WO2021004638A1

WO2021004638A1 - Method for the recovery or enrichment of flavours of fragrances from an aroma-laden gas phase and an aroma concentrate

Info

Publication number: WO2021004638A1
Application number: PCT/EP2019/068721
Authority: WO
Inventors: Stefan Brennecke; Katharina Reichelt; Gerhard Krammer
Original assignee: Symrise Ag
Priority date: 2019-07-11
Filing date: 2019-07-11
Publication date: 2021-01-14
Also published as: WO2021005239A1; EP3996525A1

Abstract

The invention relates to a method for the recovery or enrichment of flavours and/or fragrances from an aroma-laden gas phase. The invention also relates to a method for producing an aroma concentrate, an eluate enriched with a flavouring and/or fragrance, or an aroma concentrate that can be produced according to the claimed methods, to the use of said type of enriched eluate or said type of aroma concentrate and products comprising the claimed enriched eluate or the claimed aroma concentrate.

Description

Process for the recovery or enrichment of flavors or fragrances from an aroma-loading

Gas phase and an aroma concentrate

Field of invention

The present invention relates to a method for the recovery or enrichment of flavors and / or fragrances from an aroma-laden gas phase, a method for the production of an aroma concentrate, an enriched with a taste and / or fragrance eluate or an aroma concentrate, produced according to the Process according to the invention, the use of such an enriched eluate or such an aroma concentrate, as well as products which comprise the enriched eluate according to the invention or the aroma concentrate according to the invention.

State of the art

The ever increasing demand for products in the food and beverage sector, in cosmetics, in pharmacy and in the animal feed sector, etc. increases at the same time the need for flavors or fragrances or aromas.

In the production of food, especially in the thermal processing of food, there are industrially significant amounts of aroma-laden, smell- and taste-intensive gas or vapor phases that are concentrated or as a concentrate of the same foods from which they were generated to reconstitute the aroma to be added again.

During the thermal treatment or the evaporation process, liquid evaporates from the starting product. Not inconsiderable amounts, in particular, of volatile flavors and / or fragrances, pass into the gas or vapor phase. Such gas phases with valuable flavors and / or fragrances arise, for example, when drying tea, fruit, vegetables, herbs, spices, flowers, when concentrating, for example, juices, when producing fruit preparations, etc.

The recovery and enrichment of the flavors and / or fragrances contained in such gas phases usually takes place from an aroma-laden aqueous phase which is obtained by condensation of the gas phase.

Methods for the recovery or enrichment or concentration of flavors and / or fragrances from an aqueous aroma phase are well known in the art and include, for example, distillation, membrane processes, adsorption processes, extraction with supercritical carbon dioxide or liquid-liquid extraction.

A disadvantage of the distillation process is that despite the use of gentle process parameters such as the use of vacuum to reduce the vapor pressures from the volatile components at temperatures of> 30 ° C, disturbing taste or fragrance components can be formed or desired taste or Fragrance components can be broken down. During the distillation, for example, the thermal load on the aqueous aroma phase can result in undesirable cooking notes, which means that these methods of concentration can only be used to a limited extent, since they do not lead to an authentic taste profile.

The adsorptive enrichment or concentration of flavors and / or fragrances from an aroma-laden aqueous phase is described, for example, in EP 2 075 321 A1. In this process, the aqueous aroma phase is passed through an adsorption column and the flavor and / or fragrance substances absorbed on the adsorption material are desorbed by means of a solvent. In addition, the aromatic aqueous solutions are not a chemically uniform substance, but are composed of a large number of different chemical components, which only give the sensory result of the natural flavor of a food in their entirety. The processes for recovery or enrichment known in the prior art often lead to an undesired fractionation of the mixture of the flavors and / or fragrances.

Another disadvantage of the above-described methods from the prior art is that they are designed for aqueous aroma phases, but not for aroma-laden gas or vapor phases. The aroma-laden gas or vapor phases must therefore first be condensed before the distillative or adsorptive enrichment, an additional process step in which on the one hand energy has to be used and on the other hand losses of valuable flavors and / or fragrances, for example through oxidation of the flavors and / or fragrances occur, whereby otherwise non-occurring aroma components arise, one or more characteristic compound (s) (impact compounds) are lost or a concentration shift takes place between the individual aroma components, which can lead to off-flavors.

In the storage of such condensates, further losses of the valuable flavors and / or fragrances, in particular volatile flavors and / or fragrances, can occur through evaporation, through oxidation or through microorganisms, which in turn leads to negative impairment or impairment. Shift in taste or smell profile leads.

Due to the high acquisition costs for corresponding capacitors, aroma-laden gas or vapor phases are often not used and are simply discarded. The recovery or enrichment of valuable flavors and / or fragrances directly from an aroma-laden gas phase is therefore a technological challenge.

The aim of the present invention was therefore to provide a method in which valuable flavors and / or fragrances with fewer losses or even without losses of the valuable flavors and / or smells, and without degradation or change in the taste and / or odorous substances, and thus can be recovered or enriched or concentrated while largely retaining their original composition without additional expenditure of energy.

Furthermore, the condensation apparatuses which are customary in the prior art and which are connected upstream of the adsorption columns should be avoided, since their acquisition costs are high.

In addition, the usual in the prior art losses of flavors and / or fragrances, in particular volatile flavors and / or fragrances, which can occur during storage of the condensates, for example by evaporation, by oxidation or by microorganisms, be avoided.

Summary of the invention

[0018] The present problem is solved by the subjects of the independent claims. Preferred configurations emerge from the wording of the dependent claims and the following description.

In a first aspect, the present invention relates to a method for the recovery or enrichment of one or more flavor and / or fragrance (s), consisting of or comprising the following steps: (la) providing an aroma-laden gas or vapor phase, comprising at least one flavor and / or fragrance;

(l b) providing and conditioning an adsorption material in an adsorption device;

(l c) passing the aroma-laden gas or vapor phase from step (1 a) through the adsorption device with the adsorption material from step (1 b), so that the at least one flavor and / or fragrance is adsorbed on the adsorption material;

(l d) providing at least one food-safe organic solvent or a solvent mixture which comprises at least one food-safe organic solvent, or at least one food-safe organic mixture which is suitable as a solvent, or a substance mixture which comprises at least one food-safe organic substance with solvent properties;

(le) Elution of the at least one flavor and / or fragrance from the adsorption material from step (1 c) with the solvent or solvent mixture or the mixture which is suitable as a solvent or the mixture of substances with solvent properties from step (1 d) with retention an eluate enriched with the at least one flavor and / or fragrance;

and optional

(l f) Concentration of the eluate obtained from step (1 e) while obtaining an aroma phase.

In a second aspect, the present invention relates to a method for

Manufacture of a flavor concentrate consisting of or comprising the following

Steps:

(2a) providing an aroma-loading gas or vapor phase, comprising at least one flavor and / or fragrance;

(2b) providing and conditioning an adsorption material in an adsorption device; (2c) passing the aroma-laden gas or vapor phase from step (2a) through the adsorption device with adsorption material from step (2b), so that the at least one flavor and / or fragrance is adsorbed on the adsorption material;

(2d) providing at least one food-safe organic solvent or a solvent mixture which comprises at least one food-safe organic solvent, or at least one food-safe organic mixture which is suitable as a solvent, or a substance mixture which comprises at least one food-safe organic substance with solvent properties;

(2e) Elution of the at least one flavor and / or fragrance from the adsorption material from step (2c) with the solvent or solvent mixture or the mixture which is suitable as a solvent, or the mixture of substances with solvent properties from step (2d) to obtain a with the at least one flavor and / or fragrance enriched eluate; and

(2f) Concentration of the eluate obtained from step (2e) to obtain an aroma concentrate.

Another object of the present invention relates to an eluate, enriched with the at least one flavor and / or fragrance, or an aroma concentrate, which can be produced by the above inventive method.

Another aspect of the present invention relates to the use of the enriched eluate or the aroma concentrate for flavoring or for reconstituting the aroma of food, luxury goods, beverage products, semi-finished products, oral hygiene products, cosmetics, pharmaceutical products or animal foods or for the production of food, Luxury foods, beverage products, semi-finished products, oral hygiene products, cosmetics, pharmaceutical products or animal food. Ultimately, the present invention relates to food, luxury goods, beverage products, semi-finished products, oral hygiene products, cosmetics, pharmaceutical products or animal foods which comprise the enriched eluate or the aroma concentrate.

Surprisingly, it was found in the context of the present invention that the combination of direct application of an aroma-laden gas or vapor phase to the adsorption device and adsorption on a sorbent and subsequent desorption solved the aforementioned difficulties of the prior art and the valuable taste and / or flavorings can be enriched without the need for an additional condensation step. The direct application of the gas or vapor phase to the adsorption device also enables flavors and / or fragrances, in particular volatile flavors and / or fragrances, to be absorbed more quickly, ie without a time delay, and better on the adsorption material, so that no oxidation can take place and thus losses of valuable flavors and / or fragrances can occur, which usually leads to a change in the sensory profile.

Detailed description of the invention

A first object of the present invention relates to a method for the recovery or enrichment of one or more flavor and / or fragrance (s), consisting of or comprising the following steps:

(l a) providing an aroma-laden gas or vapor phase, comprising at least one flavor and / or fragrance;

(lc) passing the aroma-laden gas or vapor phase from step (1 a) through the adsorption device with the adsorption material from step (1 b), so that the at least one flavor and / or fragrance is adsorbed on the adsorption material; (ld) providing at least one food-safe organic solvent or a solvent mixture which comprises at least one food-safe organic solvent, or at least one food-safe organic mixture which is suitable as a solvent, or a substance mixture which comprises at least one food-safe organic substance with solvent properties;

(le) Elution of the at least one flavor and / or fragrance from the adsorption material from step (1 c) with the solvent or solvent mixture or the mixture which is suitable as a solvent or the mixture of substances with solvent properties from step (1 d) with retention an eluate enriched with the at least one flavor and / or fragrance; and optional

In a second aspect, the present invention relates to a method for

Manufacture of a flavor concentrate consisting of or comprising the following

Steps:

(2b) providing and conditioning an adsorption material in an adsorption device;

(2c) passing the aroma-laden gas or vapor phase from step (2a) through the adsorption device with adsorption material from step (2b), so that the at least one flavor and / or fragrance is adsorbed on the adsorption material;

(2d) Provision of at least one food-safe organic solvent or a solvent mixture that comprises at least one food-safe organic solvent, or of at least one food-safe organic mixture that is suitable as a solvent, or a mixture of substances that contains at least one includes food-grade organic material with solvent properties;

(2e) Elution of the at least one flavor and / or fragrance from the adsorption material from step (2c) with the solvent or solvent mixture or the mixture which is suitable as a solvent or the mixture of substances with solvent properties from step (2d) to obtain an eluate ; and

The method steps (1 a) to (1 e) of the method for the recovery or enrichment of one or more flavors and / or fragrances according to the first aspect of the present invention correspond to the method steps (2a) to (2e) of the method according to the second aspect of the present invention or are identical to these. The following description is therefore as regards the technical features of process steps (1 a) to (1 e) of the process for the recovery or enrichment of one or more flavorings and / or fragrances according to the first aspect of the present invention and their preferred variants, equally valid for the technical features of method steps (2a) to (2e) of the method according to the second aspect of the present invention and their preferred variants and vice versa. The following detailed description, in particular the description of method steps (1 a) to (1 e) on the one hand and (2a) to (2e) on the other hand, as well as preferred configurations therefore apply both to the method according to the invention according to the first aspect and to the method according to the invention according to the second aspect, unless otherwise indicated.

In the method according to the present invention according to the first and / or second aspect, a recovery or enrichment of one or more flavor and / or fragrance (s) takes place directly from a gas or vapor phase, which comprises at least one flavor and / or fragrance, as starting material.

For the recovery or enrichment of one or more flavor and / or fragrance (s) is in a first step (1a) of the method according to the first aspect or step (2a) of the method according to the invention according to the second aspect therefore an aroma-laden gas or vapor phase is provided which comprises at least one flavor and / or fragrance.

In the context of the present invention, a gas or vapor phase is understood to mean a gas or a vapor which is produced by evaporation or evaporation of liquid. Gas is a substance that has changed from its usual, mostly liquid physical state to a usually invisible gaseous state. During evaporation, a substance changes from a liquid to a gaseous state without reaching the boiling point. Evaporation occurs when the gas phase above the liquid is not yet saturated with vapor. Vapor is a gas that is generally still in contact with the liquid phase from which it emerged through evaporation. This is a visible moist haze, i.e. a visible mixture of air and the finest liquid droplets, such as is formed, for example, when water vapor condenses, also known as an aerosol. Both terms “gas phase” and “vapor phase” are used equally alongside one another in the present invention.

Such gas or vapor phases occur during the production or processing of food, for example during a thermal treatment, for example during drying, or an evaporation and / or evaporation process in which / which predominantly evaporates and / or evaporates water and not inconsiderable amounts of particularly volatile taste and / or Fragrances pass into the vapor phase. This creates aroma-laden gas or vapor phases.

Such aroma-laden gas or vapor phases with valuable flavors and / or fragrances arise, for example, when drying tea, fruit, vegetables, herbs, spices, flowers, leaves, when concentrating food, such as fruit or vegetable juices the production of fruit preparations, etc.

The gas or vapor phase, which is used in the inventive method according to the first and / or second aspect as a starting material, is preferably a gas or vapor phase that is used in the drying of fruits, vegetables, herbs, spices or flowers or occurs in the thermal treatment of food, for example in the concentration of fruit or vegetable juices, in the production of fruit preparations, etc., and which contains valuable flavors and / or fragrances in different concentrations.

In the method according to the invention according to the first and / or second aspect, the fruit is preferably selected from the group consisting of citrus fruits, in particular bergamot, bitter orange, lemon, orange, orange, mandarin, clementine, grapefruit, grapefruit, lime, Lime, kumquat, tangor and tangelo, watermelon, net melon, honeydew melon, kiwi, papaya, avocado, acerola, bearberry, blackberry, blueberry, boysenberry, cherry, Virginia black cherry, cloudberry, red, white and black currant, josta, date, dewberry ( Rubus caesius), elderberry, grape, gooseberry, huckleberry, loganberry, olallieberry, mulberry, raisin, plain berry, prairie berry, lingonberry, raspberry, pear, splendid raspberry (Rubus spectabilis), sea buckthorn fruit, sloe fruit, strawberry, white cinnamon raspberry (Rubus parviflorus), wolfberry, grape, blueberry, apple, rhubarb, passion fruit, plum, e.g. plum, mirabelle plum, apricot, nectarine, quince, kiwi , Star fruit, lychee, pineapple, guava, papaya, passion fruit, mango and peach. In the inventive method according to the first and / or second aspect, the vegetable is preferably selected from the group consisting of carrot, parsnip, parsley root, paprika, pepperoni, zucchini, pumpkin, tomato, shallot, yellow, white and red Kitchen onions, yellow leek, spring onions, garlic, green and white asparagus, green beans, flat peas, green peas, eggplant, cucumber, radishes, radish, yellow and beetroot, beetroot, red cabbage, white cabbage, pointed cabbage, kale, cauliflower, savoy cabbage, broccoli , Sauerkraut, kimchi, celery sticks and tuber, vegetable fennel, Swiss chard and spinach.

In the method according to the invention according to the first aspect and / or the method according to the invention according to the second aspect, the herbs are preferably selected from the group consisting of basil, fennel, coriander, caraway, cumin, dill, savory, lemon balm, lavender , Marjoram, oregano, rosemary, sage, clary sage, peppermint, curly and other mints, parsley, chives, chives, thyme, curry herbs, pimples, lovage and garlic.

The term “spice” includes, by definition, fresh, dried and / or fermented plant parts, such as leaves (dried herbs, bay leaves, kaffir lime leaves), buds, blossoms or flower parts (saffron, cloves, capers), bark (cinnamon), plant roots (Horseradish, wasabi, galangal), rhizomes (ginger, turmeric), onions (kitchen onions, garlic) and fruits or seeds (nutmeg, white, green and black pepper, allspice, rose, cayenne and sweet paprika, juniper berries, vanilla, caraway seeds , Cumin, dill, anise, star anise).

In the method according to the invention according to the first and / or second aspect, the freshly harvested parts of herbs are selected from the group consisting of vanilla pods, tea leaves, preferably Camellia ssp., Particularly preferably Camellia sinensis, clove buds, tonka beans, pepper fruits, coffee beans, Cocoa tree seeds, saffron threads, ginger, turmeric, capers, anise, nutmeg and paprika. In the method according to the invention according to the first and / or second aspect, the flowers are selected from the group consisting of rose flowers, citrus flowers, bergamot flowers, orange flowers, chamomile flowers, hibiscus flowers, lavender flowers, cornflower flowers, marigold flowers, geranium flowers, violet flowers, capuchin flowers, Fuchsia flowers and carnation flowers.

In the method according to the invention according to the first and / or second aspect is most preferably an aroma-laden gas or vapor phase, which is even more preferred in the roasting of coffee or in the drying of tea, preferably tea from the species Camellia sinensis from fermented black tea, partially fermented oolong tea or (largely) unfermented green, white or yellow tea.

In the processes listed above, namely in the thermal treatment or an evaporation and / or evaporation process, temperatures in the range from 70 to 90 ° C are preferably used, in which predominantly water is evaporated or evaporated from the starting material.

Most preferred in the process according to the invention is therefore an aqueous gas or vapor phase which has a relative humidity of 40 to 100%, preferably at least 60%, even more preferably at least 70% and most preferably at least 75% .

In the thermal treatment or the evaporation and / or evaporation process, in which / which predominantly water is evaporated, not inconsiderable amounts, especially volatile, flavors and / or fragrances, the type and composition of which depend on the starting material, go in the gas or vapor phase over. This creates an aroma-laden aqueous gas or vapor phase which is used as starting material in the method according to the invention according to the first or second aspect. The term “aroma-laden” as used in the context of the present invention is to be understood broadly and means that the gas or vapor phase comprises at least one flavor and / or fragrance. The term “aroma store” thus equally includes a flavor and / or a fragrance.

The term "aroma store" also includes a single flavor or fragrance or multiple flavors or fragrances or combinations thereof or an aroma or fragrance that / the / that in the food or in the plant from which the gas or Vapor phase is generated is included.

The combination of a flavor and / or fragrance can comprise any number, i.e. two, three, four, five or even many more flavors and / or fragrances.

The term "at least one flavor or fragrance" means in the context of the present invention that the gas or vapor phase either a single flavor and / or fragrance or a plurality, ie two, three, four, five or even far may include more, different flavor and / or fragrance components, depending on the composition of the starting material from which the gas or vapor phase is generated.

Usually, aromas or fragrances in foods or plants are not present in binary or ternary mixtures, but as a component of sophisticated complex mixtures that contain two, three, four, five, ten, but preferably a much higher number of aroma or Can contain fragrances, sometimes in very small quantities, in order to produce a particularly rounded aroma or fragrance profile.

Depending on the flavors or fragrances that are contained in the starting material from which the gas or vapor phase is generated, in a preferred development of the present invention includes Gas or vapor phase therefore one or an arbitrarily large number of flavor or fragrance (s) which is / are selected from the group formed by: (1) hydrocarbons; (2) aliphatic alcohols; (3) aliphatic aldehydes and their acetals; (4) aliphatic ketones and their oximes; (5) aliphatic sulfur-containing compounds; (6) aliphatic nitriles; (7) esters of aliphatic carboxylic acids; (8) acyclic terpene alcohols; (9) acyclic terpene aldehydes and ketones; (10) cyclic terpene alcohols; (1 1) cyclic terpene aldehydes and ketones; (12) cyclic alcohols; (13) cycloaliphatic alcohols; (14) cyclic and cycloaliphatic ethers; (15) cyclic and macrocyclic ketones; (16) cycloaliphatic aldehydes; (17) cycloaliphatic ketones; (18) esters of cyclic alcohols; (19) esters of cycloaliphatic alcohols; (20) esters of cycloaliphatic carboxylic acids; (21) araliphatic alcohols; (22) esters of araliphatic alcohols and aliphatic carboxylic acids; (23) araliphatic ethers; (24) aromatic and araliphatic aldehydes; (25) aromatic and araliphatic ketones; (26) aromatic and araliphatic carboxylic acids and their esters; (27) nitrogen-containing aromatic compounds; (28) phenols, phenyl ethers, and phenyl esters; (29) heterocyclic compounds; (30) lactones; as well as their mixtures.

The flavors or fragrances are preferably those that are listed z. B. in “S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, N. J., 1969, self-published "," H. Surburg and J. Panten, Common Fragrance and Flavor Materials, 6th Edition, Wiley-VCH, Weinheim, 2016 “or“ John Wright, Flavor Creation, Second Edition, 2011 ”.

The following flavors or fragrances or flavor or fragrance compositions may be mentioned in detail:

Flavors or fragrances or flavor or fragrance compositions from ambergris; Amyris; Angelica seeds; Angelica root; Anise; Valerian; Basil; Tree moss; Bay; Mugwort; Bergamot; Beeswax; Birch tar; Bitter almond; Savory; Bucco leaves; Cabreuva; Cade; Calmus; Camphor; Cananga; Cardamoms; Cascarilla; Cassia; Cassie; Castoreum; Cedar leaves; Cedar wood; Cistus; Citronella; Lemons; Copaiva ;; Coriander; Costus root; Cumin; Cypress; Davana; Dill herb; Dill seeds; Oak wood; Oak moss; Elemi; Tarragon; Eucalyptus citriodora; Eucalyptus; Fennel; Spruce needle; Galbanum; Geranium; Grapefruit; Guaiac wood; Gurjun; Flelichrysum; Flelichrysum; Ginger; Orris root; Jasmine; Sweet flag; Camomiles ;; Carrot seeds; Cascarilla; Pine needle; Spearmint; Caraway seed; Labdanum; Labdanum; Lavandin; Lavender; Lemongrass; Lovage; Lime; Linaloe; Litsea cubeba; Bay leaves; Mace; Marjoram; Tangerine; Massoir bark; Mimosa; Musk grains; Muscat sage; Nutmeg; Myrrh; Myrtles; Clove leaves; Carnation flower; Neroli; Olibanum; Opopanax; Orange blossom; Orange; Origanum; Palmarosa; Patchouli; Perilla; Balsam tree; Parsley leaves; Parsley seeds; Petitgrain; Peppermint; Pepper; Pimento; Pine; Poley; Rose; Rosewood; Rosemary; Sage Dalmatian; Sage spanish; Sandalwood; Celery seeds; Spiclavender; Star anise; Styrax; Tagetes; Pine needle; Tea tree; Thyme; Tonka; Tuberose; Vanilla; Violet leaves; Verbena; Vetiver; Juniper berry; Wine yeast; Wormwood; Wintergreen; Ylang; Hyssop; Civet; Cinnamon leaves; Cinnamon bark, tea and coffee.

Individual flavorings or fragrances are preferably selected from the following groups:

Hydrocarbons such as 3-carene; a-pinene; ß-pinene; a-terpinene; g-terpinene; p-cymene; Bisabolene; Camphene; Caryophyllene; Cedren; Ferns; Limonene; Longifolene; Myrcene; Ocimen; Valencene; (E, Z) -1, 3,5-undecatriene; Styrene; Diphenylmethane;

Aliphatic alcohols such as Flexanol; Octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (EJ-2-Flexenol; (E) - and (ZJ-3-Flexenol; 1-octen-3-ol; mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-nonadienol; 3,7-dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10 -Undecenol; 4-methyl-3-decen-5-ol; Aliphatic aldehydes and their acetals, such as, for example, hexanal; Heptanal; Octanal; Nonanal; Decanal; Undecanal; Dodecanal; Tridecanal; 2-methyloctanal; 2-methyl nonanal; (EJ-2-hexenal; (ZJ-4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E) - 4-decenal; 2-dodecenal; 2,6,10-trimethyl-9- undecenal; 2,6,10-trimethyl-5, 9-undecadienal; heptanal diethyl acetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene;

Citronellyloxyacetaldehyde; 1 - (1-methoxy-propoxy) - (E / Z) -3-hexene;

Aliphatic ketones and their oximes such as 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2, 4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;

Aliphatic sulfur-containing compounds such as 3-methylthio-hexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthen-8-thiol;

Aliphatic nitriles such as 2-nonenoic acid nitrile; 2-undecenoic acid nitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6-octadiene-acid nitrile; 3,7-dimethyl-6-octenonitrile;

Esters of aliphatic carboxylic acids such as (E) - and (ZJ-3-hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (EJ-2-hexenyl acetate; (E) - and (ZJ-3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-ylacetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E) - and (ZJ-3-hexenyl isobutyrate; hexyl crotonate; Ethyl isovalerate; ethyl 2-methylpentanoate; ethyl hexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; ethyl (E, Z) -2,4-decadienoate; methyl 2-octinate; methyl 2-nonynate; allyl 2-isoamyloxyacetate; Methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate;

Acyclic terpene alcohols such as. B. Citronellol; Geraniol; Nerol; Linalool; Lavadulol; Nerolidol; Farnesol; Tetrahydrolinalool; Tetrahydrogeraniol; 2,6-dimethyl 7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylen-7-octen-2-ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol; 2,6-dimethyl-2,5,7-octatrien-1-ol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

Acyclic terpene aldehydes and ketones such. B. Geranial; Neral; Citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,1 O-trimethyl-9-undecenal; Geranylacetone; as well as the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;

Cyclic terpene alcohols such as. B. menthol; Isopulegol; alpha-terpineol; Terpinenol-4; Menthan-8-ol; Menthan-1-ol; Menthan-7-ol; Borneol; Isoborneol; Linalool oxide; Nopoly; Cedrol; Ambrinol; Vetiverol; Guajol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, flexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;

Cyclic terpene aldehydes and ketones such. B. menthone; Isomenthone; 8-mercaptomenthan-3-one; Carvone; Camphor; Fenchone; alpha-ionon; beta-ionon; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-lron; alpha damascone; beta damascone; beta-damascenone; delta damascone; gamma damascone; 1 - (2,4,4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1, 3,4,6,7,8a-Flexahydro-1, 1, 5,5-tetramethyl-2FI-2,4a-methanonaphthalene-

8 (5FI) -one; 2-methyl-4- (2,6,6-trimethyl-1-cyclohexen-1 -yl) -2-butenal; Nootkatone;

Dihydronootkatone; 4,6,8-megastigmatrien-3-one; alpha-sinensal; beta-sinensal; acetylated cedarwood oil (methyl cedryl ketone);

Cyclic alcohols such as, for example, 4-tert.-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2FI-pyran-4-ol; Cycloaliphatic alcohols such as alpha, 3,3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1 -yl) butanol;

2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-

3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1 - (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1 - (2,2,6-trimethylcyclohexyl) hexan-3-ol;

Cyclic and cycloaliphatic ethers such as cineole; Cedryl methyl ether; Cyclododecyl methyl ether; 1,1-dimethoxycyclododecane;

(Ethoxymethoxy) cyclododecane; alpha cedrene epoxide; 3a, 6, 6, 9a-

Tetramethyldodecahydronaphtho [2,1 -b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2,1 -b] furan; 1, 5,9-trimethyl-13-oxabicyclo [10.1 .0] tri- deca-4,8-diene; Rose oxide; 2- (2,4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane;

Cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-

Pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,2,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; Cyclopentadecanone;

Cyclohexadecanone;

Cycloaliphatic aldehydes such as 2,4-dimethyl-3-cyclohexenecarbaldehyde;

2-methyl-4- (2,2,6-trimethyl-cyclohexen-1 -yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -

3-cyclohexenecarbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarbaldehyde;

Cycloaliphatic ketones such as. B. 1 - (3,3-Dimethylcyclohexyl) -4-penten-1-one; 2,2-dimethyl-1 - (2,4-dimethyl-3-cyclohexen-1 -yl) -1-propanone; 1 - (5,5-dimethyl-1 -cyclo- hexen-1 -yl) -4-penten-1-one; 2,3,8,8-tetramethyM, 2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; Methyl 2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl- (2,4-dimethyl-3-cyclohexen-1-yl) ketone;

Esters of cyclic alcohols such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyl tetrahydro-2H-pyran-4-ylacetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 or 6-indenyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 or 6-indenyl propionate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-indenyl isobutyrate; 4,7-methanooctahydro-5 or 6-indenyl acetate;

Esters of cycloaliphatic alcohols such as 1-cyclohexylethyl crotonate;

Esters of cycloaliphatic carboxylic acids such as. B. allyl 3-cyclohexyl propionate; Allylcyclohexyloxyacetate; cis and trans methyl dihydrojasmonate; cis and trans methyl jasmonate; Methyl 2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexene carboxylate; Ethyl 2-methyl-1,3-dioxolane-2-acetate;

Araliphatic alcohols such as benzyl alcohol; 1-phenylethyl alcohol; 2-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl alcohol; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenyl-propanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1 - (4-isopropylphenyl) ethanol;

Esters of araliphatic alcohols and aliphatic carboxylic acids such as benzyl acetate; Benzyl propionate; Benzyl isobutyrate; Benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha-trichloromethylbenzyl acetate; alpha, alpha- Dimethylphenylethyl acetate; alpha, alpha-dimethylphenylethyl butyrate; Cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;

Araliphatic ethers such as 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether;

Phenylacetaldehyde dimethyl acetal; Phenylacetaldehyde diethyl acetal;

Hydratropaaldehyde dimethyl acetal; Phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5, 9b-tetrahydro-2,4-dimethylindeno [1,2-d] -m-dioxin;

Aromatic and araliphatic aldehydes such as. B. benzaldehyde; Phenylacetaldehyde; 3-phenylpropanal; Hydratropaaldehyde; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; 2-methyl-3- (4-tert-butylphenyl) propanal; 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; Cinnamaldehyde; alpha-butyl cinnamaldehyde; alpha-amylcinnamaldehyde; alpha-hexyl cinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) propanal; 2-methyl-3- (4-methylenedioxyphenyl) propanal;

Aromatic and araliphatic ketones such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1 - (2-naphthalenyl) ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl) ethanone; Benzophenone; 1, 1, 2, 3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone; 1 - [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; 5 ‘, 6‘, 7 ‘, 8‘-tetrahydro-3‘, 5 ‘, 5‘, 6 ‘, 8‘, 8‘-hexamethyl-2-acetonaphthone;

Aromatic and araliphatic carboxylic acids and their esters, such as, for example, benzoic acid; Phenylacetic acid; Methyl benzoate; Ethyl benzoate; Hexyl benzoate; Benzyl benzoate; Methylphenyl acetate; Ethyl phenyl acetate; Geranyl phenyl acetate; Phenylethyl phenyl acetate; Methylcinnmat; Ethyl cinnamate; Benzyl cinnamate; Phenylethyl cinnamate; Cinnamyl cinnamate; Allyl phenoxyacetate; Methyl salicylate; Isoamyl salicylate; Hexyl salicylate; Cyclohexyl salicylate; Cis-3-hexenyl salicylate; Benzyl salicylate; Phenylethyl salicylate; Methyl 2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenyl glycidate; Ethyl 3-methyl-3-phenyl glycidate;

Nitrogen-containing aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butyl acetophenone;

Cinnamonitrile; 3-methyl-5-phenyl-2-pentenoic acid nitrile; 3-methyl-5-phenylpentanoic acid nitrile; Methyl anthranilate; Methyl N-methyl anthranilate; Schiff’s bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6- isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2- (3-phenylpropyl) pyridine; Indole; Skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;

Phenols, phenyl ethers and phenyl esters such as estragole; Anethole; Eugenol; Eugenyl methyl ether; Isoeugenol; Isoeugenyl methyl ether; Thymol; Carvacrol; Diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether; 1,4-dimethoxybenzene; Eugenyl acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-cresylphenyl acetate;

Heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;

Lactones such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1, 4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide; 4-methyl-1,4-decanolide; 1, 15-pentadecanolide; cis- and trans-11-pentadecen-1, 15-olide; cis- and trans-12-pentadecen-1, 15-olide; 1, 16-hexadecanolide; 9-hexadecen-1, 16-olide; 10-oxa-1, 16-hexadecanolide; 11-oxa-1, 16-hexadecanolide;

12-oxa-1, 16-hexadecanolide; Ethylene 1, 12-dodecanedioate; Ethylene 1,13-tridecanedioate; Coumarin; 2,3-dihydrocoumarin; Octahydrocoumarin; And any mixtures of the aforementioned flavors or fragrances.

The aroma load with the at least one flavor and / or fragrance is usually very low in the gas or vapor phase, ie the flavors and / or fragrances are present in a sensorially perceptible amount, but not in relevant concentrations for the Use for flavoring. In order to be able to use the gas or vapor phase with at least one taste and / or fragrance, the at least one taste and / or fragrance must be concentrated so that an enrichment of a sensory effective amount of the taste and / or fragrance occurs.

The term "sensory effective amount" means in the context of the present application that the flavor or the aroma or the fragrance or the fragrance is present in such a sufficient amount that the resulting product, when used, the sensory properties of the Flavor or the aroma or the fragrance or the fragrance can be recognized.

The flavors and / or fragrances are usually present in the gas or vapor phase in a concentration of 0.001 to 1,000 ppm, based on the total volume of the gas or vapor phase.

In a next step (1b) of the method according to the invention according to the first aspect and / or step (2b) of the method according to the invention according to the second aspect, an adsorption material (sorbent) is provided in an adsorption device.

The adsorption material (sorbent) is placed in a device suitable for carrying out the adsorption. The adsorption device is preferably an adsorption column. A device suitable for receiving the adsorption material or for loading it with the adsorption material is usually a column made of glass or stainless steel, the column size or the column volume (BV) usually 0.1 l to 500 l, preferably 20 l or 300 I. The ratio of the inner diameter to the length or height of these columns is preferably 0.05 to 0.5, preferably 0.1 to 0.4 or 0.2 to 0.3. An exemplary particularly preferred column has a column size or a column volume (BV) of 300 l, an inner diameter of 0.51 m and a length or height of 1.45 m.

In the context of the present invention, in principle all adsorption materials can be used as the stationary phase, which are usually used in adsorption / desorption processes and are suitable for absorbing the flavors and / or fragrances from the aroma-laden gas or vapor phase.

Due to the different polarity of the flavors and / or fragrances, the adsorbent material is selected in the method according to the invention so that both the polar, medium-polar, and non-polar flavors and / or fragrances are equally adsorbed on the adsorbent material and none of the polar, medium polar or non-polar taste and / or fragrance is discriminated.

Preferred adsorption materials that are used in the process according to the invention according to the first and / or second aspect for the recovery or enrichment of the flavors and / or fragrances are variously crosslinked polystyrenes, preferably copolymers of ethylvinylbenzene and divinylbenzene, vinylpyrrolidone and divinylbenzene, vinylpyridine and divinylbenzene, styrene and divinylbenzene, copolymers of acrylic acid, divinylbenzene and aliphatic diene, but also other polymers, preferably polyaromatics, polystyrenes, poly (meth) acrylates, polypropylene, polyester and polytetrafluoroethylene, etc .. The adsorption materials can also have surface modifications.

Polystyrenes, in particular non-surface-modified, crosslinked macroporous polystyrenes, preferably Lewaplus®, Lewatit®, Lewabrane®, Bayoxide®, preferably Lewatit®, more preferably Lewatit® S or Lewatit® VPOC, such as Lewatit, are particularly preferred as the stationary phase ® S 100 G1, Lewatit® S 1567, Lewatit® S 1568, Lewatit® S 4528, Lewatit® S 5328,, Lewatit® S 7468, Lewatit® S 7968, Lewatit® S 9167, Lewatit® VPOC 1064, Lewatit® VPOC 1065 , Lewatit® VPOC 1074 or Lewatit® VPOC 1600.

Most preferably, Lewatit® VPOC 1064 is used as the stationary phase in the process according to the invention according to the first and second aspects. Good results were achieved, particularly with regard to the yield.

After the loading and before the adsorption step (1c) of the method according to the invention according to the first aspect and / or the adsorption step (2c) of the method according to the invention according to the second aspect, the adsorption material used is conditioned in the adsorption device. During the conditioning, the adsorption material (sorbent) is first cleaned with an organic solvent, which removes impurities on the adsorption material and in the adsorption device. This is done by rinsing the adsorption material (sorbent) in the adsorption device with 5 to 10 times the amount of the column volume (BV) of organic solvent.

The solvent for cleaning the adsorption material (sorbent) is advantageously selected from the group consisting of methanol, ethanol, acetone, n-propanol and isopropanol.

Next, in the conditioning, the adsorption material (sorbent) in the adsorption device is rinsed with deionized water. This is done by passing deionized water through the adsorption device with 3 to 5 times the amount of the column volume. After rinsing with Deionized water, the adsorption material saturated with water is dried with inert gas, preferably nitrogen, in order to remove excess deionized water from the adsorption material (sorbent).

After conditioning, the adsorption material has a moisture content of 20 to 50% by weight, preferably a moisture content of 25 to 40% by weight.

For the adsorption step (1c) of the method according to the invention according to the first aspect or the absorption step (2c) of the method according to the invention according to the second aspect, the aroma-laden gas or vapor phase from the exhaust air, which in a thermal treatment or an evaporation - and / or evaporation process of the starting material was generated, and comprises at least one flavor and / or fragrance, fed directly to the adsorption device and passed through the adsorption material.

The temperature of the aroma-laden gas or vapor phase when it is applied, i.e. when it is fed to the adsorption device, is in a range of up to a maximum of 100 ° C under normal pressure, preferably in a range of 70 to 90 ° C.

When the aroma-laden gas or vapor phase is passed through the adsorption material, i.e. during the adsorption phase, the flavor and / or fragrances from the gas or vapor phase condense and absorb on the adsorption material.

The direct application of the aroma-laden gas or vapor phase to the adsorption device in the method according to the invention according to the first and / or second aspect has the advantage that an additional condensation step is not required. This makes a condensation apparatus usually connected upstream of the adsorption columns, the acquisition of which is associated with high costs, superfluous and, moreover, saves energy costs that arise when the aroma-laden gas or vapor phase condenses. In addition, with the direct application of the gas or vapor phase into the adsorption device, flavors and / or fragrances, in particular volatile flavors and / or fragrances, can be absorbed faster, ie without delay, and better on the adsorption material, see above that no oxidation of the flavor and / or fragrance can take place. This means that the gas or vapor phase can be used with fewer losses or even without losses of the valuable taste and / or odorous substances, in particular without degradation or change in the taste and / or odorous substances, and thus while largely maintaining its original composition, ie its original sensory Profile can be recovered or enriched or concentrated without additional energy expenditure.

In addition, the method according to the invention makes storage of a condensate obsolete according to the first and / or second aspect, so that losses of flavorings and / or fragrances, in particular volatile flavors and / or fragrances, which occur during storage of the condensates, for example, by evaporation, by oxidation or by microorganisms, can be avoided.

In a further preferred embodiment of the method according to the invention according to the first aspect and the method according to the invention according to the second aspect, the flow rate of the aroma-loading gas or vapor phase is set in the range from 1 to 100 BV / min during the adsorption process. The parameter of the

The flow rate is jointly responsible for the degree of adsorption and thus for the formation of the local distribution coefficients of the one or more flavorings and / or fragrances between the adsorption material and the gas or vapor phase. The flow rate is preferably in the range from 1 to 50 BV / min, more preferably in the range from 5 to 10 BV / min. The adsorption step of the method according to the invention according to the first and / or second aspect is carried out at a temperature in the adsorption device in the range from 20 ° C to 150 ° C. Preferably, the temperature during the adsorption step in the adsorption device is in the range from 30 ° C to 120 ° C, more preferably in the range from 40 to 100 ° C. Most preferred is a temperature range of 70 ° C to 90 ° C.

The temperature parameter is also jointly responsible for the degree of adsorption and thus for the formation of the local distribution coefficients of the one or more flavorings and / or fragrances between the adsorption material and the gas or vapor phase.

In an alternative variant, in the adsorption step in the method according to the invention according to the first aspect and the method according to the invention according to the second aspect, a targeted adsorption of the one or more flavor and / or fragrance (s) can be carried out via the temperature , wherein the temperature is selected so that certain flavors and / or fragrances adsorb faster on the sorbent, while other flavors and / or fragrances are discriminated at the same time.

In the method according to the invention, the temperature in the adsorption device is preferably selected so that all of the flavors or fragrances contained in the gas or vapor phase are adsorbed on the sorbent and no taste or fragrance (s) are discriminated will become.

In a further preferred embodiment, the adsorption process is carried out both in the method according to the invention according to the first aspect and in the method according to the invention according to the second aspect at a slight overpressure or counter pressure. The back pressure within the adsorption device is that pressure which is created by the resistance of the adsorption material when the aroma-laden gas or vapor phase is passed or pumped through the adsorption device. The back pressure is preferably within the adsorption device during the Adsorption process in the range from 0 bar to 2.5 bar, particularly preferably from 0 bar to 1.5 bar. Most preferably the back pressure is in the range from 0 bar to 0.1 bar.

In a further preferred embodiment of the method according to the invention according to the first aspect and the method according to the invention according to the second aspect, the aroma-laden gas or vapor phase is transported using air or a (preferably compressed) gas in the adsorption device. Preferred gases are inert gases, in particular the inert gases argon, nitrogen, carbon dioxide or mixtures thereof. By using air or an inert gas, the transport of the aroma-laden gas or vapor phase through the column is accelerated, so that the flavorings and / or fragrances adsorb more quickly on the sorbent.

The use of inert gases to support the transport of the aroma-laden gas or vapor phase in the process according to the invention is particularly advantageous in the case of flavors and / or fragrances that are susceptible to oxidation, i.e. easily oxidizable, and which are protected from oxidation with the inert gas. Flavors and / or fragrances susceptible to oxidation can form undesired notes (off-notes or off-flavor) when the method according to the invention is carried out without the use of inert gas, which can lead to a change in the sensory profile. Sulfur-containing flavorings and certain classes of substances known to those skilled in the art, such as aldehydes, are particularly susceptible to oxidation.

For the subsequent desorption or elution of the flavors and / or fragrances from the adsorption material, in the method according to the invention according to the first aspect in a further step (1 d) and in the method according to the invention according to the second aspect in a further step (2d) at least one food-safe organic solvent or a solvent mixture which comprises at least one food-safe solvent, or in an alternative variant at least one food-safe organic mixture which is suitable as a solvent or a mixture of substances, which comprises at least one food-grade organic substance with solvent properties, provided as a mobile phase or eluent.

Food-safe solvents are understood as meaning those solvents which are suitable for consumption and are legally permitted for the preparation of food. Suitable solvents are listed, for example, in Directive 2009/32 / G of the European Parliament and of the Council.

In the method according to the invention according to the first aspect and in the method according to the invention according to the second aspect, the desortpion of the flavors and / or fragrances from the adsorption material is preferably the at least one food-safe organic solvent selected from the group consisting of methanol , Ethanol, propanol, isopropanol, ethyl acetate, diacetin, triacetin, liquid carbon dioxide, food-grade fluorocarbons and vegetable triglycerides or mixtures thereof. Even more preferably, ethanol, n-propanol, isopropanol, ethyl acetate, diacetin and triacetin or mixtures thereof are used to elute the absorbed flavors and / or fragrances from the stationary phase. Most preferably, ethanol, n-propanol or isopropanol or mixtures thereof are used. Most preferably, ethanol is used as the solvent for elution in the method of the invention.

A solvent mixture according to the present invention comprises at least one of the above-mentioned organic solvents in combination with a further from the group of the organic solvents listed above. In addition, a solvent mixture comprises at least one of the above-mentioned solvents mixed with water.

The at least one food-safe organic mixture which is suitable as a solvent or a substance mixture which comprises at least one food-safe organic substance with solvent properties is preferably a substance or a mixture of substances which has solvent properties and which / that typically as an ingredient of Food is used, preferably vegetable oils, essential oils, sugar syrups, etc. Such vegetable oils are selected from the group consisting of sunflower, soy, rapeseed, peanut, palm, wheat germ, corn germ, olive and linseed oil .

In the method according to the invention for desorption of the flavorings or fragrances from the sorbent, the solvents listed above are preferably used in pure form.

Ethanol, preferably 96% ethanol, is most preferred in particular because the resulting eluate enriched with a flavor or fragrance can be used without distilling off the solvent and thus exposure to temperature. This prevents loss of flavor and / or fragrance in the enriched eluate due to thermal degradation. In addition, ethanol prevents microbial spoilage of the enriched aroma phase, even if the aroma phase is stored later. However, it is also possible to desorb or elute ethanol-free, which can be of particular importance for halal products.

The term “solvent mixture” in the context of the present invention includes all conceivable combinations of the organic solvents listed above with one another. In addition, the term also includes the mixtures of at least one of the aforementioned organic solvents with at least one other food-safe organic solvent, which are listed in the aforementioned Directive 2009/32 / EC, or the mixture of at least one of the aforementioned organic solvents with water.

If a solvent mixture which comprises at least one of the abovementioned organic solvents is used for desorption, the mixing ratio of organic solvent to another organic solvent is in a range from 98: 2 (v / v) to 20:80 (v / v), the mixing ratio is preferably 95: 4, even more preferably 90:10. If the organic solvent is used in a mixture with water, the mixing ratio is of organic solvent to water in a range from 98: 2 (v / v) to 20:80 (v / v), preferably the mixing ratio is 95: 4, even more preferably 90:10.

For desorption, in the method according to the invention according to the first aspect in a further step (1e) and in the method according to the invention according to the second aspect in a further step (2e), the at least one flavor and / or fragrance is mixed with the food-safe Solvent or the solvent mixture is eluted from the stationary phase to give an eluate which comprises the at least one desorbed flavor or fragrance.

In the desorption step (1e) in the method according to the invention according to the first aspect and the desorption step (2e) in the method according to the invention according to the second aspect, preferably no targeted discriminations of flavors and / or fragrances are made.

Alternatively, in the desorption step in the method according to the invention according to the first aspect and the method according to the invention according to the second aspect, a targeted discrimination of the one or more flavor and / or fragrance (s) can be carried out by targeted desorbing, the solvents used for elution or the solvents used for elution are selected so that they have a different log Pow ^* value. In addition, a targeted discrimination of the one or more flavorings and / or fragrances is also possible via a solvent gradient during the elution.

In the desorption, the flow rate of the selected solvent or solvent mixture can be 0.1 to 20.0 column volumes / hour (BV / h), preferably 0.2 to 15.0 BV / h, 0.3 to 12.0 BV / h, 0.4 to 1 1, 0 BV / h, 0.5 to 10.0 BV / h, 0.6 to 9.0 BV / h, 0.7 to 8.0 BV / h, 0, 9 to 7.0 BV / h, 1.0 to 6.0 BV / h, 1. 25 to 5.0 BV / h, 1.5 to 4.0 BV / h, 1.75 to 3.5 BV / h, 2.0 to 3.0 BV / h, 2.25 to 2.75 BV / h or 2.5 BV / h. Most preferably, the elution is carried out with a mobile phase flow rate of 1.0 to 5.0 BV / h. The temperature of the eluent is usually 0 ° C to 60 ° C, preferably 10 ° C to 50 ° C, more preferably 20 ° C to 35 ° C, and most preferably 25 ° C to 30 ° C. The parameter of the temperature is partly responsible for the degree of desorption of the aroma substances. A temperature range from 10 ° C. to 40 ° C. is also preferred, particularly preferably a temperature range from 15 ° C. to 40 ° C.

The back pressure during the desorption process can be 0.05 bar to 2.0 bar and can be determined, for example, with a conventional manometer. The counterpressure during the desorption process is the pressure created by the resistance of the adsorption material when the eluent is pumped through the column packed with adsorption material. The counterpressure within the adsorption device during the desorption process is preferably in the range from 0.1 bar to 1.0 bar, particularly preferably from 0.2 bar to 0.5 bar.

The directions of the adsorption step and the desorption step can be in the same direction or opposite in the method according to the invention according to the first and / or second aspect.

The adsorption step and / or the desorption step in the method according to the first and / or second aspect of the present invention is / are preferably as in EP 2 075 320 A1 or EP 2 075 321 A1, which are disclosed in this regard by reference in their entirety are incorporated into the present application, set out, carried out.

Through the targeted selection of the solvent for the elution or desorption of one flavor and / or fragrance, the method according to the invention according to the first and / or second aspect allows an eluate or a flavor concentrate without the use, ie addition of alcohol, especially of ethanol. Such products can be used for the production of non-alcoholic foods.

The method according to the invention according to the first aspect of the present invention leads to an eluate in which the at least one flavor and / or fragrance is enriched. The recovery or enrichment of the at least one flavor and / or fragrance from the aroma-laden gas or vapor phase is 1,000 to 1,000,000, preferably 1,000 to 100,000, based on the original content of flavors and / or fragrances in the feed, i.e. . H. the concentration of the vapor phase.

The eluate obtained in the method according to the invention according to the first aspect, which comprises the at least one desorbed flavor or fragrance, can if necessary and depending on the further use. be concentrated in a further step (1 f) using methods known from the prior art, for example by partial distillation of the at least one organic solvent or solvent mixture with which the at least one flavor or fragrance was eluted. As a result, an aroma phase enriched with the at least one flavor and / or fragrance is obtained.

In the method according to the second aspect of the invention, the eluate which comprises the at least one desorbed flavor or fragrance is concentrated in a further step (2f) using methods known from the prior art by completely distilling off the at least one organic Solvent or solvent mixture with which the elution of the at least one flavor or fragrance was carried out, so that an aroma concentrate is produced. The flavor concentrate contains the at least one flavor and / or fragrance in concentrated form.

Surprisingly, it has been found in the context of the present invention that the combination of an aroma-laden gas or Vapor phase with an adsorption / desorption process, as described in the present case, the stated difficulties from the prior art can be solved and the valuable flavors and / or fragrances can be recovered or enriched without loss. Additional condensation of the vapor phase is not necessary. This prevents oxidation of flavors and / or fragrances which are susceptible to oxidation and which is usually associated with condensation. Consequently, with the method according to the invention according to the first and / or second aspect, undesired notes (false notes or off-flavor) which lead to a change in the sensory profile can be prevented. In this way, with the method according to the invention according to the first and second aspects of the present invention, valuable flavors and / or fragrances can be recovered or enriched from an aroma-laden gas or vapor phase while largely retaining their original composition, ie their original sensory profile, without additional expenditure of energy be concentrated.

In addition, according to the first and / or second aspect, the method according to the invention makes the storage of a condensate obsolete, so that losses of flavors and / or fragrances, in particular volatile flavors and / or fragrances, which occur during storage of the condensates, for example, by evaporation, by oxidation or by microorganisms, can be avoided.

In a further aspect, the present invention thus also relates to an eluate which is enriched with the at least one flavor and / or fragrance which can be obtained by the method described above according to the first aspect of the present invention, or an aroma concentrate, which is obtainable by the method described above according to the second aspect of the present invention.

The eluate according to the invention or the aroma concentrate according to the invention is characterized by greater authenticity in taste and smell, since the Process odor and taste-active substances are retained and are not lost or broken down.

In the eluate according to the invention or the aroma concentrate according to the invention, the factor of concentration or enrichment of the at least one flavor and / or fragrance from the aroma-laden gas or vapor phase is in the range from 1,000 to 1,000,000, preferably in the range from 10,000 up to 300,000, based on the original content of flavor and / or fragrance in the feed, d. H. the concentration in the vapor phase

The factor for the concentration of the at least one flavor and / or fragrance in the enriched aroma phase or the aroma concentrate is more preferably in the range from 1,000 to 100,000.

A further aspect of the present invention relates to the use of the eluate according to the invention, which is enriched with the at least one flavor and / or fragrance, or the flavor concentrate according to the invention for flavoring or for reconstituting the aroma of food, luxury foods, beverage products, semi-finished products, Oral hygiene products, cosmetics, pharmaceutical products or pet food or for the production of food, luxury goods, beverage products, semi-finished products, oral hygiene products, cosmetics, pharmaceutical products or pet food.

Due to the nature of the flavors and fragrances, the eluate according to the invention or the flavor concentrate according to the invention is suitable as an additive to foods from which the gas or vapor phase has been generated, to reconstitute the flavor, or they can be added to other foods for flavoring.

Furthermore, the aforementioned eluate or the aroma concentrate can be added to an eluate or concentrate produced by another method, in order to obtain a more complete taste or fragrance profile which, for example, comes close to natural profiles which otherwise have a lower sensory nature identity in other processes due to the depletion of certain sensory components.

In addition to these reconstructive advantages, the present method also leads to a higher yield of flavorings and fragrances from the original plants or a greater concentration in the eluate / concentrate.

Finally, the present invention relates to food, luxury goods, beverage products, semi-finished products, oral hygiene products, cosmetics, pharmaceutical products or animal foods which comprise the eluate according to the invention, which is enriched with the at least one flavor and / or fragrance, or the aroma concentrate according to the invention.

In a preferred embodiment, the products listed above comprise the eluate according to the invention, which is enriched with the at least one flavor and / or fragrance, or the flavor concentrate according to the invention in an amount of 0.001 to 5% by weight, preferably in the range of 0.1 to 1% by weight, based on the total weight of the preparation.

Experimental part

example 1

Composition of an eluate which was obtained from an aroma-laden gas or vapor phase from the drying of fresh mint leaves

The eluate was prepared as follows:

Adsorption:

Product: garden mint

Insert: 27.59 g

Apparatus: 2 liter glass autoclave

Jacket temperature: 95 ° C

Gas head temperature: 80 ° C

Gas flow: 100 ml / min

Sampling time: 4 hours

Adsorption column: 250mm ^* 25mm glass column

Adsorption material: 60 g Lewatit VOPC 1064

The fresh garden mint was placed in the autoclave and this closed. The double jacket was then heated to 95.degree. After the jacket temperature had been reached, nitrogen (100 ml / min) was passed into the autoclave from the lower end of the autoclave. At the upper end of the autoclave, the aroma-laden gas or steam flow with the taste or fragrance components (80 ° C) was directly applied to the adsorption column and the

Adsorption material passed. The adsorption was stopped after 4 hours.

[0152] Desorption:

Apparatus: Knauer HPLC pump; Nitrogen line with pressure regulator

Eluent: ethanol

Flow: 5 ml / min

Temperature: room temperature Pre-fraction: 20 ml (discarded)

Main fraction 100 ml (82.0 g)

Before the elution, the adsorption column was blown dry for 3 minutes with ethanol at 0.1 bar with nitrogen in the direction of adsorption. It was then eluted with ethanol in the opposite direction. After taking off a preliminary fraction, the main fraction was eluted. The main fraction of the eluate had the composition given in Table 1.

Table 1

Example 2

Composition of an eluate that was obtained from an aroma-laden gas or vapor phase from the drying of black tea

The eluate was prepared as follows:

Adsorption:

Product: Black tea from Kenya (Camellia sinensis (L.) Kuntze) and 377.6 g of water

Amount of tea used: 151.0 g

Apparatus: 2 liter glass autoclave

Jacket temperature: 95 ° C

Gas head temperature: 80 ° C

Gas flow: 100 ml / min

Sampling time: 5 hours

Adsorption column: 250mm ^* 25mm glass column

Adsorption material: 60 g Lewatit VOPC 1064

The swollen black tea was placed in the autoclave and this closed. The double jacket was then heated to 95.degree. After the jacket temperature had been reached, nitrogen (100 ml / min) was passed into the autoclave from the lower end of the autoclave. At the upper end of the autoclave, the aroma-laden gas or steam flow with the taste or fragrance components (80 ° C) was directly applied to the adsorption column and the

Adsorption material passed. The adsorption was stopped after 5 hours.

[0158] Desorption:

Apparatus: Knauer HPLC pump

Nitrogen line with pressure regulator

Eluent: ethanol Flow: 5 ml / min

Temperature: room temperature

Pre-fraction: 20 ml (discarded)

Main fraction 50 ml (41, 76 g)

The adsorption column was blown dry with nitrogen in the direction of adsorption for 3 minutes at 0.1 bar before elution with ethanol. It was then eluted with ethanol in the opposite direction. After taking off a preliminary fraction, the main fraction was eluted. The main fraction of the eluate had the composition shown in Table 2.

Table 2

Claims

1. Process for the recovery or enrichment of one or more

Flavor and / or fragrance (s), consisting of or comprising the following steps:

2. A method for producing a flavor concentrate, consisting of or comprising the following steps: (2a) providing an aroma-laden gas or vapor phase, comprising at least one flavor and / or fragrance;

(2b) providing and conditioning an adsorption material in an adsorption device;

3. The method according to claim 1 or claim 2, in which the adsorption material is selected from the group consisting of crosslinked polystyrenes, in particular copolymers of ethylvinylbenzene and divinylbenzene, vinylpyrrolidone and divinylbenzene, vinylpyridine and divinylbenzene, styrene and divinylbenzene; Copolymers of acrylic acid, divinylbenzene and aliphatic diene; and polymers, especially polyaromatics, polystyrenes, poly (meth) acrylates, polypropylenes, polyesters and polytetrafluoroethylene, especially Lewatit®.

4. The method according to any one of claims 1 to 3, in which the conditioning of the adsorbent material in step (1b) or (2b) consists of the following steps or comprises the following steps:

Cleaning the adsorbent material with an organic solvent;

- Passing deionized water through the adsorption device; and

- Removal of the deionized water from the adsorption device with an inert gas, in particular nitrogen.

5. The method according to any one of claims 1 to 4, wherein the adsorbent material has a moisture of 20 to 50 wt .-% after removal of the deionized water from the adsorption device.

6. The method according to any one of claims 1 to 5, wherein the food grade organic solvent is selected from the group consisting of methanol, ethanol, propanol, isopropanol, ethyl acetate, diacetin, triacetin, liquid carbon dioxide, food grade fluorocarbons and vegetable triglycerides or mixtures thereof.

7. The method according to any one of claims 1 to 6, wherein the elution is carried out at a flow rate of 1.0 to 5.0 BV / h.

8. The method according to any one of claims 1 to 7, wherein the elution is carried out at a temperature in the range from 0 ° C to 60 ° C, in particular at a temperature in the range from 15 ° C to 40 ° C.

9. The method according to any one of claims 1 to 8, wherein the elution is carried out at a pressure of 0.05 to 2.0 bar.

10. Aroma phase, enriched with the at least one flavor and / or fragrance, or aroma concentrate, producible by a method according to one of claims 1 to 9.

1 1. Aroma phase or aroma concentrate according to Claim 10, in which the factor for the concentration of the at least one flavor and / or fragrance in the enriched aroma phase or the aroma concentrate is in the range from 1,000 to 100,000.

12. Use of the enriched aroma phase or the aroma concentrate according to one of claims 10 or 1 1 for flavoring or for reconstituting the aroma of food, luxury goods, beverage products, semi-finished products, oral hygiene products, cosmetics, pharmaceutical products or animal foods or for the production of foodstuffs, luxury foods , Beverage products, semi-finished products, oral hygiene products, cosmetics, pharmaceutical products or pet food.

13. Food, luxury goods, beverage products, semi-finished products, oral hygiene products, cosmetics, pharmaceutical products and animal foods, comprising an enriched aroma phase or an aroma concentrate according to one of claims 10 or 11, in particular in an amount of 0.1 to 1% by weight.