US3372701A - Tobacco - Google Patents

Tobacco Download PDF

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Publication number
US3372701A
US3372701A US476710A US47671065A US3372701A US 3372701 A US3372701 A US 3372701A US 476710 A US476710 A US 476710A US 47671065 A US47671065 A US 47671065A US 3372701 A US3372701 A US 3372701A
Authority
US
United States
Prior art keywords
tobacco
product
acid
flavor
lactone
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
US476710A
Other languages
English (en)
Inventor
Jr Claude E Teague
Joseph N Schumacher
Wilmer A Rohde
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.)
RJ Reynolds Tobacco Co
Original Assignee
RJ Reynolds Tobacco Co
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 RJ Reynolds Tobacco Co filed Critical RJ Reynolds Tobacco Co
Priority to US476710A priority Critical patent/US3372701A/en
Priority to US476672A priority patent/US3372699A/en
Priority to US476709A priority patent/US3372700A/en
Priority to GB32034/66A priority patent/GB1131183A/en
Priority to FR71206A priority patent/FR1487939A/fr
Priority to BE684814A priority patent/BE684814A/xx
Priority to DE19661692940 priority patent/DE1692940A1/de
Priority to NL6610871A priority patent/NL6610871A/xx
Priority to CH1112266A priority patent/CH492409A/de
Application granted granted Critical
Publication of US3372701A publication Critical patent/US3372701A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
    • A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
    • A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
    • A24B15/406—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms in a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
    • C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms

Definitions

  • This invention relates to a tobacco product and has for an object the provision of a composition and process for improving the flavor and aroma of tobacco and tobaceo smoke.
  • a further object of this invention is the provision of a process for enhancing or otherwise improving the fiavor, aroma and other qualities of certain domestic, oriental, reconstituted or synthetic tobaccos which may be deficient in said flavor or aroma or other qualities.
  • An additional object of this invention is to provide a process of preparing a smoking tobacco or product which when smoked has an enhanced flavor or aroma.
  • An additional object of this invention is to provide a process of preparing a smoking tobacco or product which when smoked has an enhanced flavor or aroma.
  • a still further object of this invention is the provision of smoking products, such as cigarettes, cigars or pipe tobacco, and a process for forming same whereby the flavor and aroma before and during smoking are improved or enhanced.
  • a tobacco product is provided to which has been added or which has been treated with a small amount of a compound selected from the group of compounds having the general formula:
  • R is a straightchain alkyl group of from 1 to carbon atoms.
  • EXAMPLE IV 4-hydroxydecanoic acid, 'y-lactone
  • a mixture of 56.1 grams (0.5 mole) of n-octene-l and 167 grams (1.0 mole) of ethyl bromoacetate was heated to A solution of 12.1 grams (0.05 mole) of benzoyl peroxide in 167 grams (1.0 mole) of ethyl bromoacetate was added d-ropwise, with stirring, during 5.5 hours, holding the temperature of the reaction mixture at 90. The mixture was stirred at 90 for an additional 2 hours and allowed to stand overnight. The dark mixture was then distilled at 20 millimeters, giving about 300 milliliters of ethyl bromoacet'ate, boiling point 5961.
  • EXAMPLE VI 4-hydr0wtetradecan0ic acid, 'y-lactone
  • a 14.5 gram sample of 4ketomyristic acid in 100 milliliters of dry, thiophene-free benzene with 0.2 gram of Adams catalyst was reduced catalytically at 220 under 1200-1350 p.s.i. hydrogen in a rocking pressure vessel for 14 hours.
  • the resulting solution was filtered free of catalyst, and the filtrate was pulled down at the water pump until free of benzene.
  • the residual oil was partitioned, using ethyl ether versus aqueous sodium carbonate (200 milliliter layers of each) in a normal 3 (funnel series.
  • the tobacco additives of the invention when incorporated into tobacco products impart a flavor and aroma both before and during smoking which many smokers consider to be desirable in smoking products.
  • the methods for defining or characterizing the quality of a flavor or aroma in the tobacco art are almost purely subjective and different smokers may define the same flavor quite differently.
  • the compounds included within the broad scope of this invention may impart different flavors or aromas depending upon the alkyl substituents therein.
  • the compounds comprehended by this invention by subjective tests, impart characteristic flavors which are desirable in tobacco products and the smoke therefrom even though the exact character thereof cannot be described on the basis of known standards.
  • the tobacco additive of Example I imparts an aroma or flavor which is reminiscent of burley tobacco which many smokers consider to be desirable in a tobacco product.
  • the aroma or flavor of the other additives may vary with variation in the length of the straight-chain alkyl substituents.
  • the additive 4-hydroxytetradecanoic acid, 'y-lactone imparts an aroma reminiscent of peaches.
  • a compound embraced by generic Formula I or mixtures thereof is added to tobacco or applied to a smoking article or its component parts in amounts of about 0.0001 to 2.0 percent by weight of the product.
  • the amount of additive is between about 0.01 and 0.5 percent by weight in order to provide a tobacco product having a desired flavor and aroma.
  • the additive may be incorporated at any step in the treatment of the tobacco but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes.
  • the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.
  • an aged, flue-cured and shredded tobacco is sprayed with a 1% ethyl alcohol solution of 4-hydroxyoctanoic acid, -lactone in an amount to provide a tobacco containing 0.025 percent by weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. It has been found that the cigarette when prepared as indicated has a desired and pleasing flavor, an aroma which to some people is reminiscent of coconut and is detectable and pleasing in the main and side smoke streams when the cigarette is smoked.
  • the additives falling within the scope of this invention may be applied to the tobacco by spraying, dipping or otherwise, utilizing suitable suspensions or solutions of the additive.
  • water or volatile organic solvents such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additive while it is being applied to the tobacco.
  • other flavorand aroma-producing additives such as those disclosed in United States Patents Nos. 2,766,145, 2,905,575, 2,905,576, 2,978,365 and 3,041,211 may be incorporated into the tobacco with the additive of this invention.
  • While this invention is principally useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars or other tobacco products.
  • the compounds may be added to certain tobacco substitutes of natural or synthetic origin and by the term tobacco as used throughout this specification is meant any composition intended for human consumption by smoking or otherwise, whether composed of tobacco plant parts or substitute materials or both.
  • the invention has been particularly described with reference to the addition of the compounds directly to tobacco.
  • the compound may be applied to the paper of the cigarette or to the wrapper of a cigar. Also it may be incorporated into the filter tip, the packaging material or the seam paste employed for gluing the cigarette paper.
  • a tobacco product is provided which includes the specified additives and tobacco although in every instance the compound need not be admixed with the tobacco as above specifically described.
  • -R is a straight-chain alkyl group of from 1 to carbon atoms.
  • a tobacco product having added thereto and dis persed therein a small amount suflicient to improve the flavor thereof of 4hydroxypentanoic acid, 'y-lactone.
  • a tobacco product having added thereto and dispersed therein a small amount sufiicient to improve the flavor thereof of 4-hydroxyhexanoic acid, 'y-lactone.
  • a tobacco product having added thereto and dispersed therein a small amount sufiicient to improve the flavor thereof of 4-hydroxyheptanoic acid, 'y-lactone.
  • a tobacco product having added thereto and dispersed therein a small amount sufiicient to improve the flavor thereof of 4-hydroxyoctan oic acid, 'ylactone.
  • a tobacco product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of 4-hydroxynonanoic acid, -lactone.
  • a tobacco product having added thereto and dispersed therein a small amount suifi-cient to improve the flavor thereof of 4-hydroxyunde canoic acid, v-lactone.
  • a tobacco product having added thereto and dispersed therein a small amount sufiicient to improve the flavor thereof of 4-hydroxydodecanoic acid, lactone.
  • a tobacco product having added thereto and dis persed therein a small amount sufiicient to improve the flavor thereof of 4-hydroxytetradecanoic acid, 'y-lactone.
  • a process for improving the flavor of a tobacco product which comprises adding thereto a small amount of a compound selected from the group of compounds having the formula:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US476710A 1965-08-02 1965-08-02 Tobacco Expired - Lifetime US3372701A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US476710A US3372701A (en) 1965-08-02 1965-08-02 Tobacco
US476672A US3372699A (en) 1965-08-02 1965-08-02 Tobacco
US476709A US3372700A (en) 1965-08-02 1965-08-02 Tobacco
GB32034/66A GB1131183A (en) 1965-08-02 1966-07-15 Tobacco product and process for preparing same
FR71206A FR1487939A (fr) 1965-08-02 1966-07-28 Tabac amélioré et procédé pour le préparer
BE684814A BE684814A (cs) 1965-08-02 1966-07-29
DE19661692940 DE1692940A1 (de) 1965-08-02 1966-08-01 Verfahren zur Herstellung eines Tabakerzeugnisses
NL6610871A NL6610871A (cs) 1965-08-02 1966-08-02
CH1112266A CH492409A (de) 1965-08-02 1966-08-02 Tabakerzeugnis und Verfahren zu seiner Herstellung

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US476710A US3372701A (en) 1965-08-02 1965-08-02 Tobacco
US476672A US3372699A (en) 1965-08-02 1965-08-02 Tobacco
US476709A US3372700A (en) 1965-08-02 1965-08-02 Tobacco

Publications (1)

Publication Number Publication Date
US3372701A true US3372701A (en) 1968-03-12

Family

ID=27413389

Family Applications (3)

Application Number Title Priority Date Filing Date
US476710A Expired - Lifetime US3372701A (en) 1965-08-02 1965-08-02 Tobacco
US476672A Expired - Lifetime US3372699A (en) 1965-08-02 1965-08-02 Tobacco
US476709A Expired - Lifetime US3372700A (en) 1965-08-02 1965-08-02 Tobacco

Family Applications After (2)

Application Number Title Priority Date Filing Date
US476672A Expired - Lifetime US3372699A (en) 1965-08-02 1965-08-02 Tobacco
US476709A Expired - Lifetime US3372700A (en) 1965-08-02 1965-08-02 Tobacco

Country Status (6)

Country Link
US (3) US3372701A (cs)
BE (1) BE684814A (cs)
CH (1) CH492409A (cs)
DE (1) DE1692940A1 (cs)
GB (1) GB1131183A (cs)
NL (1) NL6610871A (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6557561B1 (en) * 1997-10-24 2003-05-06 Japan Tobacco Inc. Cigarette paper having a flavorant which improves sidestream smoke smell, and a cigarette

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3884247A (en) * 1967-10-18 1975-05-20 Firmenich & Cie Tobacco compositions employing flavoring agents comprising unsaturated butyrolactone derivatives and precursors thereof
US3623489A (en) * 1969-11-18 1971-11-30 Int Flavors & Fragrances Inc Tobacco smoking article
US3944679A (en) * 1973-04-13 1976-03-16 The Japan Tobacco & Salt Public Corporation Process for imparting a coumarin-like aroma and flavor to tobacco, foods and drinks

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766147A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US2872360A (en) * 1957-03-13 1959-02-03 Reynolds Tobacco Co R Tobacco

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766147A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US2872360A (en) * 1957-03-13 1959-02-03 Reynolds Tobacco Co R Tobacco

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6557561B1 (en) * 1997-10-24 2003-05-06 Japan Tobacco Inc. Cigarette paper having a flavorant which improves sidestream smoke smell, and a cigarette

Also Published As

Publication number Publication date
BE684814A (cs) 1967-01-30
GB1131183A (en) 1968-10-23
NL6610871A (cs) 1967-02-03
US3372699A (en) 1968-03-12
US3372700A (en) 1968-03-12
CH492409A (de) 1970-06-30
DE1692940A1 (de) 1972-03-30

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