JP2011183311A - Method and apparatus for producing chemical reaction product - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method and apparatus for producing a chemical reaction product, which accurately control rapid generation of reaction heat even when a diameter of a reaction flow path or concentration of a raw material liquid is increased in order to perform high flow rate treatment, thereby attaining yield improvement of an objective reaction product and industrialization. <P>SOLUTION: In the apparatus for producing a chemical reaction product, when two or more raw material liquids are made to join together at a confluence part of the reaction flow paths from respective supply paths and are caused to perform exothermic reaction, production of byproducts except an objective reaction product due to influence of reaction heat is suppressed. The apparatus 10 includes: a dividing means 12 which divides at least one raw material liquid among two or more raw material liquids L1, L2 and forms a double layer flow L in which raw material liquids L1, L2 are alternately arranged, at the confluence part 24A of the reaction flow paths 24, thereby making the raw material liquids L1, L2 react with each other in a thin layer state; an external cooling means 22 for cooling from outside of the reaction flow paths 24; and an internal cooling means 20 for cooling center fluid flowing at least at a center part among the double laminar flow L in advance before being jointed to the reaction flow paths 24. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to a method and apparatus for producing a chemical reactant, and in particular, a chemical reactant that suppresses generation of a side reactant other than a target reactant due to a side reaction caused by the influence of reaction heat accompanied by a sudden exotherm. The present invention relates to a manufacturing method and a manufacturing apparatus.

  Examples of the exothermic reaction accompanied by a rapid exotherm due to reaction heat include a halogen-lithium exchange reaction, a nitration reaction, and a polymerization reaction. Among them, for example, a lithium compound produced by using a halogen-lithium exchange reaction is a substance useful for industrial use as an intermediate in the synthesis of a high-value-added final product. Manufactured in various fields such as photography and dyestuffs.

  However, in the halogen-lithium exchange reaction, the reactivity of the lithium compound as the target reactant is high, and it is an exothermic reaction accompanied by a rapid exotherm due to the heat of reaction. Side reaction products are easily generated. Therefore, it is necessary to precisely control the heat of reaction so that excessive reaction does not occur.

  From this, the halogen-lithium exchange reaction has been accompanied by rapid heat generation by suppressing heat generation by dropping a droplet of one raw material liquid into the other raw material liquid under an ultra-low temperature condition of -78 ° C. The reaction heat is controlled.

  However, since the conventional dripping method requires an ultra-low temperature facility, there is a problem in terms of facility cost and running cost. In addition, the dropping method requires a long time for the dropping reaction time, and the lithium compound that is a target reactant that is unstable to heat tends to deteriorate, and the generated target reactant reacts with an unreacted raw material liquid. There is a problem that by-products are easily generated.

  That is, in order to suppress the formation of by-products due to the influence of the exothermic reaction, it is important to finish the reaction in a short time (instantaneous reaction) in addition to precisely controlling the heat of reaction.

For this reason, Patent Document 1 proposes a production method in which an ultra-low temperature facility is not required and a halogen-lithium exchange reaction is performed at low cost. In the manufacturing method of Patent Document 1,
A halogen compound and an organic lithium reagent are reacted with each other using at least one continuous reactor such as a microreactor having excellent heat exchange efficiency. Thereby, even if it cools on the comparatively gentle cooling conditions from the exterior of a microreactor, since rapid heat_generation | fever by reaction heat can be suppressed, it is supposed that a lithium compound can be obtained with a high yield. That is, the method of Patent Document 1 uses the good heat exchange efficiency of the microreactor and the feature that allows instantaneous reaction to obtain the target reactant in a high yield.

JP 2005-104871 A

  However, in the case of Patent Literature 1, since the diameter of the reaction channel must be reduced in order to ensure good heat transfer, the raw material liquid cannot be flowed at a high flow rate, and the throughput is not increased. There is a problem. The amount of treatment can also be increased by increasing the concentration of the raw material liquid, but if high concentration raw material liquids are reacted with each other, the temperature control becomes difficult with more rapid heat generation. Therefore, the method of Patent Document 1 is difficult to apply to industrialization where productivity is regarded as important.

  The characteristics of the microreactor are that the diameter of the reaction channel is small and the contact area between the reaction channel wall and the fluid flowing through the reaction channel is large, so that heat exchange efficiency is good even when cooling from the outside of the reaction channel It is. However, if the flow path diameter is increased for mass production, the heat transfer area changes to the second power and the volume changes to the third power. Therefore, there is a problem that the heat exchange efficiency is rapidly deteriorated and the scale cannot be increased. As a countermeasure, a method of numbering up to increase the number of microreactors has been proposed, but in order to scale up laboratory scale microreactors to industrial scale, it is necessary to prepare thousands or tens of thousands of microreactors, Not realistic.

  The present invention has been made in view of such circumstances, and in order to perform high flow rate processing, even if the diameter of the reaction channel is increased or the concentration of the raw material liquid is increased, the rapid generation of reaction heat is precisely detected. Therefore, it is an object of the present invention to provide a method and an apparatus for producing a chemical reactant that can not only improve the yield of the target reactant but also realize industrialization.

  In order to achieve the above-mentioned object, the method for producing a chemical reactant of the present invention is based on the influence of reaction heat when an exothermic reaction is performed by joining a plurality of raw material liquids from the respective supply channels to the junction of the reaction channel. In the method for producing a chemical reactant that suppresses the generation of by-products other than the reactants, at least one of the plurality of raw material liquids is divided and the raw material liquids are separated from each other at the junction of the reaction channel. Forming a multi-layer flow in which the raw material liquids are arranged in a thin layer state by forming a multi-layer flow, and a central fluid flowing through at least the central portion of the multi-layer flow into the reaction flow path And an internal cooling step for cooling the reaction heat from the inside of the reaction flow path by cooling in advance before joining.

  In the present invention, since the raw material liquid dividing step and the reaction heat internal cooling step are combined, the cooling of the reaction heat can be controlled effectively and precisely.

  That is, in the dividing step of the raw material liquid, the rapid generation of reaction heat can be alleviated by forming a multi-layer flow in which the raw material liquids are alternately arranged at the merging portion of the reaction channel and reacting in a thin film state. it can.

  Then, in the internal cooling step, the reaction fluid is cooled from the inside of the reaction channel by cooling in advance before the central fluid flowing in at least the central part of the multilayer flow is joined to the reaction channel.

In this way, by dividing the raw material liquid to mitigate the rapid heat generation of the reaction heat and cooling the reaction heat from the inside of the reaction channel, the rapid heat generation of the reaction heat can be precisely controlled. It is possible to suppress the generation of by-products other than the target reactant due to the influence of the above. In particular, by providing the dividing step, the radial cross-sectional area for each fluid in each fluid constituting the multi-layer flow is reduced. Therefore, even if the reaction channel diameter is increased in order to perform a high flow rate process. When viewed for each divided fluid, it is the same as the reaction in the microreactor. Specifically, it is preferable that the radial cross-sectional area of each fluid constituting the multilayer flow is 1 mm ² or less.

  Therefore, in the method for producing a chemical reactant according to the present invention, even if the diameter of the reaction channel is increased or the concentration of the raw material liquid is increased in order to perform a high flow rate treatment, it is possible to effectively generate a sudden increase in reaction heat. Since it can suppress, the production | generation of a side reaction part can be suppressed. Thereby, not only the yield of the target reactant can be improved, but also industrialization can be realized.

  In the present invention, it is preferable to further include an external cooling step of cooling the reaction channel from the outside of the reaction channel and cooling the reaction heat from the outside of the reaction channel.

  By cooling from both the inside and outside of the reaction channel, the reaction heat distribution in the radial cross section of the reaction channel is reduced, so that the reaction field is stabilized and the generation of side reactants can be further suppressed.

  And in the said internal cooling process, it is preferable to make cooling degree small about the fluid which comprises the said multilayer flow, the fluid which leaves | separates from the center part of the said reaction flow path.

  Thus, in the external cooling step, cooling is performed from both wall surfaces of the reaction channel toward the central portion, so that the internal cooling step is cooled in a direction opposite to the external cooling step (from the central portion toward both side wall surfaces). For example, the liquid temperature in the channel width direction of the multilayer flow can be made uniform.

  In the present invention, it is preferable to further include a flow velocity equalizing step for equalizing the flow velocity when each fluid constituting the multilayer flow merges with the reaction flow path.

  Thereby, since it becomes difficult to generate a vortex | eddy_current when each fluid which comprises a multilayer flow joins a reaction flow path, the reaction field which performs exothermic reaction can be stabilized. As a result, the generation of by-products can be further suppressed.

  In addition, in order to equalize the flow rate in the flow rate equalization step, it can be achieved by adjusting the number of divisions of the plurality of raw material liquids in the division step or adjusting the concentration of the plurality of raw material solutions. Moreover, since it can also be achieved by making the radial cross-sectional areas of the respective supply paths communicating with the reaction flow path different, a preferable method may be selected as appropriate.

  Further, it is preferable that the respective supply paths are formed symmetrically about the reaction flow path as a center line so that the direction of the velocity vector of the opposing fluid is opposite and equal in magnitude.

As a result, eddy currents are less likely to be generated at the confluence portion of the reaction flow path, and the reaction field for performing the exothermic reaction can be stabilized.
In the present invention, the reaction is preferably any one of a halogen-lithium exchange reaction, a nitration reaction, and a polymerization reaction.

  The present invention is applicable to all chemical reaction products produced by exothermic reaction, but is particularly effective in these reactions.

  In order to achieve the above-mentioned object, the chemical reaction product production apparatus of the present invention has an object that is caused by the influence of reaction heat when an exothermic reaction is performed by joining a plurality of raw material liquids from the respective supply channels to the junction of the reaction channel. In the chemical reaction product manufacturing apparatus that suppresses generation of by-products other than the reactants, at least one of the plurality of raw material liquids is divided, and the raw material liquids are separated from each other at the junction of the reaction channel. The raw material liquid dividing means for reacting the raw material liquids in a thin layer state by forming a multi-layer flow in which the multi-layer flows are alternately arranged, and the central fluid flowing at least in the central portion of the multi-layer flow is used as the reaction channel. An internal cooling means for cooling the reaction heat from the inside of the reaction flow path by cooling in advance before joining.

  In the present invention, it is preferable to further include an external cooling means for cooling the reaction channel from the outside of the reaction channel and cooling the reaction heat from the outside of the reaction channel.

  This constitutes the present invention as an apparatus invention.

  According to the method and apparatus for producing a chemical reactant of the present invention, even if the diameter of the reaction channel is increased or the concentration of the raw material liquid is increased in order to perform a high flow rate treatment, the reaction heat is rapidly generated. Since it can be precisely controlled, not only can the yield of the target reactant be improved, but also industrialization can be realized.

The perspective view which is an example of the manufacturing apparatus of the chemical reaction material of this invention, and used the 6-way reactor as a reactor Conceptual diagram of the manufacturing equipment in plan view Explanatory drawing explaining the constriction flow in the confluence part of the reaction channel Explanatory drawing that equalizes the flow rate of the five fluids that join the junction of the reaction channel Explanatory drawing that equalizes the flow rate of five fluids by changing the radial cross-sectional area of the supply path Conceptual diagram of a three-way reactor as another embodiment of the reactor Explanatory drawing explaining the case where a T-shaped reactor is used as a reactor in an Example

  Hereinafter, preferred embodiments of a method for producing a chemical reaction product and a production apparatus of the present invention will be described in detail with reference to the accompanying drawings.

  FIG. 1 is a perspective view of a case where a six-way reactor is used as a reactor as an example of the chemical reaction product production apparatus 10 of the present invention. FIG. 2 is a conceptual view of the manufacturing apparatus 10 as viewed in plan. In FIG. 1, the dividing means and the diluting means, which will be described later, are omitted.

  In the present embodiment, an example will be described in which two kinds of raw material liquids L1 and L2 (see FIG. 2) are used, the raw material liquid L1 is divided into three fluids, and the raw material liquid L2 is divided into two fluids.

  As shown in FIG. 1, the manufacturing apparatus 10 mainly includes first and second dividing means 12 (12A, 12B) (see FIG. 2) for dividing two kinds of raw material liquids L1, L2 that perform an exothermic reaction, The six-way reactor 14 for reacting the divided raw material liquids L1 and L2, and the respective liquid feeding means 16 (16A, 16B, 16C, 16D, and 16E) for feeding the divided raw material liquids L1 and L2 to the six-way reactor 14 ), A plurality of liquid feeding pipes 18 (18A, 18B, 18C, 18D, 18E) for connecting the liquid feeding means 16 and the six-way reactor 14, and raw material liquids L1, L2 provided in each liquid feeding pipe 18 The internal cooling means 20 (20A, 20B, 20C, 20D, 20E) for cooling the reaction heat from the inside of the 6-way reactor 14 by cooling itself and the 6-way reactor 14 from above and below, External cooling means 21 for cooling the heat of reaction from the outside of the coater 14 and (21A, 21B), in constructed.

  The dividing means 12 may be any device as long as it can divide the liquid with high accuracy.

  The six-way reactor 14 is formed by combining a substrate 14A and a cover plate 14B, and a plurality of (five in the present embodiment) supply grooves and one reaction groove are engraved on the mating surface of the substrate 14A. Is done. Then, the supply plate 22 (22A, 22B, 22C, 22D, 22E) and one reaction flow channel 24 are formed by integrating the cover plate 14B with the substrate 14A. In FIG. 2, a supply path disposed opposite to the reaction flow path 24 is a first supply path 22A, and hereinafter, a second supply path 22B, a third supply path 22C, a fourth supply path 22D, and a fifth supply are clockwise. Let's say it is Road 22E.

Further, through holes for connecting the liquid feeding pipes 18 to the supply paths 22 are formed in the cover plate 14B and the upper external cooling means 21A, and are connected to the distal ends of the supply paths 22, respectively. The channel cross-sectional area of the reaction channel 24 is preferably set by the number of divisions divided by the dividing means 12 (12A, 12B). That is, the channel cross-sectional area of the reaction channel 24 is set so that the radial cross-sectional area of one fluid in each divided fluid is 1 mm ² or less. For example, when the raw material liquids L1 and L2 are divided into five fluids in total, the maximum cross-sectional area of the reaction flow path 24 is set to 5 mm ² . Therefore, the larger the number of divisions, the thicker the reaction channel 24 can be made.

  The six-way reactor 14 can be manufactured using precision processing techniques such as micro drilling, micro electric discharge machining, molding using plating, injection molding, dry etching, wet etching, and hot embossing. Moreover, since the channel diameter of the reaction channel 24 is 1.0 mm or more in equivalent diameter as described above, the reaction channel 24 can be enlarged as compared with a reaction channel (microchannel) in a general microreactor. Machining techniques using can also be used.

  The material of the six-way reactor 14 is not particularly limited as long as the above processing technique can be applied. Specifically, metal materials (iron, aluminum, stainless steel, titanium, various metals, etc.), resin materials (acrylic resin, PDMS, etc.), glass (silicon, Pyrex (registered trademark), quartz glass, etc.), quartz Glass or Pyrex (registered trademark) glass subjected to parylene (paraxylene vapor deposition) treatment, or fluorine or hydrocarbon silane coupling treatment can be suitably used.

  Further, as will be described later, the six-way reactor 14 is made of a transparent material so that the contracted state in which the five fluids obtained by dividing the two types of raw material liquids L1 and L2 contract at the joining portion can be visually observed. It is preferable.

  The liquid feeding means 16 may be any one that can accurately deliver a small volume of liquid. For example, a microsyringe pump can be preferably used.

  The cooling temperature control itself of the internal cooling means 20 and the external cooling means 21 can be performed by a conventional temperature control technique or a new temperature control technique represented by a Peltier element, and selection of an appropriate cooling mechanism and temperature sensing mechanism. In addition, the optimum method can be selected by combining the configurations of the external control systems.

  Further, the six-way reactor 14 is provided with a discharge pipe 26 (see FIG. 1) for the reaction liquid LM discharged from the end of the reaction channel 24 to the outside, and is formed in the cover plate 14B and the upper external cooling means 21A. The reaction channel 24 is connected to the terminal portion through the through-hole.

  Next, the manufacturing method of the present invention will be described using the chemical reaction product manufacturing apparatus 10 configured as described above.

  As shown in FIG. 2, of the two types of raw material liquids L1 and L2 that perform an exothermic reaction, the raw material liquid L1 is divided into three fluids L1a, L1b, and L1c by the first dividing means 12A. On the other hand, the raw material liquid L2 is divided into two fluids L2a and L2b by the second dividing means 12B.

  The divided three fluids L1a to L1c are fed to the first supply path 22A, the third supply path 22C, and the fourth supply path 22D, while the divided two fluids L2a and L2b are supplied to the second supply path 22B. The solution is fed to the fifth supply path 22E. As a result, in the merging portion 24A of the reaction flow path 24, a composite material composed of a sandwich-like five-layer flow in which the raw material liquid 2 is sandwiched between the raw material liquids 1 flowing between the central portion and both wall surfaces of the reaction flow path 24 is obtained. A laminar flow L (see FIG. 3) is formed. While the multi-layer flow L flows through the reaction flow path 24, the raw material liquids react to generate heat.

In such an exothermic reaction, internal cooling means 20A to 20E are provided in the middle of each of the flow paths 22A to 22E, and before the central fluid L1a flowing through the central portion of the reaction flow path 24 is joined to the reaction flow path 24 in advance. To be cooled. Further, the entire six-way reactor 14 is cooled by the external cooling means 21. Thereby, the delay in cooling due to heat exchange from the outside of the reaction channel 24 can be compensated by directly cooling the fluid from the inside of the reaction channel 24, so that the reaction heat can be effectively cooled. . In addition, since there is no cooling delay in the radial cross section of the reaction channel 24, the reaction heat can be easily controlled. In particular, by providing the dividing step, the radial cross-sectional area for each fluid in each of the fluids constituting the multi-layer flow L becomes small. Even if the flow path diameter is increased by increasing the size, the reaction is similar to that in the microreactor when viewed for each divided fluid. Specifically, as described above, it is preferable that the radial cross-sectional area of each fluid constituting the multilayer flow is 1 mm ² or less. Thereby, since rapid heat generation of the reaction heat can be controlled, it is possible to suppress generation of a side reaction product other than the target reaction product due to the influence of the reaction heat.

  In the internal cooling described above, only the fluid L1a flowing through the central portion of the reaction channel 24 is cooled, but it is preferable to cool all the five fluids L1a to L2b constituting the multilayer flow L. In this case, with respect to each of the fluids L1a to L2b constituting the multi-layer flow L, it is preferable to reduce the cooling degree as the fluid moves away from the central portion of the reaction channel 24. Thereby, the liquid temperature of the radial cross section of the multilayer flow L can be made uniform in combination with the external cooling in which the six-way reactor 14 is cooled by the external cooling means 21. In this way, by controlling the cooling temperature in advance for each location where the reaction flow paths 24 of the five fluids L1a to L2b constituting the multi-layer flow L are present, the reactivity is good and the processing in one six-way reactor 14 is performed. The amount can be increased dramatically, and the cost can be greatly reduced compared to the numbering up cost. In this case, for each of the fluid far from both wall surfaces of the reaction flow path 24 (fluid flowing in the center portion) and the fluid close to each other, the amount of heat generated by the reaction and the amount of cooling by the cooling are obtained in advance by preliminary tests, simulations, and the like. Accordingly, it is preferable to cool each of the fluids L1a to L2b so that the liquid temperature in the radial cross section of the multilayer flow L is made uniform.

  The radial cross-sectional area of the reaction channel 24 is preferably formed to be smaller than the total value of the radial cross-sectional areas of the five supply channels 22A to 22E. As a result, as shown in FIG. 3, the multi-layer flow L formed by merging with the merging portion 24 </ b> A of the reaction flow path 24 is contracted and thinned. Therefore, since the raw material liquids L1 and L2 can be caused to react exothermically in a thin layer state in the reaction flow path 24, rapid heat generation of the reaction heat can be reduced.

  In this case, as shown in FIG. 4, it is preferable to make the flow rates V1 and V2 of the five fluids L1a to L2b joining the joining portion 24A of the reaction channel 24 uniform. Accordingly, since the vortex is less likely to occur when the five fluids L1a to L2b join the joining portion 24A of the reaction channel 24, the reaction field is stabilized. Therefore, generation of side reaction products can be further suppressed. If a vortex is generated when joining the reaction channel 24, the exothermic reaction in the reaction channel 24 becomes unstable, so that the reaction field becomes unstable and the reaction heat becomes difficult to control precisely. As a result, the generated target product reacts with the unreacted raw material liquid due to the influence of reaction heat, and a side reaction product is easily generated. Further, since the multi-layer flow is destroyed by the vortex, the control accuracy when cooling the reaction heat from the inside is deteriorated.

  As a method for equalizing the flow rates of the five fluids L1a to L2b that join the reaction flow path 24, a method is preferably used in which the flow rates of the five fluids L1a to L2b are made the same by adjusting the number of divisions of the raw material liquids L1 and L2. Can be adopted. However, since the flow rates of the five fluids L1a to L2b may not be equalized only by adjusting the division of the raw material liquids L1 and L2, dilution for diluting the raw material liquids L1 and L2 before the dividing means 12A and 12B in FIG. It is preferable to provide means 28A, 28B. Thereby, the supply amount of the raw material liquid 1 and the raw material liquid 2 flowing into the reaction flow path 24 can be changed by adjusting the concentration of the raw material liquids L1 and L2, respectively. Becomes easier.

  Further, in order not to generate a vortex in the merging portion 24A of the reaction channel 24, as shown in FIG. 2, the reaction channel 24 is a center line 30 (two-dot chain line), and the supply channels 22A to 22E are left and right. It is preferable to form them symmetrically so that the direction of the velocity vector of the opposing fluid is opposite and equal in magnitude. For example, in FIG. 2, the second supply path 22B and the fourth supply path 22D are arranged to face each other, so that the directions of the velocity vectors of the fluid L2a and the fluid L1c facing each other are opposite and equal in size. Further, the third supply path 22C and the fifth supply path 22E are arranged to face each other, so that the directions of the velocity vectors of the fluid L1b and the fluid L2b facing each other are opposite and equal in size. Thereby, since the kinetic energy of the fluid which opposes can be mutually canceled, generation | occurrence | production of the vortex | eddy_current in the junction part 24A can be suppressed reliably.

  Further, as shown in FIG. 5, the flow rates of the fluids L <b> 1 a to L <b> 2 b that join the reaction flow path 24 can be made the same by making the radial cross-sectional areas of the respective supply paths 22 different. In FIG. 5, the radial cross-sectional areas of the first, third, and fourth supply paths 22A, 22C, and 22D to which the raw material liquid L1 is supplied are shown as second and fifth supply paths 22B to which the raw material liquid L2 is supplied. , 22E is made smaller than the radial cross-sectional area so that the flow rates of the five fluids L1a to L2b are the same.

  In this embodiment, the example of the two types of raw material liquids L1 and L2 has been described. However, the number of raw material liquids is not limited as long as the reaction system performs an exothermic reaction. Moreover, although the example of the six-way reactor 14 has been described as a reactor, the production method of the present invention can be applied to a reactor having two or more supply paths.

  FIG. 6 is an example of a three-way reactor 32 that also incorporates a dividing means, and shows a case where the raw material liquid L1 is divided into two. As shown in FIG. 6, the three-way reactor 32 divides the reaction channel 34 and the raw material liquid L1 into two branch channels 36 </ b> A and 36 </ b> B and joins them to the junction 34 </ b> A of the reaction channel 34. The flow path 36 and the second flow path 38 that joins the raw material liquid L2 to the merge section 34A are configured. In the case of the three-way reactor 32, as described with reference to FIGS. 1 and 2, the internal cooling means 20 for internally cooling at least one of the raw material liquids L1 and L2, and the external for cooling the three-way reactor from the outside. Cooling means 21 is provided.

[Example]
Next, more specific examples of the method for producing a chemical reaction product of the present invention will be described.

  A test for synthesizing (3-methoxyphenyl) trimethylsilane was performed under the conditions of Test 1 to Test 4 shown below.

(Test 1)
Test 1 uses a T-shaped mixer 40 shown in FIG. 7A as a reactor, cools the reaction heat by cooling only from the outside of the T-shaped mixer 40, and the flow rates of the raw material liquids L1 and L2 are different. Is the case.

In Test 1, a T-shaped mixer 40 (made of SUS316, flow path inner diameter 0.8 mm, flow path cross-sectional area 0.5 mm ² ) shown in FIG. Then, the n-butyllithium solution (raw material liquid L2) was fed from the respective supply passages 42 and 44 to the confluence 46A of the reaction passage 46 and collided with each other, thereby performing a halogen-lithium exchange reaction.

  The raw material liquid L1 was adjusted to a concentration of 0.26 mol / L by diluting 2.46 g of 3-bromoanisole with tetrahydrofuran so that the total amount became 50 mL.

  As the raw material liquid L2, a commercially available reagent dissolved in an n-hexane solution at 1.58 mol / L was purchased, and the content of n-butyllithium was determined by titration and used.

  Separately from the raw material liquids L1 and L2, a 100 mL two-necked flask was prepared by adding 1.5 g of chlorotrimethylsilane and 9 mL of tetrahydrofuran and stirring them.

  Then, after the raw material liquid L1 and the raw material liquid L2 are sucked into the glass syringe, the PHD2000 type metering pump made by HARVARD APPARATUS INC. And the Model100 type metering pump made by Kd Scientific are used in the reaction channel 46, respectively. The solution was fed to the junction 46A. The liquid feeding flow rates of the raw material liquid L1 and the raw material liquid 2 were 5.0 mL / min and 1.0 mL / min, respectively. That is, since the flow passage cross-sectional areas of the supply passages 42 and 44 are the same, the flow rates of the raw material liquid L1 and the raw material liquid L2 are in a relationship of 5: 1.

  The reaction solution LM reacted in the reaction channel 46 of the T-shaped mixer 40 is discarded to the drain side for the first minute, and then the three-way valve (not shown) is switched to the above-mentioned 100 ml two-necked flask side. For 7 minutes. Thereby, (3-methoxyphenyl) trimethylsilane was synthesized. In this reaction, the T-shaped mixer 40 and piping (not shown) therefrom were cooled to 25 ° C. from the outside, and the liquid temperature flowing out of the T-shaped mixer 40 was measured. As a result, the liquid temperature was 25 ° C. there were.

  The obtained (3-methoxyphenyl) trimethylsilane solution was quantitatively analyzed. As a result, the yield was 78%.

  FIG. 7B is a result of simulating the state in the merging portion 46A of the reaction channel 46 using FUNENT 6.3 manufactured by ANSYS, and the flow rates of the raw material liquids L1 and L2 are different. A vortex 48 (white portion) is generated in the part.

(Test 2)
Test 2 is a case where cooling is performed only from the outside of the reactor and the flow rates of the raw material liquids L1 and L2 are different as in Test 1, but the raw material liquids L1 and L2 are divided by using a six-way reactor as the reactor. And reacted in a thin layer state.

As a reactor for performing a halogen-lithium exchange reaction, the six-way reactor 14 of FIG. 1 having five supply channels and one reaction channel (manufactured by SUS316, channel inner diameter 1.5 mm, channel cross-sectional area 1.77 mm ² ). However, the internal cooling means 20 was not used.

  Then, 25.0 mL / min, which is the total flow rate of the raw material liquid L1, was divided into three to form three fluids flowing through the center and both sides of the radial cross section of the reaction channel 24 (8.3 mL / min per fluid). ). On the other hand, the total flow rate of the raw material liquid L2 of 5.0 mL / min was divided into two and decomposed into two fluids (2.5 mL / min per fluid). And the raw material liquid L1 and the raw material liquid L2 were arranged alternately. That is, since the flow path cross-sectional areas of the respective supply paths 22A to 22E are the same, the flow rates of the raw material liquid L1 and the raw material liquid L2 are in a relationship of 8.3: 2.5.

  The reaction liquid LM from the reaction flow path 24 of the 6-way reactor 14 is discarded to the drain side for the first minute as in Test 1, and then the three-way valve (not shown) is switched, and the 100 ml of the above-mentioned 100 ml It was allowed to pass through the mouth flask side for 7 minutes. In this reaction, the 6-way reactor 14 and the piping (not shown) therefrom were cooled to 25 ° C. from the outside, and the liquid temperature flowing out from the 6-way reactor was measured. As a result, the liquid temperature was 25 ° C.

  The obtained (3-methoxyphenyl) trimethylsilane solution was quantitatively analyzed. As a result, the yield was 88%.

(Test 3)
Test 3 is a further improvement of Test 2, in which the internal fluid 20 is used to cool the central fluid that joins the center of the reaction channel 24 in advance and from both inside and outside the reaction channel 24. This is when the heat of reaction is cooled.

  The same 6-way reactor 14 as in Test 2 was used as a reactor for performing the halogen-lithium exchange reaction.

  Then, 25.0 mL / min, which is the total flow rate of the raw material liquid L1, was divided into three to form three fluids flowing through the center and both sides of the radial cross section of the reaction channel. The central fluid that joins the center of the reaction channel among the three divided fluids is cooled in advance by the internal cooling means 20 before being sent to the six-way reactor 14, and the liquid temperature at the inlet of the six-way reactor 14 is 0 ° C. I tried to become.

  On the other hand, 5.0 mL / min, which is the total flow rate of the raw material liquid L2, was divided into two parts and decomposed into two fluids so that the raw material liquid L1 and the raw material liquid L2 were alternately arranged. The divided two fluids were cooled in advance by the internal cooling means 20 before being sent to the six-way reactor 14 so that the liquid temperature at the inlet of the six-way reactor 14 was 15 ° C.

  The reaction liquid LM from the reaction flow path 24 of the 6-way reactor 14 is discarded to the drain side for the first minute as in Test 1, and then the three-way valve (not shown) is switched, and the 100 ml of the above-mentioned 100 ml It was allowed to pass through the mouth flask side for 7 minutes. In this reaction, the 6-way reactor 14 and the piping (not shown) therefrom were cooled to 25 ° C. from the outside, and the liquid temperature flowing out from the 6-way reactor 14 was measured. As a result, the liquid temperature was 25 ° C. .

  The obtained (3-methoxyphenyl) trimethylsilane solution was quantitatively analyzed. As a result, the yield was 96%.

(Test 4)
Test 4 is a further improvement of Test 3, and by changing the radial cross-sectional area of the supply path, the flow rates at which the fluids obtained by dividing the raw material liquid L1 and the raw material liquid L2 merge into the reaction flow path are all the same. I was going to be. Therefore, the first, third, and fourth supply paths 22A, 22C, and 33D to which the raw material liquid L1 is supplied have an inner diameter of 1.5 mm and a flow path cross-sectional area of 1.77 mm ² , and the raw material liquid L2 is supplied. The second and fifth supply paths 22B and 22E have an inner diameter of 0.83 mm and a channel cross-sectional area of 0.54 mm ² so that the flow velocity supplied from all the channels to the merging portion 24A is uniform.

  The reaction liquid LM from the reaction flow path 24 of the 6-way reactor 14 is discarded to the drain side for the first minute as in Test 1, and then the three-way valve (not shown) is switched, and the 100 ml of the above-mentioned 100 ml It was allowed to pass through the mouth flask side for 7 minutes. In this reaction, the 6-way reactor 14 and the piping (not shown) therefrom were cooled to 25 ° C. from the outside, and the liquid temperature flowing out from the 6-way reactor was measured. As a result, the liquid temperature was 25 ° C.

  The obtained (3-methoxyphenyl) trimethylsilane solution was quantitatively analyzed. As a result, the yield was 98%.

[Consideration of test results]
The yield of test 1 was 78% and the yield of test 2 was 86%.

  On the other hand, as can be seen from the result of Test 3 in which the production method of the present invention was performed, the raw material liquids L1 and L2 were divided and reacted in a thin layer state in the reaction channel 24, and the reaction channel 24 was externally By cooling from both the inside and the inside, it was possible to suppress the formation of by-products in the halogen-lithium exchange reaction, and as a result, the yield of (3-methoxyphenyl) trimethylsilane could be increased to 96%.

  Furthermore, as can be seen from the result of the more preferable test 4 of the production method of the present invention, by further equalizing the flow rate of each fluid that joins the joining part of the reaction flow channel to the condition of test 3, (3-methoxy The yield of phenyl) trimethylsilane could be increased to 98%.

  In this embodiment, the example of the halogen-lithium exchange reaction has been described. However, the present invention can also be provided for exothermic reactions such as nitration reaction and polymerization reaction.

  DESCRIPTION OF SYMBOLS 10 ... Chemical reaction material manufacturing apparatus, 12 ... Dividing means, 14 ... 6-way reactor, 18 ... Liquid feeding pipe, 20 ... Internal cooling means, 21 ... External cooling means, 22 ... Supply path, 24 ... Reaction flow path, 24A ... Merging portion of reaction channel, 26 ... Drain pipe, 28 ... Dilution means, 30 ... Center line, 32 ... 3-way reactor, 34 ... Reaction channel, 36 ... First channel, 38 ... Second channel , 40 ... T-shaped reactor, 42, 44 ... supply path, 46 ... reaction flow path

Claims (13)

A chemical reactant that suppresses the generation of side reactants other than the target reactant due to the influence of reaction heat when an exothermic reaction is caused by joining a plurality of raw material liquids from the respective supply channels to the junction of the reaction channel. In the manufacturing method of
By dividing at least one raw material liquid of the plurality of raw material liquids and forming a multi-layer flow in which the raw material liquids are alternately arranged at the junction of the reaction flow path, the raw material liquids are reacted in a thin layer state. Dividing the raw material liquid;
An internal cooling step of cooling the reaction heat from the inside of the reaction flow path by pre-cooling the central fluid flowing through at least the central portion of the multilayer flow before joining the reaction flow path. A method for producing a chemical reaction product.   2. The chemical reaction product according to claim 1, further comprising an external cooling step of cooling the reaction flow channel from the outside of the reaction flow channel to cool the reaction heat from the outside of the reaction flow channel. Production method.   3. The chemical reaction product according to claim 1, wherein in the internal cooling step, the degree of cooling of each fluid constituting the multilayer flow is reduced as the fluid moves away from the central portion of the reaction flow path. Production method.   The chemistry according to any one of claims 1 to 3, further comprising a flow velocity equalizing step for equalizing a flow velocity when each fluid constituting the multilayer flow joins the reaction channel. A method for producing a reactant.   5. The flow rate homogenizing step equalizes the flow rate of each fluid that joins the reaction flow path by adjusting the number of divisions of the plurality of raw material liquids in the dividing step. A method for producing a chemical reactant.   In the flow velocity equalization step, the flow rates of the fluids that join the reaction flow path are made uniform by adjusting the concentrations of the plurality of raw material liquids and changing the supply amounts of the plurality of raw material liquids that join the reaction flow path. The method for producing a chemical reaction product according to claim 4, wherein:   5. The chemistry according to claim 4, wherein in the flow rate uniformization step, the flow rate of each fluid that joins the reaction flow path is made uniform by adjusting the number and concentration of the plurality of raw material liquids. A method for producing a reactant.   5. The chemical flow according to claim 4, wherein, in the flow velocity uniformizing step, the flow velocity of each fluid that merges with the reaction flow path is made uniform by making the radial cross-sectional areas of the respective supply paths different. A method for producing a reactant.   2. The respective flow paths are formed symmetrically about the reaction flow path as a center line so that the direction of the velocity vector of the opposing fluid is opposite and equal in size. The manufacturing method of the chemical reactant of any one of -8. 10. The method for producing a chemical reactant according to claim 1, wherein a radial cross-sectional area of each fluid constituting the multilayer flow is 1 mm ² or less.   The method for producing a chemical reaction product according to any one of claims 1 to 9, wherein the reaction is any one of a halogen-lithium exchange reaction, a nitration reaction, and a polymerization reaction. A chemical reactant that suppresses the generation of side reactants other than the target reactant due to the influence of reaction heat when an exothermic reaction is caused by joining a plurality of raw material liquids from the respective supply channels to the junction of the reaction channel. In the manufacturing equipment of
By dividing at least one raw material liquid of the plurality of raw material liquids and forming a multi-layer flow in which the raw material liquids are alternately arranged at the junction of the reaction flow path, the raw material liquids are reacted in a thin layer state. Means for dividing the raw material liquid;
An internal cooling means for cooling the reaction heat from the inside of the reaction channel by precooling the central fluid flowing through at least the central part of the multilayer flow before joining the reaction channel. An apparatus for producing a chemical reaction product.   The chemical reaction product according to claim 12, further comprising an external cooling means for cooling the reaction channel from outside the reaction channel and cooling the reaction heat from outside the reaction channel. Manufacturing equipment.

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