar electrode 43 in the middle electrode group 44C, the anode part 43A and the cathode part 43B of the bipolar electrode 43 adjacent in parallel to each other are opposed to each other. In the left electrode group 44L, the connection cathode 42 is disposed on the most upstream side in the flow direction of the electrolytic solution, and the connection anode 41 is disposed on the most downstream side in the flow direction of the electrolytic solution.
Similarly, the bipolar electrode 43 in the middle electrode group 44C and the bipolar electrode 43 in the right electrode group 44R are arranged in a state shifted by about one-half pitch of the bipolar electrode 43 in the flow direction of the electrolytic solution. Has been. In the right electrode group 44R, the connection cathode 42 is disposed on the most upstream side in the flow direction of the electrolytic solution, and the connection anode 41 is disposed on the most downstream side in the flow direction of the electrolytic solution. In the organic electrolytic synthesis apparatus 1D, the anode portion 43A and the cathode portion 43B are arranged in this way, and the power supply device 7 is connected to the connection anode 41 and the connection cathode 42.

  In the organic electrosynthesis apparatus 1D according to the fourth embodiment, in the casing 25D of the electrolytic cell 2D, most of by-products generated in the anode portion 43A of the bipolar electrode 43 disposed on the upstream side in the flow direction of the electrolytic solution are electrolysis. It is reduced and disappears at the cathode portion 43B of the bipolar electrode 43 disposed on the downstream side in the liquid flow direction. Therefore, since the reaction between the target organic compound and the by-product can be suppressed, a decrease in the yield of the target organic compound can be suppressed.

  Further, in the organic electrolytic synthesis apparatus 1D according to the fourth embodiment, the plurality of bipolar electrodes 43 are collectively arranged by the left electrode group 44L, the middle electrode group 44C, and the right electrode group 44R. For this reason, the organic electrosynthesis apparatus 1D can be made compact. Further, since the anode part 43A and the cathode part 43B of the electrode groups adjacent to each other in parallel are opposed to each other, the connection anode 41 and the connection cathode 42 are connected to the power supply device 7, and between the anode part 43A and the cathode part 43B. By energizing the electrode, it is possible to efficiently electrolyze the electrolytic solution flowing between the electrodes.

In the adjacent electrode group, the bipolar electrode 43 is arranged in a state shifted by about one-half pitch of the bipolar electrode 43 in the flow direction of the electrolytic solution, and the power supply device 7 is connected to the connection anode 41 and the connection. Connected to the cathode 42. For this reason, a current flows by the polarization between the anode part 43A and the cathode part 43B of the bipolar electrode 43 between adjacent electrode groups. Accordingly, a voltage can be applied between the anode portion 43A and the cathode portion 43B of the bipolar electrode 43 without connecting the power supply device 7 to each of the plurality of bipolar electrodes 43. Can be made easier.
The bipolar electrode 43 can also function as a current plate.

(Fifth embodiment)
Next, a fifth embodiment of the present invention will be described. FIG. 6 is a perspective view schematically showing a main part of the organic electrolytic synthesis apparatus in the fifth embodiment. The organic electrolytic synthesis apparatus in the fifth embodiment is mainly different from the organic electrolytic synthesis apparatus in the first embodiment in the electrolytic cell. Further, in the fifth embodiment, the flow direction of the electrolytic solution is different from that of the first embodiment.

As shown in FIG. 6, the organic electrolytic synthesis apparatus 1E according to the fifth embodiment includes an electrolytic cell 2E. The electrolytic cell 2E includes a casing 25E. The casing 25E is provided with a left rear anode 51LB, a middle rear cathode 52CB, and a right rear anode 51RB arranged in parallel in the horizontal direction. The casing 25E is provided with a left middle cathode 52LC, a middle middle anode 51CC, and a right middle cathode 52RC arranged in parallel in the horizontal direction as a plurality of electrodes. Further, the casing 25E is provided with a left front anode 51LF, a middle front cathode 52CF, and a right front anode 51RF arranged in parallel in the horizontal direction. These electrodes have a plate shape and are provided and arranged along the vertical direction.
In the organic electrolytic synthesis apparatus 1E, the left rear anode 51LB and the left middle cathode 52LC are arranged side by side to constitute an electrolytic cell. Similarly, the middle rear cathode 52CB and the middle middle anode 51CC, and the right rear anode 51RB and the right middle cathode 52RC are arranged side by side to constitute an electrolytic cell. The left middle cathode 52LC and the left front anode 51LF, the middle middle anode 51CC and the middle front cathode 52CF, and the right middle cathode 52RC and the right front anode 51RF are arranged side by side to constitute an electrolytic cell.

  The electrolyte flows between the left rear anode 51LB and the left middle cathode 52LC, the middle rear cathode 52CB and the middle middle anode 51CC, and the right rear anode 51RB and the right middle cathode 52RC. Further, the electrolyte flows between the left middle cathode 52LC and the left front anode 51LF, the middle middle anode 51CC and the middle front cathode 52CF, and the right middle cathode 52RC and the right front anode 51RF. The flowing direction of the electrolytic solution is a direction intersecting the vertical direction, specifically, a horizontal direction. The plurality of electrolytic cells are juxtaposed in a direction orthogonal to the flow direction of the electrolytic solution. Further, the electrolytic solution is circulated in a laminar flow state.

  In the organic electrolytic synthesizer 1E according to the fifth embodiment, when the electrolyte is anodized with the left rear anode 51LB, the left front anode 51LF, and the middle / middle anode 51CC in the casing 25E of the electrolytic cell 2E, a halogen simple substance or peroxide is present. Oxidized as a by-product. By-products are the left rear anode 51LB, the left front anode 51LF, the middle rear cathode 52CB, the middle front cathode 52CF, the right middle cathode, which are arranged on the downstream side of the electrolyte flow direction in the left rear anode 51LB, the middle front anode 51CC. It is conveyed to 52RC. Therefore, most of the by-products generated in the left rear anode 51LB, the left front anode 51LF, and the middle middle anode 51CC are reduced by the middle rear cathode 52CB, the middle front cathode 52CF, and the right middle cathode 52RC and disappear. Therefore, since the reaction between the target organic compound and the by-product can be suppressed, a decrease in the yield of the target organic compound can be suppressed.

  Moreover, in the organic electrolytic synthesis apparatus 1E in the fifth embodiment, a plurality of anodes and cathodes are juxtaposed in the horizontal direction in the casing 25E. For this reason, many electrodes can be provided without arranging a plurality of electrodes in the height direction. Therefore, it is possible to distribute the electrolytic solution in a large amount in a short time. Moreover, since it is not necessary to make the flow path of electrolyte solution high in the height direction, it is possible to suppress an increase in the height of the organic electrosynthesis apparatus 1E. Furthermore, for example, the electrolyte solution pipe can be provided in-line in the middle of the horizontal pipe without being routed in the vertical direction.

(Sixth embodiment)
Next, a sixth embodiment of the present invention will be described. In the sixth embodiment, an organic electrolytic synthesis system including the organic electrolytic synthesis apparatus 1 shown in the first embodiment will be described. FIG. 7 is a configuration diagram of an organic electrolytic synthesis system in the sixth embodiment.
As shown in FIG. 7, the organic electrolytic synthesis system 100 according to the sixth embodiment includes a first electrolytic tank 2 </ b> X similar to the electrolytic tank 2 of the organic electrolytic synthesis apparatus 1 and a second electrolytic tank 2 </ b> Y.

One end of the inflow pipe 103 is connected to the inlet 101X of the first electrolytic cell 2X, and one end of the intermediate pipe 104 is connected to the outlet 102X of the first electrolytic cell 2X. The other end of the inflow pipe 103 is connected to the pump 105 so that the electrolytic solution can be introduced into the first casing 25X of the first electrolytic cell 2X.
The other end of the intermediate pipe 104 is connected to the inlet 101Y of the second electrolytic cell 2Y. One end of the outflow pipe 106 is connected to the outlet 102Y of the second electrolytic cell 2Y. The other end of the outflow pipe 106 is connected to a storage tank (not shown).

  The intermediate piping 104 disposed on the downstream side of the first electrolytic cell 2X is provided with a first gas vent valve 107 having an exhaust structure. The outflow pipe 106 arranged on the downstream side of the second electrolytic cell 2Y is provided with a second gas vent valve 108 that is an exhaust structure. The first gas vent valve 107 discharges the gas in the first casing 25X. The second gas vent valve 108 discharges the gas in the second casing 25Y of the second electrolytic cell 2Y. The inflow pipe 103 is provided with a heat exchanger 109.

In the organic electrolytic synthesis system 100 according to the sixth embodiment, the gas in the first casing 25X and the gas in the second casing 25Y are discharged. Here, the gas flow in the casing 25 of the organic electrolytic synthesis apparatus 1 shown in FIG. 1 will be described.
In the casing 25, hydrogen (H ₂ ) gas is generated from the lower cathode 12D and the upper cathode 12U along with the electrolysis of the electrolytic solution. For this reason, gas may accumulate in the casing 25. In particular, when the electrolysis time is long, such as when performing recycle electrolysis or when electrolysis is performed in which the electrolytic cell 2 is connected by a plug flow method, the H ₂ bubble ratio is remarkably increased. When the bubble rate increases, large bubbles are generated due to the accumulation of bubbles, which causes changes in flow velocity and pressure.
For this reason, the liquid flow of the electrolytic solution is generated toward a place where the bubble ratio is high. Therefore, when a place where the bubble ratio is locally high occurs, the electrolytic solution flows in an unexpected direction or the flow rate of the electrolytic solution is reduced. It may be premature. In such a case, it may be difficult to maintain the laminar flow of the electrolyte flowing through the lower electrolytic cell 10D and the upper electrolytic cell 10U. The same phenomenon can occur in the organic electrolytic synthesis apparatuses 1B to 1D in the second to fourth embodiments in addition to the organic electrolytic synthesis apparatus 1 in the first embodiment.

In order to eliminate such problems, the organic electrolytic synthesis system 100 enables the gas in the first casing 25X to be discharged by the first gas vent valve 107, and the gas in the second casing 25Y is discharged by the second gas vent valve 108. It can be discharged.
When the first gas vent valve 107 is closed, the intermediate pipe 104 is maintained in an airtight state. When the first gas vent valve 107 is opened, the intermediate pipe 104 is released from the airtight state, and the gas in the intermediate pipe 104 and the first casing 25X passes through the first gas vent valve 107 and the intermediate pipe 104 and the first casing 25X. Is discharged outside. Thus, gas accumulation in the first casing 25X can be suppressed, which can contribute to the maintenance of a laminar flow state of the electrolytic solution.

  When the second gas vent valve 108 is closed, the outflow pipe 106 is maintained in an airtight state. When the second vent valve 108 is opened, the outflow pipe 106 is released from the airtight state, and the gas in the outflow pipe 106 and the second casing 25Y passes through the second vent valve 108 and the outflow pipe 106 and the second casing 25Y. Is discharged outside. Thus, gas accumulation in the second casing 25Y can be suppressed, which can contribute to the maintenance of a laminar flow of the electrolytic solution.

  In addition, in the organic electrolytic synthesis system 100 in 6th Embodiment, although two electrolytic vessels are provided, it is good also as an organic electrolytic synthesis system provided with one electrolytic vessel. In this case, the inlet and outlet of the electrolytic cell may be connected by piping, and the electrolytic solution discharged from the electrolytic cell may be reacted while being returned to the same electrolytic cell and circulated.

(First modification)
Next, a first modification of the sixth embodiment will be described. FIG. 8 is a configuration diagram of the organic electrolytic synthesis system in the first modification.
As shown in FIG. 8, the organic electrolytic synthesis system 200 according to the first modification includes a first electrolytic cell 2X and a second electrolytic cell 2Y similar to the organic electrolytic synthesis system 100 according to the sixth embodiment. Yes.

One end of the inflow pipe 201 is connected to the inlet 101X of the first electrolytic cell 2X, and one end of the first intermediate pipe 202 is connected to the outlet 102X of the first electrolytic tank 2X. The other end of the inflow pipe 201 is connected to the pump 105 so that the electrolytic solution can be introduced into the first casing 25X of the first electrolytic cell 2X.
The other end of the first intermediate pipe 202 is connected to the inlet 203 </ b> A of the degassing storage tank 203. The degassing storage tank 203 stores the electrolytic solution conveyed through the first intermediate pipe 202. One end of the second intermediate pipe 204 is connected to the outlet 203 </ b> B of the storage tank 203.
The other end of the second intermediate pipe 204 is connected to the inlet 101Y of the second electrolytic cell 2Y. One end of the outflow pipe 205 is connected to the outlet 102Y of the second electrolytic cell 2Y. The other end of the outflow pipe 205 is connected to a storage tank (not shown).
A decompression mechanism 206 is provided at the upper end of the degassing storage tank 203. In the degassing storage tank 203, gas (gas) is stored above the stored electrolyte. The decompression mechanism 206 can adjust the pressure (atmospheric pressure) of the gas stored in the upper part of the degassing storage tank 203. By making the pressure in the degassing storage tank 203 higher than the atmospheric pressure by the decompression mechanism 206, the gas stored in the degassing storage tank 203 is discharged to the outside of the degassing storage tank 203.

  In the organic electrolytic synthesis system 200 in the first modified example, the pressure in the degassing storage tank 203 is increased by the decompression mechanism 206 so that the gas in the degassing storage tank 203 can be discharged. By setting the atmospheric pressure in the degassing storage tank 203 to be equal to or higher than the atmospheric pressure by the decompression mechanism 206, the gas in the degassing storage tank 203 can be forcibly discharged to the outside. The gas in the degassing storage tank 203 is discharged outside, and the gas in the first casing 25X is easily introduced into the degassing storage tank 203. Thus, gas accumulation in the first casing 25X can be suppressed, which can contribute to the maintenance of a laminar flow of the electrolytic solution.

  In addition, although the organic electrolytic synthesis system 200 in the first modification includes the first electrolytic tank 2X and the second electrolytic tank 2Y, the organic electrolytic synthesis system may include one first electrolytic tank 2X. In this case, the inlet 101X of the first electrolytic cell 2X and the outlet 203B of the degassing storage tank 203 are connected by piping, and the outlet 102X of the first electrolytic cell 2X and the inlet 203A of the degassing storage tank 203 are connected. You may make it react by making it connect with piping and returning the electrolyte solution discharged | emitted from the 1st electrolytic cell 2X to the 1st electrolytic cell 2X, and circulating.

(Second modification)
Next, a second modification of the sixth embodiment will be described. FIG. 9 is a configuration diagram of the organic electrolytic synthesis system in the second modification.
As shown in FIG. 9, the organic electrolytic synthesis system 300 in the second modified example includes an electrolytic cell 301 similar to the electrolytic cell 2E in the fifth actual mode. The electrolytic cell 301 includes a casing 302, and the casing 302 is provided with a plurality of anodes and cathodes. The plurality of anodes and cathodes are provided along the vertical direction with respect to the bottom plate of the casing 302.
The casing 302 includes an inlet 303 and an outlet 304. The outlet 304 is arranged at a position higher than the inlet 303. The casing 302 includes a bottom plate 305 and a top plate 306. The bottom plate 305 and the top plate 306 are provided substantially in parallel, and the bottom plate 305 is provided so as to be inclined with respect to a horizontal plane. For this reason, in the casing 302, electrolyte solution distribute | circulates diagonally upward. For this reason, the distribution direction of the electrolyte is an obliquely upward direction that intersects the vertical direction.
The plurality of anodes and cathodes are juxtaposed along the flow direction of the electrolytic solution, and the anodes and cathodes are alternately arranged. Further, a cathode and an anode are respectively provided at positions facing the anode and the cathode arranged side by side along the flow direction of the electrolytic solution.

  The top plate 306 of the casing 302 is provided with a first gas reservoir 307A to a third gas reservoir 307C and a first gas vent valve 308A to a third gas vent valve 308C. The first gas reservoir 307A is disposed upstream of the second gas reservoir 307B in the flow direction of the electrolyte solution, and the second gas reservoir 307B is disposed upstream of the third gas reservoir 307C in the flow direction of the electrolyte solution. Has been. The first gas vent valve 308A is provided in the first gas reservoir 307A. The second gas vent valve 308B is provided in the second gas reservoir 307B, and the third gas vent valve 308C is provided in the third gas reservoir 307C.

For example, when the electrolytic solution is circulated in the horizontal direction, the bubble rate increases with an increase in electrolysis time, and gas accumulation tends to occur between the electrodes. When a gas pool is generated between the electrodes, liquid level fluctuation occurs at the upper part between the electrodes, and the flow tends to become unstable. As a result, it becomes difficult to maintain the laminar flow. This problem also occurs when the electrolyte flows in a direction crossing the vertical direction, for example, in a diagonally upward direction as in the second modification.
In order to solve this problem, such liquid level fluctuation can be suppressed by eliminating the gas accumulation between the electrodes. In the organic electrolytic synthesis system according to the second modification, the first gas reservoir 307A to the third gas reservoir 307C and the first gas vent valve 308A to the third gas vent valve 308C are provided on the upper surface of the casing 302. The gas generated between the electrodes can be stored in the first gas reservoir 307A to the third gas reservoir 307C. Therefore, gas accumulation between electrodes can be eliminated, liquid level fluctuation can be suppressed, and a stable laminar flow can be maintained.

  Further, by opening the first gas vent valve 308A to the third gas vent valve 308C, the gas stored in the first gas reservoir 307A to the third gas reservoir 307C can be discharged to the outside of the casing 302. Therefore, even if the amount of gas stored in the first gas reservoir 307A to the third gas reservoir 307C increases, the first gas reservoir 307A is opened by opening the first gas vent valve 308A to the third gas vent valve 308C. ~ The amount of gas stored in the third gas reservoir 307C can be reduced. Therefore, gas accumulation between the electrodes can be preferably eliminated, liquid level fluctuation can be further suppressed, and a stable laminar flow can be maintained.

  The top plate 306 of the casing 302 is substantially parallel to the bottom plate 305 and is inclined with respect to the horizontal plane. For this reason, the gas that has floated up to the upper surface of the casing 302 moves, for example, along the upper surface of the casing 302 to the downstream side in the flow direction of the electrolyte. And finally, it is stored in the 3rd gas reservoir 307C arrange | positioned in the flow direction downstream of electrolyte solution, and is discharged | emitted outside the casing 302 by opening the 3rd gas vent valve 308C. For this reason, the residual of the gas in the casing 302 can be suppressed suitably.

(Conditions for laminar flow)
Next, conditions for forming a laminar flow state will be described. Here, the laminar flow state is a state where the Reynolds number Re is 2000 or less. Re = Lvρ / μ where Rei nozzle number Re is equivalent length L, liquid flow velocity v, liquid density ρ, liquid viscosity μ
It is represented by The equivalent length L is obtained from the interelectrode distance α between the anode 11 and the cathode 12 in the electrolytic cell 10, the electrode width β of the anode 11 (cathode 12), and the liquid flow velocity v.
The appropriate value of the Reynolds number Re in the laminar flow state varies depending on the reaction. When the reaction example shown in the example of producing azodicarbonamide as the target organic compound by the organic electrolytic synthesis method using the organic electrolytic synthesis apparatus 1 of the first embodiment is described, an appropriate Reynolds number that maintains high current efficiency Is 1-100.

The embodiment of the present invention has been described in detail with reference to the drawings. However, the specific configuration is not limited to this embodiment, and includes design changes and the like within a scope not departing from the gist of the present invention. .
Note that the above embodiments may be combined with each other. For example, a spacer as shown in the third embodiment is provided between the lower anode 11D and the upper cathode 12U shown in the first embodiment or the left rear anode 51LB and the middle rear cathode shown in the fifth embodiment. It may be disposed between the middle rear cathode 52CB and the right rear anode 51RB. Or you may provide the degassing storage tank provided with the decompression mechanism as shown in the 1st modification of 6th Embodiment in the organic electrosynthesis apparatus as shown in the 2nd modification.

1, 1B to 1E ... Organic electrolytic synthesizer 2, 2B to 2E ... Electrolysis tank 4 ... Pump (distribution device, speed control device)
5 ... Heat exchanger (temperature control device)
7 ... Power supply device 8 ... Control device 10D ... Lower electrolysis cell (upstream electrolysis cell)
10U ... Upper electrolysis cell (downstream electrolysis cell)
11D ... Lower anode (first electrode)
11U ... Upper anode (first electrode)
12D ... Lower cathode (second electrode)
12U ... Upper cathode (second electrode)
18 ... By-product 26 ... Inlet 22 ... Outlet 25, 25B-25E ... Casing 33L ... Left spacer (spacer)
33R ... Right spacer (spacer)
41 ... Connection anode 42 ... Connection cathode 43 ... Bipolar electrode (electrode group)
43A ... anode part (first electrode)
43B ... Cathode part (second electrode)
81 ... Flow rate control unit 82 ... Temperature control unit 100, 200, 300 ... Organic electrosynthesis system 107, 108, 308A-308C ... Valve (exhaust structure)

According to the first aspect of the present invention, a plurality of electrolysis cells each having a first electrode and a second electrode disposed to face each other, and between the first electrode and the second electrode in the plurality of electrolysis cells. A power supply device for applying a voltage; and a flow device for flowing an electrolyte solution containing halide ions and an organic compound between the first electrode and the second electrode in a laminar flow state, the first electrode And each of the second electrodes has a plate shape extending along a flow direction of the electrolytic solution, and the first electrode of the upstream electrolytic cell and the second electrode of the downstream electrolytic cell are formed of the electrolytic solution. The second electrode of the upstream electrolysis cell and the first electrode of the downstream electrolysis cell are arranged side by side along the flow direction of the electrolytic solution. cage, wherein the power supply of the electrolyte Of the upstream electrolysis cell and the downstream electrolysis cell arranged along the through direction, the first electrode in the upstream electrolysis cell and the downstream arranged in the downstream of the first electrode in the upstream electrolysis cell A voltage that is opposite to the polarity of the second electrode in the side electrolysis cell is applied.

Claims (12)

A plurality of electrolysis cells each comprising a first electrode and a second electrode disposed facing each other;
A power supply device for applying a voltage between the first electrode and the second electrode in a plurality of the electrolytic cells;
A flow device for flowing an electrolyte solution containing halide ions and an organic compound in a laminar flow state between the first electrode and the second electrode;
With
The power supply device includes: a first electrode in the upstream electrolysis cell and an first electrode in the upstream electrolysis cell among the upstream electrolysis cell and the downstream electrolysis cell arranged along the flow direction of the electrolyte. An organic electrolytic synthesizer, wherein a voltage that is opposite to the polarity of the second electrode in the downstream electrolysis cell disposed on the downstream side is applied.   The organic electrolytic synthesis apparatus according to claim 1, wherein a plurality of the electrolytic cells are provided along a direction that intersects a flow direction of the electrolytic solution.   Between the first electrode of the upstream electrolysis cell and the second electrode of the downstream electrolysis cell arranged side by side along the flow direction of the electrolyte, and the second electrode of the upstream electrolysis cell The organic electrolytic synthesis apparatus according to claim 1, wherein an insulating spacer is disposed between at least one of the first electrode and the first electrode of the downstream electrolytic cell. Including a plurality of bipolar electrodes in which a portion on one side in the flow direction of the electrolyte is the first electrode and a portion on the other side is the second electrode;
A plurality of electrode groups provided with these bipolar electrodes spaced apart in the flow direction of the electrolyte solution are arranged in parallel to each other,
The organic according to any one of claims 1 to 3, wherein the bipolar electrodes of the electrode groups adjacent to each other in parallel are arranged with the first electrode and the second electrode facing each other. Electrosynthesis device. The first electrode and the second electrode have a plate shape and are provided along the vertical direction,
The organic electrolytic synthesis apparatus according to claim 1, wherein a flow direction of the electrolytic solution is a vertically upward direction. The first electrode and the second electrode have a plate shape and are provided along the vertical direction,
The organic electrolytic synthesis apparatus according to claim 1, wherein a flow direction of the electrolytic solution is a direction intersecting a vertical direction.   The organic electrolysis synthesis apparatus according to any one of claims 1 to 6, wherein a plurality of the upstream electrolysis cells and the downstream electrolysis cells are accommodated in a casing.   The organic electrolytic synthesis apparatus according to claim 7, wherein an exhaust structure for discharging the gas in the casing is provided on an upper portion of the casing.   The organic electrolysis synthesis apparatus according to claim 7, wherein an exhaust structure that discharges the gas in the casing is provided in a pipe that is connected to the casing and from which the electrolytic solution is discharged.   The organic electrolytic synthesis apparatus according to claim 1, further comprising a speed control device that controls a speed of the electrolytic solution.   The organic electrolytic synthesis apparatus according to any one of claims 1 to 10, further comprising a temperature control device that controls a temperature of the electrolytic solution.   The target organic compound is produced by circulating the electrolytic solution between the first electrode and the second electrode in the organic electrolytic synthesis apparatus according to any one of claims 1 to 11. An organic electrolytic synthesis method.

Images