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

• a further object of this invention is the provision of a process for enhancing or otherwise improving the flavor, 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 processof 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 orwhich has been treated with a small amount of a compound selected from the group of compounds having the formula: i
• R and R are selectedifrom the group consisting of hydrogen and alkyl radicals with at least one of said substituents being an alkyl group.
• the alkyl groups are lower alkyl-radicalsbf from 1 to 4 carbon atoms'
• the compounds falling'within the scope Formula I of the generic Formula I are gamma-lactones having an alkyl substituent in either the alpha or beta position.
• R and R can be methyl, ethyl, propyl, isopropyl, butyl and isobutyl.
• Example I The synthesis of 13-metliylbutyrolactone (a) Hydrobromiination of methallyl chloride-A solution of 10 grams of methallyl chloride in 50 milliliters of hexane was saturated with dry hydrogen bromide at 0l0 in the presence of 1% benzoyl peroxide. The solution was washed several times with water and the organic layer was dried and concentrated, yielding 18.1 grams of 1-bromo-3-chloro-Z-methylpropane.
• Example lL-fi-Isopropylbutyro lactone Forty-two grams of 2-isopropyl-l,3-propanediol, boiling point l18l20/l0 mm. was saturated with anhydrous hydrogen bromide at 0 to 5 (about 4 hours) and the reaction mixture was distilled to give 26.8 grams of 1-bromo-2-isopropylpropanol, boiling point l02-l06/ 7 mm.
• Example lII.-p3-EthyZbutyrolactone The title compound, boiling point 59/1 mm., is prepared according to the procedure of Example II using 2- ethyl-1,3-propanediol in lieu of the 2-isopropyl-1,3-propanediol.
• the intermediate l-broma-Z-ethylpropanol had a boiling point of 84-86/ 8 mm.
• the final tobacco additive has the formula:
• Example I V.oc-Ispropylbutyrolactone Ethylhydrogenisopropylsuccinate (26.1 grams, 0.14 mole) was added dropwise to a solution of 5.5 grams of lithium aluminum hydride in 400 milliliters of absolute ether. After the addition was completed, the solution was refluxed for two hours, cooled, acidified with dilute hydrochloric acid, and extracted with ether. Concentration of the ether layer and distillation of the residue gave 7.1 grams of a-isopropylbutyrolactone, boiling point 96 100/ 8 millimeters, having the formula:
• the tobacco additives of the invention when incorporated into tobacco products impart a fiavor 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 provides a smooth smoke.
• the tobacco additive of Example 11 imparts an aroma and flavor which some characterize as a sweet, rich tobacco taste with the tobacco additive of Example III being similar; and that of Example IV imparts a sharp woody note.
• 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 0.001 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 ,Bdsopropylbutyrolactone in an amount to provide a tobacco containing 0.25 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 sweet rich tobacco similar to that found in a tobacco-curing shed, 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 US. 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.
• a tobacco product having added thereto and dispersed therein a small amount sufficient to improve the flavor thereof of B-methylbutyrolactone.
• a tobacco product having added thereto and dispersed therein a small amount sufficient to improve the flavor thereof of B-isopropylbutyrolactone.
• a tobacco product having added thereto and dispersed therein a small amount suflicient to improve the flavor thereof of B-ethylbutyrolactone.
• a tobacco product having added thereto and dispersed therein a small amount sufiicient to improve the flavor thereof of a-isopropylbutyrolaotone.
• 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 wherein R and R are selected from the group consisting of hydrogen and alkyl groups with at least one of such substituents being alkyl.
• 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 added in an amount from about 0.001 to 2.0 percent by weight of the product.

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)

Priority Applications (9)

Applications Claiming Priority (3)

Publications (1)

Family

ID=27413389

Family Applications (3)

Family Applications After (2)

Country Status (6)

Cited By (2)

Families Citing this family (2)

Citations (2)

• 1965
  • 1965-08-02 US US476672A patent/US3372699A/en not_active Expired - Lifetime
  • 1965-08-02 US US476709A patent/US3372700A/en not_active Expired - Lifetime
  • 1965-08-02 US US476710A patent/US3372701A/en not_active Expired - Lifetime
• 1966
  • 1966-07-15 GB GB32034/66A patent/GB1131183A/en not_active Expired
  • 1966-07-29 BE BE684814A patent/BE684814A/xx unknown
  • 1966-08-01 DE DE19661692940 patent/DE1692940A1/de active Pending
  • 1966-08-02 CH CH1112266A patent/CH492409A/de not_active IP Right Cessation
  • 1966-08-02 NL NL6610871A patent/NL6610871A/xx unknown

Patent Citations (2)

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