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Alkylbenzenes in the C9 Fraction from Seven Representative Crude

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Alkylbenzenes in the C9 Fraction from Seven Representative Crude U. S. Department of Commerce Research Paper RP1839 National Bureau of Standards Volume 39, November 1947 Part of the Journal of Research of the National Bureau of Standards Alkylbenzenes in the Cg Fraction from Seven Repre­ sentative Crude Petroleums 1 2 By Alphonse F. Forziati 3 and Frederick D. Rossini This report presents the results of an analysis, by analytical distillation by t he A. P. 1. Research Proj ect 6, and by spectrographic examination by the Socony-Vacuum Laboratories, the Standard Oil Development Co. , and the Sun Oil Co. of the individual Cg alkylbenzenes (except 1,2,3-trimethylbenzcne) and of tertbutylbenzene occurring in the Cg fraction from the following seven repre entative crudes: (A) Ponca, Okla.; (B) East Texas; (C) Bradford, Pa. ; (D) Greendale-Kawkawlin, Mich.; (E) Winkler, Tex. ; (F) M idway, Calif. ; (G) omoe, T ex. I. Introduction Although the eight possible aromatic hydro­ carbons whose normal boiling points are below The previous \vork of the American Petroleum 160 0 C were relatively easily determined (from Institute Re ear'ch Project 6 on the hydrocarbons measurements of boiling points, refractive in­ in the gasoline fraction of seven representative dices, and freezing points), the twelve possible crudes has been described in three earlier reports aromatic hydrocarbons in the range 160 0 to 180 0 C of investigations [1, 2, 3] * are present in uch relatively smaller amounts, At the time of the last report, the status of the and with such small differences in boiling point, work was as follows: that it is possible to obtain from the boiling point­ (a) Each of the seven naphthas had been sepa­ volume CUl'ves (on the limited quantity of mate­ rated by adsorption into an aromatic portion and rial processed) only values for close-boiling mix:­ a paraffin-naphthene portion. tures (usually pairs). Further, the lack of ade­ (b) Each paraffin-naphthene portion and each quate amolUlts of nearly pure stocks of each of aromatic portion had been separately distilled the component hydrocarbons made it impossible analytically. to utilize the method of determining individual (c) For the paraffin-naphthene portion, the hydrocarbons in mixtures of hydrocarbons by analysis of the individual components normally measuring freezing points [4,5]. boiling below 102 0 C had been completed, and, in As purified samples of these allrylbenzenes addition, the amounts of n-octane and n-nonane had been evaluated. The analysis of the paraffins were becoming available for spectrometer cali­ and naphtoones normally boiling in the range 102 0 bration, it is was evident that the analysis of the to 180 0 C was in process. individual aromatic hydrocarbons in the material (d) For the aromatic portion, the analysis of normally boiling above 160 0 C could be per­ the individual components normally boiling belo w formed successfully by spectrographic methods. 160° C has been completed. Accordingly, with the approval of the Advisory I Tbis investigation was performed as part of the work of the Ameri can Committee for the American Petroleum Institute Petroleum Institnte Research P roject 6 on the "Analysis, Purification, and R esearch Project 6, the cooperation of three Properties of Hydrocarbons" at t be National Bureau of Standards. ' Presented before the Divisio n of Petrolenm Chcmistry of the American laboratories that had experience in the spectro­ Chemical Society at Atlantic City, T. J ., April , 1947. graphic analysis of the Co alkylbenzenes was en­ 3 Research Associate on thc Amcrican Petroleum Institute Research Pro· ject 6 . listed. These laboratories were those of the • F igures in brackets in dicatc tbe literature references at tbe end of this paper. Socony-Vacuum Oil Co., Paulsboro, N. J., the Alkylbenzenes in Petroleum 425 Standard Oil Development Co., Elizabeth, N. J., were blended,4 into fi ve lots, as shown in figures and the Sun Oil Co., Norwood, Pa. The So cony­ 1 to 7, inclusive, which give the temperature­ Vacuum and Standard Oil Development Labor­ volume curves from the original analytical distil­ atories agreed to make infrared and the Sun Oil lations of these materials, as previously given m Laboratory, Raman spectral measurements. the second published report5 of this work [2]. • Altbough two of tbe cooperatillg laboratori es preferred to have tbe blcnd­ n. Material Analyzed ing for spectrographic analysis made from "flat to flat" rather than from "break to break," tbe material had previously been blended in the latter way for five of tbe napbthas in order to reduce losses by evaporation and, The seven naphthas under investigation, which therefore, the blending for the remaining two naphthas was also made from have been described in detail in the previous "break to brcak." This made the spectrographic analyses marc difficult for those laboratories wbose normal opcrating procedures were based on blending reports [1, 2, 3], arc the following: A, Ponca, from "flat to flat." Okla.; B, East Texas; C, Bradford, Pa.; Green­ 5 The figures 8 to 14 in the prc\-iollsly published report give, except for tbe Bradford (Pa.) and Winkler ('I'ex.) naphthas, a plot of refractive index dale-Kawkawlin, Mich.; E, Winkler, T ex.; F, against volume. rr he aromatic portions of five of the naphthas, Ponca Midway, Calif. ; G, Conroe, T ex. (Okla.), East Texas, Greendale-Kawkawlin (Mich.), Midway (Cali f.) , and Con roe (Tex.), arc sren to be Sllbstantially 100 perce nt aromatic, by com­ 0 The aromatic portions, boiling between 148 parison of the values of refractive index of the aromatic distillate and of the and 180 0 C, from each of the seven naphthas, pure components (indicated by CrO,ses at the 8PJ'rorriate rlaces). c c I I , • e - 1,1 , I' , I I 1" , I :~~ c~ c~ , I I I • v e , , c c 20 C DD.. , , , , I , I, ~ ~ , I , I I I I, I , ~~ ~~ , c ~ ~ I I I I • 0 0 , 200 , I l . DD.. I I , , D. c: , ~~ I , , , '1 I l , , I , ; ~:~ , I ~ I , , .D coo '1 , 0 ~ . ~ .~ , I I , I I , , , , -;'~P..~ ~ , , Q. ~ 0 0 , , , D "" 0 , , I , .. I , cc I , . ~~ ·7 ·7 190 I I , I ~ .. , , .. ~~~ , ~ I . ~;~ ~ cc E •• , 19 0 , , c ;~ '7 ->.. >- '" I ,.., -,c-'= . DD.. Of ~ ~ D ~ , D D. " ~ I · · .! . ~; ; ~~ ,;, T- , ~ D C ~ C ~~ >-~ E E D . , , >. E · ~ E ;; E N , , · D E-E- ;,;, ++ ~ ~~ I ·" ~ ~ , E D A~ · I D. >. ~ , T , ~ . ~ ~~ I J ~ ~ ~ E ~f , I >. I I 0 · ] -- I ( , , ~ 180 , ~ D oj" i , I · I'- I I .. : : II <; I ~ ~: c E '" .. I , I'- 180 N I , I I II >. N , , , ·c .c on - , , ~· : ! I c , I ,.; i , , E c + - f- ·"c .c~ + T '" >. , , , I E D. D. .;. ; ~ ~ ~ ,..; <l: DD· . I , 0 >. '>.>. , ~ ~ ~ ~ ~ I I'- 0 E T 0 ~ , , ~ 0 o ., I'- ~ T 170 ~ ,..J , 170 I I l- , , I ~ , <I I n, I , , I , ,..J f- ,' ,I I 0 ) 0 z , , 0 , , z Cl. , 160 160 I I EAST TEXAS NAPHTHA I- z '"z 0 PONCA, OKLA ...J a. 0 AROMAT IC PORTION NAPHTHA CD <!) 15 0 150 z AROMATIC PORTION ...J 0 m L Of 4 I 2 3 4 I I I I 3 I • O. ~~ ~ I 5 140 140 io 20 )0 04 0 ~o 60 70 eo 90 100 ~ 0 10 20 30 40 '0 60 70 80 90 100 I I r"""", , 1 , 1 I I I 1 I _.ARO~ "T IC PORTION 148 TO 180·C __ I" "'''''' AR OMATIC PORTION I 200 250 300 350 300 350 400 450 VOLUME IN ML VOLUME I N M L F I G. 2 FIGURE; 1. Plot of the boiling point as a function of the FIGURE 2. Plot of the boiling point as a function of the volume faT the C g fmction of the aTomatic portion oJ Ihe volume JOT the C9 fraction of the Momatic portion of the Ponca, Okla., naphtha. East Texas naphtha. The lot num bers refer to the portions of the distillate reblended for spectro­ The lot numbers refer to tbe portions of tbe distillate rcblenclcd for spectra· graphic examination. graphic examination . 426 Journal of Research For spectrogTaphic examination by the coo pcra t­ I, I- , ·o .C ing laboratories, the following sample were 200 fil'l I I I C ·" ." I · • C I I I ·" .0 ~ ~ I o • prepared and transmitted: I I I -;.~ I I I I " ~ ~ "· 0 o 0 I I I ...g-.Q a 0- To the So cony-Vacuum Oil Co. and Standard I I I I I I ~ Oil D evelopment Co., for infrared analysis : I I 0 I E 190 ~ D. I . D Samples (4 to 5 ml) of each of the five lots (1 to 5) D. 0 E I ..~ c 0 I · D. ~ . of each of the seven naphthas . , .0 . ~ E N E E J'- ~ D HI:I , · ~ ; . ~ J'- "; I E , 0 ~ 1- t /-;., .!. To the Sun Oil Co., for Raman analysis: Samples E '"-'- D, . I- ~ v ., ?[ ':( .;. ~ - (7 to 8 ml) of lot 3 of the East Texas naphtha, and « 180 .. · ~ ~ '" I I I I,' "o 0" .;, I i I I 111 ' 0 .. ..; I I lot 1 of the Bradford, Pa., Greendale-Kawkawlin, E I I I 0 "D - I l >'>. T I I ~~ E T l I I , Z ~ 0 I -. I l.. Mich. , and Midway, Calif., naph thas; Samples ~" I I I I o ~ I I (13 to 15 ml) of each of the remaining lots, except I- .!!, ::, I 170 I c..:-e-~ z I I I r) lot 1 of East Texas and Conroe, Tex., naphthas. 0 I I I I a. I I , , I I , As the pllre hydrocarbons representing the , I (9 I I z I I expected components of lot 5 were at that time ...J I 160 I not yet available for calibrating spectrometers, 0 I m I I BRA DFORD , PENN A ,NAPHTHA I I ARO MATIC PORTION , .0 150 200 , ·o ." , , I .C "• 0 ,I I CD.
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