Organic compound production device and organic compound production method

Abstract

The present invention provides an organic compound production device which has a high effective current density and can more efficiently perform an electrochemical reaction. This organic compound production device comprises: an electrolysis tank having an anode part 4, a cathode part 5, and a solid polymer electrolyte membrane 3 positioned between the anode part 4 and the cathode part 5; an anode tank 6 for supplying an anolyte to the anode part 4; a cathode tank 7 for supplying a catholyte to the cathode part 5; and an oil-water separator 12 for separating an oil-water liquid mixture into a water layer and an oil layer, said oil-water liquid mixture containing anolyte-derived water which has contaminated the cathode part 5 side via the solid polymer electrolyte membrane 3, a catholyte reaction starting material, and an organic compound generated on the cathode part 5 side. The oil-water separator 12 is positioned (i) while the catholyte is being supplied from the cathode tank 7 to the cathode part 5, or (ii) while the catholyte is being returned from the cathode part 5 to the cathode tank 7.

Description

Apparatus for producing organic compounds and method for producing organic compounds

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

[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 hydride 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.

[0004] International Publication No. 2022 / 118932

[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 studies have been conducted 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.

[0007] The inventors have found that the above problems 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. That is, the present invention provides the following [1] to [5]. [1] An organic compound manufacturing apparatus comprising: 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, wherein the oil-water separator is disposed (i) between supplying the cathode solution from the cathode tank to the cathode section, or (ii) between returning the cathode solution from the cathode section to the cathode tank. [2] An organic compound manufacturing apparatus comprising: 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 an organic compound produced on the anode section side into an oil layer and an oil layer, wherein the oil-water separator is disposed (iii) between supplying the anode solution from the anode tank to the anode section, or (iv) between returning the anode solution from the anode section to the anode tank.[3] A method for producing an organic compound, comprising: 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 solution to the anode portion; a cathode tank for supplying cathode solution to the cathode portion; and an oil-water separator for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode portion side through the solid polymer electrolyte membrane, reaction raw materials for the cathode solution, and an organic compound produced on the cathode portion side into an oil layer and an oil layer, wherein the oil-water separator is disposed (i) between supplying the cathode solution from the cathode tank to the cathode portion, or (ii) between returning the cathode solution from the cathode portion to the cathode tank. [4] A method for producing an organic compound, comprising: 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 solution to the anode portion; a cathode tank for supplying cathode solution to the cathode portion; and an oil-water separator for separating an oil-water mixture containing water derived from the cathode solution mixed into the anode portion side through the solid polymer electrolyte membrane, reaction raw materials for the anode solution, and an organic compound produced on the anode portion side into an oil layer and an oil layer, wherein the oil-water separator is disposed (iii) between supplying the anode solution from the anode tank to the anode portion, or (iv) between returning the anode solution from the anode portion to the anode tank.[5] A method for producing an organic compound, comprising: 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 solution to the anode portion; a cathode tank for supplying cathode solution to the cathode portion; and an oil-water separator for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode portion side through the solid polymer electrolyte membrane, reaction raw materials for the cathode solution, and an organic compound produced on the cathode portion side into an aqueous layer and an oil layer, wherein the oil-water separator is placed (i) between supplying the cathode solution from the cathode tank to the cathode portion, or (ii) between returning the cathode solution from the cathode portion to the cathode tank, wherein the oil-water separator has a separation membrane for separating the oil-water mixture into an aqueous layer and an oil layer, and the organic compound produced on the cathode portion side is a synthetic fragrance.

[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.

[0009] 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 (i) the position when supplying cathode liquid from the cathode tank 7 to the cathode section 5. 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 (ii) the position when returning cathode liquid from the cathode section 5 to the cathode tank 7. This is a schematic diagram of an organic compound manufacturing apparatus according to the second embodiment of the present invention, in which the oil-water separator 12 is arranged in (iii) the position when supplying anode liquid from the anode tank 6 to the anode section 4. This is a schematic diagram of an organic compound manufacturing apparatus according to the second embodiment of the present invention, in which the oil-water separator 12 is arranged in (iv) the position when returning anode liquid from the anode section 4 to the anode tank 6. This is a schematic diagram of an organic compound manufacturing apparatus without an oil-water separator.

[0010] An organic compound manufacturing apparatus according to the first embodiment of the present invention comprises 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 an organic compound produced on the cathode section side into an oil layer and an oil layer, wherein the oil-water separator is disposed (i) between supplying cathode solution from the cathode tank to the cathode section, or (ii) between returning cathode solution from the cathode section to the cathode tank.

[0011] An organic compound production apparatus according to a second embodiment of the present invention comprises 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 an organic compound produced on the anode section side into an oil layer and an oil layer, wherein the oil-water separator is disposed (iii) between supplying anode solution from the anode tank to the anode section, or (iv) between returning anode solution from the anode section to the anode tank.

[0012] The organic compound manufacturing apparatus according to the first and second embodiments of the present invention has the effect of having a high effective current density and enabling more efficient electrochemical reactions. The reason for this is not entirely clear, but it is thought to be as follows. In the electrode reaction of the first embodiment shown in Figures 1 and 2, some of the water contained in the anode solution present on the anode 4 side moves to the cathode electrode side through the solid polymer electrolyte membrane 3, along with hydrogen ions generated on the anode 4 side, and mixes with the cathode 5 side. This water is referred to as "contaminated water". In the first embodiment shown in Figures 1 and 2, the contaminated water originating from the anode solution that has mixed into the cathode 5 side can be suitably removed by an oil-water separator 12 placed at a predetermined position. In this way, the amount of contaminated water present on the cathode 5 side can be reduced, which increases the frequency of contact between the reaction raw materials and catalyst in the cathode solution, increases the effective current density derived from the electrochemical reaction, and is thought to enable more efficient electrochemical reactions. Furthermore, in the electrode reaction of the second embodiment shown in Figures 3 and 4, some of the water contained in the cathode solution present on the cathode 5 side moves to the anode 4 side through the solid polymer electrolyte membrane 3, for example, due to osmosis, and mixes into the anode 4 side. This water is referred to as "contaminated water". In the second embodiment shown in Figures 3 and 4, the contaminated water originating from the cathode solution that has mixed into the anode 4 side can be suitably removed by an oil-water separator 12 placed at a predetermined position. In this way, the amount of contaminated water present on the anode 4 side can be reduced, which increases the frequency of contact between the reaction raw materials and catalyst in the anode solution, increases the effective current density derived from the electrochemical reaction, and is thought to enable the electrochemical reaction to be carried out more efficiently. The "contaminated water" referred to in the first and second embodiments described above may include water originating from the following sources. - Water that diffuses due to the water concentration gradient between the anode portion 4 and the cathode portion 5; water that moves by osmotic pressure due to the concentration gradient of the electrolyte; water that moves along with hydrogen ions when 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 Apparatus] 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 placement"). 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 return of cathode liquid from the cathode section 5 to the cathode tank 7 (also referred to as "post-stage placement"). Figure 3 is a schematic diagram showing an organic compound manufacturing apparatus according to the 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 placement"). Figure 4 is a schematic diagram showing an organic compound manufacturing apparatus according to the second embodiment of the present invention, in which the oil-water separator 12 is positioned (iv) between the return of anode liquid from the anode section 4 to the anode tank 6 (also referred to as "post-stage placement"). 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> H ２ O→2H ＋ +2e － +1 / 2O ２ <Cathode electrode> R + 2H ＋ +2e － →RH ２

[0016] In the electrolytic cell of the first embodiment, at 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, at the cathode electrode side of the cathode section 5, a reduction reaction occurs in which the reaction raw material in the cathode solution (for example, an unsaturated hydrocarbon compound (R)) accepts the hydrogen ions and electrons that have moved to the cathode electrode side, and a reduction reaction product (for example, a hydride (RH)) is produced. ２ The desired organic compound 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 is the formation of a desired organic compound, which is a reduction reaction product, on the cathode electrode side. However, some of the water contained in the anode solution present on the anode 4 side moves to the cathode electrode side through the solid polymer electrolyte membrane 3, along with hydrogen ions generated on the anode 4 side, and mixes into the cathode 5 side. Here, the water originating from the anode solution that mixes into the cathode 5 side is referred to as "mixed water" as described above. In the first embodiment of the present invention, mixed water causes a decrease in the effective current density derived from 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 mixed water that has mixed into the cathode 5 side, and an oil layer containing the reaction raw materials of the cathode solution and the reduction reaction product generated on the cathode 5 side, 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 supply of cathode liquid from the cathode tank 7 to the cathode section 5 (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 return of cathode liquid from the cathode section 5 to the cathode tank 7 (also referred to as "post-stage placement"). The oil-water separator 12 of the first embodiment shown in Figures 1 and 2 has the function of separating an oil-water mixture containing water derived from the anode liquid (contaminated water) mixed into the cathode section 5 side through the solid polymer electrolyte membrane 3, and reaction raw materials of the cathode liquid and organic compounds generated on the cathode section 5 side, into an aqueous layer and an oil layer. The aqueous 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 section 5, hydrogen gas is also produced as a by-reaction. Therefore, the oil-water mixture after the electrode reaction also contains the by-produced 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 this 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 immediately after the electrode reaction, so the concentration of hydrogen gas is considered to be relatively low as it is diluted by the cathode liquid. Therefore, in the arrangement of the oil-water separator 12 in the first embodiment, placing the oil-water separator 12 upstream is preferable to placing the oil-water separator 12 downstream because it separates the oil-water mixture with a lower hydrogen gas concentration.

[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 density difference between the water layer and the oil layer is relatively small, and also makes the organic compound manufacturing apparatus compact, thus making it suitable for the dispersed manufacturing of organic compounds. Examples of oil-water separators include the "SEP-10," "SEP-200-SS (Stainless Steel 316)," "SEP-200-HS (Hasterloy C276)," "SEP-200-FP (Perfluorinated Polymers)," "SEP-3000-SS (Stainless Steel 316)," and "SEP-3000-HS (Hasterloy C276)" from ZaiputFlow Technologies. Furthermore, as separation membranes, for example, are ZaiputFlowTechnologies' "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", and "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", "IL-2000-S3000", and so on.

[0020] [Electrolytic Cell] As shown in FIGS. 1 and 2, the electrolytic cell of the first embodiment includes an anode part 4, a cathode part 5, and a solid polymer electrolyte membrane 3. The anode part 4 has an anode electrode composed of an anode catalyst layer 1a and an anode-side diffusion layer 1b, and an anode chamber 1c. The cathode part 5 has 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 (positive electrode) is arranged so as to contact one main surface of the solid polymer electrolyte membrane 3. The anode electrode is composed 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 arranged so as to contact the solid polymer electrolyte membrane 3. The anode catalyst layer 1a is, for example, a layer containing a catalyst and a catalyst binder.

[0023] Examples of the catalyst of the anode catalyst layer 1a include known catalysts used in the anode catalyst layer. Specifically, metals such as iridium (Ir), ruthenium (Ru), platinum (Pt), palladium (Pd), gold (Au), etc., or alloys, composite metals containing these metals, or oxides containing these metals can be mentioned. The catalyst of the anode catalyst layer 1a may have a carrier, and examples of the carrier include titanium oxide (TiO ２ ), porous carbon, stainless steel, etc.

[0024] Examples of the catalyst binder of the anode catalyst layer 1a include known catalyst binders used in the anode catalyst layer, etc. Specifically, perfluorocarbon sulfonic acid-based polymers such as "Nafion"; fluorine resins such as polytetrafluoroethylene (PTFE), tetrafluoroethylene - hexafluoropropylene copolymer (FEP), and polyvinylidene fluoride (PVDF) can be mentioned.

[0025] The anode-side diffusion layer 1b is arranged so as to contact the surface of the anode catalyst layer 1a opposite to the surface in contact with the solid polymer electrolyte membrane 3. The anode-side diffusion layer 1b uniformly diffuses the anode liquid supplied from the anode chamber 6 to the anode catalyst layer 1a. As the anode-side diffusion layer 1b, known diffusion layers used for the anode catalyst layer can be mentioned, specifically, a sheet made of metallic titanium, carbon paper, carbon cloth, carbon felt, etc.

[0026] <Cathode Electrode> The cathode electrode (negative electrode) is arranged so as to contact one main surface of the solid polymer electrolyte membrane 3. The cathode electrode is composed of a cathode catalyst layer 2a and a cathode-side diffusion layer 2b, and is housed in the cathode chamber 2c.

[0027] The cathode catalyst layer 2a is arranged so as to contact the solid polymer electrolyte membrane 3. The cathode catalyst layer 2a is, for example, a layer containing a catalyst and a catalyst binder.

[0028] As the catalyst of the cathode catalyst layer 2a, known catalysts used for the cathode catalyst layer can be mentioned, specifically, metals such as platinum (Pt), ruthenium (Ru), palladium (Pd), etc., or alloys of these metals. The catalyst of the cathode catalyst layer 2a may have a carrier, and examples of the carrier include carbon such as carbon black powder, graphitized carbon, carbon fiber, carbon nanotube, etc.

[0029] As the catalyst binder of the cathode catalyst layer 2a, known catalyst binders used for the cathode catalyst layer can be mentioned, specifically, perfluorocarbon sulfonic acid-based 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 arranged so as to contact the surface of the solid polymer electrolyte membrane 3 of the cathode catalyst layer 2a on the side opposite to the surface in contact therewith. The cathode-side diffusion layer 2b uniformly diffuses the cathode liquid supplied from the cathode tank 7 to the cathode catalyst layer 2a. As the cathode-side diffusion layer 2b, known diffusion layers used for the cathode catalyst layer can be mentioned, and specifically, porous materials composed of carbon fibers such as carbon paper, carbon cloth, and carbon felt can be mentioned.

[0031] <Solid Polymer Electrolyte Membrane> The solid polymer electrolyte membrane 3 is arranged between the anode part 4 and the cathode part 5. The solid polymer electrolyte membrane is preferably a proton exchange membrane. A proton exchange membrane (Proton Exchange Membrane, PEM) is a polymer membrane having a function of selectively passing hydrogen ions (protons). Proton exchange membranes are used in fuel cells, electrolyzers, etc.

[0032] As the proton exchange membrane, for example, fluorine-based polymer electrolyte membranes made of perfluorocarbon sulfonic acid-based polymers such as "Nafion"; engineering plastic-based polymer electrolyte membranes such as sulfonated polyether sulfone and sulfonated polyether ketone; polymer electrolyte membranes made of polybenzimidazole impregnated with phosphoric acid or sulfuric acid; CSE (NEOSEPA, containing sulfonated styrene-based copolymer, manufactured by Asahi Kasei Corporation), CMB (NEOSEPA, containing sulfonated styrene / divinylbenzene-based copolymer, manufactured by Asahi Kasei Corporation), and CMVN (SELEMION TM , containing sulfonated divinylbenzene / styrene copolymer, manufactured by AGC Engineering Co., Ltd.) and other polymer electrolyte membranes made of sulfonated styrene-based polymers can be mentioned.

[0033] It is preferable to arrange separators having grooves serving as flow paths, a large number of holes, etc. on both surfaces of the solid polymer electrolyte membrane 3. As the separator, for example, separators made of various conductive materials such as metal separators, carbon separators, and separators made of a material obtained by mixing graphite and resin can be mentioned.

[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 when it moves 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. Also, 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 density 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 in a location that allows the cathode liquid to be supplied to the cathode section 5.

[0039] [Cathode Liquid 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. Also, 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 equipment and piping mentioned above. Note that the location where the pump 9 or heater 11 is located is not limited to the locations shown in Figures 1 and 2, and may be changed as necessary.

[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 (logarithm of the partition coefficient (P) between octanol and water of the compound), which is an indicator of hydrophobicity, greater than 0. As the oil-soluble organic compound, a reducible compound is preferred, and among these, a reducible compound having an acetylene bond or an alkene bond, or a reducible compound having an aromatic ring is preferred, and a reducible compound having an aromatic ring is 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, one or more selected from arylalkyl carboxylic acid esters, aromatic hydrocarbons, aryl-substituted alkanols, and arylalkyl carboxylic acids are preferred from the viewpoint of improving the recovery rate when separating oil and water and carrying out the electrochemical reaction more efficiently. 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 the reaction raw material for the cathode solution, raw materials of high value-added organic compounds are preferred from the viewpoint of achieving both high environmental value and high return on investment. Examples of raw materials of high value-added organic compounds include raw materials for synthetic fragrances, pharmaceutical raw materials, pharmaceutical intermediates, high boiling point industrial solvents, and raw materials for liquid organic hydrogen carriers. From the viewpoint of having a small density difference with water and being able to easily exert the effects of the present invention, one or more of the following are preferred as raw materials for synthetic fragrances: ethyl 2-phenylpropionate, 1-(2-tert-butylphenyloxy)-2-butanol, 2-methylene undecanal, 2-cyclohexyl acrylaldehyde, 3,6-dimethylhept-3-en-2-one, and 7-methylocta-4-en-3-one. Examples of raw materials for pharmaceutical raw materials, pharmaceutical intermediates, high-boiling point industrial solvents, and liquid organic hydrogen carriers include naphthalene, p-nitrophenol, pyridine, and aniline.

[0043] In the present invention, preferred oil-soluble organic compounds are those in which, when the compound is mixed and stirred with water in a mass ratio (oil:water) of 3:1 and left to stand under gravity for 30 seconds (or 2 hours) without applying any external force, at least one of the following is observed: (a) the oil phase and water phase do not separate into two distinct layers, (b) oil droplets remain in the water layer, (c) water droplets remain in the oil layer, or (d) turbidity remains in either the oil or water layer, and oil-water separation by gravity is not achieved.

[0044] Oil-soluble organic compounds that produce the aforementioned observation results under standard static conditions are difficult to separate by gravity from water mixed in by electrolysis. Therefore, when such oil-soluble organic compounds are applied to the organic compound production apparatus and method for producing organic compounds of the present invention, which are equipped with an oil-water separator, improvements in the recovery efficiency of the reaction solution and the effective current density are particularly likely to be demonstrated.

[0045] The ease with which the recovery efficiency and effective current density of the reaction solution described above are improved can be evaluated under conditions consistent with the examples in this specification (mixing ratio 3:1, standing under gravity for 30 seconds / 2 hours, visual observation). Furthermore, as already mentioned, compounds for which oil-water separation by gravity sedimentation is not achieved in this evaluation are preferably used as oil-soluble organic compounds. Specific examples of such oil-soluble organic compounds include raw materials used in the field of synthetic fragrances, namely ethyl 2-phenylpropionate, 1-(2-tert-butylphenyloxy)-2-butanol, 2-methylene undecanal, 3,6-dimethylhepto-3-en-2-one, and 7-methylocta-4-en-3-one.

[0046] In the first embodiment, the density 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.

[0047] In this specification, unless otherwise specified, numerical values ​​relating to density (g / L) and density difference shall be those measured at 30°C. The density of the reaction material in the cathode solution and the density difference between it and the reaction material in the anode solution (e.g., water) are set to a degree that simultaneously enhances the reactivity of the reaction material and improves the behavior of oil-water separation, in other words, promotes gravity sedimentation.

[0048] In the first embodiment, the absolute value of the density 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 density 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.

[0049] In the first embodiment, the temperature of the reaction raw materials in the anode solution and the reaction raw materials in the cathode solution are 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.

[0050] 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 density difference 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 density difference 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.

[0051] [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 when separating oil and water 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. Furthermore, alkylcyclohexane is preferred as alkylcycloalkane, and methylcyclohexane is preferred as alkylcyclohexane.

[0052] [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.

[0053] [Electrode Reaction] The electrode reaction carried out in the electrolytic cell of the second embodiment is preferably an oxidation reaction, and the reaction raw material of the anode solution is preferably an alcohol (R-CH ２ Let's take the case of -OH) as an example. <Anode electrode> R-CH ２ -OH→R-CHO+2H ＋ +2e － <Cathode electrode> 2H ＋ +2e － →H ２

[0054] In the electrolytic cell of the second embodiment, on the anode electrode side of the anode section 4, the reaction raw material of the anode solution (for example, alcohol (R-CH)) ２An oxidation reaction occurs in which -OH)) releases hydrogen ions and electrons, and a desired organic compound, which is an oxidation reaction product (e.g., aldehyde (R-CHO)), is produced. 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, 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.

[0055] Thus, in the electrode reaction of the second embodiment, the main reaction is the formation of a desired organic compound, which is an oxidation reaction product, on the anode electrode side. However, some of the water contained in the cathode solution present on the cathode 5 side moves to the anode electrode side through the solid polymer electrolyte membrane 3, for example, due to osmosis, and mixes into the anode 4 side. Here, the water originating from the cathode solution that has mixed into the anode 4 side is referred to as "contaminated water" as described above. In the second embodiment of the present invention, the contaminated water causes a decrease in the effective current density derived from 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 the contaminated water mixed into the anode 4 side and an oil layer containing the reaction raw materials of the anode solution and the oxidation reaction product generated on the anode 4 side, into an aqueous layer and an oil layer.

[0056] [Oil-Water Separator] The oil-water separator 12 of the second embodiment shown in Figure 3 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 placement"). The oil-water separator 12 of the second embodiment shown in Figure 4 is positioned (iv) between the return of anode liquid from the anode section 4 to the anode tank 6 (also referred to as "post-stage placement"). The oil-water separator 12 of the second embodiment shown in Figures 3 and 4 has the function of separating an oil-water mixture containing water derived from the cathode liquid (contaminated water) mixed into the anode section 4 side through the solid polymer electrolyte membrane 3, and reaction raw materials of the anode liquid and organic compounds generated on the anode section 4 side, into an aqueous layer and an oil layer. The aqueous 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 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. It is thought that the "oxygen gas" produced as a by-reaction originates from the oxygen generated by the electrolysis of the contaminated water mixed into the anode 4 side, as described below. ２ O→2H ＋ +2e － +1 / 2O ２ When the oil-water separator 12 is placed downstream, the oil-water separator separates the oil-water mixture immediately after the electrode reaction, and therefore the concentration of oxygen gas in this 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, and therefore 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 when it is placed upstream is preferable to the arrangement when it is placed downstream, because it separates the oil-water mixture with a lower oxygen gas concentration.

[0057] 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 density difference between the water layer and the oil layer in the oil-water mixture is relatively small, it is preferable that the oil-water separator 12 is equipped with a separation membrane, from the viewpoint of being able to separate the oil-water mixture into a water layer and an oil layer and making the organic compound manufacturing apparatus compact, which is suitable for the dispersion manufacturing of organic compounds.

[0058] [Electrolytic Cell] The electrolytic cell of the second embodiment, as shown in Figures 3 and 4, 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.

[0059] <Solid Polymer Electrolyte Membrane> The solid polymer electrolyte membrane 3 is positioned between the anode portion 4 and the cathode portion 5, similar to the first embodiment, and is preferably a proton exchange membrane, similar to the first embodiment.

[0060] [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.

[0061] [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 when it moves 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. Also, 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 equipment and piping mentioned above. Also, the location where the pump 8 or heater 10 is located is not limited to the locations shown in Figures 3 and 4, and may be changed as needed.

[0062] <Anode Solution> In the second embodiment, an oil-soluble organic compound is preferred as the reaction raw material for the anode solution. Among the oil-soluble organic compounds, an oxidizable compound is preferred. Among the oxidizable compounds, it is preferable that the compound has 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. Among these, from the viewpoint of improving the recovery rate when separating oil and water and carrying out the electrochemical reaction more efficiently, a compound having one or more groups selected from a hydroxyl group, an aldehyde group, and a ketone group is preferred, and a compound having one or more groups selected from a hydroxyl group and an aldehyde group is more preferred. Among the oxidizable compounds that serve 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. Examples of benzyl alcohol derivatives include 2-methylbenzyl alcohol, 4-methylbenzyl alcohol, 4-(dimethylamino)benzyl alcohol, and cinnamyl alcohol.

[0063] In the second embodiment, the density 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.

[0064] [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.

[0065] [Cathode Liquid 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. Also, 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.

[0066] <Cathode Liquid> In the second embodiment, the cathode liquid 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.

[0067] In the second embodiment, the density of the reaction raw materials of the cathode liquid 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.

[0068] In the second embodiment, the absolute difference between the density of the reaction raw materials in the cathode solution at 30°C and the density 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.

[0069] [Oxidation Reaction Products] Using the organic compound production apparatus according to the second embodiment, oil-soluble organic compounds, which are oxidation reaction products, 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 when separating oil and water 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 a reaction raw material for the anode solution is an alcohol, the resulting oxidation reaction product is an aldehyde. When the oxidizable compound is a primary alcohol, the resulting oxidation reaction product is hexanal, decanal, etc. When the oxidizable compound is benzyl alcohol or cinnamyl alcohol, the resulting oxidation reaction product is benzaldehyde or 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.

[0070] The organic compound production apparatus of the present invention can be further modified by adding various other forms 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 aqueous 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 aqueous 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 improve the flow rate as much as possible within the range in which oil-water separation is possible. These forms 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 water 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 fluid. 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 where oil-water separation is possible. These configurations can be arbitrarily selected.

[0071] With regard to the embodiments described above, the present invention further discloses the following organic compound manufacturing apparatus and organic compound manufacturing method.

[0072] <1> An organic compound manufacturing apparatus comprising: 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 side 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, wherein the oil-water separator is disposed (i) between supplying the cathode solution from the cathode tank to the cathode section, or (ii) between returning the cathode solution from the cathode section to the cathode tank.

[0073] <2> An organic compound manufacturing apparatus comprising: 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, wherein the oil-water separator is disposed (iii) between supplying the anode solution from the anode tank to the anode section, or (iv) between returning the anode solution from the anode section to the anode tank.

[0074] <3> The organic compound production apparatus according to <1> or <2>, wherein the oil-water separator has a separation membrane that separates the oil-water mixture into a water layer and an oil layer.

[0075] <4> The organic compound manufacturing apparatus according to <1> or <2>, wherein the solid polymer electrolyte membrane is a proton exchange membrane.

[0076] <5> The apparatus for producing organic compounds according to <1>, wherein the reaction raw material of the cathode solution is an oil-soluble organic compound.

[0077] <6> The apparatus for producing organic compounds according to <5>, wherein the oil-soluble organic compound is a reducible compound.

[0078] <7> The apparatus for producing organic compounds according to <6>, wherein the reducible compound has an acetylene bond or an alkene bond.

[0079] <8> The apparatus for producing organic compounds according to <6>, wherein the reducible compound has an aromatic ring.

[0080] <9> The organic compound manufacturing apparatus according to <1> or <3>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw material of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

[0081] <10> The organic compound production apparatus according to <2>, wherein the reaction raw material of the anode solution is an oil-soluble organic compound.

[0082] <11> The apparatus for producing organic compounds according to <10>, wherein the oil-soluble organic compound is an oxidizable compound.

[0083] <12> The apparatus for producing organic compounds according to <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.

[0084] <13> The organic compound production apparatus according to <2>, wherein the absolute value of the density difference between the water derived from the cathode solution and the reaction raw materials of the anode solution and / or the organic compound produced on the anode side is 160 g / L or less.

[0085] <14> A method for producing an organic compound, comprising: 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 solution to the anode portion; a cathode tank for supplying cathode solution to the cathode portion; and an oil-water separator for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode portion side through the solid polymer electrolyte membrane, reaction raw materials for the cathode solution, and an organic compound produced on the cathode portion side into an oil layer and an oil layer, wherein the oil-water separator is disposed (i) between supplying the cathode solution from the cathode tank to the cathode portion, or (ii) between returning the cathode solution from the cathode portion to the cathode tank.

[0086] <15> A method for producing an organic compound, comprising: 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 solution to the anode portion; a cathode tank for supplying cathode solution to the cathode portion; and an oil-water separator for separating an oil-water mixture containing water derived from the cathode solution mixed into the anode portion side through the solid polymer electrolyte membrane, the reaction raw materials of the anode solution, and an organic compound produced on the anode portion side into an oil layer and an oil layer, wherein the oil-water separator is disposed (iii) between supplying the anode solution from the anode tank to the anode portion, or (iv) between returning the anode solution from the anode portion to the anode tank.

[0087] <16> The method for producing an organic compound according to <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.

[0088] <17> The method for producing an organic compound according to <14> or <15>, wherein the solid polymer electrolyte membrane is a proton exchange membrane.

[0089] <18> The method for producing an organic compound according to <14>, wherein the reaction raw material of the cathode solution is an oil-soluble organic compound.

[0090] <19> The method for producing an organic compound according to <18>, wherein the oil-soluble organic compound is a reducible compound.

[0091] <20> A method for producing an organic compound according to <19>, wherein the reducible compound has an acetylene bond or an alkene bond.

[0092] <21> A method for producing the organic compound according to <19>, wherein the reducible compound has an aromatic ring.

[0093] <22> The method for producing an organic compound according to <14> or <16>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw material of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

[0094] <23> A method for producing an organic compound, comprising: 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 solution to the anode portion; a cathode tank for supplying cathode solution to the cathode portion; and an oil-water separator for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode portion side through the solid polymer electrolyte membrane, reaction raw materials for the cathode solution, and an organic compound produced on the cathode portion side into an aqueous layer and an oil layer, wherein the oil-water separator is disposed (i) between supplying the cathode solution from the cathode tank to the cathode portion, or (ii) between returning the cathode solution from the cathode portion to the cathode tank, wherein the oil-water separator has a separation membrane for separating the oil-water mixture into an aqueous layer and an oil layer, and the organic compound produced on the cathode portion side is a synthetic fragrance.

[0095] <24> The method for producing an organic compound according to <23>, wherein the reaction raw material of the cathode solution is ethyl 2-phenylpropionate and the resulting organic compound is ethyl 2-cyclohexylpropionate.

[0096] <25> The method for producing an organic compound according to <15>, wherein the reaction raw material of the anode solution is an oil-soluble organic compound.

[0097] <26> The method for producing an organic compound according to <25>, wherein the oil-soluble organic compound is an oxidizable compound.

[0098] <27> The method for producing an organic compound according to <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.

[0099] <28> The method for producing an organic compound according to <15>, wherein the absolute value of the density difference between the water derived from the cathode solution and the organic compound produced on the anode side of the reaction raw material of the anode solution is 160 g / L or less.

[0100] <29> The organic compound production apparatus according to <1>, wherein the oil-water separator has a separation membrane that separates the oil-water mixture into a water layer and an oil layer, and the reaction raw material of the cathode liquid is an oil-soluble organic compound.

[0101] <30> The apparatus for producing organic compounds according to <29>, wherein the oil-soluble organic compound is a reducible compound.

[0102] <31> The apparatus for producing organic compounds according to <30>, wherein the reducible compound has an acetylene bond or an alkene bond, or the reducible compound has an aromatic ring.

[0103] <32> An organic compound manufacturing apparatus according to any one of <29> to <31>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

[0104] <33> The oil-soluble organic compound is an oil-soluble organic compound in which, after mixing and stirring the oil-soluble organic compound with water in a mass ratio (oil:water) = 3:1 and then letting it stand for 30 seconds under gravity without applying any external force, at least one of the following results is observed by visual inspection, and oil-water separation by gravity is not achieved: [a] the oil phase and the water phase do not separate into two distinct layers, [b] oil droplets remain in the water layer, [c] water droplets remain in the oil layer, [d] turbidity remains in the oil layer or the water layer, as described in any one of <29> to <32>, an organic compound manufacturing apparatus.

[0105] <34> The oil-soluble organic compound is an oil-soluble organic compound in which, after mixing and stirring the oil-soluble organic compound with water in a mass ratio (oil:water) = 3:1 and then letting it stand for 2 hours under gravity without applying any external force, at least one of the following results can be observed visually, and oil-water separation by gravity is not achieved: [a] the oil phase and the water phase do not separate into two distinct layers, [b] oil droplets remain in the water layer, [c] water droplets remain in the oil layer, [d] turbidity remains in the oil layer or the water layer, as described in any one of <29> to <32>, an organic compound manufacturing apparatus.

[0106] <35> The method for producing an organic compound according to <14>, 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 reaction raw material of the cathode liquid is an oil-soluble organic compound.

[0107] <36> The method for producing an organic compound according to <35>, wherein the oil-soluble organic compound is a reducible compound.

[0108] <37> The method for producing an organic compound according to <36>, wherein the reducible compound has an acetylene bond or an alkene bond, or the reducible compound has an aromatic ring.

[0109] <38> A method for producing an organic compound according to any one of <35> to <37>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

[0110] <39> The oil-soluble organic compound is an oil-soluble organic compound in which, after mixing and stirring the oil-soluble organic compound with water in a mass ratio (oil:water) = 3:1 and then allowing it to stand for 30 seconds under gravity without applying any external force, at least one of the following results is observed by visual inspection, and oil-water separation by gravity is not achieved: [a] the oil phase and the water phase do not separate into two distinct layers, [b] oil droplets remain in the water layer, [c] water droplets remain in the oil layer, [d] turbidity remains in the oil layer or the water layer. A method for producing an organic compound according to any one of <35> to <38>.

[0111] <40> The oil-soluble organic compound is an oil-soluble organic compound in which, after mixing and stirring the oil-soluble organic compound and water in a mass ratio (oil:water) = 3:1 and then allowing it to stand for 2 hours under gravity without applying any external force, at least one of the following results is observed by visual inspection, and oil-water separation by gravity is not achieved: [a] the oil phase and the water phase do not separate into two distinct layers, [b] oil droplets remain in the water layer, [c] water droplets remain in the oil layer, [d] turbidity remains in the oil layer or the water layer. A method for producing an organic compound according to any one of <35> to <38>.

[0112] <41> The method for producing an organic compound according to <23>, wherein the reaction raw material of the cathode solution is an oil-soluble organic compound.

[0113] <42> The method for producing an organic compound according to <41>, wherein the oil-soluble organic compound is a reducible compound.

[0114] <43> The method for producing an organic compound according to <42>, wherein the reducible compound is a reducible compound having an acetylene bond, an alkene bond, or an aromatic ring.

[0115] <44> The method for producing an organic compound according to any one of <41> to <43>, wherein the reducible compound comprises one or more selected from ethyl 2-phenylpropionate, 1-(2-tert-butylphenyloxy)-2-butanol, 2-methylene undecanal, 2-cyclohexyl acrylaldehyde, 3,6-dimethylhept-3-en-2-one, and 7-methylocta-4-en-3-one.

[0116] A method for producing an organic compound according to any one of items <40> to <43>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

[0117] <46> An organic compound manufacturing apparatus according to any one of <1> or <29> to <34>, comprising an anode pump (8) in the anode liquid supply channel (14a) and a cathode pump (9) in the cathode liquid supply channel (15a).

[0118] <47> The organic compound manufacturing apparatus according to <46>, further comprising a heater (10) in the anode liquid supply channel (14a) and a heater (11) in the cathode liquid supply channel (15a).

[0119] <48> The organic compound production apparatus according to <46> or <47>, wherein the oil-water separator (12) is located between the cathode tank (7) and the cathode liquid to the cathode section (5), and is located downstream of at least one of the cathode pump (9) or the cathode heater (11).

[0120] <49> The organic compound manufacturing apparatus according to <46> or <48>, comprising an anode liquid return channel (14b) and a cathode liquid return channel (15b).

[0121] <50> The organic compound production apparatus according to <49>, further comprising a return pipe that returns at least a portion of the aqueous layer separated by the oil-water separator (12) to the anode tank (6).

[0122] <51> The organic compound production apparatus according to <49>, further comprising a structure that allows at least a portion of the water layer separated by the oil-water separator (12) to be discharged to the outside.

[0123] <52> The organic compound manufacturing apparatus according to <50> or <51>, further comprising a back pressure adjustment member (back pressure valve) downstream of the outlet side of the oil-water separator (12).

[0124] <53> An organic compound manufacturing apparatus according to any one of <49> to <52>, wherein the density of the reaction raw material of the cathode liquid at the reaction temperature is 800 g / L or more and 1200 g / L or less.

[0125] <54> An organic compound manufacturing apparatus according to any one of <49> to <52>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

[0126] <55> An organic compound manufacturing apparatus according to any one of <49> to <52>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 180 g / L or less.

[0127] <56> An organic compound manufacturing apparatus according to any one of <49> to <52>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 160 g / L or less.

[0128] <57> An organic compound manufacturing apparatus according to any one of <49> to <52>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 150 g / L or less.

[0129] <58> An organic compound manufacturing apparatus according to any one of <49> to <52>, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between the water derived from the anode solution and the organic compound produced on the cathode side, are each 140 g / L or less.

[0130] <59> An organic compound production apparatus according to any one of <49> to <58>, wherein the reaction raw material of the cathode solution contains one or more selected from ethyl 2-phenylpropionate, 1-(2-tert-butylphenyloxy)-2-butanol, 2-methylene undecanal, 2-cyclohexyl acrylaldehyde, 3,6-dimethylhept-3-en-2-one, and 7-methylocta-4-en-3-one, and toluene.

[0131] <60> A method for producing an organic compound according to any one of <14> or <35> to <40>, wherein the anode solution is circulated and supplied by the anode pump (8), and the cathode solution is circulated and supplied by the cathode pump (9) to perform electrolysis.

[0132] <61> A method for producing an organic compound according to <60>, wherein the anode solution is heated in a heater (10) and the cathode solution is heated in a heater (11) to perform electrolysis.

[0133] <62> The method for producing an organic compound according to <60> or <61>, wherein the oil-water separator (12) is positioned between the cathode tank (7) and the cathode section (5) and is positioned downstream of at least one of the cathode pump (9) or the cathode heater (11) to supply to the cathode section.

[0134] <63> A method for producing an organic compound according to any one of <60> to <62>, wherein each liquid is circulated to each tank via the anode liquid return channel (14b) and the cathode liquid return channel (15b).

[0135] <64> A method for producing an organic compound according to any one of <60> to <63>, wherein at least a portion of the aqueous layer separated by the oil-water separator (12) is returned to the anode tank (6).

[0136] <65> A method for producing an organic compound according to any one of <60> to <63>, wherein at least a portion of the aqueous layer separated by the oil-water separator (12) is discharged to the outside.

[0137] <66> A method for producing an organic compound according to any one of <60> to <63>, wherein a back pressure valve is provided downstream of the outlet side of the oil-water separator (12) to improve the flow rate within a range in which oil-water separation is possible.

[0138] <67> A method for producing an organic compound according to any one of <63> to <66>, wherein electrolysis is performed while preferably maintaining the temperature of the reaction raw materials in the anode solution and the reaction raw materials in the cathode solution at 20°C or higher and 80°C or lower, more preferably at 25°C or higher and 70°C or lower.

[0139] <68> A method for producing an organic compound according to any one of <63> to <67>, wherein the density of the reaction raw materials of the cathode solution at any temperature is 800 g / L or more and 1200 g / L or less.

[0140] <69> A method for producing an organic compound according to any one of <63> to <68>, wherein the absolute value of the density difference between water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between water derived from the anode solution and the organic compound produced on the cathode side, are each 200 g / L or less.

[0141] <70> A method for producing an organic compound according to any one of <63> to <68>, wherein the absolute value of the density difference between water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between water derived from the anode solution and the organic compound produced on the cathode side, are each 180 g / L or less.

[0142] <71> A method for producing an organic compound according to any one of <63> to <68>, wherein the absolute value of the density difference between water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between water derived from the anode solution and the organic compound produced on the cathode side, are each 160 g / L or less.

[0143] <72> A method for producing an organic compound according to any one of <63> to <68>, wherein the absolute value of the density difference between water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between water derived from the anode solution and the organic compound produced on the cathode side, are each 150 g / L or less.

[0144] <73> A method for producing an organic compound according to any one of <63> to <68>, wherein the absolute value of the density difference between water derived from the anode solution and the reaction raw materials of the cathode solution, and the absolute value of the density difference between water derived from the anode solution and the organic compound produced on the cathode side, are each 140 g / L or less.

[0145] <74> A method for producing an organic compound according to any one of <63> to <73>, wherein the reaction raw material of the cathode solution contains one or more selected from ethyl 2-phenylpropionate, 1-(2-tert-butylphenyloxy)-2-butanol, 2-methylene undecanal, 2-cyclohexyl acrylaldehyde, 3,6-dimethylhept-3-en-2-one, and 7-methylocta-4-en-3-one, and toluene.

[0146] <75> The value obtained by dividing the cathode fluid flow rate by the effective electrode area, cathode fluid effective electrode area 1 cm² ２ The flow rate per unit is 0.2 mL / min / cm². ２ A method for producing an organic compound according to any one of claims <63> to <74>, wherein the reduction reaction is carried out while passing the mixture through the oil-water separator (12).

[0147] <76> A method for producing an organic compound according to any one of the claims <63> to <75>, wherein ethyl 2-phenylpropionate or toluene is used as a reaction raw material for the cathode solution, and electrolysis is performed at a potential difference of 1.8 V to obtain ethyl 2-cyclohexylpropionate or methylcyclohexane, respectively.

[0148] 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.

[0149] Example 1 (1) Electrolytic Cell A water electrolysis cell (manufactured by Eiwa Co., Ltd.) was used as the electrolytic cell. The main specifications of the electrolytic cell are as follows: 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 cm² ２ The electrodes used were CCMs (Catalist Coated Membranes) as shown below, and the CCMs and diffusion layers were mounted in a water electrolysis cell. <CCM (manufactured by Eiwa Co., Ltd.)> Solid polymer electrolyte membrane: Nafion N-117 Anode catalyst: IrO ２ / TiO ２ Catalyst (IrO ２ Loading amount: 1.0 mg / cm³ ２ ) Cathode catalyst: Pt / C catalyst (Pt loading amount 1.0 mg / cm²) 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 Co., Ltd.)

[0150] (2) Experimental apparatus The apparatus shown in Figure 1 was used as the experimental apparatus. An anode pump 8 (Q-100-TT-P-S, manufactured by Takumina Co., Ltd.) was used for the circulation and supply of the anode solution. A cathode pump 9 (Q-100-TT-P-S, manufactured by Takumina Co., Ltd.) was used for the circulation and supply of the cathode solution. Rubber heaters attached to both sides of the cell were used to heat the water electrolysis cell. An electrochemical measuring device 13 (Hz-Pro, manufactured by Meiden Hokuto Co., Ltd.) was used for voltage application and current measurement. The electrochemical measuring device 13 was connected to the anode electrode and cathode electrode of the electrolytic cell and measurements were performed. 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. 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 ZaiputFlow Technologies) with a separation membrane (OB-900-S10, manufactured by ZaiputFlow Technologies). In the apparatus shown in Figure 1, the oil-water separator 12 was positioned between the cathode tank 7 and the cathode liquid supply to the cathode section 5 (also referred to as "pre-stage placement").

[0151] (3) Experimental Procedure 50 g of ultrapure water (density at 30°C: 995.65 g / L), which is the anode solution, was placed in a 100 mL glass container, which is the anode tank 6. 70 g of ethyl 2-phenylpropionate (density at 30°C: 1000.7 g / L), which is the reaction raw material for the cathode solution, was placed in a 100 mL glass container, which is the cathode solution tank 7. The anode solution in anode tank 6 was stirred with a magnetic stirrer, and the anode solution flow rate was set to 5 mL / min using the anode pump 8. The anode solution was passed through the anode heater 10, the temperature was controlled to 60°C, and the solution was circulated and supplied 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, temperature controlled 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 this, the cathode liquid containing the contaminated water was returned to the cathode tank 7, passed through the cathode heater 11, temperature controlled 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 an electrochemical measuring device 13, the potential difference between the cathode potential and the anode potential was controlled to 1.8 V, and the hydrogenation reaction of ethyl 2-phenylpropionate was carried out for 5 hours to obtain ethyl 2-cyclohexylpropionate. Even after mixing the reaction raw material, ethyl 2-phenylpropionate, 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 was impossible. Similarly, after mixing the reaction raw material, 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 present in the water layer, confirming insufficient layer separation and that oil-water separation by gravity was impossible.

[0152] (4) Analysis At each of the hydrogenation reaction times of the cathode solution, 0 hours, 1 hour, and 5 hours, the cathode solution returning to the cathode tank 7 is collected and its composition is analyzed using gas chromatography (GC). The effective current density i, which is the current density derived from the hydrogenation reaction of the cathode solution, is calculated using the following formula. ｍ The results for Example 1 are shown in Tables 1 and 2.

[0153]

[0154] i ｍ Effective current density [mA / cm²] ２ ] y: Amount of hydride produced [mol] n: Number of reaction electrons [mol-e / mol] (In this embodiment, the number of reaction electrons = 6 mol-e / mol) 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 )

[0155] Example 2 Using the apparatus shown in Figure 2, the hydrogenation reaction of ethyl 2-phenylpropionate was carried out in the same procedure as in Example 1, except that 160 g of ultrapure water (density at 30°C: 995.65 g / L), which is the anode solution, was charged into a 500 mL glass container as the anode tank 6, and 50 g of ethyl 2-phenylpropionate (density at 30°C: 1000.7 g / L), which is the reaction raw material for the cathode solution, was charged into a 250 mL glass container as the cathode tank 7, to obtain ethyl 2-cyclohexylpropionate. In the apparatus shown in Figure 2, the oil-water separator 12 was placed between the cathode section 5 and the cathode solution returning to the cathode tank 7 (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, is carried out, 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.

[0156] 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 the ethyl 2-phenylpropionate, the reaction raw material for the cathode solution, was replaced with toluene (density at 30°C: 857.5 g / L), and 47 g of ultrapure water, the anode solution, and 45 g of toluene, the reaction raw material for the cathode solution, were charged. Methylcyclohexane was obtained. After mixing toluene and water in a 3:1 ratio and letting it stand for 30 seconds, both the oil layer and the water layer were clear, confirming that oil-water separation by gravity sedimentation was possible. The results of Example 3 are shown in Tables 1 and 2.

[0157] 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, which is the reaction raw material for the anode solution, and 47 g of toluene, which is the reaction raw material for the cathode solution, were charged. Methylcyclohexane was obtained. The results of Example 4 are shown in Table 2.

[0158] Comparative Example 1 The apparatus shown in Figure 5 was used as the experimental apparatus. The hydrogenation reaction of ethyl 2-phenylpropionate was carried out in the same procedure as in Example 1, except that 49 g of ultrapure water, which is the reaction raw material for the anode solution, and 48 g of ethyl 2-phenylpropionate, which is the reaction raw material for the cathode solution, were charged. Ethyl 2-cyclohexylpropionate was obtained. The apparatus shown in Figure 5 was not equipped with an oil-water separator 12. After the hydrogenation reaction of ethyl 2-phenylpropionate, which is the reaction raw material for the cathode solution supplied from the cathode tank 7 to the cathode section 5, was carried out, 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.

[0159] Comparative Example 2 The hydrogenation reaction of toluene was carried out in the same manner as in Example 3, using the apparatus shown in Figure 5, except that 48 g of ultrapure water was used as the anode solution and 48 g of toluene was used as the reaction raw material for the cathode solution, to obtain methylcyclohexane. The results of Comparative Example 2 are shown in Table 1.

[0160]

[0161] 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, equipped with the 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 was not equipped with the oil-water separator 12. On the other hand, Examples 3 and Comparative Example 2 are examples in which toluene was used as the reaction raw material for the cathode solution. Example 3, equipped with the oil-water separator 12 in a predetermined position, was found to have a higher effective current density and be capable of efficiently carrying out the hydrogenation reaction compared to Comparative Example 2, which was not equipped with the oil-water separator 12.

[0162]

[0163] 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. Example 1, in which the oil-water separator 12 was placed in the preceding stage, was found to have a higher effective current density and to be a device that can carry out the hydrogenation reaction more efficiently compared to Example 2, in which the oil-water separator 12 was 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. Example 3, in which the oil-water separator 12 was placed in the preceding stage, was found to have a higher effective current density and to be a device that can carry out the hydrogenation reaction more efficiently compared to Example 4, in which the oil-water separator 12 was placed in the subsequent stage.

[0164] 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 pump 9 Cathode pump 10 Anode heater 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 liquid circulation channel 15a Cathode liquid supply channel 15b Cathode liquid return channel

[0165] 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 organic compound manufacturing apparatus comprising: 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 side 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, wherein the oil-water separator is disposed (i) between supplying the cathode solution from the cathode tank to the cathode section, or (ii) between returning the cathode solution from the cathode section to the cathode tank.

2. An organic compound manufacturing apparatus comprising: 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, wherein the oil-water separator is disposed (iii) between supplying the anode solution from the anode tank to the anode section, or (iv) between returning the anode solution from the anode section to the anode tank.

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 a water 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 apparatus for producing an organic compound according to claim 6, wherein the reducible compound has an acetylene bond or an alkene bond.

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

9. The organic compound production apparatus according to claim 1 or 3, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw material of the cathode solution, and the absolute value of the density difference 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 apparatus for producing an organic compound 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 density difference between the water derived from the cathode solution and the reaction raw materials of the anode solution and / or the organic compound produced on the anode side is 160 g / L or less.

14. A method for producing an organic compound, comprising: 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 an organic compound produced on the cathode section side into an oil layer and an oil layer, wherein the oil-water separator is disposed (i) between supplying the cathode solution from the cathode tank to the cathode section, or (ii) between returning the cathode solution from the cathode section to the cathode tank.

15. A method for producing an organic compound, comprising: 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 an organic compound produced on the anode section side into an oil layer and an oil layer, wherein the oil-water separator is disposed (iii) between supplying the anode solution from the anode tank to the anode section, or (iv) between returning the anode solution from the anode section to the anode tank.

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 or 16, wherein the absolute value of the density difference between the water derived from the anode solution and the reaction raw material of the cathode solution, and the absolute value of the density difference 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. A method for producing an organic compound, comprising: 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 solution to the anode portion; a cathode tank for supplying cathode solution to the cathode portion; and an oil-water separator for separating an oil-water mixture containing water derived from the anode solution mixed into the cathode portion side through the solid polymer electrolyte membrane, reaction raw materials for the cathode solution, and an organic compound produced on the cathode portion side into an aqueous layer and an oil layer, wherein the oil-water separator is disposed (i) between supplying the cathode solution from the cathode tank to the cathode portion, or (ii) between returning the cathode solution from the cathode portion to the cathode tank, wherein the oil-water separator has a separation membrane for separating the oil-water mixture into an aqueous layer and an oil layer, and the organic compound produced on the cathode portion side is a synthetic fragrance.

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 density difference between the water derived from the cathode solution and the organic compound produced on the anode side of the reaction raw material of the anode solution is 160 g / L or less.

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