EP0822247A2 - Huile aromatique de tabac pratiquement exempte de nicotine et son procédé de préparation - Google Patents

Huile aromatique de tabac pratiquement exempte de nicotine et son procédé de préparation Download PDF

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Publication number
EP0822247A2
EP0822247A2 EP97112959A EP97112959A EP0822247A2 EP 0822247 A2 EP0822247 A2 EP 0822247A2 EP 97112959 A EP97112959 A EP 97112959A EP 97112959 A EP97112959 A EP 97112959A EP 0822247 A2 EP0822247 A2 EP 0822247A2
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EP
European Patent Office
Prior art keywords
tobacco
nicotine
oil
carbon dioxide
extraction
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.)
Withdrawn
Application number
EP97112959A
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German (de)
English (en)
Other versions
EP0822247A3 (fr
Inventor
Adam Dr. Müller
Peter Dr. Swidersky
Heinz Ludwig Lodes
Reiner Scheler
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.)
Mueller Extract Co GmbH
Original Assignee
Mueller Extract Co 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
Priority claimed from DE1996130619 external-priority patent/DE19630619C2/de
Application filed by Mueller Extract Co GmbH filed Critical Mueller Extract Co GmbH
Publication of EP0822247A2 publication Critical patent/EP0822247A2/fr
Publication of EP0822247A3 publication Critical patent/EP0822247A3/fr
Withdrawn legal-status Critical Current

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    • 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
    • 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
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/305—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances of undetermined constitution characterised by their preparation

Definitions

  • the invention relates to a method for producing an essentially nicotine-free tobacco flavor oil according to claims 1 and 14 and an im essential nicotine-free tobacco flavor oil according to claim 27.
  • DE-PS-20 43 537 describes a method for extracting nicotine Tobacco with carbon dioxide.
  • the tobacco is first used Moistened water to increase the solubility of the nicotine.
  • the nicotine is extracted with carbon dioxide in the supercritical state and either by Deposition or removed via sorbents.
  • DE-A-21 42 205 describes a three-stage process for the extraction of Low nicotine tobacco by extraction with supercritical Carbon dioxide is used because in addition to nicotine in the supercritical Carbon dioxide also dissolve flavorings.
  • the Flavorings extracted with dry carbon dioxide from the tobacco and in one Container separated.
  • moist Carbon dioxide is a large part of the nicotine available from tobacco extracted.
  • the extracted flavors again absorbed with supercritical carbon dioxide and onto the tobacco brought.
  • DE-PS-33 34 736 the use of a mixture of nitrogen and Carbon dioxide for nicotine extraction from tobacco is described.
  • the process is based insists that a mixture of carbon dioxide and nitrogen is a selective Represents solvent for nicotine.
  • DE-A-28 44 781 describes a method in which the Solubility of carbon dioxide for nicotine through the addition of ethanol is increased.
  • DE-PS-40 02 784 describes a process for the extraction of Tobacco alkaloids, which initially contain a 2-3 valued organic acid a total of 2 - 6 carbon atoms dissolved in the supercritical carbon dioxide becomes.
  • the organic acid increases the solubility of nicotine.
  • the dissolved nicotine is then over an adsorbent (activated carbon or zeolite) deposited.
  • the solvent carbon dioxide is again with the loaded with organic acid and passed through the tobacco for extraction.
  • Nicotine concentrations have recently become undesirable, as are those with nicotine contaminated aromatic oils are air sensitive and therefore not very well storable and difficult to apply.
  • the product of the invention is a clear tobacco flavor oil, which in is essentially free of nicotine, but otherwise the full aromatic Has properties of the extracted tobacco.
  • the term "in essentially nicotine-free" a product that is less than approx. Contains 0.1% by weight of residual nicotine, but otherwise the full aromatic properties of a tobacco flavor oil.
  • a particular advantage of the tobacco flavor oils according to the invention is that justifies that they are stable in storage under air and also in their application remain stable in large air distribution.
  • This acid is inexpensive, harmless to health and may according to the regulation Tobacco products are added to tobacco.
  • Tobacco aroma oil becomes the corresponding organic acid or its alkali salts dissolved in water.
  • the nicotine content in the Tobacco aroma oil one to two times the amount of acid (mole) compared to the Existing amount of nicotine (mole) dissolved in the tobacco flavor oil in the water.
  • the phases which are not miscible with one another are agitated by intensive stirring or Shake emulsified.
  • the emulsion process is usually carried out for 10 to 20 hours, Maintain vigorous stirring or shaking.
  • the Maintaining the emulsion serves on the one hand to form the corresponding one Nicotine salt and on the other hand the transition of the nicotine salt formed from the organic in the aqueous phase. After emulsification, the phases separated again.
  • a special cylindrical one is used for the emulsification and for the separation Emulsion phase separator 1 used with an attachment 2 (Fig. 1).
  • the essay allows the stirrer 3 to be emulsified by a Ultrasonic transducer 4 to replace, so that the emulsified system for Phase separation can remain in the same vessel.
  • the cylindrical emulsion phase separator 1 is with a heating jacket 5, which is controlled by a thermostat 6 is supplied. The thermostat can be operated via taps 7 + 8 be added or disconnected.
  • the lower, aqueous phase can be 9 be drained.
  • the finished product remains in the separator 1 and can can be filled directly.
  • the stir bar is with several one above the other Stirring elements equipped so that the formation of an optimal emulsion is guaranteed. Shortly before switching off the stirrer, if necessary Sodium chloride added to the emulsion. After emulsification, the Stirrer through the ultrasonic vibrating head 4, which is the phase separation significantly accelerated, replaced. Taps 7 + 8 are opened, and the Emulsion phase separator 1 is heated via the thermostat 6. Of the rod-shaped sound transducer 4 is at around 20-100 kHz optimal frequency operated.
  • the specially used ultrasonic transducer becomes constant or at intervals, alone or simultaneously with the main frequency operated at least one other frequency and thereby ensures that to avoid dead sound zones lying between the antinodes.
  • the aromatic oil obtained with this method has a nicotine content of only still 0.1% by weight to 0.01% by weight. A possibly smaller one Residual water content based on the weight of the aromatic oil can be removed.
  • the product is a clear tobacco flavor oil with a nicotine content of less than 0.1 % By weight received.
  • the smell and the decisive for the aroma of the tobacco Flavor components are still contained in the tobacco aroma oil.
  • the new tobacco aroma oil obtained is characterized in that it is all for the aroma contains necessary components, but the concentration of those previously contained secondary alkaloids such.
  • the new product is characterized in that to the same extent (percentage) like the nicotine concentration also the concentration of Triethylamine, diethylamine, pyrrolidine and piperidine compared to untreated tobacco flavor oil has decreased.
  • This is another one essential advantage of the new compared to the conventional product DE-A-32 18 760, because the amines mentioned form the extreme when smoking carcinogenic nitrosamines.
  • the percentage of amino acids present is also according to the nicotine concentration (percentage) in the new product correspondingly lower.
  • the absence of Proteins and amino acids increase the quality of the smoke taste.
  • the nicotinized aroma oil has compared to the conventional Tobacco aroma oil with e.g. 40% by weight nicotine on average around 5% lower density.
  • the dynamic viscosity is with the new tobacco flavor oil compared to the corresponding tobacco aroma oil with about 40% by weight of nicotine 4-6 times larger.
  • the kinematic viscosity of the new one Tobacco aroma oil is 4-6 times larger than the kinematic viscosity of the corresponding, untreated tobacco flavor oil with about 40% by weight nicotine.
  • the new product has the same conditions compared to conventional tobacco flavor oil with a nicotine content of e.g. 40% a lighter Color, as shown by corresponding spectrophotometric studies.
  • the aim is in any case as little nicotine as possible in addition to all flavor components to extract.
  • the primary extract or the ground tobacco is in a high pressure container 2 (Fig. 2).
  • the CO 2 comes from the storage container 8 and is brought to appropriate pressure and temperature conditions with a pump 7 and a heat exchanger.
  • the carbon dioxide flows through a high-pressure container 1 filled with calcium chloride (anhydrous) powder 1.
  • the prefilter 1 serves to remove traces of water from the carbon dioxide, since the solubility of the nicotine increases with increasing water content in the carbon dioxide rapidly. Pre-dried carbon dioxide thus serves as an extractant.
  • the nicotine which has also been extracted is largely separated into container 3. This is done by passing the extract solution through an aqueous solution containing a 2-3-valent organic acid with 2-6 carbon atoms or their alkali salts.
  • an inorganic acid can also be used for the deposition.
  • the aqueous organic acid can also be applied to a suitable carrier material.
  • citric acid monohydrate has proven itself for nicotine separation for the reasons mentioned in the first method according to the invention.
  • Further traces of water and nicotine which are still present are removed by a filter 4 which is attached in front of the separating container 5.
  • the filter contains a mixture of 50% by weight citric acid monohydrate and 50% by weight calcium chloride anhydrous.
  • a clear tobacco flavor oil (267.6 g) with a nicotine content of approx. 0.068% by weight If the process for the product obtained with the repeated the same solution and a solvent amount of 450 ml 265.3 g of clear Burley aroma oil after treatment in a thin film evaporator with a nicotine content of less than 0.0001% by weight (1 ppm). At The nicotine content of 37.3% by weight was applied once. reduced to about 0.068% by weight by about 548 times. With two Using the process, the nicotine content of the product obtained is lower than 0.0001% by weight with respect to the starting material (37.3% by weight) by about that 373000 times less.
  • a non-filtered Burley tobacco aroma oil with all resins is used as the starting material and waxing and a nicotine content of 40.1%.
  • Tobacco aroma oil according to the traditional method Density at 25 ° C: 0.98 gcm -3 kinematic viscosity at 25 ° C: 138.2 cSt dynamic viscosity at 25 ° C: 135.5 mPas Refractive index at 20 ° C: 1.5139 Nicotine content: 37.3% by weight
  • the carbon dioxide passes in front of the extraction container 2
  • High pressure container 1 which is filled with 500 g calcium chloride powder (anhydrous). After extraction container 2, this happens with flavorings and nicotine loaded carbon dioxide the high pressure container 3.
  • the high pressure container 3 there is a solution of 500 g of citric acid monohydrate in 1 liter of water.
  • the extract solution which is largely freed from nicotine, flows through a further high-pressure container 4, which is filled with a mixture of 500 g calcium chloride and 500 g citric acid powder and frees the extract solution from remaining traces of water or traces of nicotine.
  • the product is separated in the expansion container 5.
  • the CO 2 is liquefied and returned to the process via the pump 7.
  • Tobacco aroma oil according to the traditional method Density at 25 ° C: 0.98 gcm -3 kinematic viscosity at 25 ° C: 51.2 cSt dynamic viscosity at 25 ° C: 50.2 mPas Refractive index at 20 ° C: 1.5110 Nicotine content: 39.3% by weight
  • Tobacco aroma oil produced by the process according to the invention claims 13-25 Density at 25 ° C: 0.93 gcm -3 kinematic viscosity at 25 ° C: 270.6 cSt dynamic viscosity at 25 ° C: 251.3 mPas Refractive index at 20 ° C: 1.4963 Nicotine content: 0.082% by weight

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Manufacture Of Tobacco Products (AREA)
EP97112959A 1996-07-29 1997-07-28 Huile aromatique de tabac pratiquement exempte de nicotine et son procédé de préparation Withdrawn EP0822247A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996130619 DE19630619C2 (de) 1996-07-29 1996-07-29 Im wesentlichen nikotinfreies Tabakaromaöl sowie Verfahren zu dessen Herstellung
DE19630619 1996-07-29

Publications (2)

Publication Number Publication Date
EP0822247A2 true EP0822247A2 (fr) 1998-02-04
EP0822247A3 EP0822247A3 (fr) 1998-11-25

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ID=7801207

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97112959A Withdrawn EP0822247A3 (fr) 1996-07-29 1997-07-28 Huile aromatique de tabac pratiquement exempte de nicotine et son procédé de préparation

Country Status (2)

Country Link
EP (1) EP0822247A3 (fr)
DE (1) DE19654945C2 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102161935A (zh) * 2010-12-31 2011-08-24 广东中烟工业有限责任公司 一种烟草内源性香料及其制备方法和应用
CN103525553A (zh) * 2013-10-23 2014-01-22 红云红河烟草(集团)有限责任公司 一种烟草与香料植物混合精油及其应用
CN106923373A (zh) * 2016-12-30 2017-07-07 中国烟草总公司广东省公司 一种薄荷香型抹香烟及其制备方法
CN109280581A (zh) * 2018-09-20 2019-01-29 云南中烟工业有限责任公司 一种烟草净油的高效制备方法及用途
US11766067B2 (en) 2017-05-15 2023-09-26 Nicoventures Trading Limited Ground tobacco composition

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DE10051427C1 (de) 2000-10-17 2002-06-13 Adam Mueller Verfahren zur Herstellung eines Tetrahydrocannabinol- und Cannabidiol-haltigen Extraktes aus Cannabis-Pflanzenmaterial sowie Cannabis-Extrakte
GB2377218A (en) 2001-05-04 2003-01-08 Gw Pharmaceuticals Ltd Process and apparatus for extraction of active substances and enriched extracts from natural products
AT507187B1 (de) 2008-10-23 2010-03-15 Helmut Dr Buchberger Inhalator
AT508244B1 (de) 2010-03-10 2010-12-15 Helmut Dr Buchberger Inhalatorkomponente
AT510837B1 (de) 2011-07-27 2012-07-15 Helmut Dr Buchberger Inhalatorkomponente
EP2672847B1 (fr) 2011-02-11 2015-04-22 Batmark Limited Élément inhalateur
PL2753202T3 (pl) 2011-09-06 2016-11-30 Podgrzewanie materiału przeznaczonego do palenia
KR101870335B1 (ko) 2011-09-06 2018-07-20 브리티시 아메리칸 토바코 (인베스트먼츠) 리미티드 가열식 끽연 가능 물질
AT511344B1 (de) 2011-10-21 2012-11-15 Helmut Dr Buchberger Inhalatorkomponente
US9282772B2 (en) 2012-01-31 2016-03-15 Altria Client Services Llc Electronic vaping device
GB201207039D0 (en) 2012-04-23 2012-06-06 British American Tobacco Co Heating smokeable material
GB2504076A (en) 2012-07-16 2014-01-22 Nicoventures Holdings Ltd Electronic smoking device
GB2513637A (en) 2013-05-02 2014-11-05 Nicoventures Holdings Ltd Electronic cigarette
GB2513639A (en) 2013-05-02 2014-11-05 Nicoventures Holdings Ltd Electronic cigarette
GB2513638A (en) 2013-05-02 2014-11-05 Nicoventures Holdings Ltd Electronic cigarette
GB201407426D0 (en) 2014-04-28 2014-06-11 Batmark Ltd Aerosol forming component
GB2528673B (en) 2014-07-25 2020-07-01 Nicoventures Holdings Ltd Aerosol provision system
GB2529201A (en) 2014-08-13 2016-02-17 Batmark Ltd Device and method
GB2533135B (en) 2014-12-11 2020-11-11 Nicoventures Holdings Ltd Aerosol provision systems
GB201511349D0 (en) 2015-06-29 2015-08-12 Nicoventures Holdings Ltd Electronic aerosol provision systems
US20170055584A1 (en) 2015-08-31 2017-03-02 British American Tobacco (Investments) Limited Article for use with apparatus for heating smokable material
US11924930B2 (en) 2015-08-31 2024-03-05 Nicoventures Trading Limited Article for use with apparatus for heating smokable material
US20170119046A1 (en) 2015-10-30 2017-05-04 British American Tobacco (Investments) Limited Apparatus for Heating Smokable Material
CA3022340C (fr) 2016-04-27 2021-09-21 Nicoventures Holdings Limited Systeme de fourniture d'aerosol electronique et vaporisateur associe

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE24114C (de) * F. C. GLASER, Königlicher Kommissionsrath in Berlin SW., Lindenstrafse 80 Verfahren zum Verbessern des Tabaks
DE957019C (de) * 1953-08-18 1957-01-24 Martin Brinkmann Kommanditgese Verfahren zur Extraktion von Tabak mit Wasser
DE2142205A1 (de) * 1971-08-23 1973-03-15 Hag Ag Verfahren zur selektiven, aroma erhaltenden extraktion von nikotin aus tabak
EP0081231A2 (fr) * 1981-12-07 1983-06-15 Adam Dr. Müller Procédé pour la production des substances aromatiques à partir d'un extrait de tabac
EP0280817A2 (fr) * 1986-12-29 1988-09-07 Philip Morris Products Inc. Procédé pour éliminer des matières basiques de produits végétaux
EP0440022A2 (fr) * 1990-01-31 1991-08-07 B.A.T. Cigarettenfabriken GmbH Procédé d'extraction des alcaloides du tabac
EP0443761A1 (fr) * 1990-02-23 1991-08-28 R.J. Reynolds Tobacco Company Traitement du tabac

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DE2043537C3 (de) * 1970-09-02 1975-08-07 Studiengesellschaft Kohle Mbh, 4330 Muelheim Verfahren zur Extraktion von Nikotin aus Tabak
DE3218760A1 (de) * 1982-05-18 1983-12-01 Adam Dr. 8630 Coburg Müller Klares tabak-aromaoel, sowie verfahren zu seiner gewinnung aus einem tabakextrakt und dessen verwendung
DE3334736A1 (de) * 1983-09-26 1985-04-04 Kohlensäure-Werke Rud. Buse GmbH & Co, 5462 Bad Hönningen Verfahren zur herstellung von nikotinarmem tabak durch hochdruckextraktion

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE24114C (de) * F. C. GLASER, Königlicher Kommissionsrath in Berlin SW., Lindenstrafse 80 Verfahren zum Verbessern des Tabaks
DE957019C (de) * 1953-08-18 1957-01-24 Martin Brinkmann Kommanditgese Verfahren zur Extraktion von Tabak mit Wasser
DE2142205A1 (de) * 1971-08-23 1973-03-15 Hag Ag Verfahren zur selektiven, aroma erhaltenden extraktion von nikotin aus tabak
EP0081231A2 (fr) * 1981-12-07 1983-06-15 Adam Dr. Müller Procédé pour la production des substances aromatiques à partir d'un extrait de tabac
EP0280817A2 (fr) * 1986-12-29 1988-09-07 Philip Morris Products Inc. Procédé pour éliminer des matières basiques de produits végétaux
EP0440022A2 (fr) * 1990-01-31 1991-08-07 B.A.T. Cigarettenfabriken GmbH Procédé d'extraction des alcaloides du tabac
EP0443761A1 (fr) * 1990-02-23 1991-08-28 R.J. Reynolds Tobacco Company Traitement du tabac

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102161935A (zh) * 2010-12-31 2011-08-24 广东中烟工业有限责任公司 一种烟草内源性香料及其制备方法和应用
CN103525553A (zh) * 2013-10-23 2014-01-22 红云红河烟草(集团)有限责任公司 一种烟草与香料植物混合精油及其应用
CN106923373A (zh) * 2016-12-30 2017-07-07 中国烟草总公司广东省公司 一种薄荷香型抹香烟及其制备方法
US11766067B2 (en) 2017-05-15 2023-09-26 Nicoventures Trading Limited Ground tobacco composition
CN109280581A (zh) * 2018-09-20 2019-01-29 云南中烟工业有限责任公司 一种烟草净油的高效制备方法及用途
CN109280581B (zh) * 2018-09-20 2021-07-30 云南中烟工业有限责任公司 一种烟草净油的高效制备方法及用途

Also Published As

Publication number Publication date
EP0822247A3 (fr) 1998-11-25
DE19654945A1 (de) 1998-03-12
DE19654945C2 (de) 1998-05-20

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