466 



4,836,224 



11 12 



can be lowered by up to about 80 percent or that ratio ment are aligned in an abutting, end-to-end relationship 



ofsimilarcigarettenot having the salt additive incorpo- and secured together using tipping paper having a 



rated therein. CORESTA porosity of 3135 ml/min. The tipping paper 



The ToUowing examples are provided in order to is adhesively secured to the Alter element and the adja- 



further illustrate the invention but should not be con- ' cent portion of the tobacco rod. The lipping material 



strued as limiting the scope thereof. Unless otherwise circumscribes the length of the filter element and about 



noted, all parts and percentages are by weight. 3 mm of the length of the tobacco rod. Cigarettes so 



EXAMPLE 1 



described are manufactured using a Pilot Cigarette 

 Maker from Hauni-Werke Korber & Co. KG. A ring of 

 A salt of nicotine and levulinic acid is provided using '" mechanically provided perforations extends around the 

 the following procedure. periphery of the cigarette about 13 mm from the ex- 



Into a 1,000 ml round bottom Hask is charged about (jeme mouthend thereof. The perforations so provided 

 350 g of 1-nicoUne provided from Kodak Laboratory y,eid cigarettes which are 50 percent air diluted. The 

 Chemicals, Eastman Kodak Co. (CaUlogue No. 52, p. ^^ cigateltes so manufactured are designated Sa-nple Nos. 

 366, Chemical No. U24973). To the l-mcotine is i, 2. 3 and C-1, corresponding to the sample of filler 

 charged about 10 g of sodium hydroxide pellets. The material from which each cigarette is manufactured, 

 flask is fitted with a heaung mantle and equipped with a jy,^ r,„„ ^i^^i] employed in providing the tobacco 



magnetic stirring bar. The nicotme solution is stirred ,^ j, ;„ ,^5 fom, of strands cut at about 32 cuts per 

 employing a magnetic stimng unit The nicotine is vac- jp j^^. The initial filler material includes a blend of about 

 uum distilled using a Todd Column packed with glass , „, 3^^,^^ ,^b^^^„ ^^out 41 percent flue-cured 

 helixes and the fraction distilled between 97 C. and 98 ,„b,cco, about 32 percent reconstituted tobacco ma.e- 



^u " ^tT-^u^ pressure IS collected at a reflux ratio of ^,,_ ^^^ ,j^^, ,g ^^^„, q^^^,^, ^^^^^^^^^ .^he blend 

 about 10:1. The collected distillate is water dear. The ^„ ,„ ^ ^^ ^^^^ ^^^ ^^^^^ 



nicotme so punned using the vacuum distillation tech- 25 ,}.„,,„ •> ^ j rr 



nique is employed in the preparation of the 1 -nicotine/- _ ', . ... . ^,, ... . , ... 



levulinic acid wJt ^°"' '°'' °^ '*" "^"' ''"'^ ''''"''• "'^*' '°' ^"ghing 



Into a 500 ml round bottom flask equipped with a ^f° ^l ".' P'°^ided. The first lot i, treated with 20 g 

 magnetic stirring bar and heating mantle is charged 69.6 °^ "" '""."!°'Jr ''^"''""l' "^'^'""'l ^' »"°"f J°' '« 

 g (0.6 mole) of levulinic acid. The levulinic acid is 30 if""^.*",^ *° 8 of the 1-nicotme levulinate additive, 

 stripped employing a conventional magnetic stirring Th'.'hird lot is treated with 100 g of the 1-nicoline 

 unit. The levulinic acid is obtained from Aldrich Chem- '^vu mate additive. The fourth lot is not treated with 

 ical Co.. Catalogue No. I984-8J. p. 672. Compound No. '*" "■"•co«'"e 'evulinate additive and is employed for 

 L-200-9, and is employed without further purification. comparison purposes. 



The levulinic acid is heated to about 50' C. in order to 35 ''"« 1 -nicotine levulinate additive is applied to cut 

 provide a Uquid form thereof, and the liquified compo- ''""' " * '?"> """8 » ^'^'^ sprayer to apply all 

 nent is subjected to stirring. To the liquified levulinic "imture of water and additive. 



acid is titrated 32.4 g (0.2 mole) of the purified 1-nico- ^'^^ °^ "** ^°"^ ^°^ "' separately placed in sealed 



tine over about a 20 minute time period. It is preferred ?'=*''= •'»«' ""<* **°f'd »' ''^' ^ fo' 2 days. Then, the 

 to introduce the nicotine to the organic acid in order to *0 ''°'" '°" "' "=•> '"'""'l w"*! «'«'"' *^° 8 "f » ="' *"'er 

 provide an environment of excess acid to nicotine and mixture of about 75 parts volume expanded Burley 

 thus promote the formation of salt. A clear, viscous tobacco and about 25 parts volume expanded flue-cured 

 yellow colored material weighing about 100 g results. tobacco. The volume expanded cut filler mixture is 

 The product is sealed in a glass ampuole under nitrogen. added to each lot using a mixing drum in order to pro- 

 The product is 1-nicotine levulinate (as determined *' vide a well mixed blend having a moisture content of 

 using infrared spectrometry), and has a nicotine to levu- ilJO"' '2 percent to about 13 percent The resulting 

 linic acid ratio of 1:3 (as determined by a destructive blend provided from the first lot of filler material has 

 distillation in a 10 percent sodium hydroxide aqueous about 1 percent of the I -nicotine levulinate salt appfied 

 solution, subsequent extraction using isopropanol, and thereto (based on the filler conditioned weight) and is 

 gas chromatographic analysis for nicotine). The salt is designated as Sample No. 1. The resulting blend pro- 

 believed to have a structure substantially as generally vided from the second lot of filler material has about 3 

 described in FIG. 13 of the Perfetti reference, supra. percent of the I -nicotine levulinate salt applied thereto 



Cigarettes incorporating varying amounts of the I- (based on the filler conditioned weight) and is desig- 

 nicotine levulinate salt are provided using the following ,. nated as Sample No. 2. The resulting blend provided 

 procedure. from the third lot of filler material has about 5 percent 



Cigarettes having lengths of about 99 mm and cir- of the I -nicotine levulinate salt applied thereto (based 

 cimiferences of about 24.85 mm have tobacco rod on the filler conditioned weight) and is designated as 

 lengths of 6ft mm and filter element lengths of 31 mm. Sample No. 3. The resulting blend provided from the 

 The tobacco rod includes a charge of tobacco cut filler jo fourth lot of filler material is not treated with the 1-nico- 

 weighing about 0.74 g contained in a circumscribing tine levulinate salt additive, is employed for comparison 

 cigarette paper wrap which is sold commercially as 754 purposes, and is designated as Sample No. C-1. 

 Cigarette Paper by EcusU Corp. The filler element is The various cigarettes are smoked under FTC condi- 



manufactured using conventional cigarette filter mak- tions. Data concerning (i) FTC "tar," FTC nicotine and 

 ing technology from cellulose aceute tow (2.7 denier 63 FTC carbon monoxide, (ii) the "tar'Vnicotine ratio, (iii) 

 per filament, 48,000 total denier) and circumscribing air cigarette nicotine content, (iv) puff count, and (v) pH of 

 permeable paper plug wrap having a CORESTA poros- the mainstream aerosol for each sample are presented in 

 ity of 26,000 cm/min. The tobacco rod and filter ele- Table I. 



