US3313307A - Tobacco - Google Patents

Tobacco Download PDF

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Publication number
US3313307A
US3313307A US447914A US44791465A US3313307A US 3313307 A US3313307 A US 3313307A US 447914 A US447914 A US 447914A US 44791465 A US44791465 A US 44791465A US 3313307 A US3313307 A US 3313307A
Authority
US
United States
Prior art keywords
tobacco
grams
flavor
ether
acid
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
US447914A
Other languages
English (en)
Inventor
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 US447914A priority Critical patent/US3313307A/en
Priority to DE19651517331 priority patent/DE1517331B1/de
Priority to BE674137D priority patent/BE674137A/xx
Priority to FR43187A priority patent/FR1461091A/fr
Priority to CH1768265A priority patent/CH463356A/de
Priority to NL6516702A priority patent/NL132788C/xx
Application granted granted Critical
Publication of US3313307A publication Critical patent/US3313307A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C07C59/205—Saturated compounds having only one carboxyl group and containing keto groups containing rings
    • 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
    • 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
    • A24B15/32—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by acyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups

Definitions

  • This invention relates to tobacco and has for an object the provision of a tobacco composition having improved aroma and flavor.
  • An additional object of this invention is to provide a smoking tobacco or product which has been treated in such manner as to impart an aroma or flavor considered pleasing to the smoker.
  • An additional object of the invention is the provision of smoking products such as cigarettes, cigars or pipe tobacco having enhanced flavor and aroma characteristics.
  • R is selected from the group consisting of alkyl and cycloalkyl groups of 1 to 8 carbon atoms and R R R and R are selected from the group consisting of hydrogen and alkyl groups of 1 to 4 carbon atoms.
  • a 3-liter flask equipped with stirrer, reflux-condenser and a pressure equalizing addition funnel was charged with 100 grams (1 mole) of finely pulverized, vacuum dried succinic anhydride and 400 milliliters of anhydrous ether.
  • a Grignard reagent prepared from 24.3 grams (1 mole) of magnesium and 151 grams of l-brornopentane in 300 milliliters of anhydrous ether was placed in the addition funnel and the system kept under dry nitrogen. The Grignard reagent was added dropwise to the stirred solution of succinic anhydride at such a rate as to keep the ether below reflux reflux temperature.
  • This compound was prepared via the Grignard reaction of 2-bromopentane (151 grams) and succinic anhydride (100 grams). Work-up of the Grignard reaction yielded 91 grams of oil that was dissolved in 1 liter of etherexane and adsorbed on a 7.5 centimeter column holding 1 kilogram of silicic acid, made up in a hexane slurry. Elution was 25-35% ether-hexane furnished 22.5 grams of the title compound whose structure was confirmed by its nuclear magnetic resonance spectrum.
  • This compound is reported in the literature as having a boiling point of 1305-1307 at 21 millimeters mercury pressure.
  • the additive compounds when employed in tobacco products in accordance with the invention impart flavor and aroma, particularly during smoking, which many smokers consider to be desirable in tobacco products.
  • 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 diflerently.
  • the compound 4-keto-nonanoio acid has been described by some as imparting an earthy mushroom-like aroma, while the 4 keto-decanoic acid produces a more delicate or light mushroom-like note.
  • compounds included within the broad scope of this invention where the alkyl substituents in the generic formula are somewhat diflerent may impart flavor and aroma to the tobacco products which may be somewhat different or difiicult to characterize on the basis of any recognized standard.
  • a camphoraceous note has been detected with 4-oxo-5-methyloctanoic acid and 3-cyclopentanoyl propionic acid.
  • 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 thereorraay.
  • a compound ethbraced by the generic formula given above is added to tobacco or applied to a smoking article or its component parts in amounts ranging from about 0.0005 to about 0.5 by weight of the product.
  • the amount of the additive is between about 0.001 and 0.02%. The exact amount to use will depend upon the amount of flavor and aroma desired and the particular compound or mixture thereof that is used.
  • the additives may be incorporated at any step in the treatment of tobacco but are 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 indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.
  • the manner in which the additives are applied to the tobacco is not particularly/important since it may be done in the form of spraying or dipping, 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 additives while they are being applied to the tobacco.
  • other flavor and aroma producing additives such as those disclosed in Jones United States Patent No. 2,766,145 and Schumacher United States Patent No. 2,978,365, may be incorporated into the tobacco with the additives of this invention.
  • an aged, cured and shredded burley tobacco is sprayed with a 1% ethyl alcohol solution of the 4-keto-nonanoic acid in an amount to provide a tobacco composition containing 0.01% 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.
  • the cigarette when treated as indicated, has a desired and pleasing aroma which is described by some as mushroom-like, and which is particularly detectable and pleasing in the main and side smoke streams when the cigarette is smoked.
  • the additives of the invention being appreciably volatile, can be incorporated with materials such as seam paste and the like which are used along with tobacco to form a product adapted for smoking.
  • the additive 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.
  • a domestic tobacco having added thereto a small amount sulficient to alter the flavor of the tobacco of a compound having the following formula:
  • R2 R4 Ri CC-OCOOH it. it. it. wherein R is selected from the group consisting of alkyl and cycloalkyl groups of 1 to 8 carbon atoms and R R R and R are selected from the group consisting of hydrogen and alkyl groups of 1 to 4 carbon atoms.
  • a domestic smoking tobacco having added thereto between about 0.0005 and about 0.5% by weight of a compound defined in claim 1.
  • a product adapted for smoking having added thereto a small amount suflicient to improve the flavor of the tobacco product of a compound defined in claim 1.
  • a tobacco product having added thereto between about 0.0005 and about 0.5% by weight of a compound defined in claim 1.
  • a tobacco product having added thereto between about 0.001 and about 0.02% by weight of a compound defined in claim 1.
  • a product adapted for smoking having added thereto between about 0.0005 and about 0.5% by weight of a compound defined in claim 1.
  • a product adapted for smoking having added thereto between about 0.001 and about 0.02% by weight of a compound defined in claim 1.
  • a process of improving tobacco which comprises adding thereto a small amount sufiicient to improve the flavor of the tobacco of a compound having the following formula:
  • R is selected from the group consisting of alkyl and cycloalkyl groups of l to 8 carbon atoms and R R R and R are selected from the group consisting of hydrogen and alkyl groups of 1 to 4 carbon atoms.
  • a process of improving the flavor of smoking tobacco which comprises adding thereto between about 0.0005 and about 0.5 by Weight of a compound defined in claim 9.
  • a process of improving a tobacco product which comprises adding thereto a small amount sufiicient to improve the flavor of the tobacco product of a compound defined in claim 9.
  • R is selected from the group consisting of alkyl and cycloalkyl groups of 1 to 8 carbon atoms and R R R and R are selected from the group consisting of hydrogen and alkyl groups of 1 to 4 carbon atoms.

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)
US447914A 1965-04-13 1965-04-13 Tobacco Expired - Lifetime US3313307A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US447914A US3313307A (en) 1965-04-13 1965-04-13 Tobacco
DE19651517331 DE1517331B1 (de) 1965-04-13 1965-12-10 Verfahren zur Verbesserung eines Tabakproduktes
BE674137D BE674137A (enrdf_load_stackoverflow) 1965-04-13 1965-12-21
FR43187A FR1461091A (fr) 1965-04-13 1965-12-21 Nouvelle composition de tabac
CH1768265A CH463356A (de) 1965-04-13 1965-12-22 Verfahren zur Verbesserung eines Tabakprodukts
NL6516702A NL132788C (enrdf_load_stackoverflow) 1965-04-13 1965-12-22

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US447914A US3313307A (en) 1965-04-13 1965-04-13 Tobacco

Publications (1)

Publication Number Publication Date
US3313307A true US3313307A (en) 1967-04-11

Family

ID=23778248

Family Applications (1)

Application Number Title Priority Date Filing Date
US447914A Expired - Lifetime US3313307A (en) 1965-04-13 1965-04-13 Tobacco

Country Status (6)

Country Link
US (1) US3313307A (enrdf_load_stackoverflow)
BE (1) BE674137A (enrdf_load_stackoverflow)
CH (1) CH463356A (enrdf_load_stackoverflow)
DE (1) DE1517331B1 (enrdf_load_stackoverflow)
FR (1) FR1461091A (enrdf_load_stackoverflow)
NL (1) NL132788C (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0103486A1 (en) * 1982-09-13 1984-03-21 Philip Morris Incorporated Smoking compositions
US4590953A (en) * 1983-01-26 1986-05-27 Givaudan Corporation Alkyl α-campholenates and dihydro derivatives thereof as tobacco flavorants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3884246T2 (de) * 1987-02-10 1994-03-03 Reynolds Tobacco Co R Zigarette.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0103486A1 (en) * 1982-09-13 1984-03-21 Philip Morris Incorporated Smoking compositions
US4481956A (en) * 1982-09-13 1984-11-13 Philip Morris Incorporated Smoking compositions
US4590953A (en) * 1983-01-26 1986-05-27 Givaudan Corporation Alkyl α-campholenates and dihydro derivatives thereof as tobacco flavorants

Also Published As

Publication number Publication date
FR1461091A (fr) 1966-12-10
CH463356A (de) 1968-09-30
DE1517331B1 (de) 1970-04-02
NL6516702A (enrdf_load_stackoverflow) 1966-10-14
BE674137A (enrdf_load_stackoverflow) 1966-06-21
NL132788C (enrdf_load_stackoverflow) 1971-06-15

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