EP0035683B1 - Procédé pour la fabrication de matières aromatiques - Google Patents

Procédé pour la fabrication de matières aromatiques Download PDF

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Publication number
EP0035683B1
EP0035683B1 EP81101285A EP81101285A EP0035683B1 EP 0035683 B1 EP0035683 B1 EP 0035683B1 EP 81101285 A EP81101285 A EP 81101285A EP 81101285 A EP81101285 A EP 81101285A EP 0035683 B1 EP0035683 B1 EP 0035683B1
Authority
EP
European Patent Office
Prior art keywords
tobacco
process according
extract
irradiation
carried out
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP81101285A
Other languages
German (de)
English (en)
Other versions
EP0035683A1 (fr
Inventor
Ursula Brümmer
Volker Heeman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
British American Tobacco Germany GmbH
Original Assignee
BAT Cigarettenfabriken GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BAT Cigarettenfabriken GmbH filed Critical BAT Cigarettenfabriken GmbH
Publication of EP0035683A1 publication Critical patent/EP0035683A1/fr
Application granted granted Critical
Publication of EP0035683B1 publication Critical patent/EP0035683B1/fr
Expired legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/26—Use of organic solvents for extraction

Definitions

  • the invention relates to a process for the production of flavorings using an alcoholic extract obtained from green tobacco plants or parts thereof, containing carotenoids, from which chlorophyll and, if appropriate, the wax-like diterpene components present on the surface of the tobacco plants are removed, and / or by others Plant extracts containing xanthophyll in alcoholic solution.
  • the flavorings produced according to the invention can be used as flavoring tobacco additives.
  • fresh tobacco plants contain various natural substances which, as smoke aroma precursors, influence the tobacco aroma.
  • the surface resin of fresh tobacco plants which can be obtained by briefly washing the plants, contains the valuable diterpenes, especially Duvane, as precursors.
  • the separation of these diterpenes is known from DE-A-29 18 920. The diterpene fractions obtained after this can be added to ready-made tobacco after isolation and purification.
  • Carotenoids which are also aroma precursors, still occur in the tobacco plants themselves.
  • the isolation of these carotenoids in the form of alcoholic extracts is known from Tobacco Science 2, 81 (1958).
  • the surface resin for. B. was removed by washing with methylene chloride.
  • plants can also be used which still contain the surface resin, because u. U.
  • the diterpenes obtained in the surface resin can also be converted into valuable aroma precursors or aroma substances during the treatment according to the invention.
  • Xanthophyll-rich extracts from other plants can also be used, e.g. B. commercially available xanthophyll, which is usually commercially available in paste form.
  • the irradiation is preferably carried out at a wavelength of 220-580 nm.
  • the radiation is usually at room temperature; however, other temperatures are also possible, e.g. B. Temperatures between - 20 ° C and the boiling point of the solvent used.
  • the duration of the radiation depends on the size of the radiation approach, the respective type of carotenoids, which can vary depending on the tobacco plants, and the power of the UV source.
  • the radiation duration is generally from one hour to 10 days, in particular 6-24 hours.
  • the radiation is carried out in the presence of sensitizers.
  • Diterpene fractions isolated from the surface resin for clarifying the chemical structure are already present in the presence of oxygen and sensitizers, i.e. H. irradiated with singlet oxygen, cf. Acta Chemica Scandinavica 1979, pp. 437-442;
  • sensitizers i.e. H. irradiated with singlet oxygen, cf. Acta Chemica Scandinavica 1979, pp. 437-442;
  • aroma precursors or aroma substances are obtained if the radiation is carried out in the absence of the aforementioned sensitizers.
  • the photooxidation then no longer takes place through singlet oxygen, but rather according to a conventional radical mechanism.
  • the flavorings obtained according to the invention have products with numerous carboxyl and carbonyl groups with an otherwise unknown constitution, including ketocarboxylic acids and (mostly lactonized) hydroxycarboxylic acids.
  • the improvement in the properties of the aroma precursors or aroma substances achieved according to this process variant is surprising, since under these process conditions a considerably greater destruction of the aroma substances had to be expected.
  • Nicotinia species such as N. tomentosiformis, glutinosa or sylvestris or known tobacco hybrids and tobacco plants from conventional tobacco cultures can be used as the starting material for the production of the above-mentioned carotenoids.
  • those types of tobacco that are unsuitable as smoking tobacco can be used.
  • Lower alcohols in particular methanol and ethanol, can be used as solvents for the diterpene fraction to be irradiated.
  • the irradiated extracts can, if necessary after prior concentration, directly on finished tobacco z. B. be applied by spraying.
  • the irradiated extracts are fractionated onto the tobacco before they are introduced.
  • the purpose of this fractionation is to separate undesired products with a low boiling point and polymeric products which have a negative effect on the tobacco aroma or can do nothing to improve it.
  • Different methods can be used for the fractionation.
  • a first possibility of fractionation is column chromatography, e.g. B. on silica gel.
  • the irradiated extract is concentrated; the concentrated solution is applied to a silica gel column.
  • various solvents with increasing polarity.
  • the first eluent e.g. B. hexane can be used; the eluate contains hydrocarbons that can be discarded.
  • ether this fraction mainly contains valuable lactones, obtained from hydroxycarboxylic acids formed in the photooxidation of the carotenoids, and also ketones and aldehydes.
  • polar solvents e.g. As methanol, the ⁇ 10 s h acetic acid is added, valuable carboxylic acids, especially ketocarboxylic acids, are isolated. Polymer and possibly highly polar compounds remain in the column.
  • Distillation is another suitable fractionation process.
  • methanol from the irradiated extract at room temperature in a vacuum leads to the removal of unwanted, volatile components.
  • This can be followed by a high vacuum distillation, preferably collecting the fractions which pass at 0.02 Torr at temperatures of up to 100 ° C.
  • Another suitable fractionation method is steam distillation, in which the components that are volatile with water vapor are collected.
  • the process of the invention is preferably carried out by passing an air or oxygen stream through the extract and simultaneously irradiating it with a UV source which provides a wavelength of 220-580 nm.
  • a UV source which provides a wavelength of 220-580 nm.
  • Conventional UV lamps e.g. B. high-pressure mercury lamps or the like.
  • Preparation of an alcoholic carotenoid fraction Parts of fresh green tobacco plants, namely stems and leaves, are washed 2 ⁇ 30 seconds with methylene chloride in an amount of 1 l / kg parts of tobacco to remove the diterpene-rich surface resin.
  • the plant parts thus obtained are homogenized in methanol.
  • the homogenate is centrifuged, the centrifugate is mixed with KOH solution (KOH content 15%, based on the tobacco fresh weight); it is left overnight to destroy the chlorophyll at room temperature.
  • the solution is mixed with a saturated sodium chloride solution with petroleum ether / ether (1: 1).
  • the organic phase is evaporated in vacuo at room temperature.
  • the residue is taken up in methanol, a concentration of 1-50 g of solid / l of methanol being established.
  • 300 ml of an extract obtained above are placed in a 500 ml reactor and irradiated at room temperature with stirring with a high pressure mercury lamp (Philips high pressure burner HPK 125) for 10 hours, whereby a constant stream of synthesis air is bubbled through the solution.
  • a high pressure mercury lamp Philips high pressure burner HPK 125
  • the irradiated extract obtained above is concentrated and placed on a column filled with silica gel.
  • the collected eluates are evaporated in vacuo at room temperature, taken up in ethanol and then sprayed onto ready-made tobacco.
  • Example 2 The procedure is as in Example 1, but about 10 mg of bengal pink are added in the photooxidation stage.
  • the reaction mixture freed from methanol is subjected to steam distillation, the distillate is saturated with NaCl and extracted with diethyl ether.
  • the ether-free extract is applied to ready-made tobacco.
  • a commercially available xanthophyll paste is dissolved in methanol (xanthophyll concentration 1-50 g / l). Irradiation and workup are carried out as in Example 1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (8)

1. Procédé de fabrication de substances aromatiques avec utilisation d'un extrait alcoolique contenant des caroténoïdes qui a été obtenu à partir de plantes vertes de tabac ou de parties de celles-ci et duquel la chlorophylle et, le cas échéant, les éléments diterpéniques cireux, présents à la surface des plantes de tabac, ont été extraits, et/ou d'autres extraits de plantes contenant de la xanthophylle en solution alcoolique, caractérisé en ce que ces extraits sont oxydés avec de l'oxygène par traitement par les radiations ultraviolettes.
2. Procédé selon la revendication 1, caractérisé en ce qu'on procède à l'irradiation à une longueur d'onde de 220 à 580 nm.
3. Procédé selon la revendication 1 ou 2, caractérisé en ce qu'on procède à l'irradiation à la température ambiante.
4. Procédé selon l'une quelconque des revendications 1 à 3, caractérisé en ce qu'on irradie l'extrait pendant une période d'une heure à 10 jours, en particulier de 10 à 24 heures.
5. Procédé selon l'une quelconque des revendications 1 à 4, caractérisé en ce que l'irradiation est effectuée en présence de sensibilisateurs.
6. Procédé selon l'une quelconque des revendications 1 à 4, caractérisé en ce que l'irradiation est effectuée en l'absence de sensibilisateurs.
7. Procédé selon l'une quelconque des revendications 1 à 6, caractérisé en ce qu'on applique l'extrait irradié sur du tabac fini.
8. Procédé selon l'une quelconque des revendications 1 à 7, caractérisé en ce qu'on soumet l'extrait irradié à un fractionnement avant de l'appliquer sur le tabac.
EP81101285A 1980-03-08 1981-02-23 Procédé pour la fabrication de matières aromatiques Expired EP0035683B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3009031 1980-03-08
DE3009031A DE3009031C2 (de) 1980-03-08 1980-03-08 Verfahren zur Herstellung von Aromastoffen für Rauchprodukte

Publications (2)

Publication Number Publication Date
EP0035683A1 EP0035683A1 (fr) 1981-09-16
EP0035683B1 true EP0035683B1 (fr) 1983-11-16

Family

ID=6096679

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81101285A Expired EP0035683B1 (fr) 1980-03-08 1981-02-23 Procédé pour la fabrication de matières aromatiques

Country Status (7)

Country Link
US (1) US4351346A (fr)
EP (1) EP0035683B1 (fr)
AU (1) AU537210B2 (fr)
BR (1) BR8101303A (fr)
CA (1) CA1159641A (fr)
DE (1) DE3009031C2 (fr)
ZA (1) ZA81868B (fr)

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NL8802848A (nl) * 1988-11-18 1990-06-18 Naarden International Nv Werkwijze voor het bereiden van aroma- en reukstoffen.
NL8901317A (nl) * 1989-05-25 1990-12-17 Naarden International Nv Werkwijze voor het bereiden van aroma- en reukstoffen op basis van een of meer carotenoiden als uitgangsmateriaal.
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WO2023119134A1 (fr) 2021-12-20 2023-06-29 Nicoventures Trading Limited Matériau de substrat comprenant des billes pour dispositifs de distribution d'aérosol
US20230309603A1 (en) 2022-03-31 2023-10-05 R.J. Reynolds Tobacco Company Agglomerated botanical material for oral products
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WO2024069542A1 (fr) 2022-09-30 2024-04-04 R. J. Reynolds Tobacco Company Procédé de formation de tabac reconstitué
WO2024079722A1 (fr) 2022-10-14 2024-04-18 Nicoventures Trading Limited Produits en sachet contenant des capsules
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WO2024095162A1 (fr) 2022-11-01 2024-05-10 Nicoventures Trading Limited Procédé de préparation d'un produit en sachet comprenant un sel de nicotine

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FR1206210A (fr) * 1957-08-02 1960-02-08 Reynolds Tobacco Co R Procédé de traitement du tabac
GB1316172A (en) * 1970-03-23 1973-05-09 Ici Ltd Smoking mixture
GB2020538A (en) * 1978-05-12 1979-11-21 British American Tobacco Co Improvements relating to smoking-material additives

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FR1206210A (fr) * 1957-08-02 1960-02-08 Reynolds Tobacco Co R Procédé de traitement du tabac
GB1316172A (en) * 1970-03-23 1973-05-09 Ici Ltd Smoking mixture
GB2020538A (en) * 1978-05-12 1979-11-21 British American Tobacco Co Improvements relating to smoking-material additives

Also Published As

Publication number Publication date
DE3009031A1 (de) 1981-09-17
CA1159641A (fr) 1984-01-03
BR8101303A (pt) 1981-09-08
US4351346A (en) 1982-09-28
AU537210B2 (en) 1984-06-14
AU6805281A (en) 1981-09-17
EP0035683A1 (fr) 1981-09-16
ZA81868B (en) 1982-03-31
DE3009031C2 (de) 1983-04-21

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