WO2020017246A1 - Appareil et procédé de photoréaction - Google Patents

Appareil et procédé de photoréaction Download PDF

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Publication number
WO2020017246A1
WO2020017246A1 PCT/JP2019/024967 JP2019024967W WO2020017246A1 WO 2020017246 A1 WO2020017246 A1 WO 2020017246A1 JP 2019024967 W JP2019024967 W JP 2019024967W WO 2020017246 A1 WO2020017246 A1 WO 2020017246A1
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WIPO (PCT)
Prior art keywords
plate
shaped member
light
light source
flow path
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PCT/JP2019/024967
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English (en)
Japanese (ja)
Inventor
強 荒井
雅彦 則常
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富士フイルム株式会社
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Priority to JP2020531198A priority Critical patent/JP7075490B2/ja
Publication of WO2020017246A1 publication Critical patent/WO2020017246A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B81—MICROSTRUCTURAL TECHNOLOGY
    • B81B—MICROSTRUCTURAL DEVICES OR SYSTEMS, e.g. MICROMECHANICAL DEVICES
    • B81B7/00—Microstructural systems; Auxiliary parts of microstructural devices or systems
    • B81B7/02—Microstructural systems; Auxiliary parts of microstructural devices or systems containing distinct electrical or optical devices of particular relevance for their function, e.g. microelectro-mechanical systems [MEMS]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings

Definitions

  • the present invention relates to a photoreaction device and a method.
  • a photoreaction device for performing a photoreaction by irradiation of light a device for continuously performing a photoreaction is known. This apparatus performs a photoreaction by irradiating the flowing reaction target liquid with light while flowing the reaction target liquid containing the photoreactive compound.
  • Patent Literature 1 describes an apparatus that includes a microreactor, a gas supply unit that supplies a non-source gas, and a liquid source supply unit that supplies a liquid source, and performs a photolysis reaction.
  • the microreactor is provided with a photocatalyst layer on the inner surface and includes a microchannel through which a liquid raw material flows.
  • the microchannel is made of a light-transmitting material and has a rectangular, circular, elliptical, or polygonal cross section.
  • the micro flow path has a flow path diameter of 10 to 2000 ⁇ m, and the length of the long side / short side when the cross section is rectangular, and the long diameter / short diameter when the cross section is circular is about 1 to 20. It has been.
  • the photoreactor of Patent Document 2 comprises a reaction section in which a layer of porous silicon is provided on the inner surface of a microchannel, a feeding unit for feeding a raw material liquid to the microchannel, and a light irradiating unit for irradiating light to the porous silicon layer.
  • the microchannel is a channel having a fine diameter of about several tens to several thousand ⁇ m, and is described as preferably having a width of 50 ⁇ m to 1000 ⁇ m and a depth of 10 ⁇ m to 1000 ⁇ m.
  • Patent Document 3 a transparent cylindrical inner container in which a tube is spirally wound, a light source arranged so as not to contact the cylindrical container, and a light source arranged between the inner container and the light source A photoreactor comprising a cooling tube is described.
  • an object of the present invention is to provide a photoreactor and a method which can increase the throughput while suppressing the size of the apparatus.
  • the present invention includes a reaction unit, a light source unit, and a light source side temperature control mechanism, and irradiates the reaction target liquid with light while flowing the reaction target liquid containing the photoreactive compound. This causes a photoreaction.
  • the reaction section has a first plate-shaped member that transmits light, and a second plate-shaped member facing the first plate-shaped member with a gap.
  • the reaction section has a flat flow path in which a set of opposed surfaces is defined by a first plate-shaped member and a second plate-shaped member.
  • the light source unit is arranged on the opposite side of the first plate member from the second plate member side, and a plurality of light sources that emit light are arranged in a plane.
  • the light source side temperature control mechanism adjusts the temperature of the reaction section from the light source unit side.
  • the light source side temperature control mechanism preferably includes a third plate-shaped member and a light source side supply unit.
  • the third plate-shaped member is disposed on the light source unit side of the first plate-shaped member so as to face the first plate-shaped member with a gap, and transmits light.
  • the light source side supply unit supplies a heat transfer medium between the third plate-shaped member and the first plate-shaped member.
  • the second plate-like member reflects light.
  • first plate-shaped member and the second plate-shaped member are arranged in an upright posture.
  • the flat flow path is opened as a supply port of the liquid to be reacted at a lower part of the reaction part, and is opened as a discharge port at an upper part of the reaction part.
  • the ratio obtained by WP / TP is at least 3 in a cross section of the flat flow path orthogonal to the flow direction of the reaction target liquid. Is preferred.
  • the back side temperature control mechanism has a fourth plate-shaped member and a back side supply unit.
  • the fourth plate-shaped member is disposed on the opposite side of the second plate-shaped member from the first plate-shaped member, facing the second plate-shaped member with a gap.
  • the back side supply unit supplies the heat transfer medium between the second plate member and the fourth plate member.
  • a photoreaction is performed by irradiating the reaction target liquid with light while flowing the reaction target liquid containing the photoreactive compound.
  • a reaction target liquid is supplied to a flat flow path provided inside the reaction section, and the reaction target liquid flowing in the flat flow path is irradiated with light, and the temperature of the light source unit or the reaction section is reduced. Adjust.
  • the flat flow path has a set of opposing surfaces defined by a first plate-shaped member that transmits light and a second plate-shaped member facing the first plate-shaped member with a gap.
  • the light is radiated to the reaction target liquid by a light source unit in which a plurality of light sources for emitting light are arranged in a plane, the light being arranged on a side of the first plate member opposite to the second plate member side.
  • the processing amount is improved while suppressing an increase in the size of the apparatus.
  • a photoreaction device 10 irradiates a reaction target solution 11 with light while flowing a reaction target solution 11 containing a photoreactive compound (see FIG. 3). The photoreaction is performed continuously.
  • the light reaction device 10 includes a light source unit 13 and a reaction unit 14.
  • the light source unit 13 is for irradiating the reaction target liquid 11 with light.
  • the light source unit 13 is formed in a plate shape, and one surface 13a is an emission surface from which light is emitted.
  • reference numeral 13a is given to the emission surface.
  • the light source unit 13 is arranged such that the emission surface 13a is parallel to a direction X in which the reaction target liquid 11 flows (hereinafter, referred to as a flow direction).
  • a flow direction in which the reaction target liquid 11 flows
  • the light source unit 13 is provided in a vertically upright posture (vertical posture) with the emission surface 13a in the vertical direction. Details of the light source unit 13 will be described later with reference to another drawing.
  • the direction orthogonal to the flow direction X is defined as the width direction Y
  • the direction orthogonal to both the flow direction X and the width direction Y is defined as the thickness direction Z.
  • the reaction unit 14 includes a unit main body 21, a liquid sending section 22, a recovery section 23, and a cooler 24.
  • the unit body 21 is formed in a substantially rectangular parallelepiped shape, but the shape is not limited to this example.
  • An opening 27 a for guiding light from the light source unit 13 to the inside is formed in the housing 27 of the unit main body 21.
  • the unit main body 21 is arranged so that the opening 27a faces the light source unit 13.
  • the opening 27a is rectangular, but the shape of the opening is not limited to this example.
  • the liquid sending section 22 and the collecting section 23 are connected to the unit main body 21, and the liquid sending section 22 supplies the reaction target liquid 11 to the unit main body 21, and the collecting section 23 converts the reaction target liquid 11 having undergone the photoreaction into a unit. Collected from the main body 21.
  • the liquid sending section 22 is provided at the lower part of the unit main body 21, specifically, at the supply port S 1 formed at the bottom surface of the housing 27.
  • the collection unit 23 is connected to an upper portion of the unit main body 21, specifically, to a discharge port D ⁇ b> 1 (see FIG. 3B) formed on the top surface of the housing 27.
  • the cooler 24 is connected to the unit main body 21 through pipes L1 to L6.
  • the cooler 24 supplies the water 28 to the unit main body 21, collects the water 28 that has passed through the unit main body 21, cools the water 28, and supplies the water 28 to the unit main body 21 again.
  • the cooler 24 has functions of a supply unit that supplies the water 28 to the unit main body 21, a recovery unit that recovers the water 28 from the unit main body 21, and a cooling unit that cools down.
  • the water 28 circulates between the cooler 24 and the unit main body 21, and the temperature of the reaction target liquid 11 in the unit main body 21 is adjusted by this circulation. Does not rise, and the photoreaction easily proceeds.
  • the details of the reaction unit 14 will be described later using another drawing.
  • the pipe L1 connected to the cooler 24 branches into a pipe L2 and a pipe L3 at a branch part PS1.
  • the pipe L2 is connected to the light source unit 13 side of the unit main body 21, and the pipe L3 is connected to the side opposite to the light source unit 13 side of the unit main body 21 (hereinafter, referred to as a back side).
  • the connection position of the pipe L2 and the pipe L3 is preferably at the lower part of the light source unit 13, and this is also the case in this example.
  • the supply port S2 and the supply port S3 (see FIG. 3) formed at the lower part of the housing 27 are connection portions between the pipes L5 and L6.
  • the pipe L4 connected to the cooler 24 is branched into a pipe L5 and a pipe L6 at a branch part PS2.
  • the pipe L5 is connected to the light source unit 13 side of the unit main body 21, and the pipe L6 is connected to the back side of the unit main body 21.
  • the connection position of the pipe L5 and the pipe L6 is preferably at the upper part of the light source unit 13, which is also the case in this example.
  • the discharge port D2 and the supply port D3 (see FIG. 3) formed in the upper part of the housing 27 are connection portions between the pipes L4 and L5.
  • the light source unit 13 includes a plurality of light sources 17 and a support plate 18 that supports the light sources 17.
  • a planar emission surface 13a is formed by arranging the plurality of light sources 17 on one surface of the support plate 18, and the emission surface 13a in this example is planar.
  • each light source 17 is embedded in the support plate 18, and each light source 17 and the support plate 18 are flush.
  • the mode of installing the light sources 17 on the support plate 18 is not limited to this example as long as the emission surface 13a is formed in a planar shape.
  • each light source 17 is provided in a state protruding from the surface of the support plate 18. May be.
  • the light source 17 is an LED (Light Emitting Diode, light emitting diode) in this example, and the plurality of light sources 17 are arranged in a square as shown in FIG.
  • the light source is not limited to the LED, and is appropriately selected according to the photoreactive compound to be photoreacted.
  • the light source may be, for example, a high-pressure mercury lamp, a xenon lamp, a metal halide lamp, or the like.
  • the plurality of light sources 17 are not limited to a square arrangement, but may be another regular arrangement such as a matrix arrangement, or may be an irregular arrangement. Further, in FIG. 2, the light source 17 is illustrated with 16 columns in the horizontal direction (on the paper surface) and 15 rows (in the vertical direction on the paper surface). Not limited.
  • the light source unit 13 includes a controller (not shown) for turning on and off each light source 17 and adjusting the output when the light source 17 is on, and adjusts the illuminance on the reaction target liquid 11.
  • the length WE (hereinafter, referred to as an emission width) of a region of the emission surface 13a from which light is emitted in the width direction Y is not particularly limited.
  • the length W27a (refer to FIG. 1) of the opening 27a in the width direction Y (hereinafter, referred to as opening width) may be equal to or larger than the opening width W27a.
  • the width is larger than the opening width W27a.
  • the length from one end to one end of the plurality of light sources 17 arranged in the width direction Y is defined as the emission width WE.
  • the reaction unit 14 is configured by combining a plate-shaped member for forming a flow path of the reaction target liquid 11 and / or the water 28, the housing 27, and the like.
  • the third plate-shaped member 43, the first plate-shaped member 41, the second plate-shaped member 42, and the fourth plate-shaped member 44 are arranged in this order from the light source unit 13 side and face each other with a gap therebetween. And are provided inside the housing 27 in a state parallel to each other and in a vertical posture. Note that if the angle between the opposing surfaces is within 0.06 °, the surfaces may be regarded as parallel.
  • the first plate-like member 41 to the fourth plate-like member 44 are for forming a flow path of the reaction target liquid 11 and / or water 28, and therefore, the reaction target liquid 11 and / or water 28 leak out. It is fixed to the inner wall of the housing 27 in a state where it does not exist.
  • the first plate member 41 to the fourth plate member 44 have sufficient strength not to be broken by the pressure of the reaction target liquid 11 and / or the water 28.
  • the first plate-shaped member 41 and the second plate-shaped member 42 are for flowing the liquid 11 to be reacted in a planar shape (flat film shape), and together with the housing 27, a reaction section 47 for reacting the liquid 11 to be reacted. Is configured.
  • the first plate-shaped member 41 and the second plate-shaped member 42 facing each other with a gap are formed to have substantially the same size in the XY plane, and have a smaller interval than the length in the width direction Y. Thereby, a flat flow path P1 having a flat cross section is formed inside the reaction section 47 as a flow path of the reaction target liquid 11.
  • the flat flow path P1 has a planar (planar) shape in which the length WP in the width direction Y (hereinafter, referred to as the flow path width) is larger than the length TP in the thickness direction Z (hereinafter, referred to as the flow path thickness) TP. It is a channel.
  • the first plate-shaped member 41 and the second plate-shaped member 42 define a pair of opposing surfaces of the flat flow path P1, and the opposing surfaces 41a and 42a and the inner wall surface of the housing 27 are flat. It is the wall surface of the flow path P1.
  • the supply port S1 and the discharge port D1 are formed between the first plate member 41 and the second plate member 42, as shown in FIG.
  • the supply port S1 and the discharge port D1 are formed in a slit shape extending in the width direction Y, and their opening areas (areas on the YZ plane) and shapes are the cross-sectional areas and shapes of the flat flow paths on the YZ plane. It is the same as Thus, the flow of the reaction target liquid 11 is formed into a shape extending in the width direction Y, guided to the flat flow path P1, and then discharged from the flat flow path P1.
  • the reaction target liquid 11 is formed into a shape extending in the width direction Y by the supply port S1.
  • the reaction target liquid 11 extends in the width direction Y upstream of the supply port S1, that is, on the liquid sending unit 22 side. It may be formed into a shape.
  • a partition member that partitions the flat flow path P1 such as a member extending in the flow direction X is not provided. (Not installed). That is, the flat flow path P1 is formed as one space, whereby the reaction target liquid 11 flows inside the reaction section 47 without dividing the flow in the width direction Y. Compared to the case where the partition member is inside the flat flow path P1, a volume corresponding to the volume of the partition member is secured as a flow region of the reaction target liquid 11, that is, the volume efficiency is high.
  • the flat flow path P1 has no partition member, there is no decrease in the flow velocity due to the partition member. In this way, a large processing amount is ensured while suppressing an increase in the size of the apparatus.
  • the first plate-shaped member 41 and the third plate-shaped member 43 arranged closer to the light source unit 13 than the flat flow path P1 are formed of a material that transmits light from the light source 17.
  • the material of the first plate-shaped member 41 and the third plate-shaped member 43 is not particularly limited as long as the light from the light source unit 13 is transmitted.
  • glass, acrylic resin, vinyl chloride, and the like can be given.
  • the first plate-like member 41 is made of a material that is not affected by the reaction target liquid.
  • the first plate-like member 41 and the third plate-like member 43 are both made of glass.
  • the flow path width WP of the flat flow path P1 is preferably equal to or less than the opening width W27a.
  • the width is the same as W27a.
  • the second plate-like member 42 is formed of a material that is not affected by the reaction target liquid, like the first plate-like member 41, and is preferably formed of a material that reflects light from the light source unit 13. This is also the case in this example, and specifically, it is formed of Hastelloy (registered trademark).
  • the second plate-shaped member 42 only needs to reflect light at least on the facing surface 42a. Therefore, for example, the second plate-shaped member 42 may have a multilayer structure in the thickness direction Z, and a material that reflects light may be used for a layer forming the facing surface 42a.
  • the inner surface of the housing 27 that defines the flat flow path P1 is similarly formed of a material that reflects light.
  • the third plate member 43 disposed on the light source unit 13 side of the first plate member 41 and the fourth plate member 44 disposed on the back side of the second plate member 42 are connected to the cooler 24 described above. Together with (see FIG. 1), it constitutes a temperature control mechanism 48 (see FIG. 1) for adjusting the temperature of the reaction section 47.
  • the third plate-shaped member 43 and the cooler 24 are a light source side temperature control mechanism (hereinafter, referred to as a light source side temperature control mechanism) that is adjusted from the light source unit 13 side.
  • the fourth plate-shaped member 44 and the cooler 24 are a rear-side temperature control mechanism (hereinafter, referred to as a rear-side temperature control mechanism) that is adjusted from the rear side.
  • one cooler 24 constitutes both the light source side temperature control mechanism and the rear side temperature control mechanism, but the light source side temperature control mechanism and the rear side temperature control mechanism are respectively It may be constituted by a separate cooler. Therefore, the configuration of the pipe connecting the cooler and the unit body 21 is appropriately changed according to the number of the coolers and the like.
  • the water 28 is supplied between the fourth plate member 44 and the second plate member 42.
  • the cooler 24 may be replaced with a heater (not shown), and the cooler 24 and the heater may be properly used depending on the required temperature of the target reaction.
  • the third plate-like member 43 is disposed in a state of facing the first plate-like member 41 with a gap, so that a flow path (hereinafter, referred to as a water flow path) P2 of the water 28 is provided between the gaps between the third plate-like member 43 and the flat flow path. It is formed flat like P1.
  • the fourth plate-shaped member 44 is also arranged facing the second plate-shaped member 42 with a gap therebetween, so that the water flow path P3 is formed flat in the gap between each other.
  • the water flow path P2 connects the supply port S2 and the discharge port D2, and the water flow path P3 connects to the supply port S3 and the discharge port D3.
  • the water flow path is not limited to this example.
  • a tube (not shown) may be arranged in contact with the light source side surface of the first plate member 41, and the inside of the tube may be used as a water flow path.
  • the housing 27 also has an opening 27b similar to the opening 27a on the back side. However, in this example, since the rear side does not contribute to light irradiation, the opening 27b may not be provided, and the fourth plate-shaped member 44 may be formed integrally with the housing 27.
  • the flow path width WP, flow path thickness TP, and flow path length LP between the water flow path P2 and the water flow path P3 are not particularly limited. However, from the viewpoint of more reliably controlling the temperature inside the reaction section 47, the flow path width WP and the flow path length LP should be equal to or larger than the flow path width WP and the flow path length LP of the flat flow path P1. Is preferred. In this example, the water flow path P2 and the water flow path P3 are formed to have the same volume, and have a flow path width WP larger than the flat flow path P1 and a flow path length LP equal to the flat flow path. . In FIG. 3, the flow path width WP, the flow path thickness TP, and the flow path length LP are shown only for the flat flow path P1 in order to avoid complication of the drawing.
  • the flow channel thickness TP of the flat flow channel P1 is preferably in the range of 0.1 mm or more and 20 mm or less.
  • the flow channel thickness TP of the flat flow channel P1 is more preferably in a range of 0.5 mm or more and 10 mm or less, and further preferably in a range of 1 mm or more and 6 mm or less. In this example, the flow channel thickness TP of the flat flow channel P1 is 6 mm.
  • the value obtained by dividing the flow path length LP of the flat flow path P1 by the flow path width WP is at most 300.
  • the ratio determined by LP / WP is more preferably at most 100 or less, and even more preferably at most 50. In this example, it is set to 32.
  • the water 28 is an example of a heat transfer medium.
  • Other examples of the heat transfer medium include ethylene glycol, propylene glycol, silicone oil, and the like.
  • the flat flow path P1 of FIG. As shown in (2), the closer to the opposing surface 42a and the inner wall surface of the housing 27, the smaller the light irradiation amount (hereinafter, referred to as a low irradiation region) AL. That is, of the end portions in the width direction Y, the farther from the emission surface 13a in the thickness direction Z, the smaller the light irradiation amount.
  • the length WL of the low irradiation area AL in the width direction Y (hereinafter, referred to as a low irradiation area width) is constant when the flow path thickness TP is constant. Therefore, as the flow path width WP is larger, the ratio WL / WP of the low irradiation area width WL to the flow path width WP is smaller, so that the reaction target liquid 11 flowing through the flat flow path P1 is irradiated with light with a larger irradiation amount. Is preferred.
  • FIG. 4 for convenience, only the second plate-like member 42 and a part of the housing 27 of the unit main body 21 are illustrated, and the illustration of the supply port S1 and the discharge port D1 is omitted.
  • the ratio determined by WP / TP is preferably at least 3, and in this example, 10.4.
  • the ratio determined by WP / TP is more preferably in the range of 3 or more and 1000 or less, and further preferably in the range of 5 or more and 750 or less, from the viewpoint of more surely suppressing the above-mentioned effects. It is particularly preferred that it is within the range of 500 or less.
  • the reaction target liquid 11 supplied by the liquid sending unit 22 flows between the first plate-shaped member 41 and the second plate-shaped member 42 of the unit main body 21 in this example, with a vertically upward flow direction X in this example.
  • the flat flow path P1 is a planar flow path parallel to the emission surface 13a
  • the flow of the reaction target liquid 11 has a flat shape (flat film shape) facing the emission surface 13a. Therefore, compared with the conventional method such as flowing in a tube, the reaction target liquid 11 can be flowed at a larger flow rate without increasing the size of the apparatus. The amount increases. Further, since light is applied to the planar flow in a planar manner, the photoreaction proceeds in the entire region of the reaction target liquid 11 while passing through the flat flow path P1, and as a result, the product obtained by the photoreaction Is also improved.
  • the flat flow path P1 has a volume integral large volume occupied by the tube itself as compared with the case where the tubes are spread in a plane in the same volume as the flat flow path P1. . Furthermore, since the resistance of the inner wall of the long tube is not required, the pressure loss is reduced, a large flow rate is secured, and the flow rate of the reaction target liquid 11 in the flat flow path P1 is smaller than the flow rate in the tube. And uniform.
  • the processing in the flat channel P1 in which the channel width WP of the flat channel P1 is 62.5 mm, the channel thickness TP is 6 mm, and the length LP in the flow direction X (hereinafter, referred to as the channel length) is 2000 mm.
  • the first plate-like member 41 and the second plate-like member 42 are in an upright posture, specifically, a vertical posture, and since the reaction target liquid 11 is supplied from below, the air in the flat flow path P1 is exhausted. It is easily removed from the exit D1.
  • the air in the flat flow path P1 easily escapes as the liquid level of the reaction target liquid 11 rises, and the reaction target liquid in the flat flow path P1 Even if air bubbles are present in 11, air bubbles are easily removed. Therefore, disturbance of the flow of the reaction target liquid due to the mixture of bubbles is also suppressed.
  • the third plate-like member 43 and the first plate-like member 41 transmit light, light from the light source unit 13 arranged on the opposite side of the first plate-like member 41 from the second plate-like member 42 side
  • the reaction target liquid 11 passing through the flat flow path P1 is irradiated through the third plate-shaped member 43 exposed at the opening 27a and further through the first plate-shaped member 41. Since the exit surface 13a and the flow of the reaction target liquid 11 that are opposed to each other are both formed in a planar shape, light is effectively irradiated over the entire reaction target liquid 11, whereby the photoreaction proceeds reliably.
  • the second plate-like member 42 Since the second plate-like member 42 reflects light, the light transmitted through the reaction target liquid 11 in the flat flow path P1 is reflected by the facing surface 42a of the second plate-like member 42, and is irradiated on the reaction target liquid 11 again. You. As a result, the photoreaction easily proceeds.
  • the water 28 whose temperature has been adjusted by the cooler 24 is guided from the supply ports S2 and S3 to the water flow paths P2 and P3, and flows out in a planar shape (flat film shape) before being discharged from the discharge ports D2 and D3.
  • the temperature of the discharged water 28 is adjusted again by the cooler 24. Since the water flow path P2 is formed as a flat flow path similarly to the flat flow path P1, a larger flow rate of the water 28 is secured, so that the reaction section 47 is more effectively cooled.
  • the third plate-like member 43 and the fourth plate-like member 44 are in a vertical position similarly to the first plate-like member 41 and the second plate-like member 42, the air in the water flow paths P2 and P3 is discharged from the outlets D2 and D3. Easy to be excluded from. Therefore, the cooling effect is more reliably maintained.
  • the ratio determined by the ratio WP / TP is 3 or more, the photoreaction proceeds more effectively, and the desired product can be obtained in a high yield.
  • FIG. 5 there is a correlation between the ratio WP / TP and the yield.
  • the ratio WP / TP is close to 0, the yield is extremely low.
  • the ratio WP / TP at which the increasing yield is constant is 3. Therefore, it can be said that the ratio WP / TP is preferably 3 or more.
  • the processing can be performed with a low pressure loss as compared with the case where the flow rate is less than 1 mm.
  • the flow channel thickness TP of the flat flow channel P1 is equal to or less than 20 mm, sufficient illuminance can be obtained up to the deepest portion of the flat flow channel P1 (where the distance from the emission surface 13a is the longest) as compared with a case where the flow channel thickness TP exceeds 20 mm. Is irradiated with light.
  • the flat channel P1 has an LP / WP of 300 or less, it can be processed with a low pressure loss even if the flow rate is large, as compared with a case where the LP / WP exceeds 300.
  • the first plate-shaped member 41 and the second plate-shaped member 42 are arranged in a vertical posture, but the invention is not limited to the vertical posture, and may be a horizontal posture. However, from the viewpoint of obtaining the above-described air elimination effect, it is more preferable to be in the upright state than in the horizontal posture.
  • the angle ⁇ between the first plate-shaped member 41 and the horizontal line HL (where 0 ° ⁇ ⁇ ⁇ 180 °, the unit is °) is 0 ° ⁇ ⁇ .
  • the angle is preferably 180 °, more preferably 0 ° ⁇ ⁇ 90 °.
  • the angle between the second plate-shaped member 42 and the horizontal line HL is the same as the angle ⁇ .
  • the angle between each of the third plate member 43, the fourth plate member 44, and the emission surface 13a of the light source 17 and the horizontal line HL is the same as the angle ⁇ .
  • the angle ⁇ is an angle formed between the rear surface of the first plate-shaped member 41 and the horizontal line HL, as shown in FIG.
  • the second plate-like member 42 that reflects the light from the light source unit 13, that is, the irradiation light, is used, but a second plate-like member that transmits the light may be used.
  • the unit main body 61 of FIG. 7 includes a second plate-shaped member 62 that transmits irradiation light instead of the second plate-shaped member 42. Note that, in FIG. 7, the same members and the like as those in the above-described example are denoted by the same reference numerals, and description thereof will be omitted.
  • the second plate member 62 of this example is made of glass, like the first plate member 41 and the third plate member 43. Further, the unit main body 61 is provided with a reflection plate for reflecting irradiation light on the back side of the second plate-shaped member 62, thereby improving the irradiation amount to the reaction target liquid 11 flowing through the flat flow path P1. Note that, instead of the reflection plate, for example, the above-described aluminum foil may be used. In this case, since the fourth plate-shaped member 44 is provided with a gap from the rear surface of the reflection plate 63, a gap is provided between the fourth plate-shaped member 44 and the second plate-shaped member 62 via the reflection plate 63. Become. Thus, the water flow path P3 is formed between the fourth plate member 44 and the second plate member 62 via the reflection plate 63.
  • the photoreaction device 70 shown in FIG. 8 includes a unit main body 71 instead of the unit main body 21, and includes two light source units 13A and 13B. Since each of the light source units 13A and 13B is the same as the light source unit 13, the description is omitted. In the following description, when these two light source units are not distinguished, they are described as a light source unit 13. In FIG. 8, the same members and the like as those in the above-described example are denoted by the same reference numerals, and description thereof will be omitted.
  • the unit main body 71 includes the above-described second plate-shaped member 62 instead of the second plate-shaped member 42 in the unit main body 21, and includes a fourth plate-shaped member 74 instead of the fourth plate-shaped member 44.
  • the opening 27b is also used as an opening for guiding light to the flat flow path P1.
  • the unit main body 71, the light source unit 13A, and the light source unit 13B are arranged such that the light source unit 13A faces the opening 27a and the light source unit 13B faces the opening 27b.
  • the fourth plate member 74 of this example is made of glass, like the first plate member 41 and the third plate member 43. Other configurations of the fourth plate member 74 are the same as those of the fourth plate member 44.
  • the fourth plate-like member 74 faces the second plate-like member 62 with a gap, similarly to the fourth plate-like member 44 facing the second plate-like member 42 with a gap. Thereby, the water flow path P3 is formed flat by the second plate-shaped member 62 and the fourth plate-shaped member 74.
  • the flow path thickness TP of the flat flow path P1 of this example is 0.2 mm, which is twice that of each of the above examples, from the viewpoint of the progress of the photoreaction. It may be in the range of not less than 40 mm or more.
  • the above photoreaction device can be used for various photoreactions.
  • photoreactions include halogenation, reduction, cyclization, cross coupling, trifluoromethylation, and the like.
  • a photoreaction shown in FIG. 9 is mentioned as an example.
  • o-tolunitrile as a photoreactive compound is dissolved in acetonitrile as a solvent together with N-bromosuccinimide (NBS) as a reagent to obtain a reaction target liquid 11.
  • NBS N-bromosuccinimide
  • the reaction target liquid 11 is irradiated with light having a wavelength of 365 nm by an LED while adjusting the temperature to 20 ° C.
  • ⁇ -bromo-o-tolunitrile as a reaction product is obtained in a yield of 81%.

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  • Electromagnetism (AREA)
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Abstract

L'invention concerne un appareil et un procédé de photoréaction grâce auxquels le débit est amélioré tout en supprimant une augmentation de la taille de l'appareil. L'appareil de photoréaction comprend une unité de réaction (47), une unité de source de lumière (13) et un refroidisseur (24), et réalise une photoréaction par irradiation d'un liquide à faire réagir avec un faisceau de lumière tout en faisant circuler le liquide à faire réagir, le liquide contenant un composé photoréactif. Un canal d'écoulement plat (P1) est formé à l'intérieur de l'unité de réaction (47) par un premier élément de plaque (41) et des seconds éléments de plaque (42, 62). L'unité de source de lumière (13) a une pluralité de sources de lumière agencées selon une forme plane, et est disposée sur un côté du premier élément de plaque (41), qui est opposé aux seconds éléments de plaque (42, 62). Le refroidisseur (24) règle la température de l'unité de réaction (47) à partir du côté de l'unité de source de lumière (13).
PCT/JP2019/024967 2018-07-17 2019-06-24 Appareil et procédé de photoréaction WO2020017246A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03500531A (ja) * 1987-06-25 1991-02-07 ベイラー、リサーチ、インスチテュート 体組織中の感染性生物学的汚染菌の排除方法
GB2248835A (en) * 1990-10-16 1992-04-22 Dow Stade Gmbh Process for preparing 1,1,1-trichloroethane
JP2002512209A (ja) * 1998-04-17 2002-04-23 シュトゥディエンゲゼルシャフト・コーレ・ミット・ベシュレンクテル・ハフツング 平床型太陽光コレクター／ソーラー・リアクターを用いる光化学および熱化学的ソーラー合成
JP2003200043A (ja) * 2002-01-04 2003-07-15 Tasuke Iwashita 有機ｅｌ素子または無機ｅｌ素子を用いた有機物質分解装置
JP2004523607A (ja) * 2000-12-21 2004-08-05 チバ　スペシャルティ　ケミカルズ　ウォーター　トリートメント　リミテッド 同軸シリンダをもつ管状反応器及び同反応器を使用する方法
WO2016056371A1 (fr) * 2014-10-09 2016-04-14 東レ株式会社 Dispositif de réaction photochimique, procédé de réaction photochimique l'utilisant, et procédé de production de lactone au moyen dudit procédé
JP2017127283A (ja) * 2016-01-22 2017-07-27 株式会社日立製作所 培養生産物の処理装置、培養生産物の処理方法、及び培養生産物の精製装置

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03500531A (ja) * 1987-06-25 1991-02-07 ベイラー、リサーチ、インスチテュート 体組織中の感染性生物学的汚染菌の排除方法
GB2248835A (en) * 1990-10-16 1992-04-22 Dow Stade Gmbh Process for preparing 1,1,1-trichloroethane
JP2002512209A (ja) * 1998-04-17 2002-04-23 シュトゥディエンゲゼルシャフト・コーレ・ミット・ベシュレンクテル・ハフツング 平床型太陽光コレクター／ソーラー・リアクターを用いる光化学および熱化学的ソーラー合成
JP2004523607A (ja) * 2000-12-21 2004-08-05 チバ　スペシャルティ　ケミカルズ　ウォーター　トリートメント　リミテッド 同軸シリンダをもつ管状反応器及び同反応器を使用する方法
JP2003200043A (ja) * 2002-01-04 2003-07-15 Tasuke Iwashita 有機ｅｌ素子または無機ｅｌ素子を用いた有機物質分解装置
WO2016056371A1 (fr) * 2014-10-09 2016-04-14 東レ株式会社 Dispositif de réaction photochimique, procédé de réaction photochimique l'utilisant, et procédé de production de lactone au moyen dudit procédé
JP2017127283A (ja) * 2016-01-22 2017-07-27 株式会社日立製作所 培養生産物の処理装置、培養生産物の処理方法、及び培養生産物の精製装置

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