445 



4,830,028 

 7 8 |J 



order lo reduce Ihe pH of ihe mainstream aerosol dur- Chemicals, Eastman Kodak Co. (CataloguCy^o. 52. p 

 ing use of the article Mainstream aerosol is tlial aerosol 366, Chemical No. 1124973) To the 1-nicotine is 

 which is drawn through (he article and into the mouth charged about 10 g of sodium hydroxide pellets The 

 of the user. For example, for a cigarette, the mainstream flask is fitted with a heating mantle and equipped with a 

 aerosol is the mainstream tobacco smoke which in- 5 magnetic stirring bar. The nicotine solution is stirred 

 eludes the combustion and/or pyrolysis products of employing a magnetic stirring unit The nicotine is vac- 

 tobacco material uum distilled using a Todd Column packed with glass 

 By Ihe term. "pH of mainstream aerosol" is meant helixes, and the fraction distilled between IT" C and "^S' 

 that averaged per-puff pH of the whole aerosol as mea- C. at 10 mm Hg pressure is collected at a reflux ratio of 

 sured using the techniques described by Sensabaugh el 10 about 10:1. The collected distillate is water clear The 

 al in Tohacco Science. Vol XI. pp 25-30 (1967). which nicotine so purified using the vacuum distillation tech- 

 isincotporated herein by reference. Typical mainstream nique is employed in the preparation of the I-nicotine/- 

 aerosol pH for cigarettes ranges from about 4.5 units to levulinic acid salt, 

 about 8.5 units on average per cigarette. Into a 500 ml round bottom flask equipped with a ^ £n-b 



In referring lo a reduction in the pH of mainstream 15 magnetic stirring bar and healing mantle is charged 9 6 



aerosol, it is meant a lowering of the average pH of the g (0.6 mole) of levulimc acid. The levulinic acid is 



mainstream aerosol per particular smoking article. Such stripped employing a conventional magnetic stirring 



reduction is provided by the addition of an effective unit. The levulinic acid is obtained from Aldrich Cliem- 



amounl of the additive (e.g.. nicotine/organic acid salt ical Co.. Catalogue No 1984-85. p 672. Compound No. 



additive) Typically, the reduction in pH is a lowering 20 L-200-9. and is employed without further purification. 



of the pH by more than about 03 pH unit; preferably The levulinic acid is heated to about 50' C. in order to 



by more than about 0.08 pH unit. Typically, reduction provide a liquid form thereof, and the liquified conipo- 



in the pH of the mainstream aerosol does not provide a nent is subjected to stirring. To the liquified levulinic 



smoking article exhibiting mainstream aerosol having a acid is titrated 32.4 g (0.2 mole) of the purified 1-nico- 



pH significantly below 4.5 units. 25 line over about a 20 minute time period It is preferred 



The decomposition of the nicotine/organic acid salt lo introduce the nicotine lo the organic acid in order lo 



during use of the smoking article can introduce a reduc- provide an environment of excess acid to nicotine and 



lion of the pH of the mainstream aerosol depending thus promote the formation of salt A clear, viscous 



upon Ihe quantity and type of salt additive which is yellow colored material weighing about 100 g results 



incorporated into ihe smoking article. Thus, a certain 30 The product is sealed in a glass ampuole under nitrogen 

 balance, mellowing or marrying of the flavors culmi- The product is 1 -nicotine levulinate (as determined 



nale in a fuller bodied tobacco fiavor. strength and using infrared spectrometry), and has a nicotine lo levu- 



satisfaclion which is delivered to the user. Such a Ilavor linic acid ratio of 1:3 (as determined by a destructive 



enhancing characteristic is particularly desirable for distillation in a 10 percent sodium hydroxide aqueous 



highly air diluted or "ultra low tar" cigarettes. 35 solution, subsequent extraction using isopropanol. and 



The pH of the mainstream aerosol is infiuenced by a gas chromatographic analysis for nicotine) The salt is 



number of factors. For example, the pH of mainstream believed to have a structure substantially as generally 



cigarette smoke can be influenced by factors such as the described in FIG. 13 of the Perfetti reference, supra 

 type of tobacco or blend of tobaccos employed, the FXAMPLE 2 



type of processed tobacco (e.g.. volume expanded to- 40 



bacco or reconstituted tobacco), the configuration of Cigarettes incorporating varying amounts of the 1- 



the cigarette (e.g., Ihe filler low material, the degree of nicotine levulinate salt are provided using the following 



air dilution, the circumference of the cigarette, the type procedure. 



of wrapping material, etc.). the manner of drawing on Cigarettes having lengths of about 9"' mm and cir- 



or puffing the cigarette, and other such factors. 45 cumferences of about 24 85 mm have tobacco rod 



Cigarettes of Ihis invention generally deliver from lengths of 68 mm and filter element lengths of 31 mm 



about 05 mg to about 2 mg. more frequently from The tobacco rod includes a charge of tobacco cut filler 



about 0. 1 mg to .ibout 1.7 mg of nicotine when smoked weighing about 0.7420 g contained in a circumscribing 



under ITC conditions. Generally, FTC "tar" to FTC cigarette paper wrap which is sold commercially as 754 



nicotine ratios for cigarelles of this invention are less 50 Cigarelle Paper by Ecusta Corp. The filter element is 



than about 10. frequently less llian aboul 7, and in cer- manufactured using conventional cigarette filter mak- 



lain instances less Ian about 5 nC "tar" lo FTC nico- ing technology from cellulose acetate tow (2 7 denier 



line ratios for cigarettes of this invention often can per filament. 48.(XX) total denier) and circumscribing air 



range from about 3 to aboul 6. Typically. Ihe FTC "tar" permeable paper plug wrap having a CORESTA poros- 



to FTC nicotine ratio of a cigarette of this invention can 55 ity of 26.000 cm/min. The tobacco rod and filter ele- 



be lowered by up to aboul 80 percent of that ratio of a ment are aligned in an abutting, end-to-end relationship 

 similar cigarette not having Ihe additive incorporated ^ and secured together using lipping paper having a 



therein CORESTA porosity of 3 1 35 ml/min The tipping paper 



The following examples are provided in order lo is adhesively secured to Ihe filter element and the adja- 

 further illustrate the invention but should not be con- 60 cent portion of the tobacco rod. The tipping material 



sirucd as limiting the scope thereof. Unless otherwise circumscribes the length of the filter element and aboul 



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



described are manufaclureu using a Pilot Cigarette 



EXAMPLE 1 M.x\^e! from llauiii-Werke Korber & Co KG A ring of 



A salt of nicotine and levulinic acid is provided using 55 mech.inically provided perforations extends around Ihe 



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



Into a 1.000 ml round Iwittom flask is charged about treme mouth end thereof. Tlie perforations so provided 



350 g of I-nicotine provided from Kodak Laboratory yield cigarettes which are 50 percent air diluted. The 



