EP0280817A2 - Procédé pour éliminer des matières basiques de produits végétaux - Google Patents

Procédé pour éliminer des matières basiques de produits végétaux Download PDF

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Publication number
EP0280817A2
EP0280817A2 EP87311430A EP87311430A EP0280817A2 EP 0280817 A2 EP0280817 A2 EP 0280817A2 EP 87311430 A EP87311430 A EP 87311430A EP 87311430 A EP87311430 A EP 87311430A EP 0280817 A2 EP0280817 A2 EP 0280817A2
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EP
European Patent Office
Prior art keywords
tobacco
solvent
nicotine
extraction
acid
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EP87311430A
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German (de)
English (en)
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EP0280817B1 (fr
EP0280817A3 (en
Inventor
Harvey J. Grubbs
Ravi Prasad
Tony M. Howell
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Philip Morris Products Inc
Philip Morris USA Inc
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Philip Morris Products Inc
Philip Morris USA Inc
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Application filed by Philip Morris Products Inc, Philip Morris USA Inc filed Critical Philip Morris Products Inc
Priority to AT87311430T priority Critical patent/ATE102446T1/de
Publication of EP0280817A2 publication Critical patent/EP0280817A2/fr
Publication of EP0280817A3 publication Critical patent/EP0280817A3/en
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    • 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
    • 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

Definitions

  • This invention relates to extraction procedures and is particularly directed to a process for the selective removal of basic materials from plant products.
  • the invention may be used for the selective extraction of particular substances from a great variety of plant products. However, it is particularly applicable and will therefore be described in connection with the extraction of nicotine from tobacco.
  • Nicotine has been extracted from tobacco using organic solvents with and without neutralization of the nicotine salt. Representative of such pro Fallss are those disclosed in U.S. Patent Nos. 678,362 (Froehling), 1,196,184 (V Amsterdam-Stuart), 2,048,624 (Roselius), 2,128,043 (Garner), 2,227,863 (Rhodes) and 3,096,773 (Prilly et al.). Nicotine has also been extracted from tobacco with aqueous solutions with and without neutralization of the nicotine salt. Representative of such processes are those disclosed in U.S. Patent Nos.
  • Nicotine has been separated from solutions of tobacco extracts and the nicotine depleted solvent returned to the tobacco. Representative of such processes are those disclosed in U.S. Patent Nos. 283,622 (Liebreich et al.), 802,437 (Wimmer), 2,805,667 (von Bethmann), 3,046,997 (Hind), and 3,139,435 (Staley et al.). Nicotine has also been separated from solutions of tobacco extracts and the depleted solvent saturated with the other components recycled to the extraction vessel. Representative of such processes are those disclosed in U.S. Patent Nos. 1,294,310 (Sayre et al.), 1,577,768 (Smith), 1,813,333 (Andrews), 3,396,735 (von Bethmann) and 3,612,066 (Jones).
  • Nicotine has been transferred from tobacco to a substrate without the use of a solvent by contacting the tobacco intimately with a substrate which has been treated with an acid as disclosed in United States Patent No. 4,215,706 (Larson). This process maybe carried out with or without heat.
  • United States Patent No-4,153,063 discloses a process for removing nicotine from tobacco in which tobacco is contacted with an extraction solvent in a supercritical state.
  • moist tobacco is extracted with a solvent in a supercritical state. Thereafter the solvent is evaporated.
  • aroma components are also removed along with nicotine in this single step extraction process, a multi-step process has been suggested.
  • dry tobacco is extracted with a solvent in the supercritical state to remove the aroma components.
  • the tobacco is moistened and again extracted with a solvent in the supercritical state to remove nicotine which is separated by either evaporating the solvent, contacting the solvent in a separate vessel with an acid, or adsorbing the nicotine on an active carbon column.
  • the stored aroma components from the first step are redissolved in a supercritical solvent and returned to the tobacco.
  • This multi-step extraction process is expensive and time consuming. In addition, the prolonged handling of the aroma components may adversely affect their properties.
  • This invention provides a process for removing nicotine from tobacco without also removing the desirable aroma generating components.
  • Tobacco is extracted with a solvent either in the supercritical state or in the liquid state. Thereafter, nicotine is selectively removed from the enriched solvent by passing the solvent through a trap containing a non-volatile acid which is not soluble in the extraction solvent.
  • the trap may be contained on a support medium.
  • the solvent, depleted of nicotine and enriched in the other components, is then recycled to the tobacco to extract nicotine again.
  • the tobacco may be pretreated with a chemically basic (alkaline) compound which does not significantly react with the tobacco components under ambient conditions but rather is effective in increasing the amount of extractable nicotine under the conditions of the extraction process.
  • a chemically basic (alkaline) compound which does not significantly react with the tobacco components under ambient conditions but rather is effective in increasing the amount of extractable nicotine under the conditions of the extraction process.
  • Pretreat ment of the tobacco with a basic compound neutralizes nicotine salts and permits the extraction process to be carried out under milder conditions.
  • adsorption media full flavor tobacco filler, reconstituted leaf materials, tobacco stems, cotton cloth, cellulose, carbon, cocoa shells, other plant by-products, porous ceramic, porous metal, etc.
  • aqueous absorption media water, aqueous acid, aqueous salt, etc.
  • FIG. 1 illustrates the apparatus for removing basic materials.
  • FIG. 1 illustrates one preferred apparatus for removing nicotine from tobacco and tobacco blends.
  • Extraction vessel 1 is filled with a sample of tobacco and entrapment vessels 2 and 3 and filled with an acid impregnated support medium or water, preferably containing some acid.
  • An extraction solvent is supplied to vessel 1 which is connected to a pump 4 and a mass flow meter 5.
  • the pressure in the vessel is controlled by means of a fill pump (not shown) and the temperature is controlled by means of heat exchanger 6.
  • the extraction solvent enters the top of the extraction vessel, passes downwardly through the sample and leaves at the bottom of the vessel. In passing through the sample, the extraction solvent becomes enriched with components of the sample.
  • the solvent is then circulated through either trap 2 or trap 3, or both, again being introduced from the top, and then passing downwardly and exiting at the bottom.
  • the entrapment time may be split between traps 2 and 3.
  • the nicotine in the solvent reacts with the acid and becomes trapped therein while the remaining aroma components in the solvent pass through the trap or traps freely.
  • the solvent, depleted of nicotine and enriched in the other components, is then returned into the cycle by recirculating it to the extraction vessel.
  • the extraction vessel is preferably designed for radial flow or for axial flow of solvent.
  • the entrapment vessels are preferably both designed for radial flow or axial flow but need not be of the same design as the extraction vessel.
  • a radial flow of solvent will minimize compaction of solid material in a vessel and may allow for lower pressure drops within each vessel.
  • Persons skilled in the art will recognize that many directions of flow will be effective, e.g., flow from bottom to top, top to bottom or inward or outward radially in each vessel.
  • the pump can be placed on any of several lines in the system.
  • An especially preferred procedure makes it possible to contain both the tobacco sample and a relatively small volume of entrapment material in the same extraction vessel.
  • the entrapment material is placed in the bottom portion of the extraction vessel, a porous plate is placed on top of the trap and the tobacco is loaded into the extraction vessel on top of and supported by the porous plate.
  • the entrapment vessels 2 and 3 are removed from the flow system by valve adjustment.
  • the extraction of the tobacco sample is then carried out as before by introducing the solvent into the top of the extraction vessel and passing it downwardly through the sample until it exits at the bottom of the vessel.
  • One advantage of this process is that no additional vessel is necessary to contain a relatively large quantity of adsorption material to trap the nicotine.
  • the ability to carry out the extraction in a single vessel results in a more economical process for the above reasons and also because the solvent to tobacco ratio can be significantly lowered.
  • the ability to use less solvent also results in less degradation and loss of the aroma producing components and consequently in an improved tobacco product.
  • the tobacco may be pretreated with a chemically basic compound which does not significantly react with the tobacco components under ambient conditions but rather is activated under the conditions of the extraction process. Nicotine is thus liberated from its salts and immediately taken up in the extraction solvent before other base induced chemistry is initiated within the tobacco. Since the solubility of the nicotine free base is generally higher than that of the nicotine salts in the extraction solvents of choice, the extraction process may be carried out under milder conditions. Pretreatment can include spraying or soaking the tobacco with the basic compound or a suitable solution thereof.
  • a number of extraction solvents having solvent capacity for nicotine in both their liquid and gaseous phases can be employed to reduce the nicotine content of tobacco.
  • Carbon dioxide in the supercritical state is the preferred solvent in this invention.
  • CFCI CF2, CH 3 -CF 3 , octafluorocyclobutane and hydrocarbons including up to about 5 carbon atoms such as propane, butane, pentane; other useful solvents include N 2 0, SF6 and argon.
  • Mixtures of solvents or additives or co-solvents may be used to obtain improved solvent characteristics.
  • water, ammonia, or aqueous ammonia can be mixed with the extraction solvent to obtain improved solvent characteristics.
  • Carbon dioxide is the preferred solvent because it is a naturally occurring compound and leaves no non-tobacco residue in the extracted tobacco.
  • a solvent in the supercritical state is a solvent in the gas phase at a sufficiently high temperature so that it cannot be liquified by an increase in pressure.
  • a solvent in the subcritical state is a solvent which can be liquified by an increase in pressure.
  • Supercritical carbon dioxide is carbon dioxide which is above its critical temperature, i.e., above 31.3°C, and above its critical pressure, i.e., above about 70 atmospheres. Extraction with carbon dioxide in the supercritical state is carried out at a pressure in the range of from about 70 to about 1500 atmospheres and at a temperature in the range of from just above the critical temperature to about 120°C.
  • the range of temperature and pressure for the supercritical state of other useful solvents are of generally the same order of magnitude.
  • the preferred acids for use in this invention are acids which are non-volatile and non-soluble in the extraction solvent under the conditions of the extraction.
  • Useful acids are sulfuric, phosphoric and nitric.
  • Other useful acids include polycarboxylic acids such as tartaric, citric, maiic, malonic, succinic and glutamic.
  • Monovalent salts, such as the alkali metal salts, of the above acids are generally preferred because these salts are less volatile and less soluble in the solvent.
  • a preferred salt of an acid is monopotassium citric acid.
  • Monoammonium and diammonium salts of the above acids may also be used.
  • Polyvalent salts of the above acids are also useful but are less efficient in trapping nicotine.
  • the acid in the trap is preferably, though not necessarily, in contact with a support medium, which does not impede the flow of the solvent.
  • the acid may be impregnated on, deposited on, or otherwise in contact with the support medium.
  • Useful support media are carbon, tobacco filler, reconstituted leaf materials, tobacco stems, cotton cloth, cellulose, cocoa shells, other plant by-products, porous ceramic, porous metal and the like.
  • the tobacco stems may be long stems, cut and rolled, shredded, expanded, treated or untreated.
  • Especially preferred support media are shredded tobacco stems and cocoa shells.
  • the support medium for the acid may even be water, as'in the case where the solvent is bubbled through an aqueous solution of the acid.
  • a preferred trap material is an aqueous solution of citric acid.
  • An especially preferred trap material is an aqueous solution of monopotassium citrate.
  • the ratio of acid to nicotine may range from about 10:1 to about 1:1 and preferably from about 4.5:1 to 1.5:1.
  • the concentration of the acid in the support medium is not critical. The concentration should be high enough to minimize the volume of support medium required within the vessel but low enough not to impede the flow characteristics of the solvent through the support medium.
  • the concentration of acid in the support medium may vary but in the case of tobacco stems the concentration generally ranges from about 5% by weight to about 40% by weight and preferably is about 15% by weight. Higher acid concentrations, i.e., saturated or crystalline forms are not excluded.
  • the chemical bases for use in this invention for pretreating tobacco are bases which do not significantly react with the tobacco components under ambient conditions. Chemical bases which do significantly react with the tobacco components under ambient conditions may initiate base catalyzed chemistry in the tobacco, blackening the tobacco and otherwise adversely affecting its smoking characteristics. Rather, the preferred base is one which is effective in increasing the amount of extracted nicotine without excessively increasing the extraction of flavor constituents. Such a base may react with the components in the tobacco under the conditions of the extraction process. In this way, nicotine is liberated from its salts and immediately taken up in the extraction solvent before other base induced chemistry is initiated within the tobacco. Since the solubility of the nicotine free base is higher than that of the nicotine salts in the extraction solvent, one may carry out the extraction process under milder conditions.
  • Chemical bases which do not significantly react under ambient conditions but are activated under the conditions of the extraction process include ammonium bicarbonate, sodium or potassium carbonate or bicarbonate, glycosylamines, N-glycosides of aldoses, N-glycosides of ketoses and the like.
  • bases are useful in practicing this invention, including ammonia, aqueous ammonia, trimethyl amine and triethyl amine, which can be effective in increasing the amount of extractable nicotine under the extraction conditions, although some such compounds in some concentrations may adversely affect the subjective characteristics of the tobacco.
  • bases which liberate nicotine from its acid salts are effective in practicing this invention, especially bases with a pK a greater than about 7.2 and less than about 10.
  • Com binations of suitable bases are also within the scope of the invention.
  • a glycosylamine useful in the present invention- is illustrated by the following formula: where R is a hydrogen, methyl, or methylol substituent.
  • Other glycosylamine compounds include 1-amino-1-deoxymannose (mannosylamine), 1-amino-1-deoxyribose (ribosylamine), 1-amino-1-deoxygalactose (galactosylamine), 1-amino-1-deoxyrhamnose (rhamnosylamine), 1-amino-1-deoxyfucose (fucosylamine), 1-amino-1-deoxyxylose (xylosylamine), 1-amino-1-deoxyarabinose (arabinosylamine), 1-amino-1-deoxylyxose (lyxosylamine), and the like.
  • glycosylamine compounds included in this invention are, in pure form, stable and odorless compounds at ambient temperatures.
  • the glycosylamine compounds decompose at a relatively low pyrolysis temperature (e.g., 200°-300°C.) to release ammonia, pyrazine and related compounds.
  • Ammonia-derived glycosylamines with an insubstituted amino-group are more stable than glycosylamines in which the amino group is substituted (-NHR or NR 2 ). If the amino group is an amino acid structure, then there is a self-catalyzed Amadori Rearrangement, i.e., a conversion of N-glycoside of aldose sugar to an amine derivative of the corresponding ketose, in addition to other side-reactions which occur at room temperature.
  • Another preferred form of the invention includes pretreating tobacco by spraying it with an aqueous solution of ammonium bicarbonate.
  • Ammonium bicarbonate is useful if applied at about 1% of the dry weight of tobacco (mass/mass) and can be applied at up to 3% of the dry weight of tobacco.
  • the resulting tobacco, after extraction, is generally less harsh than non-pretreated tobacco.
  • Neutralization of nicotine salts may also be carried out by contemporaneously adding a source of base during the supercritical extraction such that neutralization and extraction is nicotine occur simultaneously and no significant base-induced chemistry within the tobacco is initiated.
  • an acid-containing trap is prepared by impregnating an aqueous solution of an acid such as monopotassium citric acid into a support such as expanded tobacco stems.
  • the entrapment material is then placed in an extraction vessel, a porous plate placed on top of the acid-containing trap material and the tobacco to be extracted is loaded on top of the plate.
  • the vessel is charged with solvent, the pressure is brought to 260 atmospheres and the temperature is brought to 70 C.
  • the tobacco to be extracted is adjusted to contain an oven volatile content of about 25%.
  • the percentage of oven volatiles (%OV) in the tobacco is a measure of the moisture content plus a minor fraction of other components and is determined as follows:
  • the tobacco is then traversed with an extraction solvent such as carbon dioxide in the supercritical state, and nicotine and other components are dissolved in the extraction solvent.
  • the enriched supercritical solvent is then passed through the acid containing trap wherein the solvent is freed of nicotine.
  • the supercritical solvent, depleted of nicotine and enriched in other components, is then recycled to the tobacco.
  • the aroma-generating components are extracted from the tobacco only during the initial stages of the cycle since the solvent rapidly becomes saturated with these components. Because nicotine is continuously removed from the solvent, upon recycling the solvent is able to extract additional amounts of nicotine from the tobacco.
  • the process is carried out until the desired level of nicotine reduction in the tobacco is achieved. Usually 30 to 60 minutes is sufficient.
  • An advantage of this process is that principally the nicotine is removed from the supercritical solvent and the aroma-generating components are substantially preserved.
  • Valve and instrumentation hardware may be arranged to allow (a) by-pass of the CO 2 flow to all vessels, (b) CO 2 flow from an extraction vessel to any entrapment vessel, (c) CO 2 flow both upflow and downflow in any vessel, (d) faster turn-around time, (e) use of both large and small CO 2 fill pumps and (f) pressure drop instrumentation for up and down flow differential pressure measurement in the entrapment vessels.
  • the flow of CO 2 is in the opposite direction from the force of gravity in the upflow mode and in the same direction in the downflow mode.
  • the extraction vessel may be bypassed during the CO 2 fill and heat period, and the CO2 flow directed only through the entrapment vessels. Once extraction process conditions are reached, the CO z flow is then directed through the extraction vessel or vessels. Extraction process conditions are reached quickly (4-8 minutes). In an experiment using this process, the beginning of each extraction run was counted when process conditions were reached (temperature, pressure) and the end of each run was counted when the required amount of CO 2 mass (m/m, mass of extraction solvent/mass of tobacco) has traversed the tobacco.
  • Table 1 illustrates the results of extraction runs carried out using carbon as an adsorbent support.
  • Table 2 illustrates the results from extraction runs carried out using potassium-citrate treated stems as the adsorbent support.
  • a high stems to tobacco ratio e.g., in excess of about 2:1 gives a "stemmy" character to the extracted tobacco.
  • Shredded stems are the preferred stem type for an adsorbent support. Use of cut and rolled stems probably results in a pressure drop problem and use of long stems results in poor nicotine extraction.
  • Table 3 shows the results from extraction runs using potassium citrate treated full flavor American blend tobacco as the adsorbent support.
  • Table 4 shows the results from extraction runs using non-tobacco adsorbent supports.
  • cocoa shells as an adsorbent support gave a nicotine removal of 96.9% using a single entrapment column.
  • Subjectives were characterized as acceptable, tobacco like, slightly burnt and sweet with no mouthcoating (Run-30, Table 4).
  • cocoa shells as an adsorbent support also permits the transfer of desirable flavor attributes from one natural substrate (cocoa shells) to another (tobacco).
  • Table 5 illustrates the results from extraction runs carried out using unwashed coarse shredded stems, unwashed fine shredded stems and washed fine shredded stems as the adsorbent support.
  • Table 6 illustrates the results of a number of extraction runs carried out using washed ' fine shredded Bright stems.
  • Table 7 illustrates the results from extraction runs carried out utilizing 2% ammonium bicarbonate pretreatment of the tobacco filler.
  • Table 8 illustrates the results from extraction runs carried out using a single vessel design in the upflow and downflow modes.
  • the flow of carbon dioxide In the upflow mode, the flow of carbon dioxide is in the opposite direction as the force of gravity and in the downflow mode, the flow of carbon dioxide is in the same direction as the force of gravity.
  • the incipient fluidization velocity is about 1.1 cmisec and the pressure drop does not become significant until up to about 1.6 cm/sec.
  • Table 8 also illustrates the relationship between m/m and extraction time.
  • the tobacco was pretreated with potassium citrate to convert nicotine to its salt.
  • the tobacco solubles were extracted with supercritical CO2 at 260 atmospheres and 55°C.
  • Subjective rating was based on a value of "zero" for unextracted full flavor American blend tobacco. A positive value indicates an improved rating.
  • the oven volatiles of the tobacco filler in the extraction vessel decreased when the oven volatiles of the stems were 25% and 35%. when the oven volatiles of the stems were 45% and 55%, the results were inconclusive.
  • Each of the entrapment vessels 2 and 3 in Figure 1 was loaded with 2.2 kg of cotton cloth which were impregnated with 2 liters of an aqueous solution containing 920.8g monopotassium citrate. 12 Kg of full flavor American blend cigarette filler tobacco (25% OV) was placed in extraction vessel 1.
  • the supercritical C02 was brought to 70°C and 260 bar. Then the valve to the first trap was opened and the stream of supercritical CO 2 was circulated through the extractor and the first trap for 15 minutes. At the end of this time, the valve to the second trap was opened and the valve to the first trap was closed. The flow of supercritical CO z was circulated to the second trap for an additional period of 15 min. At the completion of 30 minutes total extraction time, the circulation was stopped and the CO 2 was removed from the system. Tobacco blend and entrapment materials were removed from the system and submitted for nicotine analysis. A reduction in nicotine content of the tobacco blend of 77.4% was obtained. The tobacco blend retained a strong characteristic aroma which was not different from the unextracted blend.
  • Tobacco product (burley) and entrapment material (expanded stems) were removed and submitted for nicotine analysis.
  • the burley tobacco product had a reduction in nicotine content of 92.4%.
  • Analysis of the expanded stem entrapment material yielded a corresponding increase in nicotine content.
  • the burley tobacco product retained a strong characteristic aroma which was not different subjectively from the unextracted burley tobacco.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Manufacture Of Tobacco Products (AREA)
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  • Superconductors And Manufacturing Methods Therefor (AREA)
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EP87311430A 1986-12-29 1987-12-24 Procédé pour éliminer des matières basiques de produits végétaux Revoked EP0280817B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT87311430T ATE102446T1 (de) 1986-12-29 1987-12-24 Verfahren zur entfernung von basischen materialien aus pflanzenprodukten.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US94710286A 1986-12-29 1986-12-29
US947102 1986-12-29

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EP0280817A2 true EP0280817A2 (fr) 1988-09-07
EP0280817A3 EP0280817A3 (en) 1990-05-16
EP0280817B1 EP0280817B1 (fr) 1994-03-09

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EP87311430A Revoked EP0280817B1 (fr) 1986-12-29 1987-12-24 Procédé pour éliminer des matières basiques de produits végétaux

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EP (1) EP0280817B1 (fr)
JP (1) JP2694253B2 (fr)
AT (1) ATE102446T1 (fr)
AU (1) AU612128B2 (fr)
BR (1) BR8707110A (fr)
CA (1) CA1317961C (fr)
DE (1) DE3789300D1 (fr)
FI (1) FI88453C (fr)
ZA (1) ZA879384B (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4967771A (en) * 1988-12-07 1990-11-06 R. J. Reynolds Tobacco Company Process for extracting tobacco
DE4002784C1 (fr) * 1990-01-31 1991-04-18 B.A.T. Cigarettenfabriken Gmbh, 2000 Hamburg, De
US5025812A (en) * 1989-08-10 1991-06-25 R. J. Reynolds Tobacco Company Tobacco processing
US5031644A (en) * 1989-12-29 1991-07-16 R. J. Reynolds Tobacco Company Tobacco expansion process and product
US5065775A (en) * 1990-02-23 1991-11-19 R. J. Reynolds Tobacco Company Tobacco processing
US5076293A (en) * 1989-06-19 1991-12-31 R. J. Reynolds Tobacco Company Process and apparatus for the treatment of tobacco material
US5095923A (en) * 1991-04-11 1992-03-17 R. J. Reynolds Tobacco Company Tobacco expansion process using 1,1,1,2-tetrafluoroethane
US5131414A (en) * 1990-02-23 1992-07-21 R. J. Reynolds Tobacco Company Tobacco processing
US5234008A (en) * 1990-02-23 1993-08-10 R. J. Reynolds Tobacco Company Tobacco processing
US5435325A (en) * 1988-04-21 1995-07-25 R. J. Reynolds Tobacco Company Process for providing tobacco extracts using a solvent in a supercritical state
EP0822247A2 (fr) * 1996-07-29 1998-02-04 Müller Extract Company GmbH Huile aromatique de tabac pratiquement exempte de nicotine et son procédé de préparation
DE19630619A1 (de) * 1996-07-29 1998-02-05 Mueller Extract Co Gmbh Im wesentlichen nikotinfreies Tabakaromaöl sowie Verfahren zu dessen Herstellung
EP1542555A1 (fr) * 2002-07-18 2005-06-22 Phasex Corporation Reduction d'ingredients dans le tabac
WO2011110843A1 (fr) 2010-03-09 2011-09-15 British American Tobacco (Investments) Limited Procédés d'extraction et d'isolation de constituants de matériau cellulosique
WO2018210677A1 (fr) * 2017-05-15 2018-11-22 British American Tobacco (Investments) Limited Procédé de fabrication d'un extrait de tabac
US10405571B2 (en) 2015-06-26 2019-09-10 Altria Client Services Llc Compositions and methods for producing tobacco plants and products having altered alkaloid levels
CN114868763A (zh) * 2022-05-13 2022-08-09 湖南省烟草公司郴州市公司 一种烟草降碱剂及其制备方法和应用
US11766067B2 (en) 2017-05-15 2023-09-26 Nicoventures Trading Limited Ground tobacco composition

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5497792A (en) * 1987-11-19 1996-03-12 Philip Morris Incorporated Process and apparatus for the semicontinuous extraction of nicotine from tobacco
EP1815899B1 (fr) * 2004-10-28 2011-07-20 Japan Tobacco, Inc. Procédé d'extraction d un composant du matériau à traiter et appareil utilisé dans le procédé
WO2019229704A1 (fr) * 2018-05-31 2019-12-05 Radient Technologies Inc. Procédé permettant de réduire la nicotine dans une biomasse de tabac et composition de tabac
CN113115976B (zh) * 2021-03-11 2022-07-19 浙江中烟工业有限责任公司 一种烟碱盐的批量制备方法及其在电子烟中的应用

Citations (5)

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FR397021A (fr) * 1907-12-11 1909-04-27 Tabacs Desintoxiques En Failli Procédé et installation pour la dénicotinisation des tabacs
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US5435325A (en) * 1988-04-21 1995-07-25 R. J. Reynolds Tobacco Company Process for providing tobacco extracts using a solvent in a supercritical state
US4967771A (en) * 1988-12-07 1990-11-06 R. J. Reynolds Tobacco Company Process for extracting tobacco
US5076293A (en) * 1989-06-19 1991-12-31 R. J. Reynolds Tobacco Company Process and apparatus for the treatment of tobacco material
US5025812A (en) * 1989-08-10 1991-06-25 R. J. Reynolds Tobacco Company Tobacco processing
US5031644A (en) * 1989-12-29 1991-07-16 R. J. Reynolds Tobacco Company Tobacco expansion process and product
US5119835A (en) * 1990-01-31 1992-06-09 B.A.T. Cigarettenfabriken Gmbh Method for extracting tobacco alkaloids
EP0440022A3 (en) * 1990-01-31 1991-10-23 B.A.T. Cigaretten-Fabriken Gmbh Process for extracting alkaloids from tobacco
EP0440022A2 (fr) * 1990-01-31 1991-08-07 B.A.T. Cigarettenfabriken GmbH Procédé d'extraction des alcaloides du tabac
DE4002784C1 (fr) * 1990-01-31 1991-04-18 B.A.T. Cigarettenfabriken Gmbh, 2000 Hamburg, De
US5065775A (en) * 1990-02-23 1991-11-19 R. J. Reynolds Tobacco Company Tobacco processing
US5131414A (en) * 1990-02-23 1992-07-21 R. J. Reynolds Tobacco Company Tobacco processing
US5234008A (en) * 1990-02-23 1993-08-10 R. J. Reynolds Tobacco Company Tobacco processing
US5095923A (en) * 1991-04-11 1992-03-17 R. J. Reynolds Tobacco Company Tobacco expansion process using 1,1,1,2-tetrafluoroethane
DE19654945C2 (de) * 1996-07-29 1998-05-20 Mueller Extract Co Gmbh Im wesentlichen nikotinfreies Tabakaromaöl sowie Verfahren zu dessen Herstellung
DE19630619A1 (de) * 1996-07-29 1998-02-05 Mueller Extract Co Gmbh Im wesentlichen nikotinfreies Tabakaromaöl sowie Verfahren zu dessen Herstellung
DE19654945A1 (de) * 1996-07-29 1998-03-12 Mueller Extract Co Gmbh Im wesentlichen nikotinfreies Tabakaromaöl sowie Verfahren zu dessen Herstellung
EP0822247A2 (fr) * 1996-07-29 1998-02-04 Müller Extract Company GmbH Huile aromatique de tabac pratiquement exempte de nicotine et son procédé de préparation
DE19630619C2 (de) * 1996-07-29 1998-07-09 Mueller Extract Co Gmbh Im wesentlichen nikotinfreies Tabakaromaöl sowie Verfahren zu dessen Herstellung
EP0822247A3 (fr) * 1996-07-29 1998-11-25 Müller Extract Company GmbH Huile aromatique de tabac pratiquement exempte de nicotine et son procédé de préparation
US10045557B2 (en) 2002-07-18 2018-08-14 Us Smokeless Tobacco Co. Reduction of constituents in tobacco
EP1542555A4 (fr) * 2002-07-18 2005-09-28 Phasex Corp Reduction d'ingredients dans le tabac
US7798151B2 (en) 2002-07-18 2010-09-21 Us Smokeless Tobacco Co. Reduction of constituents in tobacco
US8555895B2 (en) 2002-07-18 2013-10-15 U.S. Smokeless Tobacco Company Llc Reduction of constituents in tobacco
EP1542555A1 (fr) * 2002-07-18 2005-06-22 Phasex Corporation Reduction d'ingredients dans le tabac
WO2011110843A1 (fr) 2010-03-09 2011-09-15 British American Tobacco (Investments) Limited Procédés d'extraction et d'isolation de constituants de matériau cellulosique
US9022040B2 (en) 2010-03-09 2015-05-05 British American Tobacco (Investments) Limited Methods for extracting and isolating constituents of cellulosic material
EP2544560B1 (fr) 2010-03-09 2017-12-20 British American Tobacco (Investments) Limited Procédés d'extraction et d'isolation de constituants de matériau cellulosique
US10405571B2 (en) 2015-06-26 2019-09-10 Altria Client Services Llc Compositions and methods for producing tobacco plants and products having altered alkaloid levels
WO2018210677A1 (fr) * 2017-05-15 2018-11-22 British American Tobacco (Investments) Limited Procédé de fabrication d'un extrait de tabac
RU2730154C1 (ru) * 2017-05-15 2020-08-19 Бритиш Америкэн Тобэкко (Инвестментс) Лимитед Способ получения табачного экстракта
US11766067B2 (en) 2017-05-15 2023-09-26 Nicoventures Trading Limited Ground tobacco composition
CN114868763A (zh) * 2022-05-13 2022-08-09 湖南省烟草公司郴州市公司 一种烟草降碱剂及其制备方法和应用

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EP0280817B1 (fr) 1994-03-09
FI88453B (fi) 1993-02-15
AU612128B2 (en) 1991-07-04
JPS63229102A (ja) 1988-09-26
FI875673A (fi) 1988-06-30
EP0280817A3 (en) 1990-05-16
BR8707110A (pt) 1988-08-02
AU8310987A (en) 1988-06-30
ATE102446T1 (de) 1994-03-15
FI88453C (fi) 1993-05-25
DE3789300D1 (de) 1994-04-14
ZA879384B (en) 1988-09-28
CA1317961C (fr) 1993-05-18
FI875673A0 (fi) 1987-12-22
JP2694253B2 (ja) 1997-12-24

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