Method and system for recovering polar and non-polar aromatic compounds from dealcoholized beverages

Abstract

A consumable article prepared from an alcoholic beverage comprising 0.045% or less ethanol by volume, wherein the consumable article is characterized as having an amount of inherent volatile organic compounds (VOCs); and, wherein the inherent VOCs comprise a plurality of inherent aromatic compounds; and, wherein the consumable article has a MeOH content that is at least one of: a. below the level of detection when measured by Procedure A; b. less than 0.01% by volume; and, wherein the consumable article has a ratio of EtAc to the amount of inherent VOCs of 1:0.2 to 1:300 when measured by Procedure B.

Description

Technical Field

[0001] This invention relates to the field of food and beverages. More specifically, this invention relates to low / non-alcoholic drinkable products with desirable taste and aroma characteristics, and methods for preparing the same. Background Technology

[0002] The demand for low-alcohol or non-alcoholic alcoholic or fermented beverages is increasing. This phenomenon is directly caused by the harms of excessive drinking, such as the serious problem of alcohol poisoning, as well as other serious problems such as domestic violence and traffic accidents caused by drunk driving; in addition, millions of people abstain from alcohol for cultural or religious reasons.

[0003] Like many other popular fermented alcoholic beverages, wine has over 1,000 different aroma or flavor compounds, of which approximately 400 are produced during fermentation. It has been shown that dealcoholization can remove some of these volatile compounds, affecting the flavor of lower-alcohol products (Food, 2021).

[0004] One of the biggest challenges facing the industry is maintaining the inherent taste and aroma of low / non-alcoholic versions of popular beverages and giving consumers a genuine “drinking experience.”

[0005] The production of non-alcoholic beverages that offer a similar aroma and taste experience to original alcoholic products remains a long-standing and unmet need. Summary of the Invention

[0006] The main objective of this invention is to provide a low / non-alcoholic version of a popular beverage with its inherent flavor and aroma, and to allow consumers to have a genuine “drinking experience”.

[0007] According to some embodiments, the present invention provides a drinkable product prepared from an alcoholic beverage containing 0.045 vol% or less ethanol, wherein the drinkable product has a certain amount of inherent volatile organic compounds (VOCs); and wherein the inherent VOCs include a variety of inherent aromatic compounds; and wherein the MeOH content in the drinkable product satisfies at least one of the following: a. When measured using procedure A, the level is below the detection threshold; b. less than 0.01% by volume; and, The ratio of EtAc to the intrinsic median VOC (20) in the drinkable product is from 1:0.2 to 1:300.

[0008] According to some embodiments, the present invention provides a drinkable product prepared from an alcoholic beverage containing 0.045 vol% or less ethanol, said drinkable product having a certain amount of inherent volatile organic compounds (VOCs); the amount of said inherent VOCs includes a variety of inherent aromatic compounds, and when measured by procedure A, the MeOH content in said drinkable product is below the detection level and / or less than 0.01 vol%; and said drinkable product also satisfies at least one of the following: a. The ratio of EtAc to hexanoic acid is 1:0.02 to 1:250; b. The ratio of EtAc to phenylethanol is 1:0.01 to 1:245; c. The ratio of EtAc to octanoic acid is 1:0.3 to 1:300; d. The ratio of EtAc to nonanoic acid is 1:0.1 to 1:100; and The ratio of e.EtAc to decanoic acid is 1:0.3 to 1:320; The ratio mentioned therein was measured by procedure B.

[0009] According to some embodiments, the present invention provides a drinkable product prepared from an alcoholic beverage containing 0.045 vol% or less ethanol, the drinkable product having a certain amount of inherent volatile organic compounds (VOCs); and wherein the inherent VOCs include a variety of inherent aromatic compounds; and the MeOH content in the drinkable product satisfies at least one of the following: c. When measured using procedure A, the level is below detection threshold; d. Less than 0.01% of the volume; and, The inherent VOC comprises at least 70% of the various inherent aromatic compounds found in alcoholic beverages made into drinkable products.

[0010] According to some embodiments, the present invention provides a method for preparing a drinkable product as described in the embodiments of the present invention, the method comprising: a. Recovering at least the majority of the various inherent aromatic compounds of VOCs from alcoholic beverages; and, b. Prepare a drinkable product containing a certain amount of VOC, wherein the VOC contains a variety of inherent aromatic compounds; The step of recovering multiple aromatic compounds from an alcoholic beverage includes at least a pre-concentration and a concentration step; the pre-concentration step includes preparing a pre-concentrate containing multiple aromatic compounds from raw materials derived from the alcoholic beverage; the concentration step includes preparing a concentrate containing multiple aromatic compounds from the pre-concentrate; the pre-concentration and concentration steps each independently include at least one cycle: adsorption on at least one column loaded with an adsorbent, the adsorbent binding at least most of the multiple inherent aromatic compounds; and desorption of the multiple inherent aromatic compounds from the at least one column with a desorbent.

[0011] According to some embodiments, the present invention provides a method for preparing a drinkable product as described in the embodiments of the present invention, comprising the following steps: a. Provide a raw material having up to 50% by volume ethanol, said raw material being derived from an alcoholic beverage and containing a certain amount of VOCs, said VOCs comprising a variety of inherent aromatic compounds of the alcoholic beverage; b. To prepare a concentrate containing a variety of inherent aromatic compounds; and, c. Obtain a drinkable product containing a certain amount of VOC from the concentrate of step b, wherein the VOC contains a variety of inherent aromatic compounds. Detailed Implementation Invention Details

[0013] Before detailing at least one embodiment of the present invention, it should be understood that the scope of the present invention is not limited to the specific structural details and component arrangements described below. The present invention can be implemented or applied in many other forms. Furthermore, the terminology and expressions used herein are for descriptive purposes only and should not be considered as limiting the present invention.

[0014] According to some embodiments, the present invention provides a drinkable product with a low alcohol content.

[0015] According to some embodiments, the present invention provides a non-alcoholic drinkable product.

[0016] In the context of this invention, beverages associated with the terms "low alcohol" and / or "non-alcoholic" are considered to have a lower alcohol content or concentration than standard alcoholic beverages. The exact definitions of the above terms may vary in different regions and therefore should not be considered and / or construed as limiting.

[0017] In the context of this invention, when used with alcoholic beverages, the term "alcohol concentration" refers to, but is not limited to, "ethanol concentration," or specifically refers to the volume concentration of ethanol. The above definition may be used interchangeably with the term "%vol." (which may be preceded by the word "alcohol" or the abbreviation "alc"), "alcohol volume," "ethanol volume," ABV, or %ABV. ABV is typically calculated as the volume (in milliliters) of 100 milliliters (at 20°C) of alcohol (or ethanol).

[0018] In the context of this invention, when referring to beverages, the term "low alcohol" can be interpreted non-limitingly as a beverage with an alcohol content of less than 1.2 ABV.

[0019] In the context of this invention, when referring to beverages, the term "non-alcoholic" can be understood to mean, but is not limited to, beverages with an ethanol content of ≤0.5% by volume. Optionally and / or additionally, the above term can be understood to mean, but is not limited to, a subclass of "non-alcoholic" beverages with an ethanol content of ≤0.04% by volume.

[0020] In the context of this invention, the term "drinkable product" may be used interchangeably with the term "beverage," referring to any beverage other than water.

[0021] According to some embodiments, the aforementioned drinkable product has 0.045% by volume or less ethanol and is prepared from an alcoholic beverage containing a variety of inherent aromatic compounds, wherein the methanol (MeOH) content of the drinkable product is at least 10 times lower than the methanol content of the alcoholic beverage, and wherein the drinkable product contains at least 70% of the various inherent aromatic compounds of the alcoholic beverage used to prepare the drinkable product. According to some embodiments, the methanol (MeOH) content of the drinkable product is at least 100 times lower than the methanol content of the alcoholic beverage. According to some embodiments, the methanol (MeOH) content of the drinkable product is at least 1000 times lower than the methanol content of the alcoholic beverage. According to some embodiments, the methanol (MeOH) content of the drinkable product is at least 10000 times lower than the methanol content of the alcoholic beverage. According to some embodiments, the methanol (MeOH) content of the drinkable product is 10 to 10000 times lower than the methanol content of the alcoholic beverage.

[0022] According to some embodiments, the above-mentioned drinkable product has 0.045% by volume or less ethanol, wherein the drinkable product is prepared from an alcoholic beverage and has a certain amount of inherent volatile organic compounds (VOCs) when measured by procedure B; and the VOCs contain a variety of inherent aromatic compounds; and the methanol (MeOH) content in the drinkable product is below the detection level when measured by procedure A; and wherein the ratio of ethyl acetate (EtAc) to median VOC (20) is 0.2 to 1:300.

[0023] The term "volatile organic compounds" (VOCs) here refers to organic compounds that have a high vapor pressure at room temperature. Some VOCs are further classified as aromatic compounds because their volatility is sufficient to enter the olfactory system.

[0024] Volatile organic compounds are typically analyzed using gas chromatography, often in combination with gas chromatography-mass spectrometry (GCMS), headspace solid-phase microextraction and gas chromatography-tandem mass spectrometry (HS-SPME-GC-MS / MS) or HS-GC-flame ionization detector (FID).

[0025] In the context of this invention, the term "VOC(20)" refers to the 20 most abundant VOCs in a sample detected by procedure B, wherein ethyl acetate (EtAc), ethanol (EtOH), methanol, dichloromethane, and other impurity peaks introduced or generated during sample preparation or detection are negligible. In the context of this invention, the term "median VOC(20)" refers to the calculated median of VOC(20), and the term "total VOC(20)" refers to the total amount of VOC(20).

[0026] According to some implementation schemes, the ratio of EtAc to the intrinsic median VOC (20) of any of the above-mentioned drinkable products is 0.5 to 1:200.

[0027] According to some implementation schemes, the ratio of EtAc to the intrinsic median VOC (20) of any of the above-mentioned drinkable products is 1:1 to 1:125.

[0028] According to some implementation schemes, the ratio of EtAc to the intrinsic median VOC (20) of any of the above-mentioned drinkable products is 1:2 to 1:75.

[0029] According to some implementation schemes, the ratio of EtAc to the intrinsic median VOC (20) of any of the above-mentioned drinkable products is 1:3 to 1:50.

[0030] According to some implementation schemes, the ratio of EtAc to the intrinsic median VOC (20) of any of the above-mentioned drinkable products is 1:4 to 1:25.

[0031] According to some implementation schemes, the ratio of EtAc to the intrinsic median VOC (20) of any of the above-mentioned drinkable products is 1:5 to 1:15.

[0032] According to some implementation schemes, any of the above-mentioned drinkable products contain less than 50 ppm of EtAc.

[0033] According to some implementation schemes, the amount of inherent total VOC (20) in any of the above-mentioned drinkable products is at least 100 ppm.

[0034] In the context of this invention, the VOC ppm is calculated as ppm DMOT (m / z 154) equivalent and is related to the peak area of ​​DMOT.

[0035] According to some implementation schemes, the amount of inherent total VOC (20) in any of the above-mentioned drinkable products is at least 150 ppm.

[0036] According to some implementation schemes, any of the above-mentioned drinkable products have at least 10 inherent VOCs at a concentration of at least 1 ppm.

[0037] According to some implementation schemes, any of the above-mentioned drinkable products have at least 10 inherent VOCs at a concentration of at least 2 ppm.

[0038] According to some implementation schemes, any of the above-mentioned drinkable products have at least 10 inherent VOCs at a concentration of at least 2 ppm.

[0039] According to some embodiments, prior to the dealcoholization process, the aforementioned drinkable product has the same flavor characteristics as an alcoholic beverage. According to some embodiments, the drinkable product contains no additional flavorings and / or colorings.

[0040] In the context of this invention, when referring to dealcoholized beverages, the terms "added flavoring agent," "added flavoring agent," or "added coloring agent" mean any flavoring or coloring compound added to a dealcoholized beverage that is not present in or extracted from an alcoholic beverage. Terms such as "natural flavoring," "extract," or "natural coloring" are frequently used to describe flavorings or colorings added to non-alcoholic beverages.

[0041] According to some embodiments, the drinkable product has 0.045% by volume or less ethanol, wherein the drinkable product is prepared from an alcoholic beverage and has a certain amount of inherent volatile organic compounds (VOCs); and when measured by procedure A, the MeOH content in the drinkable product is below the detection level and meets at least one of the following: 1. The ratio of EtAc to hexanoic acid is 1:0.02 to 1:250; 2. The ratio of EtAc to phenylethanol is 1:0.01 to 1:245; 3. The ratio of EtAc to octanoic acid is 1:0.3 to 1:300; 4. The ratio of EtAc to nonanoic acid is 1:0.1 to 1:100; and, 5. The ratio of EtAc to decanoic acid is 1:0.3 to 1:320.

[0042] According to some implementation schemes, the ratio of EtAc to hexanoic acid in the drinkable product is from 1:0.004 to 1:150.

[0043] According to some implementation schemes, the ratio of EtAc to hexanoic acid in the drinkable product is from 1:0.01 to 1:100.

[0044] According to some implementation schemes, the ratio of EtAc to hexanoic acid in the drinkable product is from 1:0.05 to 1:75.

[0045] According to some implementation schemes, the ratio of EtAc to hexanoic acid in the drinkable product is from 1:0.1 to 1:50.

[0046] According to some implementation schemes, the ratio of EtAc to hexanoic acid in the drinkable product is 1:0.5 to 1:25.

[0047] According to some implementation schemes, the ratio of EtAc to phenylethanol in the drinkable product is from 1:0.004 to 1:150.

[0048] According to some implementation schemes, the ratio of EtAc to phenylethanol in the drinkable product is from 1:0.05 to 1:75.

[0049] According to some implementation schemes, the ratio of EtAc to phenylethanol in the drinkable product is from 1:0.1 to 1:50.

[0050] According to some implementation schemes, the ratio of EtAc to phenylethanol in the drinkable product is from 1:0.3 to 1:15.

[0051] According to some implementation schemes, the ratio of EtAc to octanoic acid in the drinkable product is from 1:0.0035 to 1:150.

[0052] According to some implementation schemes, the ratio of EtAc to octanoic acid in the drinkable product is from 1:0.005 to 1:75.

[0053] According to some implementation schemes, the ratio of EtAc to octanoic acid in the drinkable product is from 1:0.1 to 1:50.

[0054] According to some implementation schemes, the ratio of EtAc to octanoic acid in the drinkable product is from 1:0.25 to 1:15.

[0055] According to some implementation schemes, the ratio of EtAc to nonanoic acid in the drinkable product is from 1:0.01 to 1:50.

[0056] According to some implementation schemes, the ratio of EtAc to nonanoic acid in the drinkable product is from 1:0.03 to 1:25.

[0057] According to some implementation schemes, the ratio of EtAc to nonanoic acid in the drinkable product is from 1:0.05 to 150.

[0058] According to some implementation schemes, the ratio of EtAc to nonanoic acid in the drinkable product is from 1:0.1 to 1:75.

[0059] According to some implementation schemes, the ratio of EtAc to decanoic acid in the drinkable product is from 1:0.01 to 1:15.

[0060] According to some implementation schemes, the ratio of EtAc to decanoic acid in the drinkable product is from 1:0.01 to 1:7.5.

[0061] According to some implementation schemes, the ratio of EtAc to decanoic acid in the drinkable product is from 1:0.2 to 1:5.

[0062] According to some implementation schemes, the ratio of EtAc to decanoic acid in the drinkable product is 1:0.5 to 1:1.

[0063] As described herein, the term "aromatic compound" (also known as flavoring agent, aroma agent, fragrance, or flavoring agent) refers to, but is not limited to, chemical compounds or substances having an odor or aroma. These aromatic compounds influence the sensory impression of a beverage, primarily its flavor and aroma. Many aromatic compounds in alcoholic beverages are products of, but not limited to, fermentation and / or aging processes. Non-limiting examples of aromatic compounds in the beverages of this invention include geraniol, (Z)-3-hexenal, β-ionone, (R)-linalool, myrcene, nonanal, (R)-α-pinene, ethyl 3-methylbutyrate, hexanal, and 1,8-cineole, ethyl acetate, ethyl butyrate, isobutanol, isoamyl acetate, 2-methylbut-1-ol, 3-methylbut-1-ol, ethyl hexanoate, 2-phenylethyl acetate, 2-phenylethanol, or any combination thereof. Preferably, 2-methylbut-1-ol and / or 3-methylbut-1-ol are preferred.

[0064] In the context of this invention, the term "intrinsic aromatic compound" should be understood as an aromatic compound that is originally present in the alcoholic beverage in which the drinkable article of this invention is prepared.

[0065] Throughout the invention, in the above and foregoing embodiments of the invention, the term "multiple inherent aromatic compounds" should be read, interpreted, understood and / or interpreted as a group of aromatic compounds that do not contain methanol.

[0066] According to the above and foregoing embodiments of the present invention, it should be understood that the various inherent aromatic compounds contained in the drinkable products, raw materials, pre-concentrates and concentrates of the present invention account for at least a majority of the total; however, not all aromatic compounds present in alcoholic beverages are included in these drinkable products, raw materials, pre-concentrates and concentrates.

[0067] According to some embodiments, the present invention provides a drinkable product prepared from an alcoholic beverage having less than 0.045% ABV or 0.045% vol% ethanol (EtOH), having a certain amount of inherent volatile organic compounds (VOCs); said inherent VOCs include a variety of inherent aromatic compounds; and said inherent VOCs comprise at least 70% of the variety of inherent aromatic compounds in the alcoholic beverage used to make said drinkable product; and wherein, when measured by procedure A, the methanol (EtOH) content in the drinkable product is below the detection level; and wherein, when measured by procedure B, the ratio of EtOH vol% to the amount of inherent median VOC (20) in the drinkable product is 5 to 15000; and said drinkable product does not contain added flavorings.

[0068] According to some implementation schemes, the ratio of ethanol volume% to the intrinsic median VOC (20) in the drinkable product is 15 to 5000.

[0069] According to some implementation schemes, the ratio of ethanol volume% to the intrinsic median VOC (20) in the drinkable product is 25 to 1500.

[0070] According to some implementation schemes, the ratio of ethanol volume% to the intrinsic median VOC (20) in the drinkable product is 50 to 1000.

[0071] According to some implementation schemes, the ratio of ethanol volume% to the intrinsic median VOC (20) in the drinkable product is 100 to 500.

[0072] According to some implementation schemes, any of the above-mentioned drinkable products contain 0.01% by volume or less ethanol.

[0073] According to some implementation schemes, any of the above-mentioned drinkable products contain 0.0045% by volume or less ethanol.

[0074] According to some implementation schemes, the ethanol content of any of the above-mentioned drinkable products is 0.045 vol%, 0.044 vol%, 0.043 vol%, 0.042 vol%, 0.041 vol%, 0.040 vol%, 0.039 vol%, 0.038 vol%, 0.037 vol%, 0.036 vol%, 0.035 vol%, 0.034 vol%, 0.033 vol%, 0.032 vol%, 0.031 vol%, 0.030 vol%, 0.029 vol%, 0.028 vol%, 0.027 vol%, 0.026 vol%, 0.025 vol%, 0.024 vol%. 0.023% by volume, 0.022% by volume, 0.021% by volume, 0.020% by volume, 0.019% by volume, 0.018% by volume, 0.017% by volume, 0.016% by volume, 0.015% by volume, 0.014% by volume, 0.013% by volume, 0.012% by volume, 0.011% by volume, 0.010% by volume, 0.009% by volume, 0.008% by volume, 0.007% by volume, 0.006% by volume, 0.005% by volume, 0.004% by volume, 0.003% by volume, 0.002% by volume, 0.001% by volume or less, or may have or may be completely free of ethanol.

[0075] According to some implementation schemes, the drinkable product is free of detectable methanol as measured by procedure A.

[0076] According to some implementation schemes, the methanol content of the drinkable product is 0.010 vol%, 0.009 vol%, 0.008 vol%, 0.007 vol%, 0.006 vol%, 0.005 vol%, 0.004 vol%, 0.003 vol%, 0.002 vol%, 0.001 vol% or less, or it may have or may not contain methanol at all.

[0077] According to some embodiments, when the ethanol content of the alcoholic beverage used to prepare the drinkable product of the present invention is between 3% and 50% by volume, the methanol content of the drinkable product is about 100 times to about 1500 times lower than the methanol content of the alcoholic beverage used to prepare the drinkable product.

[0078] According to some embodiments, when the ethanol content of the alcoholic beverage used to prepare the drinkable product of the present invention is 3.0 vol%, 3.5 vol%, 4.0 vol%, 4.5 vol%, 5.0 vol%, 5.5 vol%, 6.0 vol%, 6.5 vol%, 7.0 vol%, 7.5 vol%, 8.0 vol%, 8.5 vol%, 9.0 vol%, 9.5 vol%, 10.0 vol%, 10.5 vol%, 11.0 vol%, 11.5 vol%, 12.0 vol%, 12.5 vol%, 13.0 vol%, 13.5 vol%, 14.0 vol%, 14.5 vol%, 15.0 vol%, 15.5 vol%, 16.0 vol%,... 16.5% by volume, 17.0% by volume, 17.5% by volume, 18.0% by volume, 18.5% by volume, 19.0% by volume, 19.5% by volume, 20.0% by volume, 20.5% by volume, 21.0% by volume, 21.5% by volume, 22.0% by volume, 22.5% by volume, 23.0% by volume, 23.5% by volume, 24.0% by volume, 24.5% by volume, 25.0% by volume, 25.5% by volume, 26.0% by volume, 26.5% by volume, 27.0% by volume, 27.5% by volume, 28.0% by volume, 28.5% by volume, 29.0% by volume, 29.5% by volume, 30.0% by volume, 30.5% by volume, 31%. 0% by volume, 31.5% by volume, 32.0% by volume, 32.5% by volume, 33.0% by volume, 33.5% by volume, 34.0% by volume, 34.5% by volume, 35.0% by volume, 35.5% by volume, 36.0% by volume, 36.5% by volume, 37.0% by volume, 37.5% by volume, 38.0% by volume, 38.5% by volume, 39.0% by volume, 39.5% by volume, 40.0% by volume, 40.5% by volume, 41.0% by volume, 41.5% by volume, 42.0% by volume, 42.5% by volume, 43.0% by volume, 43.5% by volume, 44.0% by volume, 44.5% by volume, 45.0% by volume, 45.5% by volume. When the methanol content of the drinkable product is 46.0%, 46.5%, 47.0%, 47.5%, 48.0%, 48.5%, 49.0%, 49.5%, or 50.0%, the methanol content of the drinkable product is approximately 100, 150, 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800, 850, 900, 950, 1000, 1050, 1100, 1150, 1200, 1250, 1300, 1350, 1400, 1450, or 1500 times lower than the methanol content of the alcoholic beverage used to prepare the drinkable product.

[0079] According to some implementation schemes, at least a portion of the inherent aromatic compounds in the inherent VOCs of the drinkable product has a log Pow value of 0.7 to 3.5.

[0080] According to some implementation schemes, at least a portion of the inherent aromatic compounds in the inherent VOCs of the drinkable product has a log Pow value of 0.7 to 1.35.

[0081] According to some embodiments, the drinkable article comprises 70% to 100% of a variety of inherent aromatic compounds of the alcoholic beverage used to prepare the drinkable article. According to some embodiments, the drinkable article comprises at least 70%, 75%, 80%, 85%, 90%, 95%, 98%, 99%, or 100% of a variety of inherent aromatic compounds of the alcoholic beverage used to prepare the drinkable article.

[0082] According to some embodiments, the present invention provides a method for preparing a drinkable product as described in one or more embodiments.

[0083] According to some embodiments, the drinkable product has an improved taste compared to commercially available low / non-alcoholic beverages. According to some embodiments, the improved taste of the drinkable product is attributed to the selective recovery of inherent aromatic compounds. According to some embodiments, the selective recovery of aromatic compounds allows for control of the proportion and / or amount based on the type of specific inherent aromatic compounds added back to the non-alcoholic / low-alcoholic beverage, resulting in a better taste and an improved drinking experience.

[0084] According to some embodiments, the present invention provides a method for preparing a drinkable product having 0.045% by volume or less ethanol from an alcoholic beverage containing a variety of inherent aromatic compounds.

[0085] According to some implementation schemes, the method includes the following steps: a. Recovering various inherent aromatic compounds from alcoholic beverages; and, b. To prepare drinkable products containing a variety of inherent aromatic compounds from alcoholic beverages. The steps for recovering multiple aromatic compounds from alcoholic beverages include at least a pre-concentration and a concentration step. The pre-concentration step includes preparing a pre-concentrate containing multiple aromatic compounds from raw materials derived from the alcoholic beverage. The concentration step includes preparing a concentrate containing multiple aromatic compounds from the pre-concentrate. Each of the pre-concentration and concentration steps independently includes at least one cycle: adsorption on a column loaded with an adsorbent, the adsorbent binding multiple inherent aromatic compounds; and desorption of the multiple inherent aromatic compounds from the column using a desorbent. The methanol content of the drinkable product is at least 100 times lower than that of the alcoholic beverage, and the drinkable product contains at least 70% of the various inherent aromatic compounds of the alcoholic beverage.

[0086] According to some embodiments, the present invention provides a method for preparing a drinkable product as described in one or more embodiments, comprising the following steps: a. Provide a raw material having a maximum of 40% by volume ethanol, wherein the raw material is derived from an alcoholic beverage and contains a variety of inherent aromatic compounds of the alcoholic beverage; b. Preparing a pre-concentrate containing a variety of inherent aromatic compounds, wherein the preparation of the pre-concentrate includes at least one of the following cycles: i. The raw material is adsorbed onto a column containing an adsorbent, said adsorbent being bound to a variety of inherent aromatic compounds; and, ii. Desorb the adsorbed aromatic compounds from the column using a desorbent to obtain a pre-concentrate containing a variety of inherent aromatic compounds; c. Preparing a concentrate containing a variety of inherent aromatic compounds, wherein the preparation of the concentrate includes at least one of the following cycles: i. Dilute the preconcentrate from step “b-ii” to less than 40% by volume of ethanol to obtain a diluted preconcentrate containing a variety of inherent aromatic compounds; ii. The diluted pre-concentrate is adsorbed onto a column containing an adsorbent that binds to a variety of inherent aromatic compounds; and, iii. Desorb the various inherent aromatic compounds adsorbed in the column using a desorbent to obtain a concentrate; and, d. Prepare a drinkable product from the concentrate of step “c-iii”.

[0087] According to some embodiments, the present invention provides a method for preparing a drinkable article having a reduced content of at least one harmful volatile compound and 0.045% by volume or less ethanol from an alcoholic beverage, the method comprising the following steps: a. Provide a raw material having up to 40% ethanol by volume, wherein the raw material is derived from an alcoholic beverage and contains a variety of inherent aromatic compounds of the alcoholic beverage; b. Preparing a pre-concentrate containing a variety of inherent aromatic compounds, wherein the preparation of the pre-concentrate includes at least one of the following cycles: i. The raw material is adsorbed onto a column containing an adsorbent, said adsorbent being bound to a variety of inherent aromatic compounds; and, ii. Desorb the adsorbed aromatic compounds from the column using a desorbent to obtain a pre-concentrate containing a variety of inherent aromatic compounds; c. Preparing a concentrate containing a variety of inherent aromatic compounds, wherein the preparation of the concentrate includes at least one of the following cycles: i. Dilute the preconcentrate from step “b-ii” to less than 40% by volume of ethanol to obtain a diluted preconcentrate containing a variety of inherent aromatic compounds; ii. The diluted pre-concentrate is adsorbed onto a column containing an adsorbent, which binds to a variety of inherent aromatic compounds; iii. Desorb the various inherent aromatic compounds adsorbed in the column using a desorbent to obtain a concentrate; The harmful compounds are selected from methanol, ethyl carbamate, and acetaldehyde, and the content of said harmful compounds is at least 10 times lower than the content of said harmful compounds in alcoholic beverages.

[0088] According to some embodiments of the above-mentioned drinkable products and methods, the method further includes the step of measuring the concentrations of MeOH, EtOH, EtAc, VOC(20), hexanoic acid, phenylethanol, octanoic acid, nonanoic acid, decanoic acid, or any combination thereof.

[0089] According to some embodiments of the above-mentioned drinkable products and methods, the content of the harmful compound is at least 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53. 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100 times or more, lower than the content of the harmful compounds mentioned in the alcoholic beverage.

[0090] According to some embodiments, the present invention provides a concentrate for preparing a drinkable product as described in one or more of the above embodiments, the concentrate being prepared from an alcoholic beverage, and the concentrate containing a variety of inherent aromatic compounds of the alcoholic beverage; and the concentrate containing at least 10 times less harmful volatile compounds selected from methanol, ethyl carbamate and acetaldehyde than in the alcoholic beverage.

[0091] According to some embodiments of the above-mentioned concentrate, the content of the harmful compound is at least 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 5 4, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100 times or more, lower than the content of the harmful compounds mentioned in the alcoholic beverage.

[0092] According to some embodiments, the present invention provides a concentrate for preparing a drinkable article as described in one or more of the above embodiments, said concentrate being prepared from an alcoholic beverage, and said concentrate containing at least 70% of a plurality of inherent aromatic compounds of the alcoholic beverage. According to some embodiments, the concentrate contains at least 70%, 75%, 80%, 85%, 90%, 95%, 98%, 99%, or 100% of a plurality of inherent aromatic compounds of the alcoholic beverage used to prepare the drinkable article.

[0093] According to some embodiments, the present invention provides a method for preparing a concentrate according to one or more of the above embodiments, comprising the following steps: a. Provide a starting material having up to 40% vol% ethanol, wherein the starting material is derived from an alcoholic beverage and contains a variety of inherent aromatic compounds of the alcoholic beverage; b. Preparing a pre-concentrate containing a variety of inherent aromatic compounds, wherein the preparation of the pre-concentrate includes at least one of the following cycles: i. The raw material is adsorbed onto a column containing an adsorbent, said adsorbent being bound to a variety of inherent aromatic compounds; and, ii. Desorbing the adsorbed aromatic compounds from the column using a desorbent to obtain a pre-concentrate containing a variety of inherent aromatic compounds; and, c. Preparing a concentrate containing a variety of inherent aromatic compounds, wherein the preparation of the concentrate includes at least one of the following cycles: i. Dilute the preconcentrate from step “b-ii” to less than 40% by volume of ethanol to obtain a diluted preconcentrate containing a variety of inherent aromatic compounds; ii. The diluted pre-concentrate is adsorbed onto a column containing an adsorbent, which binds to a variety of inherent aromatic compounds; iii. Desorb the various inherent aromatic compounds adsorbed in the column using a desorbent to obtain a concentrate.

[0094] According to some embodiments of the above-mentioned drinkable products, concentrates, and methods, non-limiting examples of alcoholic beverages include: red wine, white wine, rosé wine, champagne, rice wine, and fruit wine. wine, Metaxa, cider, beer, mead, ale, spirits, martini, whiskey, brandy, liquor, rum, cherry brandy, calvados, cachaca, arrack, sake, raki, midori, feigling, curacao, gin, cognac, Armagnac, pisco, tequila, mezcal, grappa, raki, fruit spirits spirit, shochu, soju, Tiswin, Toddy, Tonto, Tuica, Ogogoro, Palinka, Plum Jerkum, Piotin, Pulque, Port, Sherry, Kvass, Chicha, Bijiu, Medronho, pina colada, Ouzo, Aquavit, Absinthe, Gin, or any combination thereof.

[0095] According to some embodiments of the above-described drinkable products, concentrates, and methods, the raw materials may be, but are not limited to, undiluted alcoholic beverages, diluted alcoholic beverages, alcoholic portions of alcoholic beverages, filtered alcoholic beverages, and diluted alcoholic portions of alcoholic beverages. For example, the distillate of an alcoholic beverage having 50% by volume or more ethanol may be diluted to a maximum of 40% by volume ethanol for use as a raw material.

[0096] According to some embodiments of the above-mentioned drinkable products, concentrates and methods, the method further includes the step of measuring the concentration of MeOH, EtOH, EtAc, inherent VOC(20) concentration, inherent median VOC(20), hexanoic acid concentration, phenylethanol concentration, octanoic acid concentration, nonanoic acid concentration, decanoic acid concentration or any combination thereof.

[0097] According to some embodiments of the above-described drinkable products, concentrates, and methods, the method further includes a step of measuring preference for the drinkable products and / or concentrates. According to some embodiments, the step of measuring preference includes measuring at least one characteristic of the drinkable products and / or concentrates, selected from floral, acidity, sourness, fruity, sweetness, green, sulfur, alcohol, or any combination thereof.

[0098] According to some embodiments of the above-described drinkable products, concentrates, and methods, the method further includes the steps of removing ethanol from the alcoholic beverage using any known technique or method, and collecting the aroma-containing fraction. In some embodiments, vacuum distillation is used to remove EtOH.

[0099] In the context of this invention, the term "alcoholic beverage" may be used interchangeably with the terms "adult beverage," "alcoholic beverage," "strong beverage," or simply "beverage," and refers to, but is not limited to, beverages containing ethanol, a medicinal alcohol produced through the fermentation of grains, fruits, or other sugar sources. Non-limiting examples of alcoholic beverages according to one or more of the above and foregoing embodiments include red wine, white wine, rosé wine, champagne, rice wine, and fruit wine. wine, Metaxa, cider, beer, mead, ale, spirits, martini, whiskey, brandy, liquor, rum, cherrybrandy, cognac, Armagnac, calvados, cachaca, arrack, sake, raki, midori, feigling, curacao, schnapps, pisco, tequila, mezcal, grappa, raki, fruit spirits spirit, shochu, soju, Tiswin, Toddy, Tonto, Tuica, Ogogoro, Palinka, Plum Jerkum, Piotin, Pulque, Port, Sherry, Kvass, Chicha, Bijiu, Medronho, pina colada, Ouzo, Aquavit, Absinthe, Gin, or any combination thereof.

[0100] In the context of this invention, the term "aromatic compound" (also known as flavoring agent, aroma agent, fragrance, or flavoring agent) refers to, but is not limited to, compounds or substances having an odor or aroma. These aromatic compounds influence the sensory impression of a beverage, primarily its flavor and aroma. Many aromatic compounds may also be referred to as volatile organic compounds (VOCs) because their volatility is sufficient to enter the olfactory system. Many aromatic compounds in alcoholic beverages are products of, but not limited to, fermentation and / or aging processes. Non-limiting examples of aromatic compounds in the drinkable products, pre-concentrates, concentrates, and raw materials of this invention include geraniol, (Z)-3-hexenal, β-ionone, (R)-linalool, myrcene, nonanal, (R)-α-pinene, ethyl 3-methylbutyrate, hexanal, 1,8-cineole, ethyl acetate, ethyl butyrate, isobutanol, isoamyl acetate, 2-methylbut-1-ol, 3-methylbut-1-ol, ethyl hexanoate, 2-phenylethyl acetate, 2-phenylethanol, or any combination thereof.

[0101] The term "adsorption" is understood to refer to the adhesion of a compound from a liquid or gas, or a solid dissolved in a liquid, to a surface, forming an adsorbate on the surface of an adsorbent. The term adsorbent (also called a binder or adsorbent material) refers to an insoluble material that can bind a certain amount of a compound. Adsorbents are typically characterized as oxygen-containing compounds, carbon-based compounds, or polymer-based compounds.

[0102] According to some embodiments of the above invention, the adsorption step is carried out at a temperature of <50°C. According to some embodiments of the above invention, the adsorption step is carried out at a temperature of <25°C.

[0103] According to some embodiments of the above invention, adsorption is carried out under a pressure of 1-5 bar.

[0104] As used herein, the term "desorption" is understood to refer to the process by which an adsorbed compound is released from a surface into the surrounding vacuum or liquid. Desorption is considered the reverse process of adsorption.

[0105] According to some embodiments of the above invention, the desorption solution is selected from distillate fractions, alcohol fractions, ethanol-water solutions, water, steam, or any combination thereof.

[0106] According to some embodiments of the above invention, the ethanol solution contains at least 50% ethanol or an aqueous ethanol solution. According to some embodiments of the above invention, the desorption solution contains 70% to 96% ethanol or alcohol. According to some embodiments of the above invention, desorption is performed with the ethanol solution at a temperature >10°C. According to some embodiments of the above invention, desorption is performed with the ethanol solution at a temperature >50°C. According to some embodiments of the above invention, desorption is performed with the ethanol solution at a temperature between 50°C and 80°C.

[0107] According to some embodiments of the above invention, desorption is performed with water at temperatures >25°C. According to some embodiments of the above invention, desorption is performed with water at temperatures >50°C. According to some embodiments of the above invention, desorption is performed with water at temperatures between 50°C and 135°C. According to some embodiments of the above invention, the desorption solution is characterized by vapor.

[0108] According to some embodiments of the above invention, the desorption step is carried out under a pressure of <1 bar.

[0109] According to some embodiments of the above invention, each of the columns independently has a length of at least 3000 mm. According to some embodiments of the above invention, the column has a length of 3000 to 7000 mm. The column may have a length of 3200 mm, 3400 mm, 3600 mm, 3800 mm, 4000 mm, 4200 mm, 4400 mm, 4600 mm, 4800 mm, 5000 mm, 5200 mm, 5400 mm, 5600 mm, 5800 mm, 6000 mm, 6200 mm, 6600 mm, or 6800 mm.

[0110] According to some embodiments of the above invention, the width of each column is independently less than 500 mm. According to some embodiments of the above invention, the width of the column is less than 250 mm.

[0111] According to some embodiments of the above invention, each of the columns independently has a width of 5 to 250 mm. According to some embodiments of the above invention, the column has a width of 15 mm, 25 mm, 35 mm, 50 mm, 75 mm, 100 mm, 125 mm, 150 mm, 175 mm, 200 mm, or 225 mm.

[0112] According to some embodiments of the above invention, the column has a volume of at least 5 liters.

[0113] According to some embodiments of the above invention, each column independently has a volume of 5 to 500 liters. According to some embodiments of the above invention, the column has a volume of 10, 15, 25, 50, 75, 100, 125, 150, 175, 200, 250, 300, 350, 400, or 450 liters.

[0114] According to some embodiments of the above invention, each of the columns independently has an aspect ratio of 10:1 to 5000:1. According to some embodiments of the above invention, the columns have aspect ratios of 15:1, 25:1, 50:1, 75:1, 100:1, 150:1, 200:1, 250:1, 500:1, 750:1, 1000:1, 1250:1, 1500:1, 1750:1, 2000:1, 2250:1, 2500:1, 2750:1, 3000:1, 3250:1, 3500:1, 3750:1, 4000:1, 4250:1, 4500:1, 4750:1, or 5000:1.

[0115] As used in this article, the term " Log Pow (also known as P or K OW P refers to the octanol-water partition coefficient of a compound. It is the P partition coefficient of the two-phase system of octanol and water. Log P can be determined experimentally or estimated using various predictive models.

[0116] Procedure A – GC-MS Method for Measuring Methanol Content

[0117] Labelled methanol (methanol-d3-Sigma Aldrich; 343854-1G) is used to measure the methanol content in wine samples containing alcohol and those not containing alcohol.

[0118] In addition, the limit of detection (LOD) was determined.

[0119] Sample preparation for analysis: Mix 1 mL of dichloromethane (HPLC ≥ 99.8%, Sigma Aldrich) and 100 μL of sample in a 1.5 mL glass vial.

[0120] - Add 25 μL of 0.1% methanol-d3 to the mixture as an internal standard.

[0121] The solution was homogenized before injection. Each sample was analyzed twice.

[0122] GC / MS method parameters: Chromatographic separation was performed using a GC-2010 Plus gas chromatograph (Shimadzu, Tokyo, Japan) with an Optima 5 MS Accent column, 30 m × 0.25 mm, 0.25 μm (Macherey-Nagel, Germany). Helium (AirLiquide, France) was used as the carrier gas (purity ≥99.999%) at a flow rate of 1.00 mL / min. The injection temperature was maintained at 230 °C. The sample was injected in split mode (1:25 ratio) using liquid injection. The column temperature was started at 35 °C and maintained for 3 minutes. A GCMS-QP2020 mass spectrometer (Shimadzu, Tokyo, Japan) with a 70 eV electron collision ionization source was used as the detector. The MS source and MS transfer line temperatures were set at 200 °C and 230 °C, respectively. Data acquisition was performed by monitoring ions at m / z of 29, 30, 31, 33, 35, 45, 46, 48, and 49 in SIM mode.

[0123] Data Analysis The peak area of ​​-31 m / z was used for quantification of methanol.

[0124] Limit of detection (LOD) - The LOD of methanol is 0.01% (volume) in alcoholic wines and 0.001% (volume) in de-alcoholized wines.

[0125] Calibration curve The calibration curves were created using standard solutions of 1%, 0.1%, 0.01%, and 0.001% methanol by volume. The equation for the calibration curves is: y = a + bx (where y represents the concentration of the substance and x represents the area of ​​the substance in the chromatogram corrected by the internal standard).

[0126] Procedure B: Determination of volatile organic compound content by headspace-SPME-gas chromatography-mass spectrometry

[0127] Sample preparation (Inherent VOCs): - Preparation of alcoholic wine samples: Mix 9 mL of each sample with 1 mL of distilled water in a 20 mL vial. Add 1 mL to a 20 mL headspace vial and add 3 μL of internal standard 2,3-dimethoxytoluene solution (15.6 ppm). Homogenize the solution before SPME extraction. Analyze each sample twice.

[0128] - Preparation of non-alcoholic wine samples: Mix 9 mL of each sample with 1 mL of ethanol in a 20 mL vial. Add 1 mL of this mixture to a 20 mL headspace vial and add 3 μL of internal standard 2,3-dimethoxytoluene solution (15.6 ppm). Homogenize the solution before SPME extraction. Analyze each sample twice.

[0129] - Alcoholic beverage sample preparation: Dilute each sample to 10% ethanol with distilled water. Place 1 mL in a 20 mL headspace vial and add 3 μL of internal standard 2,3-dimethoxytoluene solution (15.6 ppm). Homogenize the solution before SPME extraction. Analyze each sample twice.

[0130] - Preparation of non-alcoholic beverage samples: Mix 9 mL of each sample with 1 mL of ethanol in a 20 mL vial. Add 1 mL of this mixture to a 20 mL headspace vial, and add the mixture as an internal standard, i.e., 3 μL of 2,3-dimethoxytoluene solution (15.6 ppm). Homogenize the solution before SPME extraction. Analyze each sample twice.

[0131] SPME extraction of volatile compounds: Volatile compound extraction was performed for 20 minutes at 60°C using a solid-phase microextraction (SPME) apparatus (65 μm PDMS / DVB, fused silica 24Ga, manual support, Supelco, Belllefonte, USA). The fibers were treated prior to use as recommended by the commercial company.

[0132] Headspace SPME-Gas Chromatography / Mass Spectrometry Method Parameters: Chromatographic conditions - Chromatographic separation was performed using a GC-2010 Plus gas chromatograph (Shimadzu, Tokyo, Japan) equipped with an Optima FFAP Plus column, 30m × 0.25mm, 0.50μm (Macherey-Nagel, Germany).

[0133] Helium (Air Liquide, France) was used as the carrier gas (purity ≥99.999%) at a flow rate of 1.47 mL / min. The injection temperature was maintained at 230 °C. The sample was manually injected in splitless mode. The column temperature was initially set at 35 °C for 2 minutes, then increased to 235 °C at a rate of 8 °C / min and held at 235 °C for 20 minutes.

[0134] The mass spectrometer detector was a GCMS-QP2020 (Shimadzu, Tokyo, Japan) with a 70 eV electron collision ionization source. The temperatures of the MS source and MS transfer line were set at 200 °C and 230 °C, respectively. The mass range used in the scan mode was 29–250 m / z. The detector detected all compounds within 3.5 to 44.5 minutes.

[0135] Data Analysis: - All volatile organic compounds are monitored in SCAN and reported as peak area TIC, except for internal standards, whose peak areas are reported only for m / z 152.

[0136] - The 30 most abundant volatile compounds were extracted from the chromatogram for further analysis. VOC ppm was calculated as ppm DMOT (m / z 154) equivalent and was correlated with peak area.

[0137] - To calculate VOC(20), the peaks of ethyl acetate (EtAc), ethanol (EtOH), methanol, dichloromethane, and other substances, as well as impurity peaks introduced or generated during sample preparation or sample detection, were ignored, and the median values ​​of the 20 most abundant VOCs were calculated in ppm DMOT (m / z 154) equivalents.

[0138] Example

[0139] In the examples below, if an abbreviation is not defined above, it has its generally accepted meaning.

[0140] Example 1 A method for recovering aromatic compounds from alcoholic beverages.

[0141] The process is based on solid-phase extraction (SPE). Solid-phase extraction is carried out in two stages—adsorption and desorption.

[0142] - First stage: Adsorption—Aromatic compounds are collected and concentrated from the ethanol / aqueous phase on an adsorption bed. The ethanol / aqueous phase is diluted to approximately 15% ABV and pumped through the adsorption bed.

[0143] - Second stage: Desorption - Use a desorbent, such as ethanol / distillate with an ABV higher than 60%, to wash the aromatic compounds off the adsorbent bed.

[0144] The aromatic compound concentrate obtained in the first SPE process is an intermediate product and also the starting material for the second SPE extraction cycle.

[0145] The intermediate product is diluted again with water to an ABV of less than 15% and then processed on a second production unit, the layout of which allows for the processing of small quantities of material.

[0146] Example 2 Preparation of non-alcoholic Casasa.

[0147] Dilute the cassasa wine to 10% ABV. Load the diluted solution onto a resin bed and pump it at room temperature under a pressure of approximately 3 bar.

[0148] Desorption was performed using an ethanol solution at a temperature above 30°C. The adsorption-desorption steps were repeated to obtain a pre-concentrated product.

[0149] The desorption solution (preconcentrate) was diluted to 10% ABV, loaded onto a resin bed, and pumped at a pressure of about 3 bar at room temperature.

[0150] Desorption was performed using an ethanol solution at temperatures above 30°C. A concentrate containing the inherent aromatic compounds of Cachaça was collected. This concentrate was then used to prepare a non-alcoholic Cachaça.

[0151] Example 3 Preparation of non-alcoholic gin.

[0152] Dilute gin (40 ABV) to 10% ABV. Load the diluted solution onto a resin bed and pump it at a pressure of approximately 3 bar at room temperature. Desorption is then performed with an ethanol solution at a temperature above 30°C.

[0153] Repeat the adsorption-desorption steps to obtain a pre-concentrate. Dilute the desorption solution (pre-concentrate) to 10% ABV, load it onto a resin bed, and pump it at a pressure of about 3 bar at room temperature.

[0154] Desorption was performed using an ethanol solution at temperatures above 30°C. A concentrate containing the inherent aromatic compounds of gin was collected.

[0155] Use this concentrate to prepare non-alcoholic gin.

[0156] Table 1: Analytical results of gin containing alcohol (40% ABV) and non-alcoholic gin (prepared according to Example 3, analyzed by procedure B). Peaks are listed in the order of detection.

[0157]

[0158] Example 4 Preparation of non-alcoholic beer.

[0159] Ethanol is removed from beer using vacuum distillation, and the ethanol fraction containing EtOH and volatile organic compounds is collected. The dealcoholized portion is preserved.

[0160] Dilute the ethanol fraction to 10% ABV. Load the diluted solution onto a resin bed and pump it at a pressure of approximately 3 bar at room temperature.

[0161] Desorption was performed using an ethanol solution at a temperature above 30°C. The adsorption-desorption process was repeated to obtain a pre-concentrated product.

[0162] The desorption solution (pre-concentrate) was diluted to 10% ABV, loaded onto a resin bed, and pumped at a pressure of approximately 3 bar at room temperature. Desorption was then carried out with an ethanol solution at a temperature above 30°C. The concentrate containing the inherent aroma compounds of beer was collected.

[0163] Non-alcoholic beer is prepared using concentrates and dealcoholized fractions.

[0164] Example 5 Preparation of non-alcoholic wine.

[0165] Ethanol is removed from wine using vacuum distillation, and the ethanol fraction containing EtOH and volatile organic compounds is collected. The dealcoholized portion is preserved.

[0166] Dilute the ethanol fraction to 10% ABV. Load the diluted solution onto a resin bed and pump it at a pressure of approximately 3 bar at room temperature.

[0167] The wine was diluted to a 10% alcohol concentration. The diluted solution was loaded onto a resin bed and pumped at a pressure of approximately 3 bar at room temperature.

[0168] Desorption was performed using an ethanol solution at a temperature of at least 30°C.

[0169] Repeat the adsorption-desorption steps to obtain a pre-concentrate. Dilute the desorption solution (pre-concentrate) to 10% ABV, load it onto a resin bed, and incubate at room temperature under a pressure of approximately 3 bar.

[0170] Desorption was performed using an ethanol solution at a temperature of at least 30°C.

[0171] Collect concentrates containing the inherent aromatic compounds of wine. Prepare non-alcoholic wine by combining the spice-containing concentrate with the dealcoholized portion.

[0172] This process can be seen in Tables 2 and 3.

[0173] Table 2. Wine: Non-alcoholic wine prepared according to Example 5, analyzed according to procedure B. Peaks are listed in the order of detection.

[0174]

[0175] Table 3: Analysis of relevant substances prepared according to Example 5 using procedure B. Peaks are listed in the order of detection.

[0176]

[0177] Example 6Evaluation of the detection of ethyl acetate in non-alcoholic wines and its impact on aroma

[0178] Based on their ability to describe sensory perceptions, a group of potential participants was identified. Candidates underwent different olfactory stimuli and received training in the use of scales and the development and use of descriptors (profiles), as described in DIN EN ISO 8586:2014-05.

[0179] A group of five people aged 30 to 50 was selected.

[0180] 1. Sensory method description

[0181] The tests were conducted according to ISO 8587, using ethyl acetate as the odor stimulant. Six samples with different concentrations of ethyl acetate (25, 50, 77, 100, and 200 ppm, and a sample without additional ethyl acetate) were prepared from non-alcoholic wine. The samples were presented to the panel members in wine glasses in a random order. After tasting the samples, the panel members were asked to arrange the samples in order of increasing intensity and describe the perceived aroma characteristics.

[0182] 2. Sensory analysis results

[0183] Table 4 shows the prepared samples.

[0184]

[0185] 3. Sensory analysis results

[0186] The panel noted that ethyl acetate concentrations exceeding 50 ppm in non-alcoholic wines are unpleasant and were described by four of the five panel members as having a “gelatinous” off-flavor.

[0187] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. It should also be understood that terms, such as those defined in common dictionaries, should be interpreted as having the same meaning as they do in the context of the specification and claims, and should not be interpreted in an idealized or overly formal sense unless explicitly defined herein. For the sake of brevity and / or clarity, well-known functions or structures may not be described in detail.

[0188] In case of any conflict, the patent specification (including definitions) shall prevail. Furthermore, the materials, methods, and examples are illustrative only and are not necessarily restrictive.

[0189] As described herein, the terms “including,” “comprising,” “possessing,” “having,” and variations thereof mean “including but not limited to.”

[0190] The term "including" means "including and limited to".

[0191] As described herein, the singular forms “an,” “a,” and “the” include the plural unless the context clearly indicates otherwise. For example, the terms “a compound” or “at least one compound” can include a variety of compounds, including mixtures thereof.

[0192] As described herein, the term “and / or” includes any and all possible combinations or one or more of the listed items, as well as no combination when interpreted in the sense of alternative (“or”).

[0193] It should be understood that when an element is referred to as "on top of," "attached to," "connected to," "coupled to," "contacting," etc., another element may be directly located on, attached to, connected to, coupled to, and / or in contact with another element, or there may be intermediate elements present. Conversely, when an element is referred to, for example, "directly on another element," "directly attached to it," "directly connected to it," "directly coupled to," or "directly in contact with" another element, there are no intermediate elements. Those skilled in the art should also understand that when referring to a structure or feature disposed "adjacent" to another feature, that structure or feature may have portions that overlap with or are located below the adjacent feature.

[0194] It should be understood that although the terms first, second, etc., may be used herein to describe various elements, components, regions, layers, and / or parts, these elements, components, regions, layers, and / or parts should not be limited by these terms. Rather, these terms are used only to distinguish one element, component, region, layer, and / or part from another.

[0195] Throughout this invention, various embodiments of the invention may be presented in the form of ranges. It should be understood that the range format is merely for convenience and brevity and should not be construed as an immutable limitation on the scope of the invention. Therefore, the range description should be considered as having specifically disclosed all possible subranges and individual numerical values ​​within that range. For example, a description of a range such as 1 to 6 should be considered as having specifically disclosed subranges such as 1 to 3, 1 to 4, 1 to 5, 2 to 4, 2 to 6, 3 to 6, etc., and individual numbers within that range, such as 1, 2, 3, 4, 5, and 6. This applies to any range width.

[0196] Whenever this document specifies a range of numbers, it means any referenced number (fraction or integer) included within the specified range. The phrases “range between the first and second indicators” and “range from the first to the second indicator” are used interchangeably in this document and mean including the first and second indicators as well as all fractions and integers in between.

[0197] Whenever the term “about” is used, it is intended to refer to a measurable value, such as quantity, duration, etc., and is intended to include variations of ±20%, ±10%, ±5%, ±1%, or ±0.1% of a particular value, as such variations are appropriate for implementing the disclosed method.

[0198] Whenever the terms "multiple" and "amount" are used, it means, for example, "multiple" or "two or more". The terms "multiple" or "amount" may be used throughout the specification to describe two or more components, devices, elements, units, parameters, etc. The term "set" as used herein may include one or more items. Unless explicitly stated otherwise, the method embodiments described herein are not limited to a particular order or sequence. Furthermore, some of the described method embodiments or elements thereof may occur or be performed simultaneously, at the same point in time, or concurrently.

[0199] As described herein, the term “method” refers to the manner, means, techniques and procedures used to accomplish a given task, including but not limited to those manner, means, techniques and procedures known to practitioners in the fields of chemistry, biology, biochemistry and veterinary medicine, or easily developed from known manner, means, techniques and procedures.

[0200] For clarity, certain features of the invention described in the context of individual embodiments may also be provided in combination in a single embodiment. Conversely, for brevity, various features of the invention described in the context of individual embodiments may also be provided individually, or in any suitable sub-combination, or appropriately provided in any other described embodiments of the invention. Certain features described in the context of various embodiments should not be considered essential features of those embodiments unless the embodiment would not function without these elements.

[0201] All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety to provide a more comprehensive description of the current state of the art to which this invention pertains. In case of any conflict, the patent specification (including definitions) shall prevail. Furthermore, materials, methods, and examples are illustrative only and not restrictive. Throughout this invention, references have been made to various publications, published patent applications, and published patents.

[0202] Those skilled in the art will understand that the present invention is not limited to what has been specifically shown and described above. Rather, the scope of the invention is defined by the appended claims and includes combinations and sub-combinations of the various features described above, as well as variations and modifications thereof, which will occur to those skilled in the art upon reading the foregoing description. While certain features of the invention have been described and illustrated herein, many modifications, substitutions, alterations, and equivalents will occur to those skilled in the art. Therefore, it should be understood that the appended claims are intended to cover all such modifications and variations falling within the true spirit of the invention. Various embodiments have been presented. Each of these embodiments may, of course, include features derived from other embodiments, and embodiments not specifically described may include the various features described herein.

[0203] For clarity, certain features of the invention described in the context of individual embodiments may also be provided in combination in a single embodiment. Conversely, for brevity, various features of the invention described in the context of individual embodiments may also be provided individually, or in any suitable sub-combination, or appropriately provided in any other described embodiments of the invention. Certain features described in the context of various embodiments should not be considered essential features of those embodiments unless the embodiment would not function without these elements.

Claims

1. A drinkable product prepared from an alcoholic beverage containing 0.045% by volume or less ethanol, characterized in that, The drinkable product contains a certain amount of inherent volatile organic compounds (VOCs); and the inherent VOCs include a variety of inherent aromatic compounds; and the MeOH content in the drinkable product satisfies at least one of the following: e. When measured using procedure A, the level is below detection threshold; f. Less than 0.01% by volume; and, When measured by procedure B, the ratio of the amount of EtAc in the drinkable product to the intrinsic median VOC (20) is 1:0.2 to 1:

300.

2. The drinkable product according to claim 1, wherein, The ratio of EtAc to the intrinsic median VOC(20) is 1:0.5 to 1:

200.

3. The drinkable product according to claim 1 or 2, wherein, The ratio of EtAc to the intrinsic median VOC(20) is 1:1 to 1:

125.

4. The drinkable product according to any one of claims 1 to 3, wherein, The ratio of EtAc to the intrinsic median VOC(20) is 1:3 to 1:

50.

5. The drinkable product according to any one of claims 1 to 4, wherein, The ratio of EtAc to the intrinsic median VOC(20) is 1:4 to 1:

25.

6. A drinkable product prepared from an alcoholic beverage containing 0.045% by volume or less ethanol, characterized in that, The drinkable product contains a certain amount of inherent volatile organic compounds (VOCs); and wherein the inherent VOCs include a variety of inherent aromatic compounds; and wherein, when measured by procedure A, the MeOH content in the drinkable product is below the detection level and / or less than 0.01% by volume; and wherein the drinkable product is characterized by satisfying at least one of the following:

1. The ratio of EtAc to hexanoic acid is 1:0.02 to 1:250; 2. The ratio of EtAc to phenylethanol is 1:0.01 to 1:245; 3. The ratio of EtAc to octanoic acid is 1:0.3 to 1:300; 4. The ratio of EtAc to nonanoic acid is 1:0.1 to 1:100; and, 5. The ratio of EtAc to decanoic acid is 1:0.3 to 1:320; The amounts of EtAc and VOCs were measured using procedure B.

7. The drinkable product according to any one of claims 1 to 6, wherein, The median VOC(20) is represented by the median of the 20 most abundant volatile organic compounds in the sample detected by procedure A.

8. The drinkable product according to any one of claims 1 to 6, wherein, The amount of inherent total VOC (20) in the drinkable product is at least 100 ppm.

9. The drinkable product according to any one of claims 1 to 8, wherein, The amount of inherent total VOC (20) in the drinkable product is at least 150 ppm.

10. The drinkable product according to any one of claims 1 to 9, having at least 10 inherent VOCs at a concentration of at least 1 ppm.

11. The drinkable product according to any one of claims 1 to 10, having at least 10 inherent VOCs at a concentration of at least 2 ppm.

12. The drinkable product according to any one of claims 1 to 11, having at least 20 inherent VOCs at a concentration of at least 1 ppm.

13. The drinkable product according to any one of claims 1 to 12, wherein, The log Pow value of at least a portion of the inherent aromatic compounds in the inherent VOCs of the drinkable product is between 0.7 and 1.

35.

14. The drinkable product according to any one of claims 1 to 12, wherein, The log Pow value of at least a portion of the inherent aromatic compounds in the inherent VOCs of the drinkable product is between 0.7 and 3.

5.

15. The drinkable product according to any one of claims 1 to 13, wherein, The inherent aromatic compounds in the inherent VOC include at least one of the following: geraniol, (Z)-3-hexenal, β-ionone, (R)-linalool, myrcene, nonanal, (R)-α-pinene, ethyl 3-methylbutyrate, hexanal, 1,8-cineole, ethyl acetate, ethyl butyrate, isobutanol, isoamyl acetate, 2-methylbut-1-ol, 3-methylbut-1-ol, ethyl hexanoate, 2-phenylethyl acetate, 2-phenylethanol, or any combination thereof.

16. The drinkable product according to any one of claims 1 to 15, comprising 0.001% by volume or less ethanol.

17. The drinkable product according to any one of claims 1 to 16, comprising 0.0045% by volume or less ethanol.

18. The drinkable product according to any one of claims 1 to 17, which is made from a fermented alcoholic beverage.

19. The drinkable product according to claim 18, wherein, The alcoholic beverages are selected from red wine, white wine, rosé wine, sparkling wine, champagne, fruit wine, rice wine and Metasar.

20. The drinkable product according to any one of claims 1 to 19, wherein, The alcoholic beverages are selected from the following categories: cider, beer, mead, ale, spirits, martini, whiskey, brandy, cognac, Armagnac, spirits, rum, cherry brandy, Calvados, Casasa, arugula, sake, lac, midori, liqueur, curacao, gin, pisco, tequila, mezcal, grappa, lac, fruit spirits, shochu, shochu, tisse, geswin, gestodi, tontau, plum brandy, oggoro, palinca, plum jerome, piotin, bourgai, port, sherry, kvass, chicha, gem, meadonio, or any combination thereof.

21. The drinkable product according to any one of claims 1 to 20, wherein, The inherent VOC comprises at least 70% of the various inherent aromatic compounds found in the alcoholic beverage used to make the drinkable product.

22. The drinkable product according to any one of claims 1 to 21, wherein, The inherent VOC comprises at least 80% of the various inherent aromatic compounds found in the alcoholic beverage used to make the drinkable product.

23. The drinkable product according to any one of claims 1 to 22, wherein, The inherent VOC comprises at least 90% of the various inherent aromatic compounds found in the alcoholic beverage used to make the drinkable product.

24. The drinkable product according to any one of claims 1 to 23, characterized in that, It contains no added flavorings, colorings, and / or seasonings.

25. A drinkable product prepared from an alcoholic beverage containing 0.045% by volume or less ethanol, characterized in that, The drinkable product contains a certain amount of inherent volatile organic compounds (VOCs); and the inherent VOCs include a variety of inherent aromatic compounds; and the MeOH content in the drinkable product satisfies at least one of the following:

1. When measured using procedure A, the reading is below the detection level; 2. Less than 0.01% by volume; and, The inherent VOC comprises at least 70% of the various inherent aromatic compounds found in alcoholic beverages made into drinkable products.

26. The drinkable product according to claim 25, wherein, The inherent VOC comprises at least 80% of the various inherent aromatic compounds found in the alcoholic beverage used to make the drinkable product.

27. The drinkable product according to claim 25 or 26, wherein, The inherent VOC comprises at least 90% of the various inherent aromatic compounds found in the alcoholic beverage used to make the drinkable product.

28. The drinkable product according to any one of claims 25 to 27, characterized in that, It contains no added flavorings, colorings, and / or seasonings.

29. The drinkable product according to any one of claims 25 to 28, wherein, The alcoholic beverages are selected from red wine, white wine, rosé wine, champagne, rice wine, fruit wine, Metasar, cider, beer, mead, ale, spirits, martini, whiskey, brandy, cognac, Armagnac, spirits, rum, cherry brandy, Calvados, Casasa, arugula, sake, lac, midori, liqueur, curacao, gin, Pisco, tequila, mezcal, grappa, lac, fruit spirits, shochu, distilled spirits, tequila, tequila, tontau, plum brandy, oogoro, palinca, plum jerome, piotin, bourgai, port, sherry, kvass, chicha, gem spirits, Medronio, ouzo, aquavit, vermouth, gin, or any combination thereof.

30. The drinkable product according to claim 29, wherein, The alcoholic beverages are selected from red wine, white wine, rosé wine and champagne.

31. The drinkable product according to any one of claims 25 to 30, wherein, The amount of inherent VOCs in the drinkable product is at least 100 ppm.

32. The drinkable product according to any one of claims 25 to 31, wherein, The amount of inherent VOCs in the drinkable product is at least 150 ppm.

33. The drinkable article according to any one of claims 25 to 32, having at least 10 inherent VOCs at a concentration of at least 1 ppm.

34. The drinkable article according to any one of claims 25 to 33, having at least 10 inherent VOCs at a concentration of at least 2 ppm.

35. The drinkable article according to any one of claims 25 to 34, having at least 20 inherent VOCs at a concentration of at least 1 ppm.

36. The drinkable product according to any one of claims 25 to 35, wherein, The log Pow value of at least a portion of the inherent aromatic compounds in the inherent VOCs of the drinkable product is between 0.7 and 1.

35.

37. The drinkable product according to any one of claims 25 to 36, wherein, The log Pow value of at least a portion of the inherent aromatic compounds in the inherent VOCs of the drinkable product is between 0.7 and 3.

5.

38. The drinkable product according to any one of claims 25 to 37, wherein, The inherent aromatic compounds in the inherent VOC include at least one of the following: geraniol, (Z)-3-hexenal, β-ionone, (R)-linalool, myrcene, nonanal, (R)-α-pinene, ethyl 3-methylbutyrate, hexanal, 1,8-cineole, ethyl acetate, ethyl butyrate, isobutanol, isoamyl acetate, 2-methylbut-1-ol, 3-methylbut-1-ol, ethyl hexanoate, 2-phenylethyl acetate, 2-phenylethanol, or any combination thereof.

39. A method for preparing a drinkable article as described in any one of claims 1 to 38, the method comprising:

1. To recover at least most of the various inherent aromatic compounds from alcoholic beverages containing VOCs; and, 2. To prepare a drinkable product containing a certain amount of VOC, wherein the VOC includes a variety of inherent aromatic compounds; The step of recovering multiple aromatic compounds from an alcoholic beverage includes at least a pre-concentration and a concentration step; wherein the pre-concentration step includes preparing a pre-concentrate containing multiple aromatic compounds from raw materials derived from the alcoholic beverage; and wherein the concentration step includes preparing a concentrate containing multiple aromatic compounds from the pre-concentrate; and wherein each of the pre-concentration and concentration steps independently includes at least one cycle: adsorption on at least one column loaded with an adsorbent, the adsorbent binding at least most of the multiple inherent aromatic compounds; and desorption of the multiple inherent aromatic compounds from the at least one column with a desorbent.

40. A method for preparing a drinkable article as described in any one of claims 1 to 38, comprising the following steps:

1. Provide a raw material having a maximum of 50% by volume ethanol, wherein the raw material is derived from an alcoholic beverage and contains a certain amount of VOCs, the VOCs comprising a variety of inherent aromatic compounds of the alcoholic beverage; 2. Preparation of a concentrate containing a variety of inherent aromatic compounds; and, 3. Obtain a drinkable product containing a certain amount of VOC from the concentrate of step b, wherein the VOC contains a variety of inherent aromatic compounds.

41. The method of claim 39 or 40, further comprising the step of measuring the amounts of VOC and EtAc by procedure B to determine the ratio of the amounts of EtAc to VOC.

42. The method according to any one of claims 39 to 40, further comprising measuring the MeOH concentration in the drinkable product by procedure A.

43. The method according to any one of claims 39 to 42, wherein, The raw materials are selected from undiluted alcoholic beverages, diluted alcoholic beverages, alcohol-containing portions of alcoholic beverages, filtered alcoholic beverages, diluted alcohol-containing portions of alcoholic beverages, or any combination thereof.

44. The method according to any one of claims 39 to 43, wherein, The alcoholic beverages are selected from red wine, white wine, rosé wine, champagne, rice wine, fruit wine, Metasar, cider, beer, mead, ale, spirits, martini, whiskey, brandy, spirits, rum, cherry brandy, Calvados, Caesarsa, Ale, sake, lac, Midori, liqueur, Curacao, gin, cognac, Armagnac, Pisco, tequila, mezcal, grappa, lac, fruit spirits, shochu, distilled spirits, tisse, tisse, tontau, plum brandy, oogoro, palinca, plum jerome, piotin, bourgai, port, sherry, kvass, chicha, gem spirits, Medronio, Coconut, ouzo, Aquavit, vermouth, gin, or any combination thereof.

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