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Determination of Methyl Nitrite in Cigarette Smoke

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Determination of Methyl Nitrite in Cigarette Smoke Determination of Methyl Nitrite in Cigarette Smoke C. H. Sloan and B. J. Sublett Research Laboratories, Tennessee Eastman Company, Division of Eastman Kodak Company, Kingsport, Tennessee, U.S.A. Tobacco Science, 1967, 11-5, p. 21-24, ISSN.0082-4523.pdf Introduction The gas-liquid chromato­ sulfanilic acid solution and Methyl nitrite has been identified graphic column was a 3/16 it was diluted to a volume o.f in cigarette smoke by Phillippe and in. copper tube 10 ft in length one, l with distilie'd water. Hackney ( 3). They collected smoke which wa.s packed with 60-80 The reagent solution should from several cigarettes, fractiona,ted mesh Chromosorb Vil uni­ be sto,red in an amb~r bottle. the smoke -components, and, by using formerly impregnated with 20 2. Methyl nitrite----a gas train infrared spectros.copy, identified and percent by weight 3,3'-oxydi­ was assembled that consisted estimated the amount of methyl ni­ propionitrile. The· column: respectively of a finger-type trite in an isolated fraction. was operated at room tem­ reactor containing five ml of perature. This paper describe,s ia relatively methanol; a finger-typ.e trap simple, rapid technique Which util­ A thermal conductivity cell containing a solution of (Gow-Mac, W-2 tungsten fila­ izes gas-liquid chromatography and KMnO,, NaNO., and Na2 H­ spectrophotometry to isolate and ments) operating at room PO,; a drying tube,filled with measure methyl nitrite from the temperature (150 ma on the indicating Drierite- and an­ smoke of one cigarette. The spectro­ bridge) was used as the de­ hydrous MgSO,; and an emp­ photometric method involves the use tector. Helium was. used as ty finger-type trap, cooled to of the well-known Griess reagent the -carrier -gas with a flow approximately -70°C with for determining ni,trite as reported rate through -the column of dry ice and iso,prop.yl alcohol. by Saltzman ( 4). 40- ml per min. A mixture of nitrogen diox­ 3. Spectrophotometer-A Beck ide and air was passed Materials and Methods man Model B spectrophotom­ through the system and the Appclratus. eter with two 10-mm cuvette.s methyl nitrite formed was was used. condensed in the ,cold trap. 1. Smoking machine----------,Cigarettes 4. Cambridge filter assembly­ After app1·oximately two ml \Vere smoked on an automatic A Cambridge filter holder with of condensate had formed in smoking machine which was 45-mm Cambridge filter pads the trap, the trap was. remo¥ed a modified version of the one (CM-113A) was used. from the gas train., cooled described by Mumpower, Kie­ with liquid nitrogen, and the fer, and Touey (2). Figure 1 Reagents. volatile gases wer•ei removed 1s a diagram of the machine. under a reduced pressure of 2. Gas chromatographic equip­ 1. Griess reagent-Five grams 0.1 mm. The methyl nitrite ment-Figure 2 is a diagram of sulfanilic acid was placed was transferred to .a,.[l evacu­ of ~he gas chromatographic in a one-1 volumetric flask. Six ated stainless steel eytinder by eqmpment and the sample hundred ml of water and 140 attaching the cylinder to ,the inlet system. The apparatus ml of glacial acetic acid were cold trap, immersing the cylin­ consisted of a gas sampling added, and the mixture was valve, a gas collection trap, stirred until the sulfanilic acid der in liquid nitr€ligen, and a gas-liquid chromatographic dissolved. N-1-Naphthylethyl­ allo,wing the methyl n.itri,te to column, and a detector. The enediarnine dihydroch1oride distill from the trav into the ?'as coHection trap was a 12- (0.2 g) was placed in a 100- cylinder. This o-peration fur­ m .. length of coiled ¼-in. ml volumetric flask and was ther purified the sample since stamless steel tubing at­ diluted to a volume of 100 ml methyl nitrate and other less tached from the ends of the with distilled water. Twenty volatile· materials which may trap to• the gas sampling ml of the N-1-naphthylethyl­ have been formed du ring the valve~ :with two 6-in. lengths enediamine dihydrochloride reaction were not distilled of ~s-m.-o.d. Teflon tubing. solution was added to the from the cold trap. A sample (Tobacco Science 21) of the methyl nitrite was chro­ mate.graphed on the column previously described. The ab­ ._ ____.I Tl MER sence of e·xtraneous peaks in­ ADJUSTABLE dicated the sample was rela­ BLEED VALVE ORIFICE tively pure. Cigarettes. All the cigarettes used 0 FROM GAS in these experiments were 85, mm .. ...COLLECTION in length, conditioned to 12-% mois­ • CHAMBER ture content, and each group weighed ±20 mg of their average TO weight. AIJ the cigarettes were ~ACUUM smoked to a 30 mm butt length. Calibrcttion Curve for Methyl Ni­ trite. A benzene solution contain­ ing 3.5 ± 0.1 mole percent methyl ni­ trite was prepared by passing methyl nitrite from a storage cylinder into benzene·. The concentration of methyl nitrite in the benzene solu­ Tobacco Science, 1967, 11-5, p. 21-24, ISSN.0082-4523.pdf tion was determined with a Varian A-60 NMR spectrometer. The concentration of methyl ni­ trjte in micrograms per milliliter was Figure l. Smoking apparatus. calculated from ,the equation: Ccmc o,f methyl nitrite, µg/ml = l\I.W. CH,ONO TO -------X SMOKING M.W. Benzene MACHINE Moles CH,,ONO ---------- X TO SMOKING 4-WAY 100 -- moles CH,ONO MACHINE CYCLE VALVES Density of Benzene X 106 One ml of the benzene solution con­ taining 25,300 µ.g of methyl nitrite -s;_ ,vas pipetted into a volumetric flask ....___ATTACH GAS and d·iluted to 100 ml with benzene. ~ /' DETECTOR BOTTLE Six duplicate aliquots of 0.1, 0.2, 0.3, CIGARETTE SOLENOIDi 04, 0.5 and 0.6 ml of this solution HOLDER NEEDLE VALVE ,iv·ere pipetted into twelve 25.0 ml AND volumetric flasks, each containing 50 CAMBRIDGE ml o-f Griess reagent. The solutions FILTER ,vere· allowed to stand 15 min until maximum color developed and then were diluted to 250 ml with distilled GAS BOTTLE water. Absorbance wa,s re·ad on the TRAP COLUMN spectrophotometer at 550 mµ. with Griess reagent and water as the blank. The calibration curve shown Figure 2. Multiple-puff sampling apparatus. in Figure 3 was prepared by plot- ABSORBANCE 0.4 ting absorbance versus µg of methyl the Beckman spectrophotometer at a nitrite. wavelength of 550 mf'. 0.3 Calibmtion Curve for Nitrite. A calibration curve with a range of 1 to 120 /J,g of nitrite was prepared Procedure 0.2 from spectrophotometric measure­ The Cambridge filter holder was ments of color produced by the reac­ attached to the gas sampling valve tion of aliquots of sodium nitrite so­ as shown in Figure 2. The gas col­ 0. l lution with Gries.s reagent. The ali­ lection trap (stainless steel tube) quots of .sodium nitrite .solution were was immersed in a deiwar flask filled with liquid nitrogen and the o~~-~~-~~-~~ combined with 50 ml of Griess re­ 0 24 48 72 96 120 )44 168 agent and allowed to react 15 min. gas-. valves on the smoking machine ,METHYL NITRITE, f-lG. The ·samples were diluted .to a vol­ and gas collection trap were ad­ ume of 250 ml with distilled water. justed to take a 35 ml puff of two­ Figure 3 . .rCalibration curve for methyl nitrite. The optical density wa.S read from sec. duration at the rate of one puff (Tobacco Science 22) per min. The solenoid valve at­ duced pressure, was vented to the tached to the gas collection trap atmosphere to fill the bottle with air. The gas bottle was then shaken was synchronized to open and close NO with the solenoid on the smoking for 15 min to allow the characteristic machine. This prevented the vacu­ red-violet color to· develop to maxi­ um created by ,cooling the gas col­ mum intensity. After the contents of lection trap with liquid nitrogen the bottle were emptied into a 250- CH30NO from applying a continuous draw to ml volumetric flask, the bottle was the lighted cigarette and limited the washed twice with distilled water puff to a 35 ml volume of two-sec and the washings were added to the duration. The cigarettes were flask. The solution was diluted to a placed in the Cambridge filter total volume o.f 250 ml with dis­ holder and smoked to a 30-mm butt tilled wate·r. The absorbance was 1ength. Cigarettes were then re­ determined spectrophotometrically l 0 moved and five puffs of air taken against a blank o,f Griess reagent TIME, MIN. through the filter assembly to sweep and water at a wavelength of 550 re.:;idual vapors into the gas collec­ m0. Figure 4. Observed chromatogram of methyl nitrite. tion trap. The gas valves ·were adjusted to Results and Discussion route the carrier gas through the The chromatographic column used bacco smoke. Due to the impure Tobacco Science, 1967, 11-5, p. 21-24, ISSN.0082-4523.pdf trap and chromatographic column. fnr the analysis of methyl nitrite in state of the eluate containing The dewar flask containing liquid cigarette smoke was a modification methyl nitrite, quantitative meas­ nitrogen was immediate1y rep.laced of the column described by Hanison urements cannot be made by peak with a dewar flask containing d,ry and Stevenson (1). This column ef­ height or peak area measurements. ice and isopropyl alcohol which fectively seiparates alkyl nitrites; Therefore, the chromatographic warmed the trap to approximately howeve•r, when it is used for the sep­ method in the procedure is used f -70°C.
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