Method for producing dealcoholic beverage, method for producing alcoholic beverage, and method for producing aroma components derived from alcohol-containing beverage

Abstract

Provided is a method for efficiently producing a dealcoholized beverage that has the flavor of an alcohol-containing beverage and has a reduced ethanol concentration. [Solution] A method for producing a dealcoholic beverage includes: step (A) of separating ethanol and aroma components from an alcohol-containing beverage to obtain a mixture containing ethanol and aroma components, and a residual liquid from which ethanol and aroma components have been separated from the alcohol-containing beverage; step (B) of contacting a resin with the mixture containing ethanol and aroma components to allow the resin to adsorb the aroma components; step (C) of removing ethanol from the resin that has adsorbed the aroma components; step (D) of recovering the aroma components from the resin from which the ethanol has been removed in step (C); and step (E) of mixing the residual liquid obtained in step (A) with the aroma components obtained in step (D) to obtain a dealcoholic beverage.

Description

[Technical Field]

[0001] The present invention relates to a method for producing a dealcoholized beverage having a reduced ethanol concentration from an alcohol-containing beverage. The present invention also relates to a method for producing an alcoholic beverage. The present invention further relates to a method for producing aroma components derived from an alcohol-containing beverage. [Background technology]

[0002] In recent years, there has been an increasing demand for alcohol-flavored beverages that are substantially free of alcohol (non-alcoholic beverages), and non-alcoholic beer-flavored beverages, non-alcoholic wine, and the like are now on the market.

[0003] Non-alcoholic beverages are required to have a reduced ethanol concentration but retain the flavor and taste of alcoholic beverages. For example, one method for producing non-alcoholic beer involves steam distilling beer to separate ethanol and aroma components, obtaining a treated liquid with a reduced ethanol concentration, and then adding a distillate containing the separated ethanol and aroma components to the treated liquid. However, since the distillate contains ethanol as well as the aroma components, the addition of the distillate increases the ethanol concentration.

[0004] Patent Document 1 describes a method for producing ethanol-free wine, which includes an aroma component separation step of separating aroma components from wine, an ethanol separation step of separating ethanol from the wine from which the aroma components have been separated in the previous step, and an aroma component addition step of adding the aroma components separated in the aroma component separation step to the wine that has been subjected to the ethanol separation step to impart aroma to the wine.In the method of Patent Document 1, a membrane treatment step is carried out before the aroma component addition step, in which ethanol entrained with the aroma components separated in the aroma component separation step is separated using a membrane such as a reverse osmosis membrane (RO membrane). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-176367 Summary of the Invention [Problem to be solved by the invention]

[0006] In the method of Patent Document 1, ethanol entrained in aroma components is separated from the aroma components using an RO membrane or the like. However, since separating ethanol by RO membrane treatment takes time, there is room for improvement in terms of efficiency. Furthermore, the method of Patent Document 1 also has room for improvement in terms of improving the recovery rate of aroma components.

[0007] The present invention aims to provide a method for efficiently producing a dealcoholized beverage that has the flavor of an alcohol-containing beverage and has a reduced ethanol concentration. Another object of the present invention is to provide a method for efficiently producing aroma components derived from an alcohol-containing beverage that, when mixed with a beverage or the like, can impart the flavor of an alcohol-containing beverage while suppressing an increase in ethanol concentration. [Means for solving the problem]

[0008] As a result of intensive research to solve the above-mentioned problems, the present inventors have found that treating a mixture containing ethanol and aroma components separated from an alcohol-containing beverage with a resin that adsorbs the aroma components enables good separation of the aroma components and ethanol, and enables efficient recovery of the aroma components derived from the alcohol-containing beverage.When the aroma components separated as described above are mixed with the residual liquid obtained after separating ethanol from an alcohol-containing beverage, the flavor of the alcohol-containing beverage can be imparted while suppressing an increase in ethanol concentration, and therefore a dealcoholized beverage having the flavor and reduced ethanol concentration can be produced.

[0009] That is, the present invention relates to the following methods for producing dealcoholized beverages, methods for producing alcoholic beverages, methods for producing aroma components derived from alcohol-containing beverages, etc. [1] A method for producing a dealcoholized beverage, comprising: (A) a step of separating ethanol and aroma components from an alcohol-containing beverage to obtain a mixture containing the ethanol and aroma components, and a residual liquid from which the ethanol and aroma components have been separated from the alcohol-containing beverage; (B) a step of contacting a resin with the mixture containing the ethanol and aroma components to allow the resin to adsorb the aroma components; (C) a step of removing ethanol from the resin that has adsorbed the aroma components; (D) a step of recovering the aroma components from the resin from which the ethanol has been removed in (C); and (E) a step of mixing the residual liquid obtained in (A) with the aroma components obtained in (D) to obtain a dealcoholized beverage. [2] The method for producing a dealcoholized beverage according to [1] above, wherein the alcohol-containing beverage has an ethanol concentration of 0.1 to 60 v / v%. [3] A method for producing a dealcoholized beverage according to [1] or [2] above, wherein the alcohol-containing beverage is a brewed alcoholic beverage and / or a distilled alcoholic beverage made from fruit and / or grains. [4] The method for producing a dealcoholized beverage according to any one of [1] to [3] above, wherein the alcohol-containing beverage is beer, fruit wine, or sake. [5] The method for producing a dealcoholized beverage according to any one of [1] to [4] above, wherein the alcohol-containing beverage is beer. [6] A method for producing a dealcoholized beverage according to any one of [1] to [5] above, wherein the dealcoholized beverage obtained in step (E) has an ethanol concentration of less than 0.005 v / v%. [7] The method for producing a dealcoholic beverage according to any one of [1] to [6] above, wherein the resin is a styrene-based resin. [8] A method for producing a dealcoholic beverage according to any one of [1] to [7] above, wherein in step (C), the resin that has adsorbed the aroma components is washed with water to remove the ethanol. [9] A method for producing a dealcoholic beverage according to any one of [1] to [8] above, wherein in step (D), the aroma components are eluted from the resin using steam to recover the aroma components.

[10] A method for producing an alcoholic beverage using a dealcoholized beverage produced by the production method described in any one of [1] to [9] above, comprising a step of mixing the dealcoholized beverage with ethanol to adjust the ethanol concentration.

[11] A method for producing aroma components derived from an alcohol-containing beverage, comprising: (A) a step of separating ethanol and aroma components from an alcohol-containing beverage to obtain a mixture containing the ethanol and aroma components, and a residual liquid from the alcohol-containing beverage from which the ethanol and aroma components have been separated; (B) a step of contacting a resin with the mixture containing ethanol and aroma components to allow the resin to adsorb the aroma components; (C) a step of removing ethanol from the resin that has adsorbed the aroma components; and (D) a step of recovering the aroma components from the resin from which the ethanol has been removed in (C). [Effects of the Invention]

[0010] According to the present invention, a method for efficiently producing a dealcoholized beverage having the flavor of an alcohol-containing beverage and a reduced ethanol concentration can be provided. Furthermore, according to the present invention, a method for efficiently producing aroma components derived from an alcohol-containing beverage can be provided, which can be mixed with a beverage or the like to impart the flavor of an alcohol-containing beverage while suppressing an increase in ethanol concentration. [Brief explanation of the drawings]

[0011] [Figure 1] FIG. 1 is a process diagram showing an example of a method for producing a dealcoholized beverage of the present invention. [Figure 2] FIG. 2 is a flow chart showing an example of a method for producing aroma components derived from an alcohol-containing beverage according to the present invention. [Figure 3] FIG. 3 is a diagram showing an outline of the flow of a separation test using an RO membrane. DETAILED DESCRIPTION OF THE INVENTION

[0012] The method for producing a dealcoholized beverage of the present invention includes the steps of: (A) separating ethanol and aroma components from an alcohol-containing beverage to obtain a mixture containing the ethanol and aroma components, and a residual liquid from the alcohol-containing beverage in which the ethanol and aroma components have been separated; (B) contacting a resin with the mixture containing the ethanol and aroma components to allow the resin to adsorb the aroma components; (C) removing ethanol from the resin that has adsorbed the aroma components; (D) recovering the aroma components from the resin from which the ethanol has been removed in (C); and (E) mixing the residual liquid obtained in (A) with the aroma components obtained in (D) to obtain a dealcoholized beverage. Fig. 1 is a process diagram showing an example of the method for producing a dealcoholized beverage of the present invention, in which EtOH means ethanol. The method for producing a dealcoholized beverage of the present invention may include steps other than steps (A) to (E) as long as the effects of the present invention are not impaired.

[0013] According to the production method of the present invention, a dealcoholized beverage having a lower ethanol concentration than the alcoholic beverage can be produced using an alcoholic beverage as a raw material. The alcohol-containing beverage of the present invention refers to a beverage containing ethanol, with an ethanol concentration of typically 0.1 v / v% or more, preferably 0.5 v / v% or more, more preferably 1 v / v% or more, and particularly preferably 3 v / v% or more. The ethanol concentration of the alcohol-containing beverage is preferably 60 v / v% or less, more preferably 15 v / v% or less, and even more preferably 10 v / v% or less. The upper and lower limits may be any combination of ranges. In one aspect, the ethanol concentration of the alcohol-containing beverage is preferably 0.1 to 60 v / v%, more preferably 0.1 to 15 v / v%, even more preferably 0.5 to 10 v / v%, even more preferably 1 to 10 v / v%, and particularly preferably 3 to 10 v / v%. Using an alcohol-containing beverage with an ethanol concentration within the above range can more fully exhibit the effects of the present invention described above. The ethanol concentration can be measured by analysis using a gas chromatograph mass spectrometer (GC / MS). The measurement conditions for GC / MS can be those described in the Examples.

[0014] The alcohol-containing beverage is preferably a brewed alcoholic beverage and / or a distilled alcoholic beverage, more preferably a brewed alcoholic beverage. The alcohol-containing beverage is preferably one made from fruit and / or grains. Preferred brewed alcoholic beverages are those made from fruit and / or grains, and examples thereof include beer, beer-like beverages (beer-flavored beverages) such as happoshu (low-malt beer), sake (Japanese sake), Shaoxing wine, and fruit wine. Examples of fruit wines include wine made from fermented grapes; fruit wines made from fermented peaches, strawberries, pears, mandarin oranges, and the like; and cider, with wine made from fermented grapes being preferred. Brewed alcoholic beverages preferably have an ethanol concentration of 0.1 to 15 v / v. Distilled alcoholic beverages include whiskey, brandy, and shochu. More preferred alcohol-containing beverages are beer, fruit wine, and sake, with beer being even more preferred. The method for producing a dealcoholized beverage of the present invention is suitably used as a method for producing dealcoholized beer. The ethanol concentration of beer is preferably 3 to 10 v / v%.

[0015] In step (A), ethanol and aroma components are separated from an alcohol-containing beverage to obtain a mixture containing the ethanol and aroma components, and a residual liquid obtained by separating the ethanol and aroma components from the alcohol-containing beverage. The method for separating ethanol and aroma components from an alcohol-containing beverage is not particularly limited, and distillation such as reduced-pressure steam distillation or vacuum distillation can be used. In one embodiment of the present invention, the alcohol-containing beverage is subjected to reduced-pressure steam distillation or vacuum distillation to separate the ethanol and aroma components from the beverage, thereby obtaining a distillate (condensate) containing ethanol and aroma components and a residual liquid from the alcohol-containing beverage in which the ethanol and aroma components have been separated. Preferably, the separation is carried out by reduced-pressure steam distillation.

[0016] Steam distillation under reduced pressure can lower the boiling point of an alcohol-containing beverage, allowing ethanol and aroma components to be efficiently distilled from the alcohol-containing beverage. A typical steam distillation apparatus or a spinning separator (continuous countercurrent gas-liquid extraction apparatus) equipped with a spinning cone column can be used as the distillation apparatus for reduced pressure steam distillation.

[0017] When the above separation is performed by reduced pressure steam distillation, the alcohol-containing beverage can be supplied to a distillation apparatus and distillation can be performed. The reduced pressure steam distillation can be performed by setting the temperature and pressure (atmospheric pressure) inside the distillation apparatus. The pressure inside the apparatus when performing reduced pressure steam distillation may be lower than atmospheric pressure (0.1 MPa), but is preferably set to 0.02 MPa or less, more preferably 0.013 MPa or less, and even more preferably 0.0123 MPa or less. Furthermore, the pressure is preferably 0.0025 MPa or more, more preferably 0.004 MPa or more, even more preferably 0.006 MPa or more, and particularly preferably 0.0066 MPa or more. In one aspect, the pressure inside the apparatus when performing reduced pressure steam distillation can be set to preferably 0.0025 to 0.02 MPa, more preferably 0.004 to 0.013 MPa, even more preferably 0.006 to 0.013 MPa, and particularly preferably 0.0066 to 0.0123 MPa.

[0018] If the temperature of the alcohol-containing beverage becomes high in step (A), the heat may change the flavor of the residual liquid, which may impair the original flavor of the alcohol-containing beverage. From this perspective, in step (A), the separation is preferably carried out at 60°C or lower, more preferably 50°C or lower, and even more preferably 47°C or lower. Furthermore, from the perspective of efficiently separating ethanol and aroma components from the alcohol-containing beverage, the temperature during separation is preferably 25°C or higher, more preferably 30°C or higher, even more preferably 40°C or higher, and particularly preferably 43°C or higher. In one aspect, the separation is preferably carried out at 25 to 60°C, more preferably 30 to 60°C, even more preferably 40 to 60°C, even more preferably 40 to 50°C, particularly preferably 43 to 50°C, and most preferably 43 to 47°C. For example, when the separation is carried out by reduced pressure steam distillation, the temperature of the steam is preferably 60°C or lower, more preferably 50°C or lower, and even more preferably 47°C or lower. The temperature of the steam is preferably 25°C or higher, more preferably 30°C or higher, even more preferably 40°C or higher, and particularly preferably 43°C or higher. In one aspect, the temperature of the steam when carrying out reduced pressure steam distillation in step (A) is preferably 25 to 60°C, more preferably 30 to 60°C, even more preferably 40 to 60°C, even more preferably 40 to 50°C, particularly preferably 43 to 50°C, and most preferably 43 to 47°C.

[0019] In one embodiment, the pressure and temperature in the apparatus when performing reduced pressure steam distillation are preferably 0.0025 to 0.02 MPa and 25 to 60°C, more preferably 0.004 to 0.013 MPa and 30 to 50°C, still more preferably 0.006 to 0.013 MPa and 40 to 50°C, and particularly preferably 0.0066 to 0.0123 MPa and 43 to 50°C. The time for which reduced pressure steam distillation or reduced pressure distillation is carried out is not particularly limited, and can be set appropriately depending on the ethanol concentration of the residual liquid, etc.

[0020] Step (A) yields a mixture containing ethanol and aroma components separated from the raw alcohol-containing beverage, and a residual liquid in which the ethanol and aroma components have been separated from the alcohol-containing beverage. The mixture is preferably a liquid from the viewpoint of the workability of step (B), which will be described later. For example, when vacuum steam distillation or vacuum distillation is performed, the extracted ethanol and aroma components are condensed by cooling, and a mixture containing ethanol and aroma components is obtained as a distillate. The residual liquid obtained in step (A) has lower concentrations of ethanol and aroma components than the alcohol-containing beverage used. The residual liquid does not necessarily have the ethanol and aroma components contained in the raw alcohol-containing beverage completely separated (removed), and may contain ethanol and / or aroma components.

[0021] The residual liquid obtained by separating ethanol and aroma components from an alcohol-containing beverage can be used as is or, if desired, diluted with water or the like to produce a dealcoholized beverage. From the viewpoint of flavor, it is preferable to use the residual liquid without dilution. The ethanol concentration in the residual liquid obtained by separating ethanol and aroma components from an alcohol-containing beverage in step (A) may be lower than that of the raw alcohol-containing beverage, but is preferably 0.5 v / v% or less, preferably less than 0.5 v / v%, more preferably less than 0.1 v / v%, even more preferably 0.05 v / v% or less, even more preferably 0.01 v / v% or less, particularly preferably less than 0.005 v / v%, and most preferably 0.001 v / v% or less. The ethanol concentration in the residual liquid may be 0.000 v / v% or more. It is preferable to separate ethanol and aroma components from an alcohol-containing beverage so that the ethanol concentration in the residual liquid is within the above range. When vacuum steam distillation or vacuum distillation is used to separate the ethanol and aroma components, it is preferable to carry out the distillation until the ethanol concentration in the residual liquid reaches the above-mentioned concentration.

[0022] In step (B), the resin is brought into contact with the mixture containing ethanol and the aroma components, thereby allowing the resin to adsorb the aroma components. The resin to be used can be one that adsorbs the above-mentioned aromatic components, and it is preferable to use an adsorption resin. Examples of adsorption resins include synthetic adsorption resins such as aromatic resins (e.g., styrene-based resins (styrene-divinylbenzene copolymers, etc.)) and methacrylic acid ester-based resins. A preferred example of a synthetic adsorption resin is a resin having a specific surface area of ​​500 m 2 Examples of suitable adsorption resins include porous styrene-based resins with a specific surface area of ​​1 / g or more. Among these, styrene-based resins are preferred as adsorption resins, and more preferred are porous styrene-based resins with no ion exchange groups, hydrophobic synthetic adsorption resins, and hydrophilic adsorption resins with a small number of ion exchange groups. Examples of such adsorption resins that can be used include Muromac (registered trademark) SAP9121 and SAP9210 (both manufactured by Muromachi Chemical Co., Ltd.).

[0023] Either a batch system or a column system can be used as a treatment method for adsorbing a mixture containing ethanol and aroma components onto a resin. From the viewpoint of workability, the column system is preferred. When adsorption is performed using a column system, for example, the mixture containing ethanol and aroma components can be passed through a column packed with the above-mentioned resin, thereby adsorbing the aroma components onto the resin. When the mixture containing ethanol and aroma components is a liquid, it is preferable to pass the mixture through the resin in an amount preferably 3 to 5 times its volume relative to the resin to adsorb the aroma components. To increase the adsorption rate of the aroma components, the mixture can also be passed through the resin multiple times. In the batch system, the mixture and resin can be placed in a container and stirred to adsorb the aroma components onto the resin.

[0024] In step (C), ethanol is removed from the resin that has adsorbed the aroma components. Ethanol can be removed from the resin by washing the resin with water. In the present invention, it is preferable to wash the resin with water to remove ethanol from the resin. Washing the resin with water allows ethanol to be removed from the resin without eluting the aroma components. Washing with water can be achieved by contacting the resin with the aroma components. When the aroma components are adsorbed using a column method, water can be passed through a column packed with the resin. For example, it is preferable to pass water in an amount, by volume, of preferably 5 times or more, more preferably 10 times or more, and even more preferably 10 to 50 times the volume of the resin. The temperature of the water is preferably 25°C or less, more preferably 20°C or less, for example, 5 to 25°C, and more preferably 5 to 20°C. When the water temperature is within the above range, the recovery rate of the aroma components is further improved. From the viewpoint of more thoroughly removing ethanol, it is preferable to remove as much water used for washing as possible from the resin after washing.

[0025] In step (D), aroma components are recovered from the resin from which ethanol has been removed in step (C). The aroma components can be recovered by eluting them from the resin. In one embodiment of the present invention, the aroma components are preferably recovered by eluting them from the resin using steam. The use of steam is preferred because it provides a good recovery rate of the aroma components and does not increase the ethanol concentration in the resulting aroma components.

[0026] A solution containing the aroma components can be obtained by contacting steam with a resin to elute the aroma components, and then recovering and condensing the steam containing the aroma components. When a column is used, the solution containing the aroma components can be recovered by passing steam through a column packed with the resin and condensing the steam eluted from the column. The steam is preferably saturated steam. From the viewpoint of efficiently eluting the aroma components, the temperature of the steam is preferably 100°C or higher. Furthermore, from the viewpoint of suppressing changes in the aroma components, the temperature of the steam is preferably 140°C or lower, more preferably 130°C or lower. In one embodiment, the temperature of the steam is preferably 100 to 140°C, more preferably 100 to 130°C. The pressure of the steam is preferably 0.1 MPa or higher, more preferably 0.1 to 0.4 MPa, and even more preferably 0.1 to 0.3 MPa, in terms of gauge pressure. In one embodiment, saturated steam having a pressure within the above range is preferably used.

[0027] The solution containing the aroma components and water obtained above can be used as is in step (E), or, if desired, can be concentrated to increase the concentration of the aroma components or diluted before use. The concentration method is not particularly limited, and examples that can be used include a concentration method using a reverse osmosis membrane (RO membrane) and a method based on vacuum distillation.

[0028] The aroma components recovered in step (D) are derived from the alcoholic beverage raw material, and can impart the flavor of the alcoholic beverage by mixing them with a beverage or the like. In the present invention, aroma components substantially free of ethanol can be efficiently obtained by separating the aroma components from ethanol through treatment with the above-mentioned resin. "Substantially free of ethanol" means that the ethanol concentration is less than 0.100 v / v%, preferably 0.05 v / v% or less. Furthermore, using the above-mentioned resin to separate the aroma components from ethanol allows for a high recovery rate of the aroma components.

[0029] In step (E), the aroma components obtained above are mixed with the residual liquid obtained in step (A) to obtain a dealcoholized beverage. The amount of aroma components to be mixed is not particularly limited, and may be all or a portion of the amount recovered in step (D), and can be selected appropriately. Even when the aroma components obtained in step (D) are mixed with the residual liquid, the ethanol concentration hardly increases as a result of the mixing of the aroma components, so a dealcoholized beverage can be produced that has a reduced ethanol concentration and is imparted with the flavor of the alcohol-containing beverage used as the raw material.

[0030] The ethanol concentration of the dealcoholized beverage obtained in step (E) is preferably 0.01 v / v% or less, more preferably 0.005 v / v% or less, and even more preferably less than 0.005 v / v%. According to the production method of the present invention, a dealcoholized beverage having an ethanol concentration reduced to the above range can be produced. A dealcoholized beverage can also be called a low-alcohol beverage.

[0031] According to the present invention, a dealcoholized beverage can be obtained that contains the flavor components of the alcohol-containing beverage that is the raw material and has a reduced ethanol concentration. The dealcoholized beverage obtained by the present invention is a beverage blended with the residual liquid obtained by separating ethanol from an alcoholic beverage as a raw material and reducing the ethanol concentration to preferably less than 0.005 v / v%, and further contains aroma components contained in the raw material, allowing the flavor of the alcoholic beverage before ethanol separation to be retained. The method for producing a dealcoholized beverage of the present invention is particularly suitable for use in beer, fruit wine, and sake, and is particularly suitable for reducing the ethanol content of beer. In a preferred embodiment of the present invention, when beer is used as a raw material, a dealcoholized beer can be produced that has the original flavor of beer and has an ethanol concentration of less than 0.005 v / v%.

[0032] Examples of aroma components contained in alcohol-containing beverages include, for example, acetaldehyde, ethyl acetate, i-butanol, isoamyl acetate, isoamyl alcohol, etc. In one embodiment of the present invention, it is possible to produce from beer a dealcoholized beer in which the content of one or more compounds selected from the group consisting of acetaldehyde, ethyl acetate, i-butanol, isoamyl acetate, and isoamyl alcohol is preferably 50% or more, more preferably 70% or more, relative to the content in the beer used as a raw material (100%).

[0033] The dealcoholized beverage obtained by the production method of the present invention can be suitably consumed as a beverage as is. Furthermore, an alcoholic beverage (alcohol-containing beverage) with a desired ethanol concentration can be produced by mixing the dealcoholized beverage obtained by the production method of the present invention with ethanol to adjust the ethanol concentration. A method for producing an alcoholic beverage, which includes a step of adjusting the ethanol concentration by mixing the dealcoholized beverage produced by the production method of the present invention described above with ethanol, also constitutes one aspect of the present invention. Any alcohol-containing beverage containing ethanol can be used to add ethanol.

[0034] The present invention also includes a method for producing aroma components derived from alcohol-containing beverages (hereinafter simply referred to as a method for producing aroma components). The method for producing aroma components derived from alcohol-containing beverages of the present invention comprises the steps of: (A) separating ethanol and aroma components from an alcohol-containing beverage to obtain a mixture containing the ethanol and aroma components, and a residual liquid from the alcohol-containing beverage in which the ethanol and aroma components have been separated; (B) contacting a resin with the mixture containing the ethanol and aroma components to allow the resin to adsorb the aroma components; (C) removing ethanol from the resin that has adsorbed the aroma components; and (D) recovering the aroma components from the resin from which the ethanol has been removed in step (C). FIG. 2 is a process diagram showing an example of a method for producing aroma components derived from an alcohol-containing beverage of the present invention. Steps (A) to (D) and preferred embodiments thereof in the method for producing aroma components of the present invention are the same as steps (A) to (D) and preferred embodiments thereof in the method for producing a dealcoholized beverage of the present invention described above. The method for producing aroma components of the present invention may include steps other than steps (A) to (D) as long as the effects of the present invention are not impaired. The aroma components obtained by the production method of the present invention and preferred embodiments thereof are the same as the aroma components obtained by the above-mentioned method for producing a dealcoholized beverage and preferred embodiments thereof. The aroma components obtained by the production method of the present invention are aroma components derived from the alcohol-containing beverage used as a raw material, and can impart the flavor and taste of the alcohol-containing beverage by mixing them with a beverage or the like.

[0035] The alcohol-containing beverage and its preferred embodiments used in the aroma component production method of the present invention are the same as the alcohol-containing beverage and its preferred embodiments used in the above-mentioned dealcoholized beverage production method. For example, when beer is used as the alcohol-containing beverage, an aroma component (which can also be called an aroma component composition) containing one or more compounds selected from the group consisting of acetaldehyde, ethyl acetate, i-butanol, isoamyl acetate, and isoamyl alcohol can be obtained. [Example]

[0036] EXAMPLES The present invention will be described in more detail below with reference to examples, although the present invention is not limited to these examples. In the following examples, Alc (%) means the ethanol content (concentration) (v / v%). The ethanol content was measured by the following method.

[0037] <Method for measuring ethanol content> The ethanol content of samples such as dealcoholized samples and distillates (condensates) obtained from alcoholic beverages was measured using GC / MS (product name: 6890 series GC system, 5973 Network Mass Selective Detector, Agilent). The samples were analyzed without pretreatment, with the addition of an internal standard (acetone). The GC / MS measurement conditions were as follows. A calibration curve was prepared according to the ethanol concentration of the sample, and quantification was performed. For example, when measuring a 0.005% sample, a calibration curve was prepared with five points (at least three points) between 0.001 and 0.01%.

[0038] Column: GL Science Inter Cap PureWAX+TL (length: 60 m, inner diameter: 250 μm, membrane thickness: 0.25 μm) Gas flow rate: 2.8 mL / min, average linear velocity: 43 cm / sec Temperature increase: 50°C (15 minutes) → 240°C (heat increase at 120°C / min) → 250°C (5 minutes) Injection: 0.2 μL Split ratio 50:1 Number of measurements: n=2 (prepared two samples)

[0039] <Measuring method for low boiling point compounds (LVC: Low Volatile Compounds)> LVC analysis was performed using GC (product name: GC2010, manufactured by Shimadzu Corporation) under the following measurement conditions. GC conditions Column: DB-WAX (inner diameter 0.53 mm, length 30 m, membrane thickness 1 μm) (Agilent Technologies, Inc.) Gas flow rate: Helium 25 Psi, Hydrogen 47 mL / min, Air 400 mL / min Temperature increase: 40°C (5 min) → 140°C (heat increase at 40°C / min) → 140°C (1 min) Detector: FID Detector temperature: 200℃ Sampling rate: 40msec End time: 11 minutes Headspace sampler conditions Temperature: Needle (180℃), Transfer (180℃), Oven (40℃) Timing: Pressurization (10 min), Injection (0.08 min), Withdrawal (0.2 min), Oven (36 min), PII (18 min), Cycle Time (18 min) Carrier: 25 Psi Injection method: Full injection As LVC, the contents of acetaldehyde, ethyl acetate, i-butanol, isoamyl acetate, and isoamyl alcohol, which are typical aroma components produced by fermentation, were measured.

[0040] <Reference example 1> Dealcoholization using reduced pressure steam distillation 1. Raw materials and equipment The raw materials used were commercially available beer (Alc 5.5%, hereafter referred to as Beer A) and commercially available non-alcoholic beer (non-alcoholic beer made in a foreign country (other than Japan), Alc 0.5%, hereafter referred to as Non-alcoholic Beer B). Vacuum steam distillation was carried out using a continuous countercurrent gas-liquid extraction apparatus.

[0041] 2. Examination of steam distillation conditions The raw material was supplied to the above-mentioned apparatus and subjected to reduced pressure steam distillation, and the ethanol concentration of the residual liquid after distillation (de-alcoholized sample) was measured. When dealcoholization is performed by steam distillation, it was known that the amount of steam relative to the amount of alcohol-containing beverage is an important parameter. Therefore, the number of treatments, raw material feed flow rate, and steam temperature, which can change the amount of steam relative to the amount of beer, were set as parameters, and the relationship between each parameter and dealcoholization was examined.

[0042] 2.1 Effect of treatment times on dealcoholization The effect of varying the reduced pressure steam distillation treatment time was investigated by changing the number of times of reduced pressure steam distillation treatment. When multiple treatments were performed, after the first treatment, the reduced pressure was released only at the bottom of the column, and the recovered dealcoholized sample was applied again to the top of the column. The conditions for reduced-pressure steam distillation are shown in Condition 1 below. The column wall temperature and column bottom temperature were set higher than the steam temperature because steam would condense on the column wall and bottom if the treatments were performed at the same temperature. The reduced-pressure steam distillation treatment time can also be changed by changing the column length.

[0043] <Condition 1> Ingredients: Beer A Total raw material feed volume: 300mL Raw material feed flow rate: 30 mL / min Column wall temperature: 45℃ Column bottom temperature: 50°C Temperature inside the steam generating flask: 50℃ Steam temperature: 40℃ Column pressure (absolute pressure): 0.0066 MPa

[0044] The ethanol concentration in the dealcoholized sample when the number of treatments was changed is shown in Table 1. The reduced pressure steam distillation treatment time was 10 minutes per treatment. After three treatments, the ethanol concentration was 0.001 v / v%.

[0045] [Table 1]

[0046] 2.2 Effect of steam temperature on dealcoholization The effect of steam temperature on the ethanol concentration of dealcoholized samples was examined. Increasing the steam temperature increases the steam density, making it possible to change the amount of steam relative to the amount of beer. The conditions for reduced pressure steam distillation are shown in Condition 2 below. The number of treatments was one. Table 2 shows the ethanol concentration in dealcoholized samples when the steam temperature was changed.

[0047] <Condition 2> Ingredients: Beer A Total raw material feed volume: 300mL Raw material feed flow rate: 30 mL / min Column wall temperature: 45°C, 55°C, or 65°C (set according to steam temperature) Column bottom temperature: 55°C or 65°C (set according to the steam temperature) Temperature inside the steam generating flask: 50℃, 60℃ or 70℃ (set according to the steam temperature) Steam temperature: 40℃, 50℃ or 60℃ Column pressure (absolute pressure): 0.0066 MPa, 0.0123 MPa, or 0.0199 MPa (set according to steam temperature)

[0048] [Table 2]

[0049] 2.3 Effect of feed amount and alcohol content of raw material on dealcoholization The effect of the ethanol concentration in the raw material on the ethanol concentration in the sample after dealcoholization was investigated. The reduced pressure steam distillation conditions are shown in Condition 3 below. The treatment was performed once. The results are shown in Table 3.

[0050] <Condition 3> Ingredients: Beer A (Alc 5.5%), Non-alcoholic Beer B (Alc 0.5%) Total raw material feed volume: 300mL Raw material feed flow rate: 30 mL / min, 20 mL / min or 10 mL / min Column wall temperature: 45℃ Column bottom temperature: 50°C Temperature inside the steam generating flask: 50℃ Steam temperature: 44℃ Column pressure (absolute pressure): 0.0066 MPa

[0051] [Table 3]

[0052] Example 1 Study on separation technology of alcohol and aroma in distillate Beer A was distilled under reduced pressure (using an evaporator) to obtain a beer distillate (ethanol concentration 12 v / v%) containing ethanol and aroma components. The conditions for the reduced pressure distillation were as follows. Beer A was the same as that used in Reference Example 1. Temperature: 30℃ Absolute pressure: 0.0027MPa Concentration: Distill under reduced pressure until 500 mL of beer A becomes 300 mL (Continue until 200mL of distillate can be obtained from 500mL of beer A)

[0053] A method for separating aroma compounds and ethanol using adsorption resins was investigated. Muromac® SAP9121 and SAP9210 (both manufactured by Muromachi Chemical Co., Ltd.) were used to recover aroma compounds from distillates using adsorption resins. These are styrene-based resins. The adsorption principle of these resins is to apply van der Waals forces to adsorb and desorb compounds, and it is possible to desorb compounds by applying energy greater than the van der Waals forces acting between the resin and the compounds.

[0054] The resin was swollen and washed before use, just like a standard resin. To adsorb the aroma components, 400 mL of resin was packed into a column, and 1,450 mL of the beer distillate obtained above was passed through it. This process was repeated five times to maximize the aroma adsorption rate. Subsequently, 4,000 mL of purified water (20°C) was passed through the column to remove any remaining ethanol. After washing, the column was drained as much of the remaining pure water as possible, and the aroma components were then recovered using steam. Steam was passed through the column to elute the aroma components from the resin. Aroma component recovery was performed using steam above 100°C at a steam pressure of 0.2 MPa (gauge pressure). The steam was condensed using a condenser installed at the column outlet and collected as an aroma solution. Fractions of 500 mL were collected, for a total of 8 L of aroma solution. The ethanol concentrations of fractions 1–16 were measured.

[0055] The ethanol concentrations of fractions 1 to 16 when Muromac (registered trademark) SAP9121 was used are shown in Table 4. The ethanol concentration was 0.002 v / v% or less from fraction 2 onwards. When Muromac (registered trademark) SAP9120 was used, the ethanol concentration was also 0.002 v / v% or less from fraction 2 onwards.

[0056] [Table 4]

[0057] The aroma solution (a mixed solution of fractions 1 to 16) was analyzed for low boiling point compounds (LVC) content to determine the recovery rate (%) from the raw material. This recovery rate is the ratio (%) of the amount of LVC contained in the aroma solution to the amount of LVC contained in the raw material, taken as 100%. The recovery rate was higher when Muromac (registered trademark) SAP9121 was used than when SAP9120 was used. The recovery rates of aroma components when Muromac (registered trademark) SAP9121 was used are shown in Table 5.

[0058] <Comparative Example 1> The beer distillate produced in Example 1 was used to separate ethanol using an RO membrane. The equipment was a flat membrane device manufactured by Alfa Laval, and the RO membrane was a GE FLAT SHEET AG (12 x 12) manufactured by GE Healthcare (effective filtration area per sheet: 0.018125 m). 2 ) was used. Figure 3 shows an outline of the flow of the separation test using an RO membrane. The RO membrane used selectively allows ethanol and water to permeate, and the permeate that passes through the RO membrane contains ethanol and water, as well as some aroma components. The separation conditions using RO membranes were as follows: Water was first added to the beer distillate to increase the volume, and the recovery rate and other factors were evaluated based on the results of analyzing the sample after adding water. Beer distillate: 2647mL (add water to make 18900g) Ethanol concentration: 12v / v% before water addition, 1.34v / v% after water addition Flow rate: 5mL / min Gauge pressure inside the device: 2.4 to 3.0 MPa

[0059] Because RO membrane separation requires a long period of time, the test was conducted while cooling the device inlet with 2°C cold water and ice-cooling the circulating liquid. As the separation progressed, the circulating liquid decreased in volume, so water was added as needed. Separation continued for 8.6 hours until the ethanol content of the circulating liquid reached 0 v / v%. When the ethanol content of the circulating liquid reached 0 v / v%, water addition was stopped, and the liquid was concentrated as much as possible to recover as much circulating liquid as possible. Regarding the amount of ethanol in the circulating liquid, samples were measured by GC / MS after the experiment was completed. However, since GC / MS measurements were not possible during the test, measurements were performed using an Anton Paar density meter. The content of low-boiling-point compounds in the recovered circulating liquid was analyzed, and the recovery rate (%) from the raw material was calculated. The results are shown in Table 5.

[0060] [Table 5]

[0061] The low-boiling compounds listed in Table 5 are typical aroma components produced by fermentation. When aroma components and ethanol were separated using resin, the recovery rate of aroma components was higher than that using RO membrane separation. Furthermore, when using resin, aroma components and ethanol could be separated in a shorter time than when using RO membrane.

[0062] <Example 2> The recovered aroma components were added to the dealcoholized sample to confirm the flavor-imparting effect. Beer A used was the same as that used in Reference Example 1. A dealcoholized beer sample was prepared by reduced pressure steam distillation from beer A. The reduced pressure steam distillation was carried out under the following conditions using the same apparatus as in Reference Example 1. The ethanol concentration of the resulting dealcoholized beer sample (hereinafter referred to as dealcoholized sample (I)) was 0.001 v / v%. (Conditions for reduced pressure steam distillation) Raw material feed flow rate: 30 mL / min Steam temperature: 45℃ Column pressure (absolute pressure): 0.0066 MPa Number of treatments: 2 times under the above conditions

[0063] The aroma components of the distillate (Alc 11.06%) obtained by vacuum steam distillation of Beer A were adsorbed onto an adsorption resin (Muromac (registered trademark) SAP9121, Muromachi Chemical Co., Ltd.) in the same manner as in Example 1. The resin was then washed with water, and the aroma components were eluted with steam to obtain an aroma solution (Alc 0.02 v / v%). The resulting aroma solution was concentrated to produce a concentrated aroma solution (Alc 0.048%). 45 mL of the concentrated aroma solution was mixed with 400 mL of the dealcoholized sample (I) obtained above to obtain dealcoholized beer (II) with an ethanol concentration of 0.0048 v / v%. (evaluation) To confirm whether the addition of recovered aromas can impart a brewing-derived aroma, a comparison was made between dealcoholized sample (I) and dealcoholized beer (II). A sensory evaluation was conducted by four trained panelists (Panelists A-D). The evaluation criteria were beer-like brewing aroma (the beer-like aroma that arises during brewing), wort odor, and stale flavor. Each sample was sipped and rated on a 13-point scale (0-3, in 0.25-point increments) using the following criteria. The panelists then calculated the average of their scores. In non-alcoholic beer, wort odor is perceived as a negative trait. Therefore, a weaker wort odor indicates a better flavor. Stale flavor is a negative flavor that occurs due to heating, such as a cooked odor or sourness. When components deteriorate due to the thermal load of vacuum distillation, stale flavor becomes stronger.

[0064] (Beer-like brewing aroma) 0: Strong beer-like brewing aroma 1: A beer-like brewing aroma 2: A slight beer-like brewing aroma 3: I don't sense the typical beer aroma.

[0065] (wort smell) 0: No wort smell 1: Slight wort smell 2: I smell wort 3: Strong wort smell

[0066] (degraded flavor) 0: No deterioration flavor 1: Slightly deteriorated flavor 2: I sense a stale flavor 3: Strongly perceived deterioration flavor

[0067] The scores of each panelist and the average scores are shown in Tables 6 to 8. Table 6 shows the evaluation results for the beer-like brewed aroma, Table 7 shows the evaluation results for the wort smell, and Table 8 shows the evaluation results for the aged aroma.

[0068] [Table 6]

[0069] [Table 7]

[0070] [Table 8]

[0071] The above results demonstrate that separating ethanol and aroma components from beer and adding the ethanol-removed aroma components to a dealcoholized beer sample can impart a beer-like brewing aroma. Furthermore, while simply separating ethanol from beer leaves behind noticeable wort odors and stale flavors, these flavors can be reduced. Removing ethanol from beer reduces the beer-like flavor because the brewing-derived aroma disappears. However, removing ethanol from the recovered aroma components and adding it back to the beer resulted in the production of a dealcoholized beer with a beer-like flavor and reduced ethanol concentration.

Claims

1. Step (A): Separating ethanol and one or more aromatic components selected from the group consisting of acetaldehyde, ethyl acetate, i-butanol, isoamyl acetate, and isoamyl alcohol from an alcohol-containing beverage, thereby obtaining a mixture containing the ethanol and aromatic components, and the residual liquid from which the ethanol and aromatic components have been separated from the alcohol-containing beverage; (C) A step of removing ethanol from the mixture containing the ethanol and aroma components; Step (D) for recovering the aroma components from which ethanol has been removed in step (C); and The process includes step (E) of mixing the residual liquid obtained in step (A) with the aroma component obtained in step (D) to obtain a de-alcoholized beverage having an ethanol concentration of less than 0.005 v / v%, A method for producing non-alcoholic beverages.

2. The method for producing a de-alcoholic beverage according to claim 1, wherein the alcohol-containing beverage has an ethanol concentration of 0.1 to 60 v / v%.

3. The method for producing a de-alcoholic beverage according to claim 1 or 2, wherein the alcohol-containing beverage is a brewed and / or distilled alcoholic beverage made from fruits and / or grains.

4. The method for producing a de-alcoholic beverage according to any one of claims 1 to 3, wherein the alcohol-containing beverage is beer, fruit wine, or sake.

5. The method for producing a de-alcoholic beverage according to any one of claims 1 to 4, wherein the alcohol-containing beverage is beer.

6. The method for producing a de-alcoholized beverage according to claim 1, wherein in step (C), a resin is brought into contact with a mixture containing the ethanol and the aroma component to adsorb the aroma component onto the resin, and the ethanol is removed from the resin that has adsorbed the aroma component.

7. The method for producing a de-alcoholized beverage according to claim 6, wherein the resin is a styrene-based resin.

8. The method for producing a de-alcoholic beverage according to claim 6 or 7, wherein in step (C), the resin on which the aroma component has been adsorbed is washed with water to remove ethanol.

9. A dealcoholized beer-flavored beverage containing acetaldehyde, ethyl acetate, i-butanol, isoamyl acetate, and isoamyl alcohol, with an ethanol concentration of less than 0.005 v / v%.

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