WO2021004638A1 - Procédé permettant une récupération ou un enrichissement en substances gustatives ou odorantes à partir d'une phase gazeuse chargée en arômes, et concentré aromatique - Google Patents

Procédé permettant une récupération ou un enrichissement en substances gustatives ou odorantes à partir d'une phase gazeuse chargée en arômes, et concentré aromatique Download PDF

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Publication number
WO2021004638A1
WO2021004638A1 PCT/EP2019/068721 EP2019068721W WO2021004638A1 WO 2021004638 A1 WO2021004638 A1 WO 2021004638A1 EP 2019068721 W EP2019068721 W EP 2019068721W WO 2021004638 A1 WO2021004638 A1 WO 2021004638A1
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WIPO (PCT)
Prior art keywords
aroma
solvent
flavor
fragrance
food
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PCT/EP2019/068721
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German (de)
English (en)
Inventor
Stefan Brennecke
Katharina Reichelt
Gerhard Krammer
Original Assignee
Symrise Ag
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Publication date
Application filed by Symrise Ag filed Critical Symrise Ag
Priority to PCT/EP2019/068721 priority Critical patent/WO2021004638A1/fr
Priority to EP20736746.7A priority patent/EP3996525A1/fr
Priority to PCT/EP2020/069666 priority patent/WO2021005239A1/fr
Publication of WO2021004638A1 publication Critical patent/WO2021004638A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/115—Natural spices, flavouring agents or condiments; Extracts thereof obtained by distilling, stripping, or recovering of volatiles
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/40—Tea flavour; Tea oil; Flavouring of tea or tea extract
    • A23F3/42—Isolation or recuperation of tea flavour or tea oil
    • A23F3/426—Isolation or recuperation of tea flavour or tea oil by distillation, e.g. stripping leaves; Recovering volatile gases
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials

Definitions

  • 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.
  • volatile flavors and / or fragrances pass into the gas or vapor phase.
  • 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.
  • Methods for the recovery or enrichment or concentration of flavors and / or fragrances from an aqueous aroma phase 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.
  • 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.
  • 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.
  • 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.
  • aroma-laden gas or vapor phases 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.
  • 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.
  • 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;
  • step (1 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;
  • the present invention relates to a method for
  • (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;
  • 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.
  • 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.
  • 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.
  • 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:
  • step (1 a) 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;
  • step (1 b) 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;
  • the present invention relates to a method for
  • step (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;
  • 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.
  • 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.
  • an aroma-laden gas or vapor phase which comprises at least one flavor and / or fragrance.
  • 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.
  • 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, spectacular raspberry (Rubus spectabilis), sea buckthorn fruit, sloe fruit, strawberry, white cinnamon raspberry (Rubus parviflorus),
  • 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.
  • 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).
  • 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.
  • 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.
  • 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.
  • temperatures in the range from 70 to 90 ° C are preferably used, in which predominantly water is evaporated or evaporated from the starting material.
  • 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% .
  • 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.
  • 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.
  • 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 macrocycl
  • 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 ”.
  • 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; Und
  • 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; ally
  • 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, pentan
  • Acyclic terpene aldehydes and ketones such.
  • 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.
  • 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;
  • Cyclic and cycloaliphatic ethers such as cineole; Cedryl methyl ether; Cyclododecyl methyl ether; 1,1-dimethoxycyclododecane;
  • 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;
  • Cycloaliphatic aldehydes such as 2,4-dimethyl-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
  • 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;
  • 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-
  • 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‘
  • 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
  • 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;
  • 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;
  • 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.
  • 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.
  • sensor 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.
  • an adsorption material (sorbent) is provided in an adsorption device.
  • the adsorption material 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.
  • 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.
  • 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.
  • 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.
  • the adsorption material used is conditioned in the adsorption device.
  • 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.
  • 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).
  • the adsorption material 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the aroma-laden gas or vapor phase is transported using air or a (preferably compressed) gas in the adsorption device.
  • gases are inert gases, in particular the inert gases argon, nitrogen, carbon dioxide or mixtures thereof.
  • 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.
  • 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.
  • 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.
  • 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.
  • ethanol, n-propanol or isopropanol or mixtures thereof are used.
  • 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.
  • 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.
  • vegetable oils are selected from the group consisting of sunflower, soy, rapeseed, peanut, palm, wheat germ, corn germ, olive and linseed oil .
  • the solvents listed above are preferably used in pure form.
  • Ethanol preferably 96% ethanol
  • 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.
  • ethanol prevents microbial spoilage of the enriched aroma phase, even if the aroma phase is stored later.
  • solvent mixture in the context of the present invention includes all conceivable combinations of the organic solvents listed above with one another.
  • 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.
  • 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.
  • 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.
  • 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.
  • a targeted discrimination of the one or more flavorings and / or fragrances is also possible via a solvent gradient during the elution.
  • 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.
  • 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.
  • 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.
  • an aroma phase enriched with the at least one flavor and / or fragrance is obtained.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • composition of an eluate which was obtained from an aroma-laden gas or vapor phase from the drying of fresh mint leaves was obtained from an aroma-laden gas or vapor phase from the drying of fresh mint leaves
  • the eluate was prepared as follows:
  • 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.
  • nitrogen 100 ml / min
  • 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.
  • 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.
  • the eluate was prepared as follows:
  • Amount of tea used 151.0 g
  • Adsorption column 250mm * 25mm glass column
  • Adsorption material 60 g Lewatit VOPC 1064
  • Adsorption material passed. The adsorption was stopped after 5 hours.
  • 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.

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Abstract

L'invention concerne un procédé permettant une récupération ou un enrichissement en substances gustatives et/ou odorantes à partir d'une phase gazeuse ou vapeur chargée en arôme. L'invention concerne aussi un procédé pour préparer un concentré aromatique, un produit d'élution enrichi en une substances gustative et/ou odorante ou un concentré aromatique pouvant être préparé au moyen du procédé selon l'invention. L'invention concerne par ailleurs l'utilisation d'un produit d'élution enrichi de ce type ou d'un concentré aromatique de ce type ainsi que des produits qui comprennent le produit d'élution enrichi selon l'invention ou le concentré aromatique selon l'invention.
PCT/EP2019/068721 2019-07-11 2019-07-11 Procédé permettant une récupération ou un enrichissement en substances gustatives ou odorantes à partir d'une phase gazeuse chargée en arômes, et concentré aromatique WO2021004638A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/EP2019/068721 WO2021004638A1 (fr) 2019-07-11 2019-07-11 Procédé permettant une récupération ou un enrichissement en substances gustatives ou odorantes à partir d'une phase gazeuse chargée en arômes, et concentré aromatique
EP20736746.7A EP3996525A1 (fr) 2019-07-11 2020-07-10 Procédé permettant une récupération ou un enrichissement en substances gustatives ou odorantes à partir d'une phase gazeuse chargée en arômes, et concentré aromatique
PCT/EP2020/069666 WO2021005239A1 (fr) 2019-07-11 2020-07-10 Procédé permettant une récupération ou un enrichissement en substances gustatives ou odorantes à partir d'une phase gazeuse chargée en arômes, et concentré aromatique

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PCT/EP2019/068721 WO2021004638A1 (fr) 2019-07-11 2019-07-11 Procédé permettant une récupération ou un enrichissement en substances gustatives ou odorantes à partir d'une phase gazeuse chargée en arômes, et concentré aromatique

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PCT/EP2020/069666 WO2021005239A1 (fr) 2019-07-11 2020-07-10 Procédé permettant une récupération ou un enrichissement en substances gustatives ou odorantes à partir d'une phase gazeuse chargée en arômes, et concentré aromatique

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EP2075321A1 (fr) 2007-12-17 2009-07-01 Symrise GmbH & Co. KG Procédé destiné à la fabrication d'un concentré d'arômes et concentré d'arômes
WO2012069295A1 (fr) * 2010-11-26 2012-05-31 Unilever Nv Procédé de préparation de produits à base de thé
JP2013216831A (ja) * 2012-04-12 2013-10-24 Ogawa & Co Ltd 保存性に優れた天然香料の製造方法
DE102015119155A1 (de) * 2015-11-06 2017-05-11 Flavologic Gmbh Verfahren und Vorrichtung zum Herstellen eines Aromastoffkonzentrats aus einem Aromastoff-haltigen Edukt
WO2018110585A1 (fr) * 2016-12-16 2018-06-21 長谷川香料株式会社 Procédé de fabrication de composition aromatique à partir de grains de café torréfiés, et dispositif de capture d'arôme à partir de grains de café torréfiés

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EP2075321A1 (fr) 2007-12-17 2009-07-01 Symrise GmbH & Co. KG Procédé destiné à la fabrication d'un concentré d'arômes et concentré d'arômes
EP2075320A1 (fr) 2007-12-17 2009-07-01 Symrise GmbH & Co. KG Procédé destiné à la fabrication d'un concentré d'arômes et concentré d'arômes
WO2012069295A1 (fr) * 2010-11-26 2012-05-31 Unilever Nv Procédé de préparation de produits à base de thé
JP2013216831A (ja) * 2012-04-12 2013-10-24 Ogawa & Co Ltd 保存性に優れた天然香料の製造方法
DE102015119155A1 (de) * 2015-11-06 2017-05-11 Flavologic Gmbh Verfahren und Vorrichtung zum Herstellen eines Aromastoffkonzentrats aus einem Aromastoff-haltigen Edukt
WO2018110585A1 (fr) * 2016-12-16 2018-06-21 長谷川香料株式会社 Procédé de fabrication de composition aromatique à partir de grains de café torréfiés, et dispositif de capture d'arôme à partir de grains de café torréfiés

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Publication number Priority date Publication date Assignee Title
CN117740976A (zh) * 2023-12-07 2024-03-22 山东京卫制药有限公司 一种高效液相法检测苯乙醇有关物质的分析方法
CN117740976B (zh) * 2023-12-07 2024-08-13 山东京卫制药有限公司 一种高效液相法检测苯乙醇有关物质的分析方法

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