CN101434900B - Method for removing aldehydes compound in alcohol-containing solution and brewed liquor - Google Patents

Method for removing aldehydes compound in alcohol-containing solution and brewed liquor Download PDF

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Publication number
CN101434900B
CN101434900B CN2008101734581A CN200810173458A CN101434900B CN 101434900 B CN101434900 B CN 101434900B CN 2008101734581 A CN2008101734581 A CN 2008101734581A CN 200810173458 A CN200810173458 A CN 200810173458A CN 101434900 B CN101434900 B CN 101434900B
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aldehyde compound
solution
spirituosity
resin layer
exchange resin
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CN101434900A (en
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浅川友二
山下太
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PRGANO CORP
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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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Food Science & Technology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
  • Alcoholic Beverages (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides a method for removing aldehyde compound in solution containing alcohol in order to remove the aldehyde compound from solution containing alcohol such as solution for brewage, which is characterized in that the method leads the solution containing alcohol into a primary amine typed alkali anion exchange resin layer.

Description

Remove method and the brewing wine of the aldehyde compound in spirituosity solution
Technical field
The present invention relates to a kind ofly remove the method for aldehyde compound and utilize the refining brewing wine that forms of the method from the solution such as the spirituosity such as brewing wine, liquor.
Background technology
In the spirituosity solution such as the brewing wine of making take such as grain etc. as raw material, liquor, except containing the alcoholic content as principal constituent, contain simultaneously aroma component, flavor composition, mineralogical composition, aldehyde compound etc.Aldehyde compound wherein will bring unhappy smell.Therefore, in the drinks such as brewing wine, liquor, preferably remove the aldehyde compound that comprises in its solution, carry out fragrance and correct.
As removing the traditional technology of aldehyde compound from spirituosity solution, the known method (patent documentation 1) that for example adopts resinbed.In the technique of patent documentation 1, the process for purification that adopts following resin layer as resinbed, liquor to be made with extra care is disclosed.Wherein, described resin layer is: utilize HSO 3The type strongly basic anion exchange resin is removed the resin layer of aldehyde compound and is utilized H type storng-acid cation exchange resin and the desalination resin layer of the hybrid resin of OH type strongly basic anion exchange resin.
In addition, following drinks process for purification is disclosed: drinks solution is passed into HSO in patent documentation 2 3After the type strongly basic anion exchange resin is removed aldehyde compound, then the mixolimnion that passes into H type storng-acid cation exchange resin and free alkali type weak base anion-exchange resin is removed inorganic salts.
As mentioned above, traditionally, HSO 3Type strongly basic anion exchange resin layer is used to remove aldehyde compound.At HSO 3In the type strongly basic anionic resin, the SODIUM HYDROSULPHITE unit is fixed on resin layer as ion, utilizes this SODIUM HYDROSULPHITE unit can remove aldehyde compound from the spirituosity solution that passes into resin layer to the addition reaction of aldehyde compound.
, at HSO 3In type strongly basic anion exchange resin layer, when containing a large amount of inorganic salts in the spirituosity solution that passes into resin layer, the anionic component in inorganic salts may cause a large amount of losses of sulfurous acid in treatment solution.In addition, the cation constituent in inorganic salts also may with resin in the SODIUM HYDROSULPHITE unit form salt.Therefore, the problem of existence is: if the less liquor that contains inorganic salts can be removed aldehyde compound wherein; If contain the brewing wine of a large amount of inorganic salts, can't remove aldehyde compound wherein.
In patent documentation 3, the technique that adopts the substituted aroma same clan or acrylic acid or the like synthetic adsorbent to remove aldehyde compound from drinks is disclosed.But, because the aldehyde compound that is removed is the high hydrophobicity aldehyde compound that phenylacetic aldehyde etc. has aryl radical, can't remove such as the low hydrophobicity aldehyde compounds such as acetaldehyde that contain in a large number in drinks.
For the foregoing reasons, even expectation is a kind of for the such spirituosity solution that contains a large amount of inorganic salts of for example brewing wine, also can remove the wherein method of removing the aldehyde compound in spirituosity solution of aldehyde compound.
[patent documentation 1] Japanese Patent Publication 36-12194 communique
[patent documentation 2] TOHKEMY 2005-102554 communique
[patent documentation 3] Japan internationality discloses brochure No. 02/004593
Summary of the invention
Invent problem to be solved
The method the invention provides a kind of method of removing the aldehyde compound in spirituosity solution, even for the brewing wine that for example contains a large amount of inorganic salts, also can be removed aldehyde compound wherein effectively.
The means of dealing with problems
Method of removing the aldehyde compound in spirituosity solution of the present invention is characterized in that, the method passes into primary amine type basic anion exchange resin layer with spirituosity solution.
Method of removing the aldehyde compound in spirituosity solution of the present invention preferably adopts brewing wine or liquor as described spirituosity solution.
In addition, in the present invention, provide a kind of refined brewing wine of aforesaid method that utilizes.
The effect of invention
According to the present invention, provide a kind of method of removing the aldehyde compound in spirituosity solution, even the method also can be removed aldehyde compound wherein effectively for the such spirituosity solution that contains a large amount of inorganic salts of for example brewing wine.
Embodiment
Below, be elaborated for method of removing the aldehyde compound in spirituosity solution of the present invention.
Method of removing the aldehyde compound in spirituosity solution of the present invention is characterized in that, adopts primary amine type basic anion exchange resin layer as its resinbed, and spirituosity solution is passed into this resin layer.
[primary amine type basic anion exchange resin layer]
As everyone knows, primary amine carries out nucleophilic addition(Adn) to aldehyde compound and forms imines; In primary amine type basic anion exchange resin layer of the present invention, utilize this reaction, make aldehyde compound be fixed in resin layer, thereby remove aldehyde compound from the spirituosity solution that passes into this resin layer.As described primary amine type basic anion exchange resin layer (below be sometimes referred to as anion exchange resin layer), there is no particular restriction, but become preferred because the chemical stability of styrenic anion exchange resin layer is high.As the styrenic anion exchange resin layer, can enumerate the structural unit with following formula (1) expression resin layer, have the resin layer of the structural unit of following formula (2) expression, the preferred latter wherein.
[Chemical formula 1]
Figure G2008101734581D00031
[Chemical formula 2]
Figure G2008101734581D00032
(in above-mentioned formula, n, a, b and c represent respectively the polymerization degree.)
[spirituosity solution]
Aldehyde compound of the present invention remove method, pass into the pH value of spirituosity solution in anion exchange resin layer preferred 2～10, more preferably 4～6.
Reaction between primary amine and aldehyde compound comprises: (1) amine carries out nucleophilic addition(Adn), makes the hydrogen atom on nitrogen-atoms in amine shift to Sauerstoffatom on carbonyl the carbonylic carbon atom on aldehyde compound, forms hydroxyl; (2) this hydroxyl occurs protonated under the effect of acid catalyst and sloughs, forms imines.Therefore, favourable to the nucleophilic addition(Adn) of aldehyde compound in (1) when the pH value of the spirituosity solution that passes into, reduces because protonated ratio occurs amine when above 2, so the efficient of removing of aldehyde compound increases.Simultaneously, 10 when following, due to the protonated formation favourable condition of hydroxyl in (2), so the efficient of removing of aldehyde compound increases when the pH value of the spirituosity solution that passes into.
As the spirituosity solution that passes in primary amine type basic anion exchange resin layer of the present invention, preferably adopt brewing wine or liquor.As brewing wine, can enumerate such as japanese wine, beer, grape wine, sweetener wine etc.As liquor, can enumerate such as liquor, whisky, brandy, white wine etc.
In addition, spirituosity solution passes into temperature and is preferably-10～40 ℃.The setting of this temperature depends on ethanol concn, if but make and pass into temperature more than-10 ℃, can eliminate solution freeze and viscosity increases, thereby spirituosity solution and resin layer can be in contact with one another effectively, so can improve the efficient of removing of aldehyde compound.Simultaneously, pass into temperature below 40 ℃ if make, the alcoholic content in spirituosity solution becomes and is difficult for evaporation.In addition, when containing aroma component in spirituosity solution, by passing into Temperature Setting below 40 ℃, can make the evaporation of aroma component and become to be difficult for occuring.
In addition, the speed that passes into of spirituosity solution is preferably SV0.1～50.If make the speed of passing into more than SV0.1, the logical liquid measure of unit time is increased; Simultaneously, if make the speed of passing into below SV50, can make between spirituosity solution and resin layer and can effectively contact, thereby improve the efficient of removing of aldehyde compound.
In addition, pass into the ethanol concn of the spirituosity solution in resin layer preferably below 60%.If make ethanol concn below 60%, anionite-exchange resin is in by the state of hydration, and the contact efficiency between the aldehyde compound of anion exchange resin layer and liquid phase improves, thereby the efficient of removing of aldehyde compound is improved.
In addition, provide in the present invention a kind of brewing wine, this brewing wine is through making with extra care with the above-mentioned method of removing the aldehyde compound in spirituosity solution.
Owing to containing a large amount of inorganic salts in brewing wine, in traditional method, pass in the spirituosity solution after resin layer and will sneak into sulfurous acid, particularly do not remove method for low hydrophobic aldehyde compounds such as acetaldehyde.But, in aldehyde compound of the present invention is removed method, can not sneak into sulfurous acid, and can remove efficiently the aldehyde compound that comprises acetaldehyde.
Adopt method of removing the aldehyde compound in spirituosity solution of the present invention, be in contact with one another by brewing wine being passed into the resin tower that is filled with primary amine type basic anion exchange resin and making both, thereby brewing wine is made with extra care.
Embodiment
Below, the present invention is described in detail to list embodiment and comparative example.But the present invention is not only limited to following record.
Utilize gas chromatographic analysis that the concentration of the aldehyde compound in spirituosity solution is measured.Simultaneously, utilize ion chromatography that the sulfurous acid concentration in spirituosity solution is measured.
[embodiment 1]
Adopt commercially available japanese wine (pure rice wine) as spirituosity solution.The pH value of this japanese wine is 4.5.In addition, the ethanol concn of this japanese wine is 16%, and the aldehyde compound concentration that wherein comprises is 130mg/l.With this japanese wine of 500ml under 20 ℃, (trial target 50ml), carries out the processing of removing of aldehyde compound to pass into the primary amine basic anion exchange resin layer of the structural unit with following formula (2) with the speed of 150ml/ hour (SV3).
[chemical formula 3]
Figure G2008101734581D00051
[comparative example 1]
Except adopting tertiary amine-type alkalescence anion exchange resin layer (Amberlite (registered trademark) IRA96SB, 50ml) beyond the primary amine basic anion exchange resin layer in replacement embodiment 1, utilize the method identical with embodiment 1 to carry out the processing of removing of aldehyde compound.
[comparative example 2]
Except adopting HSO 3Type quaternary amine type basic anion exchange resin layer (Amberlite (registered trademark) IRA404,50ml) beyond the primary amine basic anion exchange resin layer in replacement embodiment 1, utilize the method identical with embodiment 1 to carry out the processing of removing of aldehyde compound.
The evaluation result of the above embodiments 1 and comparative example 1～2 is as shown in table 1.
[table 1]
Ethanol concn (%) Aldehyde compound (mg/l) Sulfurous acid (mg/l)
Stoste 16 130 0
Embodiment 1 16 30 0
Comparative example 1 16 120 0
Comparative example 2 16 <10 >1000
Method at the aldehyde compound in removing spirituosity solution of the present invention is in embodiment 1, and the concentration that passes into the aldehyde compound that contains in the japanese wine after primary amine basic anion exchange resin layer is 30mg/l, has realized efficiently removing aldehyde compound.In addition, by not sneaking into sulfurous acid in the japanese wine after resin layer.
On the other hand, when japanese wine is passed into tertiary amine-type alkalescence anion exchange resin layer (comparative example 1), the aldehyde compound in japanese wine remove inefficiency.
In addition, japanese wine is passed into HSO 3During type quaternary amine type basic anion exchange resin layer (comparative example 2), in the japanese wine after passing into, the concentration of aldehyde compound is extremely low, below 10mg/l.But, sneaked into a large amount of sulfurous acid (more than 1000mg/l) in the japanese wine after passing into.
Industrial applicibility
As mentioned above, in the method for the aldehyde compound in removing spirituosity solution of the present invention, even for the such spirituosity solution of the brewing wine that contains a large amount of inorganic salts, also can remove efficiently aldehyde compound wherein.And, do not sneak into sulfurous acid in spirituosity solution after treatment.Thereby, realized removing aldehyde compound and carry out fragrance and correct from the brewing wine such as the japanese wine that in the past can't remove aldehyde compound, beer, grape wine, sweetener wine.

Claims (2)

1. method of removing the aldehyde compound in spirituosity solution, wherein, the method passes into spirituosity solution on the primary amine type basic anion exchange resin layer with the represented structural unit of following formula (2):
Figure FSB00001028882600011
In above-mentioned formula, a, b and c represent respectively the polymerization degree.
2. method of removing the aldehyde compound in spirituosity solution according to claim 1, wherein, described spirituosity solution is brewing wine or liquor.
CN2008101734581A 2007-11-15 2008-11-14 Method for removing aldehydes compound in alcohol-containing solution and brewed liquor Expired - Fee Related CN101434900B (en)

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WO2015164414A1 (en) * 2014-04-21 2015-10-29 Regents Of The University Of Minnesota Methods of making modified alcohol containing products

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JP6718309B2 (en) * 2016-05-26 2020-07-08 オルガノ株式会社 Method for purifying alcohol-containing liquid and apparatus for purifying alcohol-containing liquid
KR102615355B1 (en) 2023-10-20 2023-12-20 (주)대영에스지 Internal diameter polishing holder
KR102617516B1 (en) 2023-10-20 2023-12-27 (주)대영에스지 External diameter polishing holder

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CN1860216A (en) * 2003-09-29 2006-11-08 奥加诺株式会社 Method of purifying alcoholic liquor and purification apparatus

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Publication number Priority date Publication date Assignee Title
EP1702977A2 (en) * 2000-07-11 2006-09-20 Sapporo Breweries Limited Method of producing malt alcohol beverages
CN1860216A (en) * 2003-09-29 2006-11-08 奥加诺株式会社 Method of purifying alcoholic liquor and purification apparatus

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015164414A1 (en) * 2014-04-21 2015-10-29 Regents Of The University Of Minnesota Methods of making modified alcohol containing products

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