JP5068630B2 - Method for removing aldehyde compound from alcohol-containing solution and brewed sake purified by the method - Google Patents

Method for removing aldehyde compound from alcohol-containing solution and brewed sake purified by the method Download PDF

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JP5068630B2
JP5068630B2 JP2007296441A JP2007296441A JP5068630B2 JP 5068630 B2 JP5068630 B2 JP 5068630B2 JP 2007296441 A JP2007296441 A JP 2007296441A JP 2007296441 A JP2007296441 A JP 2007296441A JP 5068630 B2 JP5068630 B2 JP 5068630B2
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alcohol
aldehyde compound
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exchange resin
resin layer
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JP2009118781A (en
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友二 浅川
太 山下
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12H—PASTEURISATION, STERILISATION, PRESERVATION, PURIFICATION, CLARIFICATION OR AGEING OF ALCOHOLIC BEVERAGES; METHODS FOR ALTERING THE ALCOHOL CONTENT OF FERMENTED SOLUTIONS OR ALCOHOLIC BEVERAGES
    • C12H1/00—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages
    • C12H1/02—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material
    • C12H1/04—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material with the aid of ion-exchange material or inert clarification material, e.g. adsorption material
    • C12H1/0432—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material with the aid of ion-exchange material or inert clarification material, e.g. adsorption material with the aid of ion-exchange material
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/36—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction
    • B01D15/361—Ion-exchange
    • B01D15/363—Anion-exchange
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds

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Description

本発明は、例えば、醸造酒、蒸留酒等のアルコール含有溶液からのアルデヒド化合物の除去方法、及び該方法により精製された醸造酒に関する。   The present invention relates to a method for removing an aldehyde compound from an alcohol-containing solution such as brewed liquor and distilled liquor, and brewed liquor purified by the method.

例えば、穀物類等を原料として製造される醸造酒や蒸留酒といったアルコール含有溶液には、主成分であるアルコール成分の他に、香気成分、味成分、ミネラル成分、アルデヒド化合物等が含まれる。なかでも、アルデヒド化合物は不快な香りを与える。したがって、醸造酒や蒸留酒といった酒類では、溶液中に含まれているアルデヒド化合物を除去して、香りの矯正を行うのが好ましい。   For example, an alcohol-containing solution such as brewed liquor or distilled liquor produced using cereals as a raw material contains an aroma component, a taste component, a mineral component, an aldehyde compound and the like in addition to the alcohol component as a main component. Among them, aldehyde compounds give an unpleasant scent. Therefore, for alcoholic beverages such as brewed liquor and distilled liquor, it is preferable to correct the scent by removing the aldehyde compound contained in the solution.

従来、アルコール含有溶液からアルデヒド化合物を除去する技術としては、例えば、イオン交換樹脂層を用いた方法が知られている（特許文献１）。特許文献１の技術では、イオン交換樹脂層として、ＨＳＯ３形強塩基性アニオン交換樹脂を用いたアルデヒド化合物を除去する樹脂層、およびＨ形強酸性カチオン交換樹脂とＯＨ形強塩基性アニオン交換樹脂との混合樹脂による脱塩樹脂層、を用いる焼酎の精製方法が示されている。
また、特許文献２には、酒類をＨＳＯ３形強塩基性アニオン交換樹脂層に通液してアルデヒド化合物を除去した後、Ｈ形強酸性カチオン交換樹脂と遊離塩基形弱塩基性アニオン交換樹脂との混床層に通液して無機塩類を除去する、酒類の精製方法が示されている。
このように、従来、ＨＳＯ３形強塩基性アニオン交換樹脂層がアルデヒド化合物の除去に用いられている。ＨＳＯ３形強塩基性アニオン樹脂では、次亜硫酸部分をイオンとして樹脂層に固定しており、次亜硫酸部分のアルデヒド化合物への付加反応を利用し、通液したアルコール含有溶液中のアルデヒド化合物を除去する。 Conventionally, as a technique for removing an aldehyde compound from an alcohol-containing solution, for example, a method using an ion exchange resin layer is known (Patent Document 1). In the technology of Patent Document 1, as an ion exchange resin layer, a resin layer that removes an aldehyde compound using an HSO 3 type strong basic anion exchange resin, and an H type strong acidic cation exchange resin and an OH type strong basic anion exchange resin And a method for refining shochu using a desalted resin layer with a mixed resin.
In Patent Document 2, alcohol is passed through an HSO 3 type strong basic anion exchange resin layer to remove an aldehyde compound, and then an H type strong acidic cation exchange resin, a free base type weak basic anion exchange resin, A method for purifying alcoholic beverages is shown in which the solution is passed through a mixed bed layer to remove inorganic salts.
Thus, conventionally, the HSO 3 type strong basic anion exchange resin layer is used for the removal of the aldehyde compound. In the HSO 3 type strongly basic anion resin, the hyposulfite part is fixed to the resin layer as ions, and the addition reaction of the hyposulfite part to the aldehyde compound is used to remove the aldehyde compound in the passed alcohol-containing solution. To do.

しかし、ＨＳＯ３形強塩基性アニオン交換樹脂層では、通液するアルコール含有溶液中に、無機塩類が多く含まれる場合には、無機塩類によるアニオン成分によって処理液中に亜硫酸が多量に漏れ出すことがあった。また、無機塩類によるカチオン成分と、樹脂中の次亜硫酸部分が塩を形成してしまうことがあった。したがって、例えば、無機塩類をあまり含まない蒸留酒であればアルデヒド化合物が除去できるが、無機塩類を多く含む醸造酒では、アルデヒド化合物が除去できないという問題があった。 However, in the HSO 3 type strongly basic anion exchange resin layer, if the alcohol-containing solution to be passed contains a large amount of inorganic salts, a large amount of sulfurous acid leaks into the treatment liquid due to anionic components due to the inorganic salts. was there. Moreover, the cation component by inorganic salts and the hyposulfite part in resin may form a salt. Therefore, for example, an aldehyde compound can be removed with distilled liquor that does not contain much inorganic salts, but there is a problem that aldehyde compounds cannot be removed with brewed liquor that contains a large amount of inorganic salts.

特許文献３には、置換芳香族系又はアクリル系の合成吸着剤を用いて、酒類からアルデヒド化合物を除去する技術が示されている。しかし、除去されるアルデヒド化合物は、フェニルアセトアルデヒド等の芳香族炭化水素基を有する疎水性の高いアルデヒド化合物であり、例えば酒類に多く含まれるアセトアルデヒド等の疎水性の低いアルデヒド化合物は除去できない。
以上のような理由から、例えば、醸造酒のような無機塩類を多く含むアルコール含有溶液であってもアルデヒド化合物の除去が可能な、アルコール含有溶液中のアルデヒド化合物の除去方法が望まれている。
特公昭３６−１２１９４号公報 特開２００５−１０２５５４号公報 国際公開第０２／００４５９３号パンフレット Patent Document 3 discloses a technique for removing an aldehyde compound from alcoholic beverages using a substituted aromatic or acrylic synthetic adsorbent. However, the aldehyde compound to be removed is a highly hydrophobic aldehyde compound having an aromatic hydrocarbon group such as phenylacetaldehyde. For example, an aldehyde compound having low hydrophobicity such as acetaldehyde contained in a large amount of alcohol cannot be removed.
For these reasons, there is a demand for a method for removing an aldehyde compound in an alcohol-containing solution that can remove the aldehyde compound even in an alcohol-containing solution containing a large amount of inorganic salts such as brewed sake.
Japanese Patent Publication No. 36-12194 JP 2005-102554 A International Publication No. 02/004593 Pamphlet

本発明は、例えば、無機塩類を多く含有するような醸造酒であってもアルデヒド化合物が効率的に除去できる、アルコール含有溶液中のアルデヒド化合物の除去方法を提供する。   The present invention provides, for example, a method for removing an aldehyde compound from an alcohol-containing solution that can efficiently remove an aldehyde compound even in a brew that contains a large amount of inorganic salts.

本発明の醸造酒または蒸留酒中のアルデヒド化合物の除去方法は、醸造酒または蒸留酒を１級アミン形塩基性アニオン交換樹脂層に通液することを特徴とする。 The method for removing an aldehyde compound from a brewed liquor or distilled liquor according to the present invention is characterized in that the brewed liquor or distilled liquor is passed through a primary amine type basic anion exchange resin layer.

本発明によれば、例えば、醸造酒のような無機塩類を多く含有するアルコール含有溶液であっても、アルデヒド化合物を効率的に除去できる、アルコール含有溶液中のアルデヒド化合物の除去方法が提供できる。   ADVANTAGE OF THE INVENTION According to this invention, even if it is an alcohol containing solution containing many inorganic salts like brewing sake, the removal method of the aldehyde compound in the alcohol containing solution which can remove an aldehyde compound efficiently can be provided.

以下、本発明のアルコール含有溶液中のアルデヒド化合物の除去方法について詳細に説明する。
本発明のアルコール含有溶液中のアルデヒド化合物の除去方法は、イオン交換樹脂層として１級アミン形塩基性アニオン交換樹脂層を用い、アルコール含有溶液を通液することを特徴とする。 Hereinafter, the method for removing the aldehyde compound in the alcohol-containing solution of the present invention will be described in detail.
The method for removing an aldehyde compound in an alcohol-containing solution of the present invention is characterized in that a primary amine type basic anion exchange resin layer is used as the ion exchange resin layer and the alcohol-containing solution is passed through.

［１級アミン形塩基性アニオン交換樹脂層］
１級アミン化合物はアルデヒド化合物に求核付加してイミンを形成することが知られており、本発明の１級アミン形塩基性アニオン交換樹脂層ではこの反応を利用し、アルデヒド化合物を樹脂層に固定して、通液したアルコール含有溶液からアルデヒド化合物を除去する。１級アミン形塩基性アニオン交換樹脂層（以下、アニオン交換樹脂層と言うことがある。）としては、特に限定はないが、スチレン系のアニオン交換樹脂層であるのが、化学的安定性が高いために好ましい。スチレン系のアニオン交換樹脂層としては、例えば、下記式（１）で表される構成単位を有するもの、下記式（２）で表される構成単位を有するものが挙げられ、後者が好ましい。 [Primary amine type basic anion exchange resin layer]
Primary amine compounds are known to nucleophilically add to aldehyde compounds to form imines. In the primary amine type basic anion exchange resin layer of the present invention, this reaction is utilized to convert aldehyde compounds into resin layers. Fix and remove the aldehyde compound from the passed alcohol-containing solution. The primary amine-type basic anion exchange resin layer (hereinafter sometimes referred to as an anion exchange resin layer) is not particularly limited, but a styrene-based anion exchange resin layer is chemically stable. It is preferable because it is high. Examples of the styrene-based anion exchange resin layer include those having a structural unit represented by the following formula (1) and those having a structural unit represented by the following formula (2), the latter being preferred.

Figure 0005068630
Figure 0005068630
 （式中、ｎ、ａ、ｂ及びｃはそれぞれ重合度を意味する。）
Figure 0005068630
Figure 0005068630
 (In the formula, n, a, b and c each represent the degree of polymerization.)

［アルコール含有溶液］
本発明のアルデヒド化合物の除去方法では、アニオン交換樹脂層に通液するアルコール含有溶液のｐＨは２〜１０であるのが好ましく、４〜６であるのがより好ましい。
１級アミン化合物とアルデヒド化合物との反応は、（１）アミンがアルデヒド化合物のカルボニル炭素に求核付加して、アミンの窒素上の水素がカルボニル酸素へと移動してヒドロキシ基を形成し、（２）該ヒドロキシ基が酸触媒によりプロトン化されて脱離することによりイミンが形成する。したがって、通液するアルコール含有溶液のｐＨが２以上であれば、アミンがプロトン化する割合が低くなるため、（１）のアルデヒド化合物への求核付加に有利であり、アルデヒド化合物の除去効率が高くなる。また、通液するアルコール含有溶液のｐＨが１０以下であれば、（２）のヒドロキシ基のプロトン化に有利な条件となるため、アルデヒド化合物の除去効率が高くなる。 [Alcohol-containing solution]
In the aldehyde compound removal method of the present invention, the pH of the alcohol-containing solution passed through the anion exchange resin layer is preferably 2 to 10, and more preferably 4 to 6.
The reaction between the primary amine compound and the aldehyde compound is as follows: (1) The amine is nucleophilically added to the carbonyl carbon of the aldehyde compound, and the hydrogen on the nitrogen of the amine moves to the carbonyl oxygen to form a hydroxy group; 2) The hydroxy group is protonated by an acid catalyst and eliminated to form an imine. Therefore, if the pH of the alcohol-containing solution to be passed is 2 or more, the rate of protonation of the amine is low, which is advantageous for the nucleophilic addition of (1) to the aldehyde compound, and the removal efficiency of the aldehyde compound is high. Get higher. Further, if the pH of the alcohol-containing solution to be passed is 10 or less, it becomes a condition advantageous for protonation of the hydroxy group in (2), so that the removal efficiency of the aldehyde compound is increased.

本発明の１級アミン形塩基性アニオン交換樹脂層に通液するアルコール含有溶液としては、醸造酒または蒸留酒を用いるのが好ましい。醸造酒としては、例えば、日本酒、ビール、ワイン、味醂等が挙げられる。蒸留酒としては、例えば、焼酎、ウイスキー、ブランデー、白酒等が挙げられる。   As the alcohol-containing solution that is passed through the primary amine type basic anion exchange resin layer of the present invention, it is preferable to use brewed liquor or distilled liquor. Examples of brewed sake include Japanese sake, beer, wine and miso. Examples of the distilled liquor include shochu, whiskey, brandy, and white liquor.

また、アルコール含有溶液の通液温度は−１０〜４０℃とするのが好ましい。アルコール濃度にも依存するが、通液温度を−１０℃以上とすれば溶液の凍結や粘性の増加がなくなり、アルコール含有溶液と樹脂層とが効率的に接触できるため、アルデヒド化合物の除去効率が高くなる。また、通液温度を４０℃以下とすれば、アルコール含有溶液中のアルコール成分が蒸発しにくくなる。また、アルコール含有溶液中に香気成分が含まれる場合には、通液温度を４０℃以下とすることにより香気成分の蒸発や変性が起き難くなる。   Further, the passing temperature of the alcohol-containing solution is preferably −10 to 40 ° C. Although it depends on the alcohol concentration, if the liquid passing temperature is −10 ° C. or higher, freezing of the solution and increase in viscosity are eliminated, and the alcohol-containing solution and the resin layer can be efficiently contacted. Get higher. In addition, when the liquid passing temperature is 40 ° C. or lower, the alcohol component in the alcohol-containing solution is difficult to evaporate. Moreover, when an aroma component is contained in an alcohol-containing solution, evaporation and denaturation of the aroma component are difficult to occur by setting the liquid passing temperature to 40 ° C. or lower.

また、アルコール含有溶液の通液速度はＳＶ０．１〜５０とすることが好ましい。通液速度をＳＶ０．１以上とすれば、時間当たりの通液量を増大させられる。また、通液速度をＳＶ５０以下とすれば、アルコール含有溶液と樹脂層との効率的な接触が可能となり、アルデヒド化合物の除去効率が高くなる。   Moreover, it is preferable that the liquid passing rate of the alcohol-containing solution is set to SV0.1-50. If the liquid passing speed is SV0.1 or more, the liquid passing amount per hour can be increased. Further, when the liquid passing speed is set to SV50 or less, efficient contact between the alcohol-containing solution and the resin layer becomes possible, and the removal efficiency of the aldehyde compound is increased.

また、通液するアルコール含有溶液は、アルコール濃度が６０％以下であるのが好ましい。アルコール濃度を６０％以下とすれば、アニオン交換樹脂が水和された状態となり、アニオン交換樹脂層と液相のアルデヒド化合物との接触効率が良くなり、アルデヒド化合物の除去効率が高くなる。   Further, the alcohol-containing solution to be passed preferably has an alcohol concentration of 60% or less. If the alcohol concentration is 60% or less, the anion exchange resin is hydrated, the contact efficiency between the anion exchange resin layer and the liquid phase aldehyde compound is improved, and the aldehyde compound removal efficiency is increased.

また、本発明では、以上説明したアルコール含有溶液中のアルデヒド化合物の除去方法により精製した醸造酒を提供する。
醸造酒は多くの無機塩類を含むため、従来の方法では通液後のアルコール含有溶液に亜硫酸が混入しまい、特にアセトアルデヒド等の疎水性の低いアルデヒド化合物の除去方法がなかった。しかし、本発明のアルデヒド化合物の除去方法では、亜硫酸の混入もなく、アセトアルデヒドを含むアルデヒド化合物の効率的な除去が可能である。 Moreover, in this invention, the brewed liquor refine | purified by the removal method of the aldehyde compound in the alcohol containing solution demonstrated above is provided.
Since brewed liquor contains many inorganic salts, sulfur dioxide is mixed in the alcohol-containing solution after passing through, and there is no method for removing aldehyde compounds with low hydrophobicity such as acetaldehyde. However, according to the method for removing an aldehyde compound of the present invention, it is possible to efficiently remove an aldehyde compound containing acetaldehyde without mixing sulfurous acid.

本発明のアルコール含有溶液中のアルデヒド化合物の除去方法を用いた醸造酒の精製は、１級アミン形塩基性アニオン交換樹脂を充填した樹脂塔に醸造酒を通液して接触させることによって行う。   Purification of the brewed liquor using the method for removing an aldehyde compound in the alcohol-containing solution of the present invention is performed by passing the brewed liquor through a resin tower packed with a primary amine type basic anion exchange resin and bringing it into contact.

以下、本発明について実施例および比較例を示し詳細に説明する。尚、本発明は以下の記載により限定されない。
アルコール含有溶液中のアルデヒド化合物の濃度の測定は、ガスクロマトグラフィー分析により行った。また、アルコール含有溶液中の亜硫酸の濃度の測定は、イオンクロマトグラフィー分析により行った。 Hereinafter, the present invention will be described in detail with reference to examples and comparative examples. In addition, this invention is not limited by the following description.
The concentration of the aldehyde compound in the alcohol-containing solution was measured by gas chromatography analysis. The concentration of sulfurous acid in the alcohol-containing solution was measured by ion chromatography analysis.

［実施例１］
アルコール含有溶液として、市販の日本酒（純米酒）を用いた。この日本酒のｐＨは４．５であった。また、日本酒のアルコール濃度は１６％であり、含有されているアルデヒド化合物の濃度は１３０ｍｇ／ｌであった。この日本酒５００ｍｌを、下記式（２）の構成単位を有する１級アミン塩基性アニオン交換樹脂層（試験品、５０ｍｌ）に、２０℃、１５０ｍｌ／ｈｒ（ＳＶ３）で通液し、アルデヒド化合物の除去処理を行った。 [Example 1]
Commercially available sake (pure rice sake) was used as the alcohol-containing solution. The pH of this sake was 4.5. Moreover, the alcohol concentration of sake was 16%, and the concentration of the aldehyde compound contained was 130 mg / l. 500 ml of this sake is passed through a primary amine basic anion exchange resin layer (test product, 50 ml) having a structural unit of the following formula (2) at 20 ° C. and 150 ml / hr (SV3) to remove aldehyde compounds. Processed.

Figure 0005068630
Figure 0005068630

［比較例１］
実施例１の１級アミン塩基性アニオン交換樹脂層に代えて３級アミン形塩基性アニオン交換樹脂層（アンバーライト（登録商標）ＩＲＡ９６ＳＢ、５０ｍｌ）を用いた以外は、実施例１と同様の方法でアルデヒド化合物の除去処理を行った。 [Comparative Example 1]
A method similar to that of Example 1 except that a tertiary amine type basic anion exchange resin layer (Amberlite (registered trademark) IRA96SB, 50 ml) was used instead of the primary amine basic anion exchange resin layer of Example 1. Then, the aldehyde compound was removed.

［比較例２］
実施例１の１級アミン塩基性アニオン交換樹脂層に代えてＨＳＯ３形４級アミン形塩基性アニオン交換樹脂層（アンバーライト（登録商標）ＩＲＡ４０４、５０ｍｌ）を用いた以外は、実施例１と同様の方法でアルデヒド化合物の除去処理を行った。
以上説明した、実施例１〜３および比較例１〜２の評価結果を表１に示す。 [Comparative Example 2]
Example 1 except that an HSO 3 type quaternary amine type basic anion exchange resin layer (Amberlite (registered trademark) IRA404, 50 ml) was used instead of the primary amine basic anion exchange resin layer of Example 1. The removal process of the aldehyde compound was performed by the same method.
Table 1 shows the evaluation results of Examples 1 to 3 and Comparative Examples 1 and 2 described above.

Figure 0005068630
Figure 0005068630

本発明のアルコール含有溶液中のアルデヒド化合物の除去方法である実施例１では、１級アミン塩基性アニオン交換樹脂層に通液後の日本酒中に含有されるアルデヒド化合物の濃度が３０ｍｇ／ｌであり、高い効率でアルデヒド化合物が除去できた。また、通液後の日本酒中には亜硫酸が混入してない。   In Example 1, which is a method for removing an aldehyde compound from an alcohol-containing solution of the present invention, the concentration of the aldehyde compound contained in sake after passing through the primary amine basic anion exchange resin layer is 30 mg / l. The aldehyde compound could be removed with high efficiency. Sulfurous acid is not mixed in the sake after passing through.

一方、３級アミン形塩基性アニオン交換樹脂層（比較例１）に日本酒を通液した場合は、日本酒中のアルデヒド化合物の除去効率が低い。
また、ＨＳＯ３形４級アミン形塩基性アニオン交換樹脂層（比較例２）に日本酒を通液した場合は、通液後の日本酒のアルデヒド化合物の濃度が１０ｍｇ／ｌ以下と非常に低い。しかし、通液後の日本酒中に多量の亜硫酸（１０００ｍｇ／ｌ以上）が混入した。 On the other hand, when sake is passed through a tertiary amine basic anion exchange resin layer (Comparative Example 1), the removal efficiency of aldehyde compounds in sake is low.
Further, when sake was passed through the HSO 3 type quaternary amine type basic anion exchange resin layer (Comparative Example 2), the concentration of the aldehyde compound in the sake after passing was very low at 10 mg / l or less. However, a large amount of sulfurous acid (1000 mg / l or more) was mixed in the sake after passing through.

以上のように、本発明のアルコール含有溶液中のアルデヒド化合物の除去方法では、無機塩類を多く含有する醸造酒のようなアルコール含有溶液であっても、アルデヒド化合物を高い効率で除去できる。また、処理後のアルコール含有溶液中には亜硫酸が混入しない。したがって、従来、アルデヒド化合物が除去できなかった、日本酒、ビール、ワイン、味醂等の醸造酒からもアルデヒド化合物が除去でき、香りの矯正が可能となる。   As described above, according to the method for removing an aldehyde compound from an alcohol-containing solution of the present invention, an aldehyde compound can be removed with high efficiency even in an alcohol-containing solution such as brewed liquor containing a large amount of inorganic salts. Moreover, sulfurous acid does not mix in the alcohol-containing solution after the treatment. Therefore, the aldehyde compound can be removed from brewed sake such as sake, beer, wine, miso, etc., which has not been able to remove the aldehyde compound conventionally, and the scent can be corrected.

Claims (1)

醸造酒または蒸留酒を下記式（２）で表される構成単位を有する１級アミン形塩基性アニオン交換樹脂層に通液することを特徴とする、醸造酒または蒸留酒中のアルデヒド化合物の除去方法。
Figure 0005068630
 （式中、ａ、ｂ及びｃはそれぞれ重合度を意味する。） Removal of the brew or spirits, characterized in that passed through a primary amine-type basic anion exchange resin layer having a structure unit represented by the following formula (2), brew or aldehyde compound in distilled liquor Method.
Figure 0005068630
 (In the formula, a, b and c each represent the degree of polymerization.)
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