Method for manufacturing shikimic acid, apparatus for manufacturing shikimic acid

Abstract

This will enable a stable supply of shikimic acid. [Solution] The present invention provides a method for producing shikimic acid, comprising: an oil reduction step of reducing the oil content from a raw material made of plant material; an extraction step of extracting a shikimic acid extract containing shikimic acid from the raw material after the oil reduction step; a first removal step of removing amino acids and cations from the shikimic acid extract; an adsorption step of contacting the shikimic acid extract with an anion exchange resin after the first removal step to adsorb the shikimic acid contained in the shikimic acid extract onto the anion exchange resin; an elution step of eluting the shikimic acid adsorbed on the anion exchange resin to obtain a shikimic acid generating solution containing the shikimic acid; and a drying step of drying the shikimic acid generating solution.

Description

Technical Field

[0001] This invention relates to, for example, a shikimic acid production method and a shikimic acid production apparatus for producing shikimic acid from a raw material composed of plant materials.

Background Art

[0002] Shikimic acid is an organic compound produced by plants and fungi and is used as a raw material for organic synthesis, for example, as a raw material for synthesizing pharmaceuticals. In recent years, the physiological activity of shikimic acid has also attracted attention, and it is expected to be used as a raw material for cosmetics, such as the discovery of its melanin production inhibitory effect (whitening effect).

[0003] Currently, the main source of supply of shikimic acid is extracts from the fruits of Illicium verum, which account for the majority. However, Illicium verum is not only used as a raw material for synthesizing pharmaceuticals and cosmetics, but also has a high demand as a raw material for spices, fragrances, and crude drugs. In addition, there is a problem that the supply amount is not stable because the yield is greatly affected by the climate.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] The present invention has been made in view of the above problems, and an object thereof is to provide a novel shikimic acid production method and a shikimic acid production apparatus that can achieve a stable supply of shikimic acid.

Means for Solving the Problems

[0006] The present invention is a method and apparatus for producing shikimic acid, comprising: an oil reduction step of reducing the oil content from a raw material made of plant material; an extraction step of extracting a shikimic acid extract containing shikimic acid from the raw material after the oil reduction step; a first removal step of removing amino acids and cations from the shikimic acid extract; an adsorption step of contacting the shikimic acid extract with an anion exchange resin after the first removal step to adsorb the shikimic acid contained in the shikimic acid extract onto the anion exchange resin; an elution step of eluting the shikimic acid adsorbed on the anion exchange resin to obtain a shikimic acid generating solution containing the shikimic acid; and a drying step of drying the shikimic acid generating solution. [Effects of the Invention]

[0007] The present invention provides a novel method and apparatus for producing shikimic acid, which can ensure a stable supply of shikimic acid. [Brief explanation of the drawing]

[0008] [Figure 1] A schematic diagram of a manufacturing apparatus in one embodiment of the present invention. [Figure 2] Flowchart of the method for producing shikimic acid in one embodiment of the present invention. [Figure 3] A flowchart illustrating the oil content reduction process in one embodiment of the present invention. [Figure 4] Flowchart of the recycling process in one embodiment of the present invention. [Figure 5] A graph showing the shikimic acid content of each plant material. [Figure 6] A graph showing the shikimic acid content of different parts of plant material. [Modes for carrying out the invention]

[0009] One embodiment of the present invention will be described below with reference to the drawings. The present invention relates to a method for producing shikimic acid and a shikimic acid production apparatus for producing shikimic acid by processing a raw material consisting of plant material containing shikimic acid.

[0010] The raw materials used in the method and apparatus for producing shikimic acid of the present invention are plant materials containing shikimic acid. Shikimic acid is a compound, an ionic compound having a carboxyl group. As plant materials containing shikimic acid, you can use plant materials of the pine family such as Ryukyu pine, Japanese black pine, and Sakhalin fir, or plant materials of the genus Calophyllum in the family Calophyllum inophyllum. As plant materials of the genus Calophyllum, you can use Calophyllum inophyllum, Santa Maria, etc. Shikimic acid is a compound, an ionic compound having a carboxyl group.

[0011] Figure 1 is a schematic diagram of a manufacturing apparatus (shikimic acid manufacturing apparatus) 1 in one embodiment of the present invention. As shown in Figure 1, the shikimic acid manufacturing apparatus 1 includes a pulverizer 10, an oil reduction unit 11, an extraction unit 12, a first cation exchange unit 13, an anion exchange unit 14, an elution unit 15, a second cation exchange unit 16, a synthetic adsorption unit 17, a toxic substance adsorption unit 18, a spray dryer 19, a column cleaning unit 20, and a recycling unit 21.

[0012] The pulverizer 10 is not particularly limited as long as it is a machine or device capable of pulverizing plant material containing shikimic acid, and any known device can be used. For example, the pulverizer 10 can be a pulverizer that utilizes compressive force, shear force, impact force, or frictional force.

[0013] The oil reduction unit 11 is provided to reduce the oil content of the raw material. The oil reduction unit 11 can be configured according to the type of oil (volatile oil, non-volatile vegetable oil, etc.) contained in the raw material. For example, the oil reduction unit 11 can be composed of a steam distillation apparatus, a solvent extraction apparatus, and a seed separation apparatus. The steam distillation apparatus can remove oil from plant materials that contain a large amount of volatile oil. The solvent extraction apparatus can remove oil from plant materials that contain a large amount of non-volatile vegetable oil. The seed separation apparatus separates seeds from plant materials that mainly contain oil only in the seeds. This reduces the oil content of the raw material by using parts other than the seeds as the raw material. Known apparatuses can be used for each of the steam distillation apparatus, solvent extraction apparatus, and seed separation apparatus.

[0014] The extraction unit 12 is provided to extract an extract containing shikimic acid (shikimic acid extract) from the raw material after the oil content has been reduced in the oil content reduction unit 11. The extraction unit 12 may include a container (tank) for holding the raw material, a water addition device for adding water to the raw material, a solvent supply device for supplying solvent, etc., as needed.

[0015] The first cation exchange section 13 and the second cation exchange section 16 are provided to exchange cations in the shikimic acid extract or the shikimic acid production solution (described later) with other cations. The first cation exchange section 13 and the second cation exchange section 16 have a cation exchange resin. The cation exchange resin is a resin that uses a crosslinked polymer as a resin matrix and has cation exchange groups. Examples of cation exchange resins include resins having acidic groups such as carboxyl groups (-COOH) and sulfo groups (-SO3H) in the side chains of the polymer chains. For example, the first cation exchange section 13 and the second cation exchange section 16 can each be configured in the form of a column-type structure (cation exchange resin tower). The cation exchange resin tower has a resin storage section in the flow path, and the resin storage section is filled with cation exchange resin. The cation exchange resin tower in the first cation exchange section 13 (first cation exchange resin tower) and the cation exchange resin tower in the second cation exchange section 16 (second cation exchange resin tower) are configured separately.

[0016] The anion exchange section 14 is provided to adsorb shikimic acid contained in the shikimic acid extract after cation exchange treatment in the first cation exchange section 13. For example, the anion exchange section 14 has an anion exchange resin. The anion exchange resin is a resin that uses a crosslinked polymer as a resin base and has anion exchange groups. Examples of anion exchange resins include anion exchange resins that use a styrene-based resin as a base and have quaternary ammonium groups or amino groups as anion exchange groups. For example, the anion exchange section 14 is configured in the form of a column type structure (anion exchange resin column). The anion exchange resin column has a resin storage section in the flow path, and the resin storage section is filled with anion exchange resin.

[0017] The elution unit 15 is provided to elute shikimic acid adsorbed on the anion exchange resin in the anion exchange unit 14 to obtain a product solution containing shikimic acid (shikimic acid product solution). For example, since hydrochloric acid can be used for eluting shikimic acid, the elution unit 15 has a hydrochloric acid supply device or the like that supplies hydrochloric acid. The shikimic acid product solution after being processed by the elution unit 15 is subjected to cation exchange treatment in the second cation exchange unit 16.

[0018] The synthetic adsorption unit 17 has a synthetic adsorbent and is provided to remove aromatic carboxylic acids from the shikimic acid product solution after being subjected to cation exchange treatment in the second cation exchange unit 16. As the synthetic adsorbent, a hydrophobic synthetic adsorbent can be used. For example, the synthetic adsorption unit 17 can be configured in the form of a column type structure (synthetic adsorbent packed tower). The synthetic adsorbent packed tower has an adsorbent storage section provided in the flow path, and the adsorbent storage section is filled with the synthetic adsorbent.

[0019] The toxic substance adsorption unit 18 has a toxic substance adsorbent and is provided to remove toxic substances such as anisatin or neoanisatin from the shikimic acid product solution. As the toxic substance adsorbent, an ODS (octadecylsilane) - based compound can be used. For example, the toxic substance adsorption unit 18 can be configured in the form of a column type structure (toxic substance adsorbent packed tower). The toxic substance adsorbent packed tower has an adsorbent storage section provided in the flow path, and the adsorbent storage section is filled with the toxic substance adsorbent.

[0020] The spray dryer 19 is provided to obtain powdery shikimic acid by volatilizing the moisture of the shikimic acid product solution. For example, the spray dryer 19 has a function of discharging hot air, and dries the shikimic acid product solution with hot air to obtain powdery shikimic acid.

[0021] The column cleaning unit 20 is provided to clean the inside of each resin column or packed column with pure water. The column cleaning unit 20 has a pure water supply device that supplies pure water, and a predetermined amount of pure water is supplied to the inside of each resin column or packed column to clean the inside of each resin column or packed column.

[0022] The recycling unit 21 is provided to recover and reuse the treated water (washing water) after washing each column (anion exchange resin column, second cation exchange resin column, synthetic adsorbent packed column, toxic substance adsorbent packed column) following the anion exchange resin column. Since the washing water may contain shikimic acid that remained in each column, the recycling unit 21 is configured to generate a recycled liquid (corresponding to a shikimic acid extract) containing shikimic acid from the recovered washing water and return the recycled liquid to the first removal process (step S4). Specifically, the recycling unit 21 has a recycling column configured in a column-type structure packed with anion exchange resin. In the recycling unit 21, shikimic acid contained in the washing water is adsorbed onto the anion exchange resin packed in the recycling column, and the shikimic acid adsorbed on the anion exchange resin is eluted with hydrochloric acid or the like to obtain a recycled liquid.

[0023] The configuration of the shikimic acid production apparatus 1 described above is merely an example and is not limited to it. For example, the shikimic acid production apparatus 1 may have a configuration for treating the waste liquid generated when shikimic acid is adsorbed onto the anion exchange unit 14 (waste liquid treatment unit). Furthermore, the configuration of the shikimic acid production apparatus 1 described above can be separated into multiple devices to form a shikimic acid production system composed of multiple devices.

[0024] The following describes the method for producing shikimic acid according to the present invention. Figure 2 is a flow chart of the method for producing shikimic acid according to one embodiment of the present invention. Figure 3 is a flow chart showing the contents of the oil content reduction treatment according to one embodiment of the present invention.

[0025] As shown in Figure 2, the method for producing shikimic acid according to the present invention consists of a grinding step (step S1), an oil content reduction step (step S2), a shikimic acid extraction step (step S3), a first removal step (step S4), an adsorption step (step S5), an elution step (step S6), a second removal step (step S7), an aromatic carboxylic acid removal step (step S8), a toxic substance removal step (step S9), and a drying step (step S10). Each step will be described below.

[0026] In the grinding process (step S1), the plant material containing shikimic acid is ground to a predetermined size using the grinder 10. In the grinding process (step S1), the plant material should be ground (roughly ground) so that the particle size after grinding is approximately 2 to 5 mm. The plant material (ground material) ground in the grinding process (step S1) is used as the raw material for shikimic acid.

[0027] In the oil content reduction process (step S2), the oil content of the raw material is reduced according to the type of raw material (type of oil contained in the raw material). As shown in Figure 3, in the oil content reduction process (step S2), if the plant material used as the raw material contains seeds, a decision is made as to whether or not to separate the seeds (step S11). In step S11, if the plant material used as the raw material is a plant material of the genus Calophyllum and is a fruit containing seeds, it is desirable to separate the seeds. However, even if the plant material is of the genus Calophyllum, if it is only a part that does not contain seeds (fruit peel, leaves, branches, etc.), it is not necessary to separate the seeds. Even if the plant material used as the raw material is a fruit of the genus Calophyllum containing seeds, the decision of whether or not to separate the seeds should be made as necessary, taking into consideration the manufacturing equipment, manufacturing costs, etc.

[0028] If seeds are to be separated (Step S11: YES), the seed separation process (Step S12) is performed, and the process proceeds to Step S13, which will be described later. In the seed separation process (Step S12), a rotary or sliding seed separation device is used to separate the fruit into the seed portion and the non-seed portion (pericarp). After the seed separation process (Step S12), the seeds can be discarded and only the non-seed portion can be used as raw material, or both the seeds and the non-seed portion can be used as raw material. Once the seed separation process (Step S12) is completed, the process proceeds to Step S13.

[0029] In step S13, it is determined whether the raw material contains a large amount of volatile oil. If the raw material contains a large amount of volatile oil (step S13: YES), a de-oiling process by steam distillation (step S14) is performed using a steam distillation apparatus, and the oil content reduction process (step S2) is terminated. For example, if plant material from the pine family is used as the raw material, the raw material contains a large amount of volatile oil, so de-oiling by steam distillation is performed.

[0030] Furthermore, if the raw material does not contain a large amount of volatile oil (Step S13: NO), it is determined whether the raw material contains a large amount of vegetable oil (non-volatile vegetable oil) (Step S15). If the raw material contains a large amount of non-volatile vegetable oil (Step S15: YES), a de-oiling process using an organic solvent is performed using a solvent extraction apparatus (Step S16), and a desolvation process (Step S17) is performed to remove the organic solvent and leave only the raw material, thus ending the oil content reduction process (Step S2). For example, if seeds of a plant material of the genus Calophyllum are used as the raw material, the raw material contains a large amount of non-volatile vegetable oil, so de-oiling with an organic solvent is performed. The same applies when not only seeds but also the entire fruit including the seeds is used as the raw material, or when various parts including the seeds of a plant material of the genus Calophyllum are mixed together.

[0031] Furthermore, if the raw material does not contain a large amount of non-volatile vegetable oil (step S15: NO), that is, if the raw material does not contain either volatile or non-volatile vegetable oil, the oil reduction process (step S2) is terminated. For example, if, after the seed separation process (step S12), the seeds are discarded and only the parts other than the seeds are used as raw material, the raw material will not contain either volatile or non-volatile vegetable oil. In other words, the seed separation process (step S12) can also be considered a type of oil reduction process (oil reduction means).

[0032] In the shikimic acid extraction step (step S3), the extraction unit 12 extracts a shikimic acid extract, which is a liquid containing shikimic acid, from the raw material whose oil content has been reduced in the oil content reduction step (step S2). For example, the shikimic acid extract is extracted from the raw material by a hot water reflux extraction method. Specifically, the raw material is placed in a reaction vessel together with a predetermined amount of water, the mixture of raw material and water in the reaction vessel is heated under reflux cooling at 60°C to 98°C, and after the extraction reaction is completed, the mixture of raw material and water is filtered to obtain the shikimic acid extract.

[0033] In the first removal step (step S4), the shikimic acid extract is brought into contact with the cation exchange resin of the first cation exchange unit 13. As a result, the amino acids contained in the shikimic acid extract are adsorbed onto the cation exchange resin, and the cations contained in the shikimic acid extract are converted into hydrogen ions (H) by the action of the cation exchange resin. + ) is substituted. Therefore, amino acids and cations can be removed from the shikimic acid extract.

[0034] In the adsorption step (step S5), after the first removal step (step S4), the shikimic acid extract from which amino acids and cations have been removed in the first removal step is brought into contact with the anion exchange resin of the anion exchange unit 14, thereby adsorbing the shikimic acid contained in the shikimic acid extract onto the anion exchange resin. Furthermore, by treating the shikimic acid extract with the anion exchange resin, all nonionic compounds can be removed from the shikimic acid extract, as can all water-insoluble substances (such as fine particles).

[0035] In the elution step (step S6), the shikimic acid adsorbed on the anion exchange resin of the anion exchange unit 14 is eluted by the elution unit 15 to obtain a shikimic acid generating solution containing shikimic acid. For example, in the elution step (step S6), hydrochloric acid is used to elute the shikimic acid from the anion exchange unit 14. In order to efficiently elute the shikimic acid from the anion exchange resin at this time, the concentration of the hydrochloric acid should be 1 mol / L (1N).

[0036] In the second removal step (step S7), after the elution step (step S6), the shikimic acid product obtained in the elution step (step S6) is brought into contact with the cation exchange resin of the second cation exchange unit 16. The effect of the second removal step (step S7) is the same as that of the first removal step (step S4), and amino acids and cations can be removed from the shikimic acid product. In the first removal step (step S4), amino acids and cations are almost completely removed from the shikimic acid extract, which is the base of the shikimic acid product, but if only the first removal step (step S4) is performed, amino acids and cations may remain in the shikimic acid extract. The second removal step (step S7) can completely or almost completely remove amino acids and cations from the shikimic acid product.

[0037] In the aromatic carboxylic acid removal step (step S8), the shikimic acid production solution is brought into contact with the synthetic adsorbent in the synthetic adsorption section 17 to remove the aromatic carboxylic acids contained in the shikimic acid production solution.

[0038] In the toxic substance removal step (step S9), toxic substances such as anisatin or neoanisatin contained in the shikimic acid production solution are removed by bringing the shikimic acid production solution into contact with the toxic substance adsorbent of the toxic substance adsorption section 18.

[0039] As described above, by going through the second removal step (step S7), the aromatic carboxylic acid removal step (step S8), and / or the toxic substance removal step (step S9), a purified shikimic acid solution can be obtained by removing impurities from the shikimic acid product solution. The second removal step (step S7), the aromatic carboxylic acid removal step (step S8), and the toxic substance removal step (step S9) can also be collectively referred to as the purification step.

[0040] In the drying step (step S10), the shikimic acid generating solution or the shikimic acid purified solution containing shikimic acid is dried with hot air using a spray dryer 19 to obtain powdered shikimic acid. In other words, according to the shikimic acid production method of the present invention, powdered shikimic acid can be obtained (produced) from plant material containing shikimic acid by going through the above steps.

[0041] The order of the steps described above is merely an example and is not limited to this; the order of the steps can be changed. For example, when performing the seed separation step (step S12), the pulverization step (step S1) may be performed after the oil content reduction step (step S2). Also, the order of the second removal step (step S7), the aromatic carboxylic acid removal step (step S8), and the toxic substance removal step (step S9) can be changed as appropriate.

[0042] The present disclosure will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. [Example 1] 10 kg of the mesocarp of Calophyllum inophyllum was prepared as the raw material. The raw material was coarsely ground using a grinding device. The particle size of the ground material was approximately 2 mm. Since only the mesocarp of Calophyllum inophyllum was used, the oil content reduction process was omitted. Subsequently, 10 L of shikimic acid extract was obtained by hot water reflux extraction. The 10 L of shikimic acid extract was passed through a column packed with cation exchange resin (Amberlite® IR120B (product name), manufactured by Organo Corporation) for 2 hours, and then the 10 L of shikimic acid extract was passed through a column packed with anion exchange resin (Amberlite® IRA400 (product name), manufactured by Organo Corporation) for 2 hours. This allowed shikimic acid and amino acids to be adsorbed onto the anion exchange resin. Then, 1 N hydrochloric acid was used to elute the shikimic acid adsorbed onto the anion exchange resin. This process took approximately 2 hours. The resulting shikimic acid solution was passed through a column packed with cation exchange resin (Amberlite® IR120B (product name), manufactured by Organo Corporation) for approximately 2 hours. Subsequently, the shikimic acid solution was passed through a column packed with hydrophobic synthetic adsorbent (Diaion® HP20 (product name), manufactured by Mitsubishi Chemical Corporation) and then through a column packed with ODS-based compounds. Through these steps, 12 L of shikimic acid solution (purified shikimic acid solution) was obtained. After that, the water in the shikimic acid solution was evaporated using a spray dryer. As a result, 1 kg of shikimic acid was obtained.

[0043] The present invention provides a method for producing shikimic acid, which includes a first removal step (step S4) to remove amino acids and cations from a shikimic acid extract, an adsorption step (step S5) to adsorb the shikimic acid contained in the extract onto an anion exchange resin after the first removal step (step S4), an elution step (step S6) to elute the shikimic acid adsorbed onto the anion exchange resin to obtain a shikimic acid product containing the shikimic acid, and a drying step (step S10) to dry the shikimic acid product. In this way, since amino acids and cations are removed from the shikimic acid extract before the adsorption step (step S5), the amount of washing water required for column washing after the adsorption step (step S5) can be reduced. Specifically, compared to conventional methods, when the same amount of raw material is processed, the amount of shikimic acid product obtained after the elution step (step S6) is reduced to 1 / 10 to 1 / 20. That is, a shikimic acid product with a high concentration of shikimic acid (high-concentration shikimic acid product) can be obtained. Therefore, it is possible to efficiently produce shikimic acid and ensure a stable supply of shikimic acid. Furthermore, in conventional methods, the concentration of shikimic acid in the shikimic acid production solution was low, requiring a concentration step. However, the method of the present invention eliminates the need for a concentration step, allowing for the extremely efficient production of shikimic acid.

[0044] Furthermore, according to the present invention, after the elution step (step S6), a second removal step (step S7) is performed to remove amino acids and cations from the shikimic acid production solution. As a result, amino acids and cations can be completely or almost completely removed from the shikimic acid production solution and the dried shikimic acid.

[0045] Furthermore, according to the present invention, after the elution step (step S6), a toxic substance removal step (step S9) is performed to remove toxic substances from the shikimic acid production solution. Therefore, toxic substances can be removed from the shikimic acid production solution and the dried shikimic acid.

[0046] Furthermore, according to the present invention, if the plant material is from the genus Calophyllum, the oil content reduction step (step S2) can be a seed separation step (step S12) in which the fruit is separated into seeds and non-seed parts, and the non-seed parts are used as the raw material. In this case, the oil removal step by steam distillation (step S14) or the oil removal step by organic solvent (step S16) can be omitted, eliminating the need for large-scale equipment and enabling the efficient production of shikimic acid.

[0047] Furthermore, the present invention allows for the recycling of treated wastewater in parallel with the shikimic acid production method described above. Figure 4 is a flowchart of the washing water recycling method in one embodiment of the present invention.

[0048] As shown in Figure 4, the present invention's method for recycling treated wastewater consists of a treated wastewater supply step (step S21), a treated wastewater recovery step (step S22), an elution step (step S23), and a recycled liquid supply step (step S24). Each step will be described below.

[0049] In the washing water supply process (step S21), a predetermined amount of pure water is supplied to the inside of each resin column or packed column by the column washing unit 20 (pure water supply device) to wash the inside of each resin column or packed column.

[0050] In the washing treatment water recovery process (step S22), the recycling unit 21 recovers the treated water (washing treatment water) after washing each column from the anion exchange resin column onward (from the anion exchange resin column onward, the second cation exchange resin column, the synthetic adsorbent packed column, and the toxic substance adsorbent packed column), and adsorbs the shikimic acid contained in the washing treatment water onto the anion exchange resin of the recycling unit 21.

[0051] In the elution step (step S23), shikimic acid adsorbed on the anion exchange resin of the recycling unit 21 is eluted with hydrochloric acid or the like to obtain a recycled liquid. At this time, the concentration of the hydrochloric acid can be, for example, 1 mol / L (1N).

[0052] In the recycling liquid supply process (step S24), the recycling liquid obtained in the elution process (step S23) is supplied to the first cation exchange unit 13. In other words, the recycling liquid obtained in the elution process (step S23) is returned to the cation exchange treatment.

[0053] According to the present invention, by implementing a recycling treatment method for wash treatment water, the shikimic acid contained in the wash treatment water can be returned to the middle of the shikimic acid production process, thereby ensuring that all shikimic acid contained in the raw materials is utilized without waste. In other words, the ratio of the amount of shikimic acid actually obtained to the amount of raw materials input can be increased, thereby increasing the amount of shikimic acid produced and ensuring a stable supply of shikimic acid.

[0054] In this invention, the oil content reduction step corresponds to the oil content reduction step (step S2), and similarly, the extraction step corresponds to the shikimic acid extraction step (step S3), the first removal step corresponds to the first removal step (step S4), the adsorption step corresponds to the adsorption step (step S5), the elution step corresponds to the elution step (step S6), the drying step corresponds to the drying step (step S10), the second removal step corresponds to the second removal step (step S7), the third removal step corresponds to the toxic substance removal step (step S9), the seed separation step corresponds to the seed separation step (step S12), and the oil content reduction unit corresponds to the oil content reduction unit 11. The extraction unit corresponds to the extraction unit 12, the first cation exchange resin corresponds to the first cation exchange resin of the first cation exchange unit 13, the anion exchange resin corresponds to the anion exchange resin of the anion exchange unit 14, the elution unit corresponds to the elution unit 15, the spray dryer corresponds to the spray dryer 19, the second cation exchange resin corresponds to the second cation exchange resin of the second cation exchange unit 16, the toxic substance adsorbent corresponds to the toxic substance adsorbent of the toxic substance adsorption unit 18, and the shikimic acid production apparatus corresponds to the shikimic acid production apparatus 1. However, this invention is not limited to this embodiment and can take many other forms. Furthermore, the specific configurations and other details listed in the above-described embodiment are just examples and can be modified as appropriate according to the actual product.

[0055] Furthermore, the present invention can be provided not only as a method for producing shikimic acid, but also as a shikimic acid production apparatus for realizing the shikimic acid production method. Moreover, the present invention can be provided as a novel method for extracting shikimic acid. For example, the invention of claim 1 can be a method for extracting shikimic acid from a raw material consisting of plant material of the genus Calophyllum. The invention of claim 2 can be the shikimic acid extraction method according to claim 1, wherein the fruit peel, leaves, or branches of the plant material of the genus Calophyllum are used as the raw material. The invention of claim 3 can be the shikimic acid extraction method according to claim 1 or 2, wherein the plant material is in a blue or green state before discoloration is used as the raw material. The invention of claim 4 can be the shikimic acid extraction method according to claim 1, 2, or 3, wherein the fruit peel is within 90 days of fruiting as the raw material. The invention of claim 5 can be the shikimic acid extraction method according to any one of claims 1 to 4, wherein the fruit peel is 30 days or more after fruiting as the raw material. The invention of claim 6 can be expressed as a method for extracting shikimic acid according to any one of claims 1 to 5, wherein the mesocarp of the plant material is used as the raw material.

[0056] Figure 5 is a graph showing the shikimic acid content of each plant material. Figure 6 is a graph showing the shikimic acid content of each part of the plant material. As shown in Figure 5, the pericarp of Calophyllum inophyllum had a particularly high accumulation of shikimic acid at 172.1 mg / gDW, exceeding the shikimic acid content of approximately 120 mg / gDW in the fruit of Illicium anisatum, which is used as the main source of shikimic acid. In addition, Pine ryukyuensis also contained shikimic acid at 17.5 mg / gDW, and Calophyllum inophyllum contains a very high amount of shikimic acid compared to Pine cypress's 9.9 mg / gDW (leaves). Furthermore, as shown in Figure 6, high levels of shikimic acid were also found in the leaves (80.1 mg / gDW) and branches (23.4 mg / gDW) of Calophyllum inophyllum, in addition to the pericarp. The shikimic acid content of Calophyllum inophyllum leaves exceeded that of Calophyllum santa 'Maria', a species of Calophyllum considered promising as an alternative source of shikimic acid (37.9 mg / g DW / leaf). Furthermore, while the fruit of Illicium anisatum is harvested only once a year, Calophyllum inophyllum is a reblooming plant that bears fruit two or three times a year, and is also an evergreen tree whose branches and leaves can be used, making it possible to obtain raw materials throughout the year. For these reasons, Calophyllum inophyllum is a promising source of shikimic acid due to its stable supply.

[0057] Therefore, a stable supply of shikimic acid can be achieved by extracting it from raw materials made from plant materials of the genus Calophyllum. Furthermore, shikimic acid can be produced efficiently by using the pericarp, leaves, or branches of the plant material of the genus Calophyllum, which are parts in which shikimic acid accumulates in high concentrations, as the raw material. In addition, since the pericarp, leaves, or branches of the plant material of the genus Calophyllum have a very low oil content, there is also the advantage that the oil reduction process can be omitted. Moreover, shikimic acid can be produced even more efficiently by using the pericarp of the plant material of the genus Calophyllum, which is a part in which shikimic acid accumulates in particularly high concentrations, as the raw material. In particular, it is preferable to use the mesocarp of the plant material of the genus Calophyllum as the raw material. Furthermore, when using the pericarp, leaves, or branches of the plant material of the genus Calophyllum as the raw material, it is preferable to use those in their blue or green state before discoloration. The shikimic acid content of the pericarp of the plant material of the genus Calophyllum decreases after 90 days from fruiting compared to when it is less than 90 days from fruiting. Therefore, when using the pericarp of a plant material belonging to the genus Calophyllum as a raw material, it is preferable to use pericarp that has been used within 90 days of fruiting. Furthermore, the shikimic acid content of the pericarp of a plant material belonging to the genus Calophyllum increases after 30 days from fruiting compared to less than 30 days from fruiting, and increases even further after 60 days from fruiting compared to less than 60 days from fruiting. Therefore, when using the pericarp of a plant material belonging to the genus Calophyllum as a raw material, it is preferable to use pericarp that has been used for 30 days or more from fruiting, and more preferably pericarp that has been used for 60 days or more from fruiting. In addition, when using the leaves of a plant material belonging to the genus Calophyllum as a raw material, it is possible to use leaves that have not fallen, and it is preferable to use undiscolored blue or green leaves. [Industrial applicability]

[0058] The present invention can be used in the industry for the production of shikimic acid. [Explanation of Symbols]

[0059] 1...Shikimic acid production equipment 10... Crusher 11…Oil reduction section 12...Extraction part 13…First cation exchange section 14…Anion exchange section 15... Melting part 16…Second cation exchange section 17…Synthetic adsorption part 18…Toxic substance adsorption part 19... Spray dryer 20... Column washing section 21…Recycling Department

Claims

1. An oil reduction process that reduces the oil content from raw materials made from plant materials, After the oil content reduction step, an extraction step is performed to extract a shikimic acid extract containing shikimic acid from the raw material. A first removal step of removing amino acids and cations from the shikimic acid extract, After the first removal step, an adsorption step is performed in which the shikimic acid contained in the shikimic acid extract is brought into contact with an anion exchange resin, thereby adsorbing the shikimic acid contained in the shikimic acid extract onto the anion exchange resin. An elution step to obtain a shikimic acid generating solution containing the shikimic acid by eluting the shikimic acid adsorbed on the anion exchange resin, A drying step is performed to dry the shikimic acid production solution. Shikimic acid production method.

2. After the elution step, a second removal step is performed to remove amino acids and cations from the shikimic acid-producing solution. The method for producing shikimic acid according to claim 1.

3. After the elution step, a third removal step is performed to remove toxic substances from the shikimic acid product. The method for producing shikimic acid according to claim 2.

4. The aforementioned plant material is a plant material of the genus Calophyllum, The oil content reduction step includes a seed separation step in which the fruit is separated into seeds and non-seed parts, and the non-seed parts are used as the raw material. A method for producing shikimic acid according to any one of claims 1 to 3.

5. An oil reduction unit that reduces the oil content from raw materials made from plant materials, An extraction unit extracts a shikimic acid extract containing shikimic acid from the raw material from which the oil content has been reduced in the oil content reduction unit, A first cation exchange resin for removing amino acids and cations from the shikimic acid extract, An anion exchange resin for adsorbing the shikimic acid extract from which amino acids and cations have been removed using the first cation exchange resin, An elution unit for eluting the shikimic acid adsorbed on the anion exchange resin to obtain a shikimic acid generating solution containing the shikimic acid, The system includes a spray dryer for drying the shikimic acid-producing solution. Shikimic acid production equipment.

6. The system further comprises a second cation exchange resin that removes amino acids and cations from the aforementioned shikimic acid production solution. The apparatus for producing shikimic acid according to claim 5.

7. The invention further comprises a toxic substance adsorbent for removing toxic substances from the aforementioned shikimic acid production solution. The apparatus for producing shikimic acid according to claim 6.

8. The aforementioned plant material is a plant material of the genus Calophyllum, The oil reduction unit has a seed separation unit that separates the fruit into seeds and non-seed parts. A shikimic acid production apparatus according to any one of claims 5 to 7.

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