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No. 63 Determination of Nicotine in Tobacco Smoke by Gas Chromatography

Date: 1973 (est.)
Length: 87 pages
00723028-00723114
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SCRT, SCIENTIFIC REPORT
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00723028/3114

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uew58c00

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CCDTPENPS, cont. * h`.umpower, R. C'. and Ji. E. Kiefer "Sorrz Factors, That Affect the Filtrationn of'Nicotine From.Cigarette Smoke10, Tobacco Science, VoI. XI:: pp. 144-147., Palmer, A. M. "The Determination of Organic Acids in Tobacco", Tobacco Science; Vol XVTi:p. 58. Sugawaz°e,. S.,, U. Kobashi and HoSakuaai "Studies,on the Chemical Evaluationn of'Tbbacco Quality. III Eva.luation of Tobacco 6?uiality from Gas Chromatographic Analysis of Particulate Phase of the Cigarette Smoke", Tobacco Science„ Vol XVI:pp.. 95-97. Weeks, W. W;. D. L. Davis, and L. P. Eush "Gas Chromztographic Separation of Tobacco Allraloids1°, J. Chromatograph; vo. 43:pp. 506-509. ABS71ACTS fr?I'SCELLANECUS * Massingill, John L., Jr., and Hoe E, Hod~kins "Gas Liquid, Chromatograph of Alkaloids Using Capillary Cb7:umns and Four Packed Columns°, Analyticall.Chem:istry, Vo.. 37:pp.95Z-955
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CONTENTS ARTICLES Bangarayya, M.. "Total Alkaloids in Tobacco - A Simple and Rapid Methodd of Determination"„ Tobacco Science; Vol. XV:pp. 114-115. Bates, William W. "Determination and Reporting of Total Particulate Matter, Water In Total Particulate.Matter, and Nicotine in Cigarette gnoke"',. Tobacco Sci'ence, Vol XII:pp. 192-196. Bush,. Lowell P. "Quantitative Analysis of Tobacco Alkaloids by Gas Chromatography"', J. Chro[catogcaphy, Vol. 73':pp- 243-247. Ch.arles, J. L. "Automated Determination of Nicotine in Total Particulate Matter of Cigarette Smoke"'. Tobacco Sc_ie Vol XII]]:pp. 54-58. Collins, P. F. "Determination of Nicotine Alkaloids in Tobacco Using,the Autoanalyzer!',Tobacco Science, Vol XIII:pp..7,9-81. Dietz, W. A. "Calibration Data for Gas Chromatographio Analysis of'Phenols",, Journal of Chromatographic Science, Vol l0:pp., 423-ii24. ~ Harvey„ W. R'. "Automated'Determination of Reducing Sugars and Nicotine Alkaloids on the Same Extract of Tobacco Leaf", Tobacco Science, Vol XIII: pp• 13-15. Harvey, W. R. "Nicotine Alkaloids in.Tobacco Leaf, Cigarette Filler, and Particulate Matter of Smoke by Acid-Methanol!.Extraction"; Tobacco Science, Vol 7C[:pp. 84-86. Jarrel, J. E. "A Study of the Ma;jor Gaseous Constituents.in the Mainstream Smoke of a Cigarette". Tobacco Science, Vol IX:pp., 5-11. Lyerly, Larry A. "'Direct Vapor Ch.romatographic Determination of Menthol, Propylene Glycol, Nicotine and Triacetin in Cigarette Sraoke",, Tobacco Science, Vol Xl:pp. 49-51.. Mann, J. E., Jr. P. M. Pederseny E. S. F.arlow,,and H. D. Downs "A Method for Determining Nicotine or Phenol in Cigarette.Smoke by Gas Chromatography", Tobacco Science., Vol. %I:p. 51. ~ *Nacmdrstrand; Kent, John M..Jiuntunen, and Allen R. Hennes "A Method of' ~, Collection of Gas-Liquid Chromatographic Effluent with.Cigarette ~ Filter Tips", Analytical Biochemistnj, Vol 27:pp. 172-174I. Q ~ O
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rzg-m1 erlenmeyer flask and containing the appropriate. te mixture was mechaniuallv' td dispersed by shaking thc. No. i fi1ter paper. ro ml of. nd, approximately n fZl was' f nornicotine;, anabasine andl as reduced to approximately he:great difference in quanti- atabine) and nicotine present ipropriatee amount of internal cco tissue by dissolwing.the stion on tobacco at.a rate of o sprayed with ethyl acetate .fined~abo.-e. - t _.,. trot~ .rb \t" .vas superior to baccoo-alkal'oids. To maximizc tobacco alkaloids one must jection of. exact volumes and ion was accomplished by use dge of the relathi've detector response (RT6'R) of.the four greatest percentage standard he.smallest deviation (x.o"p) otnetintes significantly,, witnh q cleanliness of detector, and each detectorr and eachl set of ticc alkaloid sample with the h differences. .ndependent of the presence of f two alkaloids orr one alkaloid 14 A PLAHEtOE22ATION'DETECTOF NOTES and the internal standard were eomparedl for their response. Each alkaloid was tested ~ with the internal standard,..and.the alkaioids; with the exception of'anatabine;.were. 1.tested.in all possible.combinations': Fig. ri iss a summaryof these comparisons. Linear ~ responses~ and zero intercepts w ere observed'for all comparisons. These results would . not bee expected if component interaction occurred or ikregulareomponent loss' 3- occurred; thus, the detector response for each alkaloid wasindependent of the: other 1: alkaloids in the samole. y ' Fig: x. Relative weight and peak area response.for'anabasine . I' (O)y and quinoline;mco[uie (p)',. _ ~ nointeractionoccurffed l ta dardbecause l t d th i t li ' ' i erna s n . ec e as e n newas se ; Qu no -, with the alkaloids and its suitablee retentiontirne. With the exception of nornicotine. ' theRit?R waegreater than o45 and thequantities of quinoline used could',approximate~ thee concentration off the alkaloids in tobacco tissue. If the RTVRR for quinoline' is assumed as one relative.toe the other alkaloid components;, the concentration of any . R WRa x A4 CA ~ C~ AI A s f ~ alkaloid component is given by .. . ... . . . .. three month period. n = nnmtwr` ~' whereCA.= the unknown concentration of the alkaloid.component„Cp- concentra- ', alkaloids, wliereas the totat alkaloids.det'ermined by steam distillation were expressed.. ' ' asnicotine equivalents. The GLCsummations were 3.0 to 6.6 % greater than totalI.alkaloids determined by steam distillation. The largest standard deviation for thee ton ofqumolme, R6f RA = relatlve detector response off the alkalotd component;, Ad = the peak area of the.alkaloid component,.andAQ = the peak area of'~quinoline.. Theprocedbre.was tested on.several tiiolbgical samples..Alobacco sample was . spikedwith.two levelsof alkaloids and the alkaloid content determined (Table II), , ~ The total:alkaloid5 determined.by the!GLC method are a summation of the'individual . J. CArnmah+gr:,, 73(I972) 2i3-Q47'
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,: o- Study of the Maj®r Case®us Constituents in the Mainstrearn Smo of a Cigarette J. E. Jarrell and R. de Iia Burde Research Center, Philip M'orris, Ineorporafed', Richmond, Virginia, U.S.A. R'I O.! rngun I. ModiLed therrnel condudrviFy Cell molecutar siiere .c6tuinM1 (Tobacco Sr.ienme 5) 3i11Ca gel calumn \. ?r -W:::_ '.- phere surrounding thebunning ma-~ 4oductiom `' -(2,4,5)_Most.of these, however,.were i rn .'terial or the temperature att whichconcerned.with the concentrations of .'. -:Therate of pyrolytic product for- _thematierial is~ bmrned affect the bal-.the major gases in totai,mainstream. _. .mation during theburning, of'.or- anceofpyrolytie.products (10). smoke and did not eonsidersuch ~ ~ganuc material has beenn shown to be :.-Several studiess of the pyrolytie - fact'orsas the:e ratee of formation of . . relat'ed' t'othe burning conditaons- products formed during the smokung, the.gases dhringthe.course.of smal . - 41,7)..Changes in either the atmos-~of cigarettess have been reported'ing; the dilution off tMemainsteam, RISfRy REFERENCE THERMISTORS DI H-D2 DETECTING THERMISTORS'
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''Z ^~' ~minatfon of alkaloids in tobacco smoke the sample must be chromato h d i , ~ _, grap e pr or cnROaArocsAPHx AND sxEASIw-.;;. ~ to addition of quinoline becaase smull amounts of cndngenovs quinoline are present. DeparhneR! of -1,rm7omv, .Loryv7:LL P. BHSH, AnafabineSumrna[ion -- -.; 'LBYyyygl0n, IiV..jOjoS (U.S.A.) 2W l ~ a (NgrG)'.,,. ; . .... . . 54F-4'8 21-69 ..~1F, :..._. _. 768 f 0 ~ 32~38' . 954 f 18 . . 42.62~. 20,_5 ~ [-L. D. QUIS,~J~..Org. Chem.. 24 (1950) '9I+F. . . :' ~ . ~ ~ . . I 21 'W. L. ALWORin, R'. C. IDESELMS ASD H. RAPO40R'r; J. Amel..Ckbm. Sae.,. 86 (/964)', l6o$. ' . 13, {V. L. ALwoRtH AND H. RaPOPOa'e,.Arch. Biachea:,Biop&ys., rie(u965) 45. - ' 314- 1 4; A. A3ASiASOY',. r, G: MOSHNACHEPAN:DNL. A. SHERSiYACKH, Bnlg, TyUtyun, I,{ (f963) SL.. 4o.Su 5 J.Y:GAHO~ .J.GAtALIN,.R.BADRE,.C.I7USAS,A.WTIALA.ANDR-GUILLERPtE'.AmI.PAann.Fr.,.. : . ... . .. . . . . _. . . 28 (797a) 581. 6' Y. KOBASxr AND 3t. WA'rAVASa; BvmsaAi Xyaku (jap. ARal.), 13 (1964) 1243. 7 J. L. 1SwssL\eILL, JR. AND J. E'. HouGRlss, A'.nafi.Chenl., 37 (1965):952. - 8N. L. hjCNIYER', K. HL RAISINGHANI, S. POiASHIYH AND R. I. DORFMAB', Nalule, 208 (1965)' ~ ~ 9'. H. P. HARRE AND'C. J. DRER-S. FKSenlus:'Z. AnaF. C/KM.,. 242 ([963) 248: _ -. .. : , :. . . . . .. . . . . ~. ~ . ~ 788. ~ . . ~ . . Io~.N..YASDSIArsV:.Agr..Biol.Chcm.,3~:I(I967)~x44[. - ...~ .. . ~ II ~. W. W. WEexsl D..Il. DAVCS AsD L. P. Bcsx, f:.CA.omafogr., 43 (I969)~ Sob- - I rz~~. L. A. hveRLrIr, (k967) 49- , Tobacco Sci., ' , . ~..-I3 H. JACIN, J4 \[..SLASSRI Az.D R. JL 3losev, .4na7. Cdim. Arfa, 41 (I963) 347. nANPLES OF'DIFFERENt'ALR'ALOIU F,.I4 N. YASVaIASSUAND.T.37cRAVAxA,.HatanoTab:.Esp.Sfa..Bdt., 63 ([g69) 75.. .. -f 15 C. J, KELLEx, L. P. BUSH AxDC. GnvxnvALD, J. Agi. Foad'Chem.,. 17 (sg69) 3 ~_ ~ofabine ~_4D8' f 7-0 . . ...f2•39 f n.I3J"Ia' d ,.35.3'± 1 40 % average) and the'e smallest GLC method, accuratel'yand tobacco alkaloids from plant s with greatly different quan- Chee standard deviation of tlu• ings indicate good precision of content. The accuracy of the Fuse: of'thelack of valid com- FsNos. a and.3, .- our laborat'ory for analysis nf Ritude'of difference'e betn-Den ssitates twoextiactions per e approximately equal to the min ted or minimized it :Hl Is aatogvapb, Por dctur- I6 L. S. E2nRE,.J. Gas~Clliomalogr.,. x([963) 36. .. ~~ ~. Received J!une 26th,.I972 . -.~.~....
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a-FT.C. pad holder b-denta0 d'am. O'-r6np c-eupport cyiinder,dam exT'end'ed : d-euppert dylinder,dam'ryiractedl dam was attached to the plastic cyl-t'o establish a standard curve. The The seeondmeasurement determined ;ted of 3er, a apling .ontrol acuum n. An : cali- 'C was a eam- in the sample .me of sample. Figure ;ample che:in- gasese sed in ciga- Dilu- t smalT pletely ge pad r with latr a ~ ` ade of in the hollow r. The i plastic.cylinder supported.thedental rechecked prior too each series of eoat.. The dihition of the smokeby lh dam and allowed the rubber to slide measurements by analyzing the oxy- air entering through the paper was ' forward and backward while still gen content in.fire ml of air. eliminated by covering the paper .' makinga tight seall on, the cigarette. Two types of measurements were with~the sliding dental dam.previous- . ~ inder by using a.rubber 0-ring. The calibration of the instrument was only the gases passing through the '~ Thitdiblfdi` ~ -ss apparaus mae it posseor, .conuctedon.cgarettesd smoked con- •ly d'escribed. B~etween samplings, the the cigarette to~burn either with or.--tinuously at air flows of:50; 75, 1'00}1 rubber dental dam waskept.at the _~ . without dilution of thee smoke by aiz. 125,, and 1501 . ml/min: The fii•stde- -:.butt end of the cigarette so thatt it : entering through the paper (1i'igure. termined the concentrations of the._ would not interfere withh the' ciga- 3) indiridual', gases in the mainstream iette's burning pattern. When the _ Smoking Vessel'~ . '.'smoke. The mainstream smoke in -charliue approached thee pointat-A special container wasuseds in . this case was composed' of the gases which -themeasurement wass to be. ` determining the effect of atmos- - passing, throughh the coall and the -taken, the dam wass pl'aced' approxi«'pherie nitrogen, on the...pyrolysisgases entering through the paper: 'inately two mm behind it. Themeas `. : prodhcts of thee burning cigarette ' ' -- --~ " (Fii 2) Thl t gure.ievesse:e was awo li'ter flask with three openings. One. ;of theopenings.(on.the side.ofthe~ .vessel) serveas an inlett for the`~ cigarette. A tank of artificial! atmos- -: phere equipped with a surge flask .' was attached to the.lower opening.-_ A vacuumpump.with a needl'evalve andi rotameter was attached to the ~;.upperoutlett The needle valve was. : nsed too regulate the draft through ...: the~ vessel. ~. - ~ . . .. . ~ . ' Coal:Vol'ume ~1Qeaeuremeat Equip- ~af aism ment ~ . ~ . . , _- Thermocouples ofplatinum-plati- : mum•10'.g'oo rhodium were usedd with :• a Sim-Ply-Tral pyrometen•Tifie pyro- - ~ meter~~was~. caliibrated over the: range~. - of 100°-500°C: ~ ~ ,` Ezyerimental Cigarettes~~~ ~ ~~-- Filteredi cigarettes 80 ~ mm. ~long, - were used in the: study., Alll cigarettes~~. '~. were~e with'un the~ weight range~ of: ~ 1.069 ' 0:04 gm:, and a.resistance~.to~. ~~ draw (RTD)~) range of 4.2~ - 4.6~~ i~n- chesof'water at 1050 ml/min. ~~ P'rocedure The gas chromatography unit wascalibrated each day using 1,.2',.and 3, mi samples of the Individnalgases, . F9ure 4:.Oeygen in }ofal meinsheam smoke. (TobaccoSeicnce
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LITERATURE SEARCH RECORD r ''LRCL8-73 DATE . 1-41-73 TIME ~ORMATION REQUESTED a. REQUESTOR Neil Thafigatd r #63 DEPT. 95-90 Detexmination of Nicotine in Tobaceo Sr:oke by Gas C:rc'matography Search terms: tobacco, G. C. Analyses Pyridine, G.C,'Analyses SOURCES USED 3-{ 1-Metk~yl-2-Pyrrolidenyl ;;~,i~.Chem5ical Abstracts 1966-1972 and 77(1-3) 1973 - . :~._. 45bacco Abstracts 1971-1972 }i ~r!( Journal of Chromatography 1972 Jotirnali of' Chroi a.to . ~c.~ Science 1972 Tobacco Science 19b5- ' an anua-y ~ . :..1. ... .' -~ : ::. . : . .~. .. .... .. . . A. C'.( gY: y RELEVANT DOCUMENTSIRETRIEVED ~M:v ,... . . +V~ ,a~:-._. .. _ . . . ... :..:., COMMENTS .:NNICAL INFORM'ATION 0. J. A.~A. ;. S P. PERSONNEL 'OPERATION PERFORMED' 7 hours 2 hoims 2~~ PROJECT NO. ITIM'E~ SPENT EXT. 239 a. TIME LIMIT;:..Y., Noon`2-1-73 .. Y .d S I:a 1.~ r'. DATECOMPLLETED 2-1-73f3 : M ~~.-
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nia- y a 'lea, the ider still n is vith n a tio ti in inei . md. _ fers aod. um- ~ .,. R9ure 2-A lyFmel r._era.r tredng. -bers of analyses. Second,. ou¢ extraction procedure per- mits mits water and nicotinee to be determinedi on the same - Cambridge filter pad, thus redueingthe amount of . machine smoking and sample. preparation required'd per' tar determination.. Third,, the. AutoAnalyzer baseline is stable;, and absorbances may be obtained. directEy from - the.recorder by using absorbancepaper: This'simple ,.peakheight to concentration relationship represents a considerablesavings in time overthemore.latiorious .. . background corrections required by'theultraviolet read- - out of' Willits. Furthermore,., by meanss off an automated -readoutdeviceit is possible to obtain a direct readout' with mg.of nicotine per cigarette printed.on paper tape,, thus completely eliminating calculations. . • MATERIALSIANDi METHODS -- JApparatus~~ , ioo~ ~ Technicon: AutoAnalyzer with SamLler II, 15 icm .' < _ .-;:. flbw cuvette„ 460 mµ interference filters, half- ' - .;.~ length delay coil and dialyzer with Type C mem- . -a . ~ = _ ,,.- . .brane. '_..:~.._._ . . :. . ..-. _. . a oac - A; fh HTh M d' - r ur omas _.. Readout, n el 4 Concentration -C-8 Digital Converter and Printcr. . _Reageasts~~. - . . . . .. ~ . _ '..2-Propanol, reagent grade- . . _ _ .-: oso .~-Ethanol, anhydrous, reagent grade -I 'Moleculhr Sieve, Type 4A, 1/16t' pellets -. Cyanogen Bromide, Eastman White Label ' Aniline, Eastman Whit'eLabell :• Ci~tric Acid, reagentt grade. : , -- D'isodium Phosphace: reagent'.grade . , Nicotine4 Eastman White Label _. o2c - -~ ~ _ . BRIJ-35; 204?'a ~ ~ - .- Preparation of Solution. The extraction solventist prepared by piDettin¢2.0. ml of ethanol into 1 liiterof 7-propanol. This solution iss protected from the atmos. -o . ozo 040 . osoo.eo,_ i.oo 1.20 .i.ro 160 i.so eieve. In theevente theanalysis for water does not pre- 1 - - - - , . . , cede thenicotihe determination the internal~ standard r'9°ra 9-Hice}i„a ddi.ery, ,n9Lci9uraH. tS'and79 m.,-.aa.ia.a a..,aj.ethanol and the drying tiubemay be omitted. -: .Aita"' "' - The cyanogen bromidee solution is prepared by dis. -,'.Thebuffered aniline solution is prepared.by dissolw-sollving 20 g of cyanogen bromidein.. 1 lliter of'ing 11124 g of \a:•HPQJ, and.8.2 g of citric acid monohy- distilledwater' which, contains 0.5'ml5 of BRIJ-35 sur- -,drate in about 300' ml ofdistill'ed water anrl~ 0.5 ml of -factant. B~RIJ.45; in a,1 liter volumetric flask- Three m1 of aniline <i : %
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WASTE t TYPE.GMEMBRANE ROOM TEMPERATURE DIALYSIS 1/2 LENGTH TIME DELAY COIL ifym. 1-A u6.mnflc Ou.. dicqrom e1 }h. AutoAnclyur cAcn.N. SINGLE MIXING C0I'_ - Ym LoWERI LEVEL ,:.] UP?ER ILEVEL n 9 073 GREEN H20 -. TUBE SiZES(.nches) 040 WHITE SAMPLE4 5.RED AIR 065'BLUE 2-PROPANOL 065 BLUE nILUTEDSAMPLE 045~~. REDAIR 045 RED AIR 0G58LUE 2%BrCN MO(ING COIL ; WASTE WA$TiE ' (' pROPORTIONING PUMP 090.PURPLE-BLA'CK BUFFERED ANALINE PRINTER CONCE NTiRAT10N READOUT_ DIGITAL CONVERTER .081PURPLE.FLOWCELL WASTE ~TO SAMPLER II -- WASH RECEPTACLE 'COLORIMETER' RECORDER , AUTOMATED --' 15mm TUBULAR . READ OUTDEVICE SOLVAFLEX !/t 460mq. FILTERS - . .. ~ SAMPLER 70 RATE 2 I PERHGUR AUTOMATE® DE'E'E6ai3i11EdAT1Ord OF `~II11! TOTAL PARTICULATE MATTER Y:OiF CIGA6ZETTE SMOKE ` ~ 3i,ByJ. ILCHARLES, H. M. STAHR, and R. M. IKEDA - ~' .-Phdip Morris, Inc, Research Center, Richmond, Va., U.S.A. -, . . . -. . -... - .{.a. . .- , . .., .. -. ..INTRODUCnON I extract of ground tobacco leaf. Ann automated. procedure has been developed forr the Iin ourlaboratory we have routinely dpterminednic- - 'determination of nicotinein a, 2-propanol.extractof the otine in particulate matterofr cigarette smoke by a._ particulate matter of cigarettee smokee collected' onn a~modiffiication, off the methodGs of Griffith (3)) and Plea- -Cambridge filter pad. This, workwas.undertak+en in part ' sants et al (4).. ACambridae filter pad containing.g thebeeause the Federall Trade Commission's tar determina- ..particulate matter fromm four cigarettes smokedd under tion asset forth inn the. Commission's announcement of. -standard conditions is. irttroduced into a. Grifflith stilP, ~ July 21, 1967 requiresthes analysis of nicotine and water . containing hydrochloric acid. A clenn-up: distillation is 0 'uasmokeparticwlate matter. performed. Thecontents of the still: are made basic with ~ T.hemethod usesan. AutoAnalyzer with room temper- sodium hydroxide, andl the distillate is collected in a fV at'ure dialysiss and is based on the reaction of nicotine,., flask containing sulfuric acidl An ultravioiet:absorption (j cyanogenn bromide and anilinee toproducea coior. whose: spectium isobtain.eds on the distillate, and the nicotine Q- intensityis proportional to the nicotine concentration.. . content determined by themethod of Willits (5),. Stand.- r~a 18er et: al. (1):) have adaptedd the reactiom for use with-ardN are prepared from Eastman White Label nicotine. U! AutoAnalzer to determine the nicotine content of: This will be referred to ass the steamdistillation method. ."`sttteeeam:m distillates. Harvey et al (2) have modified Sad- The~e automated cyanogen brontidee method offers . Ber"s procedure to determine simultaneously the nicotinee several advantages over thee steam distillation methad---and reducing sugar content in an acetic acidLmethanol! First, the AutoAnalyzer is more efficient for large num- . (Tobacco Scienae 54) M . :...bersmits Cam macll tar e stab! 'the I peak cons back out , readl with thnss preF' 2'.pr; pher' sizvt cede etha Tl solbi'; disti: fact:

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