US3334637A - Smoking product having flavorant additive - Google Patents

Smoking product having flavorant additive Download PDF

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Publication number
US3334637A
US3334637A US416923A US41692364A US3334637A US 3334637 A US3334637 A US 3334637A US 416923 A US416923 A US 416923A US 41692364 A US41692364 A US 41692364A US 3334637 A US3334637 A US 3334637A
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US
United States
Prior art keywords
tobacco
additive
percent
pyrrolecarboxaldehyde
flavor
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
US416923A
Inventor
Donald L Roberts
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
Priority to NL130041D priority Critical patent/NL130041C/xx
Application filed by RJ Reynolds Tobacco Co filed Critical RJ Reynolds Tobacco Co
Priority to US416923A priority patent/US3334637A/en
Priority to GB32140/65A priority patent/GB1072946A/en
Priority to DE19651517328 priority patent/DE1517328B1/en
Priority to CH1160565A priority patent/CH485425A/en
Priority to NL6510870A priority patent/NL6510870A/xx
Priority to BE668620D priority patent/BE668620A/xx
Priority to FR29028A priority patent/FR1445164A/en
Application granted granted Critical
Publication of US3334637A publication Critical patent/US3334637A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • 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
    • A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
    • A24B15/385—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom in a five-membered ring

Definitions

  • An additional object of this invention is to provide a tobacco which has been treated in such manner as to impart a subtle flavor which is pleasing to the smoker.
  • a domestic tobacco is provided to which has been added a small amount of l-methyl-Z-pyrrolecarboxaldehyde.
  • the above chemical herein referred to as Compound I, may be represented by the followingformula:
  • Compound I is a liquid having a boiling point of approximately 72.4 C. per 12 millimeters of mercury pressure and the following characteristics:
  • the designated Compound I is usually added to a domestic tobacco in amounts to provide a tobacco in which is dispersed about 0.001 to about 1.0 percent by weight of the additive.
  • the amount of additive is between about 0.005 and about 0.03 percent by weight in order to form a domestic tobacco having a desired flavor and aroma.
  • the preferred percentages may be somewhat less, however, if
  • the additive may be applied in any suitable manner and preferably in the form of a liquid solution or suspension by spraying, dipping or otherwise.
  • 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, cured and shredded burley tobacco is sprayed with a one percent ethyl alcohol solution of the above indicated compound in an amount to provide a to bacco composition containing 0.01 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.
  • the cigarette when treated as indicated has a desired and pleasing aroma which is detectable in the main and side smoke streams when the cigarette is smoked; this aroma is described by some smokers as an almond note.
  • the manner in which the additive is applied to the tobacco is not particularly important since, as indicated, 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 additive while it is 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 additive of this invention.
  • the additives of the invention can be incorporated with materials such as filter tip materials, seam paste, packaging materials and the like which are used along with tobacco to form a product adapted for smoking.
  • the additive of this invention can 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 of 1-methyl-2-pyrrolecarboxaldehyde suflicient to alter the flavor of the tobacco.
  • a domestic smoking tobacco having added thereto between about 0.001 and about 1.0 percent by Weight of 1-methy1-2-pyrrolecarboxaldehyde.
  • a domestic smoking tobacco having added thereto between about 0.005 and about 0.03 percent by weight of 1-methyl-2-pyrrolecarboxaldehyde.
  • a tobacco product having added thereto a small amount of 1-methyl-2-pyrrolecarboxalde'hyde sufiicient to improve the flavor of the tobacco.
  • a tobacco product having added thereto between 3 about 0.001 and about 1.0 percent by weight of l-methyl- 2-pyrrolecarboxaldehyde.
  • a tobacco product having added thereto between about 0.005 and about 0.03 percent by weight of l-methyl-2-pyrrolecarboxaldehyde.
  • a tobacco substitute having added thereto between about 0.001 and about 1.0 percent by weight of l-methyl- 2-pyrrolecarboxaldehyde.
  • a process of improving tobacco which comprises adding thereto a small amount of 1-methyl-2-pyrrolecarboxaldehyde suflicient to improve the flavor of the tobacco.
  • a process of improving the flavor of tobacco which comprises adding thereto between about 0.001 and about 1.0 percent of 1-methyl-2-pyrrolecarboxaldehyde.
  • a process of improving tobacco which comprises adding thereto in the form of a liquid solution a small amount of 1-methyl-2-pyrrolecarboxaldehyde sufficient to improve the flavor of the tobacco.
  • a process of improving tobacco which comprises adding thereto in the form'of a liquid suspension a small amount of 1-methyl-2-pyrrolecarboxaldehyde suflicient to improve the flavor of the tobacco.

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)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Description

United States Patent ()fiice 3,334,637 Patented Aug. 8, 1967 3,334,637 SMOKING PRODUCT HAVING FLAVORANT ADDITIVE Donald L. Roberts, Winston-Salem, N.C., assiguor to R. J. Reynolds Tobacco Company, Winston-Salem, N.C., a corporation of New Jersey No Drawing. Filed Dec. 8, 1964, Ser. No. 416,923 14 Claims. (Cl. 13117) This invention relates to tobacco and has for an object the provision of a tobacco composition having improved aroma and flavor.
It is well known in the tobacco art that the domestic tobaccos which are exemplified by burley, Maryland, fluecured, bright leaf or Virginia tobaccos are low in flavor as compared with so-called oriental or aromatic tobaccos which are imported from Turkey, Greece, Bulgaria, Yugoslavia, Rhodesia and Russia. Accordingly, it has been common practice in the tobacco industry to prepare blends of domestic and oriental tobaccos in order to provide cigarettes which have desired flavor and aroma characteristics. Accordingly, it is a further object of this invention to provide a domestic tobacco which has an enhanced flavor and aroma.
An additional object of this invention is to provide a tobacco which has been treated in such manner as to impart a subtle flavor which is pleasing to the smoker.
In accordance with one embodiment of this invention a domestic tobacco is provided to which has been added a small amount of l-methyl-Z-pyrrolecarboxaldehyde. The above chemical, herein referred to as Compound I, may be represented by the followingformula:
The chemical Compound I indicated above can be synthesized by the alkylation of pyrrolecarboxaldehyde. A detailed description of the synthesis of Compound I is as follows:
The procedure of Treibs and Dietl, Ann., 619, 80-95 (1958) was used in which 2-pyrrolecarboxaldehyde (52.4 grams) was converted to the sodium salt using metallic sodium in toluene. The sodium salt (50 grams) was then placed in 1000 milliliters of ether and 50 milliliters of dimethyl sulfate in 200 milliliters of ether was added dropwise. After refluxing two hours, the solution was filtered and the filtrate was stirred for eight hours with 50 percent aqueous potassium carbonate. The mixture was then separated and the dried ether layer was distilled. Vacuum distillation gave 15.2 grams [boiling point 76 per 11 millimeters of mercury; lit., boiling point 72.4 per 12 millimeters of mercury] or 25 percent yield of Compound I.
Compound I is a liquid having a boiling point of approximately 72.4 C. per 12 millimeters of mercury pressure and the following characteristics:
Infrared spectrum: 3100, 2940, 1660, 1310, 1212, 1086,
1053, 1021, 763, and 742 cmf Nuclear magnetic resonance spectrum: 7=0.44(l), 3.14
(2, multiplet), 3.80 (1, triplet), and 6.05(3).
Mass spectrum: parent peak at 109.
In accordance with this invention, the designated Compound I is usually added to a domestic tobacco in amounts to provide a tobacco in which is dispersed about 0.001 to about 1.0 percent by weight of the additive. Preferably the amount of additive is between about 0.005 and about 0.03 percent by weight in order to form a domestic tobacco having a desired flavor and aroma. The preferred percentages may be somewhat less, however, if
other flavorants imparting a desired aroma are also employed. The additive may be applied in any suitable manner and preferably in the form of a liquid solution or suspension by spraying, dipping or otherwise. 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. Likewise, it will be apparent that only a portion of the domestic tobacco need be treated and the thus treated tobacco may be blended with other tobaccos before the cigarettes are formed. In such cases, 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.
In accordance with one specific example of this invention, an aged, cured and shredded burley tobacco is sprayed with a one percent ethyl alcohol solution of the above indicated compound in an amount to provide a to bacco composition containing 0.01 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. The cigarette when treated as indicated has a desired and pleasing aroma which is detectable in the main and side smoke streams when the cigarette is smoked; this aroma is described by some smokers as an almond note.
It will be particularly apparent that the manner in which the additive is applied to the tobacco is not particularly important since, as indicated, it may be done in the form of spraying or dipping, utilizing suitable suspensions or solutions of the additive. Thus, 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. Also, 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 additive of this invention.
While this invention is particularly useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars and other tobacco products formed from sheet tobacco dust or fines which are well known to the art. Likewise, the additives of the invention can be incorporated with materials such as filter tip materials, seam paste, packaging materials and the like which are used along with tobacco to form a product adapted for smoking. Furthermore, the additive of this invention can 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.
Those modifications and equivalents which fall within the spirit of the invention and the scope of the appended claims are to be considered part of the invention.
I claim:
1. A domestic tobacco having added thereto a small amount of 1-methyl-2-pyrrolecarboxaldehyde suflicient to alter the flavor of the tobacco.
2. A domestic smoking tobacco having added thereto between about 0.001 and about 1.0 percent by Weight of 1-methy1-2-pyrrolecarboxaldehyde.
3. A domestic smoking tobacco having added thereto between about 0.005 and about 0.03 percent by weight of 1-methyl-2-pyrrolecarboxaldehyde.
4. A tobacco product having added thereto a small amount of 1-methyl-2-pyrrolecarboxalde'hyde sufiicient to improve the flavor of the tobacco.
5. A tobacco product having added thereto between 3 about 0.001 and about 1.0 percent by weight of l-methyl- 2-pyrrolecarboxaldehyde.
6. A tobacco product having added thereto between about 0.005 and about 0.03 percent by weight of l-methyl-2-pyrrolecarboxaldehyde.
7. A tobacco substitute having added thereto between about 0.001 and about 1.0 percent by weight of l-methyl- 2-pyrrolecarboxaldehyde.
8. A process of improving tobacco which comprises adding thereto a small amount of 1-methyl-2-pyrrolecarboxaldehyde suflicient to improve the flavor of the tobacco.
9. A process of improving the flavor of tobacco which comprises adding thereto between about 0.001 and about 1.0 percent of 1-methyl-2-pyrrolecarboxaldehyde.
10. The process recited in claim 9 wherein the stated percent is between about 0.005 and 0.03 percent.
11. A process of improving tobacco which comprises adding thereto in the form of a liquid solution a small amount of 1-methyl-2-pyrrolecarboxaldehyde sufficient to improve the flavor of the tobacco.
12. The process recited in claim 11 in which the small amount of the additive is between about 0.001 and 1.0. percent by weight.
13. A process of improving tobacco which comprises adding thereto in the form'of a liquid suspension a small amount of 1-methyl-2-pyrrolecarboxaldehyde suflicient to improve the flavor of the tobacco.
14. The process recited in claim 13 in which the small amount of the additive is between about 0.001 and 1.0 percent by weight.
References Cited UNITED STATES PATENTS 7 3,280,824 10/1966 Roberts 13l17 1 OTHER REFERENCES Chemical Abstracts, pub. by the American Chemical Society, vol. 53, No. 19, Oct. 10, 1959, 17998(i).
SAMUEL KOREN, Primary Examiner.
MELVIN D. REIN, Examiner.

Claims (1)

1. A DOMESTIC TOBACCO HAVING ADDED THERETO A SMALL AMOUNT OF 1-METHYL-2-PYRROLECARBOXALDEHYDE SUFFICIENT TO ALTER THE FLAVOR OF THE TOBACCO.
US416923A 1964-12-08 1964-12-08 Smoking product having flavorant additive Expired - Lifetime US3334637A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
NL130041D NL130041C (en) 1964-12-08
US416923A US3334637A (en) 1964-12-08 1964-12-08 Smoking product having flavorant additive
GB32140/65A GB1072946A (en) 1964-12-08 1965-07-27 Tobacco
DE19651517328 DE1517328B1 (en) 1964-12-08 1965-08-09 Process for improving a tobacco product
CH1160565A CH485425A (en) 1964-12-08 1965-08-18 Tobacco product containing 1-methyl-2-pyrrole carboxaldehyde
NL6510870A NL6510870A (en) 1964-12-08 1965-08-19
BE668620D BE668620A (en) 1964-12-08 1965-08-20
FR29028A FR1445164A (en) 1964-12-08 1965-08-20 Tobacco containing 1-methyl-2-pyrrolecarboxaldehyde

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US416923A US3334637A (en) 1964-12-08 1964-12-08 Smoking product having flavorant additive

Publications (1)

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US3334637A true US3334637A (en) 1967-08-08

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US416923A Expired - Lifetime US3334637A (en) 1964-12-08 1964-12-08 Smoking product having flavorant additive

Country Status (6)

Country Link
US (1) US3334637A (en)
BE (1) BE668620A (en)
CH (1) CH485425A (en)
DE (1) DE1517328B1 (en)
GB (1) GB1072946A (en)
NL (2) NL6510870A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3623489A (en) * 1969-11-18 1971-11-30 Int Flavors & Fragrances Inc Tobacco smoking article
US3828795A (en) * 1973-06-21 1974-08-13 Reynolds Tobacco Co R Tobacco product
US3996940A (en) * 1975-04-08 1976-12-14 R. J. Reynolds Tobacco Company Tobacco product
US5043348A (en) * 1987-04-24 1991-08-27 Cassella Aktiengesellschaft Pyrrolealdehydes, their preparation and their use

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3280824A (en) * 1965-11-03 1966-10-25 Reynolds Tobacco Co R Tobacco

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3280824A (en) * 1965-11-03 1966-10-25 Reynolds Tobacco Co R Tobacco

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3623489A (en) * 1969-11-18 1971-11-30 Int Flavors & Fragrances Inc Tobacco smoking article
US3828795A (en) * 1973-06-21 1974-08-13 Reynolds Tobacco Co R Tobacco product
US3996940A (en) * 1975-04-08 1976-12-14 R. J. Reynolds Tobacco Company Tobacco product
US5043348A (en) * 1987-04-24 1991-08-27 Cassella Aktiengesellschaft Pyrrolealdehydes, their preparation and their use

Also Published As

Publication number Publication date
CH485425A (en) 1970-02-15
GB1072946A (en) 1967-06-21
BE668620A (en) 1966-02-21
NL130041C (en)
NL6510870A (en) 1966-06-09
DE1517328B1 (en) 1970-04-09

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