JP4842770B2 - Method for producing immobilized enzyme reaction tower - Google Patents

Description

  The present invention relates to a method for producing an immobilized enzyme reaction tower.

  Conventionally, in the production of chemical substances in a chemical plant or the like, a catalyst is used when performing various reactions. For example, a method of performing a reaction by filling a catalyst formed in a granular form into a cylindrical reaction tower and passing the raw material oil, reaction liquid, gas or a mixture thereof through the reaction tower and bringing them into contact with the catalyst surface Has been done. Moreover, in the hydrolysis of fats and oils, as a representative method, a method is used in which an immobilized enzyme in which an enzyme is adsorbed on a water-insoluble carrier is packed in a fixed bed type reaction tower, and the fats and oils are allowed to flow therethrough. It has been known.

When the reaction is performed using an immobilized enzyme reaction tower, in order to suppress non-uniform flow of the reaction liquid in the tower and increase in pressure loss, the solid catalyst or the immobilized enzyme in the fixed bed reaction tower It is desired to be filled in a uniform state. As a method of filling the solid catalyst or immobilized enzyme used in the reaction into the fixed bed type reaction tower, a method in which an operator manually performs work inside or outside the reaction tower or a catalyst filling device such as a belt conveyor is used. The method is common. In addition, for the purpose of preventing destruction of the catalyst at the time of filling, the catalyst is mixed with a liquid and filled in a slurry state (see Patent Document 1), or the reaction tube is filled with a liquid material and subsequently filled with a solid catalyst. After that, a method for removing the liquid material (see Patent Document 2) is disclosed.
JP-A-61-35843 Japanese Patent Laid-Open No. 9-141084

  On the other hand, when packing a solid catalyst or an immobilized enzyme in a wet state, the handling property is remarkably inferior, so that uniform packing becomes very difficult in a usual method. Moreover, the method of the patent document mentioned above has a problem that it is difficult to obtain a sufficiently high bulk density of the packed bed and the packing efficiency is lowered. Furthermore, when liquid or gas is passed in a packed state with a low bulk density, there is a problem that a part of the packed bed collapses, resulting in non-uniform flow in the packed bed and reduced reaction efficiency. Improvement is desired.

  Accordingly, an object of the present invention is to provide an efficient production method having a high bulk density in a production method of an immobilized enzyme reaction column in which an immobilized enzyme is packed into a fixed bed type reaction column. Another object of the present invention is to provide an efficient method for producing fatty acids with a high expression of enzyme activity by a packed reaction tower.

  Therefore, as a result of analyzing the behavior at the time of filling the immobilized enzyme, the present inventor, by supplying a mixed slurry of the immobilized enzyme and oil under a predetermined pressure, into the reaction tower filled with oil, It has been found that an immobilized enzyme reaction tower in which the enzyme is uniformly packed with a high bulk density is obtained, and thereby high enzyme activity is obtained.

  That is, the present invention relates to a method for producing an immobilized enzyme reaction tower in which an immobilized enzyme is packed in a fixed bed type reaction tower, wherein after filling the reaction tower with an oil phase substrate, the unit packing height of the enzyme is increased. The present invention provides a method for producing an immobilized enzyme reaction tower in which a mixed slurry of an immobilized enzyme and an oil phase substrate is supplied to the reaction tower so that the pressure loss per unit is 0.04 to 1 MPa / m.

  The present invention also provides a method for producing fatty acids by hydrolyzing fats and oils by supplying an oil phase substrate and an aqueous phase substrate to an immobilized enzyme reaction tower produced by the method.

  According to the present invention, the immobilized enzyme can be uniformly packed in the fixed bed type reaction tower, and a packed bed having a high bulk density can be obtained. Can be efficiently manufactured.

  As an aspect of the present invention, the immobilized enzyme is packed into a fixed bed type reaction tower by supplying an oil-degrading enzyme adsorbed on an immobilized carrier as the immobilized enzyme and supplying it as a mixed slurry with an oil phase substrate. It is a method for producing an immobilized enzyme reaction tower, and is a method for producing fatty acids by hydrolyzing fats and oils by passing an oil phase substrate and an aqueous phase substrate through the reaction tower thus obtained. preferable.

  The immobilized enzyme used in the present invention is one in which an enzyme is supported on an immobilized carrier by adsorption or the like. As the immobilization carrier, Celite, diatomaceous earth, kaolinite, silica gel, molecular sieves, porous glass, activated carbon, calcium carbonate, ceramics and other inorganic carriers, ceramic powder, polyvinyl alcohol, polypropylene, chitosan, ion exchange resin, hydrophobic adsorption Examples thereof include organic polymers such as resins, chelate resins, and synthetic adsorption resins, and ion exchange resins are particularly preferable from the viewpoint of high water retention. Of the ion exchange resins, a porous material is preferable because it has a large surface area and can increase the amount of adsorbed enzyme.

  The particle diameter of the resin used as the immobilization carrier is preferably 100 to 1000 μm, more preferably 250 to 750 μm. The pore diameter is preferably 10 to 150 nm, more preferably 10 to 100 nm. Examples of the material include phenol formaldehyde, polystyrene, acrylamide, divinylbenzene, and the like, and phenol formaldehyde resin (for example, Duolite A-568 manufactured by Diamond Shamrock) is particularly preferable from the viewpoint of improving the enzyme adsorptivity.

  The enzyme used for the immobilized enzyme of the present invention is not particularly limited, but lipase is preferred as an enzyme for decomposing oils and fats from the viewpoint of a large productivity improvement effect. As the lipase, not only those derived from animals and plants but also commercially available lipases derived from microorganisms can be used. Examples of microorganism-derived lipases include the genus Rizopus, Aspergillus, Mucor, Pseudomonas, Geotrichum, Penicillium, and Candida. The thing of origin is mentioned.

  The temperature at which the enzyme is immobilized can be determined depending on the properties of the enzyme, but is preferably 0 to 60 ° C., particularly 5 to 40 ° C. at which the enzyme is not deactivated. Moreover, the pH of the enzyme solution used at the time of immobilization may be in a range where no denaturation of the enzyme occurs, and can be determined by the characteristics of the enzyme as well as the temperature, but is preferably pH 3-9. In order to maintain this pH, a buffer solution is used. Examples of the buffer solution include an acetate buffer solution, a phosphate buffer solution, and a Tris-HCl buffer solution. The enzyme concentration in the enzyme solution is preferably not more than the saturation solubility of the enzyme and sufficient from the viewpoint of immobilization efficiency. Moreover, the enzyme solution can also use what was refine | purified by the supernatant obtained by removing the insoluble part by centrifugation, ultrafiltration, etc. as needed. Moreover, although the enzyme mass to be used varies depending on the enzyme activity, it is preferably 5 to 1000 mass%, particularly preferably 10 to 500 mass%, based on the mass of the carrier.

  When the enzyme is immobilized, the carrier and the enzyme may be directly adsorbed. However, in order to obtain an adsorption state that expresses high activity, the carrier may be treated with a fat-soluble fatty acid or a derivative thereof in advance before the enzyme adsorption. preferable. As a method for contacting the fat-soluble fatty acid or derivative thereof with the carrier, these may be added directly to water or an organic solvent, but in order to improve dispersibility, the fat-soluble fatty acid or derivative thereof is once dispersed and dissolved in the organic solvent. And then added to a carrier dispersed in water. Examples of the organic solvent include chloroform, hexane, ethanol, and the like. The used mass of the fat-soluble fatty acid or derivative thereof is preferably 1 to 500 mass%, particularly preferably 10 to 200 mass%, based on the mass of the carrier. The contact temperature is preferably 0 to 100 ° C, particularly preferably 20 to 60 ° C, and the contact time is preferably about 5 minutes to 5 hours. The carrier after this treatment is collected by filtration, but may be dried. The drying temperature is preferably room temperature to 100 ° C., and drying under reduced pressure may be performed.

  Among the fat-soluble fatty acids or derivatives thereof for treating the carrier in advance, the fat-soluble fatty acid has a saturated or unsaturated, linear or branched, hydroxy group having 4 to 24 carbon atoms, preferably 8 to 18 carbon atoms. Fatty acids that may be used are listed. Specific examples include capric acid, lauric acid, myristic acid, oleic acid, linoleic acid, α-linolenic acid, ricinoleic acid, isostearic acid and the like. Examples of the fat-soluble fatty acid derivatives include esters of these fat-soluble fatty acids with mono- or polyhydric alcohols or saccharides, phospholipids, and those obtained by adding ethylene oxide to these esters. Specific examples include methyl esters, ethyl esters, monoglycerides, diglycerides, ethylene oxide adducts thereof, polyglycerin esters, sorbitan esters, and sucrose esters of the above fatty acids. These fat-soluble fatty acids and derivatives thereof are preferably liquid at room temperature in terms of immobilizing the enzyme on the carrier. As these fat-soluble fatty acids or derivatives thereof, two or more of the above may be used in combination, and naturally derived fatty acids such as rapeseed fatty acids and soybean fatty acids may be used.

  The hydrolysis activity of the immobilized enzyme is preferably 20 U / g or more, more preferably 100 to 10,000 U / g, and particularly preferably 500 to 5000 U / g. Here, 1 U of enzyme produces 1 μmol of free fatty acid per minute when hydrolyzed at 40 ° C. for 30 minutes while stirring and mixing a mixture of fats and oils: water = 100: 25 (mass ratio). The resolution of the enzyme is shown.

  The hydrolysis activity (U / g-oil) of the immobilized enzyme imparted per unit mass of fats and oils and the time required to reach a certain hydrolysis rate are in a substantially inverse relationship. When hydrolysis is carried out using a packed bed (enzyme tower) packed with immobilized enzyme, the hydrolysis rate varies depending on the liquid feeding conditions (flow rate, temperature, etc.), but the time required for hydrolysis (retention time in the packed bed) ) And the weight (g-oil) of the fats and oils present in the packed bed and the packed weight (g) of the immobilized enzyme, the apparent activity (expression activity) (U / g) of the immobilized enzyme is determined.

  The oil phase substrate used in the present invention mainly refers to fats and oils. The fats and oils may contain diacylglycerol, monoacylglycerol, or fatty acids in addition to triacylglycerol, and are obtained as a result of hydrolysis. May contain fatty acids. Specific examples of the oil phase substrate include vegetable oils such as rapeseed oil, soybean oil, sunflower oil, palm oil and linseed oil, animal oils such as beef tallow, pork tallow and fish oil, or a combination of these. These fats and oils can be deodorized oil and non-deodorized fats and oils that have not been deodorized beforehand. However, the use of non-deodorized fats and oils for a part or all of these fats and oils may be trans Saturated fatty acids are preferred, and the plant sterols, plant sterol fatty acid esters, and tocopherols derived from raw oils and fats are preferably left. In the oil phase substrate, oil-soluble components such as fatty acids may be mixed in addition to the oils and fats. Fatty acids refer to fatty acids obtained as a result of hydrolysis, as well as those containing one or more of the above glycerides.

  The aqueous phase substrate used in the present invention is water, but other water-soluble components such as glycerin obtained as a result of hydrolysis may be mixed.

  The fixed bed type reaction column (enzyme column) used in the present invention may have any shape as long as it can withstand the pushing pressure of the pump used. Moreover, it is preferable that a jacket be provided around the enzyme tower so that the reaction liquid flowing in the enzyme tower can be adjusted to a temperature suitable for the enzyme reaction. The temperature in the enzyme tower is preferably 0 to 60 ° C., more preferably 20 to 40 ° C., in order to extract the activity of the immobilized enzyme more effectively. The length of the enzyme column may be a length necessary for obtaining a desired decomposition rate, but it is in the range of 0.01 to 10 m, preferably 0.1 to 5 m from the viewpoint of reactivity, pressure loss in the column, etc. It is preferable that

  In this invention, you may use the thing in which the interior goods or piping in which several tubular structures were formed were loaded as an enzyme tower. Here, the plurality of tubular structures preferably have a circular cross section with a diameter of 100 mm or less or a polygon with a diagonal length of 100 mm or less. When such an enzyme tower is used, the reaction may be performed by filling the tubular structure with an immobilized enzyme and supplying the raw material mixture into the tubular structure. By carrying out the reaction in a plurality of tubular structures having such a small cross-sectional area, the cross-sectional area of the flow path in the enzyme tower is reduced, and the flow of the reaction liquid in two liquid phases is made uniform. Can do. The interior or piping only needs to be able to form a plurality of tubular structures having the cross-sectional area in the enzyme tower, and examples of the interior include columns, prisms, and plates (partition plates). Can be mentioned. That is, the interior or piping is loaded in the vertical direction, preferably in a columnar shape. More specifically, a method of loading a pipe into a multi-tube type, a method of loading a vertical partition plate (a flat plate, a corrugated plate, etc.) inside an enzyme tower, an interior having a circular or polygonal cross section The method of loading etc. is mentioned. Among these, in the case of loading the interior, the shape of the cross section is preferably a regular triangle, a square, or a regular hexagon from the viewpoint of the efficiency of loading the interior. As an interior thing, the thing of the form which bundled the square pipe, for example can be used.

  The diameter or diagonal length of the cross section of one pipe (one flow path) formed of piping or interior is preferably 100 mm or less, but from the viewpoint of improving reactivity, it is further 75 mm or less, and further 50 mm. Hereinafter, it is particularly preferable that the thickness is 35 mm or less.

  The length of the pipe or the interior in the enzyme tower is preferably equal to or greater than the packed thickness of the immobilized enzyme from the viewpoint of uniformizing the flow of the entire reaction liquid in the tower, but the packed thickness is shorter than the packed thickness. The same effect can be obtained if the content is in the range of 50% or more and 75% or more.

  In addition, the pipe or the interior may not be continuous over its entire length, but is divided into a plurality of stages in the vertical direction from the viewpoint of workability such as easy replacement of the packed immobilized enzyme. Is preferred. The number of stages depends on the total length of the enzyme tower, but is preferably 2 to 30 divisions, and more preferably 2 to 10 divisions. Furthermore, the pipes or interiors of each stage may be divided into a plurality of parts in the lateral direction from the viewpoint of ease of loading into the enzyme tower.

  In the present invention, when the immobilized enzyme is charged into the fixed bed type reaction tower, the oil phase substrate is first charged into the tower, and then the mixed slurry of the immobilized enzyme and the oil phase substrate is supplied. The immobilized enzyme concentration in the mixed slurry (content of immobilized carrier and enzyme in the mixed slurry (dry basis)) is 1% by mass to 50% by mass, and further 3% by mass to 30% from the viewpoint of handling properties and productivity. Mass% is preferred.

When packing the mixed slurry, if the enzyme packed bulk density in the reaction tower is low, the reaction efficiency is lowered, and a sufficient enzyme activity expression effect cannot be expected. It is necessary to give On the other hand, when an excessive pressure is applied, an enzyme packed tower with high pressure resistance is required, and there is a problem that the immobilized enzyme is crushed due to an increase in the pressure in the tower. From the above viewpoint, although depending on the type of packing, the pressure loss per unit packing height of the enzyme (value obtained by dividing the tower top pressure by the packing thickness) is 0.04 to 1 MPa / m, more preferably 0.05 to The pressure is preferably 0.5 MPa / m. Moreover, in order to obtain the said pressure, it is preferable that the liquid flow rate at the time of slurry supply shall be 7-100 mm / min, Furthermore, 10-50 mm / min. The liquid flow rate (mm / min) is the amount of liquid fed per minute (mm ³ / min) (also referred to as the liquid feed rate (10 ⁻³ mL / min)) and the packed layer cross-sectional area (mm ² ). The value expressed by the quotient divided by.

Although it depends on the kind of packing, the packing rate in the reaction tower is preferably 0.4 to 0.55. This filling rate is represented by a value obtained by dividing the filling bulk density (kg / m ³ ) by the true density (kg / m ³ ) of the packed particles.

  When the cross-sectional area of the fixed bed is large, it is necessary to supply the mixed slurry at a large flow rate in order to obtain the liquid flow rate. However, in this method, since a strong shearing force is applied inside the pump for feeding the liquid and the immobilized enzyme may be crushed, a method of supplying the oil phase substrate to the reaction tower simultaneously with the mixed slurry is preferable. As a method of supplying simultaneously, it is preferable to carry out the mixed slurry and the oil phase substrate in different pipes directly connected to the enzyme tower. As a result, the mixed slurry can be supplied at a small flow rate to reduce the application of shearing force to the immobilized enzyme, and the oil phase substrate can be fixed at the desired filling rate by supplying the oil phase substrate at the linear velocity. The immobilized enzyme reaction tower having high enzyme activity can be obtained. In addition, it is preferable that the liquid flow rate of the oil phase substrate supplied to the reaction tower simultaneously with the mixed slurry is the same as the liquid flow rate at the time of slurry supply.

  If the obtained immobilized enzyme reaction tower is used, an enzyme reaction can be performed efficiently. The flow rate of the reaction liquid during the reaction using the obtained immobilized enzyme reaction tower is preferably 1 to 400 mm / min, more preferably 5 to 200 mm / min. Here, the reaction solution is preferably the oil phase substrate, that is, fats and oils. As the pressure in the packed column increases by increasing the liquid flow rate, liquid passing becomes difficult and an enzyme packed column with high pressure resistance is required. In addition, the immobilized enzyme is crushed by the increased pressure in the column. Since a case may arise, it is preferable that the liquid flow rate is 400 mm / min or less. Further, from the viewpoint of productivity, it is preferable that the liquid flow rate is 1 mm / min or more. Since the expression activity of the immobilized enzyme changes depending on the flow rate, the reaction can be performed according to the desired production capacity and manufacturing cost by selecting the optimal flow rate and determining the reaction conditions. it can.

  The residence time of the reaction liquid in the enzyme tower is 30 seconds to 60 minutes from the point of avoiding the equilibrium state of the hydrolysis reaction of fats and oils, more effectively drawing out the activity of the immobilized enzyme, and improving productivity. It is preferable to set to 40 minutes. The residence time (min) is represented by a value obtained by multiplying the thickness (mm) of the packed bed by the porosity and dividing this by the liquid linear velocity (mm / min).

  In the present invention, from the viewpoint of reactivity, productivity, etc., the reaction solution that has passed through the enzyme tower may be used as a reaction-finished product as it is, or a method similar to the above by adding fresh water after oil-water separation once. In this case, the same enzyme column may be supplied again until the desired reaction rate is obtained. Alternatively, once the oil / water separation is performed, it may be supplied again to another enzyme tower by the same method as described above to perform a continuous reaction. In addition, while performing oil-water separation using a plurality of enzyme towers, by supplying the oil phase to the next enzyme tower and the aqueous phase to the previous enzyme tower, the oil phase having a higher decomposition rate is replaced with a fresh water phase. You may carry out by the pseudo countercurrent method made to react. As the oil / water separation, an oil / water separator such as a natural sedimentation type or a centrifugal separation type is generally used, but is not particularly limited.

(Preparation of immobilized lipase)
1 part by weight of Duolite A-568 (manufactured by Diamond Shamrock, particle size distribution: 100 to 1000 μm) was stirred for 1 hour in 10 parts by weight of N / 10 NaOH solution. After filtration, it was washed with 10 parts by mass of ion-exchanged water, and the pH was equilibrated with 10 parts by mass of 500 mM acetate buffer (pH 7). Thereafter, the pH was equilibrated twice with 10 parts by mass of 50 mM acetate buffer (pH 7) every 2 hours. Thereafter, filtration was performed to recover the carrier, followed by ethanol replacement with 5 parts by mass of ethanol for 30 minutes. After filtration, 5 parts by mass of ethanol containing 1 part by mass of ricinoleic acid was added and ricinoleic acid was adsorbed on the carrier for 30 minutes. Thereafter, filtration was performed, and the carrier was recovered. The carrier was washed with 5 parts by mass of 50 mM acetate buffer (pH 7) four times for 30 minutes, ethanol was removed, and the carrier was recovered by filtration. Thereafter, 1 part by mass of a commercially available lipase (Lipase AY Amano Amano Pharmaceutical Co., Ltd.) was contacted with an enzyme solution dissolved in 9 parts by mass of 50 mM acetate buffer (pH 7) for 5 hours for immobilization. The immobilized enzyme was collected by filtration and washed with 10 parts by mass of 50 mM acetate buffer (pH 7) to wash the enzyme and protein that were not immobilized. Thereafter, 4 parts by mass of soybean oil to be actually decomposed was added and stirred for 12 hours. All the above operations were performed at 20 ° C. Then, it filtered and isolate | separated from fats and oils, and was set as the immobilized enzyme. An immobilized lipase having a hydrolysis activity (activity to be expressed) of 2700 U / g (dry weight) was obtained. The mass-based average particle size of the immobilized enzyme was 451 μm.

<Example 1>
A jacketed stainless steel column (inner diameter: 22 mm, height: 1500 mm) is filled with rapeseed oil, and then the slurry is mixed with 5.0 kg (dry weight) of the immobilized lipase and rapeseed oil (slurry concentration 13 wt%, dried) (Weight basis) was supplied at 0.005 L / min (in-column linear velocity 13 mm / min). The results are shown in Table 1.

<Example 2>
Stainless steel column with jacket (inner diameter 200 mm) loaded with an interior (5 steps, total height 1500 mm) with 16 square pipes of 300 mm height and a square with a cross section of 24 mm x 24 mm (wall thickness 1.5 mm) The rapeseed oil was charged to a height of 1600 mm), and then 11 kg (dry weight) of the immobilized lipase and rapeseed oil were mixed with a slurry packing (slurry concentration 5 wt%, based on dry weight) of 1.1 L / min (column The inner speed was 43 mm / min). The results are shown in Table 1.

<Example 3>
A stainless steel column with a jacket (inner diameter 685 mm) loaded with an interior (5 stages, total height 1500 mm) with 584 square pipes with a square section (wall thickness 1.5 mm) with a cross section of 24 mm x 24 mm and a height of 300 mm The rapeseed oil is charged to a height of 1600 mm, and then a slurry filling (slurry concentration 13 wt%, based on dry weight) in which 96 kg (dry weight) of the immobilized lipase and rapeseed oil are mixed is supplied at 5.7 L / min. did. While supplying the slurry, rapeseed oil was continuously supplied to the column at 5.7 L / min (in-column linear velocity 20 mm / min). The results are shown in Table 1.

<Comparative Example 1>
A stainless steel column with a jacket (inner diameter 685 mm) loaded with an interior (5 stages, total height 1500 mm) with 584 square pipes with a square section (wall thickness 1.5 mm) with a cross section of 24 mm x 24 mm and a height of 300 mm , Rapeseed oil was charged to a height of 1600 mm), and then a slurry filling (slurry concentration 13 wt%, based on dry weight) mixed with 96 kg (dry weight) of the immobilized lipase and rapeseed oil was added to 5.7 L / min (column The inner speed was 4 mm / min). The results are shown in Table 1.

<Example 4>
Using the fixed bed reactor filled with slurry in Example 3, a mixture of rapeseed oil and distilled water at a ratio of 10: 6 was fed from the top of the reactor at 320 kg / h to conduct a hydrolysis reaction. As a result, the decomposition rate of the obtained cracked oil was 88%. The decomposition rate was calculated by dividing the acid value obtained by analysis by the saponification value. The acid value was measured by American Oil Chemists. Society Official Method Ca 5a-40, and the saponification value was measured by American Oil Chemists. Society Official Method Cd 3a-94.

<Comparative example 2>
The hydrolysis reaction was carried out in the same procedure as in Example 4 using the fixed bed reactor filled with the slurry in Comparative Example 1. As a result, the decomposition rate was 62%.

  From the results shown in Table 1, it is clear that when the enzyme slurry is supplied to the fixed bed type reaction, the packing bulk density is improved by applying a pressure of a certain level or more to the packed bed, and the packing can be efficiently performed. It was. Furthermore, it has been clarified that a high enzyme expression activity can be obtained and the reaction efficiency can be improved by performing a hydrolysis reaction in a reaction tower packed using the present invention.

Claims (5)

  A method for producing an immobilized enzyme reaction tower in which an immobilized enzyme is packed in a fixed bed type reaction tower, wherein after the oil phase substrate is filled in the reaction tower, the pressure loss per unit packing height of the enzyme is zero. A method for producing an immobilized enzyme reaction tower in which a mixed slurry of an immobilized enzyme and an oil phase substrate is supplied to the reaction tower so that the pressure is 0.04 to 1 MPa / m.   The method for producing an immobilized enzyme reaction tower according to claim 1, wherein a liquid flow rate when supplying the mixed slurry of the immobilized enzyme and the oil phase substrate is 7 to 100 mm / min.   3. The method for producing an immobilized enzyme reaction tower according to claim 1, wherein when the mixed slurry of the immobilized enzyme and the oil phase substrate is supplied, the oil phase substrate is simultaneously supplied to the reaction tower.   The method for producing an immobilized enzyme reaction tower according to any one of claims 1 to 3, wherein the fixed bed type reaction tower is loaded with an interior or a pipe in which a plurality of tubular structures are formed.   The method for producing an immobilized enzyme reaction tower according to any one of claims 1 to 4, wherein the immobilized enzyme is an immobilized lipase, and the oil phase substrate is an oil or fat of vegetable oil, animal oil, or a combination thereof.