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KR20090050967A - Method for removing aldehyde compound in alcohol-containing solution and brew purified by the method - Google Patents

Method for removing aldehyde compound in alcohol-containing solution and brew purified by the method Download PDF

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KR20090050967A
KR20090050967A KR1020080112679A KR20080112679A KR20090050967A KR 20090050967 A KR20090050967 A KR 20090050967A KR 1020080112679 A KR1020080112679 A KR 1020080112679A KR 20080112679 A KR20080112679 A KR 20080112679A KR 20090050967 A KR20090050967 A KR 20090050967A
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alcohol
aldehyde compound
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KR101553281B1 (en
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유지 아사카와
후토시 야마시타
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오르가노 가부시키가이샤
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    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12HPASTEURISATION, STERILISATION, PRESERVATION, PURIFICATION, CLARIFICATION OR AGEING OF ALCOHOLIC BEVERAGES; METHODS FOR ALTERING THE ALCOHOL CONTENT OF FERMENTED SOLUTIONS OR ALCOHOLIC BEVERAGES
    • C12H1/00Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages
    • C12H1/02Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material
    • C12H1/04Pasteurisation, 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
    • C12H1/0432Pasteurisation, 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D15/00Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08Selective adsorption, e.g. chromatography
    • B01D15/26Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/36Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction, e.g. ion-exchange, ion-pair, ion-suppression or ion-exclusion
    • B01D15/361Ion-exchange
    • B01D15/363Anion-exchange
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26Synthetic macromolecular compounds

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  • Alcoholic Beverages (AREA)
  • Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

(과제) 예를 들면, 양조주와 같은 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법을 제공하고자 한다. (Problem) An object of the present invention is to provide a method for removing an aldehyde compound in an alcohol-containing solution such as brew.

(해결 수단) 알코올 함유 용액을 1급 아민형의 염기성 음이온 교환수지층에 통과시키는 것을 특징으로 하는, 알코올 함유 용액으로부터 알데하이드 화합물을 제거하는 방법을 제공한다.(Solution) Provided is a method for removing an aldehyde compound from an alcohol-containing solution, wherein the alcohol-containing solution is passed through a basic amine type basic anion exchange resin layer.

Description

알코올 함유 용액 중의 알데하이드 화합물의 제거 방법 및 상기 방법에 의해 정제된 양조주{METHOD OF REMOVING ALDEHYDE COMPOUND IN ALCOHOL-CONTAINING SOLUTION, AND BREWAGE PURIFIED BY THE METHOD}METHOD OF REMOVING ALDEHYDE COMPOUND IN ALCOHOL-CONTAINING SOLUTION, AND BREWAGE PURIFIED BY THE METHOD}

본 발명은, 예를 들면, 양조주, 증류주 등의 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법 및 상기 방법에 의해 정제된 양조주에 관한 것이다.TECHNICAL FIELD This invention relates to the removal method of the aldehyde compound in alcohol containing solutions, such as a brew and a distilled alcohol, for example, and the brew refine | purified by the said method.

예를 들면, 곡물류 등을 원료로 하여 제조되는 양조주나 증류주와 같은 알코올 함유 용액에는 주성분인 알코올 성분 외에, 향 성분, 맛 성분, 미네랄 성분, 알데하이드 화합물 등이 포함되어 있다. 그 중에서도, 알데하이드 화합물은 불쾌한 향을 부가한다. 따라서, 양조주나 증류주와 같은 주류는 용액내에 포함되어 있는 알데하이드 화합물을 제거하여, 향을 교정하는 것이 바람직하다.  For example, an alcohol-containing solution such as a brew or a distilled liquor made from grains or the like contains, in addition to an alcohol component as a main component, a flavor component, a taste component, a mineral component, an aldehyde compound and the like. Among them, the aldehyde compound adds an unpleasant odor. Therefore, liquor such as brew or distilled liquor preferably removes the aldehyde compound contained in the solution and corrects the aroma.

종래, 알코올 함유 용액에서 알데하이드 화합물을 제거하는 기술로, 예를 들면, 이온 교환수지층을 이용한 방법이 알려져 있다(특허문헌 1). 특허문헌 1의 기술에서는, 이온 교환수지층으로서 HSO3 형태의 강염기성 음이온 교환수지를 이용하여 알데하이드 화합물을 제거하는 수지층, H형 강산성 양이온 교환수지와 OH형 강 염기성 음이온 교환수지의 혼합 수지에 의한 탈염 수지층을 이용하는 소주의 정제 방법이 기재되어 있다. Conventionally, the method using the ion exchange resin layer is known as a technique of removing an aldehyde compound from an alcohol containing solution (patent document 1). In the technique of Patent Literature 1, a resin layer for removing an aldehyde compound using an HSO 3 type strong basic anion exchange resin as an ion exchange resin layer, and a mixed resin of an H type strongly acidic cation exchange resin and an OH type strong basic anion exchange resin The refinement method of the shochu liquor using the desalination resin layer by this is described.

또한, 특허문헌 2에는 주류를 HSO3 형태의 강염기성 음이온 교환수지층에 통과시켜 알데하이드 화합물을 제거한 후, H형 강산성 양이온 교환수지와 유리 염기형 약염기성 음이온 교환수지와의 혼상층(混床層)에 통과시켜 무기 염류를 제거하는, 주류의 정제 방법이 기재되어 있다.In addition, Patent Literature 2 discloses a mixed bed of H-type strongly acidic cation exchange resin and free-base weakly basic anion exchange resin after the mainstream is passed through the HSO 3 type strong basic anion exchange resin layer to remove the aldehyde compound. A process for purifying alcoholic beverages is described which removes inorganic salts by passing through).

이와같이, 종래에는 HSO3 형태의 강염기성 음이온 교환수지층을 알데하이드 화합물의 제거에 이용하여 왔다. HSO3 형태의 강염기성 음이온 수지에는 차아황산 모이어티가 이온으로서 수지층에 고정되어 있어, 차아황산 모이어티와 알데하이드 화합물의 부가 반응을 이용하여, 통과시킨 알코올 함유 용액으로부터 알데하이드 화합물을 제거한다.As described above, the HSO 3 type strong basic anion exchange resin layer has been used for the removal of the aldehyde compound. In the strong basic anion resin of the HSO 3 form, the hyposulfite moiety is fixed to the resin layer as an ion, and the aldehyde compound is removed from the alcohol-containing solution passed through the addition reaction of the hyposulfite moiety and the aldehyde compound.

그러나, HSO3 형태의 강염기성 음이온 교환수지층에서는, 통과시키는 알코올 함유 용액내에 무기 염류가 다량 포함되어 있는 경우, 무기 염류에 의한 음이온 성분으로 인해 처리액 중에 아황산이 다량으로 누출되기도 한다. 또한, 무기 염류에 의한 양이온 성분과 수지 중의 차아황산 모이어티가 염을 형성하기도 한다. 따라서, 예를 들면, 무기 염류를 별로 포함하지 않는 증류주에서는 알데하이드 화합물을 제거할 수 있지만, 무기 염류를 다량 포함하는 양조주의 경우에는 알데하이드 화합물을 제거할 수 없는 문제가 있다.However, in the HSO 3 type strong basic anion exchange resin layer, when a large amount of inorganic salts are contained in the alcohol-containing solution to be passed, a large amount of sulfurous acid may leak out of the treatment liquid due to the anion component caused by the inorganic salts. In addition, the cation component by inorganic salts and the hyposulfite moiety in resin may form a salt. Thus, for example, an aldehyde compound can be removed from a distilled liquor that does not contain much inorganic salts, but a brewing liquor containing a large amount of inorganic salts cannot remove the aldehyde compound.

특허문헌 3에는, 치환 방향족계 또는 아크릴계의 합성 흡착제를 이용하여, 주류에서 알데하이드 화합물을 제거하는 기술을 기재하고 있다. 그러나, 제거되는 알데하이드 화합물은 페닐 아세트알데하이드 등의 방향족 탄화수소기를 가진 소수성이 높은 알데하이드 화합물이며, 예를 들면 주류에 많이 포함되는 아세트알데하이드 등의 소수성이 낮은 알데하이드 화합물은 제거할 수 없다.Patent Literature 3 describes a technique for removing an aldehyde compound from the mainstream using a synthetic aromatic adsorbent of a substituted aromatic or acrylic type. However, the aldehyde compound to be removed is a high hydrophobic aldehyde compound having an aromatic hydrocarbon group such as phenyl acetaldehyde. For example, an aldehyde compound having a low hydrophobicity such as acetaldehyde contained in mainstream cannot be removed.

이상과 같은 이유로, 예컨대 양조주와 같이 무기 염류가 다량 포함된 알코올 함유 용액으로부터 알데하이드 화합물의 제거가 가능한, 알코올 함유 용액으로부터 알데하이드 화합물을 제거하는 방법이 요망되고 있다.For the reasons described above, there is a demand for a method of removing an aldehyde compound from an alcohol-containing solution that is capable of removing an aldehyde compound from an alcohol-containing solution containing a large amount of inorganic salts, such as brews.

(특허문헌 1) 특공소 36-12194호 공보 (Patent Document 1) JP 36-12194

(특허문헌 2) 특개 2005-102554호 공보(Patent Document 2) Japanese Patent Application Laid-Open No. 2005-102554

(특허문헌 3) 국제공개 제 02/004593호 팜플렛(Patent Document 3) International Publication No. 02/004593 Pamphlet

본 발명은, 예를 들면, 무기 염류를 다량 포함하는 양조주에서도 알데하이드 화합물을 효율적으로 제거할 수 있는, 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법을 제공한다. This invention provides the removal method of the aldehyde compound in an alcohol containing solution which can remove an aldehyde compound efficiently also in the brew which contains a large quantity of inorganic salts, for example.

본 발명의 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법은, 알코올 함유 용액을 1급 아민형 염기성 음이온 교환수지층에 통과시키는 것을 특징으로 한다. The method for removing an aldehyde compound in an alcohol-containing solution of the present invention is characterized by passing the alcohol-containing solution through a primary amine type basic anion exchange resin layer.

본 발명에 따른 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법은, 알코올 함유 용액으로서 양조주 또는 증류주를 이용하는 것이 바람직하다. In the method for removing an aldehyde compound in an alcohol-containing solution according to the present invention, it is preferable to use a brew or a distilled alcohol as the alcohol-containing solution.

또, 본 발명에서는 상기 방법에 의해 정제된 양조주를 제공한다.Moreover, this invention provides the brew refine | purified by the said method.

본 발명에 의하면, 예를 들면, 양조주와 같이 무기 염류가 다량 포함된 알코올 함유 용액에서 알데하이드 화합물을 효율적으로 제거할 수 있는, 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법을 제공할 수 있다. According to the present invention, for example, a method for removing an aldehyde compound in an alcohol-containing solution which can efficiently remove an aldehyde compound from an alcohol-containing solution containing a large amount of inorganic salts, such as a brew, can be provided.

이하, 본 발명의 알데하이드를 함유하는 용액에서 알데하이드 화합물을 제거하는 방법에 대해 상세히 설명한다. Hereinafter, the method of removing an aldehyde compound from the solution containing the aldehyde of this invention is demonstrated in detail.

본 발명의 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법은, 이온 교환수지층으로서 1급 아민형의 염기성 음이온 교환수지층을 이용하여, 알코올 함유 용액을 통과시키는 것을 특징으로 한다. The method for removing an aldehyde compound in an alcohol-containing solution of the present invention is characterized in that an alcohol-containing solution is passed through a basic amine type basic anion exchange resin layer as an ion exchange resin layer.

[1급 아민형 염기성 음이온 교환수지층] [Primary amine type basic anion exchange resin layer]

l급 아민 화합물은 알데하이드 화합물에 친핵성을 부가하여 이민을 형성하는 것으로 알려져 있어, 본 발명의 1급 아민형 염기성 음이온 교환수지층에서는 이러한 반응을 이용해, 알데하이드 화합물을 수지층에 고정하고, 용액을 통과시켜, 알코올 함유 용액내 알데하이드 화합물을 제거한다. 1급 아민형 염기성 음이온 교환수지층(이하, 음이온 교환수지층이라 함)으로서는, 특별히 한정되진 않지만, 스티렌계의 음이온 교환수지층인 것이, 화학적 안정성이 높기 때문에 바람직하다. 스티렌계의 음이온 교환수지층으로는, 예를 들면, 하기 식 (1)로 표시되는 구성 단위를 포함하는 화합물, 하기 식 (2)로 표시되는 구성 단위를 포함하는 화합물을 들 수 있으며, 후자가 바람직하다. It is known that the l-amine compound adds nucleophilicity to the aldehyde compound to form imine. In the primary amine-type basic anion exchange resin layer of the present invention, this reaction is used to fix the aldehyde compound to the resin layer, Pass through to remove the aldehyde compound in the alcohol containing solution. Although it does not specifically limit as a primary amine type basic anion exchange resin layer (henceforth anion exchange resin layer), It is preferable that it is a styrene type anion exchange resin layer because of high chemical stability. As a styrene type anion exchange resin layer, the compound containing the structural unit represented by following formula (1), and the compound containing the structural unit represented by following formula (2) are mentioned, for example, desirable.

(화학식 1)(Formula 1)

Figure 112008078480975-PAT00001
Figure 112008078480975-PAT00001

(화학식 2)(Formula 2)

Figure 112008078480975-PAT00002
Figure 112008078480975-PAT00002

(식 중에서, n, a, b 및 c는 각각 중합도를 의미한다.) (In the formulas, n, a, b and c each represent a degree of polymerization.)

[알코올 함유 용액][Alcohol-containing solution]

본 발명의 알데하이드 화합물의 제거 방법에서는, 음이온 교환수지층을 통과시키는 알코올 함유 용액의 pH가 2∼10인 것이 바람직하며, 4∼6인 것이 보다 바람직하다. In the removal method of the aldehyde compound of this invention, it is preferable that pHs of the alcohol containing solution which let anion exchange resin layer pass through are 2-10, and it is more preferable that it is 4-6.

1급 아민 화합물과 알데하이드 화합물의 반응은, (1) 아민이 알데하이드 화합물의 카보닐 탄소에 친핵성을 부가하고, 아민의 질소 상의 수소가 카보닐 산소로 이동하여 하이드록시기를 형성하고, (2) 상기 하이드록시기가 산 촉매에 의해 프로톤화되어 이탈함으로써 이민이 형성된다. 따라서, 통과하는 알코올 함유 용액의 pH가 2이상이면 아민이 프로톤화되는 비율이 낮아지기 때문에, (1)의 알데하이드 화합물의 친핵성 부가에 유리해지며 따라서 알데하이드 화합물의 제거 효율이 높아진다. 또, 통과하는 알코올 함유 용액의 pH가 10 이하이면, (2)의 하이드록시기의 프로톤화에 유리한 조건이 되기 때문에, 알데하이드 화합물의 제거 효율이 높아진다.The reaction between the primary amine compound and the aldehyde compound includes (1) the amine adds nucleophilicity to the carbonyl carbon of the aldehyde compound, the hydrogen on the nitrogen of the amine moves to carbonyl oxygen to form a hydroxyl group, (2) The hydroxy group is protonated by an acid catalyst to leave and imine is formed. Therefore, when the pH of the alcohol-containing solution to be passed is 2 or more, the rate at which the amine is protonated is lowered, which is advantageous for nucleophilic addition of the aldehyde compound of (1), thus increasing the removal efficiency of the aldehyde compound. Moreover, when pH of the alcohol containing solution which passes through becomes favorable condition for protonation of the hydroxyl group of (2), the removal efficiency of an aldehyde compound becomes high.

본 발명의 1급 아민형 염기성 음이온 교환수지층에 통과시키는 알코올 함유 용액으로는, 양조주나 증류주를 이용하는 것이 바람직하다. 양조주로는, 예를 들면, 일본주, 맥주, 와인, 미림 등을 들 수 있다. 증류주로는, 예컨대 소주, 위스키, 브랜디, 백주(白酒) 등을 들 수 있다. As the alcohol-containing solution passed through the primary amine type basic anion exchange resin layer of the present invention, it is preferable to use a brew or a distilled liquor. Examples of the brew include Japanese sake, beer, wine, mirin and the like. Examples of distilled spirits include shochu, whiskey, brandy, white wine, and the like.

또한, 알코올 함유 용액의 통액(通液) 온도는 ―10∼40℃인 것이 바람직하다. 알코올 농도에도 의존되지만, 통액 온도가 ―1O℃ 이상인 경우, 용액의 동결이나 점성의 증가가 없어져, 알코올 함유 용액과 수지층을 효율적으로 접촉시킬 수 있기 때문에, 알데하이드 화합물의 제거 효율이 높아진다. 또한, 통액 온도가 40℃ 이하이면, 알코올 함유 용액내 알코올 성분의 증발되지 않는다. 또한, 알코올 함유 용액내에 향기 성분이 포함되는 경우에는, 통액 온도를 40℃ 이하로 함으로써 향기 성분의 증발이나 변성을 방지할 수 있다.Moreover, it is preferable that the liquid passing temperature of an alcohol containing solution is -10-40 degreeC. Although it depends also on alcohol concentration, when liquid flow temperature is -10 degreeC or more, freezing of a solution and increase of viscosity will disappear, and alcohol-containing solution and resin layer can be contacted efficiently, and the removal efficiency of an aldehyde compound becomes high. In addition, if the liquid passing temperature is 40 degrees C or less, the alcohol component in an alcohol containing solution will not evaporate. In addition, when a fragrance component is contained in an alcohol containing solution, evaporation and denaturation of a fragrance component can be prevented by making liquid liquid temperature into 40 degrees C or less.

또한, 알코올 함유 용액의 통액 속도는 SV 0.1∼50인 것이 바람직하다. 통액 속도가 SV 0.1 이상이면 시간 당 통액량을 증대시킬 수 있다. 통액 속도를 SV50 이하로 하면, 알코올 함유 용액과 수지층과의 효율적인 접촉이 가능해지므로, 알데하이드 화합물의 제거 효율이 높아진다. Moreover, it is preferable that the flow rate of an alcohol containing solution is SV 0.1-50. If the passing rate is SV 0.1 or more, the amount of passing per hour can be increased. When the passing rate 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.

통과시키는 알코올 함유 용액은 알코올 농도가 60% 이하인 것이 바람직하다. 알코올 농도가 60% 이하이면, 음이온 교환수지가 수화된 상태가 되어 음이온 교환수지층과 액상의 알데하이드 화합물과의 접촉 효율이 양호해짐으로써, 알데하이드 화합물의 제거 효율이 높아진다. It is preferable that the alcohol containing solution to be passed has an alcohol concentration of 60% or less. When the alcohol concentration is 60% or less, the anion exchange resin becomes hydrated, and the contact efficiency between the anion exchange resin layer and the liquid aldehyde compound becomes good, thereby increasing the removal efficiency of the aldehyde compound.

또한, 본 발명에서는 이상에서 설명한 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법에 따라 정제한 양조주를 제공한다.Moreover, this invention provides the brew refine | purified according to the removal method of the aldehyde compound in the alcohol containing solution demonstrated above.

양조주는 다량의 무기 염류를 포함하고 있어, 종래의 방법으로는 통액 후 알코올 함유 용액에 아황산이 혼입되었으며, 특히 아세트알데하이드 등의 소수성이 낮은 알데하이드 화합물을 제거할 수 있는 방법이 없었다. 그러나, 본 발명의 알데하이드 화합물의 제거 방법으로는 아황산이 혼입되지 않으며, 아세트알데하이드 등의 알데하이드 화합물을 효율적으로 제거할 수 있다. The brew contains a large amount of inorganic salts, and in the conventional method, sulfuric acid is incorporated into the alcohol-containing solution after the passage, and there is no method of removing aldehyde compounds having low hydrophobicity such as acetaldehyde. However, sulfuric acid is not mixed in the method for removing the aldehyde compound of the present invention, and aldehyde compounds such as acetaldehyde can be efficiently removed.

본 발명의 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법에 따른 양조주의 정제는, 1급 아민형의 염기성 음이온 교환수지가 충전된 수지탑에 양조주를 통과시켜 접촉시킴으로써 실시한다.Purification of the brew according to the method for removing the aldehyde compound in the alcohol-containing solution of the present invention is carried out by bringing the brew into contact with a resin tower filled with a basic anion exchange resin of primary amine type.

(실시예)(Example)

이하, 본 발명에 대해 실시예 및 비교예를 들어 상세히 설명한다. 그러나, 본 발명은 이하의 기재에 의해 한정되지 않는다.Hereinafter, an Example and a comparative example are given and this invention is demonstrated in detail. However, the present invention is not limited by the following description.

알코올 함유 용액내 알데하이드 화합물의 농도 측정은 가스크로마토그래피 분석에 의해 행하였다. 또한, 알코올 함유 용액내 아황산의 농도 측정은 이온크로마토그래피 분석에 의해 행하였다.The concentration measurement of the aldehyde compound in the alcohol-containing solution was carried out by gas chromatography analysis. In addition, the measurement of the concentration of sulfurous acid in an alcohol containing solution was performed by ion chromatography analysis.

(실시예 1)(Example 1)

알코올 함유 용액으로는, 시판되고 있는 일본주(純米酒)를 사용하였다. 이 일본주의 pH는 4.5였다. 일본주의 알코올 농도는 16%이며, 함유된 알데하이드 화합물의 농도는 130mg/L였다. 이 일본주 500 ml을 하기 식 (2)의 구성 단위를 가진 1급 아민 염기성 음이온 교환수지층(시험품, 50 ml)에, 20℃에서 150 ml/hr(SV3)로 통과시켜, 알데하이드 화합물을 제거 처리하였다.As the alcohol-containing solution, commercially available Japanese sake was used. The pH of this Japanese strain was 4.5. The alcohol concentration of Japanese liquor was 16%, and the concentration of the contained aldehyde compound was 130 mg / L. 500 ml of this Japanese sake was passed through a primary amine basic anion exchange resin layer (test product, 50 ml) having the structural unit of the following formula (2) at 150 ml / hr (SV3) at 20 ° C to remove an aldehyde compound. Treated.

(화학식 3) (Formula 3)

Figure 112008078480975-PAT00003
Figure 112008078480975-PAT00003

(비교예 1)(Comparative Example 1)

실시예 1의 1급 아민 염기성 음이온 교환수지층 대신, 3급 아민형 염기성 음이온 교환수지층(앰버 라이트(등록상표) IRA96SB, 50 ml)를 이용한 것 외에는, 실시예 1과 동일한 방법으로 알데하이드 화합물의 제거 처리를 수행하였다. An aldehyde compound was prepared in the same manner as in Example 1 except that a tertiary amine type basic anion exchange resin layer (Amberlite® IRA96SB, 50 ml) was used instead of the primary amine basic anion exchange resin layer of Example 1. Removal treatment was performed.

(비교예 2)(Comparative Example 2)

실시예 1의 1급 아민 염기성 음이온 교환수지층 대신, HSO3 형태의 4급 아민형 염기성 이온 교환수지층(앰버 라이트(등록상표) IRA404, 50 ml)을 이용한 것 외에는, 실시예 1과 동일한 방법으로 알데하이드 화합물의 제거 처리를 수행하였다. The same method as in Example 1, except that HSO 3 type quaternary amine type basic ion exchange resin layer (Amberlite® 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.

이상 설명한, 실시예 1과 비교예 1-2의 평가 결과를 표 1에 나타낸다.Table 1 shows the evaluation results of Example 1 and Comparative Example 1-2 described above.

(표 1)Table 1

알코올 농도(%)Alcohol concentration (%) 알데하이드 화합물(mg/l)Aldehyde Compound (mg / l) 아황산(mg/l)Sulfurous acid (mg / l) 원액Stock solution 1616 130130 00 실시예 1Example 1 1616 3030 00 비교예 1Comparative Example 1 1616 120120 00 비교예 2Comparative Example 2 1616 <10<10 >100> 100

본 발명의 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법을 수행한 실시예 1에서는, 1급 아민 염기성 음이온 교환수지층에 통과시킨 후 일본주에 함유 된 알데하이드 화합물의 농도가 30 mg/l이 되어, 알데하이드 화합물을 고효율적으로 제거할 수 있었다. 또한, 통과 후, 일본주에 아황산의 혼입은 없었다.In Example 1 which carried out the removal method of the aldehyde compound in the alcohol containing solution of this invention, after passing through the primary amine basic anion exchange resin layer, the density | concentration of the aldehyde compound contained in Japanese sake becomes 30 mg / l, and the aldehyde The compound could be removed with high efficiency. In addition, there was no mixing of sulfurous acid in Japanese sake after the passage.

반면, 3급 아민형 염기성 음이온 교환수지층(비교예 1)에 일본주를 통과시켰을 경우, 일본주의 알데하이드 화합물 제거 효율이 낮았다.On the other hand, when Japanese sake was passed through the tertiary amine type basic anion exchange resin layer (Comparative Example 1), the aldehyde compound removal efficiency of Japanese sake was low.

또한, HSO3 형태의 4급 아민형 염기성 음이온 교환수지층(비교예 2)에 일본주를 통과시켰을 경우, 통과 후 일본주내 알데하이드 화합물의 농도가 10 mg/l 이하로 매우 낮았다. 그러나, 통과 후 일본주에 다량의 아황산(1000 mg/1 이상)이 혼입되어 있었다.In addition, when the Japanese 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 Japanese sake after the passage was very low, 10 mg / l or less. However, a large amount of sulfurous acid (1000 mg / 1 or more) was mixed in Japanese sake after the passage.

이상과 같이, 본 발명의 알코올 함유 용액에서 알데히드 화합물을 제거하는 방법을 통해 무기 염류가 다량 포함된 양조주와 같은 알코올 함유 용액에서도 알데하이드 화합물을 고효율로 제거할 수 있다.As described above, the aldehyde compound can be removed with high efficiency even in an alcohol-containing solution such as a brew containing a large amount of inorganic salts by the method of removing the aldehyde compound from the alcohol-containing solution of the present invention.

Claims (3)

알코올 함유 용액을 l급 아민형 염기성 음이온 교환수지층에 통과시키는 것을 특징으로 하는, 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법. A method for removing an aldehyde compound in an alcohol-containing solution, wherein the alcohol-containing solution is passed through a first-class amine type basic anion exchange resin layer. 제 1항에 있어서, 상기 알코올 함유 용액이 양조주 또는 증류주인 것을 특징으로 하는 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법.The method for removing an aldehyde compound in an alcohol-containing solution according to claim 1, wherein the alcohol-containing solution is a brew or a distilled spirit. 제1항 또는 제2항에 기재된 알코올 함유 용액 중의 알데하이드 화합물의 제거 방법에 의해 정제된 양조주.A brew refined by the method for removing an aldehyde compound in an alcohol-containing solution according to claim 1.
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