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Sample #10 was found to contain paraff in. wax sinoe its spectr ufn contained all the paraffin wax absorptions. It also, contained beeswax since ita spectrum has all the absorptions c.%iaracter istic of this material. 8amgle #10 therefore containes nyricyl cerotate and Wricyl palmitate, the principal components of beeswax. Also present is a conjugated nitr o derivative from 1440 1540 arsd 13 4 em a h1 her f t'- e ter fr oanas a a y s om ~ g ~ ba nds at 1741 and 1163 cm.-1; an ~h3iphatic ketone from bands _ 709 and 1150 cr~.-1- a carooxy.Iac acid from bands at 3160, 1,713, 1398, and 126t3 cm.'i; a secondary alcohol from bands at 3333, 1398, 1298, and 1093 c~s.-~-; and a primary alcohol from bands at 3435, 1421, 1298, and 1034 cm.-1 Wherever percentages of components present in a sample ara given, they were estimated from the relative intensities of the observed absorption bands. CFZEMICAI. CDiP0Ufi73S POUND TO DAIE IN GICARET2E T0$ACCO S1;"tUKB AND TARS (additions to-February 1955 ilist, Report #2141) Present . ., . •" -. 73. anthracene 74. pyrene (possibly) 75. butyl benzy3l phthalate 76. glyceryl p12;..halate 77. myricyl cerotate 78. myricyl palmitate Very truly yours, T1s,uid N. Kendall

d containing a C =C. Sample #7, in addition to a trace of anthracene, was found to contain about 5el- by weight of paraffin wax, about 301'. by weight of a higher fatty ester (butyrate or higher), a maleate ester, an aliphatic ether, an unsubstituted amide, a compound having ? C= CH2 unsaturation, and a para disubstituted benzene derivative. 6. Sample ~8, in addition to about L% by weight anthra- 1~- cane, was found to contain about 83% by weight of paraffin wax, about 5% by weight of a compound ha5ding an isopropyl grouping, about 2 or 3% by weight of an unsubstituted arnide, about 2% by weight•of an alipnatic ether, about 2% by weight of a carboxylic acid,.a , vicinally trisubstituted benzene derivative, and a. compound having trans -CH - CFi- unsaturation. ~ 7.Sample #10 was found to contain myricyl cerotate, myricyl palmitate, another higher fatty ester ' ~ (butyrate or higher), paraffin wax, a compound con- tainirg a conjugated nitro grouping, an a7.iphatic ketone, an aliphatic carboxylic acid, a primary alcohol, and a secondary alcohol. $, Paraffin wax was found to be the principa3l camponent, other than urea, in the 1-5 urea complex. Some type of an amide and the metal salt of an acid are also present. A large part of the darsmposed complex was found to be simply urea. DetaiYs: Samples #4,5,6,7,8,9, and 3.i, eluates from a basic alumina column, were concentrated to smal3l volume by heating on a hot plate. The concentrates were then cast onto NaCI plates and the remaining solvent (cyclohexane in most cases) evaporated Owing to the sruall amounts of sample available, after ositing the concentrates on 2taCI plates more solvent was added to the beaker from which the concentrates were cast, the residues dissolved and cast onto the same plates. This process was repeated --four or five times to be certain that all available sample was transferred to a NaCI plate. Rocksalt infrared (2 to 15 microns) spectra were then run on the cast films of samples. The spectra obtained from samples #6,7, and $ were measured and interpreted to the extent possible as to the chemical components they contained and where this was not possible they were interpreted as to the type of chemical compound they contained and the functional chemi- ca3 6~oupings present. No time was available to interpret the spectra of samples #4,~,9, and 11. Rocksalt infrared spectra were run on urea, pyrene, lso present is a fumarate ester, a monosubstituted about 10% by weight of a carboxylic acid, and ple #14 in the as-received solid state as capillary thickness. The presence or absence of eno, pyrene, and benzopyrene in samples #k,5,6,7,8,9,1fl, trd ~ '_3

11, and the 1-5 urea complex •rras determined with the conclusions found und e r Re su2ts . The 1-5 urea complex sample was divided in half. One portion was dissolved in hot water and filtered to remove the solu.ble urea. The insoluble residue in the beaker as well as the insolubles on the filter paper were dissolved in carbon tetrachloride, concentrated by heating on a hot plate, and the concnntrate cast onto a NaC1 plate. The infrared spectrum of this film showed that a large part of the sample was simply urea. The major namponent, other than urea, was found to be paraffin wax, since the spectrum contained all the absorption bands of this material. Some type of an amide is also present as indicated by a 1670 cm.-1 band, and the metal salt of an acid as indicated by-absorptions at 1374 and 1414 cm.-I No other components were observed in the spectrum wh+eh.was rather weak. The other half of the 1-5 urea complex sample was heated in a 30 ml.- beaker atop which was placed a 2iaC1 plate, The heating was continued until all the urea became molten. Observation then showed that a film of material had condensed on the NaCl plate. An Infrared spectrum was run on this film but the latter was so thin that no usefz7l absorption bands were found in. the resulting spectrum. The spectrum of sample #6 was observed to have two ester carbony3l absorptions. Comparison of this spectrum with the spectra of numerous known esters shovred that butyl benzyI phthalate and glyceryl phthalate were present since the u.nknovmn spectrum contained all the absorptions of these two esters. In addition sample frb was found to contain a fumarate ester from absorptions at 1720, 1257, and 1156 cm.-1; a monosubstituted amide from bands at 1660 and 1531 cm.-1; a carboxylic acid from bands at 1703, 1257, and 1412 cm.-1; and a compound containing a C -C from a band at 1639 cm.-d- Sample #7 was found to coritainn about 50% by weight paraf f,.n wax since its spectrum had all the absorptions character- istic of this material. In addition sample #7 was found to contaizt a higher fa:ty ester from bands at 1739 and 1166 cm.-j-; a maleate eszer f~°om bands at 1724, 1238, and 1155 cm.-l; an aiiphatie ether from the band at 1099 cm.-1; an unsubstituted amide from d-t 16'9 1400 and lljj cm -1 a~C = CH #ro b d t o o~nsa 1543, 1426, 1C1q9, 9C30, and 656 cm.-i; and a paza disubstittzted t ~ r, , , benzene from bands at 1632, 1$9$, 1500, 1492, and 836 cm.-1 ~ Sams Ze #8 was found to contain about 85% by weight ~' paraffin wax since its spectrum contained all the paraffin wax ab3orptions; In addition it was found to contain a vic2zaily trisubsituted benzene from bands at 1597, 1511, 1492, 771 and 718 cm.-1; a trans -C;i =CH- from bands at 1642, 1300, and 462cm.-1; ann unsubstituted amide"from bands at 1662, 1597, and 11$2 cm."1; an aliphatic ether from the 1127 cm.- band; a oarboxylio acid frcu the 1700 cm.-:- band; and an isopropyl grouping from bands at .'.378, 1367# 1342, I168, 1127: and 939 cm.-1

ssamples ~`"r4 column, on ~'sulfurie-r,. Dr. Harris B. Parmele, Director of Research P. Lflrillard Co., Inc. 1.I3. Birst Street jersey City 2, N. J. Report #21j7 e where these could not be uniquely identified the spectra were interpreted as to the type of compounds and functional groupings 1 DAY2t7 N. KEIIIIALL.. PH.D. C4N8itf.7tNa GNEMIBT AND 4PEOTAO8COPSGT INFRARED SPECFALkST. 9 and uenzol3rene. The indicated. No'time was availabhe to =nterpret the spectra of samples #4,5,9, and I1. Results: I. About 1% by weight of anthracene was found to be present in sample #8. Samples #6,7, and 11 were ~--' ~ each found to contain a trace of anthracene. No ar.thracerse was found to be present irt samples #4, y fifteenth monthly report, n a se e 4 and benzapyrene in the other ss ~ The 1-3 urea complex was decomp water and exawining the water i sample. The other half was hea a1lar:ing the vaporized material examining the condensate throug; 5,9,10, or the 1-5 urea complex.. No benzopyrene was found to be present in saroples rr4,3,6,7,8s9r10,1i, or the 1-5 urea camplex. ~ 3. No pyrene was found to be present inn samples #4,5, 6,8,9,10,11, or the 1-5 urea complex. The presence of a trace of pyrene in sample #7 is Dossible. One / cannot be certain of this, however, because the infra- m red spectrum of pyrene has only two strong bands aitable for characterization purposes. ~ igarette smoke during March 1955: apecTra were run on all eluates froi a basic alumina -sOlid neutral tar nitrated with 1-5 urea complex, urea, pyrene, bsence of anthracene, pyrene, mples mentioned was determined. by dissolving the urea In les by infrared on haif the the urea became molten, IdaCZ plate and its infrared spectrum. The in;2=ared spectra of samples #b,7,&, and 10 were interpreted to the extent possible as to the components they contained and NAN AVi. .-~ ..S.-_-.- ~ ~ f ar:thracene , was benzyl y+hi'itlalatl3. P