WO2021224980A1 - Colonne pour la synthèse d'écoulement et procédé de synthèse d'écoulement - Google Patents

Colonne pour la synthèse d'écoulement et procédé de synthèse d'écoulement Download PDF

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Publication number
WO2021224980A1
WO2021224980A1 PCT/JP2020/018630 JP2020018630W WO2021224980A1 WO 2021224980 A1 WO2021224980 A1 WO 2021224980A1 JP 2020018630 W JP2020018630 W JP 2020018630W WO 2021224980 A1 WO2021224980 A1 WO 2021224980A1
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Prior art keywords
cylinder
flow
flow synthesis
catalyst
cells
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PCT/JP2020/018630
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English (en)
Japanese (ja)
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貴士 横山
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日本碍子株式会社
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Priority to PCT/JP2020/018630 priority Critical patent/WO2021224980A1/fr
Priority to JP2022519872A priority patent/JPWO2021224980A1/ja
Publication of WO2021224980A1 publication Critical patent/WO2021224980A1/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

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  • the present invention relates to a flow synthesis column and a flow synthesis apparatus.
  • the method of synthesizing a product from a plurality of reactants is roughly classified into a method of synthesizing by batch synthesis and a method of synthesizing by flow synthesis.
  • a liquid containing the plurality of reactants and a catalyst are placed in a reaction vessel.
  • the plurality of reactants are reacted inside the reaction vessel. This produces a product and, in many cases, a by-product.
  • steam, cold water or a refrigerant is passed through the reaction vessel to heat or cool the liquid.
  • a plurality of reactants are brought into contact with the catalyst.
  • the liquid containing the product, by-product and catalyst is discharged from the reaction kettle. Products, by-products and catalysts are separated by filtration, isolation and the like. This gives the desired product. The separated catalyst is often discarded.
  • a liquid containing the plurality of reactants is allowed to flow into the flow synthesis column. Multiple reactants are reacted inside a flow synthesis column. This produces a product and, in many cases, a by-product.
  • the outer peripheral surface of the flow synthesis column is heated or cooled to heat or cool the liquid.
  • a plurality of reactants are brought into contact with a catalyst supported on a carrier provided in a flow synthesis column. The liquid containing the product and by-product is flushed from the flow synthesis column. The product and by-product are separated by filtration, isolation, etc. This gives the desired product.
  • Flow synthesis has the advantage that the process of separating the catalyst can be omitted compared to batch synthesis. Further, the flow synthesis has an advantage that the waste of the catalyst can be suppressed as compared with the batch synthesis. In addition, flow synthesis has an advantage that products can be continuously produced as compared with batch synthesis. In addition, flow synthesis has the advantage that the cost of energy for heating or cooling the liquid can be suppressed as compared with batch synthesis.
  • Patent Document 1 discloses a continuous flow multi-step synthesizer (paragraph 0029).
  • the continuous flow multi-step synthesizer comprises a column packed with a solid phase carrier (paragraph 0029).
  • the temperature of the column can be adjusted by a constant temperature bath (paragraph 0025).
  • the heat transfer in the radial direction depends on the heat transfer between the carriers and the heat transfer by the liquid.
  • heat transfer between carriers and heat transfer by liquids are not sufficient. Therefore, in the flow synthesis column, it is difficult to make the temperature distribution in the in-cylinder space uniform in the radial direction. For example, when the reaction for synthesizing a product from a plurality of reactants is an exothermic reaction or when the outer peripheral surface of the flow synthesis column is cooled, the temperature at the radial center of the in-cylinder space becomes relatively high. , The temperature of the radial peripheral part of the in-cylinder space becomes relatively low.
  • the reaction for synthesizing a product from a plurality of reactants is an endothermic reaction or when the outer peripheral surface of the flow synthesis column is heated, the temperature at the radial center of the in-cylinder space is relatively low. Therefore, the temperature of the radial peripheral portion of the in-cylinder space becomes relatively high. If the temperature distribution in the in-cylinder space cannot be made uniform in the radial direction of the flow synthesis column, the yield of the product decreases and the amount of by-product produced increases.
  • An object of the present invention is to provide a flow synthesis column capable of making the temperature distribution in the in-cylinder space uniform in the radial direction.
  • the present invention relates to a column for flow synthesis.
  • the flow synthesis column is equipped with a cylinder, a wall and a catalyst.
  • the cylinder has a space inside the cylinder.
  • the wall divides the space inside the cylinder into multiple cells extending in the axial direction of the cylinder.
  • the catalyst is exposed inside each of the multiple cells.
  • the present invention is also directed to a flow synthesis apparatus including the flow synthesis column.
  • the wall increases the heat exchange area between the liquid and the flow synthesis column. Therefore, heat can be efficiently transferred in the radial direction via the wall.
  • the temperature of the in-cylinder space can be brought close to the temperature suitable for the chemical reaction. As a result, the reaction rate of the chemical reaction in the in-cylinder space can be increased.
  • the yield of the product can be increased.
  • the amount of by-products produced can be suppressed.
  • FIG. 1 It is a figure which illustrates typically the flow synthesis apparatus of 1st Embodiment. It is a perspective view which shows typically the column for flow synthesis of 1st Embodiment. It is sectional drawing which shows typically the column for flow synthesis of 1st Embodiment. It is a vertical cross-sectional view which shows typically the column for flow synthesis of 1st Embodiment. It is a graph which shows the change of the concentration of the raw material A, the raw material B, the raw material C, and the product by the distance from the inflow port in the flow synthesis column of 1st Embodiment. It is a vertical cross-sectional view which shows typically the flow synthesis column of the 1st modification of 1st Embodiment.
  • FIG. 5 is a cross-sectional view schematically showing a flow synthesis column of Comparative Example 1. It is a figure which schematically explains the model used for the simulation of Examples 1 and 2.
  • FIG. 1 is a diagram schematically illustrating the flow synthesizer of the 1st embodiment.
  • the flow synthesizer 1 of the first embodiment includes a mixer 11, a flow synthesis column 12, and a temperature controller 13.
  • the mixer 11 mixes a plurality of reactants 21 to produce a liquid 22 containing the plurality of reactants 21. Further, the mixer 11 causes the generated liquid 22 to flow into the flow synthesis column 12.
  • the plurality of reactants 21 are three kinds of raw materials A, B and C.
  • the plurality of reactants 21 may be two kinds of raw materials or four or more kinds of raw materials.
  • the liquid 22 may contain a plurality of substances other than the reactants 21.
  • the liquid 22 may contain a solvent.
  • the flow synthesis column 12 synthesizes the product 23 by reacting a plurality of reactants 21 contained in the inflowing liquid 22 with each other.
  • the flow synthesis column 12 drains the liquid containing the synthesized product 23.
  • the temperature controller 13 adjusts the temperature of the flow synthesis column 12. As a result, the temperature of the liquid 22 flowing into the flow synthesis column 12 is adjusted to a temperature suitable for a chemical reaction in which a plurality of reactants 21 are reacted to synthesize the product 23.
  • the temperature controller 13 has at least one function of a heater for heating the flow synthesis column 12 and a cooler for cooling the flow synthesis column 12.
  • the heater is an electric resistance heater that performs electric heating, a heat medium heater that circulates a heat medium such as steam or oil, and heats the heat medium.
  • the cooler is an electronic cooling cooler that performs electronic cooling by utilizing the Pertier effect, a cooler that circulates cold water or a refrigerant to perform cooling, and the like.
  • FIG. 2 is a perspective view schematically illustrating the flow synthesis column of the first embodiment.
  • FIG. 3 is a cross-sectional view schematically showing the flow synthesis column of the first embodiment.
  • FIG. 4 is a vertical cross-sectional view schematically showing the flow synthesis column of the first embodiment.
  • the flow synthesis column 12 includes a cylinder 31.
  • the cylinder 31 has an in-cylinder space 41.
  • the cylinder 31 is a cylinder.
  • the in-cylinder space 41 is an in-cylinder space.
  • the cylinder 31 may be a cylinder other than a cylinder.
  • the in-cylinder space 41 may be an in-cylinder space other than the in-cylinder space.
  • the cylinder 31 may be a square cylinder.
  • the in-cylinder space 41 may be a square in-cylinder space.
  • the temperature of the outer peripheral surface 31a of the cylinder 31 is adjusted by the temperature controller 13.
  • the flow synthesis column 12 includes a wall 32.
  • the wall 32 divides the in-cylinder space 41 into a plurality of cells 42.
  • the plurality of cells 42 extend in the axial direction DZ of the cylinder 31.
  • the plurality of cells 42 are arranged in a direction perpendicular to the axial direction DZ.
  • the plurality of cells 42 are preferably evenly arranged.
  • the wall 32 divides the in-cylinder space 41 in a grid pattern.
  • the wall 32 may partition the in-cylinder space 41 in a non-grid pattern.
  • the wall 32 may partition the in-cylinder space 41 in a honeycomb shape.
  • the wall 32 is continuous from the cylinder 31.
  • the flow synthesis column 12 includes a catalyst 33 and a carrier 34.
  • the catalyst 33 is exposed inside each of the plurality of cells 42.
  • the catalyst 33 is a catalyst that accelerates the reaction rate of a chemical reaction in which a plurality of reactants 21 are reacted to synthesize a product 23.
  • the catalyst 33 is supported on the surface of the carrier 34 inside each of the plurality of cells 42.
  • the carrier 34 is arranged inside each of the plurality of cells 42.
  • the carrier 34 carries the catalyst 33.
  • the carrier 34 has a spherical shape.
  • the carrier 34 is made of silica, polymer, alumina or the like.
  • the liquid 22 is made to flow into the inflow port which is one end of the in-cylinder space 41.
  • the inflowed liquid 22 is flowed into the in-cylinder space 41.
  • the flowed liquid 22 is discharged from the outlet which is the other end of the in-cylinder space 41.
  • the liquid 22 is flowed into the in-cylinder space 41, it is flowed into each of the plurality of cells 42.
  • the liquid 22 comes into contact with the catalyst 33 arranged inside each of the plurality of cells 42.
  • the reaction rate of the above-mentioned chemical reaction becomes faster.
  • the radial peripheral portion of the tubular space 41 is moved to the radial central portion of the tubular space 41.
  • Heat H can be efficiently transferred toward the surface. Therefore, the wall 32 can function as a good thermalization structure, and the flow synthesis column 12 can function as a good heat exchanger.
  • the temperature distribution of the in-cylinder space 41 can be made uniform in the radial DR.
  • the distribution of the reaction rate of the chemical reaction in the in-cylinder space 41 can be made uniform in the radial DR.
  • the temperature of the in-cylinder space 41 can be brought close to the temperature suitable for the above-mentioned chemical reaction. Thereby, the reaction rate of the above-mentioned chemical reaction can be increased.
  • the yield of product 23 can be increased.
  • the amount of by-products produced can be suppressed.
  • the wall 32 has physical characteristics and mechanical properties suitable for exerting this advantage.
  • the wall 32 is preferably made of a material having a high heat transfer coefficient and a low specific heat from the viewpoint of physical characteristics. Further, from the viewpoint of mechanical properties, the wall 32 has a structure having a wide heat exchange area without obstructing the flow of the liquid 22 and increasing the pressure loss when the liquid 22 flows through each of the plurality of cells 42. It is made of a material that has high corrosion resistance.
  • the wall 32 is made of, for example, ceramics. Ceramics are silicon carbide, alumina, aluminum nitride and the like.
  • the carrier 34 is arranged inside each of the plurality of cells 42, the liquid 22 flows between the carriers 34 and the flow of the liquid 22 is disturbed. Therefore, the chance of contact between the plurality of reactants 21 and the catalyst 33 can be increased. Thereby, the above-mentioned chemical reaction can be further advanced.
  • the carrier 34 carrying the catalyst 33 is arranged inside each of the plurality of cells 42, the specific surface area of the catalyst 33 becomes large. Therefore, the chance of contact between the plurality of reactants 21 and the catalyst 33 can be increased. Thereby, the above-mentioned chemical reaction can be further advanced.
  • the in-cylinder space 41 is partitioned by the wall 32 and the carrier 34 is arranged inside each of the plurality of cells 42, the liquid 22 flows between the carriers 34 and the flow of the liquid 22 is disturbed. Therefore, the chance of contact between the liquid 22 and the wall 32 can be increased. Therefore, the frequency of heat exchange between the liquid 22 and the wall 32 can be increased. As a result, heat can be efficiently transferred to the radial DR via the wall 32.
  • the catalyst 33 When the catalyst 33 is exposed inside each of the plurality of cells 42, the catalyst 33 can be cleaned by flowing a cleaning agent such as nitric acid or hydrochloric acid into each of the plurality of cells 42. Therefore, it is possible to suppress the disposal of the catalyst 33.
  • a cleaning agent such as nitric acid or hydrochloric acid
  • the temperature controller 13 makes the temperature distribution on the outer peripheral surface 31a of the cylinder 31 uniform in the axial direction DZ.
  • the temperature controller 13 may make the temperature distribution on the outer peripheral surface 31a of the cylinder 31 uneven in the axial direction DZ.
  • the temperature controller 13 has a temperature T1 on the outer peripheral surface 31a of the cylinder 31 at the position P1 in the axial direction DZ, a temperature T2 on the outer peripheral surface 31a of the cylinder 31 at the position P2 in the axial direction DZ, and a cylinder at the position P3 in the axial direction DZ.
  • the temperatures T3 of the outer peripheral surface 31a of 31 may be different from each other.
  • FIG. 5 shows changes in the concentrations of raw material A, raw material B, raw material C, and product depending on the distance from the inflow port in the flow synthesis column of the first embodiment.
  • the progress of the chemical reaction for synthesizing the product 23 by reacting the raw material A, the raw material B, and the raw material C increases as the distance from the inflow port increases. Therefore, as shown in FIG. 5, the concentrations of the raw materials A, B, and C decrease as the distance from the inflow port increases. Further, as shown in FIG. 5, the concentration of the product 23 increases as the distance from the inflow port increases. Further, the heat generation or endothermic due to the above-mentioned chemical reaction becomes smaller as the distance from the inflow port increases. Therefore, the temperature of the outer peripheral surface 31a of the cylinder 31 suitable for advancing the above-mentioned chemical reaction changes according to the distance from the inflow port.
  • the temperature of the outer peripheral surface 31a of the cylinder 31 becomes a temperature suitable for advancing the above-mentioned chemical reaction.
  • the temperature of the outer peripheral surface 31a of the cylinder 31 is adjusted in this way.
  • FIG. 6 is a vertical cross-sectional view schematically showing a flow synthesis column of the first modification of the first embodiment.
  • the flow synthesis column 12m of the first modification of the first embodiment shown in FIG. 6 can replace the flow synthesis column 12 of the first embodiment shown in FIGS. 2, 3 and 4. ..
  • the flow synthesis column 12m is different from the flow synthesis column 12 in the points described below. Regarding points not described below, the same configuration as that adopted in the flow synthesis column 12 is also adopted in the flow synthesis column 12m.
  • the wall 32 is provided in the entire axial direction DZ.
  • the wall 32 is provided in the first section S1 in the axial direction DZ and is arranged alternately with the first section S1. It is not provided in the second section S2 in the axial direction DZ.
  • the liquids 22 flowed into the plurality of cells 42 in the first section S1 are mixed and stirred in the second section S2 following the first section S1.
  • the concentration difference caused by the minute reaction rate difference in the plurality of cells 42 caused by the temperature difference inside the plurality of cells 42 can be eliminated, and the yield can be further improved.
  • FIG. 7 is a cross-sectional view schematically showing a flow synthesis column of the second modification of the first embodiment.
  • FIG. 8 is a cross-sectional view schematically showing a flow synthesis column of a third modification of the first embodiment.
  • FIG. 9 is a cross-sectional view schematically showing a flow synthesis column of the fourth modification of the first embodiment.
  • FIG. 7 shows the flow synthesis column 12A of the second modification of the first embodiment shown in FIG. 7, the flow synthesis column 12B of the third modification of the first embodiment shown in FIG. 8, and FIG.
  • the flow synthesis column 12C of the fourth modification of the first embodiment can replace the flow synthesis column 12 of the first embodiment shown in FIGS. 2, 3 and 4.
  • the flow synthesis columns 12A, 12B and 12C are different from the flow synthesis columns 12 in the following points. Regarding points not described below, the same configuration as that adopted in the flow synthesis column 12 is also adopted in the flow synthesis columns 12A, 12B and 12C.
  • the catalyst 33 exposed inside each of the plurality of cells 42 is the carrier 34 inside each of the plurality of cells 42. It is supported on the surface.
  • the catalyst 33 exposed inside each of the plurality of cells 42 is supported on the surface of the cylinder 31 and / or the wall 32. It constitutes a catalyst layer.
  • the cylinder 31 and / or the wall 32 includes a base material 50 and a catalyst 51 dispersed in the base material 50, and has a plurality of cells 42.
  • the catalyst 33 exposed inside each is a part of the catalyst 51.
  • the cylinder 31 and / or the wall 32 constituting the flow synthesis column 12B can be manufactured through a step of mixing the catalyst 51 with the base material 50 to obtain a mixture and molding the obtained mixture.
  • the cylinder 31 and / or the wall 32 is composed of the catalyst 51, and the catalyst 33 exposed inside each of the plurality of cells 42 is the catalyst 51. Is part of.
  • the cylinder 31 and / or the wall 32 constituting the flow synthesis column 12C can be manufactured through a step of molding a catalyst.
  • the flow synthesis column 12A has an advantage that the amount of the catalyst 33 can be reduced and the entire catalyst 33 can be exposed inside each of the plurality of cells 42 as compared with the flow synthesis columns 12B and 12C.
  • the flow synthesis columns 12B and 12C can eliminate the catalyst layer, improve the density of the cells 42 per unit area, and separate the adjacent cells 42 from the partition walls, as compared with the flow synthesis columns 12A. It has the advantage that the thickness can be reduced.
  • Example 2 Comparison by simulation In Example 1, the in-cylinder space 41 when organic synthesis was performed inside the flow synthesis column 12 provided with the cylinder 31 having a thermal conductivity of 160 W / m ⁇ K and the wall 32. The temperature distribution was analyzed by simulation. The thermal conductivity of 160 W / m ⁇ K corresponds to the thermal conductivity of silicon carbide.
  • Example 2 the temperature distribution of the in-cylinder space 41 when organic synthesis is performed inside the flow synthesis column 12 including the cylinder 31 having a thermal conductivity of 30 W / m ⁇ K and the wall 32 is simulated. Analyzed. The thermal conductivity of 30 W / m ⁇ K corresponds to the thermal conductivity of alumina.
  • FIG. 10 is a vertical cross-sectional view schematically showing the flow synthesis column of Comparative Example 1.
  • the flow synthesis column 92 of Comparative Example 1 shown in FIG. 10 is different from the flow synthesis column 12 of the first embodiment shown in FIGS. 2, 3 and 4 in that the wall 32 is not provided. ..
  • FIG. 11 is a diagram schematically illustrating the models used in the simulations of Examples 1 and 2.
  • a model conforming to the model described with reference to FIG. 11 was used.
  • the temperature distribution of the fan-shaped region 61 which occupies 1/4 of the two-dimensional cross section of the flow synthesis column 12 perpendicular to the axial direction DZ and has a central angle of 90 ° is used. Analyzed. Further, in the simulation, the temperature distribution of the fan-shaped region 61 in the steady state when the heat generated by the above-mentioned chemical reaction in the fan-shaped region 61 was uniform and the outer peripheral surface 31a of the cylinder 31 was cooled to 20 ° C. was analyzed. Moreover, in the simulation, the influence of the catalyst 33 was not considered in order to facilitate the analysis.
  • the diameter of the cylinder 31 is 10 mm
  • the heat transfer coefficient h outside the outer peripheral surface 31a of the cylinder 31 is 100 W / m 2 ⁇ K
  • the thermal conductivity ⁇ of the object arranged in the cylinder inner space 41 is uniform. It was set to 1 W / m ⁇ K
  • the calorific value Q in the in-cylinder space 41 was set to 3.62 ⁇ 10 6 W / m 2 .
  • the heat transfer coefficient h of 100 W / m 2 ⁇ K is the minimum value of the heat transfer coefficient when the liquid is forcibly convected.
  • the thermal conductivity ⁇ of 1 W / m ⁇ K is the product of the thermal conductivity ⁇ 1 of the carrier 34 and the ratio ⁇ 1 of the area occupied by the carrier 34 ⁇ 1 ⁇ ⁇ 1, and the thermal conductivity ⁇ 2 of the liquid 22 and the liquid. 22 the product ⁇ 2 ⁇ ⁇ 2 between the ratio epsilon 2 of the area occupied by the sum ⁇ 1 ⁇ ⁇ 1 + ⁇ 2 ⁇ ⁇ 2 of.
  • the calorific value Q of 3.62 ⁇ 10 6 W / m 2 is the calorific value when the heat generated in the fan-shaped region 61 is up to 70 ° C. The temperature of 70 ° C. was determined from the typical heat generation in organic synthesis.
  • Table 1 shows the maximum temperature and the minimum temperature indicating the temperatures of the maximum temperature point PH1 and the minimum temperature point PL1 shown in FIG. 3 in Examples 1 and 2, respectively.
  • Table 1 shows the temperature difference indicating the difference between the maximum temperature and the minimum temperature.
  • Table 1 shows the maximum temperature and the minimum temperature indicating the temperatures of the maximum temperature point PH2 and the minimum temperature point PL2 shown in FIG. 10 in Comparative Example 1, respectively.
  • Table 1 shows the temperature difference indicating the difference between the maximum temperature and the minimum temperature.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)

Abstract

L'invention concerne une colonne pour la synthèse d'écoulement avec laquelle la distribution de température dans la direction radiale d'un espace dans le cylindre peut être rendue uniforme. La colonne de synthèse d'écoulement est pourvue d'un cylindre, d'une paroi et d'un catalyseur. Le cylindre comporte un espace interne dans le cylindre. La paroi divise l'espace interne du cylindre en une pluralité de cellules s'étendant dans la direction axiale du cylindre. Le catalyseur est exposé à l'intérieur de chacune de la pluralité de cellules.
PCT/JP2020/018630 2020-05-08 2020-05-08 Colonne pour la synthèse d'écoulement et procédé de synthèse d'écoulement WO2021224980A1 (fr)

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PCT/JP2020/018630 WO2021224980A1 (fr) 2020-05-08 2020-05-08 Colonne pour la synthèse d'écoulement et procédé de synthèse d'écoulement
JP2022519872A JPWO2021224980A1 (fr) 2020-05-08 2020-05-08

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030012711A1 (en) * 1999-11-17 2003-01-16 Conoco Inc. Honeycomb monolith catalyst support for catalytic distillation reactor
JP2007500601A (ja) * 2003-07-30 2007-01-18 コーニング インコーポレイテッド 化学および熱用途のための金属ハニカム基体
JP2012501240A (ja) * 2008-06-27 2012-01-19 ユミコア・アクチエンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト 高い選択率及び収率で不均一系触媒反応を実施するための方法
JP2013533369A (ja) * 2010-08-09 2013-08-22 ビーエーエスエフ ソシエタス・ヨーロピア ポリエーテルアルコールを製造する方法
JP2015172025A (ja) * 2014-03-11 2015-10-01 東京化成工業株式会社 連続的フロー多段階反応による医薬品の製造方法
JP2018015695A (ja) * 2016-07-26 2018-02-01 ニッポン高度紙工業株式会社 管状の触媒システムおよびそれを使用した化学反応装置、管状の触媒システムの製造方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030012711A1 (en) * 1999-11-17 2003-01-16 Conoco Inc. Honeycomb monolith catalyst support for catalytic distillation reactor
JP2007500601A (ja) * 2003-07-30 2007-01-18 コーニング インコーポレイテッド 化学および熱用途のための金属ハニカム基体
JP2012501240A (ja) * 2008-06-27 2012-01-19 ユミコア・アクチエンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト 高い選択率及び収率で不均一系触媒反応を実施するための方法
JP2013533369A (ja) * 2010-08-09 2013-08-22 ビーエーエスエフ ソシエタス・ヨーロピア ポリエーテルアルコールを製造する方法
JP2015172025A (ja) * 2014-03-11 2015-10-01 東京化成工業株式会社 連続的フロー多段階反応による医薬品の製造方法
JP2018015695A (ja) * 2016-07-26 2018-02-01 ニッポン高度紙工業株式会社 管状の触媒システムおよびそれを使用した化学反応装置、管状の触媒システムの製造方法

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