US3139435A - Process for selective extraction of alkaloid - Google Patents

Process for selective extraction of alkaloid Download PDF

Info

Publication number
US3139435A
US3139435A US263637A US26363763A US3139435A US 3139435 A US3139435 A US 3139435A US 263637 A US263637 A US 263637A US 26363763 A US26363763 A US 26363763A US 3139435 A US3139435 A US 3139435A
Authority
US
United States
Prior art keywords
alkaloid
solvent
brine
tobacco
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.)
Expired - Lifetime
Application number
US263637A
Other languages
English (en)
Inventor
Staley John
Clarke Allan Bellerby
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.)
Philip Morris USA Inc
Original Assignee
Philip Morris USA Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Philip Morris USA Inc filed Critical Philip Morris USA Inc
Priority to US263637A priority Critical patent/US3139435A/en
Priority to FR966383A priority patent/FR1393621A/fr
Priority to BR157372/64A priority patent/BR6457372D0/pt
Priority to DK113764AA priority patent/DK109041C/da
Priority to CH292964A priority patent/CH437331A/de
Priority to GB9677/64A priority patent/GB1024284A/en
Application granted granted Critical
Publication of US3139435A publication Critical patent/US3139435A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/81—Solanaceae (Potato family), e.g. tobacco, nightshade, tomato, belladonna, capsicum or jimsonweed
    • 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
    • A24B15/26—Use of organic solvents for extraction

Definitions

  • This invention relates to extraction of nicotine and other alkaloid fractions from tobacco. More particularly it relates to extraction of such fractions without materially affecting the non-alkaloid constituents of the tobacco and accordingly provides tobacco which is substantially unaffected in composition, save for the removal of nicotine and other alkaloids therefrom.
  • the invention also provides substantially pure nicotine and other alkaloid fractions essentially free from contamination by fats, waxes, sugars and other related tobacco constituents.
  • Nicotine and other alkaloids occur in tobacco in both the free and combined states and are readily extractable in common organic solvents, as are a number of other tobacco constituents. It is to be understood that references in this specification to nicotine and alkaloids include nicotine and alkaloids in their salt form.
  • Solvent extraction of tobacco to remove nicotine has long been practiced. Such methods have been characterized, however, by a number of attendant disadvantages, principally that solvent-soluble tobacco constituents other than nicotine are removed thereby, yielding nicotine in admixture with substantial amounts of undesirable impurities and providing tobacco of markedly inferior character as a result of the removal of desirable tobacco con stituents.
  • a particular advantage of the present invention in one aspect is the provision of a markedly simpler and less expensive means for removing nicotine from the brine following contact with the alkaloid-laden solvent. Nicotine is removed from the brine to permit recycling of the brine and its repeated use to remove nicotine from alkaloidladen solvent. The nicotine so recovered is, in addition, a valuable item of commerce.
  • Our method of nicotine removal is based on the discovery that a phase relationship develops between nicotime and salt brine as a function of temperature.
  • the lower operative limit of temperature is that at which freezing or separation of contained solids occurs.
  • the economic cost of refrigeration may constitute a limiting factor on the temperature which is employed; a suitable low temperature may readily be selected by one skilled in the art in accordance with the teachings herein contained.
  • Efiiciency of alkaloid transfer from the solvent to the brine also improves markedly as the pH is lowered.
  • FIG. 1 there is shown the equilibrium relationship between nicotine concentration in a methyl ethyl ketone (MEK) saturated aqueous NaCl brine system at 25 C., and it will be observed that reduction of pH markedly increases efficiency of transfer of alkaloid from solvent to brine.
  • MEK methyl ethyl ketone
  • pH 7 roughly equal concentrations of alkaloid are found in the solvent and the brine at equilibrium; acidification to pH increases substantially the proportion of alkaloid in the brine. Below pH 5, and particularly below pH 4, virtually all the alkaloid is transferred to the brine.
  • the pH of the alkaloid-laden solvent which is desirably nearly neutral following extraction of tobacco, is reduced and the solvent is chilled to a tern erature substantially below room temperature before contacting the solvent with the brine.
  • the alkaloid-laden brine emerges from the extraction column at a low temperature and an acid pH after contact with the solvent.
  • An effluent brine pH of about 4.5 and a temperature of about 10 C. are illustrative of the operating conditions in one embodiment of this invention.
  • refrigeration means may be provided in the vessel or column in which the solvent and brine are contacted. The important feature is the lower temperature of the brine-solvent system; the manner of obtaining such lower temperature is largely a matter of choice.
  • the invention in this aspect accordingly provides an improvement in a continuous process of tobacco extraction and alkaloid recovery and includes the steps of contacting the alkaloid-laden solvent with brine at a temperature substantially below that at which alkaloid is ultimately recovered from the brine and at a pH below about 6.5.
  • the resultant alkaloid-enriched brine is thereafter warmed to a temperature at which an alkaloid phase separates from the brine and the alkaloid phase is physically removed from the brine, as by decantation.
  • the alkaloid-relieved brine i.e., warmed brine from which the alkaloid phase has been separated contains only a minor amount of alkaloid; although saturated, the alkaloid concentration is very low, e.g., less than 1 mg./ml. of brine.
  • the capacity of the alkaloid-relieved brine for alkaloid increases. At this lower temperature (below that at which alkaloid is ultimately recovered from the brine) the increased capacity of brine for alkaloid permits transfer of alkaloid from solvent to brine.
  • the acidic pH of the solvent (which is preferably lower than the pH of the entering brine) causes a decrease in brine pH, and the acidic environment enhances transfer of alkaloid from solvent to brine.
  • An acidic environment may, of course, be provided by acidifying the brine rather than the solvent, or acidification may be accomplished by adding acid or acidic material directly to the vessel or column in which the solvent and brine are contacted.
  • the particular means of providing an acidic environment are not of especial importance.
  • the pH of the alkaloid-enriched brine to a nearly neutral level, suitably 5.5-8, prior to decanting the alkaloid, but the step of neutralizing the brine is optional and may in addition take place either before or after the cold alkaloid-enriched brine is warmed. Somewhat greater amounts of alkaloid are recovered from the brine at a higher pH.
  • FIG. 2 is a graph setting forth the relationship between the moisture content of the system and the amount of nicotine extracted.
  • the graph is based upon equilibrium data obtained by extracting 25 g. bright leaf tobacco found by analysis to contain 1.48% of alkaloid with 1250 ml. MEK.
  • efiiciency of nicotine extraction increases with increasing moisture content in the system up to a point, and then drops off rapidly to a significantly lower level.
  • the moisture content of the extracting solvent is influenced by the moisture content of the tobacco being extracted, and also by the concentration and composition of the brine. Adjustment of solvent moisture level is most conveniently effected by addition of water or anhydrous solvent to the extraction solvent. While, as shown in FIG. 2, optimum moisture content may be expressed in terms of mg. H O per m1. of solvent, the numerical value of this measure for various solvents can be quite different.
  • the moisture content of the tobacco, with which the solvent is in equilibrium is about the same for optimum moisture contents of a wide variety of solvents.
  • a solvent moisture content corresponding to at least about 10% moisture in the tobacco being extracted.
  • Levels below about 10% are preferably to be avoided due to low extraction efiiciency, while levels above about 25% are preferably to be avoided because of less than optimum efiiciency and because bleeding (i.e., loss of water-soluble tobacco con stituents) or other injury to the tobacco becomes objectionable at moisture levels significantly above 25%.
  • FIG. 3 there is shown the equilibrium relationship between moisture in tobacco and moisture in extracting solvent at 23 C. (data obtained with 1250 ml. MEK and 25 g. bright leaf tobacco).
  • a tobacco moisture content between about 10%-25% provides a solvent moisture content in the optimum range for extraction of nicotine.
  • FIG. 4 is a schematic flow sheet showing an arrangement of apparatus suitable for practicing the invention. It is to be understood that various changes may be made in the system illustrated and that the flow sheet is not to be taken in a limiting sense.
  • receptacles 1 which may be hogsheads, to contain tobacco from which alkaloid is to be extracted.
  • these are equipped with warming means, such as steam heated coils within the containers.
  • steam admitting means 2 and condensate returning means 3 there is illustratively shown steam admitting means 2 and condensate returning means 3, and there may also be provided means such as a temperature sensing device 4 located in an efiluent solvent line in operative connection with an automatic valve 5 located in the steam admitting line to afford regulation of temperature by controlling the amount of steam admitted responsively to the temperature of effiuent solvent.
  • a tobacco density as great as about 15-20 lbs./ cu. ft.
  • Alkaloid-relieved solvent which is saturated with nonalkaloid solvent-soluble tobacco fractions from previous extraction of the same or other tobacco is drawn from solvent storage tank 6 and pumped to receptacles 1.
  • fresh or make-up solvent may be employed, i.e., solvent which has not previously been employed for extraction, in which event it will become saturated with solvent-soluble tobacco fractions as it passes through the successive receptacles 1 of tobacco.
  • Pump means such as that indicated illustratively at 28 between receptacles D and E may be included in the system as desired.
  • the solvent may pass through the tobacco containers serially, but provision may be made for feeding solvent from tank 6 directly to more than one of the tobacco containers, and provision may also be made for cycling solvent from one or more tobacco containers directly to the subsequent process operations without passing such solvent through additional batches of tobacco.
  • the latter arrangement is particularly useful when employing a solvent which has not previously been used for extraction of tobacco and which accordingly is not saturated with non-alkaloid tobacco fractions.
  • a fresh hogshead of tobacco will replace the receptacle designated A in FIG. 4, displacing the receptacle of longest residence in the system (F in FIG. 4), which may then be processed for recovery of residual solvent (not shown).
  • the solvent drawn from the storage tank may have a nearly neutral pH, suitably about 6.5.
  • a tank 7 of alkali such as KOH or other acid-neutralizing material, may be provided, communicating through appropriate valve means with a line of solvent which is to be used for further extraction.
  • pH sensing means 8 located in a solvent efliuent line downstream from and in operative connection with automatic valve 9 to admit controlled amounts of alkali to the stream of solvent for maintaining pH at a desired level or within a desired range.
  • the moisture content of the extracting solvent may, as heretofore described, be ascertained by measurement of the moisture content of the tobacco being extracted. Adjustment of solvent moisture may be accomplished by addition of controlled amounts of water from tank 26 or of anhydrous solvent from tank 25, as may be appropriate; less conveniently, adjustment may be etfectuated by altering the concentration or composition of the brine.
  • Alkaloid-laden solvent passes from the extraction zone through a heat exchanger 10, which it leaves at a temperature lower than that at which it entered.
  • the warm solvent may enter the heat exchanger at about 70 C. and leave at about 45 C.
  • the pH of the solvent stream is then decreased by addition of acid such as HCl.
  • pH sensing means 13 downstream from the point of addition may be employed to control the admission of acid through valve 12, with which such sensing means is in operative connection.
  • a pH below about 6.5 is preferred, and a pH of about 4 or below is more preferred.
  • the solvent is then passed through a chilling unit 14, cooled by refrigeration unit 15. Acidification may take place after chilling, but in such event allowance should be made for increase in temperature upon addition of acid. In any event care should be taken to avoid separation of any part of the solvent solution by reason of too low a temperature.
  • An efiiuent temperature of 5-10 C. is suitable.
  • the chilled and acidified alkaloid-laden solvent then passes through a liquid-liquid extraction column 16 against brine, preferably in countercurrent flow.
  • Suitable brines are set forth in the Hind patent.
  • Efl luent solvent from the extraction column is cycled to the heat exchanger, whence it may have a temperature of about 35 C. and a pH of about 4.0.
  • the pH of the solvent may be adjusted to the level desired for extraction, as by addition of alkali from tank 7.
  • pH sensing means 23 and automatic valve 24 may be em- 6 ployed for adjustment in a manner such as that previously described.
  • Effiuent alkaloid-laden brine from column 16 comprising water, salt, alkaloid and perhaps a minor amount of non-alkaloid tobacco solubles, all as a single phase, is then passed through heat exchanger 17 and warmed at least to a temperature at which the nicotine fraction of the brine separates into a distinct and separate phase.
  • a greater amount of nicotine will separate as the temperature is increased, but no particular advantage is obtained by increasing the temperature much above the ambient, i.e., about 25 C.
  • the pH of the warmed brine is then increased to a nearly neutral level, suitably about 6.5, a tank 19 of alkali and pH sensing means 18 in operative connection with automatic valve 20 being desirable. Adjustment of pH may precede the warming step, if desired.
  • the nicotine floating atop the brine is then tapped off in decanter 21 and collected in pool 22. Alkaloid-relieved brine is recycled to column 16.
  • a continuous process for selective removal and recovery of alkaloid from tobacco which includes the steps of extraction of tobacco with organic solvent, contacting the resultant alkaloid-laden solvent extract with brine to remove alkaloid selectively from said extract, recycling the alkaloid-relieved solvent to tobacco, recovering alkaloid from the brine and recycling the alkaloidrelieved brine for contacting with further alkaloid-laden solvent, the improvement which comprises contacting the alkaloid-laden solvent with the brine at a temperature substantially below that at which alkaloid ultimately is recovered from the brine and at a pH below about 6.5, thereafter warming the resultant alkaloid-enriched brine to a temperature at which an alkaloid phase separates from the brine, and effecting physical removal of the alkaloid phase from the brine.
  • a process according to claim 2 wherein the pH at which the solvent and brine are contacted is below about 4.0.

Landscapes

  • Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medical Informatics (AREA)
  • Epidemiology (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Medicines Containing Plant Substances (AREA)
US263637A 1963-03-07 1963-03-07 Process for selective extraction of alkaloid Expired - Lifetime US3139435A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US263637A US3139435A (en) 1963-03-07 1963-03-07 Process for selective extraction of alkaloid
FR966383A FR1393621A (fr) 1963-03-07 1964-03-06 Procédé d'extraction sélective des alcaloïdes du tabac
BR157372/64A BR6457372D0 (pt) 1963-03-07 1964-03-06 Processo para a extracao seletiva de alcaloides
DK113764AA DK109041C (da) 1963-03-07 1964-03-06 Fremgangsmåde til kontinuert, selektiv fjernelse og udvinding af alkaloider fra tobak.
CH292964A CH437331A (de) 1963-03-07 1964-03-06 Verfahren zur selektiven Extraktion von Alkaloiden
GB9677/64A GB1024284A (en) 1963-03-07 1964-03-06 Process for the treatment of tobacco

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US263637A US3139435A (en) 1963-03-07 1963-03-07 Process for selective extraction of alkaloid

Publications (1)

Publication Number Publication Date
US3139435A true US3139435A (en) 1964-06-30

Family

ID=23002612

Family Applications (1)

Application Number Title Priority Date Filing Date
US263637A Expired - Lifetime US3139435A (en) 1963-03-07 1963-03-07 Process for selective extraction of alkaloid

Country Status (5)

Country Link
US (1) US3139435A (de)
BR (1) BR6457372D0 (de)
CH (1) CH437331A (de)
DK (1) DK109041C (de)
GB (1) GB1024284A (de)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3396735A (en) * 1965-04-15 1968-08-13 Eresta Warenhandelsgmbh Continuous process of removing nicotine from tobacco
US3821960A (en) * 1968-05-13 1974-07-02 Tamag Basel Ag Tobacco denicotinization process
US4215706A (en) * 1978-10-13 1980-08-05 Loew's Theatres, Inc. Nicotine transfer process
US4301817A (en) * 1980-03-05 1981-11-24 Philip Morris Incorporated Method for selective denitration of tobacco
US4364401A (en) * 1980-03-05 1982-12-21 Philip Morris Incorporated Method for selective denitration of tobacco
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
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
CN114940672A (zh) * 2022-05-27 2022-08-26 云南中烟工业有限责任公司 一种烟草生物碱组分的制备方法

Citations (5)

* 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.
US1196184A (en) * 1916-08-29 Sttjart
US1577768A (en) * 1922-06-07 1926-03-23 Homer W Smith Tobacco denicotinization
US2525785A (en) * 1949-12-05 1950-10-17 Feinstein Louis Process for extracting alkaloidals from plants with aqueous ammoniaethylene dichloride mixture
US3046997A (en) * 1960-09-27 1962-07-31 Philip Morris Inc Selective alkaloid extraction

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1196184A (en) * 1916-08-29 Sttjart
US802487A (en) * 1903-12-28 1905-10-24 Karl Wimmer Treatment of tobacco for the removal of nicotin.
US1577768A (en) * 1922-06-07 1926-03-23 Homer W Smith Tobacco denicotinization
US2525785A (en) * 1949-12-05 1950-10-17 Feinstein Louis Process for extracting alkaloidals from plants with aqueous ammoniaethylene dichloride mixture
US3046997A (en) * 1960-09-27 1962-07-31 Philip Morris Inc Selective alkaloid extraction

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3396735A (en) * 1965-04-15 1968-08-13 Eresta Warenhandelsgmbh Continuous process of removing nicotine from tobacco
US3821960A (en) * 1968-05-13 1974-07-02 Tamag Basel Ag Tobacco denicotinization process
US4215706A (en) * 1978-10-13 1980-08-05 Loew's Theatres, Inc. Nicotine transfer process
US4301817A (en) * 1980-03-05 1981-11-24 Philip Morris Incorporated Method for selective denitration of tobacco
US4364401A (en) * 1980-03-05 1982-12-21 Philip Morris Incorporated Method for selective denitration of tobacco
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
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
CN114940672A (zh) * 2022-05-27 2022-08-26 云南中烟工业有限责任公司 一种烟草生物碱组分的制备方法
CN114940672B (zh) * 2022-05-27 2023-11-17 云南中烟工业有限责任公司 一种烟草生物碱组分的制备方法

Also Published As

Publication number Publication date
GB1024284A (en) 1966-03-30
CH437331A (de) 1967-06-15
DK109041C (da) 1968-03-11
BR6457372D0 (pt) 1973-02-01

Similar Documents

Publication Publication Date Title
US3139435A (en) Process for selective extraction of alkaloid
JP3155003B2 (ja) ホップエキスの製造法および該方法により得られるホップエキス
US3806619A (en) Process for recovering caffeine
US3879569A (en) Process for the decaffeination of raw coffee
US4400398A (en) Method for obtaining aromatics and dyestuffs from bell peppers
US3046997A (en) Selective alkaloid extraction
US1802533A (en) Extraction of oils
US4341804A (en) Decaffeination of aqueous roasted coffee extract
US4298736A (en) Carbon-caffeine separation
JPS5927352B2 (ja) カフエインの抽出法
US4322445A (en) Process for decaffeinating coffee
US4640841A (en) Process for the extraction of hop substances
JPS6188853A (ja) 香味成分の抽出方法
US2333756A (en) Process for the recovery of lower aliphatic acids from aqueous solutions
GB2289055A (en) Extraction of hops
US3720518A (en) Process for the manufacture of a concentrated coffee product
US4088794A (en) Process for producing coffee extract
US2377975A (en) Method of solvent extraction of oil from seeds
DE2521318C2 (de)
EP0076620B2 (de) Verfahren zur Zurückgewinnung von Koffein aus aktiver Kohle
EP0061877A2 (de) Verfahren und Anlage zur Gewinnung eines Hopfenextrakts
US2335206A (en) Coffee extract
JP2540038B2 (ja) パラフインの抽出法
US3069443A (en) Method of treating soybean oil
US4659577A (en) Method for the decaffeination of roasted coffee extracts