Apparatus for producing organic compounds and method for producing organic compounds

Abstract

The present invention provides an organic compound manufacturing apparatus that has a high effective current density and can carry out electrochemical reactions more efficiently. [Solution] An organic compound manufacturing apparatus comprising: an electrolytic cell having an anode section 4, a cathode section 5, and a solid polymer electrolyte membrane 3 disposed between the anode section 4 and the cathode section 5; an anode tank 6 for supplying anode solution to the anode section 4; a cathode tank 7 for supplying cathode solution to the cathode section 5; and an oil-water separator 12 for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode section 5 side through the solid polymer electrolyte membrane 3, reaction raw materials for the cathode solution, and organic compounds produced on the cathode section 5 side into an oil layer and an water layer, wherein the oil-water separator 12 is disposed (i) between supplying cathode solution from the cathode tank 7 to the cathode section 5, or (ii) between returning cathode solution from the cathode section 5 to the cathode tank 7.

Description

[Technical Field]

[0001] The present invention relates to an apparatus for producing organic compounds and a method for producing organic compounds. [Background technology]

[0002] Conventionally, an apparatus for producing organic compounds by electrochemical reaction is known, comprising an electrolytic cell having an anode electrode, a cathode electrode, and an electrolyte membrane disposed between the anode electrode and the cathode electrode; an anode tank for supplying anode solution to the anode electrode; and a cathode tank for supplying cathode solution to the cathode electrode.

[0003] For example, Patent Document 1 describes an organic hydride production apparatus comprising: an anode electrode that oxidizes water in an anode solution to generate protons; a cathode electrode that hydrogenates a hydrogenated substance in a cathode solution with the protons to generate an organic hydride; an electrolytic cell having a diaphragm disposed between the anode electrode and the cathode electrode to move the protons together with the associated water from the anode electrode side to the cathode electrode side; an anode solution supply unit that supplies the anode solution to the anode electrode; a water separation unit that separates the associated water from the cathode solution discharged from the cathode electrode; and a water return unit that sends the associated water separated by the water separation unit to the anode solution supply unit. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2022 / 118932 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] In the organic hydride production apparatus described in Patent Document 1, a water separation unit is provided to separate the associated water from the cathode liquid discharged from the cathode electrode by gravity sedimentation. The separated associated water is sent to an anode liquid supply unit and used as the anode liquid, and efforts have been made to improve operating efficiency. However, in Patent Document 1, there was room for further investigation into increasing the effective current density derived from the electrochemical reaction and carrying out the electrochemical reaction more efficiently.

[0006] Therefore, the object of the present invention is to provide an organic compound production apparatus and a method for producing organic compounds that have a high effective current density and can carry out electrochemical reactions more efficiently. [Means for solving the problem]

[0007] The inventors have found that the above problem can be solved by placing an oil-water separator at a predetermined location to separate an oil-water mixture containing an aqueous layer with associated water and an oil layer into an aqueous layer and an oil layer. In other words, the present invention provides the following [1] to [5]. [1] An electrolytic cell having an anode section, a cathode section, and a solid polymer electrolyte membrane disposed between the anode section and the cathode section; an anode tank for supplying anode solution to the anode section; a cathode tank for supplying cathode solution to the cathode section; and an oil-water separator for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode section through the solid polymer electrolyte membrane, reaction raw materials for the cathode solution, and organic compounds produced on the cathode section side into an oil layer and an water layer. An organic compound manufacturing apparatus, wherein the oil-water separator is positioned (i) between the supply of the cathode liquid from the cathode tank to the cathode section, or (ii) between the return of the cathode liquid from the cathode section to the cathode tank. [2] An electrolytic cell having an anode section, a cathode section, and a solid polymer electrolyte membrane disposed between the anode section and the cathode section; an anode tank for supplying anode solution to the anode section; a cathode tank for supplying cathode solution to the cathode section; and an oil-water separator for separating an oil-water mixture containing water derived from the cathode solution mixed into the anode section through the solid polymer electrolyte membrane, reaction raw materials for the anode solution, and organic compounds produced on the anode section side into an oil layer and an oil layer. An organic compound manufacturing apparatus, wherein the oil-water separator is positioned (iii) between supplying the anode liquid from the anode tank to the anode section, or (iv) between returning the anode liquid from the anode section to the anode tank. [3] An electrolytic cell having an anode section, a cathode section, and a solid polymer electrolyte membrane disposed between the anode section and the cathode section; an anode tank for supplying anode solution to the anode section; a cathode tank for supplying cathode solution to the cathode section; and an oil-water separator for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode section through the solid polymer electrolyte membrane, reaction raw materials for the cathode solution, and organic compounds produced on the cathode section side into an oil layer and an oil layer. A method for producing an organic compound, using an oil-water separator that is positioned (i) between the supply of the cathode liquid from the cathode tank to the cathode section, or (ii) between the return of the cathode liquid from the cathode section to the cathode tank. [4] An electrolytic cell having an anode section, a cathode section, and a solid polymer electrolyte membrane disposed between the anode section and the cathode section; an anode tank for supplying anode solution to the anode section; a cathode tank for supplying cathode solution to the cathode section; and an oil-water separator for separating an oil-water mixture containing water derived from the cathode solution mixed into the anode section through the solid polymer electrolyte membrane, reaction raw materials for the anode solution, and organic compounds produced on the anode section side into an oil layer and an oil layer. A method for producing an organic compound, using an oil-water separator that is positioned (iii) between supplying the anode liquid from the anode tank to the anode section, or (iv) between returning the anode liquid from the anode section to the anode tank. [5] An electrolytic cell having an anode section, a cathode section, and a solid polymer electrolyte membrane disposed between the anode section and the cathode section; an anode tank for supplying anode solution to the anode section; a cathode tank for supplying cathode solution to the cathode section; and an oil-water separator for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode section through the solid polymer electrolyte membrane, reaction raw materials for the cathode solution, and organic compounds produced on the cathode section side into an oil layer and an oil layer. A method for producing an organic compound, using an oil-water separator that is positioned (i) between supplying the cathode liquid from the cathode tank to the cathode section, or (ii) between returning the cathode liquid from the cathode section to the cathode tank, wherein the oil-water separator has a separation membrane that separates the oil-water mixture into an aqueous layer and an oil layer, and the organic compound produced on the cathode section side is a synthetic fragrance. [Effects of the Invention]

[0008] According to the present invention, an apparatus for producing organic compounds and a method for producing organic compounds are provided, which have a high effective current density and can carry out electrochemical reactions more efficiently. [Brief explanation of the drawing]

[0009] [Figure 1] This is a schematic diagram of an organic compound manufacturing apparatus according to the first embodiment of the present invention, in which the oil-water separator 12 is arranged in the position where (i) cathode liquid is supplied from the cathode tank 7 to the cathode section 5. [Figure 2] This is a schematic diagram of an organic compound manufacturing apparatus according to the first embodiment of the present invention, in which the oil-water separator 12 is arranged in the position between (ii) the cathode section 5 and the cathode liquid being returned to the cathode tank 7. [Figure 3]It is a schematic diagram of an organic compound manufacturing apparatus according to a second embodiment of the present invention, and the arrangement of the oil-water separator 12 is the arrangement during the supply of the anode liquid from the anode tank 6 to the anode part 4. [Figure 4] It is a schematic diagram of an organic compound manufacturing apparatus according to a second embodiment of the present invention, and the arrangement of the oil-water separator 12 is the arrangement during the return of the anode liquid from the anode part 4 to the anode tank 6. [Figure 5] It is a schematic diagram of an organic compound manufacturing apparatus not provided with an oil-water separator.

Embodiments for Carrying Out the Invention

[0010] The organic compound manufacturing apparatus according to the first embodiment of the present invention includes an electrolytic cell having an anode part, a cathode part, and a solid polymer electrolyte membrane disposed between the anode part and the cathode part, an anode tank for supplying an anode liquid to the anode part, a cathode tank for supplying a cathode liquid to the cathode part, and water derived from the anode liquid mixed into the cathode part side through the solid polymer electrolyte membrane, an oil-water separator for separating an oil-water mixture containing a reaction raw material of the cathode liquid and an organic compound generated on the cathode part side into an aqueous layer and an oil layer. The oil-water separator is arranged (i) during the supply of the cathode liquid from the cathode tank to the cathode part, or (ii) during the return of the cathode liquid from the cathode part to the cathode tank.

[0011] The organic compound manufacturing apparatus according to the second embodiment of the present invention includes an electrolytic cell having an anode part, a cathode part, and a solid polymer electrolyte membrane disposed between the anode part and the cathode part, an anode tank for supplying an anode liquid to the anode part, a cathode tank for supplying a cathode liquid to the cathode part, and water derived from the cathode liquid mixed into the anode part side through the solid polymer electrolyte membrane, an oil-water separator for separating an oil-water mixture containing a reaction raw material of the anode liquid and an organic compound generated on the anode part side into an aqueous layer and an oil layer. Place the oil-water separator (iii) during the supply of the anode liquid from the anode tank to the anode part or (iv) during the return of the anode liquid from the anode part to the anode tank.

[0012] According to the organic compound production apparatus according to the first and second embodiments of the present invention, there is an effect that the effective current density is high and the electrochemical reaction can be carried out more efficiently. The reason for this is not necessarily clear, but it is considered as follows. In the electrode reaction of the first embodiment shown in FIGS. 1 and 2, a part of the water contained in the anode liquid present on the anode part 4 side moves through the solid polymer electrolyte membrane 3 together with, for example, hydrogen ions generated on the anode part 4 side to the cathode electrode side and mixes into the cathode part 5 side. This water is referred to as "mixed water". In the first embodiment shown in FIGS. 1 and 2, the mixed water derived from the anode liquid mixed into the cathode part 5 side can be suitably removed by the oil-water separator 12 disposed at a predetermined position. Thus, since the amount of the mixed water present on the cathode part 5 side can be reduced, the frequency of contact between the reaction raw material of the cathode liquid and the catalyst increases, and the effective current density derived from the electrochemical reaction becomes high, and it is considered that the electrochemical reaction can be carried out more efficiently. Further, in the electrode reaction of the second embodiment shown in FIGS. 3 and 4, a part of the water contained in the cathode liquid present on the cathode part 5 side moves through the solid polymer electrolyte membrane 3 by, for example, osmotic pressure to the anode part 4 side and mixes into the anode part 4 side. This water is referred to as "mixed water". In the second embodiment shown in FIGS. 3 and 4, the mixed water derived from the cathode liquid mixed into the anode part 4 side can be suitably removed by the oil-water separator 12 disposed at a predetermined position. Thus, since the amount of the mixed water present on the anode part 4 side can be reduced, the frequency of contact between the reaction raw material of the anode liquid and the catalyst increases, and the effective current density derived from the electrochemical reaction becomes high, and it is considered that the electrochemical reaction can be carried out more efficiently. Note that the "mixed water" referred to in the above-described first and second embodiments may include water derived from the following. · Water diffused due to the concentration gradient of water between the anode part 4 and the cathode part 5 • Water moves due to osmotic pressure caused by the electrolyte concentration gradient. • Water that moves along with hydrogen ions as hydrogen ions move through the solid polymer electrolyte membrane 3. In this specification, "contaminated water in the first form" and "contaminated water in the second form" are collectively referred to simply as "contaminated water."

[0013] [Organic compound manufacturing equipment] Figure 1 is a schematic diagram showing an organic compound manufacturing apparatus according to the first embodiment of the present invention, in which the oil-water separator 12 is positioned (i) between the supply of cathode liquid from the cathode tank 7 to the cathode section 5 (also referred to as "pre-stage arrangement"). Figure 2 is a schematic diagram showing an organic compound manufacturing apparatus according to the first embodiment of the present invention, in which the oil-water separator 12 is positioned (ii) between the cathode section 5 and the cathode liquid being returned to the cathode tank 7 (also referred to as "retrograde positioning"). Figure 3 is a schematic diagram showing an organic compound manufacturing apparatus according to a second embodiment of the present invention, in which the oil-water separator 12 is positioned (iii) between the supply of anode liquid from the anode tank 6 to the anode section 4 (also referred to as "pre-stage arrangement"). Figure 4 is a schematic diagram showing an organic compound manufacturing apparatus according to a second embodiment of the present invention, in which the oil-water separator 12 is positioned between (iv) the return of the anode liquid from the anode section 4 to the anode tank 6 (also referred to as "retrograde positioning"). The first and second embodiments of the present invention will be described below in order.

[0014] [First Embodiment] As shown in Figures 1 and 2, the organic compound manufacturing apparatus according to the first embodiment of the present invention comprises an electrolytic cell having an anode section 4, a cathode section 5, and a solid polymer electrolyte membrane 3, an anode tank 6, a cathode tank 7, and an oil-water separator 12.

[0015] [Electrode reaction] The electrode reaction carried out in the electrolytic cell of the first embodiment is preferably a reduction reaction, and the case in which the reaction raw material of the cathode solution is an unsaturated hydrocarbon compound (R) is shown below as an example. <Anode electrode> H2O → 2H+ +2e - +1 / 2O2 <Cathode electrode> R+2H + +2e - →RH2

[0016] In the electrolytic cell of the first embodiment, on the anode electrode side of the anode section 4, water contained in the anode solution undergoes electrolysis to produce hydrogen ions, electrons, and oxygen. These hydrogen ions move to the cathode electrode side through the solid polymer electrolyte membrane 3. Meanwhile, on the cathode electrode side of the cathode section 5, a reduction reaction occurs in which the reaction raw material in the cathode solution (e.g., an unsaturated hydrocarbon compound (R)) accepts hydrogen ions and electrons that have moved to the cathode electrode side, and a desired organic compound, which is a reduction reaction product (e.g., a hydride (RH2)), is produced. The anode electrode consists of an anode catalyst layer 1a and an anode-side diffusion layer 1b. The cathode electrode consists of a cathode catalyst layer 2a and a cathode-side diffusion layer 2b.

[0017] Thus, in the electrode reaction of the first embodiment, the main reaction proceeds in which a desired organic compound, which is a reduction reaction product, is generated on the cathode electrode side. However, some of the water contained in the anode solution present on the anode portion 4 side moves to the cathode electrode side through the solid polymer electrolyte membrane 3, along with hydrogen ions generated on the anode portion 4 side, and mixes into the cathode portion 5 side. Here, the water originating from the anode solution that mixes into the cathode portion 5 side is referred to as "contaminated water" as described above. In the first embodiment of the present invention, contaminated water causes a decrease in the effective current density due to the electrochemical reaction. For this reason, an oil-water separator 12 is placed in a predetermined position to separate the oil-water mixture, which includes an aqueous layer containing contaminated water mixed into the cathode section 5 and an oil layer containing the reaction raw materials for the cathode liquid and the reduction reaction products generated on the cathode section 5, into an aqueous layer and an oil layer.

[0018] [Oil water separator] The oil-water separator 12 of the first embodiment shown in Figure 1 is (i) positioned between the cathode tank 7 and the cathode section 5 where the cathode liquid is supplied (also referred to as "pre-stage placement"). The oil-water separator 12 of the first embodiment shown in Figure 2 is (ii) positioned between the cathode section 5 and the cathode liquid returning to the cathode tank 7 (also referred to as "retrograde positioning"). The oil-water separator 12 of the first embodiment shown in Figures 1 and 2 has the function of separating an oil-water mixture, which includes water derived from the anode solution (contaminated water) that has been mixed into the cathode section 5 side through the solid polymer electrolyte membrane 3, and reaction raw materials of the cathode solution and organic compounds generated on the cathode section 5 side, into a water layer and an oil layer. The water layer containing the contaminated water separated by the oil-water separator 12 is returned to the anode tank 6. In the electrode reaction of the first embodiment, in addition to the generation of the desired organic compound, which is the reduction reaction product, in the cathode portion 5, hydrogen gas is also produced as a by-reaction. Therefore, the oil-water mixture after the electrode reaction also contains the by-product hydrogen gas. When the oil-water separator 12 is placed downstream, the oil-water separator separates the oil-water mixture immediately after the electrode reaction, so the concentration of hydrogen gas in the oil-water mixture is considered to be relatively high. On the other hand, when the oil-water separator 12 is placed upstream, the oil-water separator separates the oil-water mixture after it has passed through the cathode tank 7, so the concentration of hydrogen gas is considered to be relatively low as it is diluted by the cathode liquid. Therefore, in the first embodiment, the arrangement of the oil-water separator 12 is preferable when the oil-water separator 12 is placed in the preceding stage, because it is used to separate an oil-water mixture with a low hydrogen gas concentration, compared to when the oil-water separator 12 is placed in the subsequent stage.

[0019] The oil-water separator 12 of the first embodiment is not particularly limited as long as it is an oil-water separator capable of separating an oil-water mixture into a water layer and an oil layer. For example, the oil-water separator 12 may or may not be equipped with a separation membrane that can efficiently separate the oil-water mixture into a water layer and an oil layer. However, it is preferable that the oil-water separator 12 be equipped with a separation membrane, as this allows for the separation of the oil-water mixture into a water layer and an oil layer even when the difference in specific gravity between water and oil is relatively small, and also makes the organic compound manufacturing apparatus compact, making it suitable for the dispersion manufacturing of organic compounds. Examples of oil-water separators include the "SEP-10," "SEP-200-SS (Stainless Steel 316)," "SEP-200-HS (Hastelloy C276)," "SEP-200-FP (Perflourinated Polymers)," "SEP-3000-SS (Stainless Steel 316)," and "SEP-3000-HS (Hastelloy C276)" from ZaiptFlow Technologies. Furthermore, as separation membranes, for example, ZaiptFlowTechnologies' "OB-100-S10", "OB-400-S10", "OB-900-S10", "OB-2400-S10", "IL-200-S10", "IL-400-S10", "IL-900-S10", "IL-2000-S10", "OB-100-S200", "OB-400-S200", "OB-900-S200", "OB-24 Examples include "00-S200", "IL-200-S200", "IL-400-S200", "IL-900-S200", "IL-2000-S200", "OB-100-S3000", "OB-400-S3000", "OB-900-S3000", "OB-2400-S3000", "IL-200-S3000", "IL-400-S3000", "IL-900-S3000", and "IL-2000-S3000".

[0020] [Electrolytic cell] The electrolytic cell of the first embodiment comprises an anode section 4, a cathode section 5, and a solid polymer electrolyte membrane 3, as shown in Figures 1 and 2. The anode section 4 includes an anode electrode composed of an anode catalyst layer 1a and an anode-side diffusion layer 1b, and an anode chamber 1c. The cathode section 5 includes a cathode electrode composed of a cathode catalyst layer 2a and a cathode-side diffusion layer 2b, and a cathode chamber 2c.

[0021] <Anode electrode> The anode electrode (anode) is positioned so as to be in contact with one of the main surfaces of the solid polymer electrolyte membrane 3. The anode electrode consists of an anode catalyst layer 1a and an anode-side diffusion layer 1b, and is housed in the anode chamber 1c.

[0022] The anode catalyst layer 1a is positioned in contact with the solid polymer electrolyte membrane 3. The anode catalyst layer 1 is, for example, a layer containing a catalyst and a catalyst binder.

[0023] Examples of catalysts for the anode catalyst layer 1a include known catalysts used in anode catalyst layers, specifically metals such as iridium (Ir), ruthenium (Ru), platinum (Pt), palladium (Pd), and gold (Au), or alloys or composite metals containing these metals, or oxides containing these metals. The catalyst in the anode catalyst layer 1a may have a support, and examples of the support include titanium oxide (TiO2), porous carbon, and stainless steel.

[0024] Examples of catalyst binders for the anode catalyst layer 1a include known catalyst binders used in anode catalyst layers, specifically, perfluorocarbon sulfonic acid polymers such as "Nafion"; fluororesins such as polytetrafluoroethylene (PTFE), tetrafluoroethylene-hexafluoropropylene copolymer (FEP), and polyvinylidene fluoride (PVDF).

[0025] The anode-side diffusion layer 1b is positioned to be in contact with the side of the anode catalyst layer 1a opposite to the side in contact with the solid polymer electrolyte membrane 3. The anode-side diffusion layer 1b uniformly diffuses the anode liquid supplied from the anode tank 6 into the anode catalyst layer 1a. Examples of the anode-side diffusion layer 1b include known diffusion layers used in the anode catalyst layer, specifically, titanium metal sheets, carbon paper, carbon cloth, carbon felt, etc.

[0026] <Cathode electrode> The cathode electrode is positioned so as to be in contact with one of the main surfaces of the solid polymer electrolyte membrane 3. The cathode electrode consists of a cathode catalyst layer 2a and a cathode-side diffusion layer 2b, and is housed in a cathode chamber 2c.

[0027] The cathode catalyst layer 2a is positioned in contact with the solid polymer electrolyte membrane 3. The cathode catalyst layer 2a is, for example, a layer containing a catalyst and a catalyst binder.

[0028] Examples of catalysts for the cathode catalyst layer 2a include known catalysts used in cathode catalyst layers, specifically metals such as platinum (Pt), ruthenium (Ru), and palladium (Pd), or alloys of these metals. The catalyst in the cathode catalyst layer 2a may have a support, and examples of support include carbon such as carbon black powder, graphitized carbon, carbon fiber, and carbon nanotubes.

[0029] Examples of catalyst binders for the cathode catalyst layer 2a include known catalyst binders used in cathode catalyst layers, specifically, perfluorocarbon sulfonic acid polymers such as "Nafion"; fluororesins such as polytetrafluoroethylene (PTFE), tetrafluoroethylene-hexafluoropropylene copolymer (FEP), and polyvinylidene fluoride (PVDF).

[0030] The cathode-side diffusion layer 2b is positioned to be in contact with the side of the cathode catalyst layer 2a opposite to the side in contact with the solid polymer electrolyte membrane 3. The cathode-side diffusion layer 2b uniformly diffuses the cathode liquid supplied from the cathode tank 7 into the cathode catalyst layer 2a. Examples of cathode-side diffusion layers 2b include known diffusion layers used in cathode catalyst layers, specifically porous materials composed of carbon fibers such as carbon paper, carbon cloth, and carbon felt.

[0031] <Solid polymer electrolyte membrane> The solid polymer electrolyte membrane 3 is positioned between the anode portion 4 and the cathode portion 5. The solid polymer electrolyte membrane is preferably a proton exchange membrane. A proton exchange membrane (PEM) is a polymer membrane that selectively allows hydrogen ions (protons) to pass through. Proton exchange membranes are used in fuel cells, electrolytic devices, and other applications.

[0032] Examples of proton exchange membranes include: fluorine-based polymer electrolyte membranes made of perfluorocarbon sulfonic acid polymers such as "Nafion"; engineering plastic polymer electrolyte membranes such as sulfonated polyethersulfone and sulfonated polyetherketone; polymer electrolyte membranes made of polybenzimidazole impregnated with phosphoric acid or sulfuric acid; CSE (NEOSEPTA, containing sulfonated styrene copolymer, manufactured by Astrom Co., Ltd.), CMB (NEOSEPTA, containing sulfonated styrene-divinylbenzene copolymer, manufactured by Astrom Co., Ltd.), and CMVN (SELEMION). TM Examples include polymer electrolyte membranes made of sulfonated styrene polymers such as sulfonated divinylbenzene-styrene copolymer (manufactured by AGC Engineering Inc.).

[0033] It is preferable to arrange separators having grooves that serve as flow channels, numerous pores, etc., on both sides of the solid polymer electrolyte membrane 3. Examples of separators include metal separators, carbon separators, and separators made from various conductive materials such as a mixture of graphite and resin.

[0034] [Anode tank] The anode tank 6 is positioned in a location that allows the anode liquid to be supplied to the anode section 4.

[0035] [Anode liquid circulation channel] The anode tank 6 and the anode section 4 are connected by an anode liquid circulation channel 14. The anode liquid circulation channel 14 has an anode liquid supply channel 14a through which the anode liquid in the anode tank 6 passes when it moves toward the anode section 4, and an anode liquid return channel 14b through which the anode liquid in the anode section 4 passes toward the anode tank 6. For example, a pump 8 may be placed in the anode liquid supply channel 14a from the viewpoint of efficiently supplying the anode liquid in the anode tank 6 to the anode section 4. Alternatively, a heater 10 may be placed in the anode liquid supply channel 14a from the viewpoint of heating the anode liquid passing through the anode liquid supply channel 14a and appropriately raising the temperature of the mixed water to promote the separation of the water layer and the oil layer in the oil-water separator 12. The anode tank 6, anode section 4, pump 8, and heater 10 are connected, for example, by piping, and the anode liquid circulates between the anode tank 6 and the anode section 4 while passing through the aforementioned equipment and piping. Note that the location where the pump 8 or heater 10 is placed is not limited to the locations shown in Figures 1 and 2, and may be changed as needed.

[0036] <Anode solution> In the first embodiment, the anode solution is preferably one or more selected from ultrapure water, ion-exchanged water, and sulfuric acid aqueous solution, and more preferably one or more selected from ultrapure water and sulfuric acid aqueous solution.

[0037] In the first embodiment, the specific gravity of the reaction raw materials in the anode solution at 30°C is preferably 700 g / L or more, more preferably 800 g / L or more, even more preferably 900 g / L or more, and preferably 1,500 g / L or less, more preferably 1,300 g / L or less, and even more preferably 1,100 g / L or less.

[0038] [Cathode tank] The cathode tank 7 is positioned to allow the cathode liquid to be supplied to the cathode section 5.

[0039] [Cathode fluid circulation channel] The cathode tank 7 and the cathode section 5 are connected by a cathode liquid circulation channel 15. The cathode liquid circulation channel 15 has a cathode liquid supply channel 15a through which the cathode liquid in the cathode tank 7 passes when it moves toward the cathode section 5, and a cathode liquid return channel 15b through which the cathode liquid in the cathode section 5 passes when it moves toward the cathode tank 7. For example, a pump 9 may be placed in the cathode liquid supply channel 15a from the viewpoint of efficiently supplying the cathode liquid in the cathode tank 7 to the cathode section 5. In addition, a heater 11 may be placed in the cathode liquid supply channel 15a from the viewpoint of promoting the separation of the water layer and the oil layer in the oil-water separator 12 by heating the cathode liquid passing through the cathode liquid supply channel 15a. Furthermore, as described above, in the first embodiment, the oil-water separator 12 can be positioned in the preceding or succeeding stage. When the oil-water separator 12 is positioned in the preceding stage, it is located in the cathode liquid supply channel 15a (see Figure 1), and when the oil-water separator 12 is positioned in the succeeding stage, it is located in the cathode liquid return channel 15b (see Figure 2). The cathode tank 7, cathode section 5, oil-water separator 12, pump 9, and heater 11 are connected, for example, by piping, and the cathode liquid circulates between the cathode tank 7 and the cathode section 5 while passing through the aforementioned equipment and piping. Note that the location of the pump 9 or heater 11 is not limited to the locations shown in Figures 1 and 2, and may be changed as needed.

[0040] <Cathode solution> In the first embodiment, an oil-soluble organic compound is preferred as the reaction raw material for the cathode solution. In this specification, "oil-soluble organic compound" refers to an organic compound having a LogP value (the logarithm of the partition coefficient (P) between octanol and water of the compound), which is an indicator of hydrophobicity, greater than 0. As for oil-soluble organic compounds, reducible compounds are preferred, and among them, reducible compounds having an acetylene bond or an alkene bond, or reducible compounds having an aromatic ring are preferred, and reducible compounds having an aromatic ring are more preferred.

[0041] The reducible compound having an acetylene bond or an alkene bond may also be a compound having one or more functional groups selected from a nitrile group, an aldehyde group, a ketone group, a carboxyl group, an ester group, an imine group, an allyl group, and a nitro group.

[0042] Examples of reducible compounds having an aromatic ring include aromatic hydrocarbons, arylalkyl carboxylic acid esters, arylalkyl carboxylic acids, aryl-substituted aldehydes such as benzaldehyde, aryl-substituted unsaturated aldehydes, phenols, aryl-substituted alkanols, and nitrogen-containing heterocyclic aromatic compounds such as pyridines and pyrroles. Among these, from the viewpoint of improving the recovery rate during oil-water separation and carrying out electrochemical reactions more efficiently, one or more selected from arylalkyl carboxylic acid esters, aromatic hydrocarbons, aryl-substituted alkanols, and arylalkyl carboxylic acids are preferred. Furthermore, ethyl 2-phenylpropionate is preferred as the arylalkyl carboxylic acid ester. Toluene is preferred as the aromatic hydrocarbon. 1-(2-tert-butylphenyloxy)-2-butanol is preferred as the aryl-substituted alkanol. Furthermore, as reaction raw materials for the cathode solution, high value-added organic compounds are preferred from the viewpoint of achieving both high environmental value and high return on investment. Examples of high value-added organic compound raw materials include raw materials for synthetic fragrances, pharmaceutical raw materials, pharmaceutical intermediates, high boiling point industrial solvents, and raw materials for liquid organic hydrogen carriers. As for synthetic fragrance raw materials, one or more selected from ethyl 2-phenylpropionate, 1-(2-tert-butylphenyloxy)-2-butanol, 2-methylene undecanal, 2-cyclohexylacrylaldehyde, 3,6-dimethylhept-3-en-2-one, and 7-methylocta-4-en-3-one are preferred from the viewpoint of having a small difference in specific gravity with water and being able to easily exhibit the effects of the present invention. Examples of raw materials for pharmaceuticals, pharmaceutical intermediates, high-boiling-point industrial solvents, and liquid organic hydrogen carriers include naphthalene, p-nitrophenol, pyridine, and aniline.

[0043] In the first embodiment, the specific gravity of the reaction raw materials in the cathode solution is preferably 600 g / L or more, more preferably 700 g / L or more, even more preferably 800 g / L or more, and preferably 1,500 g / L or less, more preferably 1,300 g / L or less, and even more preferably 1,200 g / L or less.

[0044] In the first embodiment, the absolute value of the specific gravity difference between the reaction raw material derived from the anode solution and the reaction raw material from the cathode solution, and the absolute value of the specific gravity difference between the reaction raw material derived from the anode solution and the organic compound produced on the cathode 5 side, are preferably 200 g / L or less, more preferably 180 g / L or less, even more preferably 160 g / L or less, even more preferably 150 g / L or less, and even more preferably 140 g / L or less.

[0045] In the first embodiment, the temperature of the reaction raw materials for the anode solution and the cathode solution is preferably 0°C or higher, more preferably 20°C or higher, even more preferably 25°C or higher, and preferably less than 100°C, more preferably 80°C or lower, and even more preferably 70°C or lower.

[0046] Furthermore, when the temperature of the reaction raw materials in the anode solution, the temperature of the reaction raw materials in the cathode solution, and the temperature of the organic compound produced on the cathode side are all the same, the absolute value of the difference in specific gravity between the reaction raw materials derived from the anode solution and the reaction raw materials in the cathode solution, and the absolute value of the difference in specific gravity between the reaction raw materials derived from the anode solution and the organic compound produced on the cathode side are preferably 200 g / L or less, more preferably 180 g / L or less, even more preferably 160 g / L or less, even more preferably 150 g / L or less, and even more preferably 140 g / L or less.

[0047] [Reduction reaction products] Using the organic compound production apparatus according to the first embodiment, an oil-soluble organic compound, which is a reduction reaction product, can be produced by using the aforementioned reducible compound as a reaction raw material for the cathode solution. Examples of reduction reaction products include amines, alcohols, aldehydes, cycloalkyl carboxylic acid esters, alkylcycloalkanes, arylalkylaldehydes, cycloalkylaldehydes, aryl-substituted aldehydes, benzyl alcohol, phenylalkyl alcohol, cyclohexanol, and nitrogen-containing heterocyclic compounds such as piperidines and pyrrolidines. Among these, from the viewpoint of improving the recovery rate during oil-water separation and carrying out the electrochemical reaction more efficiently, one or more selected from cycloalkyl carboxylic acid esters and alkylcycloalkanes are preferred. Furthermore, cyclohexyl carboxylic acid esters are preferred as cycloalkyl carboxylic acid esters, and more specifically, ethyl 2-cyclohexylpropionate is more preferred. In addition, alkylcyclohexane is preferred as alkylcycloalkane, and methylcyclohexane is preferred as alkylcyclohexane.

[0048] [Second Embodiment] As shown in Figures 3 and 4, the organic compound manufacturing apparatus according to the second embodiment of the present invention comprises an electrolytic cell having an anode section 4, a cathode section 5, and a solid polymer electrolyte membrane 3, an anode tank 6, a cathode tank 7, and an oil-water separator 12, similar to the first embodiment.

[0049] 〔Electrode reaction〕 The electrode reaction carried out in the electrolytic cell of the second embodiment is preferably an oxidation reaction. Hereinafter, the case where the reaction raw material of the anolyte is alcohol (R-CH2-OH) will be taken as an example. <Anode electrode> R-CH2-OH → R-CHO + 2H + + 2e - <Cathode electrode> 2H + + 2e - → H2

[0050] In the electrolytic cell of the second embodiment, on the anode electrode side of the anode portion 4, an oxidation reaction occurs in which the reaction raw material of the anolyte (for example, alcohol (R-CH2-OH)) releases hydrogen ions and electrons, and a desired organic compound that is an oxidation reaction product (for example, aldehyde (R-CHO)) is generated. The hydrogen ions move to the cathode electrode side through the solid polymer electrolyte membrane 3. On the other hand, on the cathode electrode side of the cathode portion 5, hydrogen gas is generated from the hydrogen ions and electrons that have moved to the cathode electrode side. The anode electrode is composed of an anode catalyst layer 1a and an anode side diffusion layer 1b. The cathode electrode is composed of a cathode catalyst layer 2a and a cathode side diffusion layer 2b.

[0051] Thus, in the electrode reaction of the second embodiment, the reaction in which a desired organic compound that is an oxidation reaction product is generated on the anode electrode side proceeds as the main reaction. However, a part of the water contained in the catholyte present on the cathode portion 5 side moves to the anode electrode side through the solid polymer electrolyte membrane 3 and mixes into the anode portion 4 side, for example, due to osmotic pressure. Here, the water derived from the catholyte mixed into the anode portion 4 side is referred to as "mixed water" as described above. In the second embodiment of the present invention, contaminated water causes a decrease in the effective current density due to the electrochemical reaction. For this reason, an oil-water separator 12 is placed in a predetermined position to separate the oil-water mixture, which includes an aqueous layer containing contaminated water mixed into the anode 4 side and an oil layer containing the reaction raw materials of the anode solution and oxidation reaction products generated on the anode 4 side, into an aqueous layer and an oil layer.

[0052] [Oil water separator] The oil-water separator 12 of the second embodiment shown in Figure 3 is (iii) positioned between the supply of anode liquid from the anode tank 6 to the anode section 4 (also referred to as "pre-stage placement"). The oil-water separator 12 of the second embodiment shown in Figure 4 is positioned between (iv) the return of the anode liquid from the anode section 4 to the anode tank 6 (also referred to as "retrograde positioning"). The oil-water separator 12 of the second embodiment shown in Figures 3 and 4 has the function of separating an oil-water mixture, which includes water derived from the cathode solution (contaminated water) that has been mixed into the anode section 4 side through the solid polymer electrolyte membrane 3, and the reaction raw materials of the anode solution and organic compounds produced on the anode section 4 side, into a water layer and an oil layer. The water layer containing the contaminated water separated by the oil-water separator 12 is returned to the cathode tank 7. In the electrode reaction of the second embodiment, in addition to the production of the desired organic compound, which is an oxidation reaction product, in the main reaction on the anode portion 4 side, oxygen gas is also produced as a by-reaction. Therefore, the oil-water mixture after the electrode reaction also contains the by-produced oxygen gas. Furthermore, the "oxygen gas" produced as a by-reaction is thought to originate from the oxygen generated by the electrolysis described below from the contaminated water mixed into the anode 4. H2O → 2H + +2e - +1 / 2O2 When the oil-water separator 12 is placed downstream, the oil-water separator separates the oil-water mixture immediately after the electrode reaction, so the concentration of oxygen gas in the oil-water mixture is considered to be relatively high. On the other hand, when the oil-water separator 12 is placed upstream, the oil-water separator separates the oil-water mixture after it has passed through the anode tank 6, so the concentration of oxygen gas is considered to be relatively low as it is diluted by the anode solution. Therefore, in the second embodiment, the arrangement of the oil-water separator 12 is preferable when the oil-water separator 12 is placed in the preceding stage, because it is used to separate an oil-water mixture with a low oxygen gas concentration, compared to when the oil-water separator 12 is placed in the subsequent stage.

[0053] The oil-water separator 12 in the second embodiment is not particularly limited as long as it is a separator that can separate an oil-water mixture into a water layer and an oil layer, similar to the first embodiment. However, even when the difference in specific gravity between water and oil in the oil-water mixture is relatively small, it is preferable that the oil-water separator 12 is equipped with a separation membrane, as this allows for the separation of the oil-water mixture into a water layer and an oil layer, and also makes the organic compound manufacturing apparatus compact, making it suitable for the dispersion manufacturing of organic compounds.

[0054] [Electrolytic cell] As shown in Figures 3 and 4, the electrolytic cell of the second embodiment comprises an anode section 4, a cathode section 5, and a solid polymer electrolyte membrane 3, similar to the electrolytic cell of the first embodiment.

[0055] <Solid polymer electrolyte membrane> The solid polymer electrolyte membrane 3 is positioned between the anode portion 4 and the cathode portion 5, as in the first embodiment, and is preferably a proton exchange membrane, as in the first embodiment.

[0056] [Anode tank] The anode tank 6 is positioned in a location that allows the anode liquid to be supplied to the anode section 4, similar to the first embodiment.

[0057] [Anode liquid circulation channel] Similar to the first embodiment, the anode tank 6 and the anode section 4 are connected by an anode liquid circulation channel 14. The anode liquid circulation channel 14 has an anode liquid supply channel 14a through which the anode liquid in the anode tank 6 passes when it moves toward the anode section 4, and an anode liquid return channel 14b through which the anode liquid in the anode section 4 passes toward the anode tank 6. For example, a pump 8 may be placed in the anode liquid supply channel 14a from the viewpoint of efficiently supplying the anode liquid in the anode tank 6 to the anode section 4. In addition, a heater 10 may be placed in the anode liquid supply channel 14a from the viewpoint of promoting the separation of the water layer and the oil layer in the oil-water separator 12 by heating the anode liquid passing through the anode liquid supply channel 14a. Furthermore, as described above, in the second embodiment, the oil-water separator 12 can be positioned in the preceding or succeeding stage. When the oil-water separator 12 is positioned in the preceding stage, it is located in the anode liquid supply channel 14a (see Figure 3), and when the oil-water separator 12 is positioned in the succeeding stage, it is located in the anode liquid return channel 14b (see Figure 4). The anode tank 6, anode section 4, oil-water separator 12, pump 8, and heater 10 are connected, for example, by piping, and the anode liquid circulates between the anode tank 6 and the anode section 4 while passing through the aforementioned equipment and piping. Furthermore, the location where the pump 8 or heater 10 is placed is not limited to the locations shown in Figures 3 and 4, and may be changed as needed.

[0058] <Anode solution> In the second embodiment, an oil-soluble organic compound is preferred as the reaction raw material for the anode solution. As for oil-soluble organic compounds, oxidizable compounds are preferred. The oxidizable compound is preferably a compound having one or more functional groups selected from hydroxyl groups, aldehyde groups, ketone groups, ether groups, amine groups, thiol groups, and unsaturated hydrocarbon groups. Among these, from the viewpoint of improving the recovery rate when separating oil and water and carrying out electrochemical reactions more efficiently, a compound having one or more groups selected from hydroxyl groups, aldehyde groups, and ketone groups is preferred, and a compound having one or more groups selected from hydroxyl groups and aldehyde groups is more preferred. As the oxidizable compound used as the reaction raw material for the anode solution, one or more alcohols selected from primary alcohols, benzyl alcohol, and derivatives of benzyl alcohol are preferred. Examples of primary alcohols include 1-hexanol and 1-decanol. Derivatives of benzyl alcohol include 2-methylbenzyl alcohol, 4-methylbenzyl alcohol, 4-(dimethylamino)benzyl alcohol, and cinnamyl alcohol.

[0059] In the second embodiment, the specific gravity of the reaction raw materials in the anode solution at 30°C is preferably 600 g / L or more, more preferably 700 g / L or more, even more preferably 800 g / L or more, and preferably 1500 g / L or less, more preferably 1300 g / L or less, and even more preferably 1200 g / L or less.

[0060] [Cathode tank] The cathode tank 7 is positioned in a location that allows the cathode liquid to be supplied to the cathode section 5, similar to the first embodiment.

[0061] [Cathode fluid circulation channel] The cathode tank 7 and the cathode section 5 are connected by a cathode liquid circulation channel 15. The cathode liquid circulation channel 15 has a cathode liquid supply channel 15a through which the cathode liquid in the cathode tank 7 passes when it moves toward the cathode section 5, and a cathode liquid return channel 15b through which the cathode liquid in the cathode section 5 passes when it moves toward the cathode tank 7. For example, a pump 9 may be placed in the cathode liquid supply channel 15a from the viewpoint of efficiently supplying the cathode liquid in the cathode tank 7 to the cathode section 5. In addition, a heater 11 may be placed in the cathode liquid supply channel 15a from the viewpoint of appropriately raising the temperature of the mixed water by heating the cathode liquid passing through the cathode liquid supply channel 15a, thereby promoting the separation of the water layer and the oil layer in the oil-water separator 12. The cathode tank 7, cathode section 5, pump 9, and heater 11 are connected, for example, by piping, and the cathode fluid circulates between the cathode tank 7 and the cathode section 5 while passing through the aforementioned equipment and piping. Furthermore, the location where the pump 9 or heater 11 is placed is not limited to the locations shown in Figures 3 and 4, and may be changed as needed.

[0062] <Cathode solution> In the second embodiment, the cathode solution is preferably one or more selected from ultrapure water, ion-exchanged water, and sulfuric acid aqueous solution, and more preferably one or more selected from ultrapure water and sulfuric acid aqueous solution.

[0063] In the second embodiment, the specific gravity of the reaction raw materials of the cathode solution at 30°C is preferably 700 g / L or more, more preferably 800 g / L or more, even more preferably 900 g / L or more, and preferably 1500 g / L or less, more preferably 1300 g / L or less, and even more preferably 1100 g / L or less.

[0064] In the second embodiment, the absolute difference between the specific gravity of the reaction raw materials in the cathode solution at 30°C and the specific gravity of the reaction raw materials in the anode solution and / or the organic compound produced on the anode portion 4 side at 30°C is preferably 180 g / L or less, more preferably 160 g / L or less, even more preferably 150 g / L or less, and even more preferably 140 g / L or less.

[0065] [Oxidation reaction products] Using the organic compound production apparatus according to the second embodiment, an oil-soluble organic compound, which is an oxidation reaction product, can be produced by using the aforementioned oxidizable compound as a reaction raw material for the anode solution. Examples of oxidation reaction products include aldehydes, ketones, carboxylic acids, imines, peroxides, disulfides, and alcohols. Among these, from the viewpoint of improving the recovery rate during oil-water separation and carrying out the electrochemical reaction more efficiently, one or more selected from aldehydes, ketones, and carboxylic acids are preferred, and one or more selected from aldehydes and carboxylic acids are more preferred. When the oxidizable compound used as the reaction raw material in the anode solution is an alcohol, the resulting oxidation reaction product is an aldehyde. When the oxidizable compound is a primary alcohol, the oxidation reaction products obtained are hexanal, decanal, and the like. Furthermore, when the oxidizable compound is benzyl alcohol or cinnamyl alcohol, the oxidation reaction products obtained are benzaldehyde and cinnamaldehyde. Furthermore, when the oxidizable compound is a derivative of benzyl alcohol, the oxidation reaction products obtained include 2-methylbenzaldehyde, 4-methylbenzaldehyde, and 4-(dimethylamino)benzaldehyde.

[0066] The organic compound production apparatus of the present invention can be further modified to include various other forms in addition to the first and second embodiments described above. In the oil-water separator 12 of the first embodiment described above, as shown in Figures 1 and 2, the water layer containing the contaminated water separated by the oil-water separator 12 may be returned to the anode tank 6 and reused as anode liquid. Alternatively, the water layer containing the contaminated water separated by the oil-water separator 12 may be drained instead of being returned to the anode tank 6, and the anode tank 6 may be replenished with new anode liquid. Furthermore, a back pressure valve may be provided on the outlet side of the oil-water separator 12 to increase the flow rate as much as possible within the range in which oil-water separation is possible. These configurations can be arbitrarily selected. On the other hand, in the oil-water separator 12 of the second embodiment described above, as shown in Figures 3 and 4, the aqueous layer containing the contaminated water separated by the oil-water separator 12 may be returned to the cathode tank 7 and reused as cathode liquid. Alternatively, the aqueous layer containing the contaminated water separated by the oil-water separator 12 may be drained instead of being returned to the cathode tank 7, and the cathode tank 7 may be replenished with new cathode liquid. Furthermore, a back pressure valve may be provided on the outlet side of the oil-water separator 12 to increase the flow rate as much as possible within the range in which oil-water separation is possible. These configurations can be arbitrarily selected. [Examples]

[0067] The present invention will be specifically described below with reference to examples, but the present invention is not limited in any way by these examples.

[0068] Example 1 (1) Electrolytic cell As the electrolytic cell, a water electrolysis cell (manufactured by Eiwa Corporation) was used. The main specifications of the electrolytic cell are shown below. Separator material: Ti Separator flow path: vertical parallel flow path (flow path width 1 mm, flow path depth 1 mm, rib width 1 mm) Effective electrode area: 25 cm 2 For the electrodes, the following CCM (Catalyst Coated Membrane) was used, and the CCM and the diffusion layer were attached to the water electrolysis cell. <CCM (manufactured by Eiwa Corporation)> Solid polymer electrolyte membrane: Nafion N-117 Anode catalyst: IrO2 / TiO2 catalyst (IrO2 loading 1.0 mg / cm 2 ) Cathode catalyst: Pt / C catalyst (Pt loading 1.0 mg / cm 2 ) <Diffusion layer> Anode side diffusion layer: Metal titanium sheet (titanium fiber sintered body) (thickness 0.2 mm) Cathode side diffusion layer: Carbon paper (GDL22BB, manufactured by SGL Carbon)

[0069] (2) Experimental apparatus As the experimental apparatus, the apparatus shown in Fig. 1 was used. For the circulation supply of the anode liquid, an anode pump 8 (Q-100-TT-P-S, manufactured by Takumina Co., Ltd.) was used. For the circulation supply of the cathode liquid, a cathode pump 9 (Q-100-TT-P-S, manufactured by Takumina Co., Ltd.) was used. For heating the water electrolysis cell, a rubber heater attached to both sides of the cell was used. For applying voltage and measuring current, an electrochemical measurement device 13 (Hz-Pro, manufactured by Meiden Hokuto Corporation) was used. The electrochemical measurement device 13 was connected to the anode electrode and the cathode electrode of the electrolytic cell for measurement. Note that the anode electrode is composed of an anode catalyst layer 1a and an anode side diffusion layer 1b. Also, the cathode electrode is composed of a cathode catalyst layer 2a and a cathode side diffusion layer 2b. To separate the contaminating water contained in the cathode liquid discharged from the cathode section 5, an oil-water separator 12 was used, which combined a separator (SEP-10, manufactured by ZaiputFlowTechnologies) with a separation membrane (OB-900-S10, manufactured by ZaiputFlowTechnologies). In the apparatus shown in Figure 1, the oil-water separator 12 is positioned between the cathode tank 7 and the cathode section 5 where the cathode liquid is supplied (also referred to as "pre-stage placement").

[0070] (3) Experimental Procedure 50g of ultrapure water (specific gravity at 30°C: 995.65g / L), which is the anode solution, was placed in a 100mL glass container designated as anode tank 6, and 70g of ethyl 2-phenylpropionate (specific gravity at 30°C: 1000.7g / L), which is the reaction raw material for the cathode solution, was placed in a 100mL glass container designated as cathode solution tank 7. The anode liquid in the anode tank 6 was stirred with a magnetic stirrer, and the anode liquid flow rate was set to 5 mL / min using the anode pump 8. The anode liquid was then passed through the anode heater 10, its temperature controlled to 60°C, and circulated to the anode chamber 1c. Meanwhile, the cathode liquid in the cathode tank 7 was stirred with a magnetic stirrer, and the cathode liquid flow rate was set to 5 mL / min using the cathode pump 9. It was then passed through the cathode heater 11 to control the temperature to 30°C, and then passed through the oil-water separator 12 before being supplied to the cathode chamber 2c. Next, the hydrogenation reaction of ethyl 2-phenylpropionate, the reaction raw material of the cathode liquid supplied to the cathode section 5, was carried out. After that, the cathode liquid containing the contaminated water was returned to the cathode tank 7, passed through the cathode heater 11 to control the temperature to 30°C, and sent to the oil-water separator 12. There, the oil-water mixture containing the contaminated water was separated into the contaminated water and the oil layer. The contaminated water was sent to the anode tank 6, and the cathode liquid containing only the oil layer was circulated and supplied to the cathode section 5. Using the electrochemical measuring device 13, the potential difference between the cathode potential and the anode potential was controlled to 1.8V, and the hydrogenation reaction of ethyl 2-phenylpropionate was carried out for 5 hours to obtain ethyl 2-cyclohexylpropionate. Furthermore, even after mixing ethyl 2-phenylpropionate, the reaction raw material, with water in a 3:1 ratio and letting it stand for 2 hours, turbidity was observed in the oil layer, indicating insufficient layer separation and confirming that oil-water separation by gravity sedimentation was impossible. Similarly, after mixing ethyl 2-phenylpropionate, the reaction product, ethyl 2-cyclohexylpropionate, and water in a 297:3:100 ratio and letting it stand for 2 hours, turbidity was observed in the oil layer and multiple oil droplets were observed in the water layer, confirming that layer separation was insufficient and that oil-water separation by gravity sedimentation was impossible.

[0071] (4)Analysis At 0 hours, 1 hour, and 5 hours of the hydrogenation reaction of the cathode solution, the cathode solution returning to the cathode tank 7 was collected and its composition was analyzed using gas chromatography (GC). The effective current density i, which is the current density derived from the hydrogenation reaction of the cathode solution, was then calculated using the following formula. m The results for Example 1 are shown in Tables 1 and 2.

[0072]

number

[0073] i m Effective current density [mA / cm²] 2 ] y: Amount of hydride produced [mol] n: Number of reaction electrons [mol-e / mol] (In this example, the number of reaction electrons = 6 mol-e / mol in all cases) F: Faraday constant [C / mol] (=96,485 C / mol) t: reaction time [s] A: Electrode area [cm 2 (In this embodiment, the electrode area is 25 cm² in all cases.) 2 )

[0074] Example 2 The hydrogenation reaction of ethyl 2-phenylpropionate was carried out in the same manner as in Example 1, using the apparatus shown in Figure 2. Except for the fact that 160g of ultrapure water (specific gravity at 30°C: 995.65g / L), which is the anode solution, was placed in a 500mL glass container as anode tank 6, and 50g of ethyl 2-phenylpropionate (specific gravity at 30°C: 1000.7g / L), which is the reaction raw material for the cathode solution, was placed in a 250mL glass container as cathode tank 7, the hydrogenation reaction of ethyl 2-phenylpropionate was carried out in the same manner as in Example 1, to obtain ethyl 2-cyclohexylpropionate. In the apparatus shown in Figure 2, the oil-water separator 12 is positioned between the cathode section 5 and the cathode tank 7 where the cathode liquid is returned (also referred to as "retrograde placement"). In the apparatus shown in Figure 2, after the hydrogenation reaction of ethyl 2-phenylpropionate, which is the cathode solution supplied to the cathode electrode 2, the cathode solution containing contaminated water is sent to the oil-water separator 12, where it is separated into contaminated water and an oil layer. The contaminated water is sent to the anode tank 6, and the cathode solution containing only the oil layer is returned to the cathode tank 7. The results of Example 2 are shown in Tables 1 and 2.

[0075] Example 3 Using the apparatus shown in Figure 1, the hydrogenation reaction of toluene was carried out in the same manner as in Example 1, except that ethyl 2-phenylpropionate, the reaction raw material for the cathode solution, was replaced with toluene (specific gravity at 30°C: 857.5 g / L), and 47 g of ultrapure water was added as the anode solution and 45 g of toluene was added as the reaction raw material for the cathode solution. Cyclohexane was obtained. Furthermore, when toluene and water were mixed in a 3:1 ratio and allowed to stand for 30 seconds, both the oil layer and the water layer were clear, confirming that oil-water separation by gravity sedimentation is possible. The results of Example 3 are shown in Tables 1 and 2.

[0076] Example 4 As the experimental apparatus, a 200 mL glass container was used as the anode tank 6 in the apparatus shown in Figure 2. The hydrogenation reaction of toluene was carried out in the same procedure as in Example 3, except that 48 g of ultrapure water, the reaction raw material for the anode solution, and 47 g of toluene, the reaction raw material for the cathode solution, were charged. Methylcyclohexane was obtained. The results of Example 4 are shown in Table 2.

[0077] Comparative Example 1 The hydrogenation reaction of ethyl 2-phenylpropionate was carried out in the same manner as in Example 1, using the apparatus shown in Figure 5, except that 49 g of ultrapure water, the reaction raw material for the anode solution, and 48 g of ethyl 2-phenylpropionate, the reaction raw material for the cathode solution, were charged to obtain ethyl 2-cyclohexylpropionate. In the apparatus shown in Figure 5, the oil-water separator 12 was not provided. After the hydrogenation reaction of ethyl 2-phenylpropionate, the reaction raw material for the cathode liquid supplied from the cathode tank 7 to the cathode section 5, the oil-water mixture containing contaminated water was returned directly to the cathode tank 7. The results of Comparative Example 1 are shown in Table 1.

[0078] Comparative Example 2 The apparatus shown in Figure 5 was used for the experiment. Except for charging 48g of ultrapure water as the anode solution and 48g of toluene as the reaction raw material for the cathode solution, the hydrogenation reaction of toluene was carried out in the same procedure as in Example 3 to obtain methylcyclohexane. The results of Comparative Example 2 are shown in Table 1.

[0079] [Table 1]

[0080] The following was confirmed from the results in Table 1. Examples 1 and 2, and Comparative Example 1, are examples in which ethyl 2-phenylpropionate was used as the reaction raw material for the cathode solution. Examples 1 and 2, which are equipped with an oil-water separator 12 in a predetermined position, were found to have a higher effective current density and be capable of efficiently carrying out the hydrogenation reaction compared to Comparative Example 1, which is not equipped with an oil-water separator 12. On the other hand, Example 3 and Comparative Example 2 are examples in which toluene was used as the reaction raw material for the cathode solution. Example 3, which includes an oil-water separator 12 in a predetermined position, was found to have a higher effective current density and be a device capable of efficiently carrying out the hydrogenation reaction compared to Comparative Example 2, which does not include an oil-water separator 12.

[0081] [Table 2]

[0082] The following was confirmed from the results in Table 2. Examples 1 and 2 are examples in which ethyl 2-phenylpropionate was used as the reaction raw material for the cathode solution. It was confirmed that Example 1, in which the oil-water separator 12 is placed in the preceding stage, has a higher effective current density and can carry out the hydrogenation reaction more efficiently compared to Example 2, in which the oil-water separator 12 is placed in the subsequent stage. Examples 3 and 4 are examples in which toluene was used as the reaction raw material for the cathode solution. In Example 3, where the oil-water separator 12 is placed in the preceding stage, it was confirmed that the apparatus has a higher effective current density and can carry out the hydrogenation reaction more efficiently compared to Example 4, where the oil-water separator 12 is placed in the subsequent stage. [Explanation of Symbols]

[0083] 1a Anode catalyst layer 1b Anode-side diffusion layer 1c Anode Chamber 2a Cathode catalyst layer 2b Cathode-side diffusion layer 2c Cathode Chamber 3 Solid polymer electrolyte membrane 4 Anode section 5. Cathode section 6 Anode tank 7 Cathode Tank 8 Anode pumps 9. Cathode pump 10 Anode heaters 11 Cathode Heater 12 Oil-water separator 13 Electrochemical measuring device 14 Anode liquid circulation channel 14a Anode liquid supply channel 14b Anode liquid return channel 15 Cathode fluid circulation channel 15a Cathode liquid supply channel 15b Cathode liquid return channel [Industrial applicability]

[0084] According to the present invention, an apparatus for producing organic compounds and a method for producing organic compounds are provided, which have a high effective current density and can carry out electrochemical reactions more efficiently.

Claims

1. An electrolytic cell having an anode portion, a cathode portion, and a solid polymer electrolyte membrane disposed between the anode portion and the cathode portion, an anode tank for supplying anode liquid to the anode portion, A cathode tank for supplying cathode liquid to the cathode section, An oil-water separator separates an oil-water mixture containing water derived from the anode solution that has been mixed into the cathode side through the solid polymer electrolyte membrane, the reaction raw materials of the cathode solution, and organic compounds produced on the cathode side into an oil layer and an oil layer. Equipped with, The oil-water separator is positioned (i) between supplying the cathode liquid from the cathode tank to the cathode section, or (ii) between returning the cathode liquid from the cathode section to the cathode tank. Organic compound manufacturing equipment.

2. An electrolytic cell having an anode portion, a cathode portion, and a solid polymer electrolyte membrane disposed between the anode portion and the cathode portion, an anode tank for supplying anode liquid to the anode portion, A cathode tank for supplying cathode liquid to the cathode section, An oil-water separator separates an oil-water mixture containing water derived from the cathode solution mixed into the anode portion through the solid polymer electrolyte membrane, the reaction raw materials of the anode solution, and organic compounds produced on the anode portion into an oil layer and an oil layer. Equipped with, The oil-water separator is positioned (iii) between supplying the anode liquid from the anode tank to the anode section, or (iv) between returning the anode liquid from the anode section to the anode tank. Organic compound manufacturing equipment.

3. The organic compound production apparatus according to claim 1 or 2, wherein the oil-water separator has a separation membrane that separates the oil-water mixture into an aqueous layer and an oil layer.

4. The organic compound manufacturing apparatus according to claim 1 or 2, wherein the solid polymer electrolyte membrane is a proton exchange membrane.

5. The apparatus for producing an organic compound according to claim 1, wherein the reaction raw material of the cathode liquid is an oil-soluble organic compound.

6. The apparatus for producing an organic compound according to claim 5, wherein the oil-soluble organic compound is a reducible compound.

7. The organic compound production apparatus according to claim 6, wherein the reducible compound has an acetylene bond or an alkene bond.

8. The organic compound production apparatus according to claim 6, wherein the reducible compound has an aromatic ring.

9. The organic compound production apparatus according to claim 1, wherein the absolute value of the difference in specific gravity between the water derived from the anode solution and the reaction raw material of the cathode solution, and the absolute value of the difference in specific gravity between the water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

10. The organic compound production apparatus according to claim 2, wherein the reaction raw material of the anode solution is an oil-soluble organic compound.

11. The apparatus for producing an organic compound according to claim 10, wherein the oil-soluble organic compound is an oxidizable compound.

12. The apparatus for producing organic compounds according to claim 11, wherein the oxidizable compound is a compound having one or more functional groups selected from a hydroxyl group, an aldehyde group, a ketone group, an ether group, an amine group, a thiol group, and an unsaturated hydrocarbon group.

13. The organic compound production apparatus according to claim 2, wherein the absolute value of the difference in specific gravity between the water derived from the cathode solution and the reaction raw material of the anode solution and / or the organic compound produced on the anode side is 160 g / L or less.

14. An electrolytic cell having an anode portion, a cathode portion, and a solid polymer electrolyte membrane disposed between the anode portion and the cathode portion, an anode tank for supplying anode liquid to the anode portion, A cathode tank for supplying cathode liquid to the cathode section, An oil-water separator separates an oil-water mixture containing water derived from the anode solution that has been mixed into the cathode side through the solid polymer electrolyte membrane, the reaction raw materials of the cathode solution, and organic compounds produced on the cathode side into an oil layer and an oil layer. Equipped with, The oil-water separator is provided in an apparatus that (i) is placed between the supply of the cathode liquid from the cathode tank to the cathode section, or (ii) is placed between the return of the cathode liquid from the cathode section to the cathode tank. A method for producing organic compounds.

15. An electrolytic cell having an anode portion, a cathode portion, and a solid polymer electrolyte membrane disposed between the anode portion and the cathode portion, an anode tank for supplying anode liquid to the anode portion, A cathode tank for supplying cathode liquid to the cathode section, An oil-water separator separates an oil-water mixture containing water derived from the cathode solution mixed into the anode portion through the solid polymer electrolyte membrane, the reaction raw materials of the anode solution, and organic compounds produced on the anode portion into an oil layer and an oil layer. Equipped with, The oil-water separator is positioned (iii) between the supply of the anode liquid from the anode tank to the anode section, or (iv) between the return of the anode liquid from the anode section to the anode tank. A method for producing organic compounds.

16. The method for producing an organic compound according to claim 14 or 15, wherein the oil-water separator has a separation membrane that separates the oil-water mixture into an aqueous layer and an oil layer.

17. The method for producing an organic compound according to claim 14 or 15, wherein the solid polymer electrolyte membrane is a proton exchange membrane.

18. The method for producing an organic compound according to claim 14, wherein the reaction raw material of the cathode solution is an oil-soluble organic compound.

19. The method for producing an organic compound according to claim 18, wherein the oil-soluble organic compound is a reducible compound.

20. The method for producing an organic compound according to claim 19, wherein the reducible compound has an acetylene bond or an alkene bond.

21. The method for producing an organic compound according to claim 19, wherein the reducible compound has an aromatic ring.

22. The method for producing an organic compound according to claim 14, wherein the absolute value of the difference in specific gravity between the water derived from the anode solution and the reaction raw material of the cathode solution, and the absolute value of the difference in specific gravity between the water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

23. An electrolytic cell having an anode portion, a cathode portion, and a solid polymer electrolyte membrane disposed between the anode portion and the cathode portion, an anode tank for supplying anode liquid to the anode portion, A cathode tank for supplying cathode liquid to the cathode section, An oil-water separator separates an oil-water mixture containing water derived from the anode solution that has been mixed into the cathode side through the solid polymer electrolyte membrane, the reaction raw materials of the cathode solution, and organic compounds produced on the cathode side into an oil layer and an oil layer. Equipped with, A method for producing an organic compound, using an oil-water separator that is positioned (i) between supplying the cathode liquid from the cathode tank to the cathode section, or (ii) between returning the cathode liquid from the cathode section to the cathode tank, The oil-water separator has a separation membrane that separates the oil-water mixture into a water layer and an oil layer. The organic compound generated on the cathode side is a synthetic fragrance. A method for producing organic compounds.

24. The method for producing an organic compound according to claim 23, wherein the reaction raw material of the cathode solution is ethyl 2-phenylpropionate, and the organic compound produced on the cathode side is ethyl 2-cyclohexylpropionate.

25. The method for producing an organic compound according to claim 15, wherein the reaction raw material of the anode solution is an oil-soluble organic compound.

26. The method for producing an organic compound according to claim 25, wherein the oil-soluble organic compound is an oxidizable compound.

27. The method for producing an organic compound according to claim 26, wherein the oxidizable compound is a compound having one or more functional groups selected from a hydroxyl group, an aldehyde group, a ketone group, an ether group, an amine group, a thiol group, and an unsaturated hydrocarbon group.

28. The method for producing an organic compound according to claim 15, wherein the absolute value of the difference in specific gravity between the water derived from the cathode solution and the reaction raw material of the anode solution and / or the organic compound produced on the anode side is 160 g / L or less.

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