Method of producing dealcoholization drink, method of producing alcoholic drink, and method of producing aroma constituent derived from alcohol-containing drink

Abstract

To provide a method of efficiently producing a dealcoholization drink having flavor of an alcohol-containing drink and reduced in an ethanol concentration, and a method of efficiently producing an aroma constituent derived from an alcohol-containing drink capable of applying flavor of an alcohol-containing drink by mixing to a drink or the like while suppressing increase of an ethanol concentration.SOLUTION: A method of producing a dealcoholization drink includes: a process of separating ethanol and an aroma constituent from an alcohol-containing drink to obtain a mixture containing ethanol and an aroma constituent, and a residual liquid obtained by separating ethanol and an aroma constituent from the alcohol-containing drink; a process of contacting a resin with the mixture containing ethanol and the aroma constituent to adsorb the aroma constituent to the resin; a process of removing ethanol from the resin absorbed with the aroma constituent; a process of recovering the aroma constituent from the resin from which ethanol is removed; and a process of mixing the residual liquid with the aroma constituent to obtain the dealcoholization drink.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a method for producing a dealcoholized beverage with 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 Art

[0002] In recent years, the demand for beverages with an alcohol taste that are substantially alcohol-free (non-alcoholic beverages) has been increasing, and non-alcoholic beer-taste beverages, non-alcoholic wines, etc. are being sold as non-alcoholic beverages.

[0003] For non-alcoholic beverages, it is required that only the ethanol concentration is reduced and they have the aroma of alcoholic beverages. For example, as a method for producing non-alcoholic beer, there is a method in which beer is steam-distilled to separate ethanol and aroma components to obtain a treatment liquid with a reduced ethanol concentration, and a distillate containing the separated ethanol and aroma components is added to the treatment liquid. However, since the distillate contains ethanol together with the aroma components, the ethanol concentration increases due to the addition of the distillate.

[0004] Patent Document 1 describes a method for producing dealcoholized wine including 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 above step, and an aroma component addition step of adding the aroma components separated in the aroma component separation step to the wine that has undergone the ethanol separation step to impart aroma to the wine. In the method of Patent Document 1, before the aroma component addition step, a membrane treatment step is performed in which ethanol accompanying the aroma components separated in the aroma component separation step is separated by a membrane such as a reverse osmosis membrane (RO membrane).

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] In the method of Patent Document 1, ethanol accompanying the fragrance component is separated from the fragrance component using an RO membrane or the like. However, since it takes time to separate ethanol by RO membrane treatment, there is room for improvement in terms of efficiency. Further, there is room for improvement in the method of Patent Document 1 to improve the recovery rate of aroma components.

[0007] An object of the present invention is to provide a method capable of efficiently producing a de-alcoholized beverage having the flavor of an alcoholic beverage and having a reduced ethanol concentration. Another object of the present invention is to provide a method capable of efficiently producing an aroma component derived from an alcoholic beverage that can impart the flavor of an alcoholic beverage while suppressing an increase in ethanol concentration when mixed with a beverage or the like.

Means for Solving the Problems

[0008] As a result of intensive studies to solve the above problems, the present inventor has found that when a mixture containing ethanol and an aroma component separated from an alcoholic beverage is treated with a resin that adsorbs the aroma component, the aroma component and ethanol can be well separated, and the aroma component derived from an alcoholic beverage can be efficiently obtained with a high recovery rate. When the aroma component separated as described above is mixed with the residual liquid from which ethanol has been separated from the alcoholic beverage, it is possible to impart the flavor of the alcoholic beverage while suppressing an increase in ethanol concentration, and thus it is possible to produce a de-alcoholized beverage having the flavor and having a reduced ethanol concentration.

[0009] That is, the present invention relates to the following methods for producing a de-alcoholized beverage, a method for producing an alcoholic beverage, a method for producing an aroma component derived from an alcoholic beverage, and the like. (1) A process (A) of separating ethanol and aroma components from an alcoholic 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 alcoholic beverage; a process (B) of bringing a resin into contact with the mixture containing the ethanol and aroma components to adsorb the aroma components onto the resin; a process (C) of removing ethanol from the resin adsorbed with the aroma components; a process (D) of recovering the aroma components from the resin from which ethanol has been removed in the process (C); and a process (E) of mixing the residual liquid obtained in the process (A) and the aroma components obtained in the process (D) to obtain a non-alcoholic beverage, the method for producing a non-alcoholic beverage comprising these processes. (2) The method for producing a non-alcoholic beverage according to (1) above, wherein the alcoholic beverage has an ethanol concentration of 0.1 to 60 v / v%. (3) The method for producing a non-alcoholic beverage according to (1) or (2) above, wherein the alcoholic beverage is a fermented liquor and / or a distilled liquor made from fruits and / or grains as raw materials. (4) The method for producing a non-alcoholic beverage according to any one of (1) to (3) above, wherein the alcoholic beverage is beer, fruit wine or sake. (5) The method for producing a non-alcoholic beverage according to any one of (1) to (4) above, wherein the alcoholic beverage is beer. (6) The method for producing a non-alcoholic beverage according to any one of (1) to (5) above, wherein the ethanol concentration of the non-alcoholic beverage obtained in the process (E) is less than 0.005 v / v%. (7) The method for producing a non-alcoholic beverage according to any one of (1) to (6) above, wherein the resin is a styrene-based resin. (8) The method for producing a non-alcoholic beverage according to any one of (1) to (7) above, wherein in the process (C), the resin adsorbed with the aroma components is washed with water to remove ethanol. (9) The method for producing a non-alcoholic beverage according to any one of (1) to (8) above, wherein in the process (D), the aroma components are eluted from the resin with steam to recover the aroma components. 〔10〕A method for producing an alcoholic beverage using a de-alcoholized beverage produced by the production method according to any one of 〔1〕 to 〔9〕 above, the method comprising a step of mixing the de-alcoholized beverage and ethanol to adjust the ethanol concentration. 〔11〕A process (A) of separating ethanol and aroma components from an alcoholic 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 alcoholic beverage; a step (B) of bringing a resin into contact with the mixture containing the ethanol and aroma components to adsorb the aroma components onto the resin; a step (C) of removing ethanol from the resin adsorbed with the aroma components; and a step (D) of recovering the aroma components from the resin from which ethanol has been removed in the step (C). A method for producing aroma components derived from an alcoholic beverage.

Advantages of the Invention

[0010] According to the present invention, it is possible to provide a method capable of efficiently producing a de-alcoholized beverage having the flavor of an alcoholic beverage and a reduced ethanol concentration. Further, according to the present invention, it is possible to provide a method capable of efficiently producing aroma components derived from an alcoholic beverage, which can impart the flavor of an alcoholic beverage while suppressing an increase in ethanol concentration when mixed with a beverage or the like.

Brief Description of the Drawings

[0011]

Figure 1

Figure 2

Figure 3

Modes for Carrying Out the Invention

[0012] The method for producing a de-alcoholized beverage of the present invention comprises the steps 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 (step A); contacting a resin with the mixture containing the ethanol and aroma components to adsorb the aroma components onto the resin (step B); removing ethanol from the resin adsorbed with the aroma components (step C); recovering the aroma components from the resin from which ethanol has been removed in step (C) (step D); and mixing the residual liquid obtained in step (A) with the aroma components obtained in step (D) to obtain a de-alcoholized beverage (step E). Figure 1 is a process diagram showing an example of the method for producing a de-alcoholized beverage of the present invention. In the figure, EtOH means ethanol. The method for producing a de-alcoholized 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] In the production method of the present invention, a de-alcoholized beverage with a reduced ethanol concentration compared to the alcohol-containing beverage can be produced using the alcohol-containing beverage as a raw material. The alcohol-containing beverage in the present invention is a beverage containing ethanol, and usually has an ethanol concentration of 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 in any combination. In one aspect, the alcohol-containing beverage preferably has an ethanol concentration of 0.1 to 60 v / v%, more preferably 0.1 to 15 v / v%, even more preferably 0.5 to 10 v / v%, still more preferably 1 to 10 v / v%, and particularly preferably 3 to 10 v / v%. When an alcohol-containing beverage with an ethanol concentration within the above range is used, the effects of the present invention described above can be more fully exhibited. The measurement of ethanol concentration can be carried out by analysis using a gas chromatograph mass spectrometer (GC / MS). As the measurement conditions of GC / MS, the conditions described in the examples can be adopted.

[0014] The alcoholic beverage is preferably a brewed liquor and / or a distilled liquor, more preferably a brewed liquor. The alcoholic beverage is preferably made from fruits and / or grains. As the brewed liquor, a brewed liquor made from fruits and / or grains is preferred, and examples include beer-based beverages such as beer and sparkling wine (beer-taste beverages), sake (Japanese rice wine), Shaoxing wine, fruit wine, etc. As the fruit wine, for example, wine fermented from grapes; fruit wine fermented from peaches, strawberries, pears, oranges, etc.; cider, etc. are mentioned, and preferably wine fermented from grapes. The brewed liquor preferably has an ethanol concentration of 0.1 to 15 v / v. As the distilled liquor, whiskey, brandy, shochu, etc. are mentioned. As the alcoholic beverage, beer, fruit wine, and sake are more preferred, and beer is even more preferred. The method for producing the dealcoholized beverage of the present invention is preferably used as a method for producing dealcoholized beer. Beer preferably has an ethanol concentration of 3 to 10 v / v%.

[0015] In step (A), ethanol and aroma components are separated from the alcoholic beverage to obtain a mixture containing the above ethanol and aroma components and a residual liquid from which ethanol and aroma components have been separated from the above alcoholic beverage. The method for separating ethanol and aroma components from the alcoholic beverage is not particularly limited, and for example, distillation such as vacuum steam distillation and vacuum distillation can be used. In one aspect of the present invention, by subjecting the alcoholic beverage to vacuum steam distillation or vacuum distillation, ethanol and aroma components are separated from the beverage to obtain a distillate (condensate) containing ethanol and aroma components and a residual liquid from which ethanol and aroma components have been separated from the alcoholic beverage. Preferably, the above separation is carried out by vacuum steam distillation.

[0016] When performing steam distillation under reduced pressure, the boiling point of the alcoholic beverage can be lowered, so that ethanol and aroma components can be efficiently distilled from the alcoholic beverage. As a distillation apparatus for performing reduced-pressure steam distillation, a general steam distillation apparatus, a spinning separator equipped with a spinning cone column (continuous countercurrent gas-liquid extraction apparatus), or the like can be used.

[0017] When performing the above separation by reduced-pressure steam distillation, the alcoholic beverage can be supplied to the distillation apparatus and distilled. 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 the atmospheric pressure (0.1 MPa), but is preferably set to 0.02 MPa or less, more preferably 0.013 MPa or less, and still more preferably 0.0123 MPa or less. Further, the above pressure is preferably 0.0025 MPa or more, more preferably 0.004 MPa or more, still 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 preferably set to 0.0025 to 0.02 MPa, more preferably 0.004 to 0.013 MPa, still more preferably 0.006 to 0.013 MPa, and particularly preferably 0.0066 to 0.0123 MPa.

[0018] In step (A), when the alcoholic beverage is heated to a high temperature, the heat may change the flavor of the residual liquid, which may impair the original flavor of the alcoholic beverage. From this perspective, in step (A), it is preferably carried out at 60°C or lower, more preferably 50°C or lower, and even more preferably 47°C or lower. Also, from the perspective of efficiently separating ethanol and aroma components from the alcoholic 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 embodiment, it is preferably carried out at 25 - 60°C, more preferably 30 - 60°C, even more preferably 40 - 60°C, even more preferably 40 - 50°C, particularly preferably 43 - 50°C, and most preferably 43 - 47°C. For example, when performing the above separation by vacuum steam distillation, it is preferably that the temperature of the steam is 60°C or lower, more preferably 50°C or lower, and even more preferably 47°C or lower. Also, 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 embodiment, when performing vacuum steam distillation in step (A), the temperature of the steam is preferably 25 - 60°C, more preferably 30 - 60°C, even more preferably 40 - 60°C, even more preferably 40 - 50°C, particularly preferably 43 - 50°C, and most preferably 43 - 47°C.

[0019] In one embodiment, as the pressure and temperature in the apparatus when performing vacuum steam distillation, it is preferably that the pressure is 0.0025 - 0.02 MPa and the temperature is 25 - 60°C, more preferably that the pressure is 0.004 - 0.013 MPa and the temperature is 30 - 50°C, even more preferably that the pressure is 0.006 - 0.013 MPa and the temperature is 40 - 50°C, and particularly preferably that the pressure is 0.0066 - 0.0123 MPa and the temperature is 43 - 50°C. The time for performing vacuum steam distillation or vacuum distillation is not particularly limited and can be appropriately set according to the ethanol concentration of the residual liquid, etc.

[0020] In step (A), a mixture containing ethanol and aroma components separated from an alcohol-containing beverage as a raw material and a residual liquid from which the ethanol and aroma components have been separated from the alcohol-containing beverage are obtained. From the viewpoint of the workability of step (B) described later, the mixture is preferably a liquid. For example, when performing vacuum steam distillation or vacuum distillation, 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 a lower concentration of ethanol and aroma components than the alcohol-containing beverage used. The residual liquid does not necessarily need to have the ethanol and aroma components completely separated (removed) from the raw material alcohol-containing beverage 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 it is or, if desired, diluted with water or the like for the production of 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 the alcohol-containing beverage obtained in step (A) may be lower than that of the raw material 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%, still 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 the alcohol-containing beverage so that the ethanol concentration in the residual liquid falls within the above range. When performing vacuum steam distillation or vacuum distillation for the separation of ethanol and aroma components, it is preferable to perform the distillation until the ethanol concentration in the residual liquid reaches the above concentration.

[0022] In step (B), a resin is brought into contact with the mixture containing the ethanol and aroma components to adsorb the aroma components onto the resin. As the resin, one that adsorbs the above aroma components can be used, and it is preferable to use an adsorption resin. Examples of the adsorption resin include synthetic adsorption resins such as aromatic resins (e.g., styrene resins (such as styrene-divinylbenzene copolymerization)), methacrylic acid ester resins, etc. A preferable example of the synthetic adsorption resin is a porous styrene resin having a specific surface area of 500 m 2 / g or more. Among them, as the adsorption resin, a styrene resin is preferable, and a styrene resin having a porous structure, a hydrophobic synthetic adsorption resin having no ion-exchange group, and a hydrophilic adsorption resin having a slight ion-exchange group are more preferable. As such an adsorption resin, for example, Muromac (registered trademark) SAP9121, SAP9210 (both from Muromachi Chemical Co., Ltd.) can be used.

[0023] As a treatment method for adsorbing a mixture containing ethanol and aroma components onto the resin, either a batch method or a column method can be adopted. From the viewpoint of workability, it is preferable to adopt the column method. When adsorbing by the column method, for example, by passing a mixture containing ethanol and aroma components through a column filled with the above resin, the aroma components can be adsorbed onto the resin. When the mixture containing ethanol and aroma components is in a liquid state, it is preferable to pass the mixture through the resin preferably 3 to 5 times by volume to adsorb the aroma components. From the viewpoint of increasing the adsorption rate of the aroma components, the mixture can also be passed through a plurality of times. In the case of the batch method, the aroma components can be adsorbed onto the resin by putting the mixture and the resin in a container and stirring them.

[0024] In step (C), ethanol is removed from the resin that has adsorbed the above aroma components. The removal of ethanol from the resin can be carried out by washing the resin adsorbed with aroma components with water. In the present invention, it is preferable to wash the resin adsorbed with the aroma components with water to remove ethanol from the resin. When the resin is washed with water, ethanol can be removed from the resin without eluting the aroma components. The washing with water may be performed by bringing the resin adsorbed with the aroma components into contact with water. When the aroma components are adsorbed by a column method, water may be passed through the column filled with the resin. For example, it is preferable to pass water through the resin in a volume of preferably 5 times or more, more preferably 10 times or more, and still more preferably 10 to 50 times. The temperature of the water is preferably 25°C or lower, more preferably 20°C or lower. For example, 5 to 25°C is preferable, and 5 to 20°C is more preferable. When the temperature of the water is within the above range, the recovery rate of the aroma components is further improved. From the viewpoint of more sufficiently removing ethanol, it is preferable to remove as much as possible the water used for washing from the resin after washing.

[0025] In step (D), the aroma components are recovered from the resin from which ethanol has been removed in step (C). The aroma components can be recovered by eluting the aroma components from the resin. In one aspect of the present invention, it is preferable to elute the aroma components from the resin with steam to recover the aroma components. The use of steam is preferable because the recovery rate of the aroma components is good and the ethanol concentration in the obtained aroma components is not increased.

[0026] By bringing water vapor into contact with a resin to elute aroma components and recovering and condensing the water vapor containing the aroma components, a solution containing the aroma components can be obtained. When using a column, by passing water vapor through a column filled with the above resin and condensing the vapor eluted from the column, a solution containing the aroma components can be recovered. The water vapor is preferably saturated water vapor. From the viewpoint of efficiently eluting the aroma components, the temperature of the water vapor is preferably 100°C or higher. Also, from the viewpoint of suppressing changes in the aroma components, the temperature of the water vapor is preferably 140°C or lower, more preferably 130°C or lower. In one aspect, the temperature of the water vapor is preferably 100 to 140°C, more preferably 100 to 130°C. The pressure of the water vapor is preferably 0.1 MPa or more in gauge pressure, more preferably 0.1 to 0.4 MPa, and even more preferably 0.1 to 0.3 MPa. In one aspect, it is preferable to use saturated water vapor whose pressure of the water vapor is within the above range.

[0027] The solution containing the aroma components and water obtained above can be used as it is in step (E), but if desired, it can be concentrated to increase the concentration of the aroma components or diluted for use. The method of concentration is not particularly limited, and for example, a concentration method using a reverse osmosis membrane (RO membrane), a method by vacuum distillation, etc. can be used.

[0028] The aroma components recovered in step (D) are aroma components derived from the raw material alcoholic beverage, and by mixing them with beverages, etc., the flavor possessed by the alcoholic beverage can be imparted. In the present invention, by separating the aroma components and ethanol by the treatment using the above resin, aroma components substantially free of ethanol can be efficiently obtained. Substantially free of ethanol means that the ethanol concentration is less than 0.100 v / v%, preferably the ethanol concentration is 0.05 v / v% or less. Also, when using the above resin for separating the aroma components and ethanol, the aroma components can be obtained at a high recovery rate.

[0029] In step (E), a dealcoholized beverage is obtained by mixing the aroma components obtained above with the residual liquid obtained in step (A). The mixing amount of the aroma components is not particularly limited and may be all or part of the amount recovered in step (D), and can be appropriately selected. Even when the aroma components obtained in step (D) are mixed into the residual liquid, since the ethanol concentration hardly increases with the mixing of the aroma components, a dealcoholized beverage with a reduced ethanol concentration and imparted with the flavor of the raw material alcoholic beverage can be produced.

[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 with an ethanol concentration reduced to the above range can be produced. The dealcoholized beverage can also be referred to as a low-alcohol beverage.

[0031] According to the present invention, a dealcoholized beverage containing the flavor components of the raw material alcoholic beverage and having a reduced ethanol concentration can be obtained. The dealcoholized beverage obtained by the present invention is a beverage in which ethanol is separated from the raw material alcoholic beverage and the residual liquid with the ethanol concentration preferably reduced to less than 0.005 v / v% is blended. Also, since the aroma components contained in the raw material are included, the flavor of the alcoholic beverage before ethanol separation can be obtained. The production method of the dealcoholized beverage of the present invention is particularly suitable for beer, fruit wine, and sake, and is particularly suitable for reducing the ethanol content of beer. In a preferred embodiment of the present invention, for example, when beer is used as the raw material, a dealcoholized beer having the original flavor of beer and an ethanol concentration of less than 0.005 v / v% can be produced.

[0032] As an example of the aroma components contained in alcoholic beverages, for example, in the case of beer, acetaldehyde, ethyl acetate, i-butanol, isoamyl acetate, isoamyl alcohol, etc. can be mentioned. According to one aspect of the present invention, it is possible to produce a de-alcoholized 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, based on the content (100%) in the beer used as the raw material.

[0033] The de-alcoholized beverage obtained by the production method of the present invention can be suitably consumed as a beverage as it is. Further, by mixing the de-alcoholized beverage obtained by the production method of the present invention with ethanol to adjust the ethanol concentration, an alcoholic beverage (alcohol-containing beverage) having a desired ethanol concentration can be produced. A method for producing an alcoholic beverage including a step of mixing the de-alcoholized beverage produced by the above production method of the present invention with ethanol to adjust the ethanol concentration is also one of the present inventions. For the addition of ethanol, any alcohol-containing beverage containing ethanol can also be used.

[0034] The present invention also includes a method for producing aroma components derived from alcoholic beverages (hereinafter, also simply referred to as a method for producing aroma components). The method for producing aroma components derived from alcoholic beverages of the present invention includes a step (A) of separating ethanol and aroma components from an alcoholic beverage to obtain a mixture containing the above ethanol and aroma components and a residual liquid from which ethanol and aroma components have been separated from the above alcoholic beverage; a step (B) of bringing a resin into contact with the mixture containing the above ethanol and aroma components to adsorb the above aroma components onto the resin; a step (C) of removing ethanol from the resin adsorbed with the above aroma components; and a step (D) of recovering the aroma components from the resin from which ethanol has been removed in the above step (C). Figure 2 is a process diagram showing an example of a method for producing an aroma component derived from an alcoholic beverage of the present invention. Steps (A) to (D) and their preferred embodiments in the method for producing the aroma component of the present invention are the same as steps (A) to (D) and their preferred embodiments in the method for producing the non-alcoholic beverage of the present invention described above. The method for producing the aroma component 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 component and its preferred embodiments obtained by the production method of the present invention are the same as the aroma component and its preferred embodiments obtained by the production method of the above non-alcoholic beverage. The aroma component obtained by the production method of the present invention is an aroma component derived from the alcoholic beverage as a raw material, and can impart the flavor possessed by the alcoholic beverage by mixing it with beverages and the like.

[0035] The alcoholic beverage and its preferred embodiments used in the method for producing the aroma component of the present invention are the same as the alcoholic beverage and its preferred embodiments used in the method for producing the non-alcoholic beverage described above. For example, when beer is used as the alcoholic beverage, an aroma component (which can also be referred to as an aroma component composition) containing one or more compounds among acetaldehyde, ethyl acetate, i-butanol, isoamyl acetate, and isoamyl alcohol can be obtained.

Examples

[0036] Examples for more specifically explaining the present invention are shown below. Note that the present invention is not limited only 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] <Measurement method of ethanol content> The ethanol content of samples such as a dealcoholized sample obtained from an alcoholic beverage and a distillate (condensate) was measured by GC / MS (product name: 6890series GC system, 5973 Network Mass selective Detercter, manufactured by Agilent). For the samples used for measurement, analysis was carried out by adding an internal standard (acetone) without any pretreatment. The measurement conditions of GC / MS are as follows. The calibration curve was prepared according to the order of the ethanol concentration of the sample for quantification. For example, when measuring a 0.005% sample, the calibration curve was prepared at 5 points (at least 3 points) between 0.001% and 0.01%.

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

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

[0040] <Reference Example 1> Alcohol Removal Using Vacuum Steam Distillation 1. Raw Materials and Equipment As raw materials, commercially available beer (Alc 5.5%, hereinafter referred to as Beer A) and commercially available non-alcoholic beer (non-alcoholic beer made in a foreign country (a country other than Japan), Alc 0.5%, hereinafter referred to as Non-alcoholic Beer B) were used. Vacuum steam distillation was carried out using a continuous countercurrent gas-liquid extraction device.

[0041] 2. Examination of Steam Distillation Conditions The raw materials were supplied to the above device for vacuum steam distillation, and the ethanol concentration of the residual liquid (alcohol-removed sample) after distillation was measured. When performing alcohol removal by steam distillation, it was known that the amount of steam relative to the amount of alcoholic beverage is an important parameter. Therefore, the number of treatment times, raw material feed flow rate, and steam temperature that can change the amount of steam relative to the amount of beer were set as parameters, and the relationship between each parameter and alcohol removal was examined.

[0042] 2.1 Influence of the Number of Treatments on Alcohol Removal By changing the number of treatments of vacuum steam distillation, the effect of changing the vacuum steam distillation treatment time was examined. When performing the process multiple times, after the first process is completed, only the bottom of the column is depressurized and the recovered dealcoholized sample is reapplied to the top of the column. The vacuum steam distillation conditions are shown in Condition 1 below. The reason for setting the column wall temperature and the column bottom temperature higher than the steam temperature is that if carried out at the same temperature, steam will condense on the column wall and bottom. Note that the vacuum steam distillation treatment time can also be changed by varying the length of the column.

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

[0044] Table 1 shows the ethanol concentration in the dealcoholized sample when the number of treatments is changed. The time for the vacuum steam distillation treatment was 10 minutes per treatment. After 3 treatments, the ethanol concentration reached 0.001 v / v%.

[0045]

Table 1

[0046] 2.2 Influence of steam temperature on dealcoholization The influence of steam temperature on the ethanol concentration of the dealcoholized sample was investigated. Since increasing the steam temperature increases the steam density, the amount of steam relative to the beer can be changed. The vacuum steam distillation conditions are shown in Condition 2 below. The number of treatments was set to 1. Table 2 shows the ethanol concentration in the dealcoholized sample when the steam temperature was changed.

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

[0048]

Table 2

[0049] 2.3 Influence of differences in raw material feed volume and alcohol content on dealcoholization The influence of ethanol concentration etc. in the raw material on the ethanol concentration in the sample after dealcoholization was investigated. The vacuum steam distillation conditions are shown in Condition 3 below. The number of treatment times was 1. The results are shown in Table 3.

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

[0051]

Table 3

[0052] <Example 1> Examination of the Separation Technology of Alcohol and Aroma in Distillate By subjecting Beer A to vacuum distillation (using an evaporator), a beer distillate containing ethanol and aroma components (ethanol concentration 12 v / v%) was obtained. The conditions for vacuum distillation are as follows. Beer A is the same as that used in Reference Example 1. Temperature: 30°C Absolute pressure: 0.0027 MPa Concentration: Vacuum distillation was carried out until 500 mL of Beer A was reduced to 300 mL (Carried out until 200 mL of distillate can be obtained from 500 mL of Beer A)

[0053] The separation method of aroma components and ethanol using an adsorption resin was examined. For the recovery of aroma components from the distillate by the adsorption resin, Muromac (registered trademark) SAP9121 and SAP9210 (both from Muromachi Chemical Co., Ltd.) were used. These are styrene-based resins. The adsorption principle of these resins applies the van der Waals force to perform the adsorption and desorption of components, and by applying energy greater than the van der Waals force acting between the resin and the components, it is possible to desorb the components.

[0054] Similar to general resins, before use, the resin was swollen and washed, and then, in order to adsorb the aroma components to the resin, 400 mL of the resin was packed into a column, and 1450 mL of the above-obtained beer distillate was passed through it. The passage was carried out 5 times to increase the adsorption rate of the aroma components. Then, 4000 mL of pure water (20°C) was passed through to remove the ethanol remaining in the column. After discharging as much pure water remaining in the column as possible after washing, the recovery of aroma components by steam was carried out. Steam was passed through the column to elute the aroma components from the resin. The conditions for aroma component recovery were carried out using steam at 100°C or higher with a steam pressure of 0.2 MPa (gauge pressure), and the steam was condensed by a condenser installed at the column outlet and recovered as an aroma solution. In addition, during the recovery, it was recovered in fractions of 500 mL each, and a total of 8 L of aroma solution was recovered. The ethanol concentration of Fractions 1 to 16 was measured.

[0055] Table 4 shows the ethanol concentrations of Fractions 1 to 16 when using Muromac (registered trademark) SAP9121. After Fraction 2, the ethanol concentration was 0.002 v / v% or less. When using Muromac (registered trademark) SAP9120, the ethanol concentration was also 0.002 v / v% or less after Fraction 2.

[0056]

Table 4

[0057] In addition, the content of low-boiling compounds (LVC) in the aroma solution (a solution obtained by mixing Fractions 1 to 16) was analyzed, and the recovery rate (%) from the raw material was determined. 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, assuming the amount of LVC in the raw material is 100%. The recovery rate was higher when using Muromac (registered trademark) SAP9121 than when using SAP9120. Table 5 shows the recovery rate of aroma components when using Muromac (registered trademark) SAP9121.

[0058] <Comparative Example 1> Using the beer distillate produced in Example 1, ethanol was separated using an RO membrane. The device was a flat membrane device manufactured by Alfa Laval, and the RO membrane used was GE FLAT SHEET AG (12×12) (effective filtration area per sheet of 0.018125 m 2 ) manufactured by GE Healthcare. Figure 3 shows the flow overview of the separation test using the RO membrane. The RO membrane used selectively permeates ethanol and water, and the permeate passing through the RO membrane contains ethanol, water, and also contains some aroma components. The separation conditions using the RO membrane are as follows. The beer distillate was first diluted with water and started from a state where the volume was increased, and the recovery rate and others were evaluated based on the results of analyzing the sample after dilution. Beer distillate: 2647 mL (started after diluting with water to 18900 g) Ethanol concentration: 12 v / v% before dilution, 1.34 v / v% after dilution Flow rate: 5 mL / min Gauge pressure inside the device: 2.4 - 3.0 MPa

[0059] Since RO membrane separation needs to be carried out for a long time, 2°C cold water was used to cool the device inlet and the test was carried out while ice-cooling the circulating liquid. Also, as the separation progressed, the circulating liquid decreased, so water was added as needed and separation was carried out for 8.6 hours until the ethanol content of the circulating liquid reached 0 v / v%. When the ethanol on the circulation side reached 0 v / v%, water addition was stopped and the liquid was concentrated as much as possible to recover the circulating liquid as much as possible. Regarding the measurement of the ethanol amount on the circulation side, for the samples after the experiment, measurement was carried out by GC / MS, but since measurement by GC / MS could not be carried out during the test, measurement was carried out using an Anton Paar densitometer. The content of low-boiling compounds in the recovered circulating liquid was analyzed and the recovery rate (%) from the raw material was determined. 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 separating the aroma components and ethanol using resin, the recovery rate of the aroma components was higher compared to RO membrane separation. Also, when using resin, the aroma components and ethanol could be separated in a shorter time than when using an RO membrane.

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

[0063] Regarding the distillate obtained by vacuum steam distillation of Beer A (Alc 11.06%), the aroma components were adsorbed onto an adsorption resin (Muromac (registered trademark) SAP9121, Muromachi Chemical Co., Ltd.) in the same manner as in Example 1, then the resin was washed with water, and the aroma components were eluted with steam to obtain an aroma solution (Alc 0.02 v / v%). The obtained aroma solution was concentrated to prepare 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 a dealcoholized beer (II) with an ethanol concentration of 0.0048 v / v%. (Evaluation) For the purpose of confirming whether the brewing-derived aroma can be imparted by adding the recovered aroma, a comparison between the dealcoholized sample (I) and the dealcoholized beer (II) was conducted. Sensory evaluation was carried out by 4 trained panelists (Panelists A to D). The evaluation items were the brewing aroma characteristic of beer (the aroma characteristic of beer produced during brewing), the wort odor, and the deteriorated flavor. Each sample was held in the mouth, and the above items were evaluated on a scale of 0 to 3 points in 13 steps at 0.25-point intervals according to the following criteria, and then the average value of the panelists' scores was obtained. In non-alcoholic beer, the wort odor is regarded as negative. Therefore, it can be said that the weaker the wort odor, the better the flavor. The deteriorated flavor is a flavor that has a negative impact due to the heating odor or sourness generated by heating. When the components deteriorate due to the heat load during vacuum distillation, the deteriorated flavor odor becomes stronger.

[0064] (Brewing aroma characteristic of beer) 0: Strongly feel the brewing aroma characteristic of beer 1: Feel the brewing aroma characteristic of beer 2: Slightly feel the brewing aroma characteristic of beer 3: Do not feel the brewing aroma characteristic of beer

[0065] (Wort odor) 0: Do not feel wort odor 1: Slightly feel wort odor 2: Feel wort odor 3: Strongly feel wort odor

[0066] (Deteriorated flavor) 0: Do not feel deteriorated flavor 1: Slightly feel deteriorated flavor 2: Feel deteriorated flavor 3: Strongly feel deteriorated flavor

[0067] The scores of each panelist and the average score are shown in Tables 6 - 8. Table 6 shows the evaluation results of the brewing aroma characteristic of beer, Table 7 shows the evaluation results of wort odor, and Table 8 shows the evaluation results of deteriorated flavor.

[0068]

Table 6

[0069]

Table 7

[0070]

Table 8

[0071] From the above results, by separating ethanol and aroma components from beer and adding the aroma components with ethanol removed to the non - alcoholic sample of beer, a brewing aroma characteristic of beer could be imparted. Also, it was confirmed that simply separating ethanol from beer makes wort odor and deteriorated flavor prominent, but these flavors can be reduced. When ethanol is removed from beer, the beer - like aroma flies away and the beer - like quality is reduced, but by removing ethanol from the recovered aroma components and adding them, a beer - like quality can be imparted and a non - alcoholic beer with a reduced ethanol concentration can be produced.

Claims

1. A step (A) 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 ethanol and the aroma components to allow the resin to adsorb the aroma components; A step (C) of removing ethanol from the resin having adsorbed the aroma components; A step (D) of recovering aroma components from the resin from which ethanol has been removed in the step (C); and The method includes a step (E) of mixing the residual liquid obtained in the step (A) with the aroma components obtained in the step (D) to obtain a dealcoholic beverage. A method for producing a non-alcoholic beverage.

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

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

6. The method for producing a dealcoholic beverage according to any one of claims 1 to 5, wherein the ethanol concentration of the dealcoholic beverage obtained in the step (E) is less than 0.005 v / v%.

7. The method for producing a dealcoholic beverage according to any one of claims 1 to 6, wherein the resin is a styrene-based resin.

8. The method for producing a dealcoholic beverage according to any one of claims 1 to 7, wherein in the step (C), the resin that has adsorbed the aroma components is washed with water to remove ethanol.

9. The method for producing a dealcoholic beverage according to any one of claims 1 to 8, wherein in the step (D), aroma components are eluted from the resin by steam to recover the aroma components.

10. A method for producing an alcoholic beverage using a dealcoholic beverage produced by the production method according to any one of claims 1 to 9, comprising a step of mixing the dealcoholic beverage with ethanol to adjust the ethanol concentration. The method for producing an alcoholic beverage.

11. A step (A) 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 ethanol and the aroma components to allow the resin to adsorb the aroma components; (C) removing ethanol from the resin having adsorbed the aroma components; and and (D) recovering aroma components from the resin from which ethanol has been removed in the step (C). A method for producing aroma components derived from alcohol-containing beverages.

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