US3390685A - Process for extracting substances from plant particles - Google Patents

Process for extracting substances from plant particles Download PDF

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US3390685A
US3390685A US533023A US53302366A US3390685A US 3390685 A US3390685 A US 3390685A US 533023 A US533023 A US 533023A US 53302366 A US53302366 A US 53302366A US 3390685 A US3390685 A US 3390685A
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tobacco
nicotine
water
organic solvent
solvent
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Bethmann Max Freiherr Von
Lipp Gerhard
Bayer Helmut
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Eresta Warenhandels GmbH
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Eresta Warenhandels GmbH
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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
    • A24B15/241—Extraction of specific substances
    • A24B15/243—Nicotine
    • 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
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/26—Use of organic solvents for extraction

Definitions

  • This invention generally relates to extraction procedures and is particularly directed to a process for the selective separation of particular basic and/or acid constituents from solid plant particles by first extracting the plant particles with an organic solvent which is essentially insoluble in water and thereafter subjecting the enriched solvent to extraction with an aqueous solution of acidic or basic reaction. 7
  • the nicotine is removed from the solvent-nicotine system, for example, by washing with acids or aqueous salt solutions. Since, as stated, the solvent, after the removal of the nicotine, is recycled to the tobacco, it cannot be avoided in these prior art processes that a portion of the acids or salts in dissolved or suspended form are incorporated into the tobacco and negatively influence the quality of the latter. Further, a portion of the soluble tobacco constituents or components, other than nicotine, which are leached by the solvent remain in the solution which is used for removing the nicotine from the solvent and are thus lost from the tobacco. This again seriously detracts from the tobacco quality.
  • U.S. Patent 3,046,997 discloses a procedure for the nicotine removal from tobacco, according to which the tobacco is extracted by means of organic solvents which are miscible with water to a limited extent only.
  • the organic phase which is separated from the tobacco is subsequently subjected to a liquid-liquid extraction with aqueous solutions of inorganic salts and acids and the nicotine is separated from the aqueous solution by renewed solvent extraction.
  • This process has the advantage that the tobacco does not come into direct contact with the water.
  • salts, and in particular inorganic mineral acids whose solubility in organic solvents is relatively high are introduced into the tobacco when the organic phase is recycled to the latter.
  • the mineral acids which thus are incorporated into the tobacco structure upon recycling of the organic solvent, form salts with the nicotine of the tobacco. Contrary to nicotine salts of organic acids, the nicotine salts of mineral acids have an extremely low solubiilty in organic solvents. Consequently, even prolonged extraction with organic solvents does not result in a satisfactory denicotinization of the tobacco.
  • the mineral acids thus fix the nicotine on the tobacco in a certain manner, instead of removing it.
  • Another object of this invention is to provide a process of the indicated kind which lends itself to continuous operation.
  • Genera-11y it is an object of the invention to improve on the art of selective removal of substances from solid plant particles by extraction as presently practiced.
  • the tobacco is first extracted with an organic solvent to remove nicotine from the tobacco.
  • the solution thus obtained is thereafter extracted with water which is enriched or essentially saturated with those tobacco substances which are soluble in the organic solvent and water, except for nicotine, whereby an aqueous nicotine solution is obtained.
  • the aqueous nicotine solution is then subjected to ion exchange to remove the nicotine therefrom.
  • the aqueous solution used for extracting the organic nicotine-containing solvent should be enriched or essentially saturated with substances emanating from the respective plant particles such as organic acids contained in tobacco.
  • the organic solvent should be miscible with water to a limited extent only, a characteristic which may be expressed in different language by stating that the solvent should be essentially insoluble in water.
  • the organic solvent When the tobacco is extracted with the organic solvent, not only nicotine but a number of other soluble tobacco constituents are dissolved from the tobacco. In order to avoid loss of such other constituents from the tobacco, the organic solvent is repeatedly refused for extraction purposes until the concentration of these other constituents in the organic solvent has reached a value so that upon drying of the treated tobacco to remove adhering solvent by evaporation, the amount of such constituents original- 1y dissolved from the tobacco by the solvent is again restored to the tobacco.
  • the concentration of the tobacco constituents which are soluble and present in the aqueous phase and which are not removed from the aqueous phase by ion exchange should be so high that a solubility equilibrium is created between the organic and the aqueous phase.
  • the aqueous phase does not contain any constituents which are extraneous to tobacco so that after the nicotine has been removed from the aqueous phase by ion exchange, any suitable portion of the aqueous phase may be separated and added to the extracted tobacco, for example, for conditioning purposes. The removed part of water may then be replaced by a corresponding amount of fresh Water.
  • FIG. 1 is a diagrammatical representation of the inventive process principle
  • FIG. 2 shows diagrammatically a preferred embodiment for a plant for the continuous performance of the inventive process.
  • a pump 1 which feeds organic solvent through the conduit 10 into extraction means 2 designed for the extraction of a solid by a liquid.
  • the arrangement furthermore comprises a liquid-liquid extractor 3 which is connected with the solid-liquid extractor 2 by means of the conduit 11.
  • a further pump 4 feeds aqueous solution through the conduit 12 into the liquidliquid extractor 3.
  • Aqueous liquid emanating from the extractor 3 is withdrawn through conduit 13 and enters the top of an ion exchange column or the like in exchange means.
  • the effiuent from the column 5 is conveyed through conduit 14 and back through conduit 12 into the liquid-liquid extractor 3.
  • the aqueous solution which enters the liquid-liquid extractor 3 through conduit 12 flows in countercurrent to the organic solvent solution which enters the extractor 3 through conduit 11 and is withdrawn from the extractor 3 through the conduit 15.
  • two circuits are established, to wit, the organic solvent circuit 10, 2, 11, 3, 15 and the circuit of the aqueous system 14, 12, 3, 13 and 5, the liquid being circulated by means of the pumps 1 and 4, respectively.
  • the tobacco to be extracted is located in the solidliquid extractor 2 and the circulating organic solvent thus dissolves from the tobacco both nicotine or its salts and, other soluble tobacco constituents. After some time, however, the organic solvent is enriched with the other soluble tobacco constituents.
  • the nicotine, dissolved in the organic solvent is constantly removed therefrom by means of the aqueous solution in the liquid-liquid extractor 3, the organic solvent is capable constantly to dissolve fresh amounts of nicotine from the tobacco. It will thus be appreciated that nicotine is continuously removed from the tobacco, and in turn from the organic phase by the aqueous solution, while other soluble tobacco constituents are dissolved in the organic solvent until an equilibrium condition has been established.
  • the tobacco is removed from the extractor 2 and is dried in a drier to evaporate adhering organic solvent. It has been ascertained that the equilibrium condition in respect to the other constituents referred to, is established, if the amount of soluble tobacco constituents which is restored to the dried tobacco by the evaporation of the adhering solvent, is equal to the amount of such constituents dissolved during the extraction with the organic solvent. In this manner, the amount of the other tobacco constituents originally dissolved during the extraction but restored during the subsequent drying will remain constant in the tobacco so that in effect no loss of these desirable constituents takes place.
  • the circulating aqueous solution which flows through conduits 14 and 12 into the liquidliquid extractor and from there through conduit 13 into the ion exchange column, is essentially saturated with water-soluble tobacco constituents so that essentially no water-soluble tobacco constituents are dissolved by the Water during its contact with the organic phase.
  • the water of course, not only dissolves the nicotine contained in the organic phase, but will also be enriched with Watersoluble tobacco constituents which have been leached out from the tobacco by the organic solvent.
  • the nicotine is removed from the aqueous phase by means of ion exchange which takes place in the column 5, the aqueous system thus never reaches a state of saturation in respect to nicotine, so that constantly fresh amounts of nicotine can be removed by the water from the organic phase.
  • the aqueous phase dissolves other water-soluble tobacco constituents from the organic phase until a solubility equilibrium condition has been established. Once this equilibrium condition prevails, the amount of watersoluble tobacco constituents in the aqueous phase remains essentially constant since these constituents are not removed by the ion exchange. If desired, the concentration of these other water-soluble tobacco constituents may be limited in the aqueous phase by continuously or intermittently recycling a portion of the aqueous phase to the treated tobacco and replacing the recycled portion by fresh water. A separate recycling of the water to the tobacco is rendered unnecessary if the aqueous solution is used for the production of the customary tobacco sauces.
  • the aqueous phase is particularly suitable for this purpose since it is essentially free from nicotine and any extraneous components.
  • the inventive process is characterized by a three-fold selectivity which is not obtainable by prior art processes.
  • This three-fold selectivity is attained by the advantageous transfer of the nicotine through the three-phase boundaries: tobaccoorganic solvent, organic solvent-Water, and water-ion exchanger.
  • the pH value of the aqueous phase varies dependent on the particular kind of tobacco and the process conditions, but is always higher before the aqueous phase enters the ion exchanger than it is in the efiluent exiting from the column.
  • a further lowering of the pH value in the aqueous phase may be accomplished by adding to the aqueous phase small amounts of extraneous acids as, for example, sulphuric acid, hydrochloric acid, phosphoric acid or citric acid. Contrary to the known processes, however, it is not necessary to use stoichiometric amounts but very small quantities are sufficient, since, as stated, the ion exchanger constantly regenerates the free acids from the salts which are formed by neutralization with the nicotine.
  • Cation exchangers are advantageously used in the acid form because, as mentioned above, the natural acids of the tobacco will thus be retained in the aqueous system and thus may ultimately be restored to the tobacco.
  • organic liquids which are miscible with water to a limited extent only, are suitable for the inventive process.
  • solvents are, for example, ketones, such as butanone and cyclohexanone; various esters such as methylacetate, ethylacetate or butylacetate; ethers, such as diethylether, diisopropylether and diisobutylether; hydrocarbons such as pentane, exane, cyclohexane, benzene and toluene; further, halogenated hydrocarbons such as tetracarbonchloride, chloroform, methylenechloride, trichloroethylene, monofiuorodichloroethylene and difluorodichloroethylene; moreover, alcohols which dissolve in water with difficulty only, such as isobutanol, amylalcohol and cyclohexanol are embraced within the inventive concept.
  • Halogenated aliphatic hydrocarbons for example, methylenechloride are particularly preferred as organic solvents in the inventive process, due to their excellent extraction effect and their incombustibility.
  • solvents may be employed as additives which are miscible with water. Alcohols such as methanol, or ketones such as acetone, may thus be used as components in solvent mixtures.
  • the inventive process is particularly suitable for the extraction of nicotine from tobacco.
  • the extraction may be carried out at any processing stage of the tobacco, primarily, however, with raw tobacco, cut tobacco and tobacco from which the ribs of the leaves have been removed.
  • the moisture content of the tobacco to be extracted should be adapted to the respective process conditions and should generally have an average value. If the tobacco is very dry, undesired breakage of the tobacco structure may occur, while very moist tobacco requires additional energy for drying purposes. Therefore, both very dry and very moist tobacco may negatively affect the economics of the process. Experience has demonstrated that in most instances a tobacco moisture content of between 12 to 20% gives excellent results. It should be appreciated, however, that this range is not limiting and that tobacco of a different moisture content may also be processed in accordance with the invention.
  • Customary apparatus generally used in the tobacco industry and in chemical processing plants in general may be used for carrying out the inventive process, even if the process is performed continuously.
  • the apparatus of FIG. 2 comprises a solid-liquid extractor 20 which is supplied with solid material to be extracted, for example, tobacco from a storage container which feeds the solid material into the extractor 20 through a conveying means 6a.
  • Organic solvent is stored in a storage vessel which discharges into the extractor 20 through conduit 99 which is valve controlled by the valve 7a.
  • the solid material after extraction, is discharged from the extractor 20 into a drier 80, the material being transported from the extractor 20 into the drier by means of the conveying means 20.
  • the drier 80 may optionally be connected through conveying means 8a with a conditioning unit and the latter, in turn, may discharge into a storage container 100' through a transporting means 90.
  • the organic solvent after having passed through the extractor 20, passes through conduit 98 into the liquidliquid extractor 30 and from there back into the extractor 20 through conduit 97.
  • the organic liquid is forced through its circulatory path by means of pump 111, a flow meter 1a being connected in the conduit 98.
  • Aqueous medium is pumped by pump 4 through conduit 96 into the liquid-liquid extractor 30 where the aqueous phase flows in counter-current to the organic phase.
  • the aqueous phase exits from the liquid-liquid extractor 30 through conduit and enters the top of ion exchange column 50.
  • a valve 5a is connected in the conduit 95.
  • the aqueous efiiuent exits from the column 50 through conduit 93 and is again introduced into the liquid-liquid extractor 30 through line 96, the movement of the aqueous phase being caused by the pumping action of the pump 4.
  • Flow meter 4a is connected in the line 93.
  • the system also includes a regeneration container 13 which is connected to the exit of the column 50 through conduit 92, valves 13a and 5d being connected in the conduit in addition to the pump 13b.
  • a water container 14 is connected to the conduit 92 by line 91 which latter is valve-controlled by valve 14a.
  • the top of the water container 14 is connected to a solvent recovery unit 16 through line 89.
  • Valve 16b is connected in line 89.
  • the solvent recovery unit 16 in turn, is linked to the drier 80 through line 88 and to the solvent storage container 70 through line 87.
  • Valve 16a is connected in line 87.
  • the drier 80 is interiorly provided with a spraying means indicated by reference numeral 17, the spraying means being fed by the aqueous phase through pipe 85 which connects the spraying means 17 to conduit 96 of the aqueous circuit.
  • Valve 4b and flow meter 40 are connected in the pipe 85.
  • the system moreover, includes a regenerate collecting vessel 12, the bottom of which is communicating with a regenerate processing unit 15 through line 82, valve 12a being connected in the line 82.
  • the top of the regenerate collector 12 is connected to the top of the ion exchange column through line 79, valve b and pump 50 being connected in this line.
  • the continuously operating solid-liquid extractor 20 may be arranged horizontally or vertically.
  • the liquid-liquid extractor 3% may be constructed in different embodiments.
  • it may be a centrifugal extractor, or it may be a column filled with filling bodies.
  • any of the conventional constructions providing for continuous regeneration may be employed.
  • the solvent recovery unit 16 this may comprise a cooler, a wash tower with distillation arrangements, an absorption device or a combination of such units.
  • the drier 80 which may be a drum drier, a turbulent drier or a belt drier.
  • the casing should only be open at those areas where the tobacco is introduced and discharged.
  • the vapors which are sucked off from the casing may then be supplied to the solvent recovery system 16.
  • the conveying means 2a ' which transports the moist tobacco from the extractor 20 to the drier 80 should preferably be in the form of a screw conveyor.
  • the tobacco is first conveyed from the storage container 60 into the extractor 20-.
  • This may be accomplished, for example, by a suitable shaking device or by pneumatic transportation.
  • the transporting means for this purpose has been indicated by reference numeral 6a.
  • the solvent which is stored in the container 70 flows by gravity through line 99 into the extractor 20. If necessary, a pump may, of course, be employed for this purpose.
  • the solvent which thus is charged with nicotine flows then through line 98 into the liquid-liquid extractor 30.
  • the aqueous solution existing through line 93 from the ion exchange column 50 is pumped by pump 4 and through line 96 into the liquid-liquid extractor 30'.
  • the liquid phase thus extracts the nicotine from the organic phase in the extractor 30.
  • the pump 111 again forces the organic phase through line 98 back into the solid-liquid extractor 20 for extraction of further amounts of nicotine from the tobacco.
  • the cycle for the organic phase is thus complete.
  • the tobacco in the extractor 20 is conveyed by the conveying means 212, to wit, for example a screw conveyor, into the drier 80.
  • the drier 80 is heated and as previously set forth may be operated under vacuum condition.
  • the solvent therefore evaporates and the solvent vapors fiow through line 88 into the solvent recovery unit 16.
  • the solvent may be recovered in the unit 16, for example, by cooling, compression, washing or absorption. Recovered solvent is returned to the solvent storage Vessel 70 through valve-controlled line 87.
  • the tobacco may be conditioned within the drier 80 by spraying a portion of the aqueous phase onto the tobacco.
  • the spraying device 17 is arranged which is fed through line 85' with the aqueous phase, to wit, the efiiuent discharged from the ion exchange column 50.
  • the aqueous phase used for this purpose may be a component of a customary tobacco sauce.
  • any water which evaporates together with the solvent is separated in the solvent recovery unit 16, and after phase separation from the solvent, is collected in the water container 14.
  • line 89 is provided which connects the water container 14 to the solvent recovery unit 16.
  • the water collecting vessel 14, in turn, is connected through lines 91 and 92 with the ion exchange column 50 and supplemental water may thus be supplied from the water collecting vessel 14 to the ion exchange unit 50 in order to supply additional water to the aqueous phase, particularly if an amount of the aqueous phase has been bled off to the spraying unit 17.
  • the additional water emanating from the water storage container 14 is also used for flushing back the filling in the ion exchanger.
  • the water from the container 14 may also be conveyed into the regenerating container 13 as indicated in FIG. 2.
  • the nicotine-containing regenerate obtained in the regeneration of the ion exchange column 50 is first conveyed into the regenerate collector 12. This is accomplished through line 79 and pump 5c.
  • the processing of the regenerate takes place in the regenerate processing unit 15 which is connected with the regenerate collector 12 through line 82. Water or, after addition of alkalis, water and nicotine are evaporated in the regenerate processing unit 15.
  • the tobacco which is discharged from the drier may be conveyed through conveying means 811 into the conditioning unit where the tobacco is brought to the desired moisture content and may also be admixed with suitable additives.
  • the tobacco finally reaches, through conveying means 911, the tobacco storage unit 106 which may consist of barrels, silos, or any other suitable storage device.
  • the ion exchange column contained a cation exchanger in pearl form (particle size 0.2 to 1.0 millimeter) of the sulfonated polystyrene type.
  • the specific load on the ion exchanger was 10 liters per hour water per one liter of ion exchanger.
  • the tobacco was removed from the extractor and was dried together with 14 kilogram of 1,2 dichloroethane which adhered to the tobacco.
  • the heat drying was efiected in a closed unit, whereby the evaporating organic solvent was recovered by suitable cooling. 7.0 kilograms of tobacco having a nicotine content of 0.63% were obtained in this manner.
  • the exterior of the tobacco appeared unchanged and the burning characteristics and the smoke aroma of the tobacco were the same as before the treatment.
  • the ion exchanger was exhausted after the performance of several tests in accordance with the above description.
  • the efiiuent was tested in order to ascertain when the ion exchanger was spent. It was ascertained that the ion exchanger was capable of absorbing about 250 grams of nicotine per 1 liter of ion exchanger. Regeneration of the ion exchanger was eifected with sulphuric acid of 5% concentration and the collected eluates were subsequently concentrated unitl the nicotine concentartion amounted to 40%. The regenerated ion exchanger was then again used for further experiments.
  • Example II This example was carried out with 10.0 kilograms of Burley tobacco having a nicotine content of 4.1% and exhibiting a moisture content of 9%.
  • the extraction with the organic phase was carried out with 3000 liters per hour of circulating methylenechloride at room temperature.
  • the organic solvent was brought into extracting contact in a liquid-liquid extractor with 500 liter per hour of water.
  • the water, enriched with nicotine was circulated through an ion exchange resin column which contained an acid cation exchanger.
  • the tobacco was dried in a closed drier together with 29 kilograms of adhering methylenechloride. The drying was eifected so that the temperature of the tobacco did not rise above 55 C.
  • the tobacco was sprayed with 1.0 liter of the aqueous phase.
  • the aqueous solution was bled from the aqueous circuit of the .process directly behind the ion exchange column.
  • the tobacco, after the spraying, was further dried to evaporate the water and residual solvent.
  • the methylenechloride which exited from the drier in vapor form was condensed by cooling and uncondensible vapors were absorbed on active carbon.
  • the tobacco was again moistened by further spraying of a small amount of the aqueous phase to impart the tobacco with its original moisture content of 9%.
  • the yield of tobacco amounted to 9.5 kilogram and the nicotine content of the treated tobacco was 0.45%.
  • Example 111 This experiment was carried out with Burley tobacco which was extracted with 1,1,1 trichloroethane. The extraction was effected in a continuous solid-liquid extractor operating on the screw conveyor principle and 100 kilograms of the Burley. were fed through the screw conveyor per hour with 25,000 liter per hour of the 1,1,1 trichloroethane flowing in counter current to the tobacco. The 1,1,1 trichloroethane exiting from the extractor was contacted with 3000 liter per hour of water in a liquid-liquid extractor and was thereafter again recycled to the tobacco. The nicotine-containing water was circulated through an ion exchange column.
  • a cation exchanger of the sulfonated organic coal or carbon type having a particle size of 20 to 50 mesh and a capacity of about 80 grams of nicotine per liter.
  • the temperatures of the organic and the aqueous phases were between 20 and 25 C. and the total extraction time amounted to 90 minutes.
  • the regeneration of the ion exchanger was effected after ten tests of the indicated kind with sulphuric acid of 8% concentration.
  • a nicotine sulphate solution of 40% concentration, calculated on the nicotine base was recovered.
  • Example IV 1.0 kilogram of dried hips are extracted with cyclohexanol at room temperature in a solid-liquid extractor.
  • the organic solvent exiting from the extractor is conveyed into a Raschig column where the organic phase is continuously brought in contact with water flowing in counter current.
  • the organic phase is then again recycled to the hip-containing solid-liquid extractor for further extraction purposes.
  • the aqueous phase is conveyed from the Raschig column to an ion exchange column containing 1 liter of anion exchanger of the aliphatic aminephenol-formaldehyde condensate-type where ascorbic acid contained in the aqueous phase is removed.
  • the efiluent is recycled to the Raschig column.
  • the procedure is briefly interrupted after a treatment time of 5 hours in order to exchange the extracted hips for a fresh amount, whereafter the process is continued.
  • the anion exchanger is regenerated with sodium hydroxide solution of 2% concentration and 12.3 grams of ascorbic acid are recovered from the discharged regenerate according to known methods.
  • the inventive procedure is not restricted to the selective extraction of basic constituents from plant material, such as of nicotine from tobacco, but by suitably adapting the procedure it may equally successfully be used for the selective extraction of acidic plant constituents such as ascorbic acid from fruits and leaves. All that is required for extracting acid constituents is the use of an anion exchanger and, if necessary, the aqueous phase can be adjusted to a pH above 7 by the addition of suitable bases.
  • the process is not limited to the removal of nicotine from tobacco but other alkaloids may, of course, be obtained in the inventive manner.
  • the process is suit able for extracting quinine from China bark, morphine from opium or atropine from dried leaves of atropine belladonna.
  • a process of selectively removing a particular waterand organic solvent-soluble substance of acid and/or basic reaction from solid plant particles containing a plurality of Waterand organic solvent-soluble substances which comprises:
  • a cyclic process of removing nicotine from tobacco which comprises:

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Compounds Of Unknown Constitution (AREA)
US533023A 1965-03-11 1966-03-09 Process for extracting substances from plant particles Expired - Lifetime US3390685A (en)

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DEE28880A DE1298078B (de) 1965-03-11 1965-03-11 Verfahren zur selektiven Extraktion basischer bzw. saurer Pflanzen-inhaltsstoffe, insbesondere zum Entnikotinisieren von Tabak

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JP (1) JPS5025040B1 (index.php)
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Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3561451A (en) * 1967-05-17 1971-02-09 American Mach & Foundry Process of manufacturing reconstituted tobacco of light color
US3612066A (en) * 1970-02-05 1971-10-12 Reynolds Tobacco Co R Denicotinizing process
US3717155A (en) * 1970-05-18 1973-02-20 Amf Corp Reconstituted tobacco product
US3880172A (en) * 1972-03-16 1975-04-29 Ici Ltd Smoking mixtures
US4131118A (en) * 1976-11-12 1978-12-26 Philip Morris Incorporated Method for removal of potassium nitrate from tobacco extracts
US4144895A (en) * 1974-03-08 1979-03-20 Amf Incorporated Solvent extraction process
US4215706A (en) * 1978-10-13 1980-08-05 Loew's Theatres, Inc. Nicotine transfer process
US4267847A (en) * 1978-05-12 1981-05-19 British-American Tobacco Company Limited Tobacco additives
US4506682A (en) * 1981-12-07 1985-03-26 Mueller Adam Clear tobacco aroma oil, a process for obtaining it from a tobacco extract, and its use
US4967771A (en) * 1988-12-07 1990-11-06 R. J. Reynolds Tobacco Company Process for extracting tobacco
US5005593A (en) * 1988-01-27 1991-04-09 R. J. Reynolds Tobacco Company Process for providing tobacco extracts
US5018540A (en) * 1986-12-29 1991-05-28 Philip Morris Incorporated Process for removal of basic materials
US5025812A (en) * 1989-08-10 1991-06-25 R. J. Reynolds Tobacco Company Tobacco processing
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
US5148819A (en) * 1991-08-15 1992-09-22 R. J. Reynolds Tobacco Company Process for extracting tobacco
US5234008A (en) * 1990-02-23 1993-08-10 R. J. Reynolds Tobacco Company Tobacco processing
US5497792A (en) * 1987-11-19 1996-03-12 Philip Morris Incorporated Process and apparatus for the semicontinuous extraction of nicotine from tobacco
EP1176143A1 (en) * 2000-07-27 2002-01-30 Rohm And Haas Company Anhydrous purification of nicotine using an ion exchange resin
WO2003061804A1 (en) * 2002-01-18 2003-07-31 Advanced Phytonics Limited Purification of impure materials using non-aqueous solvents
GB2385289A (en) * 2002-01-18 2003-08-20 Advanced Phytonics Ltd Purifying a material using a non-aqueous solvent and an ion exchange resin or adsorbent.
US20040112394A1 (en) * 2002-07-18 2004-06-17 Val Krukonis Reduction of constituents in tobacco
CN111671137A (zh) * 2020-05-14 2020-09-18 湖北中烟工业有限责任公司 玫瑰花提取物香料、制备方法及加热不燃烧卷烟

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180103680A1 (en) * 2016-10-18 2018-04-19 Altria Client Services Llc Methods and systems for improving stability of the pre-vapor formulation of an e-vaping device

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US802487A (en) * 1903-12-28 1905-10-24 Karl Wimmer Treatment of tobacco for the removal of nicotin.
US1949012A (en) * 1931-03-27 1934-02-27 Generaldirektion Der Osterreic Method of preparing tobacco free from nicotine
US3046997A (en) * 1960-09-27 1962-07-31 Philip Morris Inc Selective alkaloid extraction

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2293954A (en) * 1938-06-21 1942-08-25 Permutit Co Recovery of nicotine
US2805667A (en) * 1953-09-17 1957-09-10 Martin Brinkmann K G Process for treating tobacco

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US802487A (en) * 1903-12-28 1905-10-24 Karl Wimmer Treatment of tobacco for the removal of nicotin.
US1949012A (en) * 1931-03-27 1934-02-27 Generaldirektion Der Osterreic Method of preparing tobacco free from nicotine
US3046997A (en) * 1960-09-27 1962-07-31 Philip Morris Inc Selective alkaloid extraction

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3561451A (en) * 1967-05-17 1971-02-09 American Mach & Foundry Process of manufacturing reconstituted tobacco of light color
US3612066A (en) * 1970-02-05 1971-10-12 Reynolds Tobacco Co R Denicotinizing process
US3717155A (en) * 1970-05-18 1973-02-20 Amf Corp Reconstituted tobacco product
US3880172A (en) * 1972-03-16 1975-04-29 Ici Ltd Smoking mixtures
US4144895A (en) * 1974-03-08 1979-03-20 Amf Incorporated Solvent extraction process
US4131118A (en) * 1976-11-12 1978-12-26 Philip Morris Incorporated Method for removal of potassium nitrate from tobacco extracts
US4267847A (en) * 1978-05-12 1981-05-19 British-American Tobacco Company Limited Tobacco additives
US4215706A (en) * 1978-10-13 1980-08-05 Loew's Theatres, Inc. Nicotine transfer process
US4506682A (en) * 1981-12-07 1985-03-26 Mueller Adam Clear tobacco aroma oil, a process for obtaining it from a tobacco extract, and its use
US5018540A (en) * 1986-12-29 1991-05-28 Philip Morris Incorporated Process for removal of basic materials
US5497792A (en) * 1987-11-19 1996-03-12 Philip Morris Incorporated Process and apparatus for the semicontinuous extraction of nicotine from tobacco
US5005593A (en) * 1988-01-27 1991-04-09 R. J. Reynolds Tobacco Company Process for providing tobacco extracts
US4967771A (en) * 1988-12-07 1990-11-06 R. J. Reynolds Tobacco Company Process for extracting tobacco
US5025812A (en) * 1989-08-10 1991-06-25 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
US5065775A (en) * 1990-02-23 1991-11-19 R. J. Reynolds Tobacco Company Tobacco processing
US5148819A (en) * 1991-08-15 1992-09-22 R. J. Reynolds Tobacco Company Process for extracting tobacco
KR100821911B1 (ko) * 2000-07-27 2008-04-16 롬 앤드 하스 캄파니 이온 교환 수지를 이용한 니코틴의 무수정제
EP1176143A1 (en) * 2000-07-27 2002-01-30 Rohm And Haas Company Anhydrous purification of nicotine using an ion exchange resin
WO2003061804A1 (en) * 2002-01-18 2003-07-31 Advanced Phytonics Limited Purification of impure materials using non-aqueous solvents
GB2385289A (en) * 2002-01-18 2003-08-20 Advanced Phytonics Ltd Purifying a material using a non-aqueous solvent and an ion exchange resin or adsorbent.
US20060084812A1 (en) * 2002-01-18 2006-04-20 Bellamy Simon A Purification of impure materials using non-aqueous solvents
US20040112394A1 (en) * 2002-07-18 2004-06-17 Val Krukonis Reduction of constituents in tobacco
US7798151B2 (en) 2002-07-18 2010-09-21 Us Smokeless Tobacco Co. Reduction of constituents in tobacco
US20110067715A1 (en) * 2002-07-18 2011-03-24 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
US10045557B2 (en) 2002-07-18 2018-08-14 Us Smokeless Tobacco Co. Reduction of constituents in tobacco
CN111671137A (zh) * 2020-05-14 2020-09-18 湖北中烟工业有限责任公司 玫瑰花提取物香料、制备方法及加热不燃烧卷烟

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JPS5025040B1 (index.php) 1975-08-20
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DE1298078B (de) 1969-06-26
GB1080639A (en) 1967-08-23

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